RU2367660C9 - Нор-секопроизводные гимбацина, обладающие ингибирующим действием в отношении рецепторов тромбина - Google Patents
Нор-секопроизводные гимбацина, обладающие ингибирующим действием в отношении рецепторов тромбинаInfo
- Publication number
- RU2367660C9 RU2367660C9 RU2006113638/04A RU2006113638A RU2367660C9 RU 2367660 C9 RU2367660 C9 RU 2367660C9 RU 2006113638/04 A RU2006113638/04 A RU 2006113638/04A RU 2006113638 A RU2006113638 A RU 2006113638A RU 2367660 C9 RU2367660 C9 RU 2367660C9
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- compound represented
- pharmaceutically acceptable
- structural formula
- solvate
- Prior art date
Links
- 102000003790 Thrombin receptors Human genes 0.000 title claims abstract description 23
- 108090000166 Thrombin receptors Proteins 0.000 title claims abstract description 23
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 15
- FMPNFDSPHNUFOS-HQEQRHKESA-N Himbacine Natural products C(/[C@@H]1[C@H]2CCCC[C@@H]2C[C@@H]2C(=O)O[C@H]([C@H]12)C)=C\[C@@H]1CCC[C@H](C)N1C FMPNFDSPHNUFOS-HQEQRHKESA-N 0.000 title 1
- FMPNFDSPHNUFOS-UHFFFAOYSA-N N-Methyl-himandravin Natural products C12C(C)OC(=O)C2CC2CCCCC2C1C=CC1CCCC(C)N1C FMPNFDSPHNUFOS-UHFFFAOYSA-N 0.000 title 1
- FMPNFDSPHNUFOS-LPJDIUFZSA-N himbacine Chemical compound C(/[C@@H]1[C@H]2CCCC[C@@H]2C[C@@H]2C(=O)O[C@H]([C@H]12)C)=C\[C@H]1CCC[C@H](C)N1C FMPNFDSPHNUFOS-LPJDIUFZSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 239000002327 cardiovascular agent Substances 0.000 claims description 13
- 229940125692 cardiovascular agent Drugs 0.000 claims description 13
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 8
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 7
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 7
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 claims description 6
- 229960003958 clopidogrel bisulfate Drugs 0.000 claims description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 6
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000007536 Thrombosis Diseases 0.000 claims description 3
- 206010043647 Thrombotic Stroke Diseases 0.000 claims description 3
- 206010003119 arrhythmia Diseases 0.000 claims description 3
- 230000006793 arrhythmia Effects 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 238000005345 coagulation Methods 0.000 claims description 3
- 230000015271 coagulation Effects 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 230000001732 thrombotic effect Effects 0.000 claims description 2
- 208000005189 Embolism Diseases 0.000 claims 1
- 230000009424 thromboembolic effect Effects 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 41
- 229910052739 hydrogen Inorganic materials 0.000 description 41
- 239000000203 mixture Substances 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 239000001257 hydrogen Substances 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 16
- -1 C 1 -C 6 alkyl Chemical group 0.000 description 15
- 229910052736 halogen Inorganic materials 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 210000004369 blood Anatomy 0.000 description 13
- 239000008280 blood Substances 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 150000002367 halogens Chemical class 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 210000001772 blood platelet Anatomy 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 239000012528 membrane Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000004220 aggregation Methods 0.000 description 9
- 230000002776 aggregation Effects 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 150000002431 hydrogen Chemical group 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 108090000765 processed proteins & peptides Proteins 0.000 description 7
