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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    • A—HUMAN NECESSITIES
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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

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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 (enExample)
EP (1) EP2389373B1 (enExample)
JP (2) JP5781943B2 (enExample)
CA (1) CA2749837C (enExample)
ES (1) ES2635504T3 (enExample)
WO (1) WO2010090875A1 (enExample)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK1663242T3 (da) * 2003-08-07 2011-08-01 Rigel Pharmaceuticals Inc 2,4-Pyrimidindiamin-forbindelser og anvendelse som antiproliferative midler
US20110130415A1 (en) * 2009-12-01 2011-06-02 Rajinder Singh Protein kinase c inhibitors and uses thereof
CA2801781C (en) * 2010-07-21 2018-02-27 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof
EP2638036B1 (en) * 2010-11-09 2017-08-16 Betta Pharmaceuticals Co., Ltd. Compound for increasing kinase active and application thereof
TWI548621B (zh) * 2011-04-22 2016-09-11 標誌製藥公司 經取代之二胺基甲醯胺及二胺基甲腈嘧啶、其組合物、及以該等治療之方法
US9321763B2 (en) 2012-04-04 2016-04-26 Rigel Pharmaceuticals, Inc. Protein kinase C inhibitors and uses thereof
EP2928891B1 (en) 2012-12-04 2019-02-20 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof
US9169249B2 (en) 2013-03-14 2015-10-27 Rigel Pharmaceuticals, Inc. Protein kinase C inhibitors and uses thereof
RU2016129380A (ru) 2013-12-20 2018-01-25 СИГНАЛ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи Замещенные диаминопиримидильные соединения, их композиции и способы лечения с их участием
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
US9399637B2 (en) 2014-03-28 2016-07-26 Calitor Sciences, Llc Substituted heteroaryl compounds and methods of use
US10059689B2 (en) 2014-10-14 2018-08-28 Calitor Sciences, Llc Substituted heteroaryl compounds and methods of use
US9513297B2 (en) 2014-12-16 2016-12-06 Signal Pharmaceuticals, Llc Methods for measurement of inhibition of c-Jun N-terminal kinase in skin
EP3712134B1 (en) 2014-12-16 2023-11-29 Signal Pharmaceuticals, LLC Salts of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methycyclohexylamino)-pyrimidine-5-carboxamide
EP3250557B1 (en) 2015-01-29 2024-11-20 Signal Pharmaceuticals, LLC Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
JP6853234B2 (ja) * 2015-07-09 2021-03-31 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ Ｂｔｋ阻害剤としてのピリミジン誘導体及びその使用
EP3325432B1 (en) 2015-07-24 2020-09-02 Celgene Corporation Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein
EP3347097B1 (en) 2015-09-11 2021-02-24 Sunshine Lake Pharma Co., Ltd. Substituted aminopyrimidine derivatives as modulators of the kinases jak, flt3 and aurora
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
WO2018195450A1 (en) 2017-04-21 2018-10-25 Epizyme, Inc. Combination therapies with ehmt2 inhibitors
PL3621615T3 (pl) 2017-05-12 2024-03-25 Enanta Pharmaceuticals, Inc. Inhibitory regulujące sygnał apoptozy kinazy 1 i sposoby ich stosowania
WO2018218044A2 (en) 2017-05-25 2018-11-29 Enanta Pharmaceuticals Inc Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
US10450301B2 (en) 2017-05-25 2019-10-22 Enanta Pharmaceuticals, Inc. Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
WO2018218042A1 (en) 2017-05-25 2018-11-29 Enanta Pharmaceuticals, Inc. Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
US10597382B2 (en) 2017-08-28 2020-03-24 Enanta Pharmaceuticals, Inc. Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
JP7425724B2 (ja) * 2017-10-17 2024-01-31 エピザイム，インコーポレイティド Ｅｈｍｔ２阻害剤としてのアミン置換複素環化合物及びその誘導体
WO2019099311A1 (en) 2017-11-19 2019-05-23 Sunshine Lake Pharma Co., Ltd. Substituted heteroaryl compounds and methods of use
WO2019213239A1 (en) 2018-05-02 2019-11-07 Enanta Pharmaceuticals Inc. Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
IL278368B2 (en) 2018-05-02 2024-06-01 Enanta Pharm Inc Tetrazole containing 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
WO2020198214A1 (en) 2019-03-25 2020-10-01 Enanta Pharmaceuticals, Inc. Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
US12643886B2 (en) 2021-01-07 2026-06-02 Ontario Institute for Cancer Research (OICR), The Governing Council of the University of Toronto, Sinai Health System Isoindolinone aminopyrimidine compounds as inhibitors of NUAK kinases, compositions and uses thereof
EP4401735A4 (en) * 2021-09-16 2025-07-16 Lomond Therapeutics Inc COMPOUNDS COMPRISING 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
WO2026108771A2 (en) * 2024-11-19 2026-05-28 Groovy Medicine (Hangzhou) Ltd. Substituted heteroaromatic compounds as inhibitors of checkpoint kinase 1 and notch signaling pathway and uses thereof

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
JP4460292B2 (ja) * 2001-10-17 2010-05-12 ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト ピリミジン誘導体、これらの化合物を含む医薬組成物、その使用及びその調製方法
TWI329105B (en) 2002-02-01 2010-08-21 Rigel Pharmaceuticals Inc 2,4-pyrimidinediamine compounds and their uses
IL166241A0 (en) 2002-07-29 2006-01-15 Rigel Pharmaceuticals Inc Method of treating or preventing autoimmune diseases with 2,4-pyrimidinedinediamine compounds
WO2004043386A2 (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
JP4665760B2 (ja) 2003-06-25 2011-04-06 日本電気株式会社 電子計算機、半導体集積回路、制御方法、プログラムの生成方法、及びプログラム
ES2421139T3 (es) 2003-07-30 2013-08-29 Rigel Pharmaceuticals, Inc. Compuestos de 2,4-pirimidindiamina para su uso en el tratamiento o la prevención de enfermedades autoinmunitarias
DK1663242T3 (da) * 2003-08-07 2011-08-01 Rigel Pharmaceuticals Inc 2,4-Pyrimidindiamin-forbindelser og anvendelse som antiproliferative midler
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
KR20060127415A (ko) 2003-12-24 2006-12-12 와이어쓰 천식의 치료방법
US20070232658A1 (en) * 2004-04-08 2007-10-04 Jurgen Wagner Protein Kinase C Inhibitors for the Treatment of Autoimmune Diseases and of Transplant Rejiction
JP2008540436A (ja) * 2005-05-03 2008-11-20 ライジェル ファーマシューティカルズ， インコーポレイテッド Ｊａｋキナーゼインヒビターおよびそれらの使用
JP2010522765A (ja) 2007-03-28 2010-07-08 アレイ バイオファーマ、インコーポレイテッド 受容体チロシンキナーゼとしてのイミダゾ［１，２−ａ］ピリジン化合物
CN101903357A (zh) * 2007-07-17 2010-12-01 里格尔药品股份有限公司 作为pkc抑制剂的环状胺取代的嘧啶二胺
AU2009262068C1 (en) * 2008-06-27 2015-07-02 Celgene Car Llc Heteroaryl compounds and uses thereof
CA2801781C (en) * 2010-07-21 2018-02-27 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof

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EP2389373B1 (en) 2017-05-17
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