CN107922287B - 合成(1r,2r,5r)-5-氨基-2-甲基环己醇盐酸盐的方法和其中可用的中间体 - Google Patents

合成(1r,2r,5r)-5-氨基-2-甲基环己醇盐酸盐的方法和其中可用的中间体 Download PDF

Info

Publication number
CN107922287B
CN107922287B CN201680043308.1A CN201680043308A CN107922287B CN 107922287 B CN107922287 B CN 107922287B CN 201680043308 A CN201680043308 A CN 201680043308A CN 107922287 B CN107922287 B CN 107922287B
Authority
CN
China
Prior art keywords
compound
formula
solvent
contacting
aqueous
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.)
Active
Application number
CN201680043308.1A
Other languages
English (en)
Chinese (zh)
Other versions
CN107922287A (zh
Inventor
泰伦斯·约瑟夫·康诺利
汉华·曼
佩里延迪·纳卡拉占
奇恩纳皮莱·拉詹迪兰
贾斯提·文卡特斯瓦鲁
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 CN107922287A publication Critical patent/CN107922287A/zh
Application granted granted Critical
Publication of CN107922287B publication Critical patent/CN107922287B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/54Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
    • C07C209/58Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions from or via amides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82Purification; Separation; Stabilisation; Use of additives
    • C07C209/86Separation
    • C07C209/88Separation of optical isomers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/39Compounds 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
    • C07C211/40Compounds 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/02Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333Preparation 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
    • C07C67/343Preparation 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
    • C07C67/347Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems 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)
CN201680043308.1A 2015-07-24 2016-07-22 合成(1r,2r,5r)-5-氨基-2-甲基环己醇盐酸盐的方法和其中可用的中间体 Active CN107922287B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562196363P 2015-07-24 2015-07-24
US62/196,363 2015-07-24
PCT/US2016/043511 WO2017019487A1 (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Publications (2)

Publication Number Publication Date
CN107922287A CN107922287A (zh) 2018-04-17
CN107922287B true CN107922287B (zh) 2021-04-09

Family

ID=57885143

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201680043308.1A Active CN107922287B (zh) 2015-07-24 2016-07-22 合成(1r,2r,5r)-5-氨基-2-甲基环己醇盐酸盐的方法和其中可用的中间体

Country Status (9)

Country Link
US (4) US10252981B2 (https=)
EP (2) EP3325432B1 (https=)
JP (2) JP6805232B2 (https=)
CN (1) CN107922287B (https=)
AU (2) AU2016297784B2 (https=)
CA (2) CA3208587A1 (https=)
ES (2) ES2994877T3 (https=)
MX (2) MX2018001004A (https=)
WO (1) WO2017019487A1 (https=)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
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

Citations (5)

* 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
EP0520419A2 (en) * 1991-06-26 1992-12-30 Union Carbide Chemicals & Plastics Technology Corporation Production of unsaturated cycloaliphatic esters and derivatives thereof
CN1315777C (zh) * 2003-01-16 2007-05-16 东丽泛应化学(股) 旋光二酰基酒石酸的回收方法
JP2009214039A (ja) * 2008-03-11 2009-09-24 Tosoh Finechem Corp 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
CN103492370A (zh) * 2011-04-22 2014-01-01 西格诺药品有限公司 取代的二氨基甲酰胺和二氨基甲腈嘧啶,其组合物,和用其治疗的方法

Family Cites Families (75)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
AU1507199A (en) 1997-12-15 1999-07-05 Yamanouchi Pharmaceutical Co., Ltd. Novel pyrimidine-5-carboxamide derivatives
ES2274634T3 (es) 1998-08-29 2007-05-16 Astrazeneca Ab Compuestos de pirimidina.
AU5107900A (en) 1999-06-09 2000-12-28 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
AU5636900A (en) 1999-06-30 2001-01-31 Merck & Co., Inc. Src kinase inhibitor compounds
MXPA02001565A (es) 1999-08-13 2005-07-14 Vertex Pharma Inhibidores de cinasas c-jun n-terminal (jnk) y de otras cinasas proteicas.
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
AU2003244098A1 (en) 2002-06-28 2004-01-19 Yamanouchi Pharmaceutical Co., Ltd. Diaminopyrimidinecarboxa mide derivative
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
JPWO2004054617A1 (ja) 2002-12-13 2006-04-20 協和醗酵工業株式会社 中枢疾患の予防および/または治療剤
EP1590341B1 (en) 2003-01-17 2009-06-17 Warner-Lambert Company LLC 2-aminopyridine substituted heterocycles as inhibitors of cellular proliferation
ATE440087T1 (de) 2003-01-30 2009-09-15 Boehringer Ingelheim Pharma 2,4-diaminopyrimidinderivate, die sich als inhibitoren von pkc-theta eignen
NZ585188A (en) 2003-08-15 2011-09-30 Novartis Ag 2,4-Pyrimidinediamines useful in the treatment of neoplastic diseases, inflammatory and immune system disorders
JP2007506746A (ja) 2003-09-24 2007-03-22 ワイス・ホールディングズ・コーポレイション 抗癌剤としての5−アリールピリミジン類
WO2005095382A1 (ja) 2004-03-30 2005-10-13 Kyowa Hakko Kogyo Co., Ltd. 抗腫瘍剤
JP2008505910A (ja) 2004-07-08 2008-02-28 ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド Pkc−シータのインヒビターとして有用なピリミジン誘導体
EP1796679A1 (en) 2004-09-10 2007-06-20 Altana Pharma AG Ciclesonide and syk inhibitor combination and methods of use thereof
CA2579017A1 (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
ATE542802T1 (de) 2004-09-30 2012-02-15 Tibotec Pharm Ltd Hiv-inhibierende 5-substituierte pyrimidine
WO2006091737A1 (en) 2005-02-24 2006-08-31 Kemia, Inc. Modulators of gsk-3 activity
KR20080004488A (ko) 2005-03-10 2008-01-09 바이엘 파마슈티칼스 코포레이션 과다증식성 장애 치료용 피리미딘 유도체
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
MX2009000769A (es) 2006-07-21 2009-01-28 Novartis Ag Compuestos de 2,4-di(arilaminio)-pirimidin-5-carboxamida como inhibidores de cinasas jak.
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.
BRPI0810411B8 (pt) 2007-04-18 2021-05-25 Pfizer Prod Inc derivados de sulfonil amida para o tratamento de crescimento celular anormal, seu sos, bem como composição farmacêutica
WO2008132505A1 (en) 2007-04-27 2008-11-06 Astrazeneca Ab N' - (phenyl) -n- (morpholin-4-yl-pyridin-2-yl) -pyrimidine-2, 4-diamine derivatives as ephb4 kinase inhibitors for the treatment of proliferative conditions
EP2183242A2 (en) 2007-07-16 2010-05-12 AstraZeneca AB Pyrimidine derivatives 934
CA2693594A1 (en) 2007-07-17 2009-01-22 Rigel Pharmaceuticals, Inc. Cyclic amine substituted pyrimidinediamines as pkc inhibitors
SG2014015085A (en) 2008-04-16 2014-06-27 Portola Pharm Inc 2,6-diamino-pyrimidin-5-yl-carboxamides as syk or jak kinases inhibitors
EA024109B1 (ru) 2008-04-16 2016-08-31 Портола Фармасьютиклз, Инк. Ингибиторы протеинкиназ
NZ588830A (en) 2008-04-22 2012-11-30 Portola Pharm Inc Inhibitors of protein kinases
WO2009132980A1 (en) 2008-04-29 2009-11-05 F. Hoffmann-La Roche Ag Pyrimidinyl pyridone inhibitors of jnk.
PT2300013T (pt) 2008-05-21 2017-10-31 Ariad Pharma Inc Derivados de fósforo como inibidores de cinases
UY31929A (es) 2008-06-25 2010-01-05 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
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
JP5644499B2 (ja) 2008-09-01 2014-12-24 アステラス製薬株式会社 2,4−ジアミノピリミジン化合物
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
MX2011002825A (es) 2008-09-18 2011-04-05 Astellas Pharma Inc Compuestos heterociclicos de carboxamida.
TW201016676A (en) 2008-10-03 2010-05-01 Astrazeneca Ab Heterocyclic derivatives and methods of use thereof
PL2346988T3 (pl) 2008-10-31 2017-10-31 Janssen Biotech Inc Różnicowanie ludzkich zarodkowych komórek macierzystych do linii endokrynnej trzustki
US8513242B2 (en) 2008-12-12 2013-08-20 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
AU2010219097A1 (en) 2009-01-13 2011-08-04 Glaxo Group Limited Pyrimidinecarboxamide derivatives as inhibitors of SYK kinase
CA2749837C (en) 2009-01-21 2017-07-11 Rigel Pharmaceuticals, Inc. Derivatives of n2-(3-pyridil or phenyl)-n4-(4-piperidyl)-2,4-pyrimidinediamine useful in the treatment of inflammatory, autoimmune or proliferative diseases
AR076550A1 (es) 2009-05-06 2011-06-22 Portola Pharm Inc Inhibidores de la janus tirosina kinasa (jak)
SI2428508T1 (sl) 2009-05-08 2016-04-29 Astellas Pharma Inc. Diamino heterociklična karboksamidna spojina
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
WO2010144468A1 (en) 2009-06-10 2010-12-16 Abbott Laboratories 2- ( lh-pyrazol-4 -ylamino ) -pyrimidine as kinase inhibitors
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
US20110130415A1 (en) 2009-12-01 2011-06-02 Rajinder Singh 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
EP2595982B1 (en) 2010-07-21 2018-06-13 Rigel Pharmaceuticals, Inc. Protein kinase c inhibitors and uses thereof
US8580805B2 (en) 2010-08-31 2013-11-12 Hubert Maehr Pyrimidine carboxamide derivatives
WO2012044936A1 (en) 2010-09-30 2012-04-05 Portola Pharmaceuticals, Inc. Combination therapy with 4-(3-(2h-1,2,3-triazol-2-yl)phenylamino)-2-((1r,2s)-2-aminocyclohexylamino)pyrimidine-5-carboxamide
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
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
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
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
MX388321B (es) 2014-10-06 2025-03-19 Signal Pharm Llc Compuestos de aminopurina sustituida, composiciones del mismo, y metodos de tratamiento con los mismos.
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
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
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
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

