CN101460499A - 可用作janus激酶抑制剂的去氮杂嘌呤 - Google Patents
可用作janus激酶抑制剂的去氮杂嘌呤 Download PDFInfo
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Landscapes
- Health & Medical Sciences (AREA)
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| US78944106P | 2006-04-05 | 2006-04-05 | |
| US60/789,441 | 2006-04-05 |
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| CN101460499A true CN101460499A (zh) | 2009-06-17 |
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| US (4) | US8741912B2 (https=) |
| EP (1) | EP2001884A1 (https=) |
| JP (2) | JP2009532475A (https=) |
| KR (1) | KR20090018895A (https=) |
| CN (1) | CN101460499A (https=) |
| AU (1) | AU2007235487A1 (https=) |
| CA (1) | CA2648250A1 (https=) |
| IL (1) | IL194460A0 (https=) |
| MX (1) | MX2008012860A (https=) |
| NO (1) | NO20084652L (https=) |
| RU (1) | RU2008143361A (https=) |
| SG (1) | SG170828A1 (https=) |
| WO (1) | WO2007117494A1 (https=) |
| ZA (1) | ZA200808536B (https=) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102482284A (zh) * | 2009-07-02 | 2012-05-30 | 健泰科生物技术公司 | 作为jak抑制剂的吡唑并嘧啶化合物和方法 |
| CN102985417A (zh) * | 2010-03-10 | 2013-03-20 | 因塞特公司 | 作为jak1抑制剂的哌啶-4-基氮杂环丁烷衍生物 |
| CN103298817A (zh) * | 2011-01-07 | 2013-09-11 | 利奥制药有限公司 | 作为蛋白酪氨酸激酶抑制剂的新磺酰胺哌嗪衍生物及其药物用途 |
| CN108586341A (zh) * | 2018-05-25 | 2018-09-28 | 天津商业大学 | 酰胺类化合物和其药用盐及其制备方法和药物用途 |
| WO2021254133A1 (zh) * | 2020-06-15 | 2021-12-23 | 嘉兴特科罗生物科技有限公司 | 一种小分子化合物 |
| CN116478172A (zh) * | 2023-06-20 | 2023-07-25 | 英矽智能科技(上海)有限公司 | 吡咯并[3,2-d]嘧啶类化合物及其应用 |
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| ES2364340T3 (es) | 2004-03-30 | 2011-08-31 | Vertex Pharmaceuticals Incorporated | Azaindoles útiles como inhibidores de jak y otras proteína quinasas. |
| EP2354140A1 (en) * | 2005-05-20 | 2011-08-10 | Vertex Pharmaceuticals Incorporated | Pyrrolopyridines useful as inhibitors of protein kinase |
| CA2621261C (en) | 2005-09-22 | 2014-05-20 | Incyte Corporation | Azepine inhibitors of janus kinases |
| SG10202003901UA (en) | 2005-12-13 | 2020-05-28 | Incyte Holdings Corp | Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as janus kinase inhibitors |
| UA95940C2 (uk) | 2006-01-17 | 2011-09-26 | Вертекс Фармасьютикалс Інкорпорейтед | Азаіндоли як інгібітори кіназ януса |
| SG170828A1 (en) | 2006-04-05 | 2011-05-30 | Vertex Pharmaceuticals Inc Us | Deazapurines useful as inhibitors of janus kinases |
| CN101678022A (zh) | 2006-12-21 | 2010-03-24 | 弗特克斯药品有限公司 | 可用作蛋白激酶抑制剂的5-氰基-4-(吡咯并[2,3b]吡啶-3-基)嘧啶衍生物 |
| CA2673038C (en) | 2006-12-22 | 2015-12-15 | Incyte Corporation | Substituted tricyclic heteroaryl compounds as janus kinase inhibitors |
| KR20150036210A (ko) | 2007-06-13 | 2015-04-07 | 인사이트 코포레이션 | 야누스 키나제 억제제（Ｒ）―３―（４―（７Ｈ―피롤로［２，３－ｄ］피리미딘―4―일）―1Ｈ―피라졸―1―일）―３―사이클로펜틸프로판니트릴의 염 |
| 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. |
| JP2011513483A (ja) * | 2008-03-10 | 2011-04-28 | 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 | タンパク質キナーゼの阻害剤として有用なピリミジンおよびピリジン |