- 239000003856 thrombin receptor antagonist Substances 0.000 description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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- 229910052722 tritium Inorganic materials 0.000 description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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Classifications
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Landscapes
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/671,216 US7488742B2 (en) | 2000-06-15 | 2003-09-25 | Thrombin receptor antagonists |
| US10/671,216 | 2003-09-25 |
Publications (3)
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|---|---|
| RU2006113638A RU2006113638A (ru) | 2007-11-10 |
| RU2367660C2 RU2367660C2 (ru) | 2009-09-20 |
| RU2367660C9 true RU2367660C9 (ru) | 2010-08-10 |
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| RU2006113638/04A RU2367660C9 (ru) | 2003-09-25 | 2004-09-23 | Нор-секопроизводные гимбацина, обладающие ингибирующим действием в отношении рецепторов тромбина |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US7488742B2 (https=) |
| EP (1) | EP1663965B1 (https=) |
| JP (1) | JP4694490B2 (https=) |
| KR (1) | KR20060128848A (https=) |
| CN (1) | CN101128457A (https=) |
| AR (1) | AR045809A1 (https=) |
| AU (1) | AU2004276327B2 (https=) |
| BR (1) | BRPI0414592A (https=) |
| CA (1) | CA2540163C (https=) |
| CO (1) | CO5680428A2 (https=) |
| EC (1) | ECSP066455A (https=) |
| IL (1) | IL174538A0 (https=) |
| MX (1) | MXPA06003379A (https=) |
| MY (1) | MY143834A (https=) |
| NO (1) | NO20061797L (https=) |
| PE (1) | PE20050471A1 (https=) |
| RU (1) | RU2367660C9 (https=) |
| SG (1) | SG147466A1 (https=) |
| TW (1) | TWI331608B (https=) |
| WO (1) | WO2005030712A2 (https=) |
| ZA (1) | ZA200602448B (https=) |
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| US6346510B1 (en) | 1995-10-23 | 2002-02-12 | The Children's Medical Center Corporation | Therapeutic antiangiogenic endostatin compositions |
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| BRPI0309309B8 (pt) * | 2002-04-16 | 2021-05-25 | Merck Sharp & Dohme | antagonistas de receptor de trombina tricíclicos |
| ES2427166T3 (es) * | 2003-06-23 | 2013-10-29 | Ono Pharmaceutical Co., Ltd. | Compuesto heterocíclico tricíclico novedoso |
| CN1984905B (zh) * | 2004-05-28 | 2011-06-22 | 先灵公司 | 作为凝血酶受体拮抗剂的约束喜巴辛类似物 |
| US20060063930A1 (en) * | 2004-08-20 | 2006-03-23 | Agoston Gregory E | Compositions and methods comprising proteinase activated receptor antagonists |
| US8563511B2 (en) * | 2004-10-06 | 2013-10-22 | University Of Rochester | Treatment of pulmonary hypertension using an agent that inhibits a tissue factor pathway |
| US7488752B2 (en) * | 2004-10-08 | 2009-02-10 | Schering Corporation | Thrombin receptor antagonists |
| WO2006068164A1 (ja) * | 2004-12-22 | 2006-06-29 | Ono Pharmaceutical Co., Ltd. | 三環式化合物およびその用途 |
| CA2875768C (en) | 2005-01-14 | 2018-03-06 | George G. Wu | Process for the preparation of phosphonate compounds useful in the preparation of himbacine analogs |
| US7776889B2 (en) * | 2005-03-31 | 2010-08-17 | Schering Corporation | Spirocyclic thrombin receptor antagonists |
| WO2007075808A2 (en) * | 2005-12-20 | 2007-07-05 | Schering Corporation | Methods for preventing and/or treating a cell proliferative disorder |
| JP2009521458A (ja) * | 2005-12-22 | 2009-06-04 | シェーリング コーポレイション | トロンビン受容体アンタゴニストとしてのオキサゾロイソキノリン誘導体 |
| JP2009521472A (ja) * | 2005-12-22 | 2009-06-04 | シェーリング コーポレイション | 心肺手術の合併症の予防としてのトロンビンレセプターアンタゴニスト |
