AP813A - Urea derivatives as inhibitors of IMPDH enzyme. - Google Patents
Urea derivatives as inhibitors of IMPDH enzyme. Download PDFInfo
- Publication number
- AP813A AP813A APAP/P/1997/000973A AP9700973A AP813A AP 813 A AP813 A AP 813A AP 9700973 A AP9700973 A AP 9700973A AP 813 A AP813 A AP 813A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Health & Medical Sciences (AREA)
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- General Health & Medical Sciences (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/636,361 US5807876A (en) | 1996-04-23 | 1996-04-23 | Inhibitors of IMPDH enzyme |
| US08/801,780 US6344465B1 (en) | 1996-04-23 | 1997-02-14 | Inhibitors of IMPDH enzyme |
| US08/832,165 US6054472A (en) | 1996-04-23 | 1997-04-02 | Inhibitors of IMPDH enzyme |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9700973A0 AP9700973A0 (en) | 1997-07-31 |
| AP813A true AP813A (en) | 2000-02-28 |
Family
ID=27417590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1997/000973A AP813A (en) | 1996-04-23 | 1997-04-23 | Urea derivatives as inhibitors of IMPDH enzyme. |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US6541496B1 (en:Method) |
| EP (1) | EP0902782A1 (en:Method) |
| CN (2) | CN1515248A (en:Method) |
| AP (1) | AP813A (en:Method) |
| AU (1) | AU723730B2 (en:Method) |
| BG (1) | BG64507B1 (en:Method) |
| BR (1) | BR9708735A (en:Method) |
| CA (1) | CA2252465C (en:Method) |
| CZ (1) | CZ298463B6 (en:Method) |
| EA (1) | EA004771B1 (en:Method) |
| HU (1) | HUP0004421A3 (en:Method) |
| ID (1) | ID16664A (en:Method) |
| IL (1) | IL126674A (en:Method) |
| IN (1) | IN190508B (en:Method) |
| NO (1) | NO312963B1 (en:Method) |
| NZ (1) | NZ332405A (en:Method) |
| OA (1) | OA10902A (en:Method) |
| PL (1) | PL192628B1 (en:Method) |
| SK (1) | SK286662B6 (en:Method) |
| TR (1) | TR199802136T2 (en:Method) |
| WO (1) | WO1997040028A1 (en:Method) |
Families Citing this family (160)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0932617T3 (da) * | 1996-10-18 | 2002-04-22 | Vertex Pharma | Inhibitorer af serinproteaser, især af hepatitis C-virus-NS3-protease |
| JP2001508767A (ja) * | 1996-12-02 | 2001-07-03 | 藤沢薬品工業株式会社 | ５―ｈｔ拮抗作用を有するインドール―ウレア誘導体 |
| EP1366766A1 (en) * | 1997-03-14 | 2003-12-03 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
| US6093742A (en) * | 1997-06-27 | 2000-07-25 | Vertex Pharmaceuticals, Inc. | Inhibitors of p38 |
| TR200001179T2 (tr) | 1997-10-31 | 2000-11-21 | Aventis Pharma Ltd. | Değiştirilmiş anilidler |
| TR200002618T2 (tr) * | 1997-12-22 | 2001-04-20 | Bayer Corporation | Sübstitüe edilmiş heterosiklik üreler kullanılarak raf kinazın inhibe edilmesi |
| US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| US7329670B1 (en) | 1997-12-22 | 2008-02-12 | Bayer Pharmaceuticals Corporation | Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas |
| ATE346600T1 (de) * | 1997-12-22 | 2006-12-15 | Bayer Pharmaceuticals Corp | Inhibierung der p38 kinase-aktivität durch die verwendung von aryl- und heteroarylsubstituierten harnstoffen |
