KR910020019A - 신규 피리도[2,3-f][1,4]티아제핀 및 피리도[3,2-b][1,5]벤조티아제핀 - Google Patents
신규 피리도[2,3-f][1,4]티아제핀 및 피리도[3,2-b][1,5]벤조티아제핀 Download PDFInfo
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- JROBKLYZJGATCR-UHFFFAOYSA-N pyrido[2,3-f][1,4]thiazepine Chemical compound S1C=CN=CC2=NC=CC=C12 JROBKLYZJGATCR-UHFFFAOYSA-N 0.000 title 1
- BYUYCWQSIZPKCS-UHFFFAOYSA-N pyrido[3,2-b][1,5]benzothiazepine Chemical compound C1=NC2=CC=CC=C2SC2=CC=CN=C21 BYUYCWQSIZPKCS-UHFFFAOYSA-N 0.000 title 1
- -1 3-piperidyl Chemical group 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 238000000034 method Methods 0.000 claims 7
- 206010020751 Hypersensitivity Diseases 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 6
- 208000026935 allergic disease Diseases 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 206010002383 Angina Pectoris Diseases 0.000 claims 3
- 206010003591 Ataxia Diseases 0.000 claims 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 208000005872 Diffuse Esophageal Spasm Diseases 0.000 claims 3
- 208000005171 Dysmenorrhea Diseases 0.000 claims 3
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 3
- 208000010412 Glaucoma Diseases 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- 208000019695 Migraine disease Diseases 0.000 claims 3
- 208000026723 Urinary tract disease Diseases 0.000 claims 3
- 208000012931 Urologic disease Diseases 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000000443 aerosol Substances 0.000 claims 3
- 230000007815 allergy Effects 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 230000009610 hypersensitivity Effects 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 3
- 206010027599 migraine Diseases 0.000 claims 3
- 208000010125 myocardial infarction Diseases 0.000 claims 3
- 238000007911 parenteral administration Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 208000014001 urinary system disease Diseases 0.000 claims 3
- YTLYLLTVENPWFT-UHFFFAOYSA-N 3-aminoprop-2-enoic acid Chemical class NC=CC(O)=O YTLYLLTVENPWFT-UHFFFAOYSA-N 0.000 claims 2
- 239000003810 Jones reagent Substances 0.000 claims 2
- 206010030184 Oesophageal spasm Diseases 0.000 claims 2
- 208000005107 Premature Birth Diseases 0.000 claims 2
- 206010036590 Premature baby Diseases 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 230000005176 gastrointestinal motility Effects 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- PSYYHKIRDZMRAC-UHFFFAOYSA-N 1$l^{4},2-benzothiazepine 1-oxide Chemical compound O=S1N=CC=CC2=CC=CC=C12 PSYYHKIRDZMRAC-UHFFFAOYSA-N 0.000 claims 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims 1