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| AR076794A1 (es) * | 2009-05-22 | 2011-07-06 | Incyte Corp | Derivados de n-(hetero)aril-pirrolidina de pirazol-4-il-pirrolo [2,3-d]pirimidinas y pirrol-3-il-pirrolo [2,3-d ]pirimidinas como inhibidores de la quinasa janus y composiciones farmaceuticas que los contienen |
| ES2540964T3 (es) * | 2009-06-08 | 2015-07-15 | Takeda Pharmaceutical Company Limited | Compuestos de dihidropirrolonaftiridinona como inhibidores de JAK |
| LT3141252T (lt) | 2009-06-17 | 2018-11-12 | Vertex Pharmaceuticals Inc. | Gripo virusų replikacijos inhibitoriai |
| WO2011003418A1 (en) | 2009-07-08 | 2011-01-13 | Leo Pharma A/S | Heterocyclic compounds as jak receptor and protein tyrosine kinase inhibitors |
| TW201113285A (en) * | 2009-09-01 | 2011-04-16 | Incyte Corp | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
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| AU2010339444A1 (en) | 2009-12-30 | 2012-07-19 | Arqule, Inc. | Substituted pyrrolo-aminopyrimidine compounds |
| JP5858434B2 (ja) * | 2010-02-18 | 2016-02-10 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｊａｎｕｓキナーゼ阻害薬としてのシクロブタンおよびメチルシクロブタン誘導体 |
| AU2015205858B2 (en) * | 2010-03-10 | 2017-04-13 | Incyte Holdings Corporation | Piperidin-4-yl azetidine derivatives as jak1 inhibitors |
| PE20130216A1 (es) | 2010-05-21 | 2013-02-27 | Incyte Corp | Formulacion topica para un inhibidor de jak |
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| WO2012078802A1 (en) * | 2010-12-08 | 2012-06-14 | Takeda Pharmaceutical Company Limited | PREPARATION OF SUBSTITUTED-4,5-DIHYDROPYRROLO[4,3,2-de][2,6]NAPHTHYRIDIN-3(1H)-ONES |
| RU2013132681A (ru) | 2010-12-16 | 2015-01-27 | Вертекс Фармасьютикалз Инкорпорейтед | Ингибиторы репликации вирусов гриппа |
| ES2547916T3 (es) | 2011-02-18 | 2015-10-09 | Novartis Pharma Ag | Terapia de combinación de inhibidores de mTOR/JAK |
| CN103547580B (zh) | 2011-03-22 | 2016-12-07 | 阿迪维纳斯疗法有限公司 | 取代的稠合三环化合物、其组合物及医药用途 |
| CN103502249A (zh) * | 2011-05-17 | 2014-01-08 | 普林斯匹亚生物制药公司 | 作为酪氨酸激酶抑制剂的氮杂吲哚衍生物 |
| CN103797010B (zh) | 2011-06-20 | 2016-02-24 | 因塞特控股公司 | 作为jak抑制剂的氮杂环丁烷基苯基、吡啶基或吡嗪基甲酰胺衍生物 |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| EP2741747A1 (en) | 2011-08-10 | 2014-06-18 | Novartis Pharma AG | JAK P13K/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 |
| TW201406761A (zh) | 2012-05-18 | 2014-02-16 | Incyte Corp | 做爲ｊａｋ抑制劑之哌啶基環丁基取代之吡咯并吡啶及吡咯并嘧啶衍生物 |
| WO2014013014A1 (en) | 2012-07-18 | 2014-01-23 | Fundació Privada Centre De Regulació Genòmica (Crg) | Jak inhibitors for activation of epidermal stem cell populations |
| US9593115B2 (en) | 2012-09-21 | 2017-03-14 | Advinus Therapeutics Ltd. | Substituted fused tricyclic compounds, compositions, and medicinal applications thereof |
| PH12020551186B1 (en) | 2012-11-15 | 2024-03-20 | Incyte Holdings Corp | Sustained-release dosage forms of ruxolitinib |
