CN101511783A - 用于治疗淋巴细胞相互作用介导的疾病的n-联芳(杂)芳基磺酰胺衍生物 - Google Patents

用于治疗淋巴细胞相互作用介导的疾病的n-联芳(杂)芳基磺酰胺衍生物 Download PDF

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CN101511783A
CN101511783A CNA2007800331430A CN200780033143A CN101511783A CN 101511783 A CN101511783 A CN 101511783A CN A2007800331430 A CNA2007800331430 A CN A2007800331430A CN 200780033143 A CN200780033143 A CN 200780033143A CN 101511783 A CN101511783 A CN 101511783A
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dimethyl
amino
biphenyl
chloro
benzenesulfonylamino
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Chinese (zh)
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F·贝尔斯特
P·格罗舍
P·扬泽
F·泽克里
B·博尔巴克
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Novartis AG
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Novartis AG
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102548976A (zh) * 2009-08-31 2012-07-04 雅培卫生保健产品有限责任公司 作为s1p调节剂的(硫)吗啉衍生物
US9662337B2 (en) 2010-07-09 2017-05-30 Abbvie B.V. Bisaryl (thio)morpholine derivatives as S1P modulators
US9670220B2 (en) 2010-07-09 2017-06-06 Abbvie B.V. Fused heterocyclic derivatives as S1P modulators
US9951084B2 (en) 2010-07-09 2018-04-24 Abb Vie B.V. Spiro-cyclic amine derivatives as S1P modulators
CN114394946A (zh) * 2022-02-21 2022-04-26 艾美科健（中国）生物医药有限公司 一种氟雷拉纳的合成方法
US11535632B2 (en) 2019-10-31 2022-12-27 ESCAPE Bio, Inc. Solid forms of an S1P-receptor modulator

Families Citing this family (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT2474545T (pt) 2005-12-13 2017-02-14 Incyte Holdings Corp Pirrolo[2,3-b]piridinas e pirrolo[2,3-b]pirimidinas substituídas com heteroarilo como inibidores de janus quinase
GEP20125533B (en) 2007-06-13 2012-05-25 Incyte Corp Salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentyl propanenitrile
JP5557832B2 (ja) * 2008-03-18 2014-07-23 メルク・シャープ・アンド・ドーム・コーポレーション 置換４−ヒドロキシピリジン−５−カルボキサミド
KR20220084423A (ko) 2008-07-23 2022-06-21 아레나 파마슈티칼스, 인크. 자가면역성 및 염증성의 장애의 치료에 유용한 치환된 1,2,3,4-테트라히드로시클로펜타[ｂ]인돌-3-일)아세트산 유도체
BRPI0917923B1 (pt) 2008-08-27 2022-04-05 Arena Pharmaceuticals Inc Derivado de ácido tricíclico substituído, sua composição, seu uso e processo para preparar a referida composição
UY32349A (es) * 2008-12-23 2010-07-30 Novartis Ag Derivados de biaril-bencil-amina
WO2010085968A1 (en) * 2008-12-30 2010-08-05 European Molecular Biology Laboratory (Embl) Toluidine sulfonamides and their use as hif-inhibitors
HRP20140371T1 (hr) 2009-05-15 2014-05-23 Novartis Ag Arilpiridini kao inhibitori sinteze aldosterona
HRP20192203T1 (hr) 2009-05-22 2020-03-06 Incyte Holdings Corporation 3-[4-(7h-pirolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il]oktan- ili heptan-nitril kao jak inhibitori
WO2010135650A1 (en) 2009-05-22 2010-11-25 Incyte Corporation N-(HETERO)ARYL-PYRROLIDINE DERIVATIVES OF PYRAZOL-4-YL-PYRROLO[2,3-d]PYRIMIDINES AND PYRROL-3-YL-PYRROLO[2,3-d]PYRIMIDINES AS JANUS KINASE INHIBITORS
US8399451B2 (en) 2009-08-07 2013-03-19 Bristol-Myers Squibb Company Heterocyclic compounds
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
AU2010331250B2 (en) * 2009-12-16 2015-07-30 Pola Chemical Industries Inc. Preventing or ameliorating agent for pigmentation
JP5856980B2 (ja) 2010-01-27 2016-02-10 アリーナ ファーマシューティカルズ， インコーポレイテッド （Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸およびその塩の調製のためのプロセス
CA2789480A1 (en) 2010-03-03 2011-09-09 Arena Pharmaceuticals, Inc. Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof
PE20130038A1 (es) 2010-03-10 2013-01-28 Incyte Corp Derivados de piperidin-4-il azetidina como inhibidores de jak1
US8835470B2 (en) 2010-04-23 2014-09-16 Bristol-Myers Squibb Company Mandelamide heterocyclic compounds
RS54824B1 (sr) 2010-05-21 2016-10-31 Incyte Holdings Corp Topikalna formulacija za inhibiciju jak-a
EP2619190B1 (en) 2010-09-24 2015-08-12 Bristol-Myers Squibb Company Substituted oxadiazole compounds and their use as s1p1 agonists
WO2012068440A1 (en) 2010-11-19 2012-05-24 Incyte Corporation Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as jak inhibitors
KR20140019300A (ko) 2010-11-19 2014-02-14 인사이트 코포레이션 Ｊａｋ 억제제로서 사이클로부틸 치환된 피롤로피리딘 및 피롤로피리미딘 유도체
TWI477287B (zh) * 2010-12-21 2015-03-21 Pola Chem Ind Inc 絲胺酸衍生物及製造色素沉澱之預防或改善劑之用途
EA201490042A1 (ru) 2011-06-20 2014-10-30 Инсайт Корпорейшн Азетидинил-фенил-, пиридил- или пиразинилкарбоксамидные производные как ингибиторы jak
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
WO2013126608A1 (en) 2012-02-22 2013-08-29 Sanford-Burnham Medical Research Institute Sulfonamide compounds and uses as tnap inhibitors
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
TWI761825B (zh) 2012-11-15 2022-04-21 美商英塞特控股公司 盧梭利替尼之緩釋性劑型
WO2014085453A2 (en) * 2012-11-29 2014-06-05 The Scripps Research Institute Small molecule lxr inverse agonists
BR122021015061B1 (pt) 2013-03-06 2022-10-18 Incyte Holdings Corporation Processos e intermediários para preparar um inibidor de jak
WO2015021153A1 (en) 2013-08-07 2015-02-12 Incyte Corporation Sustained release dosage forms for a jak1 inhibitor
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
EP4445956A3 (en) 2015-01-06 2024-12-04 Arena Pharmaceuticals, Inc. Compound for use in treating conditions related to the s1p1 receptor
EP3310760B8 (en) 2015-06-22 2022-10-19 Arena Pharmaceuticals, Inc. Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid for use in s1p1 receptor-associated disorders
US12084472B2 (en) 2015-12-18 2024-09-10 Ardelyx, Inc. Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists
TW202246215A (zh) 2015-12-18 2022-12-01 美商亞德利克斯公司 作為非全身ｔｇｒ５促效劑之經取代之４－苯基吡啶化合物
SG11201810837QA (en) 2016-06-29 2018-12-28 Univ Montreal Biarylmethyl heterocycles
TW201811766A (zh) 2016-08-29 2018-04-01 瑞士商諾華公司 N-(吡啶-2-基)吡啶-磺醯胺衍生物及其用於疾病治療之用途
EP3582772A1 (en) 2017-02-16 2019-12-25 Arena Pharmaceuticals, Inc. Compounds and methods for treatment of primary biliary cholangitis
CA3053416A1 (en) 2017-02-16 2018-08-23 Arena Pharmaceuticals, Inc. Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations
AR113922A1 (es) 2017-12-08 2020-07-01 Incyte Corp Terapia de combinación de dosis baja para el tratamiento de neoplasias mieloproliferativas
WO2019152374A1 (en) 2018-01-30 2019-08-08 Incyte Corporation Processes for preparing (1 -(3-fluoro-2-(trifluoromethyl)isonicotinyl)piperidine-4-one)
PL3773593T3 (pl) 2018-03-30 2024-09-02 Incyte Corporation Leczenie ropnego zapalenia gruczołów potowych z zastosowaniem inhibitorów jak
KR102859841B1 (ko) 2018-06-06 2025-09-12 아레나 파마슈티칼스, 인크. S1p1 수용체와 관련된 병태의 치료 방법
KR102836433B1 (ko) 2018-09-06 2025-07-21 아레나 파마슈티칼스, 인크. 자가면역 및 염증성 장애의 치료에 유용한 화합물
US11833155B2 (en) 2020-06-03 2023-12-05 Incyte Corporation Combination therapy for treatment of myeloproliferative neoplasms