- RMAVOSJMKWAVDS-UHFFFAOYSA-N 1,5-benzothiazepine-3-carboxylic acid Chemical compound S1C=C(C=NC2=C1C=CC=C2)C(=O)O RMAVOSJMKWAVDS-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 241000283690 Bos taurus Species 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000005333 aroyloxy group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- 235000013601 eggs Nutrition 0.000 claims 1
- MNKLWGCKDGHWQQ-UHFFFAOYSA-N ethyl 1-(2,3-dichlorophenyl)-3,6-dimethyl-11,11-dioxo-4,5-dihydro-1h-pyrido[3,2-b][1,5]benzothiazepine-2-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(CN(C)C2=CC=CC=C2S2(=O)=O)=C2C1C1=CC=CC(Cl)=C1Cl MNKLWGCKDGHWQQ-UHFFFAOYSA-N 0.000 claims 1
- BLZCGSVESDCPOY-UHFFFAOYSA-N ethyl 1-(2,3-dichlorophenyl)-6-formyl-3-methyl-11,11-dioxo-4,5-dihydro-1h-pyrido[3,2-b][1,5]benzothiazepine-2-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(CN(C2=CC=CC=C2S2(=O)=O)C=O)=C2C1C1=CC=CC(Cl)=C1Cl BLZCGSVESDCPOY-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 230000002028 premature Effects 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- NGDIAZZSCVVCEW-UHFFFAOYSA-M sodium;butyl sulfate Chemical compound [Na+].CCCCOS([O-])(=O)=O NGDIAZZSCVVCEW-UHFFFAOYSA-M 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims 1
- GSJJCZSHYJNRPN-UHFFFAOYSA-N tert-butyl n-(2-sulfanylethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCS GSJJCZSHYJNRPN-UHFFFAOYSA-N 0.000 claims 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (14)
- 하기 일반식(Ⅰ)의 화합물 및 그의 거울상 이성질체 또는 약학적으로 허용되는 그의 염.상기식에서, Y 및 Z는 CH2이거나 Y 와 Z 는 함께 페닐 고리를 형성할 수 있고, R1은 수소, 아미노, C1-C8직쇄 또는 측쇄 알킬, 트리플루오로 메틸 또는 알콕시메틸이고, R2는 C1-C8직쇄 또는 측쇄 알킬, 치환알킬, 벤질, 3-피페리딜, N-치환 3-피페리딜 또는 N-치환 2-피롤리디닐 메틸렌이고, 여기에서 상기 N-치환 3-피페리딜 및 N-치환 2-피롤리디닐 메틸렌은 C1-C8직쇄 또는 측쇄 알킬, 또는 벤질로 치환되고, 상기 치환알킬은 C1-C8알콕시, 알카노일옥시, 아르알카노일옥시, 아로일옥시, 하이드록시, 할로겐, P-토실옥시, 아미노, 카르보알콕시 또는 NR5R6로 치환되고, R3는 2-피리딜, 3-피리딜, 2-티에닐, 3-티에닐, 2,1,3-벤즈옥사 디아졸릴, 2,1,3-벤즈티아디아졸릴 또는 치환 페닐이고, 여기에서 상기 치환 페닐은 수소, C1-C8직쇄 또는 측쇄 알킬, C1-C8알콕시, 시아노, 카르보알콕시, C1-C8알킬티오, 디플루오로 메톡시, 디플루오로메틸티오, C1-C8알킬술포닐, 할로겐, 니트로 또는 트리플루오로메틸로 위치 2-6의 어느 하나에 치환되고, R4는 수소, C1-C8직쇄 또는 측쇄 알킬, C3-C7시클로알킬, 아릴. 벤질, 치환 벤질, 포르밀, 아세틸, t-부틸옥시 카르보닐, 프로피오닐, 치환 알킬 또는 R7CH2C=O이고, 여기에서 상기 치환 벤질은 할로겐, 드리플루오로메틸, C1-C8직쇄 또는 측쇄 알킬 또는 C1-C8알콕시이고, 상기 치환 알킬은 아미노, 디알킬 아미노, C1-C8알콕시, 히이드록시 또는 할로겐으로 치환될 수 있고, R5및 R6는 동일하거나 상이할 수 있고, 수소, C1-C8직쇄 또는 측쇄 알킬, C3-C7시클로알킬, 페닐, 벤질, 펜에틸이거나, R5및 R6는 함께 피페리디노, 피롤리디노, 모르폴리노, 티오모르폴리노, 피페라지노 또는 상기 헤테로고리의 N-치환 유도체로 구성된 군으로 부터 선택된 헤테로고리이고, 여기에서 상기 N-치환 헤테로고리는 수소, C1-C8직쇄 또는 측쇄 알킬, 벤질, 벤즈히드릴, 페닐 또는 치환 페닐로 치환되고, 여기에서 상기 페닐은 수소, C1-C8직쇄 또는 측쇄 알킬, C1-C8알콕시, 할로겐, 니트로 또는 트리플루오로메틸로 치환되고, R7은 아미노, 디알킬 아미노, C1-C8알콕시, 히이드록시 또는 할로겐이고, n은 1 내지 4이다.
- 제1항에 있어서, R1이 메틸이고, R2가 에틸 또는 치환된 알킬이고, R3가 치환된 페닐이고, R4가 수소, C1-C8직쇄 또는 측쇄 알킬, 벤질, 포르밀, t-부틸옥시 카르보닐 또는 R7CH2C=O이고, R7이 아미노이고, n이 1임을 특징으로 하는 조성물.
