DE69111915T2 - Pyrido(2,3-f)(1,4)thiazepine und Pyrido(3,2-b)(1,5)benzothiazepine. - Google Patents
Pyrido(2,3-f)(1,4)thiazepine und Pyrido(3,2-b)(1,5)benzothiazepine.Info
- Publication number
- DE69111915T2 DE69111915T2 DE69111915T DE69111915T DE69111915T2 DE 69111915 T2 DE69111915 T2 DE 69111915T2 DE 69111915 T DE69111915 T DE 69111915T DE 69111915 T DE69111915 T DE 69111915T DE 69111915 T2 DE69111915 T2 DE 69111915T2
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- ethyl
- dioxo
- carboxylate
- thiazepine
- Prior art date
- 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.)
- Expired - Fee Related
Links
- 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 abstract description 7
- JROBKLYZJGATCR-UHFFFAOYSA-N pyrido[2,3-f][1,4]thiazepine Chemical compound S1C=CN=CC2=NC=CC=C12 JROBKLYZJGATCR-UHFFFAOYSA-N 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 7
- -1 3-piperidyl Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 239000003810 Jones reagent Substances 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 150000002924 oxiranes Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- IEJDMGCOZLTFCF-UHFFFAOYSA-N ethyl 9-(2,3-dichlorophenyl)-7-methyl-1,1-dioxo-2,3,4,5,6,9-hexahydropyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(CNCCS2(=O)=O)=C2C1C1=CC=CC(Cl)=C1Cl IEJDMGCOZLTFCF-UHFFFAOYSA-N 0.000 claims description 5
- FHGWEHGZBUBQKL-UHFFFAOYSA-N 1,2-benzothiazepine Chemical compound S1N=CC=CC2=CC=CC=C12 FHGWEHGZBUBQKL-UHFFFAOYSA-N 0.000 claims description 4
- YTLYLLTVENPWFT-UHFFFAOYSA-N 3-aminoprop-2-enoic acid Chemical class NC=CC(O)=O YTLYLLTVENPWFT-UHFFFAOYSA-N 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- HBTMWZADMHBLMY-UHFFFAOYSA-N tert-butyl n-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyldisulfanyl]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCSSCCNC(=O)OC(C)(C)C HBTMWZADMHBLMY-UHFFFAOYSA-N 0.000 claims description 4
- UBHDBZKDPMMXQE-UHFFFAOYSA-N 1,1-dioxothiazepin-3-one Chemical compound O=C1NS(=O)(=O)C=CC=C1 UBHDBZKDPMMXQE-UHFFFAOYSA-N 0.000 claims description 3
- CAPDYFKOBNQPLY-UHFFFAOYSA-N 2-acetyloxyethyl 9-(2,3-dichlorophenyl)-4,7-dimethyl-1,1-dioxo-3,5,6,9-tetrahydro-2h-pyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound C1N(C)CCS(=O)(=O)C2=C1NC(C)=C(C(=O)OCCOC(C)=O)C2C1=CC=CC(Cl)=C1Cl CAPDYFKOBNQPLY-UHFFFAOYSA-N 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
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- 206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 3
- 208000005872 Diffuse Esophageal Spasm Diseases 0.000 claims description 3
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 3
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 208000017228 Gastrointestinal motility disease Diseases 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 3
- 206010036600 Premature labour Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 208000026723 Urinary tract disease Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
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- 208000006673 asthma Diseases 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 201000011304 dilated cardiomyopathy 1A Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 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 description 3
- 230000009610 hypersensitivity Effects 0.000 claims description 3
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- 238000007363 ring formation reaction Methods 0.000 claims description 3
- GSJJCZSHYJNRPN-UHFFFAOYSA-N tert-butyl n-(2-sulfanylethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCS GSJJCZSHYJNRPN-UHFFFAOYSA-N 0.000 claims description 3
- 208000014001 urinary system disease Diseases 0.000 claims description 3
- MYQFCTDWPOWZFU-UHFFFAOYSA-N 2-(2,2-dimethylpropanoyloxy)ethyl 9-(2,3-dichlorophenyl)-4,7-dimethyl-1,1-dioxo-3,5,6,9-tetrahydro-2h-pyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound C1N(C)CCS(=O)(=O)C2=C1NC(C)=C(C(=O)OCCOC(=O)C(C)(C)C)C2C1=CC=CC(Cl)=C1Cl MYQFCTDWPOWZFU-UHFFFAOYSA-N 0.000 claims description 2