| WO1999055663A1 (en) * | 1998-04-29 | 1999-11-04 | Vertex Pharmaceuticals Incorporated | Inhibitors of impdh enzyme |
| WO1999062869A1 (en) * | 1998-06-04 | 1999-12-09 | Kumiai Chemical Industry Co., Ltd. | Phenylacetylene derivatives and agricultural/horticultural bactericides |
| ATE286021T1 (de) * | 1998-10-22 | 2005-01-15 | Neurosearch As | Substituierte phenylderivate, ihre herstellung und verwendung |
| US6420403B1 (en) | 1998-10-29 | 2002-07-16 | Edwin J. Iwanowicz | Inhibitors of IMPDH enzyme |
| US6596747B2 (en) | 1998-10-29 | 2003-07-22 | Bristol-Myers Squibb Company | Compounds derived from an amine nucleus and pharmaceutical compositions comprising same |
| CA2348267A1 (en) | 1998-10-29 | 2000-05-11 | Henry H. Gu | Novel inhibitors of impdh enzyme |
| JP2002528499A (ja) | 1998-10-29 | 2002-09-03 | ブリストル−マイヤーズ スクイブ カンパニー | Ｉｍｐｄｈ酵素のインヒビターであるアミノ核誘導化合物 |
| GB9823873D0 (en) | 1998-10-30 | 1998-12-30 | Pharmacia & Upjohn Spa | 2-ureido-thiazole derivatives,process for their preparation,and their use as antitumour agents |
| RU2233269C2 (ru) * | 1998-11-02 | 2004-07-27 | Авентис Фарма Лимитед | Замещенные анилиды, фармацевтическая композиция и способ лечения |
| US6166028A (en) * | 1998-12-09 | 2000-12-26 | American Home Products Corporation | Diaminopuridine-containing thiourea inhibitors of herpes viruses |
| CN1332725A (zh) * | 1998-12-09 | 2002-01-23 | 美国家庭用品有限公司 | 疱疹病毒的硫脲抑制剂 |
| US6201013B1 (en) | 1998-12-09 | 2001-03-13 | American Home Products Corporation | Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group |
| US6262090B1 (en) | 1998-12-09 | 2001-07-17 | American Home Products Corporation | Aminopyridine-containing thiourea inhibitors of herpes viruses |
| AU1934600A (en) * | 1998-12-09 | 2000-06-26 | Wyeth | Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group |
| WO2000035455A1 (en) * | 1998-12-15 | 2000-06-22 | Telik, Inc. | Heteroaryl-aryl ureas as igf-1 receptor antagonists |
| AU1689600A (en) * | 1998-12-22 | 2000-07-12 | Mitsubishi Chemical Corporation | Amide derivatives |
| RU2319693C9 (ru) | 1999-01-13 | 2008-08-20 | Байер Копэрейшн | Производные мочевины (варианты), фармацевтическая композиция (варианты) и способ лечения заболевания, связанного с ростом раковых клеток (варианты) |
| ATE538794T1 (de) | 1999-01-13 | 2012-01-15 | Bayer Healthcare Llc | Gamma carboxyarylsubstituierte diphenylharnstoffverbindungen als p38 kinasehemmer |
| EP1140840B1 (en) | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US7928239B2 (en) | 1999-01-13 | 2011-04-19 | Bayer Healthcare Llc | Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas |
| HUP0202248A3 (en) * | 1999-03-12 | 2006-06-28 | Boehringer Ingelheim Pharma | Compounds useful as anti-inflammatory agents |
| ES2405316T3 (es) * | 1999-03-19 | 2013-05-30 | Vertex Pharmaceuticals Incorporated | Inhibidores de la enzima IMPDH |
| US6653309B1 (en) | 1999-04-26 | 2003-11-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme technical field of the invention |
| AU5031200A (en) * | 1999-05-28 | 2000-12-18 | Vertex Pharmaceuticals Incorporated | Method for preparing 5-substituted oxazoles |
| US6107052A (en) * | 1999-06-09 | 2000-08-22 | Roche Diagnostics Corporation | Enzymatic measurement of mycophenolic acid |
| DK1196414T3 (da) * | 1999-06-25 | 2003-11-24 | Vertex Pharma | Prolægemiddel af carbamathæmmer for IMPDH |
| JP2001011059A (ja) * | 1999-06-28 | 2001-01-16 | Nippon Synthetic Chem Ind Co Ltd:The | ５−（２−置換−４−ニトロフェニル）−オキサゾールの製造方法 |
| JP2001011060A (ja) * | 1999-06-28 | 2001-01-16 | Nippon Synthetic Chem Ind Co Ltd:The | 新規オキサゾール化合物及びその製造方法 |
| TWI262185B (en) * | 1999-10-01 | 2006-09-21 | Eisai Co Ltd | Carboxylic acid derivatives having anti-hyperglycemia and anti-hyperlipemia action, and pharmaceutical composition containing the derivatives |
| US6867299B2 (en) | 2000-02-24 | 2005-03-15 | Hoffmann-La Roche Inc. | Oxamide IMPDH inhibitors |
| CA2407370A1 (en) | 2000-04-24 | 2001-11-01 | Bristol-Myers Squibb Company | Heterocycles that are inhibitors of impdh enzyme |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| US6423849B1 (en) | 2000-09-01 | 2002-07-23 | The Nippon Synthetic Chemical Industry Co., Ltd. | Process of preparing 5-(2-substituted-4-nitrophenyl)-oxazole, novel oxazole compound, and process of preparing the same |
| US7235576B1 (en) | 2001-01-12 | 2007-06-26 | Bayer Pharmaceuticals Corporation | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US7371763B2 (en) | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
| US6593362B2 (en) * | 2001-05-21 | 2003-07-15 | Guilford Pharmaceuticals Inc. | Non-peptidic cyclophilin binding compounds and their use |
| TW200301698A (en) | 2001-12-21 | 2003-07-16 | Bristol Myers Squibb Co | Acridone inhibitors of IMPDH enzyme |
| SI1580188T1 (sl) | 2002-02-11 | 2012-02-29 | Bayer Healthcare Llc | Aril sečnine kot kinazni inhibitorji |
| DK1478358T3 (da) | 2002-02-11 | 2013-10-07 | Bayer Healthcare Llc | Sorafenibtosylat til behandling af sygdomme kendetegnet ved unormal angiogenese |
| EP1402887A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | New compounds for the inhibition of undesired cell proliferation and use thereof |
| ATE424198T1 (de) | 2002-12-06 | 2009-03-15 | Vertex Pharma | Zusammensetzungen die eine kombination von diphenylharnstoff impdh-hemmern und apoptose- induzierenden antikrebsmitteln enthalten |
| WO2004060346A2 (en) | 2002-12-30 | 2004-07-22 | Angiotech International Ag | Drug delivery from rapid gelling polymer composition |
| US7220768B2 (en) * | 2003-02-11 | 2007-05-22 | Wyeth Holdings Corp. | Isoxazole-containing thiourea inhibitors useful for treatment of varicella zoster virus |
| US20070020704A1 (en) | 2003-05-20 | 2007-01-25 | Scott Wilhelm | Diaryl ureas with kinase inhibiting activity |
| US8637553B2 (en) | 2003-07-23 | 2014-01-28 | Bayer Healthcare Llc | Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of diseases and conditions |
| PE20050374A1 (es) | 2003-09-05 | 2005-05-30 | Vertex Pharma | Inhibidores de proteasas de serina, en particular proteasa ns3-ns4a del vhc |
