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SI9600050B - Substituted benzenesulphonyl ureas and thioureas, processes for the preparation thereof and use of pharmaceutical preparations on the basis of these compounds as well as medicines containing them - Google Patents

Substituted benzenesulphonyl ureas and thioureas, processes for the preparation thereof and use of pharmaceutical preparations on the basis of these compounds as well as medicines containing them Download PDF

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SI9600050B
SI9600050B SI9600050A SI9600050A SI9600050B SI 9600050 B SI9600050 B SI 9600050B SI 9600050 A SI9600050 A SI 9600050A SI 9600050 A SI9600050 A SI 9600050A SI 9600050 B SI9600050 B SI 9600050B
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carbon atoms
alkyl
hydrogen
formula
cycloalkyl
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SI9600050A
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SI9600050A (en
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Heinrich Englert
Uwe Gerlach
Dieter Mania
Heinz Goegelein
Joachim Kaiser
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Hoechst Ag
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Priority claimed from DE19505398A external-priority patent/DE19505398A1/de
Priority claimed from DE19522920A external-priority patent/DE19522920A1/de
Application filed by Hoechst Ag filed Critical Hoechst Ag
Publication of SI9600050A publication Critical patent/SI9600050A/sl
Publication of SI9600050B publication Critical patent/SI9600050B/sl

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/40—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of thiourea or isothiourea groups further bound to other hetero atoms
    • C07C335/42—Sulfonylthioureas; Sulfonylisothioureas
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/58—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • General Health & Medical Sciences (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (14)