| AU2007243657A1 (en) * | 2006-03-29 | 2007-11-08 | Schering Corporation | Monocyclic and bicyclic himbacine derivatives useful as thrombin receptor antagonists |
| TW200812619A (en) * | 2006-04-06 | 2008-03-16 | Schering Corp | TRA combination therapies |
| US8003803B2 (en) * | 2006-04-13 | 2011-08-23 | Schering Corporation | Fused ring thrombin receptor antagonists |
| EP2032560B1 (en) * | 2006-06-29 | 2013-05-01 | Merck Sharp & Dohme Corp. | Substituted bicyclic and tricyclic thrombin receptor antagonists |
| TWI367112B (en) * | 2006-06-30 | 2012-07-01 | Schering Corp | Immediate-release tablet formulations of a thrombin receptor antagonist |
| DE102006036023A1 (de) * | 2006-08-02 | 2008-02-07 | Sanofi-Aventis | Imino-imidazo-pyridinderivate mit antithrombotischer Aktivität |
| TWI343262B (en) * | 2006-09-26 | 2011-06-11 | Schering Corp | Rapidly disintegrating lyophilized oral formulations of a thrombin receptor antagonist |
| EP2069326B1 (en) | 2006-10-04 | 2015-03-18 | Merck Sharp & Dohme Corp. | Bicyclic and tricyclic derivatives as thrombin receptor antagonists |
| EP2120879A2 (en) * | 2006-12-22 | 2009-11-25 | Schering Corporation | Disintegration promoters in solid dose wet granulation formulations |
| BRPI0809095A2 (pt) * | 2007-03-23 | 2014-09-09 | Schering Corp | Redução de eventos adversos após intervenção percutânea através de uso de um antagonista de receptor de trombina |
| SI2242740T1 (sl) | 2008-02-05 | 2013-03-29 | Sanofi | SF5-derivati kot PAR1 inhibitorji, njihova priprava in uporaba kot zdravila |
| RS52264B (sr) | 2008-02-05 | 2012-10-31 | Sanofi | Triazolopiridazini kao inhibitori par1, njihovo dobijanje i upotreba kao lekova |
| RU2494100C2 (ru) * | 2008-02-05 | 2013-09-27 | Санофи-Авентис | Соли триазолия в качестве ингибиторов par1, их получение и применение в качестве лекарственного средства |
| EP2438060B1 (en) | 2009-06-04 | 2013-10-02 | Merck Sharp & Dohme Corp. | Active metabolite of a thrombin receptor antagonist |
| JP2012529431A (ja) | 2009-06-08 | 2012-11-22 | メルク・シャープ・アンド・ドーム・コーポレーション | トロンビン受容体アンタゴニストおよびクロピドグレルの固定用量錠剤 |
| ES2532902T3 (es) | 2010-04-16 | 2015-04-01 | Sanofi | Piridil-vinil-pirroles tricíclicos como inhibidores de PAR1 |
| WO2011128420A1 (de) | 2010-04-16 | 2011-10-20 | Sanofi | Pyridyl-vinyl-pyrazolo-chinoline als par1-inhibitoren |
| WO2013134012A1 (en) | 2012-03-06 | 2013-09-12 | Merck Sharp & Dohme Corp. | Preparation and use of bicyclic himbacine derivatives as par-receptor antagonists |
| WO2015013083A1 (en) | 2013-07-22 | 2015-01-29 | Merck Sharp & Dohme Corp. | Co-crystal of the par-1 receptor antagonist vorapaxar and aspirin |
| WO2015026685A1 (en) * | 2013-08-22 | 2015-02-26 | Merck Sharp & Dohme Corp. | 7a-heterocycle substituted- 6, 6-difluoro bicyclic himbacine derivatives |
| EP3035928B1 (en) * | 2013-08-22 | 2023-10-18 | Merck Sharp & Dohme LLC | 3'-pyridyl substituted- 6,6-difluoro bicyclic himbacine derivatives |
| EP3035929B1 (en) * | 2013-08-22 | 2024-07-03 | Merck Sharp & Dohme LLC | 7a-amide substituted-6,6-difluoro bicyclic himbacine derivatives |
| WO2016114386A1 (ja) * | 2015-01-15 | 2016-07-21 | 国立研究開発法人国立精神・神経医療研究センター | 進行型免疫性脱髄疾患治療剤 |
| CN110407819B (zh) * | 2019-08-02 | 2020-06-26 | 牡丹江医学院 | 一种作为预防外科手术并发症的凝血酶受体拮抗剂 |
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| WO2001096330A2 (en) * | 2000-06-15 | 2001-12-20 | Schering Corporation | Thrombin receptor antagonists |
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| JP2000229961A (ja) * | 1998-12-11 | 2000-08-22 | Sagami Chem Res Center | ヒドロナフト［２，３−ｃ］フラン誘導体およびその製造方法 |
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| US7235567B2 (en) * | 2000-06-15 | 2007-06-26 | Schering Corporation | Crystalline polymorph of a bisulfate salt of a thrombin receptor antagonist |
