JP2008524335A - イミダゾ［４，５−ｃ］ピリジン化合物および抗ウイルス処置法 - Google Patents
イミダゾ［４，５−ｃ］ピリジン化合物および抗ウイルス処置法 Download PDFInfo
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- JP2008524335A JP2008524335A JP2007548448A JP2007548448A JP2008524335A JP 2008524335 A JP2008524335 A JP 2008524335A JP 2007548448 A JP2007548448 A JP 2007548448A JP 2007548448 A JP2007548448 A JP 2007548448A JP 2008524335 A JP2008524335 A JP 2008524335A
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229950008679 protamine sulfate Drugs 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 208000000995 spontaneous abortion Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US63821504P | 2004-12-21 | 2004-12-21 | |
| PCT/US2005/046477 WO2006069193A2 (en) | 2004-12-21 | 2005-12-21 | Imidazo[4,5-c]pyridine compound and method of antiviral treatment |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2012148683A Division JP2012184265A (ja) | 2004-12-21 | 2012-07-02 | イミダゾ［４，５−ｃ］ピリジン化合物および抗ウイルス処置法 |
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| JP2008524335A true JP2008524335A (ja) | 2008-07-10 |
| JP2008524335A5 JP2008524335A5 (enExample) | 2009-02-19 |
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| JP2012148683A Pending JP2012184265A (ja) | 2004-12-21 | 2012-07-02 | イミダゾ［４，５−ｃ］ピリジン化合物および抗ウイルス処置法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2012148683A Pending JP2012184265A (ja) | 2004-12-21 | 2012-07-02 | イミダゾ［４，５−ｃ］ピリジン化合物および抗ウイルス処置法 |
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| Country | Link |
|---|---|
| US (2) | US20060252791A1 (enExample) |
| EP (1) | EP1841765B1 (enExample) |
| JP (2) | JP2008524335A (enExample) |
| AT (1) | ATE426601T1 (enExample) |
| AU (1) | AU2005319167B2 (enExample) |
| CA (1) | CA2592388C (enExample) |
| CY (1) | CY1109087T1 (enExample) |
| DE (1) | DE602005013580D1 (enExample) |
| DK (1) | DK1841765T5 (enExample) |
| ES (1) | ES2324794T3 (enExample) |
| NZ (1) | NZ556624A (enExample) |
| PL (1) | PL1841765T3 (enExample) |
| PT (1) | PT1841765E (enExample) |
| SI (1) | SI1841765T1 (enExample) |
| WO (1) | WO2006069193A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0215293D0 (en) * | 2002-07-03 | 2002-08-14 | Rega Foundation | Viral inhibitors |
| NZ595000A (en) * | 2003-12-22 | 2013-03-28 | Gilead Sciences Inc | Imidazo[4,5-c]pyridine derivative for treating viral infections |
| KR101143596B1 (ko) * | 2006-07-07 | 2012-05-11 | 길리애드 사이언시즈, 인코포레이티드 | 신규의 피리다진 화합물 및 이의 용도 |
| DK2094702T3 (en) * | 2006-12-14 | 2015-12-07 | Gilead Sciences Inc | viral inhibitors |
| UA99466C2 (en) * | 2007-07-06 | 2012-08-27 | Гилиад Сайенсиз, Инк. | Crystalline pyridazine compound |
| US20110044943A1 (en) * | 2007-07-13 | 2011-02-24 | Martin Robert Leivers | Anti-Viral Compounds, Compositions, And Methods Of Use |
| WO2011146817A1 (en) | 2010-05-21 | 2011-11-24 | Gilead Sciences, Inc. | Heterocyclic flaviviridae virus inhibitors |
| IL296496B2 (en) | 2014-12-26 | 2024-10-01 | Univ Emory | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| RS66222B1 (sr) | 2017-12-07 | 2024-12-31 | Univ Emory | N4-hidroksicitidin i derivati i antivirusne upotrebe povezane sa njim |
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| JP2007518720A (ja) * | 2003-12-22 | 2007-07-12 | カー・イュー・ルーベン・リサーチ・アンド・ディベロップメント | イミダゾ［４，５−ｃ］ピリジン化合物および抗ウイルス治療の方法 |
Family Cites Families (87)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2191978A (en) | 1935-10-10 | 1940-02-27 | Ig Farbenindustrie Ag | Quaternary nitrogen compounds and process of preparing them |
