AU2016297784B2 - 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 Download PDF

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AU2016297784B2
AU2016297784B2 AU2016297784A AU2016297784A AU2016297784B2 AU 2016297784 B2 AU2016297784 B2 AU 2016297784B2 AU 2016297784 A AU2016297784 A AU 2016297784A AU 2016297784 A AU2016297784 A AU 2016297784A AU 2016297784 B2 AU2016297784 B2 AU 2016297784B2
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naoh
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AU2016297784A1 (en
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Terrence Joseph Connolly
Hon-Wah Man
Periyandi Nagarajan
Chinnapillai Rajendiran
Jasti Venkateswarlu
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Celgene Corp
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Celgene Corp
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    • 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

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  • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
AU2016297784A 2015-07-24 2016-07-22 Methods of synthesis of (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein Active AU2016297784B2 (en)

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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

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US (4) US10252981B2 (enExample)
EP (2) EP3795553B1 (enExample)
JP (2) JP6805232B2 (enExample)
CN (1) CN107922287B (enExample)
AU (2) AU2016297784B2 (enExample)
CA (2) CA3208587A1 (enExample)
ES (2) ES2994877T3 (enExample)
MX (2) MX385379B (enExample)
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CA2975260C (en) 2015-01-29 2024-05-21 Signal Pharmaceuticals Llc Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
ES2994877T3 (en) * 2015-07-24 2025-02-03 Celgene Corp 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 (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0520419A2 (en) * 1991-06-26 1992-12-30 Union Carbide Chemicals & Plastics Technology Corporation Production of unsaturated cycloaliphatic esters and derivatives thereof
US7358384B2 (en) * 2003-01-16 2008-04-15 Toray Fine Chemicals Co., Ltd. Processes for the recovery of optically active diacyltartaric acids
US9061989B1 (en) * 2014-03-21 2015-06-23 Far Eastern New Century Corporation Method for producing terephthalic acid

Family Cites Families (77)

