NO328578B1 - Forbindelse samt anvendelse derav, og farmasoytisk preparat - Google Patents
Forbindelse samt anvendelse derav, og farmasoytisk preparat Download PDFInfo
- Publication number
- NO328578B1 NO328578B1 NO20035201A NO20035201A NO328578B1 NO 328578 B1 NO328578 B1 NO 328578B1 NO 20035201 A NO20035201 A NO 20035201A NO 20035201 A NO20035201 A NO 20035201A NO 328578 B1 NO328578 B1 NO 328578B1
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- Norway
- Prior art keywords
- pharmaceutically acceptable
- methyl
- mammal
- acceptable salt
- compound according
- Prior art date
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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| Application Number | Priority Date | Filing Date | Title |
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| US29477501P | 2001-05-31 | 2001-05-31 | |
| US34104801P | 2001-12-06 | 2001-12-06 | |
| PCT/IB2002/001905 WO2002096909A1 (en) | 2001-05-31 | 2002-05-29 | Optical resolution of (1-benzyl-4-methylpiperidin-3-yl) -methylamine and the use thereof for the preparation of pyrrolo 2,3-pyrimidine derivatives as protein kinases inhibitors |
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| NO20035201L NO20035201L (no) | 2003-11-24 |
| NO20035201D0 NO20035201D0 (no) | 2003-11-24 |
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| NO20093135A NO20093135L (no) | 2001-05-31 | 2009-10-13 | Optisk opplosning av (1-benzyl-4-metylpiperidin-3-yl) -metylamin og anvendelse derav for fremstilling av pyrrolo 2,3-pyrimidinderivater som protein kinase inhibitorer |
| NO2017047C NO2017047I1 (no) | 2001-05-31 | 2017-09-08 | Tofacitinib, evt. i form av et farmasøytisk akseptabelt salt, inkludert citratsalt |
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| NO2017047C NO2017047I1 (no) | 2001-05-31 | 2017-09-08 | Tofacitinib, evt. i form av et farmasøytisk akseptabelt salt, inkludert citratsalt |
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Families Citing this family (119)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| PT1235830E (pt) | 1999-12-10 | 2004-04-30 | Pfizer Prod Inc | Compostos de pirrolo¬2,3-d|pirimidina como inibidores das proteina cinases |
| SI1294724T1 (sl) * | 2000-06-26 | 2006-08-31 | Pfizer Prod Inc | Pirolo(2,3-d)primidinske spojine kot imunosupresivna sredstva |
| GT200200234A (es) | 2001-12-06 | 2003-06-27 | Compuestos cristalinos novedosos | |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| CN1678321A (zh) | 2002-07-29 | 2005-10-05 | 里格尔药品股份有限公司 | 用2,4－嘧啶二胺化合物治疗或者预防自体免疫性疾病的方法 |
| ATE402700T1 (de) * | 2002-08-27 | 2008-08-15 | Merck Patent Gmbh | Glycinamid-derivate als raf-kinase-hemmer |
| CA2507392A1 (en) | 2002-11-26 | 2004-06-10 | Pfizer Products Inc. | Method of treatment of transplant rejection |
| EP1656372B1 (en) | 2003-07-30 | 2013-04-10 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
| MXPA06012663A (es) * | 2004-05-03 | 2007-01-16 | Novartis Ag | Combinaciones que comprenden un agonista del receptor s1p y un inhibidor de quinasa jak3. |