- 제1항에 있어서, 하기 화합물들로 구성된 군으로부터 선택됨을 특징으로 하는화합물.a. 2-(N-벤질-N.-메틸아미노)에틸 9-(2,3-디클로로페닐)-1,1-디옥소-2,3,4,5,6,9-헥사히드로-7-메틸-피리도[2,3,-f][1,4]티아제핀-8-카르복실레이트, b. 2-(N-벤질-N-메틸아미노)에틸 9-(2,3-디클로로페닐)-4,7-디메틸-1,1-디옥소-2,3,4,5,6,9-헥사히드로피리도[2,3-f][1,4]티아제핀-8-카드복실레이트, c. 에틸 9-(2,3-디클로로페닐)-1,1-디옥소-2,3,4,5,6,9-헥사히드로-7-메틸-피리도[2,3,-f][1,4]티아제핀-8-카르복실레이트, d. 에틸 9-(2,3-디클로로페닐)-1,1-디옥소-4-에틸-2,3,4,5,6,9-헥사히드로-7-메틸-피리도[2,3,-f][1,4]티아제핀-8-카르복실레이트. e.에틸9-(2,3-디클로로페닐)-4,7-디메틸-1,1-디옥소-2,3,4,5,6,9-헥사히드로-파리도티아제핀-8-카르복실레이트. f. 에틸 4,7-디메틸-1,1-디옥소-2,3,4,5,6,9-헥사히드로-9-(2,3,4,5,6-펜타플루오로페닐)-피리도[2,3,-f][1,4]티아제핀-8-카르복실레이트. g. 에틸 1,1-디옥소-2,3,4,5,6,9-헥사히드로-7-메틸-9-(2,3,4,5,6-펜타플루오페닐)-피리도[2,3,-f][1,4]티아제핀-8-카르복실레이트. h.에틸1,1-디옥소-4-에틸-2,3,4,5,6,9-헥사히드로-7-메틸-9-(3-니트로페닐)-피리도[2,3,-f][1,4]티아제핀-8-카르복실레이트.i. 에틸 4-(2,3-디클로로페닐)-5,5-디옥소-10-포르밀-2-메틸-1,4,10,11-테트라히드로피리도[3,2-b][1,5]벤조티아제핀-3-카르복실레이트, j. 2-아세톡시에틸 9-(2,3-디클로로페닐)-4,7-디메틸-1,1-디옥소-2,3,4,5,6,9-헥사히드로피리도-[2,3,-f][1,4]티아제핀-8-카르복실레이트. k. 2-피발로일옥시에틸 9-(2,3-디클로로페닐)-4,7-디메틸-1,1-디옥소-2,3,4,5,6,9-헥사히드로피리도-[2,3,-f][1,4]티아제핀-8-카르복실레이트. ℓ. 에틸-4-(2,3-디클로로페닐)-2,10-디메틸-5,5,-디옥소-1,4,10,11-테트라히드로피리도[3,2-b][1,5]벤조티아제핀-3-카르복실레이트, m. 2-(N-벤질-N.-메틸아미노)에틸 4-(2,3-디클로로페닐)-2,10-디메틸-5,5-디옥소-1,4,10,11-테트라히드로피리도[3,2-b][1,5]벤조티아제핀-3-카르복실레이트. n.2-(N,N-메틸아미노)에틸4-(2,3-디클로로페닐)-4,7-디메틸-1,1-디옥소-2,3,4,5,6,9-헥사히드로피리도[2,3-f][1,4]티아제핀-8-카르복실레이트. o. 2-(N-벤질-N-메틸아미노)에틸 4-(2,3-디클로페닐)-4-디메틸-1,1-디옥소-2,3,4,5,6,9-헥사히드로-7-메틸-피리도[2,3-f][1,4]티아제핀-8-카르복실레이트. 및 p. (N-벤질-2-피롤리디닐)메틸9-(2,3-디클로로페닐)-4,7-디메틸-1,1-디옥소-2,3,4,5,6,9-헥사히드로-피리도[2,3-f][1,4]티아제핀-8-카드복실레이트.
- 활성 성분으로서 유효량의 제1항의 화합물과 적당한 약학적 담체를 함유하는 약학 조성물.
- 활성 성분으로서 유효량의 제2항의 화합물과 적당한 약학적 담체를 함유하는 약학 조성물.
- 활성 성분으로서 유효량의 제3항의 화합물과 적당한 약학적 담체를 함유하는 약학 조성물.