- OROVIEKAJZRVDU-UHFFFAOYSA-N 2-[benzyl(methyl)amino]ethyl 9-(2,3-dichlorophenyl)-4,7-dimethyl-1,1-dioxo-3,5,6,9-tetrahydro-2h-pyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound C=1C=CC=CC=1CN(C)CCOC(=O)C1=C(C)NC(CN(C)CCS2(=O)=O)=C2C1C1=CC=CC(Cl)=C1Cl OROVIEKAJZRVDU-UHFFFAOYSA-N 0.000 claims description 2
- VNNWSAVNKAVQCI-UHFFFAOYSA-N 2-[benzyl(methyl)amino]ethyl 9-(2,3-dichlorophenyl)-7-methyl-1,1-dioxo-2,3,4,5,6,9-hexahydropyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound C=1C=CC=CC=1CN(C)CCOC(=O)C1=C(C)NC(CNCCS2(=O)=O)=C2C1C1=CC=CC(Cl)=C1Cl VNNWSAVNKAVQCI-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
- ABDBTUQWVQRHIR-UHFFFAOYSA-N ethyl 4,7-dimethyl-1,1-dioxo-9-(2,3,4,5,6-pentafluorophenyl)-3,5,6,9-tetrahydro-2h-pyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(CN(C)CCS2(=O)=O)=C2C1C1=C(F)C(F)=C(F)C(F)=C1F ABDBTUQWVQRHIR-UHFFFAOYSA-N 0.000 claims description 2
- GRVYJCQXTOVYKE-UHFFFAOYSA-N ethyl 4-ethyl-7-methyl-9-(3-nitrophenyl)-1,1-dioxo-3,5,6,9-tetrahydro-2h-pyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(CN(CC)CCS2(=O)=O)=C2C1C1=CC=CC([N+]([O-])=O)=C1 GRVYJCQXTOVYKE-UHFFFAOYSA-N 0.000 claims description 2
- SSKRHFOGPDYPTA-UHFFFAOYSA-N ethyl 7-methyl-1,1-dioxo-9-(2,3,4,5,6-pentafluorophenyl)-2,3,4,5,6,9-hexahydropyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(CNCCS2(=O)=O)=C2C1C1=C(F)C(F)=C(F)C(F)=C1F SSKRHFOGPDYPTA-UHFFFAOYSA-N 0.000 claims description 2
- SUTNFVSFZNSBOP-UHFFFAOYSA-N ethyl 9-(2,3-dichlorophenyl)-4,7-dimethyl-1,1-dioxo-3,5,6,9-tetrahydro-2h-pyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(CN(C)CCS2(=O)=O)=C2C1C1=CC=CC(Cl)=C1Cl SUTNFVSFZNSBOP-UHFFFAOYSA-N 0.000 claims description 2
- HWBOBZWERQESJP-UHFFFAOYSA-N ethyl 9-(2,3-dichlorophenyl)-4-ethyl-7-methyl-1,1-dioxo-3,5,6,9-tetrahydro-2h-pyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(CN(CC)CCS2(=O)=O)=C2C1C1=CC=CC(Cl)=C1Cl HWBOBZWERQESJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- NGDIAZZSCVVCEW-UHFFFAOYSA-M sodium;butyl sulfate Chemical compound [Na+].CCCCOS([O-])(=O)=O NGDIAZZSCVVCEW-UHFFFAOYSA-M 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 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 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- NGBHIADNEOTIAL-UHFFFAOYSA-N 1$l^{6},2-benzothiazepine 1,1-dioxide Chemical compound O=S1(=O)N=CC=CC2=CC=CC=C12 NGBHIADNEOTIAL-UHFFFAOYSA-N 0.000 claims 2
- RGBBOEBMADDVIZ-UHFFFAOYSA-N 2-[benzyl(methyl)amino]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 C=1C=CC=CC=1CN(C)CCOC(=O)C1=C(C)NC(CN(C)C2=CC=CC=C2S2(=O)=O)=C2C1C1=CC=CC(Cl)=C1Cl RGBBOEBMADDVIZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005333 aroyloxy group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
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- 239000002904 solvent Substances 0.000 description 10
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
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- 125000000217 alkyl group Chemical group 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- FYXKGVNJWWKCLE-UHFFFAOYSA-N 2-acetyloxyethyl 9-(2,3-dichlorophenyl)-7-methyl-1,1-dioxo-2,3,4,5,6,9-hexahydropyrido[2,3-f][1,4]thiazepine-8-carboxylate Chemical compound CC(=O)OCCOC(=O)C1=C(C)NC(CNCCS2(=O)=O)=C2C1C1=CC=CC(Cl)=C1Cl FYXKGVNJWWKCLE-UHFFFAOYSA-N 0.000 description 2
- KQXOTFWSCQLHPY-UHFFFAOYSA-N 3-hydroxy-3,4-dihydro-2h-1,5-benzothiazepine-5-carbaldehyde Chemical compound O=CN1CC(O)CSC2=CC=CC=C21 KQXOTFWSCQLHPY-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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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Landscapes
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- 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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Luminescent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69111915D1 DE69111915D1 (de) | 1995-09-14 |
| DE69111915T2 true DE69111915T2 (de) | 1996-01-04 |
Family
ID=24063558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69111915T Expired - Fee Related DE69111915T2 (de) | 1990-05-03 | 1991-05-02 | Pyrido(2,3-f)(1,4)thiazepine und Pyrido(3,2-b)(1,5)benzothiazepine. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5075440A (https=) |
| EP (1) | EP0462696B1 (https=) |
| JP (1) | JP3296499B2 (https=) |
| KR (1) | KR100195345B1 (https=) |
| CN (2) | CN1034077C (https=) |
| AT (1) | ATE126231T1 (https=) |
| AU (1) | AU651580B2 (https=) |
| CA (1) | CA2041594C (https=) |
| DE (1) | DE69111915T2 (https=) |
| DK (1) | DK0462696T3 (https=) |
| ES (1) | ES2079570T3 (https=) |
| FI (1) | FI95912C (https=) |
| GR (1) | GR3017305T3 (https=) |
| HK (1) | HK51496A (https=) |
| HU (1) | HU218909B (https=) |
| IE (1) | IE68524B1 (https=) |
| IL (6) | IL127047A0 (https=) |
| MY (1) | MY106552A (https=) |
| NO (1) | NO179411C (https=) |
| NZ (1) | NZ237988A (https=) |
| PT (1) | PT97547B (https=) |
| TN (1) | TNSN91030A1 (https=) |
| TW (1) | TW218878B (https=) |
| ZA (1) | ZA913319B (https=) |
| ZW (1) | ZW5291A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU756505B2 (en) * | 1997-12-18 | 2003-01-16 | Abbott Laboratories | Potassium channel openers |
| 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 |
| HUP0201566A3 (en) * | 1999-06-14 | 2004-03-01 | Ortho Mcneil Pharm Inc | Dithiepino[6,5-b]pyridines, their preparation pharmaceutical compositions containing thereof and an apparatus for their administering |
| ES2246248T3 (es) * | 1999-07-12 | 2006-02-16 | Ortho-Mcneil Pharmaceutical, Inc. | Oxatiepino (6,5-b)dihidropiridinas, y composiciones y metodos relacionados. |
| US6472530B1 (en) | 1999-09-22 | 2002-10-29 | Ortho-Mcneil Pharmaceutical, Inc. | Benzo-fused dithiepino[6,5-b]pyridines, and related compositions and methods |
| CA2396962A1 (en) | 2000-01-12 | 2001-07-19 | Ortho-Mcneil Pharmaceutical, Inc. | Benzosulfones and related compositions and methods |
| AU783503B2 (en) * | 2000-01-27 | 2005-11-03 | 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 |
| CN1444587A (zh) | 2000-05-30 | 2003-09-24 | 奥索-麦克尼尔药品公司 | 二氢吡啶软药及相关组合物和方法 |
| 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 |
Family Cites Families (5)
| 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
-
1991
- 1991-04-29 IL IL12704798A patent/IL127047A0/xx unknown
- 1991-04-29 IL IL12044691A patent/IL120446A/xx not_active IP Right Cessation
- 1991-04-29 IL IL97999A patent/IL97999A/xx not_active IP Right Cessation
- 1991-04-29 IL IL12704791A patent/IL127047A/xx not_active IP Right Cessation
- 1991-04-29 IL IL12044697A patent/IL120446A0/xx unknown
- 1991-04-29 NZ NZ237988A patent/NZ237988A/xx unknown
- 1991-04-29 IL IL12044797A patent/IL120447A/xx not_active IP Right Cessation
- 1991-05-01 CA CA002041594A patent/CA2041594C/en not_active Expired - Fee Related
- 1991-05-02 FI FI912124A patent/FI95912C/fi active
- 1991-05-02 DE DE69111915T patent/DE69111915T2/de not_active Expired - Fee Related
- 1991-05-02 ZW ZW52/91A patent/ZW5291A1/xx unknown
- 1991-05-02 HU HU476/91A patent/HU218909B/hu not_active IP Right Cessation
- 1991-05-02 EP EP91303970A patent/EP0462696B1/en not_active Expired - Lifetime
- 1991-05-02 ES ES91303970T patent/ES2079570T3/es not_active Expired - Lifetime
- 1991-05-02 PT PT97547A patent/PT97547B/pt not_active IP Right Cessation
- 1991-05-02 DK DK91303970.7T patent/DK0462696T3/da active
- 1991-05-02 ZA ZA913319A patent/ZA913319B/xx unknown
- 1991-05-02 NO NO911723A patent/NO179411C/no unknown
- 1991-05-02 AU AU76354/91A patent/AU651580B2/en not_active Ceased
- 1991-05-02 KR KR1019910007086A patent/KR100195345B1/ko not_active Expired - Fee Related
- 1991-05-02 IE IE148891A patent/IE68524B1/en not_active IP Right Cessation
- 1991-05-02 AT AT91303970T patent/ATE126231T1/de not_active IP Right Cessation
- 1991-05-02 JP JP13047291A patent/JP3296499B2/ja not_active Expired - Fee Related
- 1991-05-02 MY MYPI91000748A patent/MY106552A/en unknown
- 1991-05-03 CN CN91103594A patent/CN1034077C/zh not_active Expired - Fee Related
- 1991-05-03 TN TNTNSN91030A patent/TNSN91030A1/fr unknown
- 1991-07-20 TW TW080105637A patent/TW218878B/zh active
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1995
- 1995-07-29 CN CN95109346A patent/CN1039416C/zh not_active Expired - Fee Related
- 1995-09-06 GR GR950402432T patent/GR3017305T3/el unknown
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1996
- 1996-03-21 HK HK51496A patent/HK51496A/en not_active IP Right Cessation
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