| US2411662A (en) | 1943-05-13 | 1946-11-26 | Geigy Ag J R | Imino-di-fatty acid amide |
| US2548863A (en) | 1946-05-29 | 1951-04-17 | Wyeth Corp | Substituted glycinamides |
| US2516674A (en) | 1948-10-29 | 1950-07-25 | Wyeth Corp | Substituted glycinamide |
| US3985891A (en) * | 1973-02-03 | 1976-10-12 | Boehringer Ingelheim Gmbh | 2-Phenyl-imidazo (4,5-b)pyridines and salts thereof |
| SU813921A1 (ru) | 1979-10-26 | 1986-12-23 | Институт физико-органической химии и углехимии АН УССР | Стирильные производные имидазо(4,5- @ )пиридиний иодида,обладающие фунгицидной активностью |
| SU851940A1 (ru) | 1980-03-20 | 1988-04-30 | Институт физико-органической химии и углехимии АН УССР | Четвертичные соли имидазо @ 4,5-с @ пиридини ,обладающие антимикробной и фунгистатической активностью |
| SU1048742A1 (ru) | 1981-03-30 | 1986-12-23 | Институт физико-органической химии и углехимии АН УССР | 2,4-Дистирилпроизводные имидазо-(4,5- @ )пиридини ,обладающие бактериостатической и фунгистатической активностью |
| US4358387A (en) | 1981-08-10 | 1982-11-09 | Texaco Inc. | Cylinder lubricating oil composition |
| US5137896A (en) * | 1981-10-01 | 1992-08-11 | Janssen Pharmaceutica N.V. | N-(3-hydroxy-4-piperidinyl)benzamide derivatives |
| CA1183847A (en) | 1981-10-01 | 1985-03-12 | Georges Van Daele | N-(3-hydroxy-4-piperidinyl)benzamide derivatives |
| FR2527608B1 (fr) * | 1982-05-28 | 1986-10-10 | Sandoz Sa | Nouveaux composes heterocycliques, leur preparation et leur utilisation comme medicaments |
| US4692443A (en) * | 1983-10-17 | 1987-09-08 | Eli Lilly And Company | 3-bicyclicpyridinium-methyl cephalosporins |
| NZ209833A (en) | 1983-10-17 | 1988-04-29 | Lilly Co Eli | 3-bicyclicpyridiniummethyl-cephalosporins and pharmaceutical compositions |
| GB8501542D0 (en) | 1985-01-22 | 1985-02-20 | Erba Farmitalia | 4 5 6 7-tetrahydro-imidazo(4 5-clpyridine derivatives |
| GB8530602D0 (en) | 1985-12-12 | 1986-01-22 | Fujisawa Pharmaceutical Co | Heterocyclic compounds |
| EG17993A (en) | 1986-02-03 | 1991-08-30 | Janssen Pharmaceutica Nv | Anti-histaminic compositions containing n-heterocyclyl-4-piperidinanines |
| US4804658A (en) * | 1986-09-15 | 1989-02-14 | G. D. Searle & Co. | Imidazopyridine derivatives and pharmaceutical compositions |
| WO1988009661A1 (en) * | 1987-06-10 | 1988-12-15 | Pfizer Inc. | Oxazolidin-2-one derivatives as hypoglycemic agents |
| US5057517A (en) * | 1987-07-20 | 1991-10-15 | Merck & Co., Inc. | Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents |
| IL87149A (en) | 1987-07-20 | 1994-05-30 | Merck & Co Inc | 6-Piperazinyl derivatives of purine and its 3- and 9-deaza isosteres, their preparation and pharmaceutical compositions containing them |
| US5227384A (en) * | 1988-03-14 | 1993-07-13 | G. D. Searle & Co. | 5-substituted [4,5-c] imidazopyridines and pharmaceutical use thereof |
| US5302601A (en) * | 1988-03-14 | 1994-04-12 | G. D. Searle & Co. | 5-substituted imidazo[4,5-c]pyridines |
| US5019581A (en) * | 1988-03-14 | 1991-05-28 | G. D. Searle & Co. | 5-substituted (4,5-c) imidazopyridine compounds which have useful platelet activating factor antagonistic activity |
| US4914108A (en) * | 1988-03-14 | 1990-04-03 | G. D. Searle & Co. | 5-substituted(4,5-c)imidazopyridine compounds which have useful platelet activating factor antagonistic activity |
| US5332744A (en) * | 1989-05-30 | 1994-07-26 | Merck & Co., Inc. | Substituted imidazo-fused 6-membered heterocycles as angiotensin II antagonists |