| US7358250B2 (en) | 2004-06-29 | 2008-04-15 | Amgen Inc. | Pyrrolo[2,3-d]pyrimidines that modulate ACK1 activity |
| TW200615268A (en) | 2004-08-02 | 2006-05-16 | Osi Pharm Inc | Aryl-amino substituted pyrrolopyrimidine multi-kinase inhibiting compounds |
| WO2006056399A2 (en) * | 2004-11-24 | 2006-06-01 | Novartis Ag | Combinations of jak inhibitors and at least one of bcr-abl, flt-3, fak or raf kinase inhibitors |
| AR054416A1 (es) | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| SG137989A1 (en) | 2005-06-08 | 2008-01-28 | Rigel Pharmaceuticals Inc | Compositions and methods for inhibition of the JAK pathway |
| EP2251341A1 (en) | 2005-07-14 | 2010-11-17 | Astellas Pharma Inc. | Heterocyclic Janus kinase 3 inhibitors |
| US8163767B2 (en) | 2005-07-14 | 2012-04-24 | Astellas Pharma Inc. | Heterocyclic Janus Kinase 3 inhibitors |
| PL1913000T3 (pl) | 2005-07-29 | 2012-05-31 | Pfizer Prod Inc | Pochodne pirolo[2,3-d]pirymidyny, ich związki pośrednie i synteza |
| EP2270014A1 (en) | 2005-09-22 | 2011-01-05 | Incyte Corporation | Azepine inhibitors of janus kinases |
| ES2970354T3 (es) | 2005-12-13 | 2024-05-28 | Incyte Holdings Corp | Derivados de pirrolo[2,3-d]pirimidina como inhibidores de Janus quinasas |
| CA2642229C (en) | 2006-02-24 | 2015-05-12 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| GB0605691D0 (en) * | 2006-03-21 | 2006-05-03 | Novartis Ag | Organic Compounds |
| CA2673038C (en) | 2006-12-22 | 2015-12-15 | Incyte Corporation | Substituted tricyclic heteroaryl compounds as janus kinase inhibitors |
| CL2008001709A1 (es) | 2007-06-13 | 2008-11-03 | Incyte Corp | Compuestos derivados de pirrolo [2,3-b]pirimidina, moduladores de quinasas jak; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como cancer, psoriasis, artritis reumatoide, entre otras. |
| TR201903488T4 (tr) | 2007-06-13 | 2019-04-22 | Incyte Holdings Corp | Janus kinaz inhibitörü (r)-3-(4-(7h-pirolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)-3-siklopentilpropannitril tuzlarının kullanımı. |
| CN101743009A (zh) * | 2007-07-11 | 2010-06-16 | 辉瑞大药厂 | 治疗干眼病的药物组合物和方法 |
| WO2009103032A1 (en) | 2008-02-15 | 2009-08-20 | Rigel Pharmaceuticals, Inc. | Pyrimidine-2-amine compounds and their use as inhibitors of jak kinases |
| RS55263B1 (sr) | 2008-03-11 | 2017-02-28 | Incyte Holdings Corp | Derivati azetidina i ciklobutana kao jak inhibitori |
| US8138339B2 (en) | 2008-04-16 | 2012-03-20 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| NZ589315A (en) | 2008-04-16 | 2012-11-30 | Portola Pharm Inc | 2,6-diamino-pyrimidin-5-yl-carboxamides as Spleen tryosine kinase (syk) or Janus kinase (JAK) inhibitors |
| JP2011518219A (ja) | 2008-04-22 | 2011-06-23 | ポートラ ファーマシューティカルズ， インコーポレイテッド | タンパク質キナーゼの阻害剤 |
| KR20110050654A (ko) * | 2008-08-01 | 2011-05-16 | 바이오크리스트 파마수티컬즈, 인코퍼레이티드 | Ｊａｋ3 억제제로서의 피페리딘 유도체 |
