CA3208587A1 - Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein - Google Patents

Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Info

Publication number
CA3208587A1
CA3208587A1 CA3208587A CA3208587A CA3208587A1 CA 3208587 A1 CA3208587 A1 CA 3208587A1 CA 3208587 A CA3208587 A CA 3208587A CA 3208587 A CA3208587 A CA 3208587A CA 3208587 A1 CA3208587 A1 CA 3208587A1
Authority
CA
Canada
Prior art keywords
compound
formula
solvent
methods
naoh
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CA3208587A
Other languages
English (en)
French (fr)
Inventor
Terrance Joseph Connolly
Hon-Wah Man
Periyandi Nagarajan
Chinnapillai Rajendiran
Jasti Venkateswarlu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Celgene Corp
Original Assignee
Celgene Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Celgene Corp filed Critical Celgene Corp
Publication of CA3208587A1 publication Critical patent/CA3208587A1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/54—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
    • C07C209/58—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions from or via amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/86—Separation
    • C07C209/88—Separation of optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
    • C07C211/40—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing only non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA3208587A 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein Pending CA3208587A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562196363P 2015-07-24 2015-07-24
US62/196,363 2015-07-24
CA2993173A CA2993173C (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2993173A Division CA2993173C (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Publications (1)

Publication Number Publication Date
CA3208587A1 true CA3208587A1 (en) 2017-02-02

Family

ID=57885143

Family Applications (2)

Application Number Title Priority Date Filing Date
CA3208587A Pending CA3208587A1 (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein
CA2993173A Active CA2993173C (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2993173A Active CA2993173C (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Country Status (9)

Country Link
US (4) US10252981B2 (OSRAM)
EP (2) EP3795553B1 (OSRAM)
JP (2) JP6805232B2 (OSRAM)
CN (1) CN107922287B (OSRAM)
AU (2) AU2016297784B2 (OSRAM)
CA (2) CA3208587A1 (OSRAM)
ES (2) ES2819374T3 (OSRAM)
MX (2) MX385379B (OSRAM)
WO (1) WO2017019487A1 (OSRAM)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180022710A1 (en) 2015-01-29 2018-01-25 Signal Pharmaceuticals, Llc Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
WO2017019487A1 (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
CN111848423B (zh) * 2019-04-30 2022-10-14 尚科生物医药（上海）有限公司 3-氧代环丁基氨基甲酸叔丁酯的制备方法

