CA2749837C - Derivatives of n2-(3-pyridil or phenyl)-n4-(4-piperidyl)-2,4-pyrimidinediamine useful in the treatment of inflammatory, autoimmune or proliferative diseases - Google Patents

Derivatives of n2-(3-pyridil or phenyl)-n4-(4-piperidyl)-2,4-pyrimidinediamine useful in the treatment of inflammatory, autoimmune or proliferative diseases Download PDF

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CA2749837C
CA2749837C CA2749837A CA2749837A CA2749837C CA 2749837 C CA2749837 C CA 2749837C CA 2749837 A CA2749837 A CA 2749837A CA 2749837 A CA2749837 A CA 2749837A CA 2749837 C CA2749837 C CA 2749837C
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substituted
fluoro
tetrazol
alkyl
phenyl
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French (fr)
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CA2749837A1 (en
Inventor
Rajinder Singh
Hui Li
Haoran Zhao
Rao Kolluri
Kin Tso
John Ramphal
Shihai Gu
Carlos Valdez
Jing Zhang
Emily Stauffer
Matthew Duncton
Salvador Alvarez
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Rigel Pharmaceuticals Inc
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Rigel Pharmaceuticals Inc
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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    • A61K31/5375—1,4-Oxazines, e.g. morpholine
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CA2749837A 2009-01-21 2010-01-21 Derivatives of n2-(3-pyridil or phenyl)-n4-(4-piperidyl)-2,4-pyrimidinediamine useful in the treatment of inflammatory, autoimmune or proliferative diseases Active CA2749837C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US14627309P 2009-01-21 2009-01-21
US61/146,273 2009-01-21
US26416509P 2009-11-24 2009-11-24
US61/264,165 2009-11-24
PCT/US2010/021662 WO2010090875A1 (en) 2009-01-21 2010-01-21 Derivatives of n2-(3-pyridil or phenyl)-n4-(4-piperidyl)-2,4-pyrimidinediamine useful in the treatment of inflammatory, autoimmune or proliferative diseases

Publications (2)

Publication Number Publication Date
CA2749837A1 CA2749837A1 (en) 2010-08-12
CA2749837C true CA2749837C (en) 2017-07-11

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CA2749837A Active CA2749837C (en) 2009-01-21 2010-01-21 Derivatives of n2-(3-pyridil or phenyl)-n4-(4-piperidyl)-2,4-pyrimidinediamine useful in the treatment of inflammatory, autoimmune or proliferative diseases

Country Status (6)

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US (2) US8377924B2 (https=)
EP (1) EP2389373B1 (https=)
JP (2) JP5781943B2 (https=)
CA (1) CA2749837C (https=)
ES (1) ES2635504T3 (https=)
WO (1) WO2010090875A1 (https=)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005013996A2 (en) * 2003-08-07 2005-02-17 Rigel Pharmaceuticals, Inc. 2,4-pyrimidinediamine compounds and uses as anti-proliferative agents
US20110130415A1 (en) 2009-12-01 2011-06-02 Rajinder Singh Protein kinase c inhibitors and uses thereof
EP2595982B1 (en) 2010-07-21 2018-06-13 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof
SG10201509157QA (en) * 2010-11-09 2015-12-30 Fujian Haixi Pharmaceuticals Inc Compound for increasing kinase active and application thereof
SMT202400031T1 (it) 2011-04-22 2024-03-13 Signal Pharm Llc Diamminocarbossammide e diamminocarbonitrile pirimidine sostituite, loro composizioni e metodi di trattamento con esse
ES2658395T3 (es) 2012-04-04 2018-03-09 Rigel Pharmaceuticals, Inc. Inhibidores de proteína cinasa C y usos de los mismos
EP2928891B1 (en) 2012-12-04 2019-02-20 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof
CA2904610A1 (en) 2013-03-14 2014-09-25 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof
EP3082819B1 (en) 2013-12-20 2020-06-17 Signal Pharmaceuticals, LLC Substituted diaminopyrimidyl compounds, compositions thereof, and methods of treatment therewith
NZ715903A (en) 2014-01-30 2017-06-30 Signal Pharm Llc Solid forms of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide, compositions thereof and methods of their use
MX2016012574A (es) 2014-03-28 2017-09-26 Calitor Sciences Llc Compuestos heteroarilo sustituidos y metodos de uso.
EP3206691B1 (en) 2014-10-14 2018-09-19 Sunshine Lake Pharma Co., Ltd. Substituted heteroaryl compounds and methods of use
BR112017012795A2 (pt) 2014-12-16 2018-01-02 Signal Pharmaceuticals, Llc Formulações de 2-(terc-butilamino)-4-((1r,3r,4r)-3- hidroxi-4-metilciclo-hexilamino)-pirimidina-5- carboxamida
EP3233808B1 (en) 2014-12-16 2021-07-14 Signal Pharmaceuticals, LLC Medical uses comprising methods for measurement of inhibition of c-jun n-terminal kinase in skin
WO2016123291A1 (en) 2015-01-29 2016-08-04 Signal Pharmaceuticals, Llc Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
CN108137559B (zh) * 2015-07-09 2021-11-02 默克专利有限公司 用作btk抑制剂的嘧啶衍生物及其用途
CA3208587A1 (en) 2015-07-24 2017-02-02 Celgene Corporation Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein
WO2017044434A1 (en) 2015-09-11 2017-03-16 Sunshine Lake Pharma Co., Ltd. Substituted heteroaryl compounds and methods of use
WO2017075418A1 (en) 2015-10-30 2017-05-04 Board Of Trustees Of The University Of Arkansas Inhibitors of oxidized low-density lipoprotein receptor 1 and methods of use thereof
CN110621316B (zh) 2017-04-21 2024-01-26 Epizyme股份有限公司 用ehmt2抑制剂进行的组合疗法
CN110869017B (zh) 2017-05-12 2023-05-05 英安塔制药有限公司 细胞凋亡信号调节激酶1抑制剂及其使用方法
WO2018218051A1 (en) 2017-05-25 2018-11-29 Enanta Pharmaceuticals, Inc. Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
WO2018218044A2 (en) 2017-05-25 2018-11-29 Enanta Pharmaceuticals Inc Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
US10253018B2 (en) 2017-05-25 2019-04-09 Enanta Pharmaceuticals, Inc. Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
WO2019046186A1 (en) * 2017-08-28 2019-03-07 Enanta Pharmaceuticals, Inc. INHIBITORS OF KINASE 1 REGULATING THE APOPTOTIC SIGNAL CONTAINING TETRAZOLES AND METHODS OF USE THEREOF
EP3697419A4 (en) * 2017-10-17 2021-08-18 Epizyme, Inc. AMINE SUBSTITUTION HETEROCYCLIC COMPOUNDS USED AS AND DERIVATIVES OF EHMT2
US10683297B2 (en) 2017-11-19 2020-06-16 Calitor Sciences, Llc Substituted heteroaryl compounds and methods of use
EP3787621B1 (en) 2018-05-02 2024-12-18 Enanta Pharmaceuticals, Inc. Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
WO2019213239A1 (en) 2018-05-02 2019-11-07 Enanta Pharmaceuticals Inc. Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
US10968199B2 (en) 2018-08-22 2021-04-06 Enanta Pharmaceuticals, Inc. Cycloalkyl-containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
WO2020106707A1 (en) 2018-11-19 2020-05-28 Enanta Pharmaceuticals, Inc. Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
US11466033B2 (en) 2019-03-25 2022-10-11 Enanta Pharmaceuticals, Inc. Substituted pyridines as apoptosis signal-regulating kinase 1 inhibitors
WO2022147622A1 (en) * 2021-01-07 2022-07-14 Ontario Institute For Cancer Research (Oicr) Isoindolinone aminopyrimidine compounds as inhibitors of nuak kinases, compositions and uses thereof
WO2023043630A1 (en) * 2021-09-16 2023-03-23 Lomond Therapeutics, Inc. Compounds having n-arylpyrimidin-2-amine derivatives as therapeutic agents
CN119462522A (zh) * 2023-08-08 2025-02-18 浙江大学 N2-3-氟-5-取代苯基-2-氨基嘧啶类衍生物、其制备方法及医药用途