| RS62867B1 (sr) | 2013-03-06 | 2022-02-28 | Incyte Holdings Corp | Postupci i intermedijeri za dobijanje inhibitora jak |
| SMT202000315T1 (it) * | 2013-08-07 | 2020-07-08 | Incyte Corp | Forme di dosaggio a rilascio prolungato per un inibitore di jak1 |
| LT3068776T (lt) | 2013-11-13 | 2019-08-12 | Vertex Pharmaceuticals Incorporated | Gripo virusų replikacijos inhibitoriai |
| JP6618901B2 (ja) | 2013-11-13 | 2019-12-11 | 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Ｖｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤を調製する方法 |
| 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 |
| CN105777754B (zh) | 2014-12-16 | 2019-07-26 | 北京赛林泰医药技术有限公司 | 吡咯并嘧啶化合物 |
| EP3294735B8 (en) | 2015-05-13 | 2022-01-05 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| EP3294717B1 (en) | 2015-05-13 | 2020-07-29 | Vertex Pharmaceuticals Inc. | Methods of preparing inhibitors of influenza viruses replication |
| KR102598246B1 (ko) * | 2016-07-26 | 2023-11-02 | 톈진 롱보진 파마시우티컬 씨오., 엘티디. | Jak 저해제로서 헤테로사이클릭 화합물, 및 이의 염 및 치료학적 용도 |
| WO2018041989A1 (en) | 2016-09-02 | 2018-03-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for diagnosing and treating refractory celiac disease type 2 |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| SG11202007164UA (en) | 2018-01-30 | 2020-08-28 | Incyte Corp | Processes for preparing (1 -(3-fluoro-2-(trifluoromethyl)isonicotinyl)piperidine-4-one) |
| SMT202400306T1 (it) | 2018-03-30 | 2024-09-16 | Incyte Corp | Trattamento dell'idrosadenite suppurativa utilizzando inibitori di jak. |
| EA202192575A1 (ru) | 2019-03-21 | 2022-01-14 | Онксео | Соединения dbait в сочетании с ингибиторами киназ для лечения рака |
| EP3947737A2 (en) | 2019-04-02 | 2022-02-09 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods of predicting and preventing cancer in patients having premalignant lesions |
| EP3955920A1 (en) | 2019-04-16 | 2022-02-23 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Use of jak inhibitors for the treatment of painful conditions involving nav1.7 channels |
| EP3725305A1 (en) | 2019-04-17 | 2020-10-21 | Zentiva K.S. | Pharmaceutical composition containing baricitinib hydrobromide |
| US20220372135A1 (en) | 2019-09-27 | 2022-11-24 | Disc Medicine, Inc. | Methods for treating myelofibrosis and related conditions |
| CN114761006A (zh) | 2019-11-08 | 2022-07-15 | Inserm(法国国家健康医学研究院) | 对激酶抑制剂产生耐药性的癌症的治疗方法 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| KR20230012539A (ko) | 2020-05-13 | 2023-01-26 | 디스크 메디슨, 인크. | 골수섬유증을 치료하기 위한 항-헤모주벨린 (hjv) 항체 |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| CN112979634A (zh) * | 2021-02-06 | 2021-06-18 | 绍兴文理学院 | 一种含酰胺结构的噻唑类化合物及其制备方法和应用 |
| CN112979635A (zh) * | 2021-02-06 | 2021-06-18 | 绍兴文理学院 | 一种噻唑类化合物及其制备方法和应用 |
| WO2023222565A1 (en) | 2022-05-16 | 2023-11-23 | Institut National de la Santé et de la Recherche Médicale | Methods for assessing the exhaustion of hematopoietic stems cells induced by chronic inflammation |