| NZ546663A (en) | 2003-10-10 | 2010-01-29 | Vertex Pharma | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
| AR045870A1 (es) * | 2003-10-11 | 2005-11-16 | Vertex Pharma | Terapia de combinacion para la infeccion de virus de hepatitis c |
| ES2389201T3 (es) * | 2003-10-27 | 2012-10-24 | Vertex Pharmaceuticals Incorporated | Mutantes de resistencia de la proteasa NS3/4A de HCV |
| EP1944042A1 (en) | 2003-10-27 | 2008-07-16 | Vertex Pharmceuticals Incorporated | Combinations for HCV treatment |
| AU2005212257A1 (en) | 2004-02-04 | 2005-08-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
| EP1568696A1 (en) * | 2004-02-26 | 2005-08-31 | 4Sc Ag | Compounds as inhibitors of cell proliferation and viral infections |
| US7317030B2 (en) | 2004-02-26 | 2008-01-08 | 4Sc Ag | Compounds as inhibitors of cell proliferation and viral infections |
| US20110104186A1 (en) | 2004-06-24 | 2011-05-05 | Nicholas Valiante | Small molecule immunopotentiators and assays for their detection |
| PL1778686T3 (pl) | 2004-08-12 | 2009-04-30 | Pfizer | Pochodne triazolopirydynylosulfanylowe jako inhibitory kinazy MAP P38 |
| TW201300108A (zh) * | 2004-10-01 | 2013-01-01 | Vertex Pharma | Ｃ型肝炎病毒（ｈｃｖ）ｎｓ３-ｎｓ４ａ蛋白酶抑制劑 |
| TW201424733A (zh) | 2004-10-29 | 2014-07-01 | Vertex Pharma | 劑量型式 |
| EP1858877B1 (en) * | 2005-01-14 | 2014-03-12 | Gilead Connecticut, Inc. | 1,3 substituted diaryl ureas as modulators of kinase activity |
| WO2006076593A1 (en) * | 2005-01-14 | 2006-07-20 | Cgi Pharmaceuticals, Inc. | 1,3-diaryl substituted ureas as modulators of kinase activity |
| US20060235009A1 (en) * | 2005-02-08 | 2006-10-19 | Richard Glickman | Treatment of vascular, autoimmune and inflammatory diseases using low dosages of IMPDH inhibitors |
| EP1917010A2 (en) * | 2005-02-08 | 2008-05-07 | Aspreva Pharmaceuticals SA | Compositions and methods for treating vascular, autoimmune and inflammatory diseases |
| WO2006094626A1 (en) | 2005-03-07 | 2006-09-14 | Bayer Healthcare Ag | Pharmaceutical composition comprising an omega- carboxyaryl substituted diphenyl urea for the treatment of cancer |
| WO2007024294A2 (en) * | 2005-05-03 | 2007-03-01 | Cgi Pharmaceuticals, Inc. | Certain substituted ureas, as modulators of kinase activity |
| CA2606780A1 (en) * | 2005-05-09 | 2006-11-16 | Vertex Pharmaceuticals Incorporated | Processes for preparing biaryl ureas and analogs thereof |
| CN101175752A (zh) * | 2005-05-09 | 2008-05-07 | 沃泰克斯药物股份有限公司 | 3－(3－(3－甲氧基－4－(唑－5－基)苯基)脲基)苄基氨基甲酸(s)－四氢呋喃－3－基酯的多晶型 |
| PE20070210A1 (es) | 2005-07-29 | 2007-04-16 | Tibotec Pharm Ltd | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| PE20070211A1 (es) | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| JO2768B1 (en) | 2005-07-29 | 2014-03-15 | تيبوتيك فارماسيوتيكالز ليمتد | Large cyclic inhibitors of hepatitis C virus |
| US8183277B2 (en) | 2005-07-29 | 2012-05-22 | Tibotec Pharmaceuticals Ltd. | Macrocylic inhibitors of hepatitis C virus |