- a. 시스타민 디히드로클로라이드를 디-t-부틸 디카르보네이트로 처리하여 비스N-(t-부틸옥시카르보닐)-시스타민을 제조하고, b. 상기 비스(t-부틸옥시카르보닐)-시스타민 NaBH4로처리하여N-(t-부틸옥시카르보닐)-2-아미노에탄 티올을제조하고, c.-N-(t-부틸옥시카르보닐)-2-아미노에탄 티올을 에피클로로 히드린과 반응시켜 하기 일반식(Ⅱ)의 중간체 클로로히드린을 제조하고, d. 상기 중간체 클로로히드린을 하기 일반식(Ⅲ)의 에폭사이드를 통해 고리화하여 하기 일반식(Ⅳ)의 티아제피놀을 제조하고, e. 상기 티아제피놀을 m-클로로퍼옥시벤조산으로 산화시켜, 1.1-디옥소-티아제피놀을 제조하고, f. 상기 1.1-디옥소-티아제피논을 존스(Jones)시약으로 더 산화시켜 하기 일반식(Ⅴ)의 1.1--디옥소-티아제피놀을 제조하고, g. 상기 1.1-디옥스-티아제피논을 R3-치환된 알데히드 및 하기 일반식(Ⅵ)의 치환된 3-아미노아크릴레이트 유도체와 반응시켜 하기 일반식(Ⅶ)의 히드로피리딘을 제조하는 단계들을 특징으로 하는, Y 및 Z가 CH2인 제1항의 화합물 합성방법.상기식에서, R1, R2, R3및 R4는 제1항에서 정의된 것과 같고 t-BuO는 t-부틸옥시 보호기이다.
- a. 하기 일반식(Ⅷ)의 벤조티아제피논을 NaBH4m-클로로피옥시 벤조산 및 존스시약과 반응시켜 하기 일반식(IⅩ)의 1.1-디옥소벤조티아제페논을 제조하고, b. 상기 1.1-디옥소-벤조티아제페논을 R3-치한된 알데히드 및 하기 일반식(Ⅵ)의 치환된 3-아미노아크릴레이트 유도체와 반응시켜 하기 일반식(Ⅹ)의 디히드로피리딘을 제조하는 단계들을 특징으로 하는, Y 및 Z가 함께 페닐 고리를 형성한 제1항의 화합물의 합성방법.상기식에서, R1, R2, R3및 R4는 제1항에서 정의된 것과 같다.
- 유효량의 제1항의 화합물을 경구 또는 비경구 투여함으로써 포유동물에 있어서, 고혈압, 국소빈혈, 협심증, 울혈성 심부전, 편두통, 심근경색증 및 졸증을 포함한 심혈관 질환을 치료하는 방법.
- 유효량의 제2항의 화합물을 경구 또는 비경구 투여함으로써 포유동물에 있어서, 고혈압, 국소빈혈, 협심증, 울혈성 심부전, 편두통, 심근경색증 및 졸증을 포함한 심혈관 질환을 치료하는 방법.
- 유효량의 제3항의 화합물을 경구 또는 비경구 투여함으로써 포유동물에 있어서, 고혈압, 국소빈혈, 협심증, 울혈성 심부전, 편두통, 심근경색증 및 졸증을 포함한 심혈관 질환을 치료하는 방법.
- 유효량의 제1항의 화합물을 경구, 비경구적으로 또는 에어로졸에 의해 투여함으로써 포유동물에 있어서, 과민증, 알레르기, 천식, 월경불순, 식도경련, 위장운동질환, 녹내장, 조산 또는 요로 질환을 치료하는 방법.
- 유효량의 제2항의 화합물을 경구, 비경구적으로 또는 에어로졸에 의해 투여함으로써 포유동물에 있어서, 과민증, 알레르기, 천식, 월경불순, 식도경련, 위장운동질환, 녹내장, 조산 또는 요로 질환을 치료하는 방법.