Family Cites Families (18)
| 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 |
| DE60037345T2 (de) | 1999-12-10 | 2008-11-13 | Pfizer Products Inc., Groton | Pyrrolo(2,3-d)pyrimidin-Verbindungen |
| CO5271715A1 (es) * | 1999-12-21 | 2003-04-30 | Sugen Inc | 7-aza-indolin-2-onas sustituidas en 4 y su uso como inhibidores de proteiuna quinasa |
| WO2003053336A2 (en) * | 2001-12-19 | 2003-07-03 | The Quigley Corporation | Methods for the treatment of peripheral neural and vascular ailments |
| JP2006518381A (ja) * | 2003-02-07 | 2006-08-10 | 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 | プロテインキナーゼのインヒビターとして有用なヘテロアリール置換ピロール |
| TWI339206B (en) * | 2003-09-04 | 2011-03-21 | Vertex Pharma | Compositions useful as inhibitors of protein kinases |
| CA2547080A1 (en) * | 2003-12-02 | 2005-07-28 | Vertex Pharmaceuticals, Inc. | Heterocyclic protein kinase inhibitors and uses thereof |
| ES2364340T3 (es) * | 2004-03-30 | 2011-08-31 | Vertex Pharmaceuticals Incorporated | Azaindoles útiles como inhibidores de jak y otras proteína quinasas. |
| AR049333A1 (es) * | 2004-04-02 | 2006-07-19 | Vertex Pharma | Azaindoles inhibidores de proteinquinasas rock y otras proteinas quinasas. composiciones farmaceuticas. |
| WO2005117909A2 (en) | 2004-04-23 | 2005-12-15 | Exelixis, Inc. | Kinase modulators and methods of use |
| US20060122213A1 (en) * | 2004-06-30 | 2006-06-08 | Francoise Pierard | Azaindoles useful as inhibitors of protein kinases |
| KR20070104641A (ko) * | 2005-02-03 | 2007-10-26 | 버텍스 파마슈티칼스 인코포레이티드 | 단백질 키나제의 억제제로 유용한 피롤로피리미딘 |
| US20080188483A1 (en) * | 2005-03-15 | 2008-08-07 | Irm Llc | Compounds and Compositions as Protein Kinase Inhibitors |
| EP2354140A1 (en) * | 2005-05-20 | 2011-08-10 | Vertex Pharmaceuticals Incorporated | Pyrrolopyridines useful as inhibitors of protein kinase |
| ZA200802685B (en) * | 2005-09-30 | 2009-10-28 | Vertex Pharma | Deazapurines useful as inhibitors of janus kinases |
| SG10202003901UA (en) * | 2005-12-13 | 2020-05-28 | Incyte Holdings Corp | Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as janus kinase inhibitors |
| UA95940C2 (uk) * | 2006-01-17 | 2011-09-26 | Вертекс Фармасьютикалс Інкорпорейтед | Азаіндоли як інгібітори кіназ януса |
| SG170828A1 (en) | 2006-04-05 | 2011-05-30 | Vertex Pharmaceuticals Inc Us | Deazapurines useful as inhibitors of janus kinases |
-
2007
- 2007-04-05 SG SG201102383-5A patent/SG170828A1/en unknown
- 2007-04-05 CN CNA200780020405XA patent/CN101460499A/zh active Pending
- 2007-04-05 AU AU2007235487A patent/AU2007235487A1/en not_active Abandoned
- 2007-04-05 WO PCT/US2007/008367 patent/WO2007117494A1/en not_active Ceased
- 2007-04-05 CA CA002648250A patent/CA2648250A1/en not_active Abandoned
- 2007-04-05 US US11/732,845 patent/US8741912B2/en not_active Expired - Fee Related
