MXPA01000482A

MXPA01000482A - Polycyclic thiazolidin-2-ylidene amines, method for the production and use thereof as medicaments

Info

Publication number: MXPA01000482A
Application number: MXPA/A/2001/000482A
Authority: MX
Inventors: Hans Jochen Lang; Karl Geisen; Gerhard Jahne
Original assignee: Sanofiaventis Deutschland GMBH
Priority date: 1998-07-17
Filing date: 2001-01-15
Publication date: 2002-02-26

Abstract

The invention relates to polycyclic thiazolidin-2-ylidene amines and the physiologically acceptable salts and physiologically functional derivatives thereof. Disclosed are polycyclic thiazolidin-2-ylidene amines of formula (I), wherein the radicals mentioned have the meanings as cited. The invention also relates to the physiologically acceptable salts and to a method of production thereof. The compounds can be used as anoretics.

Description

TIAZOLIDIN-2-POLYCYCLIC ILIDENAMINS, METHOD FOR THEIR PRODUCTION AND USE THEREOF AS DRUGS The invention relates to polycyclic thiazolidin-2-ylidenamines, and to their physiologically tolerable salts and physiologically functional derivatives. Thiazolidine derivatives having an anorexic action have already been described in the prior art (Austrian Patent No. 365181). The object of the invention is to prepare additional available compounds that have an anorexic action that can be used therapeutically. Regarding this aspect, the object was particularly to find also compounds in which the anorexic action is increased in comparison with the compounds of AT 365181. The invention therefore relates to polycyclic thiazolidin-2-ylidenamines of the formula I wherein A) Y is a direct bond, -CH2-, -CH2-CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 is CN, COOH, COO-alkyl (C? -C6), CONH2, CONH-alkyl (Ca-C6), CON [alkyl ((C? -C5),] 2, (C2-C6) alkyl, alkenyl ( C2-C6), alkynyl (C2-C6), 0-CH2-CF3 / 0-CH2-CF2-CF3 O-alkyl (C4-Ce), where in the alkyl radicals one or more or all of the hydrogen atoms can be replaced by fluorine or a hydrogen can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, SO-alkyl (C? -C6), SO- (CH2) n-phenyl, S02-alkyl (C? -C6), S02- (CH2) n-phenyl, where n can be equal to 0- 6 and the phenyl radical can be substituted up to twice by F, Cl, Br, OH, CF5, N02, CN, OCF3, O-alkyl (C? -C6), alkyl (C? -C6), NH2; NH2, NH-alkyl (Cx-Ce), N- ((C? -C6) alkyl) 2, NH-acyl (C1-C7), phenyl, biphenyl, O- I CH2) n-phenyl, where n can be = 0 - 6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, biphenyl rings, Naphthyl, pyridyl, furanyl or thienyl in each case can be substituted one to three times by F, Cl, Br, I, OH, CF3, N02, CN, OCF3, O-alkyl (C? -C6), alkyl (C1-) C.5), NH2, NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, S02-CH3, COOH, COO-alkyl (C? -C6), CONH ?; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R1 'is H, F, Cl, Br, I, CH3, CF3, O-alkyl (C? -C3), N02, S02-NH2, S02NH-alkyl? (C? -C6), S02 N [alkyl (C? -C6)] 2 or RI; R2 is H, (C? -C6) alkyl, (C3-C6) cycloalkyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, C ( 0) - (CH2) n-phenyl, C (0) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl, C (0) - (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C? -C6); C (0) -alkyl (C? -C6), C (0) -cycloalkyl (C3-C6); R3 is H, (C? -C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2-C00 alkyl (Ci-C.,), CH2-COO cycloalkyl (C3-C8), CH2-C00H, CH2-CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n it can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, 0-alkyl (C: -C6); alkynyl (C2-C6), alkenyl (C2-C6), C (0) 0CH3, C (0) OCH2CH3, C (0) 0H, C (0) NH2, C (0) NHCH3, C (0) N ( CH3) 2, 0C (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); R5 is alkyl (Ci-Cß), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl ,, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-, or -CH2-CH2-CH2-CH2-; or B) Y is a direct bond, -CH2- or -CH2-CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 'independently among them are H, F, Cl, Br, I, N02, CN, COOH, COO-alkyl (C? -C6), CONH2, CONH-alkyl (C? -C6), CON-N-alkyl (( C? -C6)? 2, alkyl (C? -C6), alkenyl (C2-C6) / alkynyl (C2-C6); O-alkyl (C? -C6), 0-CH2-CF3, 0-CH2- CF2-CF3, O-alkyl (C-C6), wherein in the alkyl radicals one or more or all of the hydrogen atoms may be replaced by fluorine, or a hydrogen atom may be replaced by OH, OC ( ) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, SO-alkyl (C? -C6), SO- ( CH2) n-phenyl, S0-alkyl (C? -C6), S02- (CH2) n-phenyl, where n can be = O-6 and the phenyl radical can be substituted up to twice by F, Cl, Br, OH, CF3, N02, CN, OCF3, 0-alkyl (C? -C6), alkyl (C? -C6) # NH; S02-NH2, S02NH alkyl (C? -C6), S02N [alkyl (C? C6)] 2, NH2, NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, NH-acyl (C1-C7), phenyl, biphenyl, O- (CH2) n- phenyl, where n can be = 0-6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings in each case may be substituted up to 3 times by F, Cl, Br, I, OH, CFj, N02, CN, 0CF3, O-alkyl (d-C6), alkyl (C? -C6), NH2, NH-alkyl (C ? -C6), N- ((C? -C6) alkyl) 2 / S02-CH3, COOH, COO-alkyl (C? -C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is H, alkyl (C? -C6), cycloalkyl (C3-C6), (CH2) r-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, C (0) - (CH2) n-phenyl, C (0) - (CH2) n-thienyl, C (O) - (CH2) n-pyridyl, C (O) - (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F , CN, CF3, alkyl (C? -C3), OH, O-alkyl (C? -C6); C (O) -alkyl (C? ~ C6), C (0) -cycloalkyl (C3-C6); R3 is (C4-C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2-C00 alkyl (C? -C6), CH2-COO cycloalkyl (C3-C8), CH2-C00H, CH2-C0NH2, CH-2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2), -, - pyridyl, (CH2) n-furyl, where n it can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C? -C.), OH, O-alkyl ( C? -C6); alkynyl (C2-C6), alkenyl (C2-C6), C (0) 0CH3, C (0) OCH2CH3, C (0) 0H, C (0) NH2, C (0) NHCH3, C (0) N ( CH3) 2, 0C (0) CH3; R4 is alkyl (Ci-Ce), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0 - and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); R5 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl ,, (CH2) n-pyridyl, (CH2) n_furil, where n can be = 0 And wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6), or either R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-, or -CH2-CH2-CH2-CH2-; or C) Y is a direct bond, -CH2- or -CH2-CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 'independently among them are H, F, Cl, Br, I, N02, CN, COOH, COO-alkyl (C? -C6), CONH2, CONH-alkyl (C? -C6), CON [alkyl ( (C? -C6)] 2, (C? -C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, O-alkyl (C? ~ C6), 0-CH2-CF3, 0-CH2 -CF2-CF3, O-C4-C6 alkyl, where in the alkyl radicals one or several or all of the hydrogen atoms can be replaced by fluorine or a hydrogen can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (Ci-Ce), S- (CH2) n-phenyl, SO-alkyl (C? -C6), SO- (CH2) n- phenyl, S02-alkyl (C? -C6), S02- (CH2) n-phenyl, where n can be = 0-6 and the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, 0CF3, 0-(C1-C3) alkyl, (C? -C6) alkyl, NH; S02-NH2, S02NH alkyl (C? -Cd), S02N.alkyl (C? -C6)] 2, NH2, NH-alkyl (C? -C6), N- ((C? -C) alkyl) 2, NH-acyl (C1-C7), phenyl, biphenyl, O- (CH2) n-phenyl, where n can ser = 0-6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings in each case may be substituted one to 3 times by F, Cl, Br, I, OH, CF3, N02, CN, 0CF3, O-alkyl (C? -C6), alkyl (C? ~ C6), NH2, NH-alkyl (C? C6), N- (alkyl (C? -C6)) =, S02-CH3, COOH, COO-alkyl (C? -C6), CONH2; 1,2,3-triazol-5-yl, where the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-ylc, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is (C6C6) alkyl, (C3-C6) cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) ) n-furyl, C (O) - (CH2) n-phenyl, C (O) - (CH2) n-thienyl, C (O) - (CH2) n-pyridyl, C (O) - (CH2) n -furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C? ~ C3), OH, O -alkyl- (C? -C6); C (O) -alkyl (C? -C6), C (O) -cycloalkyl (C3-C6); R3 is H, (C4-C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2-COO alkyl (C? -C6), CH2-COO cycloalkyl (C3-C8), CH2- COOH, CH2-CONH ?, CH2-C NHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice, by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C? -C6); alkynyl (C2-C6), alkenyl (C2-C6), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) NHCH3, C (0) N ( CH3) 2, OC (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); R5 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-, or -CH2-CH2-CH2-CH2-; or D) Y is a direct bond, -CH2- or -CH2-CH2-; X is CH (phenyl), wherein the phenyl radical can be substituted by F, Cl, Br or I, O, S, SO, S02 or N-R6; R1 and R1 'independently among them are H, F, Cl, Br, I, N02, CN, COOH, COO-alkyl (C? -C6), C0NH2, CONH-alkyl (C? ~ C6), CON [alkyl ( (C? -C6)] 2, (C? -C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, O-alkyl (C? -C6), 0-CH2-CF3, 0-CH2 -CF'2-CF3, O-(C4-C6) alkyl, wherein in the alkyl radicals one or more or all of the hydrogen atoms may be replaced by fluorine, or a hydrogen atom may be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, SO-alkyl (C? -C6), SO- (CH2) n-phenyl, S0-alkyl (C? -C6), S02- (CH2) n-phenyl, where n can be = 0-6 and the phenyl radical can be substituted up to two times by F, Cl , Br, OH, CF3, N0, CN, OCF3, 0-alkyl (C? -C6), alkyl (C? -C6), NH2, S02-NH2, S02NH-alkyl? (Ci-Ce), S02N- [ alkyl (C? -C6)] 2, NH2, NH-alkyl (C? -C5), N- ((C? -C6) alkyl) 2, NH-acyl (C? -C), phenyl, biphenyl, - (CH2) n-phenyl, where n can be = 0 - 6, 1-nafti or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings in each case they can be substituted one to three times by F, Cl, Br, I, OH, CF3, N02, CN, OCF3, O-alkyl (C? -C6), alkyl (Ci-C5), NH2, NH- alkyl (C? -C6), N- ((C? -C6) alkyl) 2, COOH, COO-alkyl (C? -C6), C0NH2; 1,2,3-triazol-5-yl, where the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, where the tetrazolide ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is H, (C? -C6) alkyl, (C3-C6) cycloalkyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, C (0) ) - (CH2) n-phenyl, C (0) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl, C (0) - (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C? -C5); C (0) -alkyl (C? -C6), C (0) -cycloalkyl (C3-C6); R3 is H, (C? -C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2-C00 alkyl (C? -C6), CH2-C00 cycloalkyl (C3-C8), CH2 -C00H, CH2-CONH2, CH2-C0NHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) -.- pyridyl, (CH2) n-furyl, where n it can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF, (C1-C5) alkyl, OH, O-alkyl (C? C6); alkynyl (C2-C6), alkenyl (C2-C6), C (0) 0CH3, C (0) OCH2CH3, C (0) 0H, C (0) NH2, C (0) NHCH3, C (0) N ( CH3) 2, 0C (0) CH3; R4 is alkyl (Cx-C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl ,. (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3 / (C1-C3) alkyl, OH, O-alkyl (C6C6); R5 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-, or -CH2-CH2-CH2-CH2-; or R6 is S02- (C6H4-4-CH3) or E) Y is a direct bond, -CH2- or -CH2-CH2-; X is CH2, CH (CX), CH (C2H5), CH (C3H7); R 1 is H, F, Cl, Br, I, CH 3, CF 3, O-(C 1 -C 3) alkyl; R1 'is H, F, Cl, Br, I, N02; R2 is H; R3 is H, (C1-C3) alkyl; R 4 is phenyl, where the phenyl radical can be substituted up to two times by F, Cl, Br, I, alkyl (C? -Cd), cycloalkyl (C3-C6), O-alkyl (C1-C3), CF3, OCF3 , 0-CH2-phenyl, COOH, COO-alkyl (C? -C6), COO-cycloalkyl (C3-C6), CONH2; R5 is phenyl, where the phenyl radical can be substituted up to twice by F, Cl, Br, I, alkyl (Ci-Ce), cycloalkyl (C3-C6), O-alkyl (C1-C3), CF3, OCF3, 0-CH2-phenyl, COOH, COO-alkyl (C? -C6), COO-cycloalkyl (C3-C6), CONH2; and their physiologically tolerable salts and their physiologically functional derivatives. Preferred compounds of the formula I are the compounds in which A) Y is a direct bond, -CH2; X is CH2, CH (Cr3), CH (C2H5), CH (C3H7); R1 is CN, COOH, COO-alkyl (C? -C6), CONH2, CONH-alkyl (Ci-C6), CON- [((C? -C6)] alkyl, (C2-C6) alkyl, alkenyl ( C2-C6), alkynyl (C2-C6), 0-CH2-CF3, 0-CH2-CF2-CF3, O-alkyl (C4-Cß), where in the alkyl radicals one or more or all of the hydrogen can be replaced by fluorine, or a hydrogen can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or (COOCH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, SO-alkyl (C? -C6) / SO- (CH2) n-phenyl, where the phenyl radical can be substituted up to twice by F , Cl, Br, OH, CF3, N02, CN, OCF3, 0-alkyl (C? -C6), alkyl (C? -C6); NH-alkyl (C? -C6), N- ((C? -C6) alkyl, NH-acyl (C1-C7), phenyl, 0- (CH2) n-phenyl, where n can be = 0-6 , 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, wherein the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be substituted one to three times by F , Cl, I, OH, CF3, CN, 0CF3, O-alkyl (C? -C6), alkyl (C? -C6), NH2, NH-alkyl (C? -C6), N- (alkyl (C? -C6)) 2, COOH, COO-alkyl (C? -C6), C0NH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R1 'is H, F, Cl, Br, I, CH3, CH3, O- (C1-C3) alkyl, S02-NH2 / S02NH-alkyl? (C? -C6), S02N- [alkyl (C? -C6) j2 or RI; R2 is H, (C? -C6) alkyl, (CH2) n ~ phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, C (0) - (CH2) n-phenyl, C (0) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F , CN, CF3, alkyl (C? ~ C3), OH, O-alkyl (C? ~ C6); R3 is H, (Cx-C6) alkyl, F, CN, O-alkyl (C? -C5), CH2-COO alkyl (C? -C (!), CH2-C00 cycloalkyl (C3-C8), CH2- C00H, CH2-CONH2, CH2-C0NHCH3, CH2-C0N (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (Ci-C3) alkyl, OH, O-alkyl (Ci-Ce), (C2-C6) alkynyl, alkenyl ( C2-C6), C (0) OCH; ¡, C (0) OCH2CH3, C (0) 0H, C (0) NH2, C (0) N (CH3) 2, 0C (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl , thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (Ci- C3), OH, O-alkyl (C? -C6); R5 is alkyl (C? -C6), cycloalkyl (C3-Ce), (CH2) nfenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C-, -C3), OH, O-alkyl (C? -C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-or -CH2-CH2-CH2-; or B) Y is a direct link, -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 'independently are H, F, Cl, Br, I, CN, COOH, COO-alkyl (C? -C6), CONH2, CONH-alkyl (Ci-Ce), CON- [alkyl ((C ? -C6)? 2, alkyl (C? -C6), alkenyl (C2-C6), alkynyl (C2-C6), O-alkyl (C? -C6), 0-CH2-CF3, 0-CH2-CF2 -CF3, O-C4-C6 alkyl, where in the alkyl radicals one or several or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen atom can be replaced by OH, OC (0) CH3, 0-CH2- Ph, NH2 or bier N (COOCH2Ph) 2; S-alkyl (C.-C6), S- (CH2) n-phenyl, SO-alkyl (C? -C6), SO- ( CH2) n-phenyl, wherein the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, OCF3, O-(C1-C5) alkyl, (C6-C6) alkyl; S02-NH2, S02NH-alkyl (C? ~ C6), S02N- [alkyl (Cx-C ^.} Z, NH-alkyl (C? -C6), N- (((C? -C6) alkyl) , NH-acyl (C1-C7), phenyl, 0- (CH2) n-phenyl, where n can be = 0-6,1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, naphthyl, pyridyl, furanyl or thienyl rings in each case can be substituted one to three times by F, Cl, I, OH, CF3, CN, 0CF3, O- alkyl (C? -C6), alkyl (C? -C6), NH2, NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, COOH, COO-alkyl (C? C6), C0NH2; 1, 2, 3-triazol-5-yl, where the triazole ring may be substituted in the 1-position, in the 2-o-position. in position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R 2 is H, (C 1 -C 6) alkyl, (CH 2) n -phenyl, (CH 2) n -thienyl, (CH 2) n -pyridyl, C (O) - (CH 2) n -phenyl, C (0) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F , CN, CF3, alkyl (Ci-C3), OH, O-alkyl (C? -C6); R3 is (C4-C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2-COO alkyl (C? -C6), CH2-C00 cycloalkyl (C3-C8), CH2-C00H, CH2-C0NH2, CH2-CONHCH3, CH2-C0N (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (Ci-C3), OH, O-alkyl (C6C6); alkynyl (C2-Cd), alkenyl (C2-C6), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) NHCH3, C (0) N ( CH3) 2, OC (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n -pyridyl, where n can be = 0-3 and where phenyl , thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (Ci-C3), OH, O-alkyl (C? -C6); R5 is (d-C6) alkyl, (C3-C6) cycloalkyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (Ci-C3), OH, O-alkyl (C? -C6), or R4 and R5 together form a group - CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-; or C) Y is a direct link, or -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 'independently among them are H, F, Cl, Br, I, CN, COOH, COO-alkyl (C? -C6), CONH2, CONH-alkyl (C? ~ C6), CON- [alkyl (( C? -C6)] 2, alkyl (C? -C6), alkenyl (C2-C6), alkynyl (C2-C6); O-alkyl (C? -C6), 0-CH2-CF3, 0-CH2-CF2-CF3, O-(C4-C6) alkyl, wherein in the alkyl radicals one or more or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (C; -C6), S- (CH2) n-phenyl, S02-alkyl (C? -C6), S02- (CH2) n-phenyl, where n can be = 0-6 and the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, OCF3, O-alkyl (C? -C6), alkyl (C? -C6), S02-NH2, S02NH-alkyl (C ? -C6), S02N- [alkyl (d-Ce)]?, NH-alkyl (Cx-C6), N- (alkyl (C? -C6)) 2, NH-acyl (C1-C7), phenyl , 0- (CH2) r-phenyl, where n can be = 0-4, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2- thienyl or 3-thienyl, where the phenyl, naphthyl, pyridyl, furanyl or thienyl rings in each case can be substituted one to three times by F, Cl, I, OH, CF3, CN, 0CF3, O-alkyl (Ci -Ce), alkyl (C? -C6), NH2, NH-alkyl (Cx-C6), N- (alkyl Lo (d-C6)) 2, COOH, COO-alkyl (C? -C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is (C6C6) alkyl, C2-C8 alkenyl, C2-C8 alkynyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, C (0) - (CH2) n -phenyl, C (0) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); R3 is H, alkyl (C? -C6), F, CN, O-alkyl (C? -C6), CH2-C00 alkyl (C? -Cfl), CH2-C00 cycloalkyl (C3-C8), CH2-C00H , CH2-C0NH2, CH2-C0NHCH3, CH2-C0N (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl , thienyl, pyridyl, in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C? ~ C3), OH, O-alkyl (C? -C6); alkynyl (C2-C6), alkenyl (C2-C6), C (0) 0CH;, C (0) OCH2CH3, C (0) 0H, C (0) NH2, C (0) N (CH3) 2, 0C (0) CH3; R 4 is alkyl (Ci-Cß), cycloalkyl (C3-Ce), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (Ci-C3), OH, 0-alkyl (C? -C6); R5 is alkyl (d-Ce), cycloalkyl (dd), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (Ci-C3), OH, O-alkyl (C? -C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, or -CH2-CH2-CH2-; or D) Y is a direct link, or -CH2-; X is CH (phenyl), where the phenyl radical can be substituted by F, Cl or Br, O, S, SO, S02 or N-R6; R1 and R1 'independently among them are H, F, Cl, Br., I, CN, COOH, COO-alkyl (C? -C6), CONH2, CONH-alkyl (Ci-Ce), CON- [alkyl Ud- CeH ?, alkyl (d-C6), alkenyl (C2-C6), alkynyl (C2-C6); O-alkyl (C? -C6), 0-CH2-CF3, 0-CH2-CF2-CF3, O-(C4-C6) alkyl, wherein in the alkyl radicals one or more or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (d-C6), S- (CH2) n-phenyl, S02-alkyl (C? -C6), S02- (CH2) n-phenyl, where n can be = 0-6 and the phenyl radical may be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, OCF3, O-alkyl (C? -Ce), alkyl (C? -C6); S02-NH2, S0NH-alkyl (C? -C6), S02N- [(C6-C6) alkyl] 2, NH2, NH-alkyl (C? -C6), N- (alkyl (d-C6)) 2, NH-acyl ( C1-C7), phenyl, O- (CH2) r-phenyl, where n can be = 0-6,1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or -furanyl or 2-thienyl or 3-thienyl, wherein the phenyl, naphthyl, pyridyl, furanyl or thienyl rings in each case can be substituted one to three times by F, Cl, I, OH, CF3, CN, OCF3 , O-alkyl (Ci-Ce), alkyl (d-C6), NH2, NH-alkyl (Ci-Ce), N- ((C? -C6) alkyl) 2, COOH, COO-alkyl (C? C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R 2 is H, (C 1 -C 6) alkyl, (CH 2) n -phenyl, (CH 2) n-thienyl, (CH 2) n -pyridyl, C (O) - (CH 2) n -phenyl, C (O) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F , CN, CF3, alkyl (Ci-C3), OH, O-alkyl (C? -C6); R3 is H, (C? -C6) alkyl, F, CN, O-alkyl (d-C6), CH2-COO alkyl (d-Ce), CH2-COO cycloalkyl (C3-C8), CH2-COOH, CH2 -CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl , pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (Ci- C3), OH, O-alkyl (C? -C6); alkynyl (C2-C6), alkenyl (C2-C6), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) NHCH3, C (0) N (CH3) 2, OC (0) CH3; R4 is alkyl (C? -C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and wherein phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl ( d.