JP6805232B2 - (1r,2r,5r)−5−アミノ−2−メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体 - Google Patents
(1r,2r,5r)−5−アミノ−2−メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体 Download PDFInfo
- Publication number
- JP6805232B2 JP6805232B2 JP2018503482A JP2018503482A JP6805232B2 JP 6805232 B2 JP6805232 B2 JP 6805232B2 JP 2018503482 A JP2018503482 A JP 2018503482A JP 2018503482 A JP2018503482 A JP 2018503482A JP 6805232 B2 JP6805232 B2 JP 6805232B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- solvent
- naoh
- dcm
- 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
Links
- GJIKAJOLWXMKEG-UHFFFAOYSA-N CC(CC1)=CCC1N Chemical compound CC(CC1)=CCC1N GJIKAJOLWXMKEG-UHFFFAOYSA-N 0.000 description 2
- 0 C[C@@](CC[C@](C1)N*)[C@@]1O Chemical compound C[C@@](CC[C@](C1)N*)[C@@]1O 0.000 description 2
- PCOYCFJCVTWMFV-JTQLQIEISA-N CC(C)(C)OC(N[C@H]1CC=C(C)CC1)=O Chemical compound CC(C)(C)OC(N[C@H]1CC=C(C)CC1)=O PCOYCFJCVTWMFV-JTQLQIEISA-N 0.000 description 1
- YOUXMVZSALAVJO-UHFFFAOYSA-N CC(CC1)=CCC1C(N)=O Chemical compound CC(CC1)=CCC1C(N)=O YOUXMVZSALAVJO-UHFFFAOYSA-N 0.000 description 1
- OYOQOLNBTPTFEM-UHFFFAOYSA-N CC(CC1)=CCC1C(O)=O Chemical compound CC(CC1)=CCC1C(O)=O OYOQOLNBTPTFEM-UHFFFAOYSA-N 0.000 description 1
- JNDBPUPULVCVFC-UHFFFAOYSA-N CC(CC1)=CCC1C(OC)=O Chemical compound CC(CC1)=CCC1C(OC)=O JNDBPUPULVCVFC-UHFFFAOYSA-N 0.000 description 1
Images
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)
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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020200723A Division JP7165178B2 (ja) | 2015-07-24 | 2020-12-03 | (1r,2r,5r)-5-アミノ-2-メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018521085A JP2018521085A (ja) | 2018-08-02 |
| JP2018521085A5 JP2018521085A5 (enExample) | 2019-08-22 |
| JP6805232B2 true JP6805232B2 (ja) | 2020-12-23 |
Family
ID=57885143
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018503482A Active JP6805232B2 (ja) | 2015-07-24 | 2016-07-22 | (1r,2r,5r)−5−アミノ−2−メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体 |
| JP2020200723A Active JP7165178B2 (ja) | 2015-07-24 | 2020-12-03 | (1r,2r,5r)-5-アミノ-2-メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020200723A Active JP7165178B2 (ja) | 2015-07-24 | 2020-12-03 | (1r,2r,5r)-5-アミノ-2-メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体 |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US10252981B2 (enExample) |
| EP (2) | EP3795553B1 (enExample) |
| JP (2) | JP6805232B2 (enExample) |
| CN (1) | CN107922287B (enExample) |
| AU (2) | AU2016297784B2 (enExample) |
| CA (2) | CA2993173C (enExample) |
| ES (2) | ES2994877T3 (enExample) |
| MX (2) | MX385379B (enExample) |
| WO (1) | WO2017019487A1 (enExample) |
Families Citing this family (3)
| 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)
| 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 |
| EP0520419A3 (en) * | 1991-06-26 | 1993-06-16 | Union Carbide Chemicals & Plastics Technology Corporation | Production of unsaturated cycloaliphatic esters and derivatives thereof |
| ATE401312T1 (de) | 1997-12-15 | 2008-08-15 | Astellas Pharma Inc | Pyrimidin-5-carboxamid-derivate |
| ATE342892T1 (de) | 1998-08-29 | 2006-11-15 | Astrazeneca Ab | Pyrimidine verbindungen |
| 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 |
| JP2003523942A (ja) | 1999-06-30 | 2003-08-12 | メルク エンド カムパニー インコーポレーテッド | Srcキナーゼ阻害剤化合物 |
| PL366110A1 (en) | 1999-08-13 | 2005-01-24 | 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 |