| US4988707A (en) * | 1989-09-13 | 1991-01-29 | G. D. Searle & Co. | Pharmacologically active phenylalkanoyl substituted imidazo (4,5-C) pyridines |
| US4990518A (en) * | 1989-09-13 | 1991-02-05 | G. D. Searle & Co. | Pharmacologically active heteroaryl substituted imidazo (4,5-c) pyridines |
| FR2663332B1 (fr) | 1990-06-15 | 1997-11-07 | Roussel Uclaf | Nouvelles cephalosporines comportant en position 3 un radical propenyle substitue par un ammonium quaternaire, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus. |
| US5011832A (en) * | 1990-06-26 | 1991-04-30 | Merck & Co., Inc. | 2-biphenyl-carbapenem antibacterial agents |
| JPH04327587A (ja) | 1991-04-26 | 1992-11-17 | Asahi Chem Ind Co Ltd | ６’−ｃ−アルキル−３−デアザネプラノシンａ誘導体、その製造法およびその用途 |
| GB9116056D0 (en) * | 1991-07-24 | 1991-09-11 | British Bio Technology | Compounds |
| US5587372A (en) * | 1991-12-12 | 1996-12-24 | Roussel Uclaf | Cephalosporins |
| GB9202792D0 (en) | 1992-02-11 | 1992-03-25 | British Bio Technology | Compounds |
| DE4211474A1 (de) | 1992-04-06 | 1993-10-07 | Merck Patent Gmbh | Imidazopyridine |
| US5208242A (en) * | 1992-08-26 | 1993-05-04 | G. D. Searle & Co. | 5-substituted-4-phenyl-5H-imidazo[4,5-c]pyridine derivatives |
| DE4230464A1 (de) | 1992-09-11 | 1994-03-17 | Merck Patent Gmbh | Imidazolderivate |
| DE4236026A1 (de) * | 1992-10-24 | 1994-04-28 | Merck Patent Gmbh | Imidazopyridine |
| JP3115455B2 (ja) | 1992-12-18 | 2000-12-04 | 明治製菓株式会社 | 新規セファロスポリン誘導体 |
| US5374638A (en) * | 1993-03-19 | 1994-12-20 | Merck & Co., Inc. | Six membered ring fused imidazoles substituted with phenoxyphenylacetic acid derivatives used to treat asthma |
| DE4309969A1 (de) | 1993-03-26 | 1994-09-29 | Bayer Ag | Substituierte heteroanellierte Imidazole |
| DE4318813A1 (de) * | 1993-06-07 | 1994-12-08 | Merck Patent Gmbh | Imidazopyridine |
| DE4324580A1 (de) * | 1993-07-22 | 1995-01-26 | Thomae Gmbh Dr K | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US5486525A (en) * | 1993-12-16 | 1996-01-23 | Abbott Laboratories | Platelet activating factor antagonists: imidazopyridine indoles |
| US5563143A (en) | 1994-09-21 | 1996-10-08 | Pfizer Inc. | Catechol diether compounds as inhibitors of TNF release |
| US5585492A (en) * | 1994-10-11 | 1996-12-17 | G. D. Searle & Co. | LTA4 Hydrolase inhibitors |
| US6506876B1 (en) | 1994-10-11 | 2003-01-14 | G.D. Searle & Co. | LTA4 hydrolase inhibitor pharmaceutical compositions and methods of use |
| US5880140A (en) | 1996-04-03 | 1999-03-09 | Merck & Co., Inc. | Biheteroaryl inhibitors of farnesyl-protein transferase |
| US5872136A (en) | 1996-04-03 | 1999-02-16 | Merck & Co., Inc. | Arylheteroaryl inhibitors of farnesyl-protein transferase |
| US6080870A (en) | 1996-04-03 | 2000-06-27 | Merck & Co., Inc. | Biaryl substituted imidazole compounds useful as farnesyl-protein transferase inhibitors |
| US5939557A (en) | 1996-04-03 | 1999-08-17 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5859035A (en) | 1996-04-03 | 1999-01-12 | Merck & Co., Inc. | Arylheteroaryl inhibitors of farnesyl-protein transferase |
| US6063930A (en) | 1996-04-03 | 2000-05-16 | Merck & Co., Inc. | Substituted imidazole compounds useful as farnesyl-protein transferase inhibitors |
| US5854265A (en) | 1996-04-03 | 1998-12-29 | Merck & Co., Inc. | Biheteroaryl inhibitors of farnesyl-protein transferase |