- C3), OH, O-alkyl (C? -C6); R5 is alkyl (C? -C6), cycloalkyl (C3-C?), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and wherein phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl ( C? ~ C3), OH, O-alkyl (C? -C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-or -CH2-CH2-CH2-; R6 is S02- (C6H4-4-CH3) or E) Y is a direct bond or -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 is H, F, Cl, Br, I, CH3, CF3, O- (C1-C3) alkyl, 'R1' is H, F, Cl, Br, I; R2 is H; R3 is H, (C1-C3) alkyl; R 4 is phenyl, where the phenyl radical can be substituted up to two times by F, Cl, Br, I, alkyl (C? -C6), cycloalkyl (C3-C6), O-alkyl (C1-C3), CF3, OCF3 , 0-CH2-phenyl, COOH, COO-alkyl (C? -C6), C0NH2; R5 is phenyl, where the phenyl radical can be substituted up to twice by F, Cl, Br, I, alkyl (C? -C6), cycloalkyl (C3-C6), O-alkyl (C1-C3), CF3, OCF3 , 0-CH2-phenyl, COOH, COO-alkyl (d-C6), CONH2; and their physiologically tolerable salts and physiologically functional derivatives. Particularly preferred compounds of the formula I are the compounds in which A) Y is a direct bond; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 is CN, COOH, COO-alkyl (C? -C6), CONH2, CON- [(Ci-C6)] alkyl, (C2-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl ), 0-CH2-CF3, 0-CH2-CF2-CF3, O-alkyl (C4-C5), wherein in the aryl radicals one or more or all of the hydrogen atoms can be replaced by fluorine, or else a hydrogen may be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (d-C6), S- (CH2) n-phenyl, SO-alkyl ( Ci-Ce), S0- (CH2) n-phenyl, where the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, OCF3, 0-alkyl (d-C6), alkyl (C? -C6), NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, NH-acyl (Ci-d), phenyl, O- (CH2) n-phenyl , where n can be = 0-6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the rings of phenyl, naphthyl, pyridyl, furanyl or thienyl in each case may be substituted one to two times by F, Cl, OH, CF3, CN, 0CF3, O- alkyl (C? -C6), alkyl (C? -C6), COOH, COO-alkyl (C? -C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R1 'is H, F, Cl, CH3, CF3, O- (C1-C3) alkyl, S02-NH2, S02NH-alkyl (Ci-C ..), S02N- [(CX-C6) alkyl] 2 or Rl; R 2 is H, (C 1 -C 6) alkyl, (CH 2) n -phenyl, (CH 2) n -pyridyl, C (O) - (CH 2) n -phenyl, C (0) - (CH 2) n -pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (d-C3), O-alkyl (C6C6); C (O) -alkyl (C? -C6); R3 is H, (C? -C6) alkyl, F, CN, O-alkyl (C? -C6), CH2-COO alkyl (C? -C6), CH2-COO cycloalkyl (C3-C8), CH2-COOH , CH2-CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C? -C3), O-alkyl (Ci-Ce); alkynyl (C2 ~ C), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) N (CH3) 2, 0C (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and wherein phenyl, pyridyl, in each case can to be substituted up to twice by Cl, F, CN, CF3, alkyl (d ~ C3), O-alkyl (C? -C6); R5 is (d-C6) alkyl, (C3-C6) cycloalkyl, (CH2) n-phenyl, (CH2) n-pyridyl, where n may be = 0-3 and wherein phenyl, pyridyl in each case may be substituted up to twice by Cl, F, CN, CF3, alkyl (d-C3), O-alkyl (C? -C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, or -CH2-CH2-CH2-; or B) Y is a direct link, -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 'independently of each other are H, F, Cl, Br, I, CN, COOH, COO-alkyl (C6C6), CONH2, CON- [alkyl ((dC6)] 2, alkyl (C) ? ~ C6), alkenyl (C2-C6), alkynyl (C2-C6), O-alkyl (C? -C6), 0-CH2-CF3, 0-CH2-CF2-CF3, O-alkyl (C4-C6) ), where in the alkyl radicals one or several or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, SO-alkyl (Ci-Ce), S0- (CH2) n-phenyl, where the phenyl radical may be substituted up to twice by F, Cl, OH, CF3, OCF3, O-alkyl (C? -C6), alkyl (d.-C?), S02-NH2, S02NH-alkyl (C? -C6), S02N- [alkyl (C? -C6)] 2, N- (alkyl (d-C6)) 2, NH-acyl (C1-C7), phenyl, 0- (CH2) n-phenyl, where n can be = 0- 6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the rings of phenyl, naphthyl, py idyl, furanyl or thienyl in each case can be substituted one to three times by F, Cl, Br, .1, OH, CF3, CN, 0CF3, O-alkyl (C? -C6), alkyl (C? -C6) ), NH2, N- (alkyl (d-C6)) 2, COOH, COO-alkyl (C? -C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is H, alkyl (d-C6), (CH2) n-phenyl, (CH2) n-pyridyl, C (0) - (CH2) n-phenyl, C (O) - (CH2) n-pyridyl, where n can be = 0-3 and wherein phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (Ci-d), OH, O-alkyl (C6C6); C (0) -alkyl (C? -C6); R3 is (C4-C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2-COO alkyl (C? -C6), CH2-COO cycloalkyl (C3-C8), CH2-COOH, CH2-CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-pyridyl where n can be = O-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (C6C6); alkynyl (C2-C6), C (0) 0CH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) NHCH3, C (0) N (CH3) 2 0C (0) CH3; R4 is alkyl (C? -C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl ( C? -C6); R5 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (C6C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-or -CH2-CH2-CH2-; or C) Y is a direct link or -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 'independently of each other are H, F, Cl, Br, I, CN, COOH, COO-alkyl (C6C6), CONH2, CON- [alkyl ((C6C6)] 2, alkyl ( C? -C6), alkenyl (C2-C6), alkynyl (C2-C6), O-alkyl (Ci-Ce), 0-CH2-CF3, 0-CH2-CF2-CF3, O-alkyl (-C?) where in the alkyl radicals one or several or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen can be replaced by OH, 0C (0) CH3, 0-CH2-Ph, NH2 or N ( COOCH2Ph) 2; S-alkyl (C? ~ C6), S- (CH2) n-phenyl, S02-alkyl (C? -C6), S02- (CH2) n-phenyl, where n can be = 0-6 and the phenyl radical may be substituted up to two times by F, Cl, Br, OH, CF3, N02, OCF3, O-alkyl (Ci-Ce), alkyl (Ci-Ce); S02-NH2, S02NH-alkyl (d-C6), S02N- [(C? -C6) alkyl] 2, N- (alkyl (d-Ce)) 2, NH-acyl (C1-C7), phenyl, O - (CH2) n-phenyl, where n can be = 0-4, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the rings of phenyl, naphthyl, pyridyl, furanyl or thienyl in each case can be substituted one to three times by F, Cl, I, OH, CF3, CN, OCF3, O-alkyl (Ci-Ce) , (C1-C5) alkyl, NH2, NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, COOH, COO-alkyl (C? -C6), C0NH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is (C6C6) alkyl, C2-C8 alkenyl, C2-C8 alkynyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, C (0) - (CH2) n -phenyl, C (0) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); C (0) -alkyl (Ci-c6); R3 is H, (C? -C6) alkyl, F, CN, O-alkyl (C? -C6), CH2-C00 alkyl (C? -C6), CH2-C00 cycloalkyl (C3-C8), CH2-C00H , CH2-C0NH2, CH2-C0NHCH3, CH2-C0N (CH3) 2, (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (C6C6); alkynyl (C2-C6), C (0) 0CH3, C (0) OCH2CH3, C (0) 0H, C (0) NH2, C (0) N (CH3) 2, 0C (0) CH3; R4 is alkyl (C? ~ C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl ( C? -C6); R5 is alkyl (Ci-Cβ), cycloalkyl (-), (CH 2) n -phenyl, (CH 2) n -pyridyl, where n can be = 0-3 and wherein phenyl, pyridyl, in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (C6C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-or -CH2-CH2-CH2-; or D) Y is a direct link, -CH2-; X is CH (phenyl), where the phenyl radical can be substituted by F or Cl, O, S, S02 or N-R6; R1 and R1 'independently of each other are H, F, Cl, Br, I, CN, COOH, COO-alkyl (C? -C6), CONH2, CON- [alkyl ((Ci-d)] .., alkyl ( d-C6), alkenyl (C2-C6), alkynyl (d-C6), O-alkyl (C? -C6), 0-CH2-CF3, O-CH2-CF2-CF3, O-alkyl (-) where in the alkyl radicals one or several or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen can be replaced by OH, 0C (0) CH3, 0-CH2-Ph, NH2 or N ( COOCH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, S02-alkyl (C? -C6), S02- (CH2) n-phenyl, where n can be = 0-6 and the phenyl radical may be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, 0CF3, O-alkyl (C? -C6), alkyl (C? -C6); S02-NH2, SO? NH-alkyl (Ci-Ce), S02N- [alkyl (d-C6)] 2, NH2, N- ((C? -C6) alkyl) 2, NH-acyl (C1-C7) , phenyl, 0- (CH2) n-phenyl, where n can be = 0-6,1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the rings of phenyl, naphthyl, pyridyl, furanyl or thienyl in each case can be substituted one to three times by F, Cl, I, OH, CF3, CN, 0CF3, O-alkyl ( Ci-Ce), alkyl (C? -C6), NH2, N- ((C? -C6) alkyl) 2, COOH, COO-alkoyl (C? -C6), C0NH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R 2 is H, (C 1 -C 6) alkyl, (CH 2) n -phenyl, (CH 2) n-thienyl, (CH 2) n -pyridyl, C (0) - (CH 2) n -phenyl, C (O) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F , CN, CF3, alkyl (C, -d), OH, O-alkyl (Ci-Ce); C (O) -alkyl (d-C6); R3 is H, alkyl (Ci-Ce), F, CN, O-alkyl (Ci-Ce), CH2-COO alkyl (C? -C6), CH2-C00 cycloalkyl (C3-C8), CH2-COOH, CH2 -CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH:) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (C6C6); alkynyl (C2-C6), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) NHCH3, C (0) N (CH3) 2, OC (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (Ci-Ce); R5 is alkyl (C? ~ C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl ( C? -C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-; R6 is S02- (C6H4-4-CH3) or E) Y is a direct bond or -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 is H, F, c:., CH3, CF3, O-(C1-C3) alkyl; R1 'is H, F, Cl; R2 is H; R3 is H, (C1-C3) alkyl; R4 is phenyl, where the phenyl radical can be substituted up to two times by F, Cl, (C? -C6) alkyl, (C3-C6) cycloalkyl, O-C1-C3 alkyl, CF3, 0-CH2-phenyl , COOH, COO-alkyl R5 is phenyl, where the phenyl radical can be substituted up to two times by F, Cl, alkyl (Ci-Cß), cycloalkyl (C3-C6), O-alkyl (d-C3), CF3, 0-CH2-phenyl, COOH, COO-alkyl (C? -C6), CONH2; and their physiologically tolerable salts and physiologically functional derivatives. Very particularly preferred compounds of the formula I are the compounds in which Y is a direct bond; X is CH2 R1 and R1 'independently are H, F, Cl, CN, COOH, CONH2, COO- (C1-C3) alkyl, alkyl (Ci-Ce), alkenyl (C2-C6), alkynyl (C2- d), where in the alkyl, alkenyl and alkynyl radicals, a hydrogen can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; OCF3, OCH2CF3, O-alkyl (C? -C4), wherein in the alkyl radicals one or more or all of the hydrogen atoms may be replaced by fluorine or a hydrogen atom may be replaced by OH, OC ( CH3, 0-CH2- Ph, NH2 or N (COOCH2Ph) 2; S02-alkyl (d-d), S02- (CH2) n-phenyl, where n can be = 0 -3 and the phenyl radical can be substituted by F, Cl, OH, CF3, O-(C1-C4) alkyl; NH- (CO) -alkyl (d-C3); (CH2) n-phenyl, S- (CH2) n-phenyl, O- (CH2) n-phenyl, where n can be = 0-3, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the rings of phenyl, naphthyl, pyridyl, furanyl or thienyl in each case may be substituted by F, Cl, CF3, alkyl (d- C6), 0-alkyl (Ci-Ce) and where in the alkyl radicals a hydrogen atom can be replaced by OH, 0C (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted in the 1-position, in the 2-position or in the 3-position by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is H, (C1-C4) alkyl, (C5-C6) cycloalkyl; (CH2) n-phenyl, where n can be = 0-3, C (0) -alkyl (C? ~ C4), or C (O) -phenyl; R3 is F, (C4-C6) alkyl, CH2-phenyl, where phenyl may be substituted up to two times by F, Cl, CF3, O-C1-C3 alkyl, alkyl (dd,), COOH, CO-O -alkyl (C1-C3) or CONH2; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, where n can be = 0-3 and the phenyl radical can be substituted up to two times by F, Cl, O-alkyl (C? -C4) or OH; R5 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) r.-phenyl, where n can be = 0-3 and the phenyl radical can be substituted up to two times by F, Cl, O- alkyl (Ci-d) or OH; and its physiologically tolerable salts. Particular preference is given to compounds of formula I which have the following structure: Particularly the compound: ral The invention relates to compounds of the formula I, in the form of their racemos, mixtures of racemos and pure enantiomers, and to their diastereomers and mixtures thereof. Taking into account its high solubility in water, compared to the initial or base compounds, the pharmaceutically tolerable salts are especially suitable for medical applications. These salts must have a pharmaceutically tolerable anion or cation. Suitable pharmaceutically tolerable acid addition salts of the compounds according to the invention are salts of inorganic acids such as hydrochloric acid, hydrobromic, phosphoric, metaphosphoric, nitric, sulfonic and sulfuric acid, and of organic acids such as for example acetic acid, benzenesulfonic, benzoic, citric, ethanesulfonic, fumaric, gluconic, glycolic, isethionic, lactic, lactobionic, maleic, rtialic, methanesulfonic, succinic, p-toluenesulfonic, tartaric and trifluoroacetic acids. For medical purposes, the chlorine salt is used in a particularly preferred manner. Suitable pharmaceutically tolerable basic salts are ammonium salts, alkali metal salts (such as, for example, sodium and potassium salts) and toric alkali metal salts (such as, for example, magnesium and calcium salts). Hydrobromides and hydrochlorides, particularly hydrochlorides, are preferred. Salts with a pharmaceutically intolerable anion are also included within the scope of the present invention as intermediates useful for the preparation or purification of pharmaceutically tolerable salts and / or for use in non-therapeutic applications, for example, in in vitro applications. - The term "physiologically functional derivative" used herein refers to any physiologically tolerable derivative of a compound according to the present invention, for example, an ester which, when administered to a mammal such as, for example, to a human being, can (direct or indirectly) forming such a compound or an active metabolite thereof Prodrugs of the compounds according to the present invention are a further aspect of the present invention Such prodrugs can be metabolized in vivo to provide a compound according to the invention. they can themselves be active or inactive The compounds according to the present invention can also be present in various polymorphic forms, for example, as amorphous and crystalline polymorphic forms All polymorphic forms of the compounds according to the present invention are included in the scope of the present invention and they are a further aspect of the invention. In the following, all references to "compound (s) according to formula (I)" refer to compound (s) of formula (I) in accordance with that described above, and to their salts, solvates and physiologically functional derivatives in accordance with what is described here. The amount of a compound according to formula (I) that is necessary in order to achieve the desired biological effect depends on several factors, for example, the specific compound selected, the intended use, the form of administration and the clinical condition of the patient. In general, the daily dose is within a range of 0.3 mg to 100 mg (typically 3 mg to 50 mg) per day per kilogram of body weight, such as 3-10 mg / kg / day. An intravenous dose can be found, for example, within a range of 0.3 mg to 1.0 mg / kg, which can be appropriately administered in the form of an infusion of 10 ng to 100 ng per kilogram per minute. Suitable solutions for infusion for these purposes may contain, for example, 0.1 ng to 10 mg, typically 1 ng to 10 mg per milliliter. Individual doses may contain, for example, from 1 mg to 10 g of the active compound. Thus, ampoules for injections may contain, for example, 1 mg to 100 mg, and orally administrable single dose formulations such as tablets or capsules may contain, for example, 1.0 to 1000 mg, typically 10 to 600 mg . In the case of pharmaceutically tolerable salts, the aforementioned weight details- refer to the weight of the thiazolidin-2-ylidene ion derived from the salt. For prophylaxis or therapy of the aforementioned conditions, the compounds according to formula (I) can be used as the compound itself, but are preferably present in the form of a pharmaceutical composition with a tolerable carrier. The vehicle must obviously be tolerable in the sense that it must be compatible with the other constituents of the composition and that it should not be harmful to the patient's health. The vehicle can be a solid or a liquid or both and is preferably formulated with the compound as a single dose, for example as tablets that can contain from 0.05% to 95% by weight of the active compound. Additional pharmaceutically active substances may also be present, including additional compounds according to formula (I). The pharmaceutical compositions according to the present invention can be prepared by one of the known pharmaceutical methods, consisting essentially of the mixture of the constituents with pharmacologically tolerable excipients and / or auxiliaries. Pharmaceutical compositions according to the present invention are compositions suitable for oral, rectal, topical, oral (for example sublingual) and parenteral (for example subcutaneous, intramuscular, intradermal or intravenous) administration, even though the most appropriate form of administration in each case individual depends on the nature and severity of the condition to be treated and on the nature of the compound according to the formula (I) used in each case. Sugar-coated formulations as well as extended-release formulations coated with sugar are also included within the scope of the present invention. Enteric and acid resistant formulations are preferred. Suitable enteric coatings include cellulose acetate phthalate, polyvinylacetate phthalate, hydroxypropylmethylcellulose phthalate, and anionic polymers of methacrylic acid and methyl methacrylate. Pharmaceutical compounds suitable for oral administration may be present in separate units such as for example in the form of capsules, dragees, pills or tablets and in each case contain a certain amount of the composition according to the formula (I); as powders or granules, as a solution or suspension in an aqueous or non-aqueous liquid; as an oil in water or water in oil emulsion. As already mentioned, these compositions can be prepared by any suitable pharmaceutical method which includes a step in which the active compound and the vehicle (which may consist of one or more additional constituents) come into contact. In general, the compositions are prepared by uniform and homogeneous mixing of the active compound with a finely divided solid carrier and / or a liquid carrier, after which the product is shaped, if necessary. Thus, a tablet can be prepared by pressing or profiling a powder or granules of the compound, if appropriate with one or more additional constituents. Pressed tablets may be prepared in free flowing form, such as, for example, in the form of powder or granules, by forming the compound in tablets, if appropriate, mixed with a binder, lubricant, inert diluent and / or a surfactant / dispersing agent. or various surfactant / dispersing agents in a suitable machine. The profiled tablets can be prepared by profiling the humidified powder compound with an inert liquid diluent in a suitable machine. Pharmaceutical compositions which are also suitable for oral (sublingual) administration include lozenges containing a compound according to formula (I) with a zante flavor, usually sucrose and gum arabic or tragacanth, and lozenges including the compound in an inert base such as for example gelatin and glycerol or sucrose and gum arabic. Pharmaceutical compositions suitable for parenteral administration preferably include sterile aqueous preparations of a compound according to formula (I), preferably isotonic with the blood of the intended recipient. These preparations are preferably delivered intravenously, even though the administration can also be carried out subcutaneously, intramuscularly or intradermally in the form of an injection. These preparations can preferably be prepared by mixing the compound with water and rendering the solution obtained sterile and isotonic with the blood. Injectable compositions according to the present invention generally contain from 0.1 to 5% by weight of active compound. Pharmaceutical compositions suitable for rectal administration are preferably present as individual dose suppositories. They can be prepared by mixing a compound according to formula (I) with one or more conventional solid carriers, for example cocoa butter and shaping the resulting mixture. Pharmaceutical compositions suitable for topical application on the skin are preferably present in the form of an ointment, cream, lotion, paste, spray, aerosol, oil. Vehicles that can be used are petroleum jelly, lanolin, polyethylene glycols, alcohols and combinations of two or more of these substances. The active compound is generally present in a concentration of 0.1 to 15% by weight of the composition, for example 0.5 to 2%. Transdermal administration is also possible. Pharmaceutical compositions suitable for transdermal administration may be present as individual patches suitable for long-term contact with the epidermis of the patient. Such patches suitably contain the active compound in an optionally buffered aqueous solution, dissolved and / or dispersed in an adhesive or dispersed in a polymer. A suitable concentration of active compound is from about 1% to 35%, preferably from about 3% to 15%. As a particular possibility, the active compound can be released by electrotransport or iontophoresis, according to what is described, for example, in Pharmaceutical Research, 2 (6): 318 (1986). The invention also relates to a process for the preparation of the compounds of the formula I "(R2 = H), which comprises A) reacting the compounds of the formula II Formula II wherein R 1, R 1 ', R 3 and X and Y have the indicated meanings, and Z is the radical of an activated ester of an organic or inorganic acid, with thioureas of the formula III, which may be present in the Illa, Illb and IIIc tautomeric forms Illa lllb lile wherein R4 and R5 have the indicated meanings, and B) if appropriate convert the compounds of the formula I (R2 = H) into their acid addition salts using organic or inorganic acids or by converting the salts of the compounds of the formula I obtained (R2 = H) in the free basic compounds of the formula I (R2 = H) using organic or inorganic bases. Suitable inorganic acids are, for example: halyhydric acids such as hydrochloric acid and hydrobromic acid, and also sulfuric acid, phosphoric acid and amidosulfonic acid. Organic acids which may be mentioned herein are, for example: Formic acid, acetic acid, benzoic acid, p-toluenesulfonic acid, benzenesulfonic acid, succinic acid, fumaric acid, maleic acid, lactic acid, tartaric acid, citric acid, L-acid ascorbic acid, salicylic acid, isethionic acid, methanesulfonic acid, trifluoromethanesulfonic acid, 1,2-benzisothiazol-3 (2H) -one, 6-methyl-1,2,3-oxathiazin-4 (3H) -one-2, 2- dioxide The compounds of the formula I (R2 = H) may also be present in their tautomeric forms: The compounds of the formula I according to the invention (R2 = H) can also be present in their possible geometric isomeric structures. The alkyl, alkenyl and alkynyl radicals in the substituents R1, R1 ', R2, R3, R4 and R5 can be either straight or branched. Through the tautomeric open-chain form la, the cyclic compounds of the formula I (R2 = H) wherein R4 and R5 are different are in equilibrium with the compounds and positional isomers of the formula Ib (R2 = H) and their acid action salts.