| AU2003220968A1 (en) | 2002-03-28 | 2003-10-13 | Kyowa Hakko Kogyo Co., Ltd. | Anti-inflammatory agent |
| JP4529685B2 (ja) | 2002-06-28 | 2010-08-25 | アステラス製薬株式会社 | ジアミノピリミジンカルボキサミド誘導体 |
| JP2006514989A (ja) | 2002-07-29 | 2006-05-18 | ライジェル ファーマシューティカルズ | 2,4−ピリミジンジアミン化合物による自己免疫疾患の治療および予防方法 |
| 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 |
| AU2003289487A1 (en) * | 2003-01-16 | 2004-08-10 | Toray Fine Chemicals Co, . Ltd. | Processes for the recovery of optically active diacyltartatic acids |
| MXPA05007503A (es) | 2003-01-17 | 2005-09-21 | Warner Lambert Co | Heterociclicos 2-aminopiridina sustituidos como inhibidores de proliferacion celular. |
| EP1590334B1 (en) | 2003-01-30 | 2009-08-19 | Boehringer Ingelheim Pharmaceuticals Inc. | 2,4-diaminopyrimidine derivatives useful as inhibitors of pkc-theta |
| PL2287156T3 (pl) | 2003-08-15 | 2013-11-29 | Novartis Ag | 2,4-Di(fenyloamino)-pirymidyny stosowane w leczeniu chorób nowotworowych, chorób zapalnych i zaburzeń układu immunologicznego |
| ATE432077T1 (de) | 2003-09-24 | 2009-06-15 | Wyeth Corp | 5-arylpyrimidine als anti-krebs-mittel |
| EP1749827A4 (en) | 2004-03-30 | 2010-04-21 | Kyowa Hakko Kirin Co Ltd | ANTITUMOR AGENTS |
| CA2571937A1 (en) | 2004-07-08 | 2006-02-09 | Boehringer Ingelheim Pharmaceuticals, Inc. | Pyrimidine derivatives useful as inhibitors of pkc-theta |
| EP1791538A1 (en) | 2004-09-10 | 2007-06-06 | Altana Pharma AG | Roflumilast and syk inhibitor combination and methods of use thereof |
| JP2008512428A (ja) | 2004-09-10 | 2008-04-24 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | シクレソニドとSykインヒビターとの組合せ物並びにその使用方法 |
| 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 |
| TW200626561A (en) | 2004-09-30 | 2006-08-01 | Tibotec Pharm Ltd | HIV inhibiting 5-substituted pyrimidines |
| WO2006091737A1 (en) | 2005-02-24 | 2006-08-31 | Kemia, Inc. | Modulators of gsk-3 activity |
| US20110098301A1 (en) | 2005-03-10 | 2011-04-28 | Bayer Healthcare Llc | Pyrimidine Derivatives for Treatment of Hyperproliferative Disorders |
| 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 |
| RU2009105826A (ru) | 2006-07-21 | 2010-08-27 | Новартис АГ (CH) | 2,4-ди(ариламино)питимидин-5-карбоксамидные соединения в качестве ингибиторов jak-киназ |
| 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. |
| NZ580372A (en) | 2007-04-18 | 2012-01-12 | Pfizer Prod Inc | Pyrimidine and triazine derivatives including a sulfonamide group for the treatment of abnormal cell growth such as cancer |
| 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 |
| CA2693880A1 (en) | 2007-07-16 | 2009-01-22 | Astrazeneca Ab | Pyrimidine derivatives 934 |
| NZ582485A (en) | 2007-07-17 | 2012-05-25 | 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 |
| EP2323993B1 (en) | 2008-04-16 | 2015-06-03 | Portola Pharmaceuticals, Inc. | 2,6-diamino- pyrimidin- 5-yl-carboxamides as syk or jak kinases inhibitors |
| MY155639A (en) | 2008-04-16 | 2015-11-13 | Portola Pharm Inc | 2, 6-diamino-pyrimidin-5-yl-carboxamides as syk or jak kinases inhibitors |
| BRPI0910668A2 (pt) | 2008-04-22 | 2019-09-24 | Portola Pharmaceutiacals Inc | inibidores de proteína quinases |
| EP2280969A1 (en) | 2008-04-29 | 2011-02-09 | F. Hoffmann-La Roche AG | Pyrimidinyl pyridone inhibitors of jnk. |
| KR101860057B1 (ko) | 2008-05-21 | 2018-05-21 | 어리어드 파마슈티칼스, 인코포레이티드 | 키나아제 억제제로서 포스포러스 유도체 |
| UY31929A (es) | 2008-06-25 | 2010-01-05 | Irm Llc | Compuestos y composiciones como inhibidores de cinasa |
| EP2361248B1 (en) | 2008-06-27 | 2018-09-19 | Celgene CAR LLC | Heteroaryl compounds and uses thereof |
| US8338439B2 (en) | 2008-06-27 | 2012-12-25 | Celgene Avilomics Research, Inc. | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| MX2011002306A (es) | 2008-09-01 | 2011-05-25 | Astellas Pharma Inc | Compuesto de 2,4-diaminopirimidina. |
| 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 |
| CN102272291B (zh) | 2008-10-31 | 2018-01-16 | 詹森生物科技公司 | 人胚胎干细胞向胰腺内分泌谱系的分化 |
| WO2010068863A2 (en) | 2008-12-12 | 2010-06-17 | Cystic Fibrosis Foundation Therapeutics, Inc. | Pyrimidine compounds and methods of making and using same |
| JP5683489B2 (ja) | 2009-01-12 | 2015-03-11 | アレイ バイオファーマ、インコーポレイテッド | ピペリジン含有化合物およびその用途 |
| BRPI1006162A2 (pt) | 2009-01-13 | 2019-09-24 | Glaxo Group Ltd | "composto,processo para preparar um composto,formulação farmacêutica,e uso de um composto". |
| 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 |
| AR076550A1 (es) | 2009-05-06 | 2011-06-22 | Portola Pharm Inc | Inhibidores de la janus tirosina kinasa (jak) |
| HUE026647T2 (en) | 2009-05-08 | 2016-07-28 | Astellas Pharma Inc | Diamino heterocyclic carboxamide compound |
| 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 |
| MX2011013325A (es) | 2009-06-10 | 2012-04-30 | Abbott Lab | 2-(lh-pirazol-4-ilamino)-pirimidina como inhibidores de cinasa. |
| 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 |
| WO2011068898A1 (en) | 2009-12-01 | 2011-06-09 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| JP2013533866A (ja) * | 2010-06-17 | 2013-08-29 | ドクター レディズ ラボラトリーズ リミテッド | 3−アミノピペリジンジヒドロクロリドの単一の鏡像異性体を調製するための方法 |
| WO2012012619A1 (en) | 2010-07-21 | 2012-01-26 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| US8580805B2 (en) | 2010-08-31 | 2013-11-12 | Hubert Maehr | Pyrimidine carboxamide derivatives |
| US20130252917A1 (en) | 2010-09-30 | 2013-09-26 | Portola Pharmaceuticals, Inc. | Combination therapy of 4-(3-(2h-1,2,3-triazo-2-yl)phenylamino)-2-((1r,2s)-2-aminocyclohexylamino)pyrimidine-5-carboxamide and fludarabine |
| 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 |
| KR101962488B1 (ko) * | 2011-04-22 | 2019-03-26 | 시그날 파마소티칼 엘엘씨 | 치환된 디아미노카르복스아미드 및 디아미노카르보니트릴 피리미딘, 그의 조성물, 및 그를 사용하는 치료 방법 |
| 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 |
| WO2015095679A1 (en) | 2013-12-20 | 2015-06-25 | 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 |
| TW201629063A (zh) | 2014-10-06 | 2016-08-16 | 標誌製藥公司 | 經取代胺基嘌呤化合物、其組合物及用其之治療方法 |
| ES2882954T3 (es) | 2014-12-16 | 2021-12-03 | Signal Pharm Llc | Usos médicos que comprenden métodos para la medición de la inhibición de la quinasa c-Jun N-terminal en la piel |
| ES2877642T3 (es) | 2014-12-16 | 2021-11-17 | Signal Pharm Llc | Formulaciones de 2-(terc-butilamino)-4-((1R,3R,4R)-3-hidroxi-4-metilciclohexilamino)-pirimidin-5-carboxamida |
| 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 |
-
2016
- 2016-07-22 WO PCT/US2016/043511 patent/WO2017019487A1/en not_active Ceased
- 2016-07-22 CA CA2993173A patent/CA2993173C/en active Active
- 2016-07-22 EP EP20193348.8A patent/EP3795553B1/en active Active
- 2016-07-22 CA CA3208587A patent/CA3208587A1/en active Pending
- 2016-07-22 ES ES20193348T patent/ES2994877T3/es active Active
- 2016-07-22 EP EP16831114.0A patent/EP3325432B1/en active Active
- 2016-07-22 JP JP2018503482A patent/JP6805232B2/ja active Active
- 2016-07-22 MX MX2020001720A patent/MX385379B/es unknown
- 2016-07-22 AU AU2016297784A patent/AU2016297784B2/en active Active
- 2016-07-22 US US15/746,853 patent/US10252981B2/en active Active
- 2016-07-22 ES ES16831114T patent/ES2819374T3/es active Active
- 2016-07-22 MX MX2018001004A patent/MX2018001004A/es active IP Right Grant
- 2016-07-22 CN CN201680043308.1A patent/CN107922287B/zh active Active
-
2019
- 2019-01-28 US US16/258,802 patent/US10774033B2/en active Active
-
2020
- 2020-08-13 US US16/992,219 patent/US11192847B2/en active Active
- 2020-12-03 JP JP2020200723A patent/JP7165178B2/ja active Active
-
2021
- 2021-03-09 AU AU2021201493A patent/AU2021201493B2/en active Active
- 2021-11-03 US US17/518,552 patent/US11780801B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US10774033B2 (en) | 2020-09-15 |
| ES2994877T3 (en) | 2025-02-03 |
| EP3795553B1 (en) | 2024-05-15 |
| CA2993173A1 (en) | 2017-02-02 |
| AU2016297784A1 (en) | 2018-02-08 |
| MX2020001720A (es) | 2021-08-13 |
| ES2819374T3 (es) | 2021-04-15 |
| AU2021201493A1 (en) | 2021-03-25 |
| EP3325432B1 (en) | 2020-09-02 |
| WO2017019487A1 (en) | 2017-02-02 |
| HK1255553A1 (en) | 2019-08-23 |
| CN107922287A (zh) | 2018-04-17 |
| US11780801B2 (en) | 2023-10-10 |
| EP3795553A1 (en) | 2021-03-24 |
| US20190152893A1 (en) | 2019-05-23 |
| JP7165178B2 (ja) | 2022-11-02 |
| CN107922287B (zh) | 2021-04-09 |
| US20220234990A1 (en) | 2022-07-28 |
| CA3208587A1 (en) | 2017-02-02 |
| MX2018001004A (es) | 2018-06-07 |
| JP2018521085A (ja) | 2018-08-02 |
| US10252981B2 (en) | 2019-04-09 |
| EP3325432A1 (en) | 2018-05-30 |
| JP2021046426A (ja) | 2021-03-25 |
| CA2993173C (en) | 2023-10-03 |
| AU2016297784B2 (en) | 2020-12-24 |
| MX385379B (es) | 2025-03-18 |
| US20180215700A1 (en) | 2018-08-02 |
| AU2021201493B2 (en) | 2022-07-14 |
| US20200369600A1 (en) | 2020-11-26 |
| US11192847B2 (en) | 2021-12-07 |
| EP3325432A4 (en) | 2019-04-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4674088B2 (ja) | Gsk3で選択的な阻害作用を示す新規な化合物 | |
| JP7165178B2 (ja) | (1r,2r,5r)-5-アミノ-2-メチルシクロヘキサノール塩酸塩の合成方法及びそれに有用な中間体 | |
| RS59909B1 (sr) | Benzoimidazol-2-il pirimidinski modulatori histaminskog h4 receptora | |
| EP3752497B1 (en) | P300/cbp hat inhibitors | |
| UA105377C2 (uk) | Заміщені похідні індазола і азаіндазола як модулятори гамма-секретази | |
| CN106573907B (zh) | 喹啉衍生物及其用于神经退化性疾病的用途 | |
| 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 | |
| AU2013235729A1 (en) | Compositions and methods for inhibition of cathepsins | |
| AU2020354629A1 (en) | JAK inhibitors | |
| HK40040730B (en) | Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein | |
| HK40040730A (en) | Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein | |
| AU2015367396C1 (en) | 3-(6-alkoxy-5-chlorobenzo[d]isoxazol-3-yl)propanoic acid useful as kynurenine monooxygenase inhibitors | |
| HK1255553B (en) | Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein | |
| JP2006232671A (ja) | 新規セレナゾリン誘導体 | |
| HK40122633A (zh) | Jak抑制剂类似物、制剂及其用途 | |
| KR20220010493A (ko) | 효소 11-베타 탈수소효소 유형 1(11β-HSD1)의 환원효소 활성의 효과적이고 선택적인 저해제로 사용되기에 적합한 아다만틸 옥사디아졸의 유도체 및 그 약학적으로 허용가능한 용매화물, 수화물 및 염, 이를 포함하는 약학적 조성물, 합성 방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20190708 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20190708 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20200528 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200609 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200908 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20200909 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20201104 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20201203 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 6805232 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |