SK17797A3 - 1,4-benzothiazepine-1,1-dioxides, process for producing them and a pharmaceutical composition containing them - Google Patents
1,4-benzothiazepine-1,1-dioxides, process for producing them and a pharmaceutical composition containing them Download PDFInfo
- Publication number
- SK17797A3 SK17797A3 SK177-97A SK17797A SK17797A3 SK 17797 A3 SK17797 A3 SK 17797A3 SK 17797 A SK17797 A SK 17797A SK 17797 A3 SK17797 A3 SK 17797A3
- Authority
- SK
- Slovakia
- Prior art keywords
- phenyl
- tetrahydro
- dioxide
- ethyl
- butyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 17
- IVGHNDNOFMTFMK-UHFFFAOYSA-N 1$l^{6},4-benzothiazepine 1,1-dioxide Chemical class O=S1(=O)C=CN=CC2=CC=CC=C12 IVGHNDNOFMTFMK-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 282
- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 239000012453 solvate Substances 0.000 claims abstract description 33
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 36
- -1 Butyl-3-ethyl-2,3,4,5-tetrahydro-7,8-dimethoxy-5-phenyl-1,4-benzothiazepine-1,1-dioxide Chemical compound 0.000 claims description 32
- 239000003613 bile acid Substances 0.000 claims description 25
- 238000010521 absorption reaction Methods 0.000 claims description 22
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 241000124008 Mammalia Species 0.000 claims description 15
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 230000003516 hyperlipidaemic effect Effects 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- CKFWDLFFXXVSBJ-DHIUTWEWSA-N (3r,5r)-3-butyl-3-ethyl-7,8-dimethoxy-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound C1([C@@H]2C3=CC(OC)=C(OC)C=C3S(=O)(=O)C[C@@](N2)(CC)CCCC)=CC=CC=C1 CKFWDLFFXXVSBJ-DHIUTWEWSA-N 0.000 claims description 4
- DLWMHLNMYDSEEI-FGZHOGPDSA-N (3r,5r)-7-bromo-3-butyl-3-ethyl-8-methoxy-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound C1([C@@H]2C3=CC(Br)=C(OC)C=C3S(=O)(=O)C[C@@](N2)(CC)CCCC)=CC=CC=C1 DLWMHLNMYDSEEI-FGZHOGPDSA-N 0.000 claims description 4
- QXPKFGLANUUQLO-UHFFFAOYSA-N (3,3-diethyl-1,1-dioxo-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepin-8-yl) dihydrogen phosphate Chemical compound N1C(CC)(CC)CS(=O)(=O)C2=CC(OP(O)(O)=O)=CC=C2C1C1=CC=CC=C1 QXPKFGLANUUQLO-UHFFFAOYSA-N 0.000 claims description 3
- FNVGDCHCNYDTNB-NHCUHLMSSA-N (3r,5r)-3-butyl-3-ethyl-4-hydroxy-1,1-dioxo-5-phenyl-2,5-dihydro-1$l^{6},4-benzothiazepine-7,8-diol Chemical compound C1([C@@H]2C3=CC(O)=C(O)C=C3S(=O)(=O)C[C@@](N2O)(CC)CCCC)=CC=CC=C1 FNVGDCHCNYDTNB-NHCUHLMSSA-N 0.000 claims description 3
- LMKTUSIIFPZDCU-DHIUTWEWSA-N (3r,5r)-3-butyl-3-ethyl-4-hydroxy-7,8-dimethoxy-5-phenyl-2,5-dihydro-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound C1([C@@H]2C3=CC(OC)=C(OC)C=C3S(=O)(=O)C[C@@](N2O)(CC)CCCC)=CC=CC=C1 LMKTUSIIFPZDCU-DHIUTWEWSA-N 0.000 claims description 3
- DUHUAWCEKDGUCV-FGZHOGPDSA-N (3r,5r)-7-bromo-3-butyl-3-ethyl-4-hydroxy-8-methoxy-5-phenyl-2,5-dihydro-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound C1([C@@H]2C3=CC(Br)=C(OC)C=C3S(=O)(=O)C[C@@](N2O)(CC)CCCC)=CC=CC=C1 DUHUAWCEKDGUCV-FGZHOGPDSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- VTSIDFMNNRNGHI-UHFFFAOYSA-N 3,3-dibutyl-1,1-dioxo-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepin-8-ol Chemical compound N1C(CCCC)(CCCC)CS(=O)(=O)C2=CC(O)=CC=C2C1C1=CC=CC=C1 VTSIDFMNNRNGHI-UHFFFAOYSA-N 0.000 claims description 3
- ZVLFOXFUZWSCJL-UHFFFAOYSA-N 3,3-diethyl-1,1-dioxo-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepin-8-ol Chemical compound N1C(CC)(CC)CS(=O)(=O)C2=CC(O)=CC=C2C1C1=CC=CC=C1 ZVLFOXFUZWSCJL-UHFFFAOYSA-N 0.000 claims description 3
- CDNXXKLVSPQNFM-UHFFFAOYSA-N 3,3-diethyl-4-hydroxy-1,1-dioxo-5-phenyl-2,5-dihydro-1$l^{6},4-benzothiazepin-8-ol Chemical compound ON1C(CC)(CC)CS(=O)(=O)C2=CC(O)=CC=C2C1C1=CC=CC=C1 CDNXXKLVSPQNFM-UHFFFAOYSA-N 0.000 claims description 3
- FECWNGBZGPDRRY-UHFFFAOYSA-N 3,3-diethyl-5-(4-fluorophenyl)-8-methoxy-4,5-dihydro-2h-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound N1C(CC)(CC)CS(=O)(=O)C2=CC(OC)=CC=C2C1C1=CC=C(F)C=C1 FECWNGBZGPDRRY-UHFFFAOYSA-N 0.000 claims description 3
- XIAFGTCPGRIBAS-UHFFFAOYSA-N 3,3-diethyl-7,8-dimethoxy-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound N1C(CC)(CC)CS(=O)(=O)C2=CC(OC)=C(OC)C=C2C1C1=CC=CC=C1 XIAFGTCPGRIBAS-UHFFFAOYSA-N 0.000 claims description 3
- PZFKJLXCTGHOKS-UHFFFAOYSA-N 3,3-diethyl-7-methoxy-1,1-dioxo-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepin-8-ol Chemical compound N1C(CC)(CC)CS(=O)(=O)C2=CC(O)=C(OC)C=C2C1C1=CC=CC=C1 PZFKJLXCTGHOKS-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 3
- WSWDOSVELJLVRB-FGZHOGPDSA-N (3r,5r)-3-butyl-3-ethyl-8-methoxy-7-nitro-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound C1([C@@H]2C3=CC(=C(OC)C=C3S(=O)(=O)C[C@@](N2)(CC)CCCC)[N+]([O-])=O)=CC=CC=C1 WSWDOSVELJLVRB-FGZHOGPDSA-N 0.000 claims description 2
- BYXNIXWNXSNWOH-WZONZLPQSA-N (3r,5r)-3-butyl-7,8-diethoxy-5-phenyl-2,3,4,5-tetrahydro-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound C1([C@@H]2C3=CC(OCC)=C(OCC)C=C3S(=O)(=O)C[C@H](N2)CCCC)=CC=CC=C1 BYXNIXWNXSNWOH-WZONZLPQSA-N 0.000 claims description 2
- YSHSQEIATZDZBK-DHIUTWEWSA-N C(CCC)[C@@]1(CS(C2=C([C@H](N1O)C1=CC=C(C=C1)F)C=C(C(=C2)OC)OC)(=O)=O)CC Chemical compound C(CCC)[C@@]1(CS(C2=C([C@H](N1O)C1=CC=C(C=C1)F)C=C(C(=C2)OC)OC)(=O)=O)CC YSHSQEIATZDZBK-DHIUTWEWSA-N 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
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- 229940009098 aspartate Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- KYJKQZKYGGFLOQ-FGZHOGPDSA-N (7r,9r)-7-butyl-7-ethyl-9-phenyl-8,9-dihydro-6h-[1,3]dioxolo[4,5-h][1,4]benzothiazepine 5,5-dioxide Chemical compound C1([C@@H]2C3=CC=4OCOC=4C=C3S(=O)(=O)C[C@@](N2)(CC)CCCC)=CC=CC=C1 KYJKQZKYGGFLOQ-FGZHOGPDSA-N 0.000 claims 1
- XHXALHGRTHMLDD-UHFFFAOYSA-N 2-(methoxymethyl)-5-phenyl-1lambda6,4-benzothiazepine 1,1-dioxide Chemical compound COCC=1S(C2=C(C(=NC=1)C1=CC=CC=C1)C=CC=C2)(=O)=O XHXALHGRTHMLDD-UHFFFAOYSA-N 0.000 claims 1
- WQBUUPRBDYFTDO-UHFFFAOYSA-N 2-phenyl-1lambda6,4-benzothiazepine 1,1-dioxide Chemical compound O=S1(=O)c2ccccc2C=NC=C1c1ccccc1 WQBUUPRBDYFTDO-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 27
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Classifications
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- C—CHEMISTRY; METALLURGY
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- 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
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- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28852794A | 1994-08-10 | 1994-08-10 | |
| PCT/GB1995/001884 WO1996005188A1 (en) | 1994-08-10 | 1995-08-09 | Hypolipidemic 1,4-benzothiazepine-1,1-dioxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK17797A3 true SK17797A3 (en) | 1997-09-10 |
Family
ID=23107516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK177-97A SK17797A3 (en) | 1994-08-10 | 1995-08-09 | 1,4-benzothiazepine-1,1-dioxides, process for producing them and a pharmaceutical composition containing them |
Country Status (31)
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|---|---|
| US (1) | US5910494A (bg) |
| EP (2) | EP1203769A1 (bg) |
| JP (1) | JP2935756B2 (bg) |
| KR (1) | KR100354288B1 (bg) |
| CN (1) | CN1059673C (bg) |
| AP (1) | AP720A (bg) |
| AT (1) | ATE226946T1 (bg) |
| AU (1) | AU696073B2 (bg) |
| BG (1) | BG62048B1 (bg) |
| BR (1) | BR9508586A (bg) |
| CA (1) | CA2197099A1 (bg) |
| CZ (1) | CZ37397A3 (bg) |
| DE (1) | DE69528704T2 (bg) |
| DK (1) | DK0775126T3 (bg) |
| EE (1) | EE9700028A (bg) |
| ES (1) | ES2185711T3 (bg) |
| FI (1) | FI970531A0 (bg) |
| HK (1) | HK1003936A1 (bg) |
| HU (1) | HUT77129A (bg) |
| IL (1) | IL114877A (bg) |
| IS (1) | IS4418A (bg) |
| MX (1) | MX9700890A (bg) |
| NO (1) | NO308131B1 (bg) |
| NZ (1) | NZ290911A (bg) |
| OA (1) | OA10597A (bg) |
| PL (1) | PL184512B1 (bg) |
| PT (1) | PT775126E (bg) |
| RU (1) | RU2156245C2 (bg) |
| SK (1) | SK17797A3 (bg) |
| WO (1) | WO1996005188A1 (bg) |
| ZA (1) | ZA956647B (bg) |
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| US6268392B1 (en) | 1994-09-13 | 2001-07-31 | G. D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors |
| US5994391A (en) * | 1994-09-13 | 1999-11-30 | G.D. Searle And Company | Benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| US6107494A (en) * | 1994-09-13 | 2000-08-22 | G.D. Searle And Company | Substituted 5-aryl-benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| GB9423172D0 (en) * | 1994-11-17 | 1995-01-04 | Wellcom Foundation The Limited | Hypolipidemic benzothiazepines |
| GB9704208D0 (en) * | 1997-02-28 | 1997-04-16 | Glaxo Group Ltd | Chemical compounds |
| DK0864582T3 (da) * | 1997-03-14 | 2003-09-29 | Aventis Pharma Gmbh | Hypolidemiske 1,4-benzothiazepin-1,1-dioxider |
| GB9800428D0 (en) | 1998-01-10 | 1998-03-04 | Glaxo Group Ltd | Chemical compounds |
| EA004877B1 (ru) | 1998-12-23 | 2004-08-26 | Джи.Ди.Сирл Ллс | Сочетания ингибиторов транспорта желчных кислот в подвздошной кишке и агентов, секвестрирующих желчные кислоты, для сердечно-сосудистых показаний |
| CZ20012342A3 (cs) | 1998-12-23 | 2001-12-12 | G. D. Searle Llc | Kombinace inhibitorů transportu ľlučové kyseliny v ileu a derivátů kyseliny fibrové pro kardiovaskulární indikace |
| JP2002533409A (ja) | 1998-12-23 | 2002-10-08 | ジー．ディー．サール エルエルシー | 心臓血管に適用するためのコレステリルエステル転送タンパク質阻害剤および胆汁酸隔離剤の組み合わせ |
| HUP0201972A3 (en) | 1998-12-23 | 2005-06-28 | G D Searle Llc Chicago | Combinations of ileal bile acid transport inhibitors and cholesteryl ester transfer protein inhibitors for cardiovascular indications |
| EA009466B1 (ru) | 1998-12-23 | 2007-12-28 | Джи.Ди. Сирл Ллс | Ингибитор белка, переносящего эфир холестерила |
| AU2157400A (en) | 1998-12-23 | 2000-07-31 | G.D. Searle & Co. | Combinations of cholesteryl ester transfer protein inhibitors and hmg coa reductase inhibitors for cardiovascular indications |
| US6489366B1 (en) | 1998-12-23 | 2002-12-03 | G. D. Searle, Llc | Combinations of cholesteryl ester transfer protein inhibitors and nicotinic acid derivatives for cardiovascular indications |
| KR20020000139A (ko) * | 1999-02-12 | 2002-01-04 | 추후제출 | 회장 담즙산 수송 및 타우로콜산염 흡수의 억제제로서의활성을 보유하는 신규한 1,2-벤조티아제핀 |
| DE19916108C1 (de) * | 1999-04-09 | 2001-01-11 | Aventis Pharma Gmbh | Mit Zuckerresten substituierte 1,4-Benzothiazepin-1,1-dioxidderivate, Verfahren zu deren Herstellung und deren Verwendung |
| GB9914745D0 (en) * | 1999-06-24 | 1999-08-25 | Knoll Ag | Therapeutic agents |
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| GB0209467D0 (en) | 2002-04-25 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
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| US7544678B2 (en) | 2002-11-05 | 2009-06-09 | The Trustees Of Columbia University In The City Of New York | Anti-arrythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2) |
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| KR20230106651A (ko) | 2020-11-12 | 2023-07-13 | 알비레오 에이비 | 진행성 가족성 간내 담즙정체증(pfic)을 치료하기 위한 오데빅시바트 |
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| GB9203347D0 (en) * | 1992-02-17 | 1992-04-01 | Wellcome Found | Hypolipidaemic compounds |
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| IL108634A0 (en) * | 1993-02-15 | 1994-05-30 | Wellcome Found | Hypolipidaemic heterocyclic compounds, their prepatation and pharmaceutical compositions containing them |
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1995
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- 1995-08-09 WO PCT/GB1995/001884 patent/WO1996005188A1/en active IP Right Grant
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- 1995-08-09 AU AU44260/96A patent/AU696073B2/en not_active Ceased
- 1995-08-09 AT AT95927877T patent/ATE226946T1/de not_active IP Right Cessation
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- 1995-08-09 EP EP02003711A patent/EP1203769A1/en not_active Withdrawn
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- 1995-08-09 KR KR1019970700845A patent/KR100354288B1/ko not_active IP Right Cessation
- 1995-08-09 DK DK95927877T patent/DK0775126T3/da active
- 1995-08-09 CZ CZ97373A patent/CZ37397A3/cs unknown
- 1995-08-09 PL PL95318496A patent/PL184512B1/pl unknown
- 1995-08-09 BR BR9508586A patent/BR9508586A/pt not_active Application Discontinuation
- 1995-08-09 CA CA002197099A patent/CA2197099A1/en not_active Abandoned
- 1995-08-09 RU RU97104002/04A patent/RU2156245C2/ru active
- 1995-08-09 CN CN95195419A patent/CN1059673C/zh not_active Expired - Fee Related
- 1995-08-09 PT PT95927877T patent/PT775126E/pt unknown
- 1995-08-09 HU HU9700408A patent/HUT77129A/hu active IP Right Revival
- 1995-08-09 DE DE69528704T patent/DE69528704T2/de not_active Expired - Fee Related
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1997
- 1997-01-24 IS IS4418A patent/IS4418A/is unknown
- 1997-02-06 OA OA60961A patent/OA10597A/en unknown
- 1997-02-07 NO NO970585A patent/NO308131B1/no not_active IP Right Cessation
- 1997-02-07 BG BG101209A patent/BG62048B1/bg unknown
- 1997-02-07 FI FI970531A patent/FI970531A0/fi unknown
-
1998
- 1998-04-15 HK HK98103105A patent/HK1003936A1/xx not_active IP Right Cessation
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