Formula Ib Which of the two cyclic isomers I (R2 = H) or Ib (R2 = H) or their acid addition salts are preferred depends particularly on the different space filling of the substituents R4 and R5 such that the substituent especially smaller is preferably located at position 3 of the thiazolidine ring system. In the compounds according to the invention, only one of the possible isomeric or tautomeric forms of a particular substance is indicated below. The process described above is advantageously carried out in such a way that the compounds II react with the thioureas III in the molar ratio of 1: 1 to 1: 1.5. The reaction is advantageously carried out in an inert solvent, for example, in polar organic solvents such as dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, dioxane, tetrahydrofuran, acetonitrile, nitromethane or diethylene glycol dimethyl ether. Particularly useful solvents, however, are methyl acetate and ethyl acetate, short-chain alcohols such as methanol, ethanol, propanol, isopropanol and lower dialkyl ketones, such as, for example, acetone, butan-2-one or hexan-2-one. Mixtures of the mentioned reaction media can also be used. Mixtures of the solvents mentioned can also be used with solvents that are individually less suitable, for example mixtures of methanol with benzene, ethanol with toluene, methanol with diethyl ether or with tert-butyl methyl ether, ethanol with tetrachloromethane, acetone with chloroform, dichloromethane or 1, 2-dichloroethane, where the more polar solvent in each case must be used in an excess. The components of the reaction can be suspended or dissolved in the respective reaction medium. Fundamentally, the reaction components can also react without solvent, particularly if the respective thiourea has a melting point that is as low as possible. The reaction is carried out only slightly exothermicly and can be carried out at a temperature comprised within a range of -10 ° C to 150 ° C, preferably between 0 ° C and 50 ° C. A degree of temperature between 20 ° C and 40 ° C is especially favorable. The reaction time depends to a large extent on the temperature of the reaction and is between two minutes and 3 days at relatively high and relatively low temperatures, respectively. In the range of favorable temperatures, the reaction time is generally between 5 minutes and 48 hours. Frequently, the compounds I (R2 = H) are separated in the form of their sparingly soluble acid addition salts in the course of the reaction, a suitable precipitating agent is subsequently conveniently added further. These agents are, for example, hydrocarbons such as benzene, toluene, cyclohexane or heptane or tetrachloromethane.; particularly alkyl acetates such as ethyl acetate or N-butyl acetate or dialkyl ethers such as diethyl ether, diisopropyl ether, di-n-butyl ether or tert-butyl methyl ether are especially suitable. If the reaction mixture remains in solution after the end of the reaction, the salts of the compounds I (R2 = H), can be precipitated using one of the mentioned precipitation agents. If appropriate, after the concentration of the reaction solution. In addition, the solution of the reaction mixture can also be advantageously filtered in the solution of one of the mentioned precipitation agents with stirring. Since the reaction of compounds II with thioureas III is carried out virtually quantitatively, the crude products obtained are usually already analytically pure. The treatment of the reaction mixture can also be carried out in such a way that the reaction mixture becomes alkaline with the addition of an organic base such as for example triethylamine or diisobutylamine, or ammonia or morpholine or piperidine or 1,8-diazabicyclo [5.4.0] undec-7-ene, and the crude product of the reaction is purified chromatographically, for example, on the silica gel column, after concentration. Suitable elution means for this purpose are, for example, mixtures of ethyl acetate with methanol, mixtures of dichloromethane with methanol, mixtures of toluene with methanol or ethyl acetate or mixtures of ethyl acetate with hydrocarbons such as heptane. If the purification of the product is carried out in the manner described above, an acid addition product of the formula I (R2 = H) can be obtained from the pure base of the formula I (R2 = H) obtained from this by dissolving or suspending the base in an organic aprotic solvent, such as for example methanol, ethanol, propanol or isopropanol or in an organic aprotic solvent, for example ethyl acetate, diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, tetrahydrofuran , acetone or butan-2-one and then treating is mixed with an at least equimolar amount of an inorganic acid such as hydrochloric acid, dissolved in an inert solvent, for example, diethyl ether or ethanol, or another organic acid or inorganic mentioned above. The compounds of the formula I (R2 = H) can be recrystallized from a suitable, inert solvent, for example acetone, butan-2-one, acetonitrile, nitromethane. Reprecipitation from a solvent such as dimethylformamide, dimethylacetamide, nitromethane, acetonitrile, preferably methane or ethanol is particularly advantageous. Compound of the formula I or Ib wherein R2 = alkyl- (Ci-Ce), cycloalkyl- (dd) or (CH2) -aryl, where n can be = 0-5 and aryl is determined above, can be obtained either aa) allowing the acid addition salts of the formula I or Ib where R2 = H to react in a solvent of the formula R2-OH, wherein R2 has the meaning described above at a temperature between -20 ° C and 120 ° C, preferably at a temperature between -5 ° C and 50 ° C, for 2 hours to 4 days, preferably from 4 hours to 2 days, or ab) by reacting the free bases of the formula I or Ib where R2 is a solvent of the formula R2-OH, where R2 has the meaning described above, with equimolar, substoichiometric or catalytic, preferably catalytic, amounts of an organic or inorganic acid, such as those described above, or with addition of an acid ion exchanger at a temperature of -20 ° C to 120 ° C, preferably at a temperature between -5 ° C and 50 ° C for 2 hours to 4 days, preferably 4 hours to 2 days, or a) carrying out the reactions according to aa) and ab) in an inert aprotic solvent as per example dichloromethane, chloroform, 1,2-dichloroethane, heptane, benzene, toluene, acetonitrile, nitromethane, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diethyl ether, diisopropyl ether, tert-butyl methyl ether, acetone, butan-2-one or lower alkyl acetates such as for example ethyl acetate, by the addition of 1 to 5, preferably from 1.5 to 2 equivalents of a compound of the formula R2-OH or ad) converting compound of the formula I or Ib where R2 = H in its alholates in a polar aprotic solvent, such as, for example, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether , nitromethane, acetonitrile or dimethylformamide, dimethylacetamide, or N-methyl-2-pyrrolidone, with the aid of a base, such as, for example, sodium hydride, lithium diisopropylamine, KOK or potassium carbonate, and then allowing them to react with the addition of an alkylating agent of the formula R2-X, where X = chlorine, bromine, iodine, 0-C (0) -CH3, 0-C (0) -CF3, 0-C (0) -C6H4-4-N02 , 0-S02-CH3, 0-S02-CF3, 0-S02-C6H4-4-CH3, 0-S02-C6H4-4-N02, at a temperature of -20 to 150 ° C, preferably within a range of -15 to 150 ° C, for 10 minutes to 2 days, preferably 20 minutes to 12 hours. Compounds of the formula io Ib where R is different from H which are obtained in accordance with aa) to ad) in accordance with that described above, are either precipitated as a weakly soluble acid addition salt - they are then removed by filtration with suction, washed with a little of the solvent used and dried - or remain in the solution. The purification can be carried out by neutralization of the reaction mixture, after the formation of the ethers of the formula I or Ib where R2 is different from H, has been carried out, with an organic or inorganic base, such as for example triethylamine and concentrating the resulting mixture and then subjecting it to silica gel chromatography. The pure base of the formula I or Ib where R is different from H obtained in this way can be converted into an acid addition salt, in accordance with that described above for compounds of the formula I or Ib where R2 = H. Compound of the formula I or Ib wherein R2 = C (O) -alkyl (Ci-Cß), C (0) -cycloalkyl (dd) or C (0) - (CH2) n-aryl, where aryl may be phenyl, thienyl, pyridyl or furyl and n is according to the above defined, can be obtained either by ba) following the procedure described in aa) -ac), with the difference that instead of a compound R2.0H, a compound R2 is used -C00H wherein R2 is alkyl (Ci-Ce), cycloalkyl (C3-Ce), or (CH2) n-aryl and and aryl have the meanings described above, and employing 1 to 2 equivalents of the compound R2-C00H, preferably 1.5 equivalents of the compound R2-C00H, and without addition of the organic or inorganic catalyst has been described in aa) -ac), but using profitably the inter acid cation exchanger or b) reacting a compound of the formula I or Ib where R2 = H (free base) with a compound of the formula R2-COOH, where R2 = C (0) -alkyl (C? -C6 ), C (0) -cycloalkyl (C3-C5), or C (0) - (CH2) n-aryl and aryl and n are in accordance with that defined above, for example, in the sense of a Mitsunobu reaction ( 0 Mitsunobu, Synthesis 1981, 1) to provide the compound of the formula I or Ib where R2 is not H or be) by reacting a compound of the formula R2-C (0) -Cl, or R2-C (0) -Br, or R2-C (0) -0- (0) -C-R2 with a compound of the formula I or Ib where R2 = H in the sense of an esterification of an alcohol (Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg Thieme Verlag Stuttgart, Volume E5, pages 656-715). The compounds of the formula I or Ib in which R2 is different from H, which are obtained according to ba) a be) in accordance with that described above, are either precipitated in the form of a slightly soluble acid addition salt - they are then removed by suction filtration, washed with a little of the solvent used and dried - or remain in solution. The purification can be effected by neutralization of the reaction mixture after the formation of the esters of the formula I or Ib wherein R2 is not H has been effected, with an organic or inorganic base, such as for example potassium carbonate or triethylamine and concentrating the resulting mixture or then subjecting it to chromatography on silica gel. The pure base of the formula I or Ib wherein R2 is not H obtained can be converted into an acid solution salt, in accordance with that described above for compound of the formula I or Ib wherein R2 = H. In general, the initial substances of formula III are described in the literature (see Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], volume 9, page 384; fourth edition, 1955 or DOS 2640358 (03.16.1978)). In the compounds of formula II, possible radicals of an activated ester Z are, for example, Cl, Br, I, OC (O) -C6H4-4-N02, 0-S02-CH3, 0-S02-CF3, 0 -S02-C6H4-4-CH3, 0-S02-C6H4. They can be obtained in several ways: ca) Diazo ketones of formula VIII Formula VIII can be converted with halyhydric acids into the compounds of formula II (Z = Cl, Br, I; R3 = H). This process and certain compounds of formula II are known from the literature (for example, J. Am. Chem. Soc 80, 2255 (1958); J. Indian Chem. Soc. 42, 115 (1965)), and Additional compounds of formula II can be prepared and reacted accordingly. The diazoketones of the formula VIII can also be converted into the corresponding compounds in the formula II (R3 = H) by processes known from the literature through the hydroxy compounds of the formula IX Formula IX cb) Since the processes mentioned in ca) carry only the compound of the formula II in which R3 remains restricted to hydrogen, compounds of the formula II are advantageously prepared by the reaction of the compounds of the formula X Formula X with a suitable halogenating agent, such as for example with elemental chlorine or bromine, sulfuryl chloride, monochlorourea, N-chlorosuccirtimide, copper (II) bromide, bromo-dioxane complex, N-bromosuccinimide, under known conditions from Literature. The essentially accessible compounds of the formula X are either known or can be prepared by processes known from the literature. Suitable halogenating agents are, for example, elemental chlorine, sulfuryl chloride, monochlorourea, N-chlorosuccinimide, bromo-dioxane complex, N-bromosuccinimide, but particularly elemental bromine or copper (II) bromide. In the case of halogenation with bromine, bromine is advantageously added dropwise, if appropriate diluted in inert solvents, to a solution or suspension of the equimolar amount of the compound of formula X in an inert solvent. Suitable, for example, are halohydrocarbons such as dichloromethane or trichloromethane or 1,2-dichloroethane, but preferably glacial acetic acid or lower alkyl acetate, or mixtures of the aforementioned solvents. The reaction temperature is between 0 ° C and 50 ° C, preferably between 10 ° C and 35 ° C. Halogenations of ketones are catalyzed by acids; therefore it is advantageous if the reaction mixture is treated with catalytic amounts of an acid, for example with hydrobromic acid or after dropwise addition of a little bromine, the reaction mixture is first heated until discoloration of halogen and then brominated additionally. In the bromination of the compounds of formula X with copper (II) bromide it is possible to carry out the reaction analogously to the methods described in J. Org. Chem 29, 3459 (1964) or J. Org. Chem. 40, 1990 (1975). Suitable chlorinating agents are, in particular, sulfuryl chloride, which is reacted in a customary manner with a suspension solution of the compound of the formula X in a solvent, such as for example trichloroethane or tetrachloroethane or an ether, such as, for example, diethyl ether or tert-butyl methyl ether. , in a temperature range between 20 ° C and 80 ° C. The mixture is then treated with ice water and treated as usual. When chlorine is used as a halogenating agent, an HCl gas is introduced first as a catalyst, then, in a temperature range of 0 to 25 ° C, an equivalent amount of chlorine is introduced into the solution of a compound of the formula X in a polar solvent, for example glacial acetic acid or dimethylformamide or N-methyl-2-pyrrolidone. The reaction time is from 2 to 24 hours. The mixture is then treated with ice water and prepared in a customary manner. If N-chlorosuccinimide is used as a chlorination agent in the chlorination reaction, the compounds of formula X advantageously react with 1-2 equivalents of N-chlorosuccinimide at about 50 ° C for 2-12 hours in a polar solvent such as glacial acetic acid after the addition of a catalytic amount of hydrochloric acid. The mixture is then treated with ice water and treated in a conventional manner. The compounds of the formula II can be finally obtained in addition by the preparation of the a-hydroxyketones of the formula XI Formula XI which are either known (Chem. See 83, 390) or which can be prepared according to usual processes, in a manner known per se with the activated derivatives of organic and inorganic acids such as methanesulfonyl chloride, trifluoromethanesulfonyl chloride, ethanesulfonyl chloride, benzenesulfonyl chloride, p-toluenesulfonyl chloride, cionyl bromide, phosphorus trichloride, phosphorus tribromide, phosphorus oxychloride, p-nitrobenzoyl chloride The solution or suspension of the compounds of formula II obtained therefrom The method according to the respective method is conveniently concentrated under reduced pressure and the compounds of the formula II are purified by crystallization from inert solvents such as for example benzene, toluene, tetrachloromethane, dichloromethane, 1,2-dichloroethane, cyclohexane, hexane , heptane Another purification method consists in the chromatography of the reaction mixtures in the gel column silica, heptane, diethyl ether, tert-butyl methyl ether, toluene, ethyl acetate or mixtures thereof which are used as eluents. The compounds of formula II obtained can also be used in the next step without further purification operation. Compound of formula X Formula X wherein R3 is not hydrogen, are accessible differently: da) Compounds of formula X wherein R3 = fluorine can be prepared, for example, by the reaction of compound of formula X wherein R3 = H with a reactant of electrophilic fluorination. Suitable electrophilic fluorination reagents (see also: WE Barnette, J. Am. Chem. Soc. 106, 452-454 (1984)) are, for example, triflate of 1-fluoro-2,4,6-trimethylpyridinium, triflate of 3, 5-dichloro-1-fluoropyridinium, 1-fluoropyridinium triflate, 1-fluoropyridinium tetrafluoroborate, 1-fluoropyridinium heptafluorodiborate, N-fluoro-N-methyl-p-toluenesulfonamide, N-fluoro-N-propyl-p- toluenesulfonamide, N-fluorobenzenesulfonamide, N-fluorobenzenesulfonamide [NFSi], bis (tetrafluoroborate) of l-fluoro-4-hydroxy-l, -diazoniabicyclo [2.2.2]] octane (NFTh). The fluorination reaction is carried out, for example, in such a way that a base, with the aid of which a compound of the formula X (R 3 = H) is converted to the enolate of the compound of the formula X (R 3 = H) is add to a solution or suspension of a compound of the formula X wherein R3 = H in equivalent amounts in a non-polar aprotic solvent, for example benzene, toluene, hexane or heptane or in a polar aprotic solvent, for example tetrahydrofuran, dimethylformamide , acetonitrile, diethylether or tert-butylmethylether or in mixtures thereof. Suitable bases for this reaction are n-butyllithium, sodium or potassium hexamethyldisilazane, sodium hydride, potassium hydride, potassium tert-butoxide, methyllithium, tetra-n-butylammonium hydroxide. A suitable reaction temperature is -78 ° C to 25 ° C. For the solution or suspension of the enolate of the compound of formula X (R3 = H) formed in this manner, one to 2, preferably 1.5 equivalents of one of the aforementioned fluorination agents, dissolved in one of the aforementioned solvents or solvent mixtures mentioned above, preferably dissolved in toluene or dichloromethane, are then added dropwise at a temperature of -78 ° C to + 100 ° C, preferably at a temperature between -50 ° C and + 80 ° C. The sequence of the addition of the reaction components can also be carried out in the reverse order, that is, by adding the solution or suspension of the enolate of the compound of the formula X (R3 = H) dropwise to a solution of the fluorination reagent at the indicated temperatures. Depending on the selected reaction temperature, the reaction ends after 15 minutes at 48 hours. The reaction, particularly with N-fluorobenzenesulfonimide, can also be effected in a manner analogously to E. Differding and H. Ofner, Synlett 187-189 (1991) in such a way that the trimethylsilylene ether of the compound of the formula X, wherein R3 = H, is prepared first (for example, with trimethylsilyl bromide or trimethylsilyl trifluoromethanesulfonate in toluene at a temperature of -78 ° C to 80 ° C with the addition of one equivalent of a base, such as triethylamine) and the fluorination reagent, dissolved in dichloromethane or toluene is then added at room temperature and the reaction mixture is treated after a reaction time of about 12 hours (room temperature). The treatment of the reaction mixture can be carried out in such a way that, after neutralization of an access of the base used, the reaction mixture is concentrated and then treated with a solvent, for example ethyl acetate or heptane and extracted by stirring with a semiconcentrated solution of sodium hydrogencarbonate. The organic phase is concentrated after drying in magnesium sulfate and the product of the reaction can then be recrystallized either from a solvent, for example hexane or heptane for further purification, or alternatively is subjected to chromatographic purification on a column of silica gel with elution with, for example, mixture of dichloromethane with heptane or ethyl acetate with heptane. The reaction with bis (tetrafluoroborate) of l-fluoro-4-hydroxy-1,4-diazoniabicyclo [2.2.2] -octane (NFTh) can also be carried out in such a way that the ketone is used as such without conversion into an enolate or in an enolsilylether. db) Compounds of the formula X wherein R3 = alkyl- (d-C6), or (CH2) n-aryl, wherein n can be = 1-5 and aryl is in accordance with that defined above can be prepared for example , by reacting the compound of formula X, where R3 = H, with a strong base or with an alkylation reagent of the formula R3 = X, where X can be Br, I, 0-C (0) - C6H4-4-N02, 0-S02-CH3, 0-S02-CF3, 0-S02-C6? 4-4-CH3, 0-S02-CeH4. In order to ensure that, in this alkylation, only the desired monoalkylation is carried out, the compounds of the formula X (R3 = H) are previously advantageously converted into a compound, for example, of the formula XII, XIII or XIV .