- 유효량의 제3항의 화합물을 경구, 비경구적으로 또는 에어로졸에 의해 투여함으로써 포유동물에 있어서, 과민증, 알레르기, 천식, 월경불순, 식도경련, 위장운동질환, 녹내장, 조산 또는 요로 질환을 치료하는 방법※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
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| US07/518,351 US5075440A (en) | 1990-05-03 | 1990-05-03 | Novel pyrido[2,3-f](1,4)thiazepines and pyrido[3,2-b](1,5)benzothiazepines |
| US518,351 | 1990-05-03 |
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| US6593335B1 (en) | 1997-12-18 | 2003-07-15 | Abbott Laboratories | Potassium channel openers |
| US6265417B1 (en) | 1997-12-18 | 2001-07-24 | Abbott Laboratories | Potassium channel openers |
| ES2222000T3 (es) * | 1997-12-18 | 2005-01-16 | Abbott Laboratories | Compuestos que abren los canales de potasio. |
| JPH11193289A (ja) * | 1997-12-26 | 1999-07-21 | Suntory Ltd | ピロールスルホンアミド誘導体 |
| US6482854B1 (en) * | 1999-03-25 | 2002-11-19 | Massachusetts Eye And Ear Infirmary | Glaucoma treatment |
| US7015212B1 (en) | 1999-05-12 | 2006-03-21 | The United States Of America As Represented By The Department Of Health And Human Services | Thiazepine inhibitors of HIV-1 integrase |
| AU771033B2 (en) * | 1999-06-14 | 2004-03-11 | Ortho-Mcneil Pharmaceutical, Inc. | Dithiepino(6,5-b)pyridines, and related compositions and methods |
| IL147540A0 (en) | 1999-07-12 | 2002-08-14 | Ortho Mcneil Pharm Inc | OXATHIEPINO [6,5-b] DIHYDROPYRIDINES, AND RELATED COMPOSITIONS AND METHODS |
| AU7102700A (en) | 1999-09-22 | 2001-04-24 | Ortho-Mcneil Pharmaceutical, Inc. | Benzo-fused dithiepino[6,5-b]pyridines, and related compositions and methods |
| JP2003519626A (ja) * | 2000-01-12 | 2003-06-24 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | カルシウムアンタゴニスト活性を有するベンゾスルホン類 |
| WO2001055152A1 (en) * | 2000-01-27 | 2001-08-02 | Ortho-Mcneil Pharmaceutical, Inc.. | BENZOXATHIEPINO[3,4-b]PYRIDINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS MEDICAMENTS |
| JP2003528104A (ja) | 2000-03-23 | 2003-09-24 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | チエピノ［３，２−ｂ］ジヒドロピリジンおよび関連組成物ならびに方法 |
| JP2003535096A (ja) | 2000-05-30 | 2003-11-25 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | ジヒドロピリジンソフトドラッグならびに関連する組成物及び方法 |
| KR101233139B1 (ko) | 2011-04-21 | 2013-02-21 | 주식회사 한서켐 | 라세믹 1,4-티아제핀 화합물의 분할 방법 |
| US20160207893A1 (en) * | 2014-12-30 | 2016-07-21 | Myotherix, Inc. | Novel calcium modulators |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1587128A (en) * | 1977-04-07 | 1981-04-01 | Hexachimie | Benzothiazepine derivatives |
| US4285955A (en) * | 1978-10-31 | 1981-08-25 | Bayer Aktiengesellschaft | 1,4-Dihydropyridinecarboxylic acids |
| NZ201395A (en) * | 1981-07-30 | 1987-02-20 | Bayer Ag | Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines |
| FR2511683A1 (fr) * | 1981-08-20 | 1983-02-25 | Hexachimie | Nouveaux derives de la pyrido (2,3-b) benzothiazepine(1,5) substituee en 5 par une carboxypiperazine, leur procede de preparation, leur application en therapeutique |
| EP0225175A3 (en) * | 1985-11-28 | 1988-12-28 | FISONS plc | Dihydropyridine derivatives, processes for their preparation and pharmaceutical compositions thereof |
-
1990
- 1990-05-03 US US07/518,351 patent/US5075440A/en not_active Expired - Lifetime
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1991
- 1991-04-29 IL IL12044797A patent/IL120447A/xx not_active IP Right Cessation
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- 1991-04-29 IL IL12044697A patent/IL120446A0/xx unknown
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- 1991-04-29 IL IL12704798A patent/IL127047A0/xx unknown
- 1991-04-29 IL IL97999A patent/IL97999A/xx not_active IP Right Cessation
- 1991-05-01 CA CA002041594A patent/CA2041594C/en not_active Expired - Fee Related
- 1991-05-02 HU HU476/91A patent/HU218909B/hu not_active IP Right Cessation
- 1991-05-02 ES ES91303970T patent/ES2079570T3/es not_active Expired - Lifetime
- 1991-05-02 AT AT91303970T patent/ATE126231T1/de not_active IP Right Cessation
- 1991-05-02 AU AU76354/91A patent/AU651580B2/en not_active Ceased
- 1991-05-02 JP JP13047291A patent/JP3296499B2/ja not_active Expired - Fee Related
- 1991-05-02 DK DK91303970.7T patent/DK0462696T3/da active
- 1991-05-02 ZW ZW52/91A patent/ZW5291A1/xx unknown
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- 1991-05-02 EP EP91303970A patent/EP0462696B1/en not_active Expired - Lifetime
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- 1991-05-02 KR KR1019910007086A patent/KR100195345B1/ko not_active IP Right Cessation
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- 1991-05-03 TN TNTNSN91030A patent/TNSN91030A1/fr unknown
- 1991-07-20 TW TW080105637A patent/TW218878B/zh active
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