Family Cites Families (80)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2859239A (en) 1956-08-17 1958-11-04 Dow Chemical Co Acrylic acid compounds
CH549339A (de) 1971-05-12 1974-05-31 Ciba Geigy Ag Herbizides mittel.
US5763647A (en) * 1990-03-30 1998-06-09 Shionogi & Co., Ltd. Preparation of optically active 1,4-bridged-cyclohexane carboxylic acid derivatives
CA2072270A1 (en) 1991-06-26 1992-12-27 Joseph V. Koleske Production of unsaturated cycloaliphatic esters and derivatives thereof
ATE401312T1 (de) 1997-12-15 2008-08-15 Astellas Pharma Inc Pyrimidin-5-carboxamid-derivate
AU5438299A (en) 1998-08-29 2000-03-21 Astrazeneca Ab Pyrimidine compounds
WO2000075113A1 (en) 1999-06-09 2000-12-14 Yamanouchi Pharmaceutical Co., Ltd. Novel heterocyclic carboxamide derivatives
WO2000076980A1 (en) 1999-06-10 2000-12-21 Yamanouchi Pharmaceutical Co., Ltd. Novel nitrogen-contaiing heterocyclic derivatives or salts thereof
US6498165B1 (en) 1999-06-30 2002-12-24 Merck & Co., Inc. Src kinase inhibitor compounds
CA2381882C (en) 1999-08-13 2011-01-25 Vertex Pharmaceuticals Incorporated Inhibitors of c-jun n-terminal kinases (jnk) and other protein kinases
TWI329105B (en) 2002-02-01 2010-08-21 Rigel Pharmaceuticals Inc 2,4-pyrimidinediamine compounds and their uses
GB0206215D0 (en) 2002-03-15 2002-05-01 Novartis Ag Organic compounds
JPWO2003082855A1 (ja) 2002-03-28 2005-08-04 協和醗酵工業株式会社 抗炎症剤
ES2373226T3 (es) 2002-06-28 2012-02-01 Astellas Pharma Inc. Derivado de diaminopirimidincarboxamida.
RS51752B (sr) 2002-07-29 2011-12-31 Rigel Pharmaceuticals Metode tretiranja i prevencije autoimunih oboljenja jedinjenjima 2,4-pirimidindiamina
WO2004054617A1 (ja) 2002-12-13 2004-07-01 Kyowa Hakko Kogyo Co., Ltd. 中枢疾患の予防および／または治療剤
WO2004063141A1 (ja) * 2003-01-16 2004-07-29 Toray Fine Chemicals Co,. Ltd. 光学活性ジアシル酒石酸の回収方法
JP2006516561A (ja) 2003-01-17 2006-07-06 ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー 細胞増殖の阻害剤としての２−アミノピリジン置換ヘテロ環類
ATE440087T1 (de) 2003-01-30 2009-09-15 Boehringer Ingelheim Pharma 2,4-diaminopyrimidinderivate, die sich als inhibitoren von pkc-theta eignen
RU2395500C2 (ru) 2003-08-15 2010-07-27 Новартис Аг 2,4-пиримидиндиамины, применяемые в лечении неопластических болезней, воспалительных и иммунных расстройств
AU2004275733A1 (en) 2003-09-24 2005-04-07 Wyeth Holdings Corporation 5-arylpyrimidines as anticancer agents
WO2005095382A1 (ja) 2004-03-30 2005-10-13 Kyowa Hakko Kogyo Co., Ltd. 抗腫瘍剤
US7601714B2 (en) 2004-07-08 2009-10-13 Boehringer Ingelheim Pharmaceuticals, Inc. Pyrimidine derivatives useful as inhibitors of PKC-theta
US20080027034A1 (en) 2004-09-10 2008-01-31 Shah Tushar P Ciclesonide and Syk Inhibitor Combination and Method of Use Thereof
WO2006027378A1 (en) 2004-09-10 2006-03-16 Altana Pharma Ag Roflumilast and syk inhibitor combination and methods of use thereof
JP2006124387A (ja) 2004-09-30 2006-05-18 Taisho Pharmaceut Co Ltd 新規なキノリン、テトラヒドロキナゾリン、及びピリミジン誘導体と、これらを使用することに関連した治療方法
RU2410379C2 (ru) 2004-09-30 2011-01-27 Тиботек Фармасьютикалз Лтд. 5-замещенные пиримидины, ингибирующие вич
WO2006091737A1 (en) 2005-02-24 2006-08-31 Kemia, Inc. Modulators of gsk-3 activity
JP2008533042A (ja) 2005-03-10 2008-08-21 バイエル・フアーマシユーチカルズ・コーポレーシヨン 過剰増殖性疾患の処置のためのピリミジン誘導体
WO2007032445A1 (ja) 2005-09-16 2007-03-22 Kyowa Hakko Kogyo Co., Ltd. タンパク質キナーゼ阻害剤
WO2008009458A1 (en) 2006-07-21 2008-01-24 Novartis Ag 2, 4 -di (arylaminio) -pyrimidine-5-carboxamide compounds as jak kinases inhibitors
US8188113B2 (en) 2006-09-14 2012-05-29 Deciphera Pharmaceuticals, Inc. Dihydropyridopyrimidinyl, dihydronaphthyidinyl and related compounds useful as kinase inhibitors for the treatment of proliferative diseases
US20080139531A1 (en) 2006-12-04 2008-06-12 Alcon Manufacturing Ltd. Use of connective tissue mast cell stabilizers to facilitate ocular surface re-epithelization and wound repair
CL2007003693A1 (es) 2006-12-22 2008-06-27 Actelion Pharmaceuticals Ltd Compuestos derivados de pirido [3,2-b] [1,4] tiazina; composicion farmaceutica que contiene dichos compuestos; y su uso en el tratamiento de infecciones bacterianas.
ES2593486T3 (es) 2007-04-18 2016-12-09 Pfizer Products Inc. Derivados de sulfonil amida para el tratamiento del crecimiento celular anómalo
US20090036440A1 (en) 2007-04-27 2009-02-05 Astrazeneca Ab Novel pyrimidine derivatives - 816
BRPI0814821A2 (pt) 2007-07-16 2015-02-03 Astrazeneca Ab Composto, composição farmacêutica, e, processo para preparar um composto
EP2183225A1 (en) 2007-07-17 2010-05-12 Rigel Pharmaceuticals, Inc. Cyclic amine substituted pyrimidinediamines as pkc inhibitors
JP5269444B2 (ja) * 2008-03-11 2013-08-21 東ソー・ファインケム株式会社 固体ルイス酸触媒、それを用いたディールスアルダー付加物の製造方法