| KR100960170B1 (ko) * | 2001-10-18 | 2010-05-26 | 쉐링 코포레이션 | 트롬빈 수용체 길항제로서의 힘바신 동족체 |
| BRPI0309309B8 (pt) * | 2002-04-16 | 2021-05-25 | Merck Sharp & Dohme | antagonistas de receptor de trombina tricíclicos |
| CN1984905B (zh) * | 2004-05-28 | 2011-06-22 | 先灵公司 | 作为凝血酶受体拮抗剂的约束喜巴辛类似物 |
| JP2008526254A (ja) * | 2005-01-14 | 2008-07-24 | シェーリング コーポレイション | ヒンバシン類似物のキラルプロパルギルアルコールおよびエステル中間体の調製 |
| CA2875768C (en) * | 2005-01-14 | 2018-03-06 | George G. Wu | Process for the preparation of phosphonate compounds useful in the preparation of himbacine analogs |
| US7541471B2 (en) * | 2005-01-14 | 2009-06-02 | Schering Corporation | Synthesis of himbacine analogs |
| WO2006076452A2 (en) * | 2005-01-14 | 2006-07-20 | Schering Corporation | An exo-selective synthesis of himbacine analogs |
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2003
- 2003-09-25 US US10/671,216 patent/US7488742B2/en not_active Expired - Lifetime
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2004
- 2004-09-23 CN CNA2004800278261A patent/CN101128457A/zh active Pending
- 2004-09-23 SG SG200807889-1A patent/SG147466A1/en unknown
- 2004-09-23 AU AU2004276327A patent/AU2004276327B2/en not_active Ceased
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- 2004-09-23 RU RU2006113638/04A patent/RU2367660C9/ru not_active IP Right Cessation
- 2004-09-23 WO PCT/US2004/031495 patent/WO2005030712A2/en not_active Ceased
- 2004-09-23 CA CA2540163A patent/CA2540163C/en not_active Expired - Fee Related
- 2004-09-23 EP EP04789042.1A patent/EP1663965B1/en not_active Expired - Lifetime
- 2004-09-23 PE PE2004000927A patent/PE20050471A1/es not_active Application Discontinuation
- 2004-09-23 JP JP2006528258A patent/JP4694490B2/ja not_active Expired - Fee Related
- 2004-09-23 KR KR1020067005753A patent/KR20060128848A/ko not_active Ceased
- 2004-09-23 BR BRPI0414592-5A patent/BRPI0414592A/pt not_active IP Right Cessation
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| US6063847A (en) * | 1997-11-25 | 2000-05-16 | Schering Corporation | Thrombin receptor antagonists |
| RU2204557C2 (ru) * | 1997-11-25 | 2003-05-20 | Шеринг Корпорейшн | Замещенные бициклические соединения, фармкомпозиция на их основе и способ ингибирования |
| WO2001096330A2 (en) * | 2000-06-15 | 2001-12-20 | Schering Corporation | Thrombin receptor antagonists |
Also Published As
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| ECSP066455A (es) | 2006-09-18 |
| US20090069383A1 (en) | 2009-03-12 |
| CN101128457A (zh) | 2008-02-20 |
| EP1663965B1 (en) | 2014-04-09 |
| US20040152736A1 (en) | 2004-08-05 |
| MY143834A (en) | 2011-07-15 |
| WO2005030712A8 (en) | 2007-12-21 |
| CA2540163C (en) | 2012-06-05 |
| CO5680428A2 (es) | 2006-09-29 |
| WO2005030712A2 (en) | 2005-04-07 |
| ZA200602448B (en) | 2007-09-26 |
| AU2004276327B2 (en) | 2010-10-07 |
| CA2540163A1 (en) | 2005-04-07 |
| JP2007523051A (ja) | 2007-08-16 |
| JP4694490B2 (ja) | 2011-06-08 |
| TW200524914A (en) | 2005-08-01 |
| TWI331608B (en) | 2010-10-11 |
| MXPA06003379A (es) | 2006-06-08 |
| IL174538A0 (en) | 2006-08-01 |
| RU2367660C2 (ru) | 2009-09-20 |
| US20090076088A1 (en) | 2009-03-19 |
| BRPI0414592A (pt) | 2006-11-07 |
| US7488742B2 (en) | 2009-02-10 |
| KR20060128848A (ko) | 2006-12-14 |
| NO20061797L (no) | 2006-05-19 |
| SG147466A1 (en) | 2008-11-28 |
| EP1663965A2 (en) | 2006-06-07 |
| AU2004276327A1 (en) | 2005-04-07 |
| WO2005030712A3 (en) | 2007-09-20 |
| RU2006113638A (ru) | 2007-11-10 |
| PE20050471A1 (es) | 2005-08-24 |
| AR045809A1 (es) | 2005-11-16 |
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