  1. I Patentni zahtevki l. Substituirane benzensulfonilsečnine in -tiosečnine s formulo I
    R(3) N R(4) kjer pomenijo: R(l) vodik, alkil z 1, 2, 3, 4, 5, 6 ali 7 C-atomi, cikloalkil s 3, 4, 5, 6 ali 7 C-atomi; R(2) vodik, alkil z 1, 2, 3, 4, 5 ali 6 C-atomi, cikloalkil s 3, 4, 5 ali 6 C-atomi, ali (Ci-Cg)-verigo, v kateri je n C-atomov nadomeščenih s heteroatorru, npr. O, N, S (z n = 1-4), F, Cl; R(3) H, alkil z 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 ali 12 C-atomi, cikloalkil s 3, 4, 5, 6, 7, 8, 9 ali 10 C-atomi, fluoralkil z 1, 2, 3, 4, 5 ali 6 C-atomi, fluorcikioalkil s 3, 4, 5 ali 6 C-atomi, ali (Ci-Cio)-verigo, v kateri je n C-atomov nadomeščenih s heteroatomi, npr. O, N, S, (n = 1, 2, 3 ali 4), R(4) vodik, alkil z 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 ali 12 C-atomi, cikloalkil s 3, 4, 5, 6, 7, 8, 9 ali 10 C-atomi, fluoroalkil z 1, 2, 3, 4, 5 ali 6 C-atomi, fluorcikioalkil s 3, 4, 5 ali 6 C-atomi, ali (C[-C10)-verigo, v kateri je n C-atomov nadomeščenih s heteroatomi, npr. O, N, S, (n = 1, 2, 3 ali 4); ali R(3) m R(4) skupaj tvorita (Ch^-s-obroč, v katerem je lahko ena ali več izmed CH2-skupin nadomeščenih s heteroatomi; E kisik ali žveplo; X kisik ali žveplo; Y [CR(5)R(5')]m; R(5) in R(5) neodvisno drug od drugega vodik ali alkil z 1 ali 2 C-atomoma; pri čemer so členi [CR(5)R(5')] enaki ali različni; m 1, 2, 3 ali 4; kot tudi njihove farmacevtsko prenesljive soli. 2
  2. 2. Spojina s formulo I po zahtevku 1, označena s tem, da v njej pomenijo: R(l) vodik, alkil z 1, 2, 3, 4, 5, 6 ali 7 C-atomi, cikloalkil s 3, 4, 5, 6 ali 7 C-atomi; R(2) vodik, F, Cl, alkil z 1, 2, 3, 4, 5 ali 6 C-atomi, cikloalkil s 3, 4, 5 ali 6 C-atomi, ali (C2-C7)-verigo, v kateri so 1, 2, 3 ali 4 CH2-skupine nadomeščene s heteroatomi, npr. O, N ali S R(3) in R(4) enaka ali različna vodik, alkil z 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 ali 12 C-atomi, cikloalkil s 3, 4, 5, 6, 7, 8, 9 ali 10 C-atomi, fluoralkil z 1, 2, 3, 4, 5 ali 6 C-atomi, fluorcikloalkil s 3, 4, 5 ali 6 C-atomi, ali (Ci-Cio)-verigo, v kateri so 1, 2, 3 ali 4 CH2-skupine nadomeščene s heteroatomi O, S ali NH; ali R(3) in R(4) skupaj (CH2)2_8, kjer je lahko ena izmed CH2-skupin nadomeščena s heteroatomom O, S ali NH; E kisik ali žveplo; X kisik ali žveplo; Y [CR(5)R(5')]m; R(5) in R(5’) neodvisno drug od drugega vodik ali alkil z 1 ali 2 C-atomoma; pri čemer so členi [CR(5)R(5')] enaki ali različni; m 1, 2, 3 ali 4; kot tudi njihove farmacevtsko prenesljive soli.
  3. 3. Spojina s formulo I po vsaj enem od zahtevkov 1 ali 2, označena s tem, da v njej pomenijo: R(l) vodik, alkil z 1, 2, 3 ali 4 C-atomi, cikloalkil s 3, 4, 5, 6 ali 7 C-atomi; R(2) F, Cl, alkil z 1, 2, 3 ali 4 C-atomi, ali (C2-C7) -verigo, kjer so 1, 2, 3 ali 4 CH2-skupine nadomeščene heteroatomi O, S ali NH; R(3) in R(4) enaka ali različna vodik, alkil z 1, 2, 3, 4, 5, 6, 7, 8, 9 ali 10 C-atomi, cikloalkil s 3, 4, 5 ali 6 C-atomi, ali (CrCi0) verigo, kjer so 1, 2, 3 ali 4 CH2 skupine nadomeščene s heteroatomi O, S ali NH; ali 3 «! e R(3) in R(4) skupaj (CH2)2-7, kjer je ena izmed CH2-skupin lahko nadomeščena s heteroatomi O, S, NH; E kisik ali žveplo; X kisik ali žveplo; Y [CR(5)R(5')]m; R(5) m R(5') neodvisno drug od drugega vodik ali alkil z 1 ali 2 C-atomoma, pri čemer so členi [CR(5)R(5')] enaki ali različni; m 1, 2, 3 ali 4; kot tudi njihove farmacevtsko prenesljive soli.