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9523675D0 (en) 1995-11-20 1996-01-24 Celltech Therapeutics Ltd Chemical compounds
ATE407678T1 (de) * 2001-10-17 2008-09-15 Boehringer Ingelheim Pharma Pyrimidinderivate, arzneimittel enthaltend diese verbindungen, deren verwendung und verfahren zu ihrer herstellung
TWI329105B (en) 2002-02-01 2010-08-21 Rigel Pharmaceuticals Inc 2,4-pyrimidinediamine compounds and their uses
ES2445208T3 (es) 2002-07-29 2014-02-28 Rigel Pharmaceuticals, Inc. Compuestos de 2,4-pirimidindiamina para uso en métodos para tratar o prevenir enfermedades autoinmunitarias
CA2505546A1 (en) 2002-11-08 2004-05-27 Tolerrx, Inc. Molecules preferentially associated with effector t cells and methods of their use
UA80767C2 (en) * 2002-12-20 2007-10-25 Pfizer Prod Inc Pyrimidine derivatives for the treatment of abnormal cell growth
US7603542B2 (en) 2003-06-25 2009-10-13 Nec Corporation Reconfigurable electric computer, semiconductor integrated circuit and control method, program generation method, and program for creating a logic circuit from an application program
BRPI0413018B8 (pt) * 2003-07-30 2021-05-25 Rigel Pharmaceuticals Inc composto, e, uso de um composto
WO2005013996A2 (en) 2003-08-07 2005-02-17 Rigel Pharmaceuticals, Inc. 2,4-pyrimidinediamine compounds and uses as anti-proliferative agents
CN1863773A (zh) 2003-10-09 2006-11-15 埃科特莱茵药品有限公司 四氢吡啶衍生物
US20050164323A1 (en) 2003-12-24 2005-07-28 Wyeth Methods of treating asthma
JP2007532506A (ja) * 2004-04-08 2007-11-15 ノバルティス アクチエンゲゼルシャフト 自己免疫疾患および拒絶反応の処置のためのタンパク質キナーゼｃ阻害剤
EP1883302A4 (en) * 2005-05-03 2009-05-20 Rigel Pharmaceuticals Inc JAK KINASE HEMMER AND ITS USE
US20100144751A1 (en) 2007-03-28 2010-06-10 Array Biopharma Inc. IMIDAZO[1,2-a]PYRIDINE COMPOUNDS AS RECEPTOR TYROSINE KINASE INHIBITORS
CA2693594A1 (en) * 2007-07-17 2009-01-22 Rigel Pharmaceuticals, Inc. Cyclic amine substituted pyrimidinediamines as pkc inhibitors
TWI546290B (zh) * 2008-06-27 2016-08-21 賽基艾維洛米斯研究股份有限公司 雜芳基化合物及其用途
EP2595982B1 (en) * 2010-07-21 2018-06-13 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof

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US9149475B2 (en) 2015-10-06
CA2749837A1 (en) 2010-08-12
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JP2015110629A (ja) 2015-06-18
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JP2012515724A (ja) 2012-07-12
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