- 2007-04-05 KR KR1020087027078A patent/KR20090018895A/ko not_active Ceased
- 2007-04-05 JP JP2009504273A patent/JP2009532475A/ja active Pending
- 2007-04-05 RU RU2008143361/04A patent/RU2008143361A/ru not_active Application Discontinuation
- 2007-04-05 MX MX2008012860A patent/MX2008012860A/es not_active Application Discontinuation
- 2007-04-05 EP EP07754825A patent/EP2001884A1/en not_active Withdrawn
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2008
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- 2008-10-03 US US12/245,069 patent/US20090227607A1/en not_active Abandoned
- 2008-10-07 ZA ZA2008/08536A patent/ZA200808536B/en unknown
- 2008-11-05 NO NO20084652A patent/NO20084652L/no not_active Application Discontinuation
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2012
- 2012-02-23 US US13/403,169 patent/US20120316186A1/en not_active Abandoned
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2013
- 2013-11-01 JP JP2013228595A patent/JP2014024869A/ja not_active Ceased
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- 2014-04-11 US US14/250,668 patent/US20140315931A1/en not_active Abandoned
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102482284A (zh) * | 2009-07-02 | 2012-05-30 | 健泰科生物技术公司 | 作为jak抑制剂的吡唑并嘧啶化合物和方法 |
| CN104910161A (zh) * | 2009-07-02 | 2015-09-16 | 健泰科生物技术公司 | 作为jak抑制剂的吡唑并嘧啶化合物和方法 |
| CN102482284B (zh) * | 2009-07-02 | 2015-11-25 | 健泰科生物技术公司 | 作为jak抑制剂的吡唑并嘧啶化合物和方法 |
| CN104910161B (zh) * | 2009-07-02 | 2018-03-30 | 健泰科生物技术公司 | 作为jak抑制剂的吡唑并嘧啶化合物和方法 |
| CN102985417A (zh) * | 2010-03-10 | 2013-03-20 | 因塞特公司 | 作为jak1抑制剂的哌啶-4-基氮杂环丁烷衍生物 |
| CN102985417B (zh) * | 2010-03-10 | 2015-01-28 | 因塞特公司 | 作为jak1抑制剂的哌啶-4-基氮杂环丁烷衍生物 |
| CN103298817A (zh) * | 2011-01-07 | 2013-09-11 | 利奥制药有限公司 | 作为蛋白酪氨酸激酶抑制剂的新磺酰胺哌嗪衍生物及其药物用途 |
| CN108586341A (zh) * | 2018-05-25 | 2018-09-28 | 天津商业大学 | 酰胺类化合物和其药用盐及其制备方法和药物用途 |
| CN108586341B (zh) * | 2018-05-25 | 2020-05-08 | 天津商业大学 | 酰胺类化合物和其药用盐及其制备方法和药物用途 |
| WO2021254133A1 (zh) * | 2020-06-15 | 2021-12-23 | 嘉兴特科罗生物科技有限公司 | 一种小分子化合物 |
| CN116478172A (zh) * | 2023-06-20 | 2023-07-25 | 英矽智能科技(上海)有限公司 | 吡咯并[3,2-d]嘧啶类化合物及其应用 |
| CN116478172B (zh) * | 2023-06-20 | 2023-09-05 | 英矽智能科技(上海)有限公司 | 吡咯并[3,2-d]嘧啶类化合物及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| NO20084652L (no) | 2008-12-03 |
| US20090227607A1 (en) | 2009-09-10 |
| CA2648250A1 (en) | 2007-10-18 |
| US20120316186A1 (en) | 2012-12-13 |
| JP2009532475A (ja) | 2009-09-10 |
| KR20090018895A (ko) | 2009-02-24 |
| WO2007117494A1 (en) | 2007-10-18 |
| IL194460A0 (en) | 2009-08-03 |
| US8741912B2 (en) | 2014-06-03 |
| JP2014024869A (ja) | 2014-02-06 |
| AU2007235487A1 (en) | 2007-10-18 |
| MX2008012860A (es) | 2009-01-07 |
| US20090088445A1 (en) | 2009-04-02 |
| EP2001884A1 (en) | 2008-12-17 |
| SG170828A1 (en) | 2011-05-30 |
| US20140315931A1 (en) | 2014-10-23 |
| ZA200808536B (en) | 2012-07-25 |
| RU2008143361A (ru) | 2010-05-10 |
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