CA2723205C (en) 2008-04-16 2017-03-14 Portola Pharmaceuticals, Inc. 2,6-diamino-pyrimidin-5-yl-carboxamides as syk or jak kinase inhibitors
KR20100132550A (ko) 2008-04-16 2010-12-17 포톨라 파마슈티컬스, 인코포레이티드 ｓｙｋ 또는 ＪＡＫ 키나제 억제제로서의 ２,６－디아미노-피리미딘－５－일－카르복스아미드
WO2009131687A2 (en) 2008-04-22 2009-10-29 Portola Pharmaceuticals, Inc. Inhibitors of protein kinases
EP2280969A1 (en) 2008-04-29 2011-02-09 F. Hoffmann-La Roche AG Pyrimidinyl pyridone inhibitors of jnk.
WO2009143389A1 (en) 2008-05-21 2009-11-26 Ariad Pharmaceuticals, Inc. Phosphorous derivatives as kinase inhibitors
PE20100087A1 (es) 2008-06-25 2010-02-08 Irm Llc Compuestos y composiciones como inhibidores de cinasa
US8338439B2 (en) 2008-06-27 2012-12-25 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines useful as kinase inhibitors
US8450335B2 (en) 2008-06-27 2013-05-28 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines useful as kinase inhibitors
US20110159019A1 (en) 2008-09-01 2011-06-30 Akira Tanaka 2,4-diaminopyrimidine compound
EP2159220A1 (en) 2008-09-02 2010-03-03 Nabriva Therapeutics AG Organic compounds
TWI453207B (zh) * 2008-09-08 2014-09-21 Signal Pharm Llc 胺基三唑并吡啶，其組合物及使用其之治療方法
JP2012502882A (ja) 2008-09-18 2012-02-02 アステラス製薬株式会社 複素環カルボキサミド化合物
WO2010038081A2 (en) 2008-10-03 2010-04-08 Astrazeneca Ab Heterocyclic derivatives and methods of use thereof
RU2522001C2 (ru) 2008-10-31 2014-07-10 Сентокор Орто Байотек Инк. Дифференцирование человеческих эмбриональных стволовых клеток в линию панкреатических эндокринных клеток
WO2010068863A2 (en) 2008-12-12 2010-06-17 Cystic Fibrosis Foundation Therapeutics, Inc. Pyrimidine compounds and methods of making and using same
WO2010080864A1 (en) 2009-01-12 2010-07-15 Array Biopharma Inc. Piperidine-containing compounds and use thereof
JP2012515148A (ja) 2009-01-13 2012-07-05 グラクソ グループ リミテッド Ｓｙｋキナーゼ阻害剤としてのピリミジンカルボキサミド誘導体
JP5781943B2 (ja) 2009-01-21 2015-09-24 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 炎症性疾患、自己免疫疾患または増殖性疾患の治療に有用なｎ２−（３−ピリジルまたはフェニル）−ｎ４−（４−ピペリジル）−２，４−ピリミジンジアミン誘導体
WO2010129802A1 (en) 2009-05-06 2010-11-11 Portola Pharmaceuticals, Inc. Inhibitors of jak
KR101614572B1 (ko) 2009-05-08 2016-04-21 아스테라스 세이야쿠 가부시키가이샤 디아미노 헤테로환 카르복사미드 화합물
JP2012148977A (ja) 2009-05-20 2012-08-09 Astellas Pharma Inc アミノシクロヘキシルアルキル基を有する２，４−ジアミノピリミジン化合物
CN102498110A (zh) 2009-06-10 2012-06-13 雅培制药有限公司 作为激酶抑制剂的2-(lh-吡唑-4-基氨基)-嘧啶
JP2012197231A (ja) 2009-08-06 2012-10-18 Oncotherapy Science Ltd Ｔｔｋ阻害作用を有するピリジンおよびピリミジン誘導体
WO2011065800A2 (ko) 2009-11-30 2011-06-03 주식회사 오스코텍 피리미딘 유도체, 이의 제조방법 및 이를 함유하는 약학적 조성물
CA2780759A1 (en) 2009-12-01 2011-06-09 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof
EP2582671A4 (en) * 2010-06-17 2014-02-26 Reddys Lab Ltd Dr PROCESS FOR PREPARING A SINGLE ENANTIOMER FROM 3-AMINOPIPERIDIN DIHYDROCHLORIDE
US8710223B2 (en) 2010-07-21 2014-04-29 Rigel Pharmaceuticals, Inc. Protein kinase C inhibitors and uses thereof
US8580805B2 (en) 2010-08-31 2013-11-12 Hubert Maehr Pyrimidine carboxamide derivatives
WO2012045020A1 (en) 2010-09-30 2012-04-05 Portola Pharmaceuticals, Inc. Combinations of 4-(cyclopropylamino)-2-(4-(4-(ethylsulfonyl)piperazin-1-yl)phenylamino)pyrimidine-5-carboxamide and fludarabine
US20130244963A1 (en) 2010-09-30 2013-09-19 Portola Pharmaceuticals, Inc. Combination therapy with 4-(3-(2h-1,2,3-triazol-2-yl)phenylamino)-2-((1r,2s)-2-aminocyclohexylamino)pyrimidine-5-carboxamide
EP4328223A3 (en) 2011-04-22 2024-11-06 Signal Pharmaceuticals, LLC Substituted diaminocarboxamide and diaminocarbonitrile pyrimidines, compositions thereof, and methods of treatment therewith
WO2014019166A1 (zh) * 2012-08-01 2014-02-06 上海威智医药科技有限公司 高活性硼烷类化合物的工业化生产方法
JP2014031327A (ja) * 2012-08-02 2014-02-20 Kaneka Corp 光学活性シス−２−アミノ−シクロヘキサンカルボン酸誘導体およびその前駆体の製造法
ES2812605T3 (es) 2013-12-20 2021-03-17 Signal Pharm Llc Compuestos de diaminopirimidilo sustituidos, composiciones de los mismos y procedimientos de tratamiento con ellos
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
TWI523838B (zh) * 2014-03-21 2016-03-01 Far Eastern New Century Corp Terephthalic acid and 4-methyl-3-cyclohexene-1-carboxylic acid Ester preparation method
HUE054694T2 (hu) 2014-10-06 2021-09-28 Signal Pharm Llc Szubsztituált aminpurin vegyületek, ezek összetételei, és az ezekkel végzett kezelések módszerei
CN107108524A (zh) 2014-12-16 2017-08-29 西格诺药品有限公司 2‑(叔丁基氨基)‑4‑((1r,3r,4r)‑3‑羟基‑4‑甲基环己基氨基)‑嘧啶‑5‑甲酰胺的配制物
JP6903577B2 (ja) 2014-12-16 2021-07-14 シグナル ファーマシューティカルズ，エルエルシー 皮膚におけるｃ−Ｊｕｎ Ｎ末端キナーゼの阻害の測定方法
US20180022710A1 (en) 2015-01-29 2018-01-25 Signal Pharmaceuticals, Llc Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
WO2017019487A1 (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