| US5883105A (en) | 1996-04-03 | 1999-03-16 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5874452A (en) | 1996-04-03 | 1999-02-23 | Merck & Co., Inc. | Biheteroaryl inhibitors of farnesyl-protein transferase |
| DE69817393T2 (de) * | 1997-11-28 | 2004-06-17 | Sumitomo Pharmaceuticals Co., Ltd. | Neue heterozyklische verbindungen |
| DE19845153A1 (de) * | 1998-10-01 | 2000-04-06 | Merck Patent Gmbh | Imidazo[4,5]-pyridin-4-on-derivate |
| DE69932263T2 (de) | 1999-01-08 | 2007-06-06 | Chisso Corp. | Borderivate und organische elektrolumineszierende verbindungen |
| DE19900471A1 (de) | 1999-01-08 | 2000-07-13 | Merck Patent Gmbh | Imidazo[4,5c]-pyridin-4-on-derivate |
| CA2373073A1 (en) | 1999-05-07 | 2000-11-16 | Takeda Chemical Industries, Ltd. | Cyclic compounds and uses thereof |
| US6844367B1 (en) | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
| WO2001047883A1 (fr) | 1999-12-27 | 2001-07-05 | Japan Tobacco Inc. | Composes a cycles accoles et leur utilisation comme medicaments |
| US6770666B2 (en) * | 1999-12-27 | 2004-08-03 | Japan Tobacco Inc. | Fused-ring compounds and use thereof as drugs |
| ATE311366T1 (de) | 2000-02-29 | 2005-12-15 | Millennium Pharm Inc | Benzamide und ähnliche inhibitoren vom faktor xa |
| EP1132381A1 (en) | 2000-03-08 | 2001-09-12 | Cermol S.A. | Ester derivatives of dimethylpropionic acid and pharmaceutical compositions containing them |
| US6448281B1 (en) * | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| KR100892614B1 (ko) | 2001-04-17 | 2009-04-09 | 다이닛본 스미토모 세이야꾸 가부시끼가이샤 | 신규 아데닌 유도체 |
| AR035543A1 (es) | 2001-06-26 | 2004-06-16 | Japan Tobacco Inc | Agente terapeutico para la hepatitis c que comprende un compuesto de anillo condensado, compuesto de anillo condensado, composicion farmaceutica que lo comprende, compuestos de benzimidazol, tiazol y bifenilo utiles como intermediarios para producir dichos compuestos, uso del compuesto de anillo con |
| US20030073836A1 (en) | 2001-07-05 | 2003-04-17 | Boehringer Ingelheim Pharma Kg | Heteroarylcarboxylic acid amides, the preparation thereof and their use as pharmaceutical compositions |
| US7294457B2 (en) * | 2001-08-07 | 2007-11-13 | Boehringer Ingelheim (Canada) Ltd. | Direct binding assay for identifying inhibitors of HCV polymerase |
| DE10140246A1 (de) | 2001-08-09 | 2003-03-06 | Forsch Pigmente Und Lacke E V | Verfahren zur Behandlung von Oberflächen von Substraten |
| WO2003026587A2 (en) | 2001-09-26 | 2003-04-03 | Bristol-Myers Squibb Company | Compounds useful for treating hepatitus c virus |
| JP2005525309A (ja) | 2002-01-10 | 2005-08-25 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | 医薬品としての使用のためのＭＴＰインヒビター又はａｐｏＢ分泌インヒビターとフィブレートの組み合わせ |
| GB0215293D0 (en) | 2002-07-03 | 2002-08-14 | Rega Foundation | Viral inhibitors |
| HRP20050157B1 (en) | 2002-08-21 | 2013-01-31 | Boehringer Ingelheim Pharma | 8-[3-amino-piperidin-1-yl]-xanthines,the production thereof and the use of the same as medicaments |
| BR0313923A (pt) * | 2002-08-29 | 2005-07-12 | Boehringer Ingelheim Pharma | Derivados de 3-(sulfonamidoetil)-indol para uso como miméticos de glicocorticóide no tratamento de doenças inflamatórias, alérgicas e proliferativas |
| BR0317230A (pt) | 2002-12-13 | 2005-10-25 | Smithkline Beecham Corp | Composto, composição, métodos de antagonizar uma atividade do receptor de quimiocina ccr-5, e de tratar uma infecção viral em um paciente, e, uso de um composto |
| US7098231B2 (en) | 2003-01-22 | 2006-08-29 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7223785B2 (en) | 2003-01-22 | 2007-05-29 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| JP2006515014A (ja) | 2003-01-30 | 2006-05-18 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | ＰＫＣ−θのインヒビターとして有用な２，４−ジアミノピリミジン誘導体 |
| US7566707B2 (en) | 2003-06-18 | 2009-07-28 | Boehringer Ingelheim International Gmbh | Imidazopyridazinone and imidazopyridone derivatives, the preparation thereof and their use as pharmaceutical compositions |
| CN1875002B (zh) | 2003-11-05 | 2011-08-03 | 霍夫曼-拉罗奇有限公司 | 作为ppar激动剂的苯基衍生物 |
| CA2574220C (en) | 2004-07-27 | 2014-09-16 | Gilead Sciences, Inc. | Imidazo[4,5-d]pyrimidines, their uses and methods of preparation |
| WO2006029966A1 (en) | 2004-09-13 | 2006-03-23 | Ciba Specialty Chemicals Holding Inc. | Alkylaminoacetamide lubricant additives |
| KR101143596B1 (ko) | 2006-07-07 | 2012-05-11 | 길리애드 사이언시즈, 인코포레이티드 | 신규의 피리다진 화합물 및 이의 용도 |
| UA99466C2 (en) | 2007-07-06 | 2012-08-27 | Гилиад Сайенсиз, Инк. | Crystalline pyridazine compound |
-
2005
- 2005-12-21 SI SI200530691T patent/SI1841765T1/sl unknown
- 2005-12-21 CA CA2592388A patent/CA2592388C/en not_active Expired - Fee Related
- 2005-12-21 NZ NZ556624A patent/NZ556624A/en not_active IP Right Cessation
- 2005-12-21 ES ES05855097T patent/ES2324794T3/es not_active Expired - Lifetime
- 2005-12-21 EP EP05855097A patent/EP1841765B1/en not_active Expired - Lifetime
- 2005-12-21 AU AU2005319167A patent/AU2005319167B2/en not_active Ceased
- 2005-12-21 DE DE602005013580T patent/DE602005013580D1/de not_active Expired - Lifetime
- 2005-12-21 PT PT05855097T patent/PT1841765E/pt unknown
- 2005-12-21 DK DK05855097T patent/DK1841765T5/da active
- 2005-12-21 PL PL05855097T patent/PL1841765T3/pl unknown
- 2005-12-21 JP JP2007548448A patent/JP2008524335A/ja not_active Withdrawn
- 2005-12-21 AT AT05855097T patent/ATE426601T1/de active
- 2005-12-21 US US11/316,050 patent/US20060252791A1/en not_active Abandoned
- 2005-12-21 WO PCT/US2005/046477 patent/WO2006069193A2/en not_active Ceased
-
2008
- 2008-01-30 US US12/022,557 patent/US7795276B2/en not_active Expired - Fee Related
-
2009
- 2009-05-21 CY CY20091100537T patent/CY1109087T1/el unknown
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2012
- 2012-07-02 JP JP2012148683A patent/JP2012184265A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007518720A (ja) * | 2003-12-22 | 2007-07-12 | カー・イュー・ルーベン・リサーチ・アンド・ディベロップメント | イミダゾ［４，５−ｃ］ピリジン化合物および抗ウイルス治療の方法 |
| JP4970048B2 (ja) * | 2003-12-22 | 2012-07-04 | カトリーケ・ウニフェルジテイト・ルーベン・カー・イュー・ルーベン・アール・アンド・ディ | イミダゾ［４，５−ｃ］ピリジン化合物および抗ウイルス治療の方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| PL1841765T3 (pl) | 2009-08-31 |
| DK1841765T5 (da) | 2009-12-21 |
| CY1109087T1 (el) | 2014-07-02 |
| AU2005319167A1 (en) | 2006-06-29 |
| ES2324794T3 (es) | 2009-08-14 |
| EP1841765A2 (en) | 2007-10-10 |
| HK1113570A1 (en) | 2008-10-10 |
| ATE426601T1 (de) | 2009-04-15 |
| US20080188516A1 (en) | 2008-08-07 |
| PT1841765E (pt) | 2009-05-14 |
| US20060252791A1 (en) | 2006-11-09 |
| SI1841765T1 (sl) | 2009-08-31 |
| DE602005013580D1 (de) | 2009-05-07 |
| CA2592388A1 (en) | 2006-06-29 |
| WO2006069193A3 (en) | 2006-08-10 |
| JP2012184265A (ja) | 2012-09-27 |
| CA2592388C (en) | 2013-04-02 |
| EP1841765B1 (en) | 2009-03-25 |
| NZ556624A (en) | 2010-06-25 |
| AU2005319167B2 (en) | 2011-09-29 |
| US7795276B2 (en) | 2010-09-14 |
| WO2006069193A2 (en) | 2006-06-29 |
| DK1841765T3 (da) | 2009-06-02 |
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