Patent Citations (5)

* 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
EP0520419A2 (en) * 1991-06-26 1992-12-30 Union Carbide Chemicals & Plastics Technology Corporation Production of unsaturated cycloaliphatic esters and derivatives thereof
CN1315777C (zh) * 2003-01-16 2007-05-16 东丽泛应化学(股) 旋光二酰基酒石酸的回收方法
JP2009214039A (ja) * 2008-03-11 2009-09-24 Tosoh Finechem Corp 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
CN103492370A (zh) * 2011-04-22 2014-01-01 西格诺药品有限公司 取代的二氨基甲酰胺和二氨基甲腈嘧啶,其组合物,和用其治疗的方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Bis(phosphine)cobalt Dialkyl Complexes for Directed Catalytic Alkene Hydrogenation;Max R. Friedfeld, Grant W. Margulieux, Brian A. Schaefer et al.;《Journal of the American Chemical Society 》;20140828;第136卷(第38期);第S8页第3段 *
Enantiomerically Pure Isophorone Diamine [3-(Aminomethyl)-3,5,5-trimethylcyclohexylamine]: A Chiral 1,4-Diamine Building Block Made Available on Large Scale;Albrecht BerkesselKatrin Roland,Michael Schro等;《Journal of Organic Chemistry》;20061208;第71卷(第25期);9312-9318 *

Also Published As

Publication number Publication date
JP7165178B2 (ja) 2022-11-02
JP2021046426A (ja) 2021-03-25
EP3795553B1 (en) 2024-05-15
EP3795553A1 (en) 2021-03-24
AU2016297784B2 (en) 2020-12-24
JP2018521085A (ja) 2018-08-02
AU2021201493B2 (en) 2022-07-14
MX2020001720A (es) 2021-08-13
AU2021201493A1 (en) 2021-03-25
EP3325432B1 (en) 2020-09-02
AU2016297784A1 (en) 2018-02-08
ES2819374T3 (es) 2021-04-15
JP6805232B2 (ja) 2020-12-23
MX385379B (es) 2025-03-18
CN107922287A (zh) 2018-04-17
US20200369600A1 (en) 2020-11-26
US20190152893A1 (en) 2019-05-23
US11192847B2 (en) 2021-12-07
US20220234990A1 (en) 2022-07-28
ES2994877T3 (en) 2025-02-03
HK1255553A1 (en) 2019-08-23
CA3208587A1 (en) 2017-02-02
EP3325432A1 (en) 2018-05-30
EP3325432A4 (en) 2019-04-24
US10252981B2 (en) 2019-04-09
US20180215700A1 (en) 2018-08-02
CA2993173A1 (en) 2017-02-02
MX2018001004A (es) 2018-06-07
US10774033B2 (en) 2020-09-15
WO2017019487A1 (en) 2017-02-02
US11780801B2 (en) 2023-10-10
CA2993173C (en) 2023-10-03

Similar Documents

Publication Publication Date Title
RU2506264C2 (ru) Пиримидин-замещенные пуриновые соединения в качестве ингибиторов киназы (или киназ)
US8383608B2 (en) Imidazolidine compounds as androgen receptor modulators
EP4507691A2 (en) Jak inhibitor analogs, formulations, and uses thereof
US11780801B2 (en) Methods of synthesis of (1R,2R,5R)-5-amino-2-methyl-cyclohexanol hydrochloride and intermediates useful therein
CN105636948A (zh) 作为葛瑞林o-酰基转移酶抑制剂的被取代的哌啶基-乙基-嘧啶
JP2020183437A (ja) 2−(tert−ブチルアミノ)−4−((1R,3R,4R)−3−ヒドロキシ−4−メチルシクロヘキシルアミノ)−ピリミジン−5−カルボキサミドの固体形態、その組成物、及びその使用方法
HK40040730A (en) Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein
HK40040730B (en) Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein
HK1255553B (en) Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein
HK40122633A (zh) Jak抑制剂类似物、制剂及其用途
CN110229146B (zh) 组蛋白去乙酰化酶抑制剂及其制备方法与用途
CN108409729A (zh) 苯基八氢-1H-吡啶并[1,2-a]吡嗪衍生物及其用途

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant