JPH01128974A - １，５−ベンゾチアゼピン誘導体の製法 - Google Patents

１，５−ベンゾチアゼピン誘導体の製法

Info

Publication number: JPH01128974A
Authority: JP; Japan
Prior art keywords: compound; lower alkyl; acid; reaction; dimethylamino
Prior art date: 1987-11-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP62287943A

Other languages

English (en)

Japanese (ja)

Inventor

Hirozumi Inoue

井上　博純

Tsunehiro Harada

原田　恒博

Masaaki Nagasawa

正明長澤

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Tanabe Seiyaku Co Ltd

Original Assignee

Tanabe Seiyaku Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-11-13

Filing date

1987-11-13

Publication date

1989-05-22

1987-11-13 Application filed by Tanabe Seiyaku Co Ltd filed Critical Tanabe Seiyaku Co Ltd

1987-11-13 Priority to JP62287943A priority Critical patent/JPH01128974A/ja

1988-11-01 Priority to FI885033A priority patent/FI92393C/fi

1988-11-04 Priority to IL8829688A priority patent/IL88296A/en

1988-11-08 Priority to FR8814577A priority patent/FR2623192A1/fr

1988-11-11 Priority to IE338788A priority patent/IE61196B1/en

1988-11-11 Priority to DK631888A priority patent/DK631888A/da

1988-11-11 Priority to IT8822602A priority patent/IT1230633B/it

1988-11-12 Priority to KR1019880014917A priority patent/KR890008122A/ko

1989-05-22 Publication of JPH01128974A publication Critical patent/JPH01128974A/ja

Status Pending legal-status Critical Current

Links

KJFRSZASZNLCDF-UHFFFAOYSA-N 1,5-benzothiazepine Chemical class S1C=CC=NC2=CC=CC=C12 KJFRSZASZNLCDF-UHFFFAOYSA-N 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title claims description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
239000000126 substance Substances 0.000 claims abstract 3
150000003839 salts Chemical class 0.000 claims description 10
238000007363 ring formation reaction Methods 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 22
238000006243 chemical reaction Methods 0.000 abstract description 19
239000002904 solvent Substances 0.000 abstract description 15
239000003795 chemical substances by application Substances 0.000 abstract description 10
239000002253 acid Substances 0.000 abstract description 7
150000004820 halides Chemical class 0.000 abstract description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 3
238000003402 intramolecular cyclocondensation reaction Methods 0.000 abstract description 3
150000005599 propionic acid derivatives Chemical class 0.000 abstract description 3
239000008096 xylene Substances 0.000 abstract description 3
230000002490 cerebral effect Effects 0.000 abstract description 2
230000000304 vasodilatating effect Effects 0.000 abstract description 2
230000005494 condensation Effects 0.000 abstract 2
238000009833 condensation Methods 0.000 abstract 2
208000001953 Hypotension Diseases 0.000 abstract 1
125000001589 carboacyl group Chemical group 0.000 abstract 1
239000003153 chemical reaction reagent Substances 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
208000021822 hypotensive Diseases 0.000 abstract 1
230000001077 hypotensive effect Effects 0.000 abstract 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
-1 diethylaminoethyl halide Chemical class 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
239000000203 mixture Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
239000002994 raw material Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000005907 alkyl ester group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
150000002688 maleic acid derivatives Chemical class 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000000034 method Methods 0.000 description 2
LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
ZNPNOVHKCAAQCG-UHFFFAOYSA-N 2-chloro-1-methylpyridin-1-ium Chemical compound C[N+]1=CC=CC=C1Cl ZNPNOVHKCAAQCG-UHFFFAOYSA-N 0.000 description 1
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylamino-1-chloro-ethane hydrochloride Natural products CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
MNZMECMQTYGSOI-UHFFFAOYSA-N acetic acid;hydron;bromide Chemical compound Br.CC(O)=O MNZMECMQTYGSOI-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
150000007932 benzotriazole esters Chemical class 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
KWUZCAVKPCRJPO-UHFFFAOYSA-N n-ethyl-4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound C1=CC(NCC)=CC=C1C1=NC2=CC=C(C)C=C2S1 KWUZCAVKPCRJPO-UHFFFAOYSA-N 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
230000006340 racemization Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000002747 voluntary effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP62287943A 1987-11-13 1987-11-13 １，５−ベンゾチアゼピン誘導体の製法 Pending JPH01128974A (ja)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
JP62287943A JPH01128974A (ja)	1987-11-13	1987-11-13	１，５−ベンゾチアゼピン誘導体の製法
FI885033A FI92393C (fi)	1987-11-13	1988-11-01	Menetelmä 1,5-bentsotiatsepiinijohdannaisten valmistamiseksi
IL8829688A IL88296A (en)	1987-11-13	1988-11-04	Preparation of a history of 1,5-benzothiazepine
FR8814577A FR2623192A1 (fr)	1987-11-13	1988-11-08	Procede pour preparer des derives de 1,5-benzothiazepine
IE338788A IE61196B1 (en)	1987-11-13	1988-11-11	Process for preparing 1,5-benzothiazepine derivatives
DK631888A DK631888A (da)	1987-11-13	1988-11-11	Fremgangsmaade til fremstilling af 1,5-benzothiazepinderivater
IT8822602A IT1230633B (it)	1987-11-13	1988-11-11	Procedimento per preparare derivati della 1,5 benzotiazepina.
KR1019880014917A KR890008122A (ko)	1987-11-13	1988-11-12	1,5-벤조티아제핀 유도체의 제조방법

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP62287943A JPH01128974A (ja)	1987-11-13	1987-11-13	１，５−ベンゾチアゼピン誘導体の製法

Publications (1)

Publication Number	Publication Date
JPH01128974A true JPH01128974A (ja)	1989-05-22

Family

ID=17723745

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62287943A Pending JPH01128974A (ja)	1987-11-13	1987-11-13	１，５−ベンゾチアゼピン誘導体の製法

Country Status (8)

Country	Link
JP (1)	JPH01128974A (fi)
KR (1)	KR890008122A (fi)
DK (1)	DK631888A (fi)
FI (1)	FI92393C (fi)
FR (1)	FR2623192A1 (fi)
IE (1)	IE61196B1 (fi)
IL (1)	IL88296A (fi)
IT (1)	IT1230633B (fi)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100292313B1 (ko) *	1993-01-27	2001-09-17	시오노 요시히코	벤조티아제핀유도체의제조방법

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL94295A0 (en) *	1989-05-25	1991-03-10	Fujisawa Pharmaceutical Co	Thiazepine derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59225174A (ja) *	1983-06-03	1984-12-18	Tanabe Seiyaku Co Ltd	ベンゾチアゼピン誘導体及びその製法
JPS60146884A (ja) *	1984-01-09	1985-08-02	Nippon Chem:Kk	１，５ベンゾチアゼピン誘導体の製造法
JPS60202871A (ja) *	1984-03-10	1985-10-14	Tanabe Seiyaku Co Ltd	１，５―ベンゾチアゼピン誘導体
JPS61103877A (ja) *	1984-10-24	1986-05-22	Tanabe Seiyaku Co Ltd	ベンゾチアゼピン誘導体及びその製法
JPS61122281A (ja) *	1984-11-17	1986-06-10	Tanabe Seiyaku Co Ltd	１，５―ベンゾチアゼピン誘導体

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58201773A (ja) *	1982-05-17	1983-11-24	Tokawa Tetsuo	ベンゾチアゼピン誘導体の製造法
JPS60109580A (ja) *	1983-11-16	1985-06-15	Roller Japan Kk	シス−ｄ−２−（４’−メトキシフェニル）−３−アセトキシ−５−（２−ジメチルアミノエチル）−２，３−ジヒドロ−１，５−ベンゾチアゼピン−４（５Ｈ）−オンまたはその塩の製法

1987
- 1987-11-13 JP JP62287943A patent/JPH01128974A/ja active Pending
1988
- 1988-11-01 FI FI885033A patent/FI92393C/fi not_active IP Right Cessation
- 1988-11-04 IL IL8829688A patent/IL88296A/en not_active IP Right Cessation
- 1988-11-08 FR FR8814577A patent/FR2623192A1/fr active Granted
- 1988-11-11 IE IE338788A patent/IE61196B1/en not_active IP Right Cessation
- 1988-11-11 IT IT8822602A patent/IT1230633B/it active
- 1988-11-11 DK DK631888A patent/DK631888A/da not_active Application Discontinuation
- 1988-11-12 KR KR1019880014917A patent/KR890008122A/ko not_active Application Discontinuation

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59225174A (ja) *	1983-06-03	1984-12-18	Tanabe Seiyaku Co Ltd	ベンゾチアゼピン誘導体及びその製法
JPS60146884A (ja) *	1984-01-09	1985-08-02	Nippon Chem:Kk	１，５ベンゾチアゼピン誘導体の製造法
JPS60202871A (ja) *	1984-03-10	1985-10-14	Tanabe Seiyaku Co Ltd	１，５―ベンゾチアゼピン誘導体
JPS61103877A (ja) *	1984-10-24	1986-05-22	Tanabe Seiyaku Co Ltd	ベンゾチアゼピン誘導体及びその製法
JPS61122281A (ja) *	1984-11-17	1986-06-10	Tanabe Seiyaku Co Ltd	１，５―ベンゾチアゼピン誘導体

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100292313B1 (ko) *	1993-01-27	2001-09-17	시오노 요시히코	벤조티아제핀유도체의제조방법

Also Published As

Publication number	Publication date
IT1230633B (it)	1991-10-28
DK631888A (da)	1989-05-14
FI885033A0 (fi)	1988-11-01
IL88296A0 (en)	1989-06-30
FI92393C (fi)	1994-11-10
FI885033A (fi)	1989-05-14
IE61196B1 (en)	1994-10-19
DK631888D0 (da)	1988-11-11
FR2623192A1 (fr)	1989-05-19
FR2623192B1 (fi)	1994-07-13
KR890008122A (ko)	1989-07-08
IE883387L (en)	1989-05-13
IT8822602A0 (it)	1988-11-11
IL88296A (en)	1995-03-15
FI92393B (fi)	1994-07-29

Publication	Publication Date	Title
JPS6317832B2 (fi)	1988-04-15
KR910005414B1 (ko)	1991-07-29	1,5-벤조티아제핀 유도체의 제조방법
CA1272717A (en)	1990-08-14	Naphthothiazepinones
JPH02288871A (ja)	1990-11-28	１，５‐ベンゾチアゼピン誘導体
CA2055326A1 (fr)	1992-05-15	Derives de la n-benzoyl proline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
DK171821B1 (da)	1997-06-23	9-chlor-1,5-benzothiazepinderivater, fremgangsmåde til fremstilling deraf samt farmaceutisk præparat indeholdende disse
FR2618150A1 (fr)	1989-01-20	Benzazepines 3-substituees a action therapeutique
JPH03271269A (ja)	1991-12-03	カルシウム管遮断剤の製造に用いるキラル中間体の分割法
JPH01128974A (ja)	1989-05-22	１，５−ベンゾチアゼピン誘導体の製法
FI84473B (fi)	1991-08-30	Foerfarande foer framstaellning av oktahydroindolderivat och mellanprodukter av framstaellningen.
JPS6322559A (ja)	1988-01-30	インド−ル誘導体の立体特異的合成法
US3218333A (en)	1965-11-16	Aryl indolyl alkenyl amines
NO324508B1 (no)	2007-11-05	Fremgangsmate for fremstilling av alkoksyfuranonaminderivater, forbindelser frembrakt ved fremgangsmaten og anvendelse av disse forbindelser
KR940011461B1 (ko)	1994-12-15	1,5-벤조티아제핀 유도체의 제조 방법
US4640930A (en)	1987-02-03	Naphtho(1,8-bc)-1,5-thiazocinones
JPS62161776A (ja)	1987-07-17	１，５−ベンゾチアゼピン誘導体の製法
JPS60185775A (ja)	1985-09-21	１，５‐ベンゾチアゼピン誘導体及びその製法
KR860000781B1 (ko)	1986-06-25	1,5-벤조티아제핀 유도체의 제조방법
JPH02289558A (ja)	1990-11-29	８位置換１，５―ベンゾチアゼピン誘導体
FI93009C (fi)	1995-02-10	Menetelmä 1,5-bentsotiatsepiinijohdannaisten valmistamiseksi
JPS6078973A (ja)	1985-05-04	１，５−ベンゾチアゼピン誘導体の製法
JP2551375B2 (ja)	1996-11-06	１，５−ベンゾチアゼピン誘導体の製法
JPS60146884A (ja)	1985-08-02	１，５ベンゾチアゼピン誘導体の製造法
FI56842C (fi)	1980-04-10	Saett att framstaella derivat av dl-7-aminodesacetoxicefalosporansyra
JPS61260059A (ja)	1986-11-18	プロピオン酸誘導体のｄ体の製造方法

JPH01128974A - １，５−ベンゾチアゼピン誘導体の製法 - Google Patents

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Citations (5)

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Patent Citations (5)

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