| TWI382025B (zh) | 2005-07-29 | 2013-01-11 | Tibotec Pharm Ltd | Ｃ型肝炎病毒之大環抑制劑（四） |
| US8012939B2 (en) | 2005-07-29 | 2011-09-06 | Tibotec Pharmaceuticals Ltd. Co | Macrocyclic inhibitors of hepatitis C virus |
| DK1912996T3 (da) | 2005-07-29 | 2012-09-17 | Janssen R & D Ireland | Makrocykliske inhibitorer af hepatitis C-virus |
| SI1919898T1 (sl) | 2005-07-29 | 2011-05-31 | Tibotec Pharm Ltd | Makrociklični inhibitorji virusa hepatitisa C |
| ATE524475T1 (de) | 2005-07-29 | 2011-09-15 | Tibotec Pharm Ltd | Makrocyclische inhibitoren des hepatitis-c-virus |
| KR20080033481A (ko) * | 2005-08-02 | 2008-04-16 | 버텍스 파마슈티칼스 인코포레이티드 | 세린 프로테아제의 억제제 |
| US7964624B1 (en) * | 2005-08-26 | 2011-06-21 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
| AR055395A1 (es) * | 2005-08-26 | 2007-08-22 | Vertex Pharma | Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c |
| US7705138B2 (en) | 2005-11-11 | 2010-04-27 | Vertex Pharmaceuticals Incorporated | Hepatitis C virus variants |
| RU2008123606A (ru) | 2005-11-11 | 2009-12-20 | Вертекс Фармасьютикалз, Инк (Us) | Варианты вируса гепатита с |
| CN102614490A (zh) | 2006-02-27 | 2012-08-01 | 弗特克斯药品有限公司 | 包含vx-950的共晶体和包含所述共晶体的药物组合物 |
| JP2009531315A (ja) | 2006-03-16 | 2009-09-03 | バーテックス ファーマシューティカルズ インコーポレイテッド | 重水素化ｃ型肝炎プロテアーゼインヒビター |
| RU2448976C2 (ru) | 2006-04-11 | 2012-04-27 | Новартис Аг | Ингибиторы hcv/вич и их применение |
| US20080076770A1 (en) * | 2006-09-25 | 2008-03-27 | Arete Therapeutics, Inc. | Soluble epoxide hydrolase inhibitors |
| WO2008040778A2 (en) | 2006-10-04 | 2008-04-10 | Tibotec Pharmaceuticals Ltd. | Carboxamide 4-[(4-pyridyl)amino] pyrimidines for the treatment of hepatitis c |
| WO2008059046A1 (en) | 2006-11-17 | 2008-05-22 | Tibotec Pharmaceuticals Ltd. | Macrocyclic inhibitors of hepatitis c virus |
| NZ579295A (en) * | 2007-02-27 | 2012-03-30 | Vertex Pharma | Inhibitors of serine proteases |
| AP2009004960A0 (en) * | 2007-02-27 | 2009-08-31 | Vertex Pharma | Co-crystals and pharmaceutical compositions comprising the same |
| AU2008242767A1 (en) * | 2007-04-20 | 2008-10-30 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| NZ580917A (en) | 2007-05-04 | 2012-06-29 | Vertex Pharma | Combinations of protease inhibitors such as VX-950 and polymerase inhibitors for the treatment of HCV infection |
| NZ583699A (en) * | 2007-08-30 | 2012-04-27 | Vertex Pharma | Co-crystals of vx-950 (telaprevir) other components and pharmaceutical compositions comprising the same |
| BRPI0821836A2 (pt) | 2007-12-24 | 2015-06-16 | Tibotec Pharm Ltd | Indóis macrocíclicos como inibidores do vírus da hepatite c |
| TWI454476B (zh) | 2008-07-08 | 2014-10-01 | Tibotec Pharm Ltd | 用作ｃ型肝炎病毒抑制劑之巨環吲哚衍生物 |
| DK2331554T3 (da) | 2008-08-14 | 2013-05-27 | Janssen R & D Ireland | Makrocykliske indolderivater, der er anvendelige som hepatitis c-virusinhibitorer |
| KR20110098779A (ko) | 2008-12-03 | 2011-09-01 | 프레시디오 파마슈티칼스, 인코포레이티드 | Ｈｃｖ ｎｓ5ａ의 억제제 |
| EA024853B1 (ru) | 2008-12-03 | 2016-10-31 | Пресидио Фармасьютикалс, Инк. | Ингибиторы ns5a вгс |