Also Published As

Publication number Publication date
AU2021201493A1 (en) 2021-03-25
EP3795553B1 (en) 2024-05-15
US20220234990A1 (en) 2022-07-28
US20180215700A1 (en) 2018-08-02
JP2021046426A (ja) 2021-03-25
AU2016297784B2 (en) 2020-12-24
MX2018001004A (es) 2018-06-07
JP7165178B2 (ja) 2022-11-02
US10252981B2 (en) 2019-04-09
JP6805232B2 (ja) 2020-12-23
ES2994877T3 (en) 2025-02-03
US11192847B2 (en) 2021-12-07
WO2017019487A1 (en) 2017-02-02
ES2819374T3 (es) 2021-04-15
US10774033B2 (en) 2020-09-15
US11780801B2 (en) 2023-10-10
HK1255553A1 (en) 2019-08-23
EP3325432A4 (en) 2019-04-24
CN107922287B (zh) 2021-04-09
AU2021201493B2 (en) 2022-07-14
EP3795553A1 (en) 2021-03-24
US20200369600A1 (en) 2020-11-26
JP2018521085A (ja) 2018-08-02
CA2993173C (en) 2023-10-03
MX385379B (es) 2025-03-18
CN107922287A (zh) 2018-04-17
US20190152893A1 (en) 2019-05-23
MX2020001720A (es) 2021-08-13
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