| BRPI0917459B1 (pt) * | 2008-08-20 | 2017-09-12 | Zoetis Services Llc | N-methyl-1- [trans-4- [methyl (7h-pyrrol [2,3-d] pyridol [2,3-d] pyrimidine compounds, use of these in therapy and crystalline a form of n-methyl- pyrimidin-4-yl) amino] cyclohexyl} methanosulphonamide |
| US8592415B2 (en) * | 2009-02-11 | 2013-11-26 | Reaction Biology Corp. | Selective kinase inhibitors |
| CA2759026C (en) | 2009-04-20 | 2019-01-15 | Auspex Pharmaceuticals, Inc. | Piperidine inhibitors of janus kinase 3 |
| TWI484962B (zh) | 2009-05-22 | 2015-05-21 | Incyte Corp | 作為ｊａｋ抑制劑之３－〔４－（７ｈ－吡咯并〔２，３－ｄ〕嘧啶－４－基）－１ｈ－吡唑－１－基〕辛烷或庚腈 |
| KR101771401B1 (ko) | 2009-05-22 | 2017-08-25 | 인사이트 홀딩스 코포레이션 | 야누스 키나제 억제제로서 피라졸４일피롤로［２,３ｄ］피리미딘 및 피롤３일피롤로［２,３ｄ］피리미딘의 Ｎ(헤테로)아릴피롤리딘 유도체 |
| US9249145B2 (en) | 2009-09-01 | 2016-02-02 | Incyte Holdings Corporation | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| MX2012002641A (es) * | 2009-09-10 | 2012-03-14 | Hoffmann La Roche | Inhibidores de cinasa janus (jak). |
| EA021478B1 (ru) | 2009-10-09 | 2015-06-30 | Инсайт Корпорейшн | ГИДРОКСИЛЬНЫЕ, КЕТО И ГЛЮКУРОНИДНЫЕ ПРОИЗВОДНЫЕ 3-(4-(7Н-ПИРРОЛО[2,3-d]ПИРИМИДИН-4-ИЛ)-1Н-ПИРАЗОЛ-1-ИЛ)-3-ЦИКЛОПЕНТИЛПРОПАННИТРИЛА |
| CA2776028C (en) | 2009-10-15 | 2015-12-01 | Pfizer Inc. | Pyrrolo[2,3-d]pyrimidine compounds |
| JP5739446B2 (ja) | 2009-12-18 | 2015-06-24 | ファイザー・インク | ピロロ［２，３−ｄ］ピリミジン化合物 |
| WO2011086053A1 (en) * | 2010-01-12 | 2011-07-21 | F. Hoffmann-La Roche Ag | Tricyclic heterocyclic compounds, compositions and methods of use thereof |
| WO2011097087A1 (en) | 2010-02-05 | 2011-08-11 | Pfizer Inc. | Pyrrolo [ 2, 3 - d] pyrimidine urea compounds as jak inhibitors |
| DK2545045T3 (da) | 2010-03-10 | 2016-01-25 | Incyte Holdings Corp | Piperidin-4-yl-azetidinderivater som jak1-inhibitorer |
| CN103002875B (zh) | 2010-05-21 | 2016-05-04 | 因塞特控股公司 | Jak抑制剂的局部用制剂 |
| US9102625B2 (en) | 2010-11-01 | 2015-08-11 | Portola Pharmaceuticals, Inc. | Nicotinamides as JAK kinase modulators |
| US8933085B2 (en) | 2010-11-19 | 2015-01-13 | Incyte Corporation | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as JAK inhibitors |
| US9034884B2 (en) | 2010-11-19 | 2015-05-19 | Incyte Corporation | Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as JAK inhibitors |
| EP2481411A1 (en) | 2011-01-27 | 2012-08-01 | Ratiopharm GmbH | Oral dosage forms for modified release comprising the JAK3 inhibitor tasocitinib |
| EP2481397A1 (en) | 2011-01-27 | 2012-08-01 | Ratiopharm GmbH | Pharmaceutical compositions comprising tasocitinib |
| PT2675451E (pt) | 2011-02-18 | 2015-10-16 | Incyte Corp | Terapia de combinação com inibidores mtor/jak |
| EP2691395B1 (en) | 2011-03-28 | 2017-08-30 | ratiopharm GmbH | Processes for preparing tofacitinib salts |
| US9050342B2 (en) | 2011-03-29 | 2015-06-09 | Pfizer Inc. | Beneficial effects of combination therapy on cholesterol |
| CA2830463A1 (en) * | 2011-04-08 | 2012-10-11 | Pfizer Inc. | Pharmaceutical composition comprising tofacitinib and a penetration enhancer |
| ES2414384T3 (es) | 2011-05-11 | 2013-07-19 | Ratiopharm Gmbh | Composición de liberación modificada que comprende ranolazina |