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4315014A (en) * 1980-09-24 1982-02-09 Warner-Lambert Company Antibacterial amide compounds and pharmaceutical composition containing the same
CA2473505A1 (en) * 2002-02-07 2003-08-14 Ellen M. Leahy Novel bicyclic hydroxamates as inhibitors of histone deacetylase
WO2004024673A1 (en) * 2002-09-13 2004-03-25 Novartis Ag Amino-propanol derivatives
US20050019746A1 (en) * 2003-01-23 2005-01-27 Eirx Therapeutics Limited Apoptosis-related kinase/GPCRs
JP2007525406A (ja) * 2003-12-04 2007-09-06 ワイス ビアリールスルホンアミドおよびその使用方法
ES2348332T3 (es) * 2005-09-16 2010-12-02 Arrow Therapeutics Limited Derivados de bifenilo y su uso en el tratamiento de la hepatitis c.

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CN102548976A (zh) * 2009-08-31 2012-07-04 雅培卫生保健产品有限责任公司 作为s1p调节剂的(硫)吗啉衍生物
US9045441B2 (en) 2009-08-31 2015-06-02 Abbvie Bahamas Limited (Thio)morpholine derivatives as S1P modulators
CN102548976B (zh) * 2009-08-31 2015-09-09 雅博维巴哈马有限公司 作为s1p调节剂的(硫)吗啉衍生物
US9273017B2 (en) 2009-08-31 2016-03-01 Abbvie Bahamas Limited (Thio)morpholine derivatives as S1P modulators
US9662337B2 (en) 2010-07-09 2017-05-30 Abbvie B.V. Bisaryl (thio)morpholine derivatives as S1P modulators
US9670220B2 (en) 2010-07-09 2017-06-06 Abbvie B.V. Fused heterocyclic derivatives as S1P modulators
US9951084B2 (en) 2010-07-09 2018-04-24 Abb Vie B.V. Spiro-cyclic amine derivatives as S1P modulators
US10179791B2 (en) 2010-07-09 2019-01-15 Abbvie B.V. Spiro-cyclic amine derivatives as S1P modulators
US10807991B2 (en) 2010-07-09 2020-10-20 Abbvie B.V. Spiro-cyclic amine derivatives as S1P modulators
US11427598B2 (en) 2010-07-09 2022-08-30 AbbVie Deutschland GmbH & Co. KG Spiro-cyclic amine derivatives as S1P modulators
US11535632B2 (en) 2019-10-31 2022-12-27 ESCAPE Bio, Inc. Solid forms of an S1P-receptor modulator
CN114394946A (zh) * 2022-02-21 2022-04-26 艾美科健（中国）生物医药有限公司 一种氟雷拉纳的合成方法

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