  4. 4) I I kjer imajo R(2), R(3), R(4), X, in Y v zahtevku 1 navedene pomene in M predstavlja alkalijski ali zemljoalkalijski ion, presnovimo z R(l)-substituiranim izocianatom s formulo IV R(l) - N = C = O IV, kjer ima R(l) v zahtevku 1 navedeni pomen, v substituirano benzensulfonilsečnino la; ali da (b) benzensulfonilsečnino s formulo la
    I Q pripravimo iz aromatskega benzensulfonamida II ali njegove soli III z R(l)-substituiranim trikloracetamidom s formulo V Cl/:-C(C=0)NH-R(l) 7 v prisotnosti baze; ali da (c) benzensulfoniltiosečnino Ib
    I b pripravimo iz benzensulfonamida II ali njegove soli III in R(l)-substituiranega tioizocianata VI R(1)-N=C=S VI ali da (d) benzensulfonilsečnino s formulo la pripravimo s reakcijo presnove iz benzensulfoniltiosečnine s formulo Ib; ali da (e) benzensulfonilsečnino la pripravimo s presnovo amina s formulo R(1)-NH2 s benzensulfonilizocianatom s formulo VII n n R(J)
    V I I ali da (f) benzensulfoniltiosečnino Ib pripravimo s presnovo amina s formulo z benzensulfonilizotiocianatom s formulo VIII 8
    ali da (g) benzensulfonilsečnino la pripravimo iz benzensulfonilsečnine s formulo IX
    in R(3)R(4)NH s pomočjo dehidratacijskega sredstva ali aktiviranja s pomočjo halogenidov karboksilne kisline oz. tvorbo mešanih anhidridov; ali da (h) benzensulfoniltiosečnino Ib pripravimo iz benzensulfoniltiosečnine s formulo X
    in R(3)R(4)NH s pomočjo dehidratacijskega sredstva ali z aktiviranjem s pomočjo halogenidov karboksilne kisline oz. tvorbo mešanih anhidridov. « r r · « « p . * OjO Ο Ο ο » '·> Οβ 3 • ρ «e«r r7,->rri *»> Ί *» • r r r r, r · r r r »> f 1 >·» )Ί ·> j > e-·'··^ r · r r* > ’ ‘ ’ 1 f· r r r rr· Λ ’ ' 9
    4. Spojine s formulo I po zahtevku 1, označene s tem, da v njih pomenijo: R( 1) vodik, alkil z 1, 2, 3, 4, 5, 6 ali 7 C-atomi, cikloalkil s 3, 4, 5, 6 ali 7 C-atomi; R(2) alkoksi z 1, 2, 3, 4, 5 ali 6 C-atomi ali merkaptoalkil z 1, 2, 3, 4, 5 ali 6 C-atomi; R(3) H, alkil z 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 ali 12 C-atomi, cikloalkil s 3, 4, 5, 6, 7, 8, 9 ali 10 C-atomi fluoralkil z 1, 2, 3, 4, 5 ali 6 C-atomi, fluorcikloalkil s 3, 4, 5 ali 6 C-atomi ali (Ci-Ci0) verigo, v kateri je n C-atomov nadomeščenih s heteroatomi, npr. O, N, S, (n = 1, 2, 3 ali 4); R(4) vodik, alkil z 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 ali 12 C-atomi, cikloalkil z 3, 4, 5, 6, 7, 8, 9, ali 10 C-atomi, fluoralkil z 1, 2, 3, 4, 5 ali 6 C-atomi, fluorcikloalkil s 3, 4, 5 ali 6 C-atomi ali (Ci-Cio) verigo, v kateri je n C-atomov nadomeščenih s heteroatomi, npr. O, N, S, (n = 1, 2, 3 ali 4); ali R(3) in R(4) skupaj tvorita (CH2)2-8-obroč, v katerem je lahko ena ali več CH2-skupin nadomeščenih s heteroatomi; E kisik ali žveplo; X kisik ali žveplo; Y [CR(5)R(5')]m; R(5) in R(5') neodvisno drug od drugega vodik ali alkil z 1 ali 2 C-atomoma; 4 pri čemer so členi [CR(5)R(5')] enaki ali različni; m 1, 2, 3 ali 4; kot tudi njihove farmacevtsko prenesljive soli.