| MX344479B (es) | 2011-06-20 | 2016-12-16 | Incyte Holdings Corp | Derivados de azetidinil fenil, piridil o pirazinil carboxamida como inhibidores de cinasa janus (jak). |
| CA2844507A1 (en) | 2011-08-10 | 2013-02-14 | Novartis Pharma Ag | Jak pi3k/mtor combination therapy |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
| UA111854C2 (uk) | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| US8877760B2 (en) | 2011-11-23 | 2014-11-04 | Portola Pharmaceuticals, Inc. | Substituted pyrazine-2-carboxamide kinase inhibitors |
| AU2012345732B2 (en) | 2011-11-30 | 2016-07-14 | Emory University | Antiviral JAK inhibitors useful in treating or preventing retroviral and other viral infections |
| US10821111B2 (en) | 2011-11-30 | 2020-11-03 | Emory University | Antiviral JAK inhibitors useful in treating or preventing retroviral and other viral infections |
| EP3170826A1 (en) | 2011-12-15 | 2017-05-24 | ratiopharm GmbH | Tofacitinib mono-malate salt |
| AR091079A1 (es) | 2012-05-18 | 2014-12-30 | Incyte Corp | Derivados de pirrolopirimidina y pirrolopiridina sustituida con piperidinilciclobutilo como inhibidores de jak |
| WO2014016338A1 (en) | 2012-07-25 | 2014-01-30 | Lek Pharmaceuticals D.D. | New synthetic route for the preparation of 3-amino-piperidine compounds |
| US9676756B2 (en) | 2012-10-08 | 2017-06-13 | Portola Pharmaceuticals, Inc. | Substituted pyrimidinyl kinase inhibitors |
| KR20210037012A (ko) | 2012-11-15 | 2021-04-05 | 인사이트 홀딩스 코포레이션 | 룩솔리티니브의 서방성 제형 |
| CN104955803B (zh) * | 2012-11-30 | 2017-11-28 | 斯洛文尼亚莱柯制药股份有限公司 | 通过硝基‑四氢吡啶前体制备3‑氨基‑哌啶化合物 |
| WO2014097150A1 (en) | 2012-12-17 | 2014-06-26 | Ranbaxy Laboratories Limited | Process for the preparation of tofacitinib and intermediates thereof |
| US9670160B2 (en) | 2012-12-28 | 2017-06-06 | Glenmark Pharmaceuticals Limited | Process for the preparation of tofacitinib and intermediates thereof |
| MY177476A (en) | 2013-02-22 | 2020-09-16 | Pfizer | Pyrrolo [2,3-d]pyrimidine derivatives as inhibitors of janus kinases (jak) |
| CA2903418C (en) | 2013-03-06 | 2021-03-23 | Incyte Corporation | Processes and intermediates for making a jak inhibitor |
| JP6041823B2 (ja) | 2013-03-16 | 2016-12-14 | ファイザー・インク | トファシチニブの経口持続放出剤形 |
| US20140343034A1 (en) | 2013-04-25 | 2014-11-20 | Japan Tobacco Inc. | Skin barrier function improving agent |
| WO2014174073A1 (en) | 2013-04-26 | 2014-10-30 | Sandoz Ag | Sustained release formulations of tofacitinib |
| BR122020001831A8 (pt) | 2013-08-07 | 2023-01-24 | Incyte Corp | {1-{1-[3-flúor-2-(trifluormetil)isonicotinol]piperidin-4-il}-3-[4-(7h-pirrolo[2,3-d]primidin-4-il) -1h-pirazol-1-il]azetidin-3-il}acetonitrila, seu uso, formas de dosagem de liberação sustentada e doses |
| CN104513248B (zh) * | 2013-09-30 | 2019-05-24 | 重庆医药工业研究院有限责任公司 | 一种托法替尼中间体的纯化方法 |
| CN106061973B (zh) | 2013-12-05 | 2019-07-09 | 辉瑞公司 | 吡咯并[2,3-d]嘧啶基、吡咯并[2,3-b]吡嗪基和吡咯并[2,3-d]吡啶基丙烯酰胺 |