| EP2396028A2 (en) | 2009-02-12 | 2011-12-21 | Vertex Pharmceuticals Incorporated | Hcv combination therapies comprising pegylated interferon, ribavirin and telaprevir |
| WO2010108187A2 (en) | 2009-03-20 | 2010-09-23 | Brandeis University | Compounds and methods for treating mammalian gastrointestinal microbial infections |
| KR20110131312A (ko) | 2009-03-27 | 2011-12-06 | 프레시디오 파마슈티칼스, 인코포레이티드 | 융합된 고리 ｃ형 간염 억제제 |
| US20110182850A1 (en) | 2009-04-10 | 2011-07-28 | Trixi Brandl | Organic compounds and their uses |
| US8512690B2 (en) | 2009-04-10 | 2013-08-20 | Novartis Ag | Derivatised proline containing peptide compounds as protease inhibitors |
| WO2011014882A1 (en) | 2009-07-31 | 2011-02-03 | Medtronic, Inc. | CONTINUOUS SUBCUTANEOUS ADMINISTRATION OF INTERFERON-α TO HEPATITIS C INFECTED PATIENTS |
| UA108211C2 (uk) | 2009-11-04 | 2015-04-10 | Янссен Рід Айрленд | Бензімідазолімідазольні похідні |
| CN102844030A (zh) | 2010-01-29 | 2012-12-26 | 沃泰克斯药物股份有限公司 | 用于治疗丙型肝炎病毒感染的疗法 |
| WO2011112516A1 (en) | 2010-03-08 | 2011-09-15 | Ico Therapeutics Inc. | Treating and preventing hepatitis c virus infection using c-raf kinase antisense oligonucleotides |
| EP2575866A4 (en) | 2010-05-24 | 2013-10-16 | Presidio Pharmaceuticals Inc | HCV NS5A INHIBITORS |
| KR101580714B1 (ko) | 2010-06-03 | 2016-01-04 | 파마싸이클릭스 엘엘씨 | 브루톤 티로신 인산화효소(ｂｔｋ)의 억제제의 용도 |
| WO2011156545A1 (en) | 2010-06-09 | 2011-12-15 | Vertex Pharmaceuticals Incorporated | Viral dynamic model for hcv combination therapy |
| BR112012032889A2 (pt) | 2010-06-24 | 2015-09-15 | Janssen R & D Ireland | preparação do ácido 13-ciclo-hexil-3-metóxi-6-[metil-(2-{2-[metil-(sulfamoil)-amino]-etóxi}-etil)-carbamoil]-7h-indol-[2,1-a]-[2]-benzazepina-10-carboxílico |
| TW201208704A (en) | 2010-07-14 | 2012-03-01 | Vertex Pharma | Palatable pharmaceutical composition |
| WO2012020036A1 (en) | 2010-08-13 | 2012-02-16 | F. Hoffmann-La Roche Ag | Hepatitis c virus inhibitors |
| WO2012109646A1 (en) | 2011-02-11 | 2012-08-16 | Vertex Pharmaceuticals Incorporated | Treatment of hcv in hiv infection patients |
| CN102985104A (zh) | 2011-02-25 | 2013-03-20 | 麦德托尼克公司 | 在干扰素-α治疗方案中使用药代动力学分布和药效动力学分布的方法和系统 |
| WO2012123298A1 (en) | 2011-03-11 | 2012-09-20 | F. Hoffmann-La Roche Ag | Antiviral compounds |
| WO2012175700A1 (en) | 2011-06-23 | 2012-12-27 | Digna Biotech, S. L. | Treatment of chronic hepatitis c with ifn-a5 combined with ifn-a2b in a cohort of patients |
| US20120328565A1 (en) | 2011-06-24 | 2012-12-27 | Brinkman John A | Antiviral compounds |
| EP2766365A1 (en) | 2011-10-10 | 2014-08-20 | F.Hoffmann-La Roche Ag | Antiviral compounds |
| BR112014013972A8 (pt) | 2011-12-16 | 2017-06-13 | Hoffmann La Roche | inibidores de hcv nssa |
| CA2869317C (en) | 2011-12-20 | 2016-05-17 | F. Hoffmann-La Roche Ag | 4'-azido,3'-fluoro substituted nucleoside derivatives as inhibitors of hcv rna replication |
| ES2636448T3 (es) | 2011-12-20 | 2017-10-05 | Riboscience Llc | Derivados de nucleósido 2',4'-difluoro-2'-metil sustituidos como inhibidores de la replicación del ARN del VHC |