  5. 5. Spojina s formulo I po vsaj enem od zahtevkov 1 do 4, označena s tem, da v njej pomenijo: R(l) vodik, alkil z 1, 2, 3 ali 4 C-atomi, cikloalkil s 3 ali 4 C-atomi; R(2) metoksi ali etoksi; R(3) m R(4) enaka ali različna vodik, alkil s 3, 4, 5, 6, 7 ali 8 C-atomi, cikloalkil s 3, 4, 5 ali 6 C-atomi ali (C3.8H7.i7)-skupmo, kjer so 1, 2, 3 ali 4 CH2-skupine nadomeščene s heteroatomi O, S, NH; ali R(3) in R(4) skupaj (CH2)2-8-skupino, kjer je lahko ena izmed CH2-skupin nadomeščena s heteroatomi O, S, NH; E žveplo ali kisik; X kisik; Y [CR(5)R(5')]m; R(5) in R(5’) neodvisno drug od drugega vodik ali alkil z 1 ali 2 C-atomoma; pri čemer so členi [CR(5)R(5')] enaki ali različni; m 1 ali 2, kot tudi njihove farmacevtsko prenesljive soli.
  6. 6. Spojina s formulo I po vsaj enem od zahtevkov 1 do 5, označena s tem, da v njej pomenijo: R(l) vodik, alkil z 1, 2 ali 3 C-atomi ali cikloalkil s 3 C-atomi; R(2) metoksi ali etoksi; R(3) in R(4) 5 enaka ali različna vodik, alkil s 5, 6, 7 ali 8 C-atomi, cikloalkil s 5 ali 6 C-atomi ali (C5.8Hii.i7)-skupino, kjer so 1, 2, 3 ali 4 CH2-skupine nadomeščene s heteroatomi O, S, NH; ali R(3) m R(4) skupaj (CH2)s.g, kjer je lahko ena izmed CH2-skupin nadomeščena s heteroatomi O, S, NH; E žveplo ali kisik; X kisik; Y [CR(5)R(5')]m; R(5) m R(5') neodvisno drug od drugega vodik ali metil; pri čemer so členi [CR(5)R(5')] enaki ali različni; m 1 ali 2, kot tudi njihove farmacevtsko prenesljive soli.
  7. 7. Spojina s formulo I po vsaj enem od zahtevkov 1 do 6, označena s tem, da v njej pomenijo: R(l) vodik, alkil z 1, 2 ali 3 C-atomi ali cikloalkil s 3 C-atomi; R(2) metoksi ali etoksi; R(3) vodik; R(4) alkil s 5, 6,1 ali 8 C-atomi, cikloalkil s 5 ali 6 C-atomi ali (Cs.gHi i„n)-skupino, v kateri so 1, 2, 3 ali 4 CH2-skupine nadomeščene s heteroatomi O, S, NH; E žveplo ali kisik; X kisik; Y [CR(5)R(5')]m; R(5) in R(5') neodvisno drug od drugega vodik ali metil; pri čemer so členi [CR(5)R(5')] enaki ali različni; m 1 ali 2, kot tudi njihove farmacevtsko prenesljive soli.
  8. 8. 6 Postopek za pripravo spojine s formulo I po zahtevku 1, označen s tem, da (a) sulfonamid s formulo II 8. 6
    ali njegovo sol s formulo III
  9. 9. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje motenj srčnega ritma.
  10. 10. Uporaba spojine I po zahtevku 1 za pripravo zdravila za preprečevanje nenadne smrti srca.
  11. 11. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje ishemičnih stanj srca.
  12. . 12. Uporaba spojine I po zahtevku 1 za pripravo zdravila za zdravljenje oslabljene moči srca.
  13. 13. Uporaba spojine I po zahtevku 1 za pripravo zdravila za izboljšanje srčne funkcije po transplantaciji srca.
  14. 14. Zdravilo, označeno s tem, da vsebuje učinkovito količino spojine s formulo I po enem ali več zahtevkih 1 do 7.
SI9600050A 1995-02-17 1996-02-16 Substituted benzenesulphonyl ureas and thioureas, processes for the preparation thereof and use of pharmaceutical preparations on the basis of these compounds as well as medicines containing them SI9600050B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19505398A DE19505398A1 (de) 1995-02-17 1995-02-17 Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung und Verwendung pharmazeutischer Präparate auf Basis dieser Verbindungen sowie sie enthaltende Heilmittel
DE19522920A DE19522920A1 (de) 1995-06-23 1995-06-23 Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung und Verwendung pharmazeutischer Präparate auf Basis dieser Verbindungen sowie sie enthaltende Heilmittel