| HUE053975T2 (hu) * | 2013-12-09 | 2021-08-30 | Unichem Lab Ltd | Továbbfejlesztett eljárás (3R,4R)-(1-benzil-4-metilpiperidin-3-il)-metilamin elõállítására |
| CA2881262A1 (en) | 2014-02-06 | 2015-08-06 | Prabhudas Bodhuri | Solid forms of tofacitinib salts |
| US9498467B2 (en) | 2014-05-30 | 2016-11-22 | Incyte Corporation | Treatment of chronic neutrophilic leukemia (CNL) and atypical chronic myeloid leukemia (aCML) by inhibitors of JAK1 |
| JP6585158B2 (ja) | 2014-08-12 | 2019-10-02 | ファイザー・インク | ヤヌスキナーゼの阻害に有用なピロロ［２，３−ｄ］ピリミジン誘導体 |
| HUE064003T2 (hu) * | 2015-01-20 | 2024-02-28 | Wuxi Fortune Pharmaceutical Co Ltd | JAK-gátló |
| US10479763B2 (en) | 2015-02-17 | 2019-11-19 | Amorepacific Corporation | Chiral resolution method of N-[4-(1-aminoethyl)-phenyl]-sulfonamide derivatives |
| CN104761556B (zh) * | 2015-03-21 | 2017-06-23 | 河北国龙制药有限公司 | 托法替布中间体杂质、托法替布杂质及其合成方法，以及托法替布的质量监控方法 |
| EP3078665A1 (en) | 2015-04-10 | 2016-10-12 | OLON S.p.A. | Efficient method for the preparation of tofacitinib citrate |
| ES2734048T3 (es) | 2015-04-29 | 2019-12-04 | Wuxi Fortune Pharmaceutical Co Ltd | Inhibidores de Janus cinasas (JAK) |
| CA2984183C (en) | 2015-05-01 | 2021-11-09 | Pfizer Inc. | Pyrrolo[2,3-d]pyrimidinyl, pyrrolo[2,3-b]pyrazinyl, pyrrolo[2,3-b]pyridinyl acrylamides and epoxides thereof |
| MX2017013797A (es) | 2015-05-29 | 2018-03-21 | Wuxi Fortune Pharmaceutical Co Ltd | Inhibidor de janus quinasa. |
| US10034882B2 (en) * | 2015-07-27 | 2018-07-31 | Unichem Laboratories Limited | Tofacitinib orally disintegrating tablets |
| KR101771219B1 (ko) * | 2015-08-21 | 2017-09-05 | 양지화학 주식회사 | 야누스 키나제 1 선택적 억제제 및 그 의약 용도 |
| US10045981B2 (en) | 2015-11-24 | 2018-08-14 | Jakpharm, Llc | Selective kinase inhibitors |
| CN105348287A (zh) * | 2015-11-30 | 2016-02-24 | 宁波立华制药有限公司 | 一种枸橼酸托法替布的新型合成工艺 |
| KR102565407B1 (ko) * | 2016-01-04 | 2023-08-10 | (주)아모레퍼시픽 | 극성 비양자성 용매를 이용한 n-[4-(1-아미노에틸)-페닐]-술폰아미드 유도체의 카이랄 분할 방법 |
| US20190083609A1 (en) | 2016-01-18 | 2019-03-21 | Helmoltz Zentrum München - Deutsches Forschungszentrum Für Gesundheit And Umwelt (Gmbh) | Tofacitinib as vaccination immune modulator |
| SG11201811470PA (en) | 2016-06-30 | 2019-01-30 | Daewoong Pharmaceutical Co Ltd | Pyrazolopyrimidine derivatives as kinase inhibitor |
| CN106831538B (zh) * | 2017-01-22 | 2019-06-25 | 苏州楚凯药业有限公司 | 托法替尼中间体的制备方法 |
| KR102398659B1 (ko) | 2017-03-17 | 2022-05-16 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 피롤로트리아진 유도체 |
| CN107602569A (zh) * | 2017-10-23 | 2018-01-19 | 上海博悦生物科技有限公司 | 一种新型吡咯并[2,3‑d]嘧啶化合物及其合成方法和用途 |
| KR102078805B1 (ko) | 2017-11-30 | 2020-02-19 | 보령제약 주식회사 | 토파시티닙을 포함하는 약제학적 조성물 |
| AR113922A1 (es) | 2017-12-08 | 2020-07-01 | Incyte Corp | Terapia de combinación de dosis baja para el tratamiento de neoplasias mieloproliferativas |
| HRP20221043T1 (hr) | 2017-12-28 | 2022-11-11 | Daewoong Pharmaceutical Co., Ltd. | Derivat oksi-fluoropiperidina kao inhibitor kinaze |
| KR102577241B1 (ko) | 2017-12-28 | 2023-09-11 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 아미노-플루오로피페리딘 유도체 |