| AU2012360905B2 (en) | 2011-12-28 | 2017-04-27 | Janssen Sciences Ireland Uc | Hetero-bicyclic derivatives as HCV inhibitors |
| US20130195797A1 (en) | 2012-01-31 | 2013-08-01 | Vertex Pharmaceuticals Incorporated | High potency formulations of vx-950 |
| WO2013124335A1 (en) | 2012-02-24 | 2013-08-29 | F. Hoffmann-La Roche Ag | Antiviral compounds |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| US20140010783A1 (en) | 2012-07-06 | 2014-01-09 | Hoffmann-La Roche Inc. | Antiviral compounds |
| MX2015001081A (es) | 2012-07-24 | 2015-10-14 | Pharmacyclics Inc | Mutaciones asociadas a resistencia a inhibidores de la tirosina cinasa de bruton (btk). |
| US9447134B2 (en) | 2012-08-17 | 2016-09-20 | Brandeis University | Compounds and methods for treating mammalian gastrointestinal microbial infections |
| US20140205566A1 (en) | 2012-11-30 | 2014-07-24 | Novartis Ag | Cyclic nucleuoside derivatives and uses thereof |
| CA2892589A1 (en) | 2013-01-23 | 2014-07-31 | F. Hoffmann-La Roche Ag | Antiviral triazole derivatives |
| JP6018715B2 (ja) | 2013-03-05 | 2016-11-02 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 抗ウイルス化合物 |
| US9895442B2 (en) | 2013-05-16 | 2018-02-20 | Riboscience Llc | 4′-fluoro-2′-methyl substituted nucleoside derivatives as inhibitors of HCV RNA replication |
| US20180200280A1 (en) | 2013-05-16 | 2018-07-19 | Riboscience Llc | 4'-Fluoro-2'-Methyl Substituted Nucleoside Derivatives as Inhibitors of HCV RNA Replication |
| EA201592185A1 (ru) | 2013-05-16 | 2016-05-31 | Рибосайенс Ллк | 4'-азидо, 3'-дезокси-3'-фторзамещенные нуклеозидные производные |
| EA201690746A1 (ru) | 2013-10-25 | 2016-12-30 | Фармасайкликс Элэлси | Лечение с применением ингибиторов тирозинкиназы брутона и иммунотерапии |
| US9885086B2 (en) | 2014-03-20 | 2018-02-06 | Pharmacyclics Llc | Phospholipase C gamma 2 and resistance associated mutations |
| AU2018335411B2 (en) | 2017-09-21 | 2024-06-27 | Riboscience Llc | 4'-fluoro-2'-methyl substituted nucleoside derivatives as inhibitors of HCV RNA replication |
| EP3746059A1 (en) | 2018-01-31 | 2020-12-09 | Deciphera Pharmaceuticals, LLC | Combination therapy for the treatment of gastrointestinal stromal tumors |
| WO2019152719A1 (en) | 2018-01-31 | 2019-08-08 | Deciphera Pharmaceuticals, Llc | Combination therapy for the treatment of mastocytosis |
| CA3094324A1 (en) | 2018-03-26 | 2019-10-03 | Clear Creek Bio, Inc. | Compositions and methods for inhibiting dihydroorotate dehydrogenase |
| CN109970675A (zh) * | 2018-05-28 | 2019-07-05 | 中国医学科学院医药生物技术研究所 | 一组硫脲化合物及其制备方法和应用 |
| SG11202012625PA (en) | 2018-06-19 | 2021-01-28 | Novartis Ag | N-substituted tetrahydrothienopyridine derivatives and uses thereof |
| US12098117B2 (en) * | 2018-12-11 | 2024-09-24 | Duke University | Compositions and methods for the treatment of cancer |
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| CA3150433A1 (en) | 2019-08-12 | 2021-02-18 | Deciphera Pharmaceuticals, Llc | Ripretinib for treating gastrointestinal stromal tumors |
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| DK4084779T3 (da) | 2019-12-30 | 2024-12-16 | Deciphera Pharmaceuticals Llc | Sammensætninger af 1-(4-brom-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro- 1,6-naphthyridin-3-yl)-2-fluorphenyl)-3-phenylurea |
| US20210300873A1 (en) | 2020-03-20 | 2021-09-30 | Clear Creek Bio, Inc. | Stable polymorphic compositions of brequinar sodium and methods of use and manufacture thereof |
| US20230218644A1 (en) | 2020-04-16 | 2023-07-13 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5380879A (en) * | 1994-02-18 | 1995-01-10 | Syntex (U.S.A.) Inc. | Derivatives of mycophenolic acid |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1171904A (en) | 1965-10-21 | 1969-11-26 | Unilever Ltd | Anilinobenzimidazoles having Antibacterial Properties |
| CA985286A (en) | 1971-05-04 | 1976-03-09 | Charles J. Paget (Jr.) | (substituted anilino) benzoxazoles useful in the prophylaxis of mareks disease |
| DE2928485A1 (de) * | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
| US5283257A (en) | 1992-07-10 | 1994-02-01 | The Board Of Trustees Of The Leland Stanford Junior University | Method of treating hyperproliferative vascular disease |
| WO1994012184A1 (en) | 1992-11-24 | 1994-06-09 | Syntex (U.S.A.) Inc. | Use of mycophenolic acid, mycophenolate mofetil or derivate thereof to inhibit stenosis |
| US5444072A (en) | 1994-02-18 | 1995-08-22 | Syntex (U.S.A.) Inc. | 6-substituted mycophenolic acid and derivatives |
-
1997
- 1997-04-21 TR TR1998/02136T patent/TR199802136T2/xx unknown
- 1997-04-21 SK SK1461-98A patent/SK286662B6/sk not_active IP Right Cessation
- 1997-04-21 CN CNA031002366A patent/CN1515248A/zh active Pending
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- 1997-04-21 WO PCT/US1997/006623 patent/WO1997040028A1/en not_active Ceased
- 1997-04-21 PL PL329639A patent/PL192628B1/pl not_active IP Right Cessation
- 1997-04-21 EP EP97918759A patent/EP0902782A1/en not_active Withdrawn
- 1997-04-21 HU HU0004421A patent/HUP0004421A3/hu not_active Application Discontinuation
- 1997-04-21 AU AU26785/97A patent/AU723730B2/en not_active Ceased
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- 1997-04-21 EA EA199800943A patent/EA004771B1/ru not_active IP Right Cessation
- 1997-04-21 CZ CZ0338098A patent/CZ298463B6/cs not_active IP Right Cessation
- 1997-04-22 IN IN702CA1997 patent/IN190508B/en unknown
- 1997-04-23 AP APAP/P/1997/000973A patent/AP813A/en active
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1998
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- 1998-11-23 BG BG102945A patent/BG64507B1/bg unknown
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2000
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2003
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5380879A (en) * | 1994-02-18 | 1995-01-10 | Syntex (U.S.A.) Inc. | Derivatives of mycophenolic acid |
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