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SI9600050A SI9600050A (en) 1996-10-31
SI9600050B true SI9600050B (en) 2001-12-31

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DE19546736A1 (de) * 1995-12-14 1997-06-19 Hoechst Ag Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Präparate
DK1270565T3 (da) * 1997-01-29 2004-10-04 Pfizer 4-substitueret furan-2-sulfonamid og dets anvendelse i fremstillingen af sulfonylurinstofderivater
DE19832009A1 (de) 1998-07-16 2000-01-20 Hoechst Marion Roussel De Gmbh 2,5-Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharamazeutische Präparate
DE10129704A1 (de) * 2001-06-22 2003-01-02 Aventis Pharma Gmbh Verwendung von Benzolsulfonyl(thio)harnstoffen in der Behandlung des septischen Schocks
KR100895167B1 (ko) * 2004-11-22 2009-05-04 일라이 릴리 앤드 캄파니 글루타메이트 수용체의 증강제
CN104649945B (zh) * 2015-02-05 2017-02-22 中国农业大学 一种磺酰脲类、磺酰胺基甲酸酯类化合物的制备方法
WO2023020412A1 (zh) * 2021-08-16 2023-02-23 中国科学院上海药物研究所 磺酰脲化合物、制备方法及其应用

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DE1198354B (de) * 1963-09-25 1965-08-12 Hoechst Ag Verfahren zur Herstellung von Benzol-sulfonylharnstoffen
DE1185180B (de) * 1963-10-19 1965-01-14 Hoechst Ag Verfahren zur Herstellung von Benzolsulfonylharnstoffen
BE754454A (fr) * 1969-08-06 1971-02-05 Bayer Ag Nouveaux composes hypoglycemiques du type d'arylsulfonylurees et d'arylsulfonylsemicarbazides contenant des groupes carbonamide
DE2413514C3 (de) * 1974-03-21 1982-03-04 Hoechst Ag, 6000 Frankfurt N-Acylaminoathylbenzolsulfonyl-N'-methylharnstoffe, Verfahren zu ihrer Herstellung und deren Verwendung
ES2098069T3 (es) * 1993-02-23 1997-04-16 Hoechst Ag Bencenosulfonil-ureas y -tioureas sustituidas, procedimiento para su preparacion y su utilizacion como agentes farmaceuticos.

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IL117152A (en) 2002-07-25
DK0727417T3 (da) 2001-07-09
ES2155546T3 (es) 2001-05-16
HUT73982A (en) 1996-10-28
SK282131B6 (sk) 2001-11-06
KR100432259B1 (ko) 2004-09-18
HU226462B1 (en) 2008-12-29
BR9600779A (pt) 1997-12-23
US5977177A (en) 1999-11-02
FI120391B (fi) 2009-10-15
HRP960076B1 (en) 2001-12-31
NO960628D0 (no) 1996-02-16
NZ280992A (en) 1996-10-28
CZ43596A3 (en) 1996-09-11
TW357141B (en) 1999-05-01
SK21296A3 (en) 1996-10-02
AR002708A1 (es) 1998-04-29
CA2169696A1 (en) 1996-08-18
AU700254B2 (en) 1998-12-24
GR3035710T3 (en) 2001-07-31
PT727417E (pt) 2001-08-30
EP0727417A1 (de) 1996-08-21
MY115795A (en) 2003-09-30
JPH08245556A (ja) 1996-09-24
CN1060162C (zh) 2001-01-03
CN1134415A (zh) 1996-10-30
ATE199541T1 (de) 2001-03-15
CZ291793B6 (cs) 2003-05-14
EP0727417B1 (de) 2001-03-07
NO960628L (no) 1996-08-19
HU9503877D0 (en) 1996-02-28
JP3905573B2 (ja) 2007-04-18
US5880155A (en) 1999-03-09
FI960688A0 (fi) 1996-02-15
PL181792B1 (pl) 2001-09-28
AU4555996A (en) 1996-08-29
PL312530A1 (en) 1996-08-19
IL117152A0 (en) 1996-06-18
FI960688A (fi) 1996-08-18
SI9600050A (en) 1996-10-31
CA2169696C (en) 2008-09-02
KR960031432A (ko) 1996-09-17
HRP960076A2 (en) 1997-12-31
DE59606531D1 (de) 2001-04-12
TR199600117A2 (tr) 1996-10-21
RU2198872C2 (ru) 2003-02-20
NO305795B1 (no) 1999-07-26

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