| KR102577242B1 (ko) * | 2017-12-28 | 2023-09-11 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 아미노-메틸피페리딘 유도체 |
| CN112105608B (zh) | 2018-01-30 | 2023-07-14 | 因赛特公司 | 制备(1-(3-氟-2-(三氟甲基)异烟碱基)哌啶-4-酮)的方法 |
| WO2019152232A1 (en) * | 2018-01-31 | 2019-08-08 | Twi Pharmaceuticals, Inc. | Topical formulations comprising tofacitinib |
| US11304949B2 (en) | 2018-03-30 | 2022-04-19 | Incyte Corporation | Treatment of hidradenitis suppurativa using JAK inhibitors |
| KR102131107B1 (ko) | 2019-01-15 | 2020-07-07 | 주식회사 다산제약 | 3-아미노-피페리딘 화합물의 신규한 제조 방법 |
| EP3938370A4 (en) | 2019-03-13 | 2022-12-21 | Intas Pharmaceuticals Ltd. | METHOD FOR THE PREPARATION OF TOFACITINIB AND ITS PHARMACEUTICALLY ACCEPTABLE SALT |
| WO2020198583A1 (en) | 2019-03-27 | 2020-10-01 | Insilico Medicine Ip Limited | Bicyclic jak inhibitors and uses thereof |
| WO2020204647A1 (en) * | 2019-04-05 | 2020-10-08 | Yuhan Corporation | Processes for preparing (3r,4r)-1-benzyl-n,4-dimethylpiperidin-3-amine or a salt thereof and processes for preparing tofacitinib using the same |
| US20220378707A1 (en) | 2019-11-14 | 2022-12-01 | Pfizer Inc. | 1-(((2s,3s,4s)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl)methoxy)-7-methoxyisoquinoline-6-carboxamide combinations and oral dosage forms |
| KR20210064093A (ko) | 2019-11-25 | 2021-06-02 | 주식회사 대웅제약 | 신규한 트리아졸로피리딘 유도체 및 이를 포함하는 약학 조성물 |
| WO2021198980A1 (en) | 2020-04-04 | 2021-10-07 | Pfizer Inc. | Methods of treating coronavirus disease 2019 |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| US20240166651A1 (en) * | 2021-03-15 | 2024-05-23 | Chiesi Farmaceutici S.P.A. | Heterocyclic derivatives as janus kinase inhibitors |
| EP4180042A1 (en) | 2021-11-15 | 2023-05-17 | Sanovel Ilac Sanayi Ve Ticaret A.S. | A film coated tablet comprising micronized tofacitinib |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8403224A (nl) | 1984-10-24 | 1986-05-16 | Oce Andeno Bv | Dioxafosforinanen, de bereiding ervan en de toepassing voor het splitsen van optisch actieve verbindingen. |
| US6136595A (en) | 1993-07-29 | 2000-10-24 | St. Jude Children's Research Hospital | Jak kinases and regulations of cytokine signal transduction |
| US5389509A (en) | 1993-10-04 | 1995-02-14 | Eastman Kodak Company | Ultrathin high chloride tabular grain emulsions |
| IL112249A (en) | 1994-01-25 | 2001-11-25 | Warner Lambert Co | Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds |
| EP0682027B1 (de) | 1994-05-03 | 1997-10-15 | Novartis AG | Pyrrolopyrimidinderivate mit antiproliferativer Wirkung |
| JPH07330732A (ja) * | 1994-06-10 | 1995-12-19 | Kyorin Pharmaceut Co Ltd | 光学活性な３−アミノ−１−ベンジルピペリジン誘導体 |
| US6136596A (en) * | 1995-05-19 | 2000-10-24 | University Of Massachusetts | Cytokine-, stress-, and oncoprotein-activated human protein kinase kinases |
| DE69531558T2 (de) | 1995-06-07 | 2004-03-18 | Pfizer Inc. | Heterocyclische kondensierte pyrimidin-derivate |
| EP0836602B1 (en) | 1995-07-05 | 2002-01-30 | E.I. Du Pont De Nemours And Company | Fungicidal pyrimidinones |