Formula XII Formula XIII Formula XIV Compounds of the type of formula XII (R3 = H) can be prepared according to F. Henin et al., Tetrahedron, 50, 2849-2864 (1994). Compounds of the type of formula XII (R3 = H) where R '-R "can be - (CH2) 4-, - (CH2) 5-, -CH2-CH2-0-CH2-CH2-, can be prepared, example according to Stork et al., J. Am. Chem. Soc. 85, 207 (1963) Compounds of the formula XIV (R3 = H) are accessible by methods known from the literature, for example PW Hickmott, Chem. Ind. (London), 731 (1974) Compound of the type of formulas XII and XIV (R3 = H) can then react, after conversion in their anion through a strong base, with an alkylating agent of the formula R3-X, where R3 and X are in accordance with that defined above, to provide the desired compounds of formulas XII and XIV (R3 = H) and, after acid hydrolysis of hydrazone (XII) or hydrolysis and decarbonylation of β-ketoesters (XIV), can be converted into the compounds of the formula X according to the invention wherein R3 = H. Compounds of the formula XIII (R3 = H) can be converted to an inert solvent, such as for example trichloromethane or toluene, after addition of a base, such as for example triethylamine, in compounds of the formula X wherein R3 = H with the aid of an alkylating agent of the formula R3-X after acid hydrolysis of the α-alkylated enamine of the formula XIII IR3 = H). Compounds of the formula X wherein R 3 = COOCH 3, COOCH 2 CH 3, COOH, CONH 2, CONHCH 3, CON (CH 3) 2, can be prepared by the compound of the formula XII and the formula XIII according to known methods from the literature by means of of the conversion, for example with Cl-C (O) -0-CH2-CH3. dd) Compounds of the formula X wherein R 3 = Cl can be prepared by methods known in the literature (ME Kuehne, J. Org Chem. 81, 5400-5404 (1959) by reaction of a compound of the formula XIII with chloride of cyanogen) Compound of the formula X wherein R3 = O-alkyl (Ci-Ce) can be prepared by methods known from the literature (Chan Lee et al., Synth Commun. 27, 4085-90 (1997)) starting from compounds of the formula X where R3 = H by reflux treatment of a compound of the formula X (R3 = H) with [hydroxy (p-nitrobenzenesulfonyloxy) iodo] benzene [HNIB] in acetonitrile during 2-6 hours and then by reaction of the resulting intermediate product after removal of the solvent directly with an alcohol of the formula R 3 -OH where R 3 has the meaning defined above, at elevated temperature. df) Compounds of the formula X wherein R 3 = 0 (0) CCH 3 can also be prepared analogously. In this case, the intermediate product described in de) is converted into a compound of formula X wherein R3 = 0 (0) CCH3 in acetic acid with emission of catalytic amounts of silver carbonate. dg) Compounds of the formula X wherein R3 = N3 can be prepared either from the corresponding compounds of the formula X wherein R3 = Cl or Br by nucleophilic substitution with azide (K.Van Sant, MS South; Tetrahedron Lett , 28, 6.0L9 (1987)) or better analogously to T. Patonay and RV Hoffman, J. Org. Chem. 59, 2902-2905 (1994) from enol acetate of compounds X (R3 = H) or from etamines of compounds X (compounds of formula XIII (R3 = H)) through α-tosyloxyketone and subsequent reaction with sodium azide. dh) Compounds of the formula X wherein R3 = alkynyl (-Cβ) can be prepared through 1,3-dicarbonyl compounds of the formula XIV. In a manner analogous to a method known from the literature (M. Ochiai, T. Ito, Y. Takaoka, Y. Masaki, M. Kunishima, S. Tani, Y. Nagao, J. Chem. Soc., Chem. Common. 118-119 (1990)), for this, compounds of the formula XIV (R3 = H). they can be converted first into their enolate anion using a strong base such as, for example, potassium tert-butoxide in tert-butanol or, for example, potassium tert-butoxide in tetrahydrofuran or, for example, sodium hydride in tetrahydrofuran and then reacting with ethynyl (phenyl) iodonium tetrafluoroborate with formation of the compounds of formula XIV wherein R3 = (C2-C6) alkynyl. di) Compounds of the formula X wherein R3 = S02-alkyl (C? ~ C6), S02-phenyl (CH2) n, SO-alkyl (C? -C6), S02-phenyl (CH2) n, S-alkyl (Ci-Cß), S-phenyl (CH2) n, where n can be = 0 -3, can be prepared by reaction of the enolate anion of the compounds of the formula X, wherein R3 = H, generated through a strong base such as, for example, lithium diisopropanylamide in a mixture of solvents such as, for example, hexane / pyridine according to methods known in the literature, with appropriate diphenyl disulfide, di (aralkyl) or dialkyl at low temperatures. The compounds of formula X obtained in this manner, wherein R3 = S-alkyl (Ci-Ce), or S-phenyl (CH2) n wherein n = 0-3, can be originally processed with persellenic acid to provide the sulphides corresponding (R3 = SO-alkyl (Ci-Ce), SO-phenyl (CH2) n) (J. Drabowicz, M. Mikolaj czk; Synthesis 1978, 758) and with a solution of 30% hydrogen peroxide or by reaction with m-peroxybenzoic acid in dichloromethane to provide the correct sulfones (R3 = S02-alkyl (Ci-d), S02- (CH2) n-phenyl). Compounds of the formula X (R3 = H), which serve as starting materials for the preparation of the compounds of the formula II wherein R3 = H, F, CN, N3, O-alkyl (C? -C6), alkyl ( C? -C6), (CH2) n_aryl, where n can be = 0-5 and aryl can be phenyl, thienyl, pyridyl or furyl, alkyl (Ci-Ce), S02-alkyl (C? -C6), S02- (CH2) n-phenyl, SO-alkyl (Ci-Ce), SO- (CH2) n-phenyl, S-alkyl (C? -C6), S- (CH2) n-phenyl, where n could be = 0 - 3, C (0) OCH3, C (0) OCH2CH3, CIO) OH, C (0) NH2, C (0) NHCH3, C (0) N (CH3) 2, 0 (0) CCH3 and Z have the meanings mentioned above, are commercially available or can be obtained analogously to processes known from the literature (Scheme 1): Scheme 1 Ri ea) Compounds of the formula XV wherein R 1, R 1 ', X and Y have the meanings mentioned at the beginning, and wherein W is a carbonyl activation group, for example halogen, for example Cl or Br or OR "or 0 -C (0) -R ", where R" = alkyl, for example, CH3, or aryl, for example phenyl, can be subjected to ring closure with protonic acids or Lewis acids to provide the corresponding cyclized compounds of the formula Xa according to methods known in the literature, for example Houben-Weyl, Methoden de Organischen Chemie [Methods of Organic Chemistry], T ieme Verlag Stuttgart, 1973, Volume VII / 2a, page 111 et seq., Feb) Compounds of the formulas X or Xa, wherein R1 and / or R1 '= S-alkyl (C6C6), S-phenyl, SO-alkyl (Ci-Ce), SO-phenyl, S02-alkyl (d-Ce), S02-phenyl, S-phenyl (CH2) n, SO-phenyl (CH2) n, S02-phenyl (CH2) n, where n can be = 0-6, S02-NH2, S02NH (C? -d) -alkyl , S02N [(C? -C6) -alkyl] 2, can be prepared in accordance with methods known from the literature (Houben-Weyl, Methoden der Organischen Chemie) [Methods of Organic Chemistry] volume XI / 1, page 422 et seq. and 475 et seq., Thieme Verlag Stuttgart) by subjecting appropriately substituted compounds to the formula X or of the formula Xa, where R1 and / or R1 '= N02, at a reduction to the amines of X or of the formula Xa, where R1 and / or R1' = NH2, using, for example, nickel of Raney and hydrogen in a solvent, for example ethanol or glacial acetic acid, either by using zinc in glacial acetic acid, or by using tin or tin (II) chloride in hydrochloric acid and then diazotizing by reaction with sodium nitrite in acid hydrochloric and further converting with CuCl2 and S02 into glacial acetic acid to provide the correspondingly substituted sulfonyl chloride. These compounds can be converted reductively into the alkaline medium in accordance with standard conditions in the corresponding sulfinic acids which, in turn, are then further processed according to methods known from the literature to provide compounds of the formula X or of the formula Xa, wherein R1 and / or R1 '= S-alkyl (C6C6), S-phenyl, SO-alkyl (Ci-Ce), SO-phenyl, S02-alkyl (Ci-Ce), S02-phenyl, S-phenyl (CH2) n, SO-phenyl (CH2) n, S02-phenyl (CH2) n, where n can be = 0-6, S02-NH2, S02NH (C? -C6) -alkyl , S02N [(C? -C6) -alkyl] 2. Compounds of the formula X or of the formula Xa, where R1 and / or R1 '= O-alkyl (C? -C6), 0-CH2-CF3 , 0-CH2-CF2-CF3, O-C4-C6 alkyl, - wherein in the alkyl radicals one or more or all of the hydrogen atoms may be replaced by fluorine or a hydrogen may be replaced by OH, 0C (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2, O-phenyl (CH2) n, where n = 0-6, S-alkyl (Ci-d), S-phenyl, S-phenyl (CH2) n, where n can be = 0-6, are accessible in accordance with standard methods from the compounds formula X or of the formula Xa, wherein R1 and / or R1 '= F or Br, by nucleophilic substitution with compounds of the formula R1-M and / or R1'-M, where R1 and R1' have the meanings mentioned above and M is an alkali metal atom, such as for example Na, or a tetrasubstituted nitrogen atom, such as (n-Bu) 4N. For this, for example, a compound of the formula X or of the formula Xa, wherein R1 and / or R1 '= F, reacts profitably at a temperature of 50 to 150 ° C in a polar aprotic solvent, example, dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone or dimethyl sulfoxide with a compound of the formula R1-H or R1'-H, where R1 and R1 'are in accordance with that defined above , with addition of a base such as for example potassium or sodium carbonate, sodium hydride, potassium hexamethyldisilazane, potassium or sodium hydroxide, cesium carbonate or tetra-n-butylammonium hydroxide and then treated in a customary manner. Such compounds can also be obtained by the reaction of compounds of formula X or formula Xa, wherein R1 and / or R1 '= Br, under conditions of phase transfer catalysis (EV Dehmolow, SS Dehmolow, Phase Transfer Catalysis, 2nd edition, ED., Verlag Chemie, Weinheim, 1983) with compounds of the formula R1 -H and / or Rl'-H, for example, a catalyst such as, for example, Aliquat 336 in a mixture of toluene with a 505 aqueous solution of sodium hydroxide or with 15-crown-5 in toluene with an aqueous solution 50% sodium hydroxide for about 2 hours and 7 afterwards are treated in the usual way (AJ Serio Duggan, EJJ Grabowski, WK Russ: Synthesis 573-5 (1980); A. Ohta, Y. Iwasaki, Y. Akita: Synthesis 828-9 (1982); W. Chin-Hsieh, L. Xiang-Te, C. Xiao-Hun: Synthesis 858-61 (1982); H. Alsaidi, RR. Gallo, J. Metzger: Synthesis 921-4 (1980)). After the usual treatment, the compounds of the formula X or of the formula Xa, wherein R1 and / or R1 '= O-alkyl (Ci-d), 0-CH2-CF3, 0-CH2-CF2-CF3, O- alkyl (C4-C6), where in the alkyl radicals one or several or all of the hydrogen atoms may be replaced by fluorine or a hydrogen atom may be replaced by OH, OC (0) CH3, 0-CH2- Ph, NH2 or N (C00CH2Ph) 2, O-phenyl (CH2) n, where n can be = 0-6, S-alkyl (C? -C6), S-phenyl, S-phenyl (CH2) n, where n can be = 0 - 6, they can be isolated in this way. Compounds of formulas X or Xa, where R1 and / or R1 'is CN, can be obtained in accordance with standard 8L methods. Friedman, H. Shechter, J. Org. Chem. 26, 2522-24 (1961) from, for example, compounds of the formulas X or Xa, wherein R1 and / or R1 'is Cl or Br, by nucleophilic replacement with a metal cyanide such as NaCN , KCN, Cu- (I) -CN. The solvent used for this purpose is preferably an aprotic, polar medium, such as, for example, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone or dimethyl sulfoxide. A suitable reaction temperature is 150 to 200 ° C. eq) Compounds of the formulas XV and Xa, wherein R1 and / or R1 'are an optionally substituted aryl or heteroaryl, can be prepared from the corresponding compounds of formulas XV and Xa, wherein R1 and / or R1 'is bromine, iodine or trifluoromethanesulfonyloxy, according to methods known from the literature. Analogously to N.

Miyaura and A. Suzuki, Chem. Rev. 95, 2457-83 (1995) or T.

Oh-e, N. Miyaura and A. Suzuki, J. Org. Chem. 58, 2201-08 (1993), such compounds can be obtained starting from bromo- or iodo (hetero) aryls or from (hetero) aryl triflates of the formula XV or of the formula Xa, wherein R1 and / or R1 ' is bromine, iodine, trifluoromethanesulfonyloxy, by reaction with arylboronic acids or arylboron esters or dialkyls of the formula Rl-B or Rl'B, wherein R1 and / or R1 'may be an optionally substituted aryl radical such as, for example, phenyl, thienyl , pyridyl or furyl and B is a boron-containing radical such as for example B (OH) 2, B (OCH 3) 2, B (0- (CH 2) 3-0), B (0C (CH 3) 2-C (CH 3 ) 2-0) or B (CH2-CH3) 2, in such a way that the coupling reaction is carried out at a temperature between 20 and 150 ° C with the addition of an organic base such as triethylamine or an inorganic base cone for example sodium hydroxide, sodium carbonate, sodium hydrocarbonate, potassium carbonate, potassium phosphate, barium hydroxide, cesium fluoride or tetrahydrate fluoride utilamonium in a solvent mixture for example toluene and water or acetone and water or dimethoxyethane and water or in solvents such as toluene, benzene, dimethoxyethane, tetrahydrofuran, dioxane, acetone or dimethylformamide with the addition of a palladium catalyst. Suitable palladium catalysts are, for example: Pd (OAc) 2, Pd (PPh3) 4, PdCl2 (PPh3) 2, palladium chloride (II) complex - [1,1'-bis (diphenylphosphino) ferrocene] -chloride methylene, Pd [P (2-methoxyphenyl)] 4 or Pd (DBA) 2 / [(MeO) 3C6H2] PPh2 ([DBA = dibenzylideneacetone]). ed) In addition, the compounds of formulas XV and Xa, wherein R1 and / or R1 'are / is an optionally substituted aryl or heteroaryl radical, can also be prepared from the corresponding compounds of formulas XV and Xa, wherein R1 and / or R1 'are / is a boron-containing radical such as for example B (OCH3) 2 or B (OC (CH3) 2-C (CH3) 2-0). They are prepared analagously to T. Ishiyama et al., J. Org. Chem. 60, 7508-10 (1995) or M. Murata et al., J. Org. Chem. 62, 6458-59 (1997) from the compounds of formulas XV and Xa, wherein Rl and / or R 1 'is bromine or iodine, by reaction with the pinacol ester of diboronic acid [(MeC202) BB (02C2Me4)] or by reaction with 4, 4, 5, 5-tetramethyl-1,3,2-dioxoborlane. employed are preferably dimethyl sulfoxide, dimethylformamide, dioxane or toluene or mixtures thereof The reaction temperature is about 80 to 100 ° C. A weak base such as for example potassium acetate and a palladium catalyst such as for example palladium chloride (II) complex - [1,1'-bis (diphenylphosphino) ferrocene] -methylene chloride or PdCl2 (PPh3) 2 are further added to the reaction mixture. The compounds of formulas XV and Xa obtained from this form, where R1 and / or R1 'is a boron-containing radical such as for example B (0CH3) 2 or B (OC (CH3) 2-C (CH3) 2-0), can then be coupled in accordance d as described in ec) with a compound R1-Br, R1-I, R1-OTf to provide compounds of formulas XA and Xa, wherein R1 and / or R1 'are / is an optionally substituted aryl or heteroaryl radical. Compounds of the formulas XV and Xa, wherein R1 and / or R1 'are / is a rac.ical containing boron such as for example B (OH) 2, B (OCH3) 2, B (0- (CH2) 3- 0), B (OC (CH3) 2-C (CH3) 2-0) or B (CH2-CH3) 2 can also be prepared in another way from compounds of formula XV or formula Xa, in where R1 and / or R1 'are / is bromine or iodine. For this purpose, the aryl or heteroaryl halides of the formula XV or Xa, possibly after protection as for example an acetal, of a carbonyl function that may be present, with lithium butyllithium or diisopropylamide in tetrahydrofuran at -78 ° C, they are converted according to known methods from the literature (for example, M. Ishikura et al., Chem. Pharm. Bull. 33, 4755-63 (1985)) into the corresponding lithium compounds which, on the other hand, they then react with a boric acid ester such as, for example, trimethyl borate or an alkoxydialkylborane, such as, for example, methoxydiethylborane to provide a boron-containing compound of the formula XV or Xa. ee) A further method for obtaining the compounds of the formula Xa wherein R1 and / or R1 'are / is an optionally substituted aryl or heteroaryl radical, consists of the reaction of compounds of the formula XVI, wherein R1 has the meanings mentioned at the beginning, and Sn (alkyl) 3 is, for example, Sn (n.-butyl) 3, in the sense of a Stille coupling in accordance with methods known from the literature such as for example those described in JK Stille, Angewandte Chemie, 98, 504-519 (1986), in TN Mitchell, Synthesis 803-815 (1992) or in T. Gan et al., Tetrahedron Lett. 38, 8453-56 (1997), with a compound Rl'-Br or Rl'-I, where Rl 'is an optionally substituted aryl or heteroaryl radical, with palladium catalysis such as, for example, with Pd (PPh3) 4, PdCl2 (PPh3) 2, PdCl2 (PNC) 2 or PdCl2 (CH3CN) 2 in a solvent with, for example, tetrahydrofuran, toluene or dimethylformamide at temperatures between 20 and 150 ° C. The organotin compounds of formula XVI meanwhile they are accessible, for example, from brominated or ring iodinated precursors by reaction with bistrialkyltin compounds, for example, bistributyltin (Bu3SnSnBu3), in accordance with processes known from the literature (JK Stille, Angewandte Chemie, 98, 504 -519 (1986); T. Gan et al., Tetrahedron Lett. 38, 8453-56 (1997)). In this process, a palladium catalyst such as Pd (PPh3) 4 is added. The solvent used can be, for example, toluene; In addition, the organotin compounds of the formula XVI, where Sn (alkyl) 3 can be, for example, Sn (CH 3) 3, can be obtained analogously to the methods known from the literature (M. Gielen et al., Rev. Silicon Germanium Tin Lead Compd., 3, 9 (1977); M. Gielen, Rev. Silicon Germanium Tin Lead Comp., 5, 6 (1981)) by reaction of the corresponding ring brominated precursor with sodium trimethylsenate at a temperature of about 0 ° C. ef) Similarly, compounds of the formula Xa wherein R 1 and / or R 1 'are / is an optionally substituted aryl or heteroaryl radical, can be obtained in such a way that compounds of the formula Xa, wherein R 1 and / or R 1' are / is bromine or iodine, react with aryl or trialkyls of heteroaryltin of the formula R1-Sn (alkyl) 3 or R1'-Sn (alkyl) 3, where R1 and R1 'are an optionally substituted aryl or heteroaryl radical, in the conditions described in ee). eg) Compounds of the formula Xa in which R1 and / or R1 'are / is alkynyl (C2-d) or alkenyl (C2-d) can be obtained by methods known in the literature, in accordance with that described in ec) and ee), by reaction catalyzed with palladium for example trimethylsilylacetylene or alkynes (K. Sonagashira et al., Tetrahedron Lett. 4467 (1975); S. Takahashi et al., Synthesis 627 (1980)), alkynylzin bromides (E. Negishi et al., J. Org. Chem. 62, 8957-60 (1997)) or trialkyltin alkyls, trialkyltin vinyl or allyl compounds, 1-alkenylboron compounds or vinyl compounds (A. Hassner et al. al., J. Org. Chem. 49, 2546 (1984)) with compounds of formula Xa wherein R 1 and / or R 1 'are / is bromine, iodine or OTf. The solution or suspensions of the compounds of the formula II obtained in this manner according to the respective method is evaporated under reduced pressure and the compounds of the formula II are purified by crystallization from inert solvents such as benzene, toluene, tetrachloromethane. , dichloromethane, 1,2-dichloroethane, cyclohexane, pentane, heptane. Advantageously, the compounds of the formula II obtained in this way can also react with 1 to 1.5 times the amount of a thiourea of the formula III in the manner described in a) above in a suitable inert solvent without further purification operations. For the reaction of the compounds of formula IV described in process b), the reaction is carried out in a solvent using the known compounds of formula V. Particularly suitable solvents of this type are lower alcohols having from 1 to 4 carbon atoms. carbon and lower alkyl esters of acetic acid having from 1 to 4 carbon atoms in the alkyl portion, for example, methyl acetate, and ethyl acetate. In general, the reactions are carried out at a temperature comprised within a range between 0 ° C and 60 ° C, preferably between 15 ° C and 35 ° C, the time of the reaction being between 5 and 60 hours. The compounds of the formula I can be recrystallized from a suitable inert solvent such as, for example, acetone, methyl ethyl ketone, acetonitrile, nitromethane. However, reprecipitation from a solvent is especially advantageous, as for example in dimethylformamide, dimethylacetamide, nitromethane, acetonitrile, methanol, ethanol, isopropanol. The free bases of the formula I can also be beneficially purified by chromatography on silica gel. Suitable eluents are mixtures of dichloromethane with methanol, ethyl acetate with neptan, ethyl acetate with methanol. The compounds of the formula I can be optionally converted to their salts using an acid of the formula H-Z. In this process, compounds I can be introduced into pure acids at temperatures between 0 ° and 40 ° C if they are in the liquid state or if they have a melting point not significantly higher than 40 ° C. Profitably, however, The reaction is carried out in a solvent such as water or in an organic solvent, for example dioxane, tetrahydrofuran, diethyl ether, diisopropyl ether, tert-butyl methyl ether, a lower alkyl acetate having from 1 to 4 carbon atoms in the alkyl, acetonitrile, nitromethane, acetone, methyl ethyl ketone or a lower alcohol having 1 to 4 carbon atoms. In this case, 1-1.5 moles of the H-Z acid per mole of the compounds I can also be used; however, larger amounts of acid can also be employed. In a practical way, the reaction is carried out at temperatures between 0 and 40 ° C, preferably between 10 and 25 ° C. When working in an aqueous solution, after the addition of HZ acids, an immediate dissolution of the compounds of the formula I, and only a low deposit of the corresponding acid addition compounds. Conveniently, the salts according to the present invention are isolated when a solution is obtained by careful evaporation of the water, preferably by lyophilization. When working in organic solvents, the sparingly soluble acid addition salts are frequently precipitated after the addition of the respective H-Z acids. Otherwise, the acid addition compounds are precipitated, if appropriate after preconcentration, using one of the precipitation agents mentioned. The acid addition products are also obtained in an extremely high degree of purity, occasionally in the form of viscous oils or amorphous glass products. These amorphous products can be crystallized by treatment with an organic solvent in a temperature range of 40 ° to 80 ° C. The organic solvents suitable for this purpose are, in particular, dialkyl ketones, such as acetone or methyl ethyl ketone, lower dialkyl ethers and acetonitrile, nitromethane and, where appropriate, alternatively lower alcohols. The acid addition products can be deprotonated or treated with bases to provide the compounds of formula I. Possible bases are, for example, solutions of inorganic hydroxides such as for example lithium, sodium, potassium, calcium or barium hydroxide, carbonates or hydrogencarbonates, such as, for example, sodium or potassium carbonate, sodium or potassium hydrogencarbonate, ammonia and amines, e.g., for example, triethylamine, diisopropylamine, dicyclohexylamine, piperidine, morpholine, methyldicyclohexylamine. When working in an aqueous medium, the poorly soluble free basic compounds I are frequently precipitated and can be removed by filtration or extraction with an organic solvent, preferably with ethyl acetate, and isolated. Suitable organic reaction media are in particular lower alcohols having from 1 to 4 carbon atoms, preferably methanol, ethanol and isopropanol; however, ethyl acetate, diethyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, dimethylformamide may also be employed. The reaction is carried out at a temperature of -35 ° to 60 ° C, preferably 0 ° to 25 ° C. If a water-miscible organic solvent is used, the free bases of the formula I are precipitated by the addition of water, if appropriate after pre-concentration of the reaction mixture. When a water immiscible solvent is used, the reaction mixture is washed with water after the reaction and the organic solvent is evaporated.

The examples that we present below serve to illustrate the invention, but not to limit it. The measured melting or decomposition points (p.f.) were not corrected and generally depend on the heating rate. Table 1: examples Formula I Example Rl; Rl R2 R3 R4 R5 X Salt p.f. [° C] The compounds of the formula I are distinguished by favorable effects on the metabolism of the lipids; particularly, they are suitable as anorectic agents for weight loss. The compounds can be used alone or in combination with additional thinning agents (in accordance with the description, for example, in the chapter 01 of the Red List). The compounds are also suitable for the prophylaxis and treatment of type II diabetes. The efficacy of the compounds was tested as follows: Biological test model: The anorexic action was tested in male NMRI mice. After removing the feed for 24 hours, the test preparation was administered through a stomach tube. The animals, separated and with free access to water, received evaporated milk 30 minutes after the administration of the preparation. The consumption of evaporated milk was determined every half hour for 7 hours and the general condition of the animals was observed. The milk consumption measured was compared with the consumption of the untreated control animals. Table 2: Anorexic action, measured as the reduction in cumulative milk consumption of treated animals compared to untreated animals. Compound / oral dose Number of Reduction number example [mg / kg] animal / animals / consumption con sumption cumulative accumulated high cumulated in ol Formula I untreated control treaties N / tml] N / [ml] Compound of 50 6 / 1.62 12 / 2.61 38 comparison: Y = direct link X = CH2; Rl = Rl '= R2 = R3 = H; R4 = R5 = CH3; salt of HBr Example A27 50 5 / 0.44 5 / 4.04 89 Example A28 50 5 / 0.06 5 / 4.00 98 Example A35 50 5 / 2.46 5 / 5.50 55 Example A39 50 5 / 1.48 5 / 5.42 73 Example A41 50 5 / 0.84 5 / 3.12 73 Example A42 50 5 / 0.60 5 / 2.94 80 Example A45 50 5 / 0.06 5 / 2.78 98 Example A50 50 5 / 1.56 4 / 3.53 56 Example Bl (rae) 50 5 / 0.06 5 / 2.94 98 Example Bl (-) 50 5 / 0.08 5 / 3.40 98 Example B2 (rae) 50 5 / 0.06 5 / 3.40 98 Example B2 (+) 50 10 / 1.37 10 / 4.56 70 Example B2 (-) 50 10 / 0.22 10 / 4.80 95 Example C6 50 5 / 0.42 5 / 3.64 88 Example D29 50 5 / 1.84 5 / 4.74 61 Example E2 50 5 / 0.34 5 / 2.78 88 It can be inferred from the table that the compounds of the formula I have a very good anorexic action. The anorexic action is also markedly improved compared to the comparison example.

The preparation of some examples is described in detail below; the other compounds of the formula I were obtained analogously: Example 1 (compound A4): 5-methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8-tetrahydroindeno- [1,2-d] thiazole -3a-ol a) indan-l-one-6-sulfonyl chloride 5.2 g of sodium nitrite in 11 ml of water were added dropwise at a temperature of 0-5 ° C to a suspension of 10.7 g of 6 -aminoindan-1-one obtainable commercially in 100 ml of semi-concentrated hydrochloric acid and the mixture is stirred for 15 minutes. The resulting solution is added dropwise to a mixture of 6.4 g of CuCl2 x 2H20 in 20 ml of water and 195 nal of a saturated solution of So2 in glacial acetic acid. After the suspension of the nitrogen emission, the mixture is stirred at room temperature for 1 hour. By adding 400 ml of water, crystallization of the desired product (indan-l-one-6-sulfonyl chloride) is achieved, which is removed by suction filtration and washed with a little cold water. It has a melting point of 75 ° C. b) indan-l-one-6-sulfinic acid: 2.1 g of solid NaOH and 18.1 g of NaHS03 are dissolved in 53 ml of water. 2 N NaOH is added simultaneously and 8 g of indan-l-one-6-sulfonyl chloride are introduced in portions in such a way that the pH remains at 7-7.2. The temperature rises in the course of this to about 35 ° C. The mixture is stirred at room temperature for 2 hours, carefully acidified with concentrated hydrochloric acid and concentrated to dryness, the residue is extracted twice by boiling with approximately 200 ml of methanol and the filtrate is concentrated again. The residue is triturated with a little acetone, removed by filtration with suction and dried in vacuum. Indan-l-one-6-sulfinic acid is obtained, which decomposes at a temperature of 275 ° C. c) 6-methanesulfonyl-indan-l-one: 0.75 g of sodium is dissolved in 75 ml of anhydrous methanol. 5.9 g of indan-l-one-6-sulfinic acid are added in portions and the mixture is stirred at room temperature for 30 minutes. 7.5 ml of methyl iodide is then added and the mixture is stirred at reflux temperature for 4 hours. After standing overnight, it is concentrated, the residue is extracted by stirring with water and CH2C12, the organic phase is dried and concentrated, and the residue is crystallized using diisopropyl ether. After removal by filtration with suction and drying, 6-methanesulfonylindan-1-one with a melting point of 155 ° C is obtained. D) 2-bromo-6-methanesulfonylindan-1-one: 3.15 g of 6-7 is suspended. methanesulfonylindan-1-one in 50 ml of glacial acetic acid and treated with 0.4 ml of a 48% HBr solution. 0.92 ml of bromine in 10 ml of glacial acetic acid is added at room temperature and the mixture is stirred for 2 hours. It is emptied into ice, and the precipitate formed is removed by filtration with suction and washed with cold water. The product is purified by column chromatography on SiO2, using dichloromethane. A derivative of dibromo is obtained as the preliminary fraction and 2-bromo-6-methanesulfonylindan-1-one with a melting point of 120 ° C as the main product. e) 5-Methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8-tetrahydroindeno [1,2-d] thiazole-3a-ol: 1.45 g of 2-bromo-6-methanesulfonylindan-l is dissolved -one in 15 ml of acetone and treated with stirring with 1.25 g of N, N'-diphenylthiourea in 25 ml of acetone. The hydrobromide of 5-methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8-tetrahydroindeno [1,2-d] thiazole-3a-ol is crystallized from the clear solution after about 2 hours. After standing overnight, it is removed by filtration with suction and washed with a little acetone. 1.7 g of hydrobromide (melting point 247 ° C) is dissolved in 10 ml of methanol and treated with 0.8 ml of triethylamine. After 15 minutes, 150 ml of water are added and the mixture is stirred for 30 minutes with ice cooling. The formed product is removed by filtration with suction and washed with a little cold water. There is obtained 5-methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8-tetrahydroindeno [1,2-d] thiazole-3a-ol with a melting point of 172 ° C. Example 2 (compound A9 ): 3-ethyl-2-ethylimino-5- (propan-1-sulfonyl) -2, 3, 8, 8a-tetrahydroindeno- [1, 2-d] thiazol-3a-ol a) 6- (propan-l) --sulfonyl) indan-1-one: 0.25 g of sodium is dissolved in 50 ml of anhydrous methanol. 1.96 g of indan-l-one-6-sulfinic acid (see above) is added in portions and the mixture is stirred for 30 minutes at room temperature. Then 1.87 g of 1-iodopropane is added and the mixture is stirred for 4 hours at reflux temperature. To finish the reaction, the mixture is concentrated in vacuo, treated with 5 ml of iodopropane and 10 ml of toluene and heated at reflux for 2 hours. After it is concentrated, the residue is extracted by stirring with water and CH2C12, the organic phase is dried and concentrated and the residue is purified by column filtration (Si02).; cyclohexane / ethyl acetate = 2/1). 6- (propan-1-sulfonyl) indan-1-one with a melting point of 100 ° C is obtained. B) 2-bromo-6- (propan-1-sulfonyl) indan-1-one: The reaction of 6- (propan-1-sulfonyl) indan-1-one to give 2-bromo-6- (propan-1-sulfonyl) indan-1-one is carried out analogously to the preparation of 2-bromo-6-methanesulfonylindan -1-ona. The crude product can be purified by crystallization and washed with petroleum ether with a low boiling point. 2-bromo-6- (propan-1-sulfonyl) indan-1-one with a melting point of 87-89 ° C is obtained. C) 3-ethyl-2-ethylimino-5- (propan-1-sulfonyl) - 2, 3, 8, 8a-tetrahydroindeno [1,2-d] thiazole-3a-ol: 951 mg of. 2-bromo-6- (propane-1-sulfonyl) indan-1-one are dissolved in 20 ml of acetone and treated with 528 mg of N, N'-diethylurea in 10 ml of acetone with stirring. After about 10 minutes, the hydrobromide of 3-ethyl-2-ethylimino-5- (propan-1-sulfonyl) -2, 3, 8, 8a-tetrahydroindeno [1,2-d] thiazole-3a-ol crystallizes . The mixture is stirred at room temperature for an additional hour and the precipitate is removed by suction filtration and washed with a little acetone. After drying, the hydrobromide of 3-ethyl-2-ethylimino-5- (propan-1-sulfonyl) -2, 3, 8, 8a-tetrahydroindeno [1, 2-d] thiazol-3a-ol point of 146 ° C fusion is obtained. It is dissolved in 10 ml of methanol and treated with 0.4 ml of triethylamine. After 15 minutes, 50: .t. Of water is added and the mixture is stirred in an ice bath for 1 hour. The crystallizate formed is removed by suction filtration, washed with water and purified by column filtration (SiO2, ethyl acetate / methanol 3/1). There is obtained 3-ethyl-2-ethylimino-5 (propan-1-sulfonyl) -2, 3, 8, 8a-tetrahydroindeno [1,2-d] -thiazol-3a-ol with a melting point of 136c C. The compounds of examples Al, A2 (use of imidazolin-2-thione), A3 (use of 5-aminoindan-1-one), A5, A6, A7, A8, AlO, A17 (use of 4-amino- indan-l-ona), A47, A48 (use of 5-chloro-6-nitroindan-1-one) were prepared analogously. , Example 3 (compound A21) 3-Ethyl-2-ethylimino-6-phenyl-2, 3, 8, 8a-tetrahydroindeno [1, 2-d] thiazol-3a-ol hydrobromide: a) 5-phenylindan-1 -one: 4.22 g of 5-bromoindan-1-one, 2.44 g of phenylboronic acid and 4.24 g of sodium carbonate are suspended in a mixture of 100 ml of toluene with 20 ml of ethanol and 20 ml of water. After the addition of 450 mg of palladium (II) acetate and 1.05 g of triphenylphosphine, the mixture is heated under reflux for 5 hours. The ethanol part in the reaction mixture is then removed by vacuum distillation and the reaction mixture is treated with 50 ml of a 0.5 N sodium hydroxide solution and stirred at room temperature for 15 minutes. The organic phase is removed and the aqueous part is further extracted twice by stirring with toluene. The combined organic phases are washed with water, then with a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue is stirred with n-heptane, removed by filtration with suction, washed with n-pentane and dried in vacuo at room temperature. 5-phenylindan-1-one with a melting point of 75 ° C is obtained. b) 2-bromo-5-phenylindan-1-one: 3.19 g of 5-phenylindan-1-one are dissolved in 25 ml of glacial acetic acid. 10 μl of a 48% solution of HBr in glacial acetic acid is added and a solution of 0.592 ml of bromine in 5 ml of glacial acetic acid is added dropwise with stirring at room temperature within 15 minutes. The reaction mixture is stirred at room temperature for an additional 2 hours before adding 0.057 ml of bromine, stirred for an additional hour, and the reaction mixture is then added to ice water (15 g of water, 45 g of water). ice, 50 mg of sodium hydrogencarbonate). The deposited precipitate is removed by suction filtration and subjected to chromatography on silica gel using toluene / ethyl acetate 10/1. 2-bromo-5-phenyl-indan-1-one is obtained with a melting point of 99-100 ° C. c) 3-ethyl-2-ethylimino-6-phenyl-2,3,8,8-tetrahydroindene hydrobromide [1] , 2-d] -thiazole-3a-ol 718 mg of 2-bromo-5-phenylindan-1-one are dissolved in 20 ml of dry acetone. A solution of 397 mg of N, N '-diethylthiourea in 10 ml of dry acetone is added dropwise to this solution at a temperature of 5 ° C within 5 minutes. The reaction mixture is stirred at room temperature for 2 hours, and the precipitate is then removed by filtration with suction and washing with acetone to obtain 3-ethyl-2-ethylimino-6-phenyl-2,3-hydrobromide. 8, 8a-tetrahydroindeno [1,2-d] thiazole-3a-ol with a melting point of 140-141 ° C (decomposition). Starting from 5-bromoindan-1-one, the following were prepared analogously: compounds A22, A24, A25, A26, A29, A30, A31, A32, A34, A36, A37, A38 Example 4 (compound A39): 3-Methyl-2-methylimino-7- (4-trifluoromethylphenyl) -hydrobromide 2, 3, 8, 8a-tetrahydroindeno [1,2-d] thiazol-3a-ol a) 4- (4-trifluoromethylphenyl) indan-1-one: 6.33 g of 4-bromoindan-l-one, 5.7 g of 4- (trifluoromethyl) -phenylboronic acid and 6.36 g of sodium carbonate are suspended in a mixture of 100 ml of toluene with 20 ml of ethanol and 20 ml of water with stirring, 320 mg of palladium acetate (II) are added. ) and 787 mg of triphenylphosphine under an atmosphere of protective gas ( n), and the mixture is stirred under reflux for 3 hours. After an additional hour, 1.45 g of 4- (trifluoromethyl) phenylboronic acid and 320 mg of palladium (II) acetate are added again and the mixture is boiled for an additional 2 hours. The ethanol is removed from the reaction mixture cooled by vacuum distillation, and the residue is treated with 50 ml of a 0.5 N sodium hydroxide solution, stirred and filtered. The organic phase of the filtrate is washed several times with 50 ml of water in each case and finally with 50 ml of a saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel using n-heptane / ethyl acetate 3/1 and 4- (4-trifluoromethylphenyl) indan-1-one with a melting point of 81 ° C is obtained. B) 2- bromo-4- (4-trifluoromethylphenyl) indan-1-one: 2.76 g of 4- (4-trifluoromethylphenyl) indan-1-one are dissolved in 20 ml of glacial acetic acid. 10 μl of a 43% solution of hydrobromic acid in glacial acetic acid is added and a solution of 0.516 ml of bromine in 5 ml of glacial acetic acid is then slowly added dropwise. The reaction mixture is stirred at room temperature for 3 hours and then poured into a mixture of 100 ml of water with 100 g of ice and 100 mg of sodium hydrogencarbonate. The aqueous suspension is extracted by stirring with dichloromethane, and the organic phase is washed three times with water, dried over magnesium sulfate, concentrated and chromatographed on silica gel using dichloromethane / n-heptane 3/1. There is obtained 2-bromo-4- (4-trifluoromethylphenyl) indan-1-one with a melting point of 94-97 ° C. C) 3-Methyl-2-methylimino-7- (4-trifluoromethyl enyl) hydrobromide. -2, 3, 8, 8a-tetrahydroindeno [1,2-d] thiazole-3a-ol 426 mg of 2-bromo-4- (4-trifluoromethylphenyl) indan-1-one and 131 mg of N, N'- dimethylthiourea are mixed in 10 ml of acetone at room temperature and the mixture is stirred for 4 hours. The deposited precipitate is removed by filtration with suction, washed with acetone and dried in vacuum. 3-Methyl-2-methylimino-7- (4-trifluoromethyl-phenyl) -2, 3, 8, 8a-tetrahydroindeno [1, 2-d] thiazol-3a-ol hydrobromide is obtained with a p >; melting point of 202-204 ° C. starting at p > After 4-bromoindan-1-one, compound A40 was obtained analogously. Example 5 (compound A42) 3-Methyl-2-methylimino-6-pyridin-3-yl-2, 3, 8, 8a-tetrahydroindeno [1, 2-d] -thiazole-3a-ol a) 5- Hydrochloride pyridin-3-yl-indan-l-one: 13.26 g of 3-bromopyridine are dissolved in 160 ml of diethyl ether and cooled to -60 ° C. 52 ml of a 1.6 molar solution is added dropwise to this solution of n-butyllithium in n-hexane. The solution is allowed to warm to -30 ° C and 9.5 ml of trimethyl borate is added, drop by drop, with stirring at this temperature. The reaction mixture is subsequently heated under reflux for 3 hours, then cooled to 0 ° C and treated dropwise with 6.1 ml of 1,3-propanediol. This mixture is stirred at a temperature of 0 ° C for 30 minutes before the dropwise addition of 5.46 ml of methanesulfonic acid, and stirred for an additional 30 minutes. 20 g of Celite are then added, the mixture is warmed to room temperature and filtered, the filtrate is concentrated, the residue is stirred in 700 ml of toluene and filtered again, and the solvent is removed by vacuum distillation. Dissolve 4.1 g of the residue (3- [1, 3, 2] dioxaborinan-2-yl-pyridine) in a mixture of 100 ml of toluene with 20 ml of ethanol and 20 ml of water without further purification together with 4.22 g of 5-bromoindan-l-one and 4.24 g of sodium carbonate. The solution is rinsed with argon, and then 112 mg of palladium (II) acetate and 262 mg of triphenylphosphine are added. The reaction mixture is refluxed for 4 hours, cooled to room temperature and the ethanol part of the mixture is removed by vacuum distillation. 50 ml of a 0.5 N sodium hydroxide solution is then added with stirring, the organic phase is separated and the aqueous phase is extracted by stirring with toluene. The combined organic phases are extracted by successively stirring with water and a saturated solution of sodium chloride, dried over magnesium sulfate, concentrated in vacuo and purified by chromatography on silica gel using ethyl acetate / n-heptane 1/1. There is obtained 5-pyridin-3-ylindan-1-one of melting point 103-106 ° C. b) 2-Chloro-5-pyridin-3-ylindan-1-one: 3.22 g of 5-pyridine are dissolved. 3-ilindan-1-one in 160 ml of dichloromethane and treated dropwise with a 1.34 ml solution of chlorure? of sulfuryl in 40 ml of dichloromethane at a temperature of 0 ° C within 15 minutes. The mixture is stirred at 0 ° C for 30 minutes and then at room temperature for 60 minutes before slowly adding 50 ml of a saturated solution of sodium hydrogencarbonate. The organic phase is separated, washed with water, dried over magnesium sulfate, concentrated in vacuo and purified by chromatography on silica gel using dichloromethane / methanol 50/1. Obtained 2-chloro-5-pyridin-3-ylindan-1-one with melting point 103-105 ° C (in addition to 2,2-dichloro-5-pyridin-3-ylindan-1-one) fusion temperature 109 ° C). c) 3-Methyl-2-methylimino-6-pyridin-3-yl-2, 3, 8, 8a-tetrahydroindeno- [1, 2-d] thiazol-3a-ol hydrochloride 366 mg of 2-chloro are dissolved -5-pyridin-3-ylindan-1-one and 235 mg of N, N "-dimethylthiourea in 5 ml of methanol and reflux for 7 hours.The reaction mixture is cooled and concentrated in vacuo. It is treated with 5 ml of acetone, stirred in an ultrasonic bath for 30 minutes and then removed by filtration with suction.The residue is reacted with acetone and dried in vacuo.The 3-methyl-2-methylimino-6- hydrochloride is obtained. pyridin-3-yl-2, 3, 8, 8a-tetrahydroindeno- [1,2-d] thiazole-3a-ol having a melting point of 253-255 ° C. Example 6 (compound A41): Hydrobromide 3-Methyl-2-methylimino-6-trifluoromethoxy-2,3,8,8-tetrahydroindeno- [1,2-d] thiazol-3a-ol: a) methyl 3-trifluoromethoxycinnamate 9.15 g of 3-aq. trifluoromethoxycinnamic acid in 90 ml of methanol 0.25 ml of concentrated sulfuric acid is added and the mixture s refluxed for 5 hours. The cooled solution is treated carefully with 0.9 g of sodium hydrogencarbonate, stirred for 5 minutes and then concentrated in vacuo. The residue is taken up in 250 ml of ethyl acetate, washed twice with 50 ml of water each time and dried in magnesium sulfate. The solution is concentrated in vacuo and the residual pale oil reacts further without further purification. b) Methyl 3- (3-trifluoromethoxy-phenyl) propionate 9.6 of methyl 3-trifluoromethoxycinnamate are dissolved in 200 ml of methanol. 750 mg of palladium on carbon (10%) is added and the mixture is hydrogenated at normal pressure. After a usual treatment, methyl 3- (3-trifluoromethoxy-phenyl) propionate is obtained in the form of a yellow oil. c) 5-trifluoromethoxyindan-1-one: 9.37 g of methyl 3- (3-trifluoromethoxy-phenyl) propionate are dissolved in 50 ml of ethanol with 25 ml of water. 3.74 g of potassium hydroxide is added and the mixture is refluxed for 45 minutes. The cooled solution is concentrated, the residue is treated with 25 ml of water, and concentrated hydrochloric acid is added with stirring to a pH of 1. The aqueous reaction mixture is extracted twice by shaking with 75 ml of dichloromethane in each case. case. The organic phase is washed with water, dried over magnesium sulfate, concentrated and dried in a vacuum. 3- (3-Trifluoromethoxy) propionic acid is obtained in the form of a colorless oil. 6.24 of the acid is dissolved in 40 ml of toluene, and the solution is treated with 2.1 ml of thionyl chloride and refluxed for 1 hour. The cooled reaction mixture is concentrated, and the residue is taken up in 5 ml of toluo and concentrated again. 3- (3-Trifluoromethoxy-phenyl) -propionyl chloride, dissolved in 30 ml of dichloromethane is obtained with further purification and added dropwise at a temperature of 0-5 ° C with stirring in the course of 5 minutes to a suspension of 5.49. g of anhydrous aluminum trichloride in 40 ml of dichloromethane. The reaction mixture is stirred at 0 ° C for 1 hour and then added to 40 ml of ice water. The organic phase is separated and the aqueous phase is extracted again by stirring with 40 ml of dichloromethane. The combined organic phases are washed with 40 ml of a saturated solution of sodium hydrogencarbonate and water, dried over magnesium sulfate, concentrated in vacuo and, for purification, purified by chromatography on silica gel using toluene / ethyl acetate 20/1 . 5-trifluoromethoxyindan-1-one is obtained in the form of a pale yellow oil. d) 2-bromo-5-trifluoromethoxyindan-1-one: 5.3 of 5-trifluoromethoxyindan-1-one is dissolved in 50 ml of glacial acetic acid, treated with HOμ hydrobromic acid (48% in glacial acetic acid) and treated drop by drop at room temperature with a solution of 1,305 ml of bromine in 12 ml of acetic acid. The reaction mixture is stirred at room temperature for 90 minutes, then treated with 70 ml of water and extracted several times with stirring with 100 ml of dichloromethane each time. The organic phases are washed with 50 ml of water, dried over magnesium sulfate, concentrated in vacuo and the residue is chromatographed on silica gel using toluene / ethyl acetate 50/1. 2-Bromo-5-tri luoromethoxyindan-1-one is obtained in the form of a wax. e) 3-Methyl-2-methylimino-6-trifluoromethoxy-2,3,8,8a-tetrahydroindeno [1,2-d] thiazole-3a-ol hydrobromide 0.197 g of 2-bromo-5-trifluoromethoxyindan- 1-one at room temperature for 5 hours with 0.104 g of N, N'-dimethylthiourea in 5 ml of acetone. The suspension obtained is further stirred at 0 ° C for 1 hour and then removed by suction filtration; The residue is washed with acetone and dried in vacuum. The hydrobromide of 3-methyl-2-methylimino-6-trifluoromethoxy-2,3,8,8a-tetrahydroindeno [1,2-d] -thiazole-3a-ol is melted at a temperature of 162 ° C with decomposition.

Example 7 (compound A35): 5-tert-Butyl-3-methyl-2-methylimino-2,3,8,8-tetrahydroindeno [1,2-d] -thiazole-3a-ol hydrobromide: a) 3- (Methyl 4-tert-butylphenyl) acrylate: 3-4-tert-butylphenyl acrylic acid) reacts with sulfuric acid in methanol to provide methyl 3- (4-tert-butylphenyl) acrylate analogously to example 6a). the ester has a waxy consistency with a melting point of about 35 ° C. b) methyl 3- (4-tert-butylphenyl) propionate 10.0 g of methyl 3- (4-tert-butylphenyl) acrylate is dissolved in 75 ml of absolute ethanol. 2.45 g of magnesium burrs are introduced in portions over the course of one hour and the mixture is stirred at room temperature for three hours. 380 mg of magnesium burrs is then added and the mixture is stirred for an additional 1 hour. With cooling (ice bath), 90 ml of 2N hydrochloric acid is carefully added dropwise with stirring. The methanol is then removed in vacuo, the residue is extracted twice with 200 ml of dichloromethane in each case, and the dichloromethane phase is washed with water until reaching a neutral level (2 x 50 ml) dried in magnesium sulfate and concentrated Methyl 3- (4-tert-butylphenyl) propionate is obtained in the form of a waxy, colorless compound. c) 3- (4-tert-Butylphenyl) propionic acid: 9.90 g of methyl 3- (4-tert-butylphenyl) propionate are dissolved in a mixture of 30 ml of ethanol with 15 ml of water, and the solution is treated with 4.46 g of potassium hydroxide, heated under reflux for 45 minutes. , and then concentrated in vacuo, treated with 30 ml of water, and while cooling in an ice bath, it is adjusted to a pH of 1 using concentrated hydrochloric acid. The aqueous solution is extracted three times by shaking with 100 ml of dichloromethane in each case, washed with water until reaching a neutral level, dried in magnesium sulfate and concentrated in vacuo. The residue is stirred with 100 ml of 25% acetic acid, cooled to 10 ° C and removed by suction filtration and dried in vacuo- 3- (4-tert-butylphenyl) propionic acid is obtained which is used in the next step without additional purification. d) 3- (4-tert-Butylphenyl) propionyl chloride: The acid chloride is prepared according to that described in example 6c) and used in the next step without further purification. e) 6-tert-butyl Lindan-1-one: 6-tert-butylindan-1-one is prepared from 7d acid chloride according to that described in 6c). 6-tert-butylindan-1-one has a melting point of 94-96 ° C. F) 2-bromo-6-tert-butylindan-l-one: According to the process described in 6d), 6-tert-butilindan -l-one is converted to 2-bromo-6-tert-butylindan-1-one; has a melting point of 58-61 ° C. g) Hydrobromide of 5-tert-butyl-3-methyl-2-methylimino-2,3,8,8-tetrahydroindeno [1,2-d] -thiazole -3a-ol: The reaction of 267 mg of 2-bromo-6-tert-butylindan-1-one with 156 mg of N, N '-dimethylthiourea in 10 ml of acetone gives the hydrobromide of 5-tert-butyl-3 -methyl-2-methylimino-2,3,8,8-tetrahydroindeno [1,2-d] -thiazole-3a-ol mp 277-279 ° C. Example 8 (compound A23) 3a-hydroxy hydrobromide 3-methyl-2-methylimino-3, 3a, 8, 8a-tetrahydro-2H-indene [1, 2-d] 6-carbonitrile a) l-oxoindan-5-carbonitrile 9.5 g of 5-bromoindan- l-one and 4.93 g of CuCN in 10 ml of dimethylformamide and refluxed for 4 hours. A solution of 18 g of iron (III) chloride in 5 ml of concentrated hydrochloric acid is added, dropwise exhausts, with 30 ml of water with stirring to the viscous dark brown suspension, cooled, and then stirred to a temperature of 70 ° C for 30 minutes. The reaction mixture is extracted three times by shaking with 50 ml of toluene, and the combined organic phases are extracted by stirring with 50 ml of 2N hydrochloric acid and 50 ml of a 2N sodium hydroxide solution, and then washed with water until reaching a neutral level. The toluene extract is dried in magnesium sulfate and concentrated in vacuo, and the residue is recrystallized from n-heptane. L-Oxoindan-5-carbonitrile with a melting point of 123-125 ° C is obtained. B) 2-bromo-l-oxoindan-5-carbonitrile: The bromination of l-oxoindan-5-carbonitrile is carried out in accordance with as described in example 6d) and 2-bromo-l-oxoindan-5-carbonitrile with a melting point of 115-118 ° C is obtained. c) 3a-hydroxy-3-methyl-2-methylimino-3 hydrobromide. , 3a, 8, 8a-tetrahydro-2H-indene [1,2-d] 6-carbonitrile: 236 mg of 2-bromo-l-oxoindan-5-carbonitrile are dissolved in 10 ml of acetone and treated at a temperature from 0-5 ° C with 210 mg of N, N'-di ethylthiourea. The mixture is stirred at room temperature for 3 hours and at a temperature of 0 ° C for 1 hour. The product of the reaction is removed by filtration with suction, washing with acetone and drying in vacuum. A hydrobromide of 3a-hydroxy-3-methyl-2-methylimino-3, 3a, 8, 8a-tetrahydro-2H-indene [1,2-d] 6-carbonitrile with a melting point of 282-284 ° is obtained C (decomposition). Compound A12 was prepared analogously, starting from 6-bromoindan-1-one. Example 9 (compound Al8) 3-methyl-2-methylimino-5-methylsulfonyl-6-phenylthio-2,3,8- tetrahydroindeno [1,2-d] -thiazole-3a-ol a) 6-methylsulfoni1- 5-phenylthio-1-indanone: 2.55 ml of thiophenol is added dropwise under an argon atmosphere and with stirring to a suspension prepared from 4.9 g of 6-methylsulfonyl-5-phenylthio-1-indanone, 1.4 g of anhydrous ground potassium carbonate and 50 ml of DMF and the mixture is heated to a temperature of 80 ° C for about 10 hours while stirring is maintained. After the addition of 500 ml of water at room temperature, the crystals are removed by filtration and purified by dissolving in acetone, treatment with activated charcoal and subsequent precipitation with water. Obtained crystalline substances of pale yellow color with a melting point of 211-212 ° C. b) 2-bromo-6-methylsulfonyl-5-phenylthio-1-indanone It is obtained by the dropwise addition of a mixture of 0.39 ml of bromine in 10 ml of glacial acetic acid to a stirred solution of 2.4 g of 6-methylsulfonyl-5-phenylthio-1-indanone, 0.2 ml of concentrated aqueous hydrobromic acid and 30 ml of glacial acetic acid, followed by pouring the reaction mixture into a suspension of water and ice, and subsequent filtration of the crystalline product. A slightly yellow crystalline substance with a melting point of 158-160 ° C is obtained. C) 3-Methyl-2-methylimino-5-methylsulfonyl-6-phenylthio-2,3,8,8a-tetrahydroindene hydrobromide. [1, 2-d] -thiazole-3a-ol 0.72 g of N, N'-dimethylthiourea is added to a solution of 2.7 g of 2-bromo-6-methylsulfonyl-5-phenylthio-1-indanone in 30 ml of acetone, the mixture is stirred at room temperature for 1 hour, and the crystalline compound of melting point 268-270 ° C is filtered with decomposition. d) 3-methyl-2-methylimino-5-methylsulfonyl-6-phenylthio-2,3,8,8-tetrahydroindeno [1,2-d] -thiazole-3a-ol 3-methyl-2-hydrobromide is suspended methylimino-5-methylsulfonyl-6-phenylthio-2,3,8,8-tetrahydroindeno [1,2-d] -thiazole-3a-ol in methanol and treated with a triple molar excess of triethylamine. The resulting solution is filtered and crystallized by trituration with a glass rod. A colorless crystalline compound with a decomposition melting point of 142-143 ° C is obtained. Example 10 (compound A48): 8-Chloro-5a-hydroxy-3, -dihydro-7-methylsulfonyl-indan hydrobromide [2, 1-b] imidazo [1,2-d] thiazolidine a) 5-chloro-6-nitro-l-indanone: 86 g of 5-chloro-6-nitro-l-indanone are introduced with stirring and • external cooling in 540 ml of smoking nitric acid having a density of 1.52 g / ml such that the internal temperature is maintained between -15 and -10 ° C. The reaction mixture is poured into a stirred water / ice suspension and stirred. by filtration the yellow crystalline substance. It is purified by dissolution in a mixture of 2 parts acetone and 5 parts of ethanol, it is treated with activated charcoal and an extensive removal of the acetone content is effected by distillation under reduced pressure. Melting point 126-128 ° C. b) 6-amino-5-chloro-l-indanone: A solution of 77.5 g of sodium hydrogensulfite in 250 ml of water is added dropwise to a boiling suspension of 30 g of 5-chloro-6-nitro-l-indanone in 400 ml of water over the course of 1 hour while boiling is maintained and the mixture is refluxed for an additional 2 hours. Carefully adjust to pH 1-2 using concentrated hydrochloric acid and heat to boiling for an additional 1 hour. After cooling, the crystals are removed by filtration, washed with water and recrystallized from isopropanol. A crystalline substance is obtained which varies from colorless to brown, with a melting point of 210-212 ° C with decomposition, c) 5-chloro-6-chlorosulfonyl-1-indanone: A solution of 10.4 g of nitrite is added. Sodium in 30 ml of water dropwise to a suspension of 26.8 g of 6-amino-5-chloro-1-indanone in 200 ml of 20% hydrochloric acid with good agitation and cooling, the temperature is maintained between 0 and 5 C. In the course of this, the solution is obtained which, after further stirring at 0 ° C, is added in portions with stirring to a solution of 12.7 g of copper (II) chloride dihydrate, 50 ml of water and 400 ral of glacial acetic acid saturated with sulfur dioxide at a temperature of 0-5 ° C. The mixture is stirred for an additional 1 hour without external cooling, then 600 ml of water is added and the crystals are removed by filtration, washed with cold water several times in the filter and then dried in vacuum. A colorless crystalline substance is obtained; melting point 147-148 ° C. d) 5-chloro-l-indanone-6-sulfinic acid: 13.3 of 5-chloro-6-chlorosulfonyl-1-indanone is introduced in portions with stirring in a solution of 26 g of sodium hydrogensulfite and 3 g of NaOH in 75 ml of water, a 2N sodium hydroxide solution being added dropwise simultaneously from a dropping funnel in such a way that the pH is maintained between 7 and 7.5. The mixture is then stirred at a pH of 1-2 using concentrated hydrochloric acid, cooled to a temperature of 0 to -5 ° C, and the crystals are removed by filtration and washed with water. Melting point > 300 ° C with blackening from 170 ° C e) 5-chloro-6-methylsulfoni-1-indanone: First, 9.2 g of 5-chloro-l-indanone-6-sulfinic acid and then 15 g of iodide are added. of methyl to a solution of sodium methoxide which has been prepared from 150 ml of methanol and 1 g of sodium and the mixture is heated to boiling for 10 hours under the condenser of added efficiency. After removing the solvent by distillation, the residue is treated with 200 ml of water, the crystals are removed by filtration and the product is carefully washed with water. A colorless crystalline substance is obtained from methanol after treatment with activated carbon, melting point 197-198 ° C. f) 2-bromo-5-chloro-6-methylsulphyl-1-indanone: Obtained from 6.8 g of 5-chloro-6-methylsulfonyl-l-indanone and 1.45 g of bromine in glacial acetic acid. A colorless crystalline substance is obtained up to a light brown color with a melting point of 144 ° C. G) 8-Chloro-5a-hydroxy-3,4-dihydro-7-methylsulfonyl-indane hydrobromide [2, 1-b ] imidazo [1,2-d] thiazolidine A warm solution of 1.02 g of 2-imidazolidinthione in 7.5 ml of dimethylacetamide is added with stirring to a solution of 3.24 g of 2-bromo-5-chloro-6-methylsulfonyl-l- indanone in 50 ml of acetone and the mixture is stirred at room temperature for an additional 2 hours. The colorless crystalline compound is removed by filtration and washed several times with acetone. Decomposition point 135 ° C. h) 8-Chloro-5a-hydroxy-3,4-dihydro-7-methylsulfonylindane [2, 1-b] imidazo [1,2-d] thiazolidine Obtained analogously to the procedure indicated in Example 9 from 8-chloro-5a-hydroxy-3,4-dihydro-7-methylsulfonyl-indane [2, 1-b] imidazo [1,2-d] thiazolidine hydrobromide and triethylamine in methanol. A colorless crystalline substance with a decomposition point of 192 ° C is obtained. Example 11 (compound A27) 6- (4-chlorophenoxy) -3-methyl-2-methylimino-2,3,8, 8a-tetrahydroindenohydrochloride [ 1,2-d] -thiazole-3a-ol a) 5- (4-chlorophenoxy) -1-indanone: After dissolution in 60 ml of anhydrous dimethylacetamide, 2.82 g of 4-chlorophenol are stirred at room temperature for half an hour with 8.2 g of ground and anhydrous potassium carbonate. After the addition of 1.5 g of 5-fluoroindanone, the mixture is stirred at a temperature of 120-130 ° C for 10 hours and the solvent is removed by distillation under reduced pressure after cooling. The residue is treated with water and extracted several times with ethyl acetate. The organic phase is washed with 2N NaOH and subsequently with water, and then stirred for 15 minutes after the addition of activated carbon and the solvent is removed by distillation under reduced pressure after drying in anhydrous magnesium sulfate. The partially crystalline dark residue is purified by column chromatography on silica gel using an eluent consisting of equal parts of ethyl acetate and toluene. Brown crystals are obtained, melting point 75-80 ° C. b) 2-bromo-5- (4-chlorophenoxy) -1-indanone: Approximately 1/2 ml of a solution of 0.25 ml of bromine in 5 ml of ethyl acetate is added dropwise to a solution of 1.3 g of 5- (4-Chlorophenoxy) -1-indanone in 30 ml of ethyl acetate and the mixture is slowly heated until bromine decolorizes or until the start of HBr emission. It is then cooled and the remaining amount of bromine is added dropwise at room temperature, the mixture is stirred for an additional 2 hours and the solvent is removed by distillation under reduced pressure. The residual dark oil is used without further purification. c) 6- (4-chlorophenoxy) -3-methyl-2-methylimino-2,3,8, 8a-tetrahydroindeno [1,2-d] -thiazole-3a-ol hydrobromide Obtained by the reaction of 1.69 g of 2-bromo-5- (4-chlorophenoxy) -1-indanone and 0.52 g of N, N'-dimethylthiourea in 25 ml of ethyl acetate in the form of a pale yellow to colorless crystalline precipitate. Melting point 252-255 ° C. d) 6- (4-chlorophenoxy) -3-methyl-2-methylimino-2,3,8-8-tetrahydroindeno [1,2-d] -thiazole-3a-ol It is formed by treating a solution of 1.5 g of 6- (4-chlorophenoxy) -3-methyl-2-methylimino-2,3,8a-tetrahydroindeno [1,2-d] -thiazole-3a-ol hydrobromide in 40 ml of methanol with 2.3 ml of triethylamine. The solvent is removed by distillation and the residue is solidified in water. An amorphous solid with a melting point of 85-90 ° C is obtained. E) 6- (4-Chlorophenoxy) -3-methyl-2-methylimino-2,3,8,8a-tetrahydroindene hydrochloride [1, 2 d] -thiazole-3a-ol Obtained in the form of a colorless crystalline precipitate by adding a solution of HCl gas in diethylether to a solution of 1.2 g of 6- (4-chlorophenoxy) -3-methyl-2-methylimino- 2, 3, 8, 8a-tetrahydroindeno [1,2-d] -thiazole-3a-ol in 30 ml of ethyl acetate to obtain a strongly acidic reaction. Melting point 247-250 ° C. Example 12 (compound A28): 6- (2, 2, 2-trifluoroethoxy) -3-methyl-2-methylimino hydrobromide -2,3,8, 8a-tetrahydroindeno [1,2-d] -thiazol-3a-ol a) 5- (2,2,2-trifluoroethoxy) -1-indanone: 2.2 ml of 2, 2 are added, 2-trifluoroethanol to a mixture of 3.5 g of 5-fluoroindanone, 20 ml of anhydrous dimethylformamide and 4.1 g of anhydrous and milled potassium carbonate and the mixture is stirred at a temperature of 80 ° C for 10 hours. The solvent is removed by distillation under reduced pressure, the residue is dissolved in ethyl acetate and the organic phase is washed several times with water. The indanone derivative is obtained in the form of a brown crystalline solid after chromatography on silica gel by mixing a mixture of equal parts of ethyl acetate and toluene as eluent. Melting point 93-97 ° C. B) 2-bromo-5- (2,2,2-trifluoroethoxy) -1-indanone: It is obtained by reaction of 0.9 g of 5- (2,2,2-trifluoroethoxy) -1-indanone with 0.2 ml of bromine in 25 ml of ethyl acetate. The compound is further employed without further purification. c) 6- (2, 2, 2-trifluoroethoxy) -3-methyl-2-methylimino-2,3,8a-tetrahydroindeno [1,2-d] -thiazole-3a-ol hydrobromide Obtained by reaction 1.2 g of 2-bromo-5- (2,2,2-trifluoroethoxy) -1-indanone and 0.4 g of N, N'-dimethylthiourea in 25 ml of ethyl acetate in the form of a pale yellow crystalline precipitate until colorless. Melting point 278-280 ° C. D) 6- (2,2,2-trifluoroethoxy) -3-methyl-2-methylimino-2,3,8,8-tetrahydroindeno [1,2-d] -thiazole- 3a-ol Obtained from 6- (2,2,2-trifluoroethoxy) -3-methyl-2-methylimino-2,3,8,8-tetrahydro-indene [1,2-d] -thiazole hydrobromide -3a-ol and triethylamine. A colorless crystalline solid with a melting point of 138-140 ° C is obtained. E) Hydrochloride of 6- (2,2,2-trifluoroethoxy) -3-methyl-2-methylimino-2, 3, 8, 8a- tetrahydroindeno [1,2-d] -thiazole-3a-ol It is obtained from 6- (2,2,2-trifluoroethoxy) -3-methyl-2-methylimino-2,3,8-8-tetrahydroindeno [1,2-d] -thiazole-3a-ol and a solution of HCl gas in ether. Obtain colorless crystals, melting point 274-276 ° C. Example 13 (compound A45): Hydrochloride of 5- (2, 2, 3, 3,4,4,4-heptafluorobutoxy) -3-methyl-2-methylimino-2, 3,8,8a-tetrahydroindeno [1,2-d] -thiazole-3a -ol a) 5- (2, 2, 3, 3, 4, 4, 4-heptafluorobutoxy) -1-indanone: It is obtained starting from 5.6 g of 5-fluoroindanone and 35.6 g of anhydrous potassium carbonate and ground in 50 g. ml of anhydrous dimethylacetamide in the form of a honey-colored oil. b) 2-bromo-5- (2,2,3,3,4,4, 4-heptafluorobutoxy) -1-indanone: It is obtained by the reaction of 4.16 g of 5- (2, 2, 3, 3, 4, 4, 4-heptafluorobutoxy) -1-indanone with 0.69 ml of bromine in 110 ml of ethyl acetate. The compound is isolated in the form of a brown oil and used without further purification. c) Hydrobromide of 6- (2, 2, 3, 3, 4, 4, 4-heptafluorobutoxy) -3-methyl-2-methylimino-2,3,8,8-tetrahydroindeno [1,2-d] -thiazole -3a-ol Obtained by the reaction of 1.4 g of 2-bromo-5- (2, 2, 3, 3, 4, 4-heptafluorobutoxy) -1-indanone and 0.36 g of N, N'-dimethylthiourea in 40 ml of ethyl acetate in the form of a pale yellow to colorless crystalline precipitate. Decomposition point 253 ° C. d) 6- (2, 2, 3, 3,4,4, 4-heptafluorobutoxy) -3-methyl-2-methylimino-2,3,8, 8a-tetrahydroindeno [1, 2 -d] -thiazole-3a-ol It is obtained from hydrobromide of 6- (2, 2, 3, 3,, 4, 4-heptafluorobutoxy) -3-methyl-2-methylimino-2, 3, 8, 8a -tetrahydro-indene [1,2-d] -thiazole-3a-ol and triethylamine. A colorless crystalline solid with a melting point of 138-140 ° C is obtained. E) Hydrochloride of 6- (2, 2, 3, 4, 4, 4-heptafluorobutoxy) -3-methyl-2-methylimino- 2, 3, 8, 8a-tetrahydroindeno [1,2-d] -thiazole-3a-ol Obtained from 6- (2, 2, 3, 3, 4, 4, 4-heptafluorobutoxy) -3-methyl -2-methylimino-2, 3, 8, 8a-tetrahydroindeno [1,2-d] -thiazole-3a-ol and ethereal hydrochloric acid. Colorless crystals with a melting point of 248-250 ° C are obtained. Example 14 (compound Bl): 6-chloro-8a-fluoro-3-methyl-2-methylimino-2,3,8-tetrahydro-indene [1, 2-d] -thiazole-3a-ol: a) 5-chloro-2-fluoroindan-1-one 25 ml of a 1.6 molar solution of n-butyllithium in n-hexane are slowly added dropwise to a temperature < -50 ° C to a solution of 5.24 ml of diisopropylamine in 60 ml of dry tetrahydrofuran; The mixture is then stirred at a temperature of -50 ° C for an additional 10 minutes. A solution of 6.33 g of 5-chloroindan-1-one in 60 ml of dry tetrahydrofuran is then added slowly and the mixture is stirred at a temperature of -50 ° C for an additional 20 minutes. Finally, 11.4 g of N-fluorodibencenesulfimide, dissolved in 60 ml of dry tetrahydrofuran, are added dropwise. The mixture is allowed to warm to 0 ° C over the course of 2 hours with stirring, 120 ml of a saturated solution of sodium hydrogen carbonate is added dropwise, the tetrahydrofuran is removed by vacuum distillation and the residue is extracted twice. times by stirring with 150 ml of ethyl acetate. The organic phase is washed with water and a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated, and the residue is purified by chromatography on silica gel using diisopropyl ether / n-heptane 1/1. In addition to 5-chloro-2, 2-fluoroindan-1-one, 5-chloro-2-fluoroindan-1-one with a melting point of 102-104 ° C is obtained. B) 5-chloro-2-bromo -2-fluoroindan-1-one: The bromination 5-chloro-2-fluoroindan-1-one is carried out analogously to that described in 6d) and provides 5-chloro-2-bromo-2-fluoroindan-1 ona with a melting point of 104-105 ° C. c) 6-chloro-8a-fluoro-3-methyl-2-methylimino-2,3,8-tetrahydroindeno [1,2-d] - thiazol-3a-ol 263 mg of 5-chloro-2-bromo-2-fluoroindan-1-one and 156 mg of N, N'-dimethylthiourea is dissolved in 5 ml of acetone and the solution is stirred, first at room temperature during 90 minutes and then at a temperature of 50 ° C for 2 hours. The reaction mixture is cooled and concentrated in vacuo. 5 ml of toluene is added to the residue and the mixture is heated under reflux for 2 hours, cooled, treated with 152 mg of triethylamine and stirred at room temperature for 2 hours. The residue is removed by filtration, washed with a little water and dried in vacuum. 6-Chloro-8a-fluoro-3-methyl-2-methylimino-2,3,8,8-tetrahydro-indene [1,2-d] -thiazole-3a-ol having a melting point of 189- 190 ° C. Example 15 (compound B2): 6-Chloro-8a-fluoro-3-methyl-2-methylimino-2,3,8,8-tetrahydroindeno [1,2-d] -thiazole-3a-hydrochloride ol: Dissolve 1 g (4.47 mmol) of 6-chloro-8a-fluoro-3-methyl-2-methylimino-2,3,8-8-tetrahydroindeno [1,2-d] -thiazole-3a- in 120 ml of hot isopropanol and treated with 1.2 g of an ethereal HCl solution at approximately 20%. After 1 hour at room temperature, the reaction mixture is concentrated, and the residue is stirred with acetone, removed by filtration with suction and dried in vacuum. The hydrochloride of 6-chloro-8a-fluoro-3-methyl-2-methylimino-2,3,8,8-tetrahydroindeno [1,2-d] -thiazole-3a-ol with a melting point of 205 is obtained ° C (decomposition). Example 16 (compounds Bl (-) and Bl (+)): 100 mg of the racemate of compound Bl are resolved into the enantiomers through a HPLC column (CSP Chiralpak AD 250 x 4.6) using n-hexane / ethanol 10 + 1 . The rotary enantiomer (-) Bl (-) which has a retention time of 7.9 minutes of melting point 175-179 ° C (decomposition) and the rotary enantiomer (+) Bl (+) which has a retention time of ? .8 minutes of melting point 172-177 ° C (decomposition) are obtained. Example 17 (compounds Cl and C6) (6-chloro-3a-methoxy-3-methyl-3a, 3a, 8, 8a-tetrahydroindeno [1,2-d] -thiazol-2-ylidene) methylamine (hydrochloride): g of 6-chloro-3-methyl-2-methylimino-2,3,8a-tetrahydroindeno [1, 2-d] -thiazole-3a-ol hydrochloride are dissolved in 200 ml of methanol and the solution is heated under reflux for 3 days. The cooled reaction mixture is concentrated in vacuo and the residue is stirred with 50 ml of acetone and filtered. The filtrate is concentrated, the residue is suspended in 100 ml of ethyl acetate and the suspension is treated with 100 ml of a saturated solution of sodium hydrogencarbonate. The organic phase is separated, washed with water, dried over concentrated magnesium sulfate and chromatographed on silica gel using ethyl acetate / methanol 9/1. 6-Chloro-3-methyl-2-methylimino-2,3,8-8-tetrahydroindeno [1,2-d] -thiazole-3a-ol is obtained with a melting point of 94-96 ° C. The hydrochloride of this compound (compound C69 is obtained by the solution of the free base in methyltertbutyl ether and by the addition of ethereal hydrochloric acid with stirring and cooling with an ice bath to obtain a pH of about 1. The reaction mixture is then stirred at room temperature for an additional 3 hours, the solvent is removed by distillation and the residue is treated with acetone and filtrate.The filtrate is concentrated in vacuo and the residue is dried in vacuo, a 6-chloro-3-methyl hydrochloride is obtained. -2-methylimino-2, 3, 8, 8a-tetrahydroindeno [1, 2-d] -thiazol-3a-ol with a melting point of 65-70 ° C. Compounds C2-C5 were prepared analogously Examples 18 and b (compounds Cl (+) and Cl (-)): 100 mg of the racemate of compound Cl (free base) are resolved in the enantiomers to tr through a HPLC column (CSP Chiralpa.k AD 250 x 4.6) using n-hexane / 2-propanol /1 with 0.1% diethylamine. The rotary enantiomer (+) Cl (+) which has a retention time of 7.38 minutes and a specific rotation of 237.5 ° (c = 103 mg / 2 ml in trichloromethane) of melting point 70-71 ° C and the rotary enantiomer (-) Cl (-) which has a retention time of 8.06 minutes and a specific rotation of -229.1 ° (c = 9.9 mg / 2 ml in trichloromethane) of melting point of 71-72 ° C are obtained. Example 19 (compound D2) Hydrobromide of 8- (2-chlorophenyl) -3-methyl-2-methylimino-2,3,8,8a-tetrahydro-indene [1,2-d] -thiazole-3a-ol a) 2, 3-dibromo-3- (2-chlorophenyl) propionic acid It is obtained by dropwise addition of a solution of 7.8 g of bromine to a suspension of 9 g of 2-chlorocinnamic acid in 250 ml of chloroform with irradiation with a daylight lamp of 500 W and by subsequent evaporation of the solvent. Melting point 183-185 ° C. b) 2,3-dibromo-3- (2-chlorophenyl) propionyl chloride Obtained in the form of an oily, amorphous residue by boiling 10 g of 2,3-dibromo- 3- (2-chlorophenyl) propionic in 70 ml of thionyl chloride under reflux conditions and by liquid removal by distillation. c) 2-bromo-3- (2-chlorophenyl) -1-indanone 6.6 g of anhydrous active aluminum chloride are introduced into a mixture of 4.1 g of anhydrous benzene and 30 ml of carbon disulfide in an atmosphere of argon and the The mixture is then cooled to -20 ° C. While cooling is maintained, a solution of 15 g of 2,3-dibromo-3- (2-chlorophenyl) propionyl chloride in 50 ml of carbon disulfide is added dropwise. dropwise to that suspension, and the mixture is then kept at a temperature of 0 ° C for 5 hours and allowed to stand at a temperature of 4-8 ° C in a refrigerator for an additional 16 hours. The reaction mixture is drained with stirring in a strongly acidic ice-water mixture by the addition of concentrated HCl and extracted with chloroform, and the organic phase is washed with water and then dried over magnesium sulfate. After removal of the solvent by distillation, the viscous amorphous residue is taken up in diethyl ether, the mixture is stirred with an alkaline aqueous solution of sodium bicarbonate for several hours and the organic solvent is removed by distillation after drying in magnesium sulfate. A viscous amorphous substance is obtained. d) Hydrobromide of 8- (2-chlorophenyl) -3-methyl-2-methylimino-2, 3, 8, da-tetrihydroindeno [1,2-d] -thiazole-3a-ol It is treated 4 g of 2-bromine -3- (2-chlorophenyl) -1-indanone with 1.2 g of N, N '-dimethylthiourea in ethyl acetate and the mixture is stirred at room temperature for 2 days. A pale yellow crystalline substance with a melting point of 163 ° C is obtained. Example 20 (compound DI4): 3a-Hydroxy-3-methyl-2-methylimino-8-phenyl-3a hydrobromide, 8, 9, 9a-tetrahydronaphtho- [2, 1-b] thiazolidine a) 2-bromo-4-enyl-1-tetralone Obtained by the reaction of 4.43 g of 4-phenyl-1-tetralone in 3.2 g of bromine in ethyl acetate containing HBr in the form of a viscous amorphous product. b) Hydrobromide of 3a-hydroxy-3-methyl-2-methylimino-8-phenyl-3a, 8, 9, 9a-tetrahydronaphtho [2, 1-b] thiazolidine It is obtained by the reaction of 26 g of 2-bromo- 4-phenyl-1-tetralone and 5 g of N, N'-dimethylthiourea in 60 ml of ethyl acetate in the form of a pale yellow to colorless crystalline precipitate. Melting point 229-231 ° C (with decomposition). The DI compound was prepared analogously. Example 21 (compound DI6): l-ethyl-2-ethylimino-9-nitro-l, 2,4,5-tetrahydro-3aH-6-oxa-3-thia-1-azabenzo [e] azulen-lOb-ol a) 4-phenoxybutyryl chloride: 504.6 g of 4-phenoxybutyric acid are refluxed for 3 hours with 308 ml of thienyl chloride and 1.8 ml of dimethylformamide. The mixture is then distilled in vacuo and 4-phenoxybutyryl chloride is obtained with a boiling point of 145-147 ° C at a pressure of 10-12 mm Hg. b) 6, 7, 8, 9-tetrahydrobenzocyclohepten-5-one: 192 g of aluminum chloride (III) are suspended in 1.6 1 of 1,2-dichloroethane dry and a solution of 238 of 4-phenoxybutyryl chloride in 300 ml of 1 , 2-dichloroethane is slowly added dropwise with stirring at a temperature of -5 ° C under an atmosphere of argon protective gas in the course of 5.5 hours. The product of the reaction is subjected to hydrolysis by draining it in a mixture of 2 1 of water with 2 1 of concentrated hydrochloric acid. The mixture is stirred for 30 minutes, and the precipitate is allowed to settle and is removed by suction filtration. The organic phase is separated and the aqueous phase is extracted three times by stirring with 1,2-dichloroethane. The organic extracts are washed with water, with a diluted solution of hydrogencarbonate and finally with a saturated solution of sodium chloride, dried in sodium sulfate and concentrated in vacuo. The residue is distilled in vacuo. 6, 7, 8, 9-tetrahydrobenzocyclohepten-5-one is obtained having a melting point of 79-84 ° C at a pressure of 0.001 mm Hg in the form of a clear liquid. c) 7-Nitro-3, 4-dihydro-2H-benzo [b] oxepin-5-one: 25 g of 6, 7, 8, 9-tetrahydrobenzocyclohepten-5-one are dissolved in 280 ml of concentrated sulfuric acid at a temperature of -10 ° C. With vigorous stirring, a total of 16.75 g of sodium nitrate is introduced little by little at a temperature of -10 ° C. The dark reaction mixture is stirred at 0 ° C for 45 minutes; in the course of this, the residual sodium nitrate passes slowly into the solution. The reaction mixture is then added to ice water with stirring and stirred for 30 minutes. The precipitate is removed by filtration with suction and washed with water until neutral. The dried residue in air is recrystallized from isopropanol for purification. 7-Nitro-3,4-dihydro-2H-benzo [b] oxepin-5-one is obtained, which is further processed immediately. d) 4-bromo-7-nitro-3, 4-dihydro-2H-benzo [b] oxepin-5-one: 2.07 g of 7-nitro-3, -dihydro-2H-benzo [b] oxepin-5- ona are dissolved in 10 ml of dichloromethane and, while cooling with an ice bath, treated with stirring with 1.7 g of bromine, dissolved in 10 ml of dichloromethane (addition for 3 hours). The reaction mixture is introduced into 30 ml of a saturated sodium hydrogencarbonate solution, the organic phase is separated and the aqueous phase is extracted several times with dichloromethane. The combined organic extracts are washed with a saturated solution of sodium chloride, dried in sodium sulfate and concentrated, and the residue is recrystallized from butyl acetate and provides 4-bromo-7-nitro-3,4-dihydro- 2H-benzo [b] oxepin-5-one with a boiling point of 115-118 ° C. E) l-ethyl-2-ethylimino-9-nitro-l, 2,4,5-tetrahydro-3aH-6 -oxa-3-thia-1-azabenzc [e] azulen-10b-ol: 5 g of 4-bromo-7-nitro-3,4-dihydro-2H-benzo [b] oxepyr-5-one is heated to reflux for 30 minutes with 2.4 g of N, N'-diethylthiourea in 30 ml of butan-2-one. The precipitate is removed by suction filtration, stirred with a saturated solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic phase is washed with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated, and the residue is recrystallized from methanol / water. There is obtained l-ethyl-2-ethylimino-9-nitro-1,2,4,5-tetrahydro-3aH-6-oxa-3-thia-l-azabenzo [e] azulen-lOb-ol with a melting point 125-127 ° C. Compounds D12, D15, D17-D20, D22-D23, D26-D31 were prepared analogously starting from the corresponding derivatives of benzocyclohexanone or benzocycloheptanone. Example 22 (compound D21): l-methyl-2-methylimino-6,6-dioxo-l, 2, 3a-4, 5, 6-hexahydroditia-l-aza-benzo [e] azulen-10b-ol: a 4-phenylsulfanylbutyryl chloride: 54.9 g of 4-phenylsulfanylbutyric acid are dissolved in 280 ml of toluene using 0.5 ml of dimethylformamide. 36.5 ml of oxalyl chloride is added dropwise and the reaction mixture is added at room temperature for 2 hours and at a temperature of 6- 5-70 ° C for an additional hour. Toluene and excess oxalyl chloride are removed by vacuum distillation. The brown, oily residue is distilled in a high vacuum and provides 4-phenylsulfanylbutyryl chloride having a boiling point of 116-119 ° C at a pressure of 0.008 mm Hg. b) 3, 4-dihydro-2H-benzo [b] thiepin-5-one: 38.2 g of anhydrous aluminum (III) chloride are suspended in 260 ml of dichloromethane. A solution of 51.1 g of 4-phenylsulfanylbutyryl chloride in 70 ml of dichloromethane is slowly added, with stirring, at a temperature of 0 ° C (2 hours). The reaction mixture is stirred overnight, and a brown-yellow solution is obtained. This solution is added with vigorous stirring to an ice temperature mixture of 1 1 of water with 1 1 of concentrated hydrochloric acid. After stirring for 30 minutes, the mixture is extracted three times with 200 ml of diethyl ether in each case. The combined organic phases are extracted by stirring with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The oil obtained is distilled and 3,4-dihydro-2H-benzo [b] tiepin-5-one is obtained with a boiling point of 93-94 ° C at a pressure of 0.002 mm Hg. c) 1,1-dioxo-1,2,3,4-tetrahydrobenzo [b] thiepin-5-one: 10 g of 3,4-dihydro-2H-benzo [b] thiepin-5-one are dissolved in 125 ml of glacial acetic acid. 11.2 ml of 35% hydrogen peroxide is slowly added dropwise at room temperature with stirring. After stirring at room temperature for 2 hours, 11 ml of 35% hydrogen peroxide is added dropwise. The reaction mixture is then stirred overnight. The solvent is carefully removed under vacuum and the residue is treated with ice and treated carefully with a 1 N potassium hydrogen carbonate solution with stirring. The aqueous suspension is saturated with sodium chloride, and the precipitate is removed by filtration with suction, washed with water and dried in vacuum. There is obtained 1,1-dioxo-1,2,3,4-tetrahydrobenzo [b] thiepin-5-one with a melting point of 142-146 ° C. d) 4-bromo-1,1-dioxo- 1, 2,3, -tetrahydrobenzo [b] t? Epin-5-one: 9.45 g of 1,1-dioxo-1,2,3,4-tetrahydrobenzo [b] thiepin-5-one are dissolved in 200 ml of glacial acetic acid with agitation. 8.9 g of N-bromosuccinimide is added and the mixture is heated to a temperature of 75-80 ° C for 8 hours. After finishing the reaction, the solvent is removed by evaporation in vacuo and the oily residue is treated with a sodium hydrogen carbonate solution at ice temperature with stirring. After stirring for 30 minutes, the residue is removed by suction filtration and washed with water. After drying in vacuo, 4-bromo-l, l-dioxo-1,2,3,4-tetrahydrobenzo [b] thiepin-5-one having a melting point of 132-136 ° C is obtained e) l-methyl-2-methylimino-6,6-dioxo-l, 2, 3a-4, 5, 6-hexahydro-dithia-1-azabe zo [e] azulen-10-b-ol: 4.34 g of 4- bromo-l, 1-dioxo-l, 2, 3, 4-tetrahydro-benzo [b] thiepin-5-one are suspended in 15 ml of butan-2-one. The mixture is heated to a temperature of 60-70 ° C and 1.8 g of N, N'-dimethylthiourea is added in portions. The solution is refluxed for 2 hours, then cooled and the precipitate is removed by filtration with suction and washing with butan-2-one. The residue is stirred with 100 ml of a saturated solution of sodium hydrogencarbonate and extracted with ethyl acetate. The combined organic phases are washed with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated in vacuo. The residue is taken up with a little ethyl acetate, removed by filtration with suction and dried in vacuum. There is obtained 1-methyl-2-methylimino-6,6-dioxo-l, 2, 3a, 4, 5, 6-hexahydroditia-l-azabenzo [e] azulen-lOb-ol with a melting point of 142-144 ° C (decomposition). Example 23 (compound D25): N- (10b-hydroxy-l-methyl-2-methylimino-1, 2, 3a, 4, 5, 10b-hexahydro-6-oxa-3-thia-l-azabenzohydrochloride [ e] azulen-9-yl) acetamide: a) N- (5-oxo-2,3,4,5-tetrahydrobenzo [b] oxepin-7-yl) -acetamide: 16 g of 7-nitro-3 are dissolved , 4-dihydro-2H-benzo [b] oxepin-5-one in 400 ml of methanol, treated with 270 g of palladium on activated carbon (10%) and hydrogenated under normal pressure. After filtration and removal of the solvent in vacuo, 7-amino-3,4-dihydro-2H-benzo [b] oxepin-5-one, sensitive to oxygen, is obtained in the form of a yellow oil. This oil is dissolved in 150 ml of dichloromethane; 8 g of triethylamine is added and then, while cooling with ice, 8.1 g of acetic anhydride is slowly added dropwise with vigorous stirring. The reaction mixture is stirred at room temperature for an additional 1 hour. The solution is concentrated in vacuo and the residue is taken up in ethyl acetate, washed with water and with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated again. After crystallization from butyl acetate, the N- (5-OXO-2,3,4,5-tetrahydrobenzo [b] oxepin-7-yl) -acetamide melts at 130-132 ° C. B) N - (4-bromo-5-oxo-2, 3,4, 5-tetrahydrobenzo [b] oxepin-7-yl) -acetamide: Dissolves 1 g of N- (5-oxo-2, 3, 4, 5 -tetrahydrobenzo [b] oxepin-7-yl) acetamide in 6 ml of dichloromethane. 0.8075 g of bromine, dissolved in 5 ml of dichloromethane is slowly added dropwise at a temperature of 0 ° C with stirring. The reaction mixture is stirred overnight at room temperature, then poured into a saturated solution of sodium hydrogencarbonate at ice temperature and extracted several times with dichloromethane. The organic phases are washed with water and with a saturated solution of sodium dichloride, dried over sodium sulfate and concentrated in vacuo. The residue is recrystallized from isopropanol and provides N- (4-bromo-5-oxo-2, 3,4, 5-tetrahydrobenzo [b] oxepin-7-yl) -acetamide with a melting point of 157-160. C. c) N- (10b-hydroxy-l-methyl-2-methylimino-1,2,3a, 4, 5, 10b-hexahydro-6-oxa-3-thia-l-aza-benzohydrochloride] e] azulen-9-yl) acetamide: 7 g of N- (4-bromo-5-oxo-2,3,4,5-tetrahydrobenzo [b] oxepin-7-yl) -acetamide and 2.5 g of N, N '-dimethylthiourea are refluxed for 4 hours in 60 ml of butan-2-one. The cooled suspension is filtered, and the residue is stirred with 200 ml of a saturated solution of potassium hydrogencarbonate. A little ethyl acetate is added, the residue is removed by filtration. with suction and washing with water, and N- (10b-hydroxy-l-methyl-2-methylimino-l, 2, 3a-4, 5, 10b-hexahydro-6-oxa-3-thia-l-azabenzo is obtained [e] azulen-9-yl) acetamide with a melting point of 186-188 ° C. The free base is dissolved in 30 ml of 2 N hydrochloric acid. After stirring for about 10 minutes, the N- hydrochloride ( 10b-hydroxy-1-methyl 1-2-methylimino-l, 2, 3a, 4, 5, 10b-hexahydro-6-oxa-3-thia-l-azabenzo [e] azulen-9-yl) acetamide is precipitated . It melts with decomposition at a temperature of 270 ° C. Example 24 (compound E2): 6-Chloro-3- (4-methoxyphenyl) -2- (4-methoxyphenylimino) -2, 3, 8, 8a-tetrahydroindenohydrobromide [1,2-d] thiazole-3a-ol: 1 g of 2-bromo-5-chloroindan-1-one and 1.17 g of 1,3-bis (4-methoxyphenyl) thiourea are suspended in 50 ml of dry dichloromethane and are stirred at room temperature for 4 hours and at ice bath temperature for 1 hour. The precipitate is removed by filtration with suction, washed with dichloromethane and dried in vacuo. The hydrobromide of 6-chloro-3- (4-methoxyphenyl) -2- (4-methoxyphenylimino) -2, 3, 8, 8a-tetrahydroindeno [1,2-d] thiazol-3a-ol is obtained which melts at a temperature of 230-235 ° C with decomposition. The compounds -El and E3-E5 were prepared analogously.

Claims

CLAIMS A polycyclic thiazolidin-2-ylidenamine of the formula I wherein A) Y is a direct bond, -CH2-, -CH2-CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 is CN, COOH, COO-alkyl (d-C6), CONH2, CONH-alkyl (Ci-Ce), CON [alkyl ((C? -C6)] 2, alkyl (C: -6), alkenyl (C2) -C6), alkynyl (C2-C6), 0-CH2-CF3, 0-CH-CF2-CF3, O-alkyl (C4-C6), where in the alkyl radicals one or more or all of the hydrogen atoms can be replaced by fluorine or a hydrogen can be replaced by OH, OC (0) CH3, 0-CH; -Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (C? -C6), S- (CH2 ) n-phenyl, SO-alkyl (C: -C6), SO- (CH2) n-phenyl, S02-alkyl (C? -C6), S02- (CH2) r, -phenyl, where n can be equal to 0-6 and the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, OCF3, O-alkyl (C? -C6), alkyl (C.-C6), NH2; NH2, NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, NH-acyl (C1-C7), phenyl, biphenyl, 0- (CH2) n-phenyl, where n can ser = 0 - 6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, biphenyl rings , naphthyl , pyridyl, furanyl or thienyl in each case can be substituted one to three times by F, Cl, Br, I, OH, CF3, N02, CN, 0CF3, O-alkyl (Ci-Ce), alkyl (d-C6) , NH2, NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, S02-CH3, COOH, COO-alkyl (d-C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R1 'is H, F, Cl, Br, I, CH3, CF3, O-C1-C3 alkyl, N02, S02-NH2, S02NH-alkyl (C? -C6), S02 N [C1-C6 alkyl] )] 2 or Rl; R2 is H, (C? -C6) alkyl, (C3-C6) cycloalkyl, (CH2) n-phenyl, (CH2) p-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, C (O ) - (CH2) n-phenyl, C (O) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl, C (O) - (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); C (0) -alkyl (Ci-Ce), C (O) -cycloalkyl (C3-C6); R3 is H, (C? -C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2-COO alkyl (d-C6), CH2-C00 cycloalkyl (C3-C8), CH2- C00H, CH2-CONH2, CH2-CONHCH3, CH2"C0N (CH3) 2, (CH2) n" phenyl, (CH2) n-thienyl, (CH2) r-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); alkynyl (C2-d), alkenyl (C2-Ce), C (0) OCH3, C (0) OCH2CH3, C (0) 0H, C (0) NH2, C (0) NHCH3, C (0) N ( CH2) 2, 0C (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) r-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); R5 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) r-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-, or -CH2-CH2-CH2-CH2-; or B) Y is a direct bond, -CH2- or -CH2-CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 'independently among them are H, F, Cl, Br, I, N02, CN, COOH, COO-alkyl (C? -C6), CONH2, CONH-alkyl (C? -C6), CON- [(C? -C6)] alkyl, (C? -C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl; alkyl (C? ~ C6), 0-CH2-CF3, 0-CH2-CF2-CF3, 0-aL (C4-d) alkyl, where in the alkyl radicals one or more or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen atom can be replaced by OH, 0C (0) CH3, 0-CH2-Ph, NH2 or N (C00CH2Ph) 2; S-alkyl (C? -C6), S- (CH2 ) n-phenyl, SO-alkyl (Ci-d), SO- (CH2) r-phenyl, S02-alkyl (C? -C6), S02- (CH2) n-phenyl, where n can be = 0-6 and the phenyl radical may be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, 0CF3, O-alkyl (C? -C6), alkyl (Ci-Ce), NH2; S02-NH :, S02NH alkyl (Ci-Ce), S02N [(C? -C6) alkyl] 2, NH2, NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, NH-acyl (Ci-d), phenyl, biphenyl, O- (CH2) n ~ phenyl, where n can be = 0-6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl , 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings in each case can be substituted up to 3 times by F, Cl, Br, I , OH, CF3, N02, CN, OCF3, O-alkyl (C? ~ C6), alkyl (Ci-Ce), NH2, NH-alkyl (C? -C6), N- (alkyl (C? -C6) ) 2, S02-CH3, COOH, COO-alkyl (C? -C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is H, alkyl (Ci-d), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH?) N-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, C (O ) - (CH2) n-phenyl, C (0) - (CH2) n-thienyl, C (0) - (CH2) r-pyridyl, C (O) - (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (dC3), OH, O-alkyl (C6C6); C (O) -alkyl (Ci-Ce), C (O) -cycloalkyl (C3-C6); R3 is (C4-C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2-COO alkyl (C? -C6), CH2-COO cycloalkyl (C3-C8), CH2-COOH, CH2-CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n ~ phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl , F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (Ci-Ce); alkynyl (C2-C6), alkenyl (C2-C6), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) NHCH3, C (0) N (CH3) 2, OC (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) r-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); R5 is alkyl (C6C6), cycloalkyl (dd), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0- 5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-, or -CH2-CH2-CH2-CH2-; or C) Y is a direct bond, -CH2- or -CH2-CH2-; X is CH2, CH (CH3), CH (CH5), CH (C3H7); R1 and R1 'independently among them are H, F, Cl, Br, I, N02, CN, COOH, COO-alkyl (d-C6), CONH2, CONH-alkyl (C? ~ C6), CON- [alkyl ( (C? -C6)] 2, (C? -C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, 0-alkyl (C, -C6), 0-CH2-CF3, 0-CH2 -CF2-CF3, O-alkyl (C4-d), where in the alkyl radicals one or more or all of the hydrogen atoms can be replaced by fluorine or a hydrogen can be replaced by OH, 0C (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; 'S-alkyl (C? -C6), S- (CH2) n-phenyl, SO-alkyl (C? -C6), SO- (CH2) r, -phenyl, S02-alkyl (C? ~ C6), S02- (CH2) n-phenyl, where n can be = 0-6 and the phenyl radical can be substituted up to two times by F, Cl, Br, OH , CF3, N02, CN, 0CF3, O-alkyl (C? -C6), alkyl (C? -C6), NH2; S02-NH2, S02NH alkyl (d-C6), S02N [alkyl (C? -6) ] 2, NH2, NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, NH-acyl (C1-C7), phenyl, biphenyl, O- (CH2) n-phenyl, where n can be = 0 - 6, 1-naphthyl or 2-naphthyl , 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, bifidoyl, naphthyl, pyridyl, furanyl or thienyl rings in each case they can be substituted one to three times by F, Cl, Br, I, OH, CF3, N02, CN, OCF3, O-alkyl (Ci-Ce), alkyl (Ci-Ce), NH2, NH-alkyl (d- C6), N- (alkyl (d-C6)) 2, S02-CH3, COOH, COO-alkyl (Ci-Ce), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is (C6C6) alkyl, (C3-d) cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) ) n-furyl, C (O) - (CH2) n-phenyl, C (O) - (CH2) n-thienyl, C (O) - (CH2) n-pyridyl, C (O) - (CH2) n -furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to times by Cl, F, CN, CF3, alkyl (d-C3), OH, O- alkyl (C? -C6); C (O) -alkyl (d-C6), C (O) -cycloalkyl (C3-C6); R3 is H, (C4-C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2-COO alkyl (Ci-Ce), CH2-COO cycloalkyl (C3-Ce), CH2-COOH , CH2-CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (d-C3), OH, O-alkyl (Ci-d); alkynyl (C2-d), alkenyl (-d), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) NHCH3, C (0) N (CH3 ) 2, OC (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (Ci-d), OH, O-alkyl (C6C6); R5 is alkyl (Ci-d), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0 - and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to several times by Cl, F, CN, CF3, alkyl (C? -C3), OH, O-alkyl (d-C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-, or -CH2-CH2-CH2-CH2-; or D) Y is a direct bond, -CH2- or -CH2-CH2-; X is CH (phenyl), wherein the phenyl radical can be substituted by F, Cl, Br or I, O, S, SO, S02 or N-R6; R1 and R1 'independently are H, F, Cl, Br, I, N0, CN, COOH, COO-alkyl (C? -C6), CONH2, CONH-alkyl (C? -C6), CON- [alkyl] ((d-C6)] 2, alkyl (Ci-Ce), alkenyl (C2-C6), alkynyl (C2-C6); 0-alkyl (C? -C6), 0-CH2-CF3, 0-CH2- CF2-CF3, O-alkyl (C4-Ce), wherein at the alkyl radicals one or more or all of the hydrogen atoms may be replaced by fluorine, or a hydrogen atom may be replaced by OH, 0C ( CH3, 0-CH2-Ph, NH2 or N (C00CH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, SO-alkyl (C? -C6), SO- ( CH2) n-phenyl, S02-alkyl (C? ~ C6), S02- (CH2) n-phenyl, where n can be = 0-6 and the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF, N02, CN, OCF3, O-alkyl (C? -C6), alkyl (Ci-Ce), NH2; SO2-NH2, S02NH-alkyl? (C? -C6), S02N- [alkyl (C ? -C6)] 2, NH2, NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, NH-acyl (C1-C7), phenyl, biphenyl, O- (CH2) n-phenyl, where n can be = 0-6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2- furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl rings, biphenyl ,. Naphthyl, pyridyl, furanyl or thienyl in each case may be substituted one to three times by F, Cl, Br, I, OH, CF3, N02, CN, OCF3, O-alkyl (C? -C6), alkyl (d-C6), NH2, NH-alkyl (d-C6), N- ((C? -C6) alkyl) 2, COOH, COO-alkyl (C? -C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is H, (C? -C6) alkyl, (C3-C6) cycloalkyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, C (0) ) - (CH2) n-phenyl, C (0) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl ,. C (O) - (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl ( C1-C3), OH, O-alkyl (C? -C6); C (O) -alkyl (Ci-Ce), C (O) -cycloalkyl (C3-C6); R3 is H, alkyl (C? -C6), F, CN, N3, O-alkyl (C? -C6), CH2-C00 alkyl (C? -C6), CH2-COO cycloalkyl (C3-C8), CH2 -C00H, CH2-CONH2, CH2-CONHCH3, CH2-C0N (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can ser = 0-5 and where phenyl, thienyl, pyridyl ,. Furyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C? -C3), OH, O-alkyl (C? -C6); alkynyl (C2-C6), alkenyl (C2-C6), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) NHCH3, C (0) N ( CH3) 2, OC (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) r-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0-5 and wherein phenyl, thienyl, pyridyl ,. furyl in each case can be substituted up to twice by Cl, F, CN, CF3 / alkyl (C? -C3), OH, O-alkyl (Cx-C6); R5 is alkyl (Ci-Cß), cycloalkyl (C3-d), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, (CH2) n-furyl, where n can be = 0 - and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C? -C3), OH, O-alkyl (C? -C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-, or -CH2-CH2-CH2-CH2-; or R6 is SO: > - (C6H4-4-CH3) or E) Y is a direct bond, -CH2- or -CH2-CH-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 is H, F, Cl, Br, I, CH3, CF3, O-alkyl (d-C3); R1 'is H, F, Cl, Br, I, N02; R2 is H; R3 is H, (C1-C3) alkyl; R4 is phenyl, where the phenyl radical can be substituted up to twice by F, Cl, Br, I, alkyl (Ci-Ce), cycloalkyl (C3-C6), O-alkyl (C1-C3), CF3, OCF3, 0-CH2-phenyl, COOH, COO-alkyl (C? -C6), COO-cycloalkyl (C3-d), CONH2; R5 is phenyl, where the phenyl radical can be substituted up to two times by F, Cl, Br, I, alkyl (Ci-d), cycloalkyl (C3-d), O-alkyl (d-C3), CF3, OCF3, 0-CH2-phenyl, COOH, COO-alkyl (C? -C6), COO-cycloalkyl (C3-C6), CONH2; or their physiologically tolerable salts and their physiologically functional derivatives. A compound of the formula I, according to claim 1 wherein A) Y is a direct bond, -CH 2; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 is CN, COOH, COO-alkyl (Ci-Ce), CONH2, CONH-alkyl (C? -C6), CON- [alkyl ((C? -d)] 2, (C2-C6) alkyl, alkenyl ( C2-C6), alkynyl (C2-C6), 0-CH2-CF3, 0-CH2-CF2-CF3, O-alkyl (C4-d), where in the alkyl radicals one or three or all the atoms of hydrogen can be replaced by fluorine, or a hydrogen can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (C00CH2Ph) 2; S-alkyl (Ci-d), S- ( CH?) N-phenyl, SO-alkyl (C? -C6), SO- (CH2) n-phenyl, where the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN , OCF3, O-alkyl (C? -C6), alkyl (C? -C6); NH-alkyl (Ci-Ce), N- ((C? -C6) alkyl, NH-acyl (C1-C7), phenyl, 0- (CH2) n-phenyl, where n can be = 0-6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings, in each case they can be substituted one to three times by F, Cl, I, OH, CF3, CN, OCF3, O-alkyl (C? -C6), alkyl (Ci-Ce), NH2, NH-alkyl (C? -C6), N- ((Ci-C6) alkyl) 2, COOH, COO-alkyl (Ci-Ce), CONH2; 1,2, 3-triazol-5-yl, where the triazole ring may be substituted in position 1, in position 2 or in position 3 for methyl or benzyl, tetrazol-5-yl, where the tetrazole ring may be substituted in position 1 or in position 2 by methyl or benzyl; Rl 'is H , F, Cl, Br, I, CH 3, CH 3, O-(C 1 -C 3) alkyl, SO-NH 2, SO ?NH-alkyl (Ci-Ce), S02N- [(C?-C6) alkyl] 2 or R 1, R 2 is H, alkyl (C 6 -C 6), (CH 2) n -phenyl, (CH 2) n-thienyl, (CH2) n-pit7-dityl, C (O) - (CH?) N-phenyl, C (0) - (CH2) n-thienyl, C (O) - (CH) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3 alkyl ( C1-C3), OH, O-alkyl (Ci-Ce); R3 is H, (C? -C6) alkyl, F, CN, O-alkyl (C? -C6), CH2-COO alkyl (C? -C6), CH2-COO cycloalkyl (C3-C8), CH2-COOH , CH: -CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0 -3 and where phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); alkynyl (dd), alkenyl (C2-C6), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) N (CH3) 2, 0C (0) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n -pyridyl, where n can be = 0-3 and where phenyl , thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (dC3), OH, O-alkyl (C6C6); R5 is alkyl (d-C6), cycloalkyl (C3-C6), (CH2) .- phenyl, (CH?) N-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl , thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (d.-C3), OH, O-alkyl (C? -C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2- or -CH2-CH2-CH2-; or B) Y is a direct link, -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 'independently among them are H, F, Cl, Br, I, CN, COOH, COO-alkyl (C? -C6), CONH2, CONH-alkyl (C? ~ C6), CON- [alkyl (( C? -C5)? 2, alkyl (Ci-d), alkenyl (C2-d), alkynyl (C2-d), O-alkyl (Ci-Ce), 0-CH2-CF3, 0-CH2-CF? -CF3, O-C4-C6 alkyl, where in the alkyl radicals one or several or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen atom can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (C00CH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, SO-alkyl (C? -C6), SO- (CH2) ) n-phenyl, wherein the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, OCF3l, O-alkyl (C? -C6), alkyl (C? -C6); S02-NH2, S02NH-alkyl (C? -C6), S02N- [(C? -C6) alkyl] 2, NH-alkyl (Ci-Ce), N- ((alkyl (Ci-d)?, NH -acyl (C1-C7), phenyl, O- (CH2) n-phenyl, where n can be = 0-6, 1-naphthyl or 2-naphthylc, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2- furanyl or 3-furanyl or 2-tieni or 3-thienyl, wherein the phenyl, naphthyl, pyridyl, furanyl or thienyl rings in each case may be substituted one to three times by F, Cl, I, OH, CF3, CN, OCF3, O-alkyl (d) - C6), alkyl (d-C6), NH2, NH-alkyl (C? -C6), N- (alkyl (C? -Ce)) 2, COOH, COO-alkyl (C? -C6), CONH2; • 1, 2, 3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R 2 is H, (C 1 -C 6) alkyl, (CH 2) n -phenyl, (CH 2) n-thienyl, (CH 2) n -pyridyl, C (O) - (CH 2) n -phenyl, C (O) - (CH2) n-thienyl, C (O) - (CH) n-pyridyl, where n can be = 0-3 and wherein phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F , CN, CF3, alkyl (d-C3), OH, O-alkyl (C? -C6); R3 is (C4-C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2- COO alkyl (Ci-Ce), CH2-COO cycloalkyl (C3-C8), CH2-COOH, CH2 -CONH2, CH2-CONHCH3, CH2-CON (CH3)?, (CH2) n-phenyl, (CH2) n-thienyl, (CH?) N-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C? -C3), OH, O-alkyl (C? -C6); alkynyl (dd), alkenyl (C? -C6), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH? C (0) NHCH3, C (0) N ( CH3) 2, 0C (0) CH3; R4 is (d-C6) alkyl, (C3-C6) cycloalkyl, (CH2) n-phenyl, (CH?) N-thienyl, (CH2) n-pyridyl, where n may be = O-3 and where phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C? -C6); R5 is alkyl (Ci-Ce), cycloalkyl (d-C6), • (CH2) n-phenyl, (CH2) n-thienyl, (CH2) r-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-; or C) Y is a direct link, or -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 ', independently of each other, are H, F, Cl, Br, I, CN, COOH, COO-alkyl (d-C6), CONH2, CONH-alkyl (C? -C6), CON- [alkyl ( (C? -C6)] 2, (C1-C0) alkyl, (C2-C6) alkenyl, (C2-d) alkynyl, -O-alkyl (C? -C6), 0-CH2-CF3, 0-CH2- CF2-CF3, O-alkyl (dd), wherein in the alkyl radicals one or more or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen can be replaced by OH, OC (0) CH3, 0 -CH2-Ph, NH2 or N (COOCH2Ph); S-alkyl (C? -C6), S- (CH2) n-phenyl, S02-alkyl (Ci-Ce), S02- (CH2) n-phenyl , where n can be = 0 - 6 and the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, OCF3, O-alkyl (C? -C6), alkyl (Ci-Ce), SO2-NH2, SO? NH-alkyl (C? -C6), S02N- [(C? -C6) alkyl] 2 / NH-alkyl (C? -C6), N- (alkyl) C? -d)) 2, NH-acyl (C1-C7), phenyl, 0- (CH2) n-phenyl, where n can be = 0-4, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the rings of phenyl, naphthyl, pyridyl, furanyl or thienyl in each case can be substituted from nail to 3 times by F, Cl, I, OH, CF3, CN, 0CF3, O-alkyl (C? -C6), alkyl (C? -C6), NH2, NH-alkyl (C? -C6), N- (alkyl (d-C6)) 2, COOH, COO-alkyl ( d-C6), C0NH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is alkyl (C? -C6), C2-C8 alkenyl, d-C6 alkynyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH?) N-pyridyl, C (O) - (CH) n-phenyl, C (O) - (CH2) n-thienyl, C (O) - (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C1-C3) , OH, O-alkyl (C? -C6); R3 is H, alkyl (C? -C6), F, CN, O-alkyl (C? -C6), CH2-COO alkyl (C? -C6), CH2-COO cycloalkyl (C3-C8), CH2-COOH , CH? -CONH2, CH2-CONHCH3, CH? -CON (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n -pyridyl, where n can be = 0 -3 and in wherein phenyl, thienyl, pyridyl, in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C? -C3), OH, O-alkyl (C? -C6); alkynyl (C2-d), alkenyl (C2-C6), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) N (CH3) 2, OC ( 0) CH3; R4 is alkyl (Ci-Ce), (C3-C6) cycloalkyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); R5 is alkyl (C? ~ C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl , thienyl, pyridyl, in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C? ~ C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, or -CH2-CH2-CH2-; or D) Y is a direct link, or -CH2-; X is CH (phenyl), where the phenyl radical can be substituted by F, Cl or Br, 0, S, SO, S02 or N-R6; R1 and R1 ', independently of each other, are H, F, Cl, Br, I, CN, COOH, COO-alkyl (C? -C6), C0NH2, CONH-alkyl (C? -C6), CON- [alkyl] ((d-C6)] 2, alkyl (Ci-Cß), alkenyl (C2-C6), alkynyl (C2-C6); O-alkyl (Ci-Ce), 0-CH2-CF3, 0-CH2-CF2 -CF3, O-alkyl (C-C6), where in the alkyl radicals one or several or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen can be replaced by OH, 0C (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (C? ~ C6), S- (CH2) n-phenyl, SO? -alkyl (C? -C6), S02- (CH2) r. ~ phenyl, where n can be = 0-6 and the phenyl radical can be substituted up to twice by F, Cl, Br, OH, CF3, N02, CN, 0CF3, O-alkyl (C? -C6), alkyl (Ci-Ce); SO2-NH2, S02NH-alkyl (C? -C6), S02N- [alkyl (d ~ d)] 2, NH. , NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, NH-acyl (C: -C7), phenyl, 0- (CH2) n-phenyl, where n can be = 0 - 6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, naphthyl, pyridyl rings , furanyl or thienyl in each case can be substituted from one to 3 times by F, Cl, I, OH, CF3, CN, OCF3, O-alkyl (C? -C6), alkyl (C? -C6), NH2, NH-alkyl (d-C6), N- (alkyl (d-Ce)) 2, COOH, COO-alkyl (C? -C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is H, alkyl (C? -C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, C (0) - (CH2) n-phenyl, C (0) - (CH2) n-thienyl, C (0) - (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl ( C? -C3), OH, O-alkyl (C? -C6); R3 is H, (C? -C6) alkyl, F, CN, O-alkyl (C? -C6), CH2-COO alkyl (C? -C6), CH2-C00 cycloalkyl (C3-C8), CH2-C00H , CH2-CONH2, CH2-CONHCH3, CH2-C0N (CH3) 2, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0 -3 and where phenyl , thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C? -C3), OH, O-alkyl (C? -C6); alkynyl (d-C6), alkenyl (d-C6), C (0) 0CH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) NHCH3, C (0) N ( CH3) 2, 0C (0) CH3; R4 is (d-C6) alkyl, (C3-C6) cycloalkyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); R5 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n -pyridyl, where n can be = 0-3 and where phenyl , thienyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2- or -CH2-CH2-CH2-; R6 is S02- (C6H4-4-CH3) or E) Y is a direct bond or -CH2-; X is CH2, CH (CH3), CH (C? H5), CH (C3H7); R 1 is H, F, Cl, Br, I, CH 3, CF 3, O-(C 1 -C 3) alkyl; R1 'is H, F, Cl, Br, I; R2 is H; R3 is H, (C1-C3) alkyl; R4 is phenyl, where the phenyl radical can be substituted up to twice by F, Cl, Br, I, alkyl (Ci-Ce), cycloalkyl (C3-C6), O-alkyl (C1-C3), CF3, OCF3, 0-CH2-phenyl, COOH, COO-alkyl (Ca-C6), CONH2; R5 is phenyl, where the phenyl radical can be substituted up to twice by F, Cl, Br, I, alkyl (C? -C6), cycloalkyl (C3-C6), O-alkyl (C1-C3), CF3, OCF3 , 0-CH? -phenyl, COOH, COO-alkyl (d-C6), CONH2; or their physiologically tolerable salts and physiologically functional derivatives. A compound of formula I, according to claim 1 or according to claim 2, wherein A) Y is a direct bond; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 is CN, COOH, COO-alkyl (C? -C6), CONH2, CON- [(C (-C?))] Alkyl, (C2-C6) alkyl, (C2-Cd) alkenyl, alkynyl (dd) 0-CH? -CF3, 0-CH2-CF2-CF3, O-alkyl (C4-C5), where in the aryl radicals one or more or all of the hydrogen atoms can be replaced by fluorine, or else a hydrogen can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, SO-alkyl (C? -C6), SO- (CH2) n-phenyl, where the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, OCF3 / O-alkyl (C? C6), alkyl (C? -C6), NH-alkyl (Ci-d), N- (alkyl (d-C6)) 2, NH-acyl (C1-C7), phenyl, O- (CH2) n- phenyl, where n can be = 0-6,1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the rings of phenyl, naphthyl, pyridyl, furanyl or thienyl in each case may be substituted one to two times by F, Cl, OH, CF3, CN, OCF3, O -alkyl (C? -C6), alkyl (C? -C6), COOH, COO-alkyl (d-C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R1 'is H, F, Cl, CH3, CF3, O-C1-C3 alkyl, S02-NH2, S02NH-alkyl (C6C6), S02N- [alkyl (dC6)] 2 or R1; R2 is H, alkyl (C? -C6), (CH?) N-phenyl, (CH2) n-pyridyl, C (O) - (CH: > r-phenyl, C (O) - (CH2) n -pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (C? -C6) ); C (O) -alkyl (Ci-C6); R3 is H, (C? -C6) alkyl, F, CN, O-alkyl (dd), CH2-COO alkyl (C? ~ C6), CH2-COO cycloalkyl (C3-C8), CH2-COOH, CH? -C0NH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, 0-alkyl (C6C6); alkynyl (C2-C6), C (0) 0CH3, C (0) OCH2CH3, C (0) 0H, C (0) NH2, C (0) N (CH3) 2, 0C (0) CH3; R4 is alkyl (Ci-d), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl, in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (C6C6); R5 is alkyl (C6C6), cycloalkyl (C3-C6), (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (Ci-Ce); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, or -CH? -CH2-CH2-; or B) Y is a direct link, -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 'independently of each other are H, F, Cl, Br, I, CN, COOH, COO-alkyl (C: -C6), CONH2, CON- [alkyl ((C? -C6)] 2, alkyl ( d-C6), alkenyl (C2-C6), alkynyl (C2-C6), O-alkyl (C6-6), 0-CH2-CF3, 0-CH2-CF2-CF3, O-alkyl (C4-C6) ), where in the alkyl radicals one or several or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (C00CH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, SO-alkyl (C? -C6), SO- (CH2) n-phenyl, where the phenyl radical may be substituted up to twice by F, Cl, OH, CF3, 0CF, 0-alkyl (Ci-Ce), alkyl (Ci-d), S02-NH2, S02NH-alkyl? (Ci-Ce), S02N- [alkyl (C) ? -C6)] 2, N- (alkyl (d-C6)) 2, NH-acyl (dd), phenyl, 0- (CH2) n-phenyl, where n can be = 0-6, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the phenyl, naphthyl, pyridyl, furanyl rings or thienyl in each case can be substituted from one to three times by F, Cl, Br, I, OH, CF3, CN, 0CF3, 0-alkyl (C? -C6), alkyl (C? -C6), NH2, N- (alkyl (C? -C6)) 2, COOH, COO-alkyl (Cx-C6), CONH2; 1, 2, 3-tr.iazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is H, alkyl (C? -C6), (CH2) n-phenyl, (CH2) n-pyridyl, C (O) - (CH2) n-phenyl, C (O) - (CH2) n-pyridyl, where n can be = O-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C? -C6); C (O) -alkyl (d-d); R3 is (C4-C6) alkyl, F, CN, N3, O-alkyl (C? -C6), CH2-COO alkyl (Ci-Ce), CH2-COO cycloalkyl (C3-C8), CH2-COOH, CH2 -CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n "phenyl, (CH2) n-pyridyl where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to two times by Cl, F, CN, CF3, (C1-C3) alkyl, 0-C6-C6 alkyl), (C2-C6) alkynyl, C (0) 0CH3, C (0) OCH2CH3, C (0) 0H , C (0) NH2, C (0) NHCH3, C (0) N (CH3) 2, 0C (0) CH3; R4 is (C? -C6) alkyl, (C3-C6) cycloalkyl, (CH2) n -phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (dd), O-alkyl (C? -C6); R5 is (C? -Ce) alkyl, (C3-C6) cycloalkyl, (CH2) n-phenyl,. {CH2) n-pyridyl, where n can be = 0-3 and in where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (d-C6), or R4 and R5 together form a group -CH2- CH2 -, -CH2-C (CH3) 2- or -CH2-CH2-CH2-; or C) Y is a direct link or -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 and R1 'independently of each other are H, F, Cl, Br, I, CN, COOH, COO-alkyl (C6C6), CONH2, CON- [alkyl ((C6C6)] 2, alkyl ( C? -C6), alkenyl (C2-d), alkynyl (C2-C6), O-alkyl (C? -C6), 0-CH2-CF3, O-CH2-CF? -CI3, O-alkyl (C4) -d), wherein in the alkyl radicals one or more or all of the hydrogen atoms can be replaced by fluorine, or a hydrogene can be replaced by OH, OC (0) CH3, O-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, S02-alkyl (C? -C6), S02- (CH2) r-phenyl, where n can be = 0-6 and the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, 0CF3, O-alkyl (d-C6), alkyl (Ci-C6); SO2-NH2, S02NH- alkyl (C? -C6), S02N- [(C? -C6) alkyl] 2, N- ((C? -C6) alkyl) 2, NH-acyl (C1-C7), phenyl, 0- (CH2) n-phenyl, where n can be = 0-4, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the rings of phenyl, naphthyl, pyridyl, furanyl or thienyl in each case can be substituted one to three times by F, Cl, I, OH, CF3, CN, 0CF3, O-alkyl (C? -C6), alkyl (Ci-Ce) ), NH2, NH-alkyl (C? -C6), N- ((C? -C6) alkyl) 2, COOH, COO-alkyl (C? -C6), CONH2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is alkyl (Ci-d), C2-C8 alkenyl, C2-Cs alkynyl, (CH2) n-phenyl, (CH2) n-thienyl, (CH2) n-pyridyl, C (O) - (CH2) n- phenyl, C (O) - (CH2) n-thienyl, C (O) - (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); C (O) -alkyl (C? -C6); R3 is H, alkyl (d-C6), F, CN, O-alkyl (C? -C6), CH2-COO alkyl (C? ~ C6), CH2-COO cycloalkyl (C3-C8), CH2-COOH, CH2-CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (C6C6); (C2-C6) alkynyl, C (O) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) N (CH3) 2, OC (0) CH3; R4 is alkyl (C? -C6), cycloalkyl (C3-Cd), (CH?) N-phenyl, (CH?) R.-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case may be substituted up to two times by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (Ci-Ce), 'R5 is aL- alkyl (Ci-Ce), (C3-C6) cycloalkyl, ( CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl, in each case can be substituted up to twice by Cl, F, CN, CF3, alkyl (C1-) C3), O-alkyl (Ci-Ce); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2- or -CH2-CH2-CH2-; or D) Y is a direct link, -CH2-; X is CH (phenyl), where the phenyl radical can be substituted by F or Cl, O, S, S02 or N-Rd; R1 and R1 'independently of each other are H, F, Cl, Br, I, CN, COOH, COO-alkyl (Ci-Ce), CONH ?, CON- [alkyl ((d-C6)] 2, alkyl (C) C6), alkenyl (C2-C6), alkynyl (C2-C6), O-alkyl (C? -Cd), 0-CH2-CF3, 0-CH2-CF2-CF3, O-alkyl (C4-C6) ), where in the alkyl radicals one or several or all of the hydrogen atoms can be replaced by fluorine, or a hydrogen can be replaced by OH, OC (0) CH3, O-CH2-Ph, NH2 or N (COOCH2Ph) 2; S-alkyl (C? -C6), S- (CH2) n-phenyl, S02-alkyl (Ci-d), S02- (CH2) n-phenyl, where n can be = 0-6 and the phenyl radical can be substituted up to two times by F, Cl, Br, OH, CF3, N02, CN, OCF3, O-alkyl (C? -C6), alkyl (Ci-Ce), S02-NH2, S02NH- alkyl (C? -C6), S02N- [alkyl (Cj-Ce)] 2, NH ?, N- (alkyl (d-C6)) 2, NH-acyl (C1-C7), phenyl, 0- (CH2 ) n-phenyl, where n can be = 0-6,1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl , where L The rings of phenyl, naphthyl, pyridyl, furanyl or thienyl in each case can be substituted one to three times by F, Cl, I, OH, CF3, CN, OCF3, O-alkyl (C? -Ce), alkyl (Ci) -Ce), NH2, N- (alkyl (C? -C6)) 2, COOH, COO-alkyl (d-C6), CONH?; 1, 2, 3-tr.Lazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R 2 is H, (C 1 -C 6) alkyl, (CH 2) n -phenyl, (CH 2) n-thienyl, (CH 2) n -pyridyl, C (0) - (CH 2) n -phenyl, C (O) - (CH2) n-thienyl, C (O) - (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, thienyl, pyridyl, furyl in each case can be substituted up to twice by Cl, F , CN, CF3, (C1-C3) alkyl, OH, O-alkyl (C6C6); C (0) -alkyl (Ci-Cg); R3 is H, (C? -C6) alkyl, F, CN, O-alkyl (C? -C6), CH2-COO alkyl (C? -C6), CH2-COO cycloalkyl (C3-C8), CH2-COOH , CH2-CONH2, CH2-CONHCH3, CH2-CON (CH3) 2, (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (d-Cd); alkynyl (C2-C6), C (0) OCH3, C (0) OCH2CH3, C (0) OH, C (0) NH2, C (0) NHCH3, C (0) N (CH3) 2, OC (0 ) CH3; R4 is alkyl (C6C6), cycloalkyl (C3-Cd), (CH2) n-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (C6C6); R5 is alkyl (Ci-d), cycloalkyl (C3-C6), (CH2) r-phenyl, (CH2) n-pyridyl, where n can be = 0-3 and where phenyl, pyridyl in each case can be substituted up to twice by Cl, F, CN, CF3, (C1-C3) alkyl, O-alkyl (C6C6); or R4 and R5 together form a group -CH2-CH2-, -CH2-C (CH3) 2-, -CH2-CH2-CH2-; R6 is S02- (CdH4-4-CH3) or E) Y is a direct bond or -CH2-; X is CH2, CH (CH3), CH (C2H5), CH (C3H7); R1 is H, F, Cl, CH3, CF3, O-alkyl (d-C3); R1 'is H, F, Cl; R2 is H; R3 is H, (C1-C3) alkyl; R 4 is phenyl, where the phenyl radical can be substituted up to twice by F, Cl, (C x -Cd) alkyl, (C 3 -C 6) cycloalkyl, O (C 1 -C 3) alkyl, CF 3, 0-CH 2 -phenyl, COOH, COO-alkyl (Ci-Ce), CONH2; R5 is phenyl, where the phenyl radical can be substituted up to two times by F, Cl, alkyl (Ci-), cycloalkyl (C3-C6), O-alkyl (d-C3), CF3, 0-CH2-phenyl, COOH , COO-alkyl (C? -C6), CONH2; or their physiologically tolerable salts and physiologically functional derivatives. A compound of formula I, according to claim 1, 2 or 3, wherein Y is a direct bond; X is CH2 R1 and R1 ', independently of each other, are H, F, Cl, CN, COOH, CONH2, COO- (C1-C3) alkyl, alkyl (C6-6), alkenyl (C2-C6), alkynyl (C2-Cd), wherein in the alkyl, alkenyl and alkynyl radicals, a hydrogene can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; OCF3, OCH2CF3, O-(C1-C4) alkyl, where in the alkyl radicals one or more or all of the hydrogen atoms may be replaced by fluorine or a hydrogen atom may be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (COOCH2Ph) 2; S02-alkyl (C? -C6), S02- (CH2) n-phenyl, where n can be = 0-3 and the phenyl radical can be substituted by F, Cl, OH, CF3, O-alkyl (C1-C4) ); NH- (CO) -alkyl (C1-C3); (CH2) n-phenyl, S- (CH2) n-phenyl, O- (CH2) n-enyl, where n can be = 0-3, 1-naphthyl or 2-naphthyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, 2-furanyl or 3-furanyl or 2-thienyl or 3-thienyl, where the rings phenyl, naphthyl, pyridyl, furanyl or thienyl in each case can be substituted by F, Cl, CF3, alkyl (C? -C6), O-alkyl (C? -C6) and where in the alkyl radicals a hydrogen atom can be replaced by OH, OC (0) CH3, 0-CH2-Ph, NH2 or N (C00CH2Ph) 2; 1,2,3-triazol-5-yl, wherein the triazole ring may be substituted at position 1, at position 2 or at position 3 by methyl or benzyl; tetrazol-5-yl, wherein the tetrazole ring may be substituted in the 1-position or in the 2-position by methyl or benzyl; R2 is H, alkyl (C? -C4), cycloalkyl (C5-Cd); (CH2) n-phenyl, where n can be = 0-3, C (O) -alkyl (C? -C4), or C (O) -phenyl; R3 is F, (C4-C6) alkyl, CH2-phenyl, where phenyl may be substituted up to two times by F, Cl, CF3, 0-alkyl (Ci-d) / (C1-C3) alkyl, COOH, CO- O-alkyl (d-C3) or C0NH2; R4 is (d-C6) alkyl, (C3-C6) cycloalkyl, (CH2) n-phenyl, where n may be = 0-3 and the phenyl radical may be substituted up to two times by F, Cl, O-alkyl ( C? -C4) or OH; R5 is alkyl (C? -Cd), cycloalkyl (C3-Ce), (CH2) n-phenyl, where n can be = 0-3 and the phenyl radical can be substituted up to two times by F, Cl, O-alkyl (C? -C4) or OH; or their physiologically tolerable salts. A compound of formula I according to one or more of claims 1 to 4, wherein R 1 means 6-C1 R 1 'signifies H 2 R 2 H 2 R 3 means F R 4 signifies CH 3 R 5 signifies CH 3 X signifies CH 2 Y means -One hydrochloride of The compounds of the formula I according to one or more of claims 1 to 5. A pharmaceutical agent comprising one or more of the compounds according to claim 1 or 6 of claim 1, wherein said pharmaceutical agent comprises one or more of the compounds according to claim 1 or more of the claims. 1 to 6 and one or more agents thinning. A compound according to claim 1 of claim 1 for use as a drug for the treatment of obesity. A compound as claimed in one or more of claims 1 to 6 for use as a drug for the prophylaxis or treatment of type II diabetes. A process for the production of a pharmaceutical agent comprising one or more of the claimed compounds in one or more of claims 1 to 6, which comprises mixing the active compound with a pharmaceutically suitable carrier and forming this mixture in a form adequate for its administration. The use of the compounds according to one or more of claims 1 to 6 for the production of a drug for the treatment of obesity. The use of the compounds according to one or more of claims 1 to 6 for the production of a drug for the prophylaxis or treatment of type II diabetes.