| PT836605E (pt) | 1995-07-06 | 2002-07-31 | Novartis Ag | Pirrolopirimidinas e processos para a sua preparacao |
| AR004010A1 (es) | 1995-10-11 | 1998-09-30 | Glaxo Group Ltd | Compuestos heterociclicos |
| CN1168138A (zh) | 1995-11-14 | 1997-12-17 | 法玛西雅厄普约翰公司 | 芳基和杂芳基嘌呤化合物 |
| DE69712745T2 (de) | 1996-01-23 | 2002-10-31 | Novartis Ag, Basel | Pyrrolopyrimidinen und verfahren zu deren herstellung |
| CH690773A5 (de) | 1996-02-01 | 2001-01-15 | Novartis Ag | Pyrrolo(2,3-d)pyrimide und ihre Verwendung. |
| GB9604361D0 (en) | 1996-02-29 | 1996-05-01 | Pharmacia Spa | 4-Substituted pyrrolopyrimidine compounds as tyrosine kinase inhibitors |
| AU1794697A (en) | 1996-03-06 | 1997-09-22 | Novartis Ag | 7-alkyl-pyrrolo{2,3-d}pyrimidines |
| AU3176297A (en) | 1996-06-25 | 1998-01-14 | Novartis Ag | Substituted 7-amino-pyrrolo{3,2-d}pyrimidines and the use thereof |
| DE69718472T2 (de) | 1996-07-13 | 2003-11-06 | Glaxo Group Ltd., Greenford | Bicyclische heteroaromatische verbindungen als protein tyrosine kinase inhibitoren |
| HRP970371A2 (en) | 1996-07-13 | 1998-08-31 | Kathryn Jane Smith | Heterocyclic compounds |
| DK0938486T3 (da) | 1996-08-23 | 2008-07-07 | Novartis Ag | Substituerede pyrrolopyrimidiner og fremgangsmåder til deres fremstilling |
| AU4718997A (en) | 1996-11-27 | 1998-06-22 | Pfizer Inc. | Fused bicyclic pyrimidine derivatives |
| ES2301194T3 (es) | 1997-02-05 | 2008-06-16 | Warner-Lambert Company Llc | Pirido 2,3-d pirimidinas y 4-aminopirimidinas como inhibidores de la proliferacion celular. |
| US6187552B1 (en) | 1997-03-24 | 2001-02-13 | Pharmacia & Upjohn Company | Method for identifying inhibitors of JAK2/cytokine receptor binding |
| AU3378799A (en) | 1998-04-02 | 1999-10-25 | Neurogen Corporation | Aminoalkyl substituted pyrrolo(2,3-b)pyridine and pyrrolo(2,3-d)pyrimidine derivatives: modulators of crf1 receptors |
| CA2333392A1 (en) | 1998-05-28 | 1999-12-02 | Parker Hughes Institute | Quinazolines for treating brain tumor |
| RS50087B (sr) | 1998-06-19 | 2009-01-22 | Pfizer Products Inc., | Pirolo (2,3-d) pirimidin jedinjenja |
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| JP2004504259A (ja) | 1998-06-30 | 2004-02-12 | パーカー ヒューズ インスティテュート | Ｊａｋ−３インヒビターを用いたｃ−ｊｕｎ発現の阻害方法 |
| MXPA01001893A (es) | 1998-08-21 | 2002-04-24 | Parker Hughes Inst | Derivados de quinazolina. |
| US6080747A (en) | 1999-03-05 | 2000-06-27 | Hughes Institute | JAK-3 inhibitors for treating allergic disorders |
| PT1235830E (pt) * | 1999-12-10 | 2004-04-30 | Pfizer Prod Inc | Compostos de pirrolo¬2,3-d|pirimidina como inibidores das proteina cinases |
| SI1294724T1 (sl) | 2000-06-26 | 2006-08-31 | Pfizer Prod Inc | Pirolo(2,3-d)primidinske spojine kot imunosupresivna sredstva |
| GT200200234A (es) | 2001-12-06 | 2003-06-27 | Compuestos cristalinos novedosos | |
| US7358250B2 (en) * | 2004-06-29 | 2008-04-15 | Amgen Inc. | Pyrrolo[2,3-d]pyrimidines that modulate ACK1 activity |
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