* 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
AU1507199A (en) 1997-12-15 1999-07-05 Yamanouchi Pharmaceutical Co., Ltd. Novel pyrimidine-5-carboxamide derivatives
DE69933680T2 (de) 1998-08-29 2007-08-23 Astrazeneca Ab Pyrimidine verbindungen
AU5107900A (en) 1999-06-09 2000-12-28 Yamanouchi Pharmaceutical Co., Ltd. Novel heterocyclic carboxamide derivatives
AU5108000A (en) 1999-06-10 2001-01-02 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
HK1045507A1 (zh) 1999-08-12 2002-11-29 Vertex Pharmaceuticals Incorporated C-jun n-末端激酶(jnk)及其他蛋白质激酶的抑制物
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
EP1518855B1 (en) 2002-06-28 2011-10-26 Astellas Pharma Inc. Diaminopyrimidinecarboxa mide derivative
BR0313059B8 (pt) 2002-07-29 2021-07-27 Rigel Pharmaceuticals composto, e, composição farmacêutica
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
MXPA05007503A (es) 2003-01-17 2005-09-21 Warner Lambert Co Heterociclicos 2-aminopiridina sustituidos como inhibidores de proliferacion celular.
DE602004022633D1 (de) 2003-01-30 2009-10-01 Boehringer Ingelheim Pharma 2,4-diaminopyrimidinderivate, die sich als inhibitoren von pkc-theta eignen
TWI378923B (en) 2003-08-15 2012-12-11 Novartis Ag Pyrimidine derivatives
CN1871009A (zh) 2003-09-24 2006-11-29 惠氏控股公司 作为抗癌剂的5－芳基嘧啶
WO2005095382A1 (ja) 2004-03-30 2005-10-13 Kyowa Hakko Kogyo Co., Ltd. 抗腫瘍剤
WO2006014482A1 (en) 2004-07-08 2006-02-09 Boehringer Ingelheim Pharmaceuticals, Inc. Pyrimidine derivatives useful as inhibitors of pkc-theta
EP1796679A1 (en) 2004-09-10 2007-06-20 Altana Pharma AG Ciclesonide and syk inhibitor combination and methods of use thereof
JP2008512429A (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 ロフルミラストと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
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
WO2006099231A1 (en) 2005-03-10 2006-09-21 Bayer Pharmaceuticals Corporation 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
CA2657260A1 (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.
AP2009005010A0 (en) 2007-04-18 2009-10-31 Pfizer Prod Inc Sulfonyl amide derivatives for the treatment of abnormal cell growth
US20090036440A1 (en) 2007-04-27 2009-02-05 Astrazeneca Ab Novel pyrimidine derivatives - 816
WO2009010789A2 (en) 2007-07-16 2009-01-22 Astrazeneca Ab Pyrimidine derivatives 934
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
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
KR20100132550A (ko) 2008-04-16 2010-12-17 포톨라 파마슈티컬스, 인코포레이티드 ｓｙｋ 또는 ＪＡＫ 키나제 억제제로서의 ２,６－디아미노-피리미딘－５－일－카르복스아미드
JP5705720B2 (ja) 2008-04-16 2015-04-22 ポートラ ファーマシューティカルズ， インコーポレイテッド Ｓｙｋまたはｊａｋキナーゼ阻害剤としての２，６−ジアミノ−ピリミジン−５−イル−カルボキサミド
JP2011518219A (ja) 2008-04-22 2011-06-23 ポートラ ファーマシューティカルズ， インコーポレイテッド タンパク質キナーゼの阻害剤
JP5302389B2 (ja) 2008-04-29 2013-10-02 エフ．ホフマン−ラ ロシュ アーゲー Ｊｎｋのピリミジニルピリドンインヒビター
EP2300013B2 (en) 2008-05-21 2024-11-13 Takeda Pharmaceutical Company Limited Phosphorous derivatives as kinase inhibitors
UY31929A (es) 2008-06-25 2010-01-05 Irm Llc Compuestos y composiciones como inhibidores de cinasa
NZ603525A (en) 2008-06-27 2015-02-27 Celgene Avilomics Res Inc Pyrimidine based compound and uses thereof
US8338439B2 (en) 2008-06-27 2012-12-25 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines useful as kinase inhibitors
WO2010024430A1 (ja) 2008-09-01 2010-03-04 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
CA2737738A1 (en) 2008-09-18 2010-03-25 Astellas Pharma Inc. Heterocyclic carboxamide compounds
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
US8513242B2 (en) 2008-12-12 2013-08-20 Cystic Fibrosis Foundation Therapeutics, Inc. Pyrimidine compounds and methods of making and using same
EP2375899B1 (en) 2009-01-12 2015-02-25 Array Biopharma Inc. Piperidine-containing compounds and use thereof in the treatment of diabetes
MX2011007499A (es) 2009-01-13 2011-08-04 Glaxo Group Ltd Derivados de pirimidin-carboxamida como inhibidores de la cinasa syk.
ES2635504T3 (es) 2009-01-21 2017-10-04 Rigel Pharmaceuticals, Inc. Derivados de N2-(3-piridilo o fenil)-N4-(4-piperidil)-2,4-pirimidinadiamina útiles en el tratamiento de enfermedades inflamatorias, toimmunitarias o proliferativas
US8367689B2 (en) 2009-05-06 2013-02-05 Portola Pharmaceuticals, Inc. Inhibitors of JAK
JP5364159B2 (ja) 2009-05-08 2013-12-11 アステラス製薬株式会社 ジアミノへテロ環カルボキサミド化合物
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
US20110130415A1 (en) 2009-12-01 2011-06-02 Rajinder Singh Protein kinase c inhibitors and uses thereof
US20130172562A1 (en) * 2010-06-17 2013-07-04 Dr. Reddy's Laboratories, Inc. Process for the preparation of a single enantiomer of 3-aminopiperidine dihydrochloride
JP6035238B2 (ja) 2010-07-21 2016-11-30 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 プロテインキナーゼｃ阻害剤およびその使用
US8580805B2 (en) 2010-08-31 2013-11-12 Hubert Maehr Pyrimidine carboxamide derivatives
WO2012045010A1 (en) 2010-09-30 2012-04-05 Portola Pharmaceuticals, Inc. Combinations 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
HRP20240097T1 (hr) 2011-04-22 2024-03-29 Signal Pharmaceuticals, Llc Supstituirani diaminokarboksamid i diaminokarbonitril pirimidini, njihovi pripravci i postupci liječenja s njima
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
AR099376A1 (es) 2013-12-20 2016-07-20 Signal Pharm Llc Compuestos de diaminopirimidilo sustituidos, sus composiciones y métodos de tratamiento con aquellos
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
KR20230035424A (ko) 2014-10-06 2023-03-13 시그날 파마소티칼 엘엘씨 치환된 아미노퓨린 화합물, 그의 조성물 및 그를 사용한 치료 방법
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
WO2016100310A1 (en) 2014-12-16 2016-06-23 Signal Pharmaceuticals, Llc Formulations of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methycyclohexylamino)-pyrimidine-5-carboxamide
CA2975260C (en) 2015-01-29 2024-05-21 Signal Pharmaceuticals Llc Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
ES2994877T3 (en) * 2015-07-24 2025-02-03 Celgene Corp Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0520419A2 (en) * 1991-06-26 1992-12-30 Union Carbide Chemicals & Plastics Technology Corporation Production of unsaturated cycloaliphatic esters and derivatives thereof
US7358384B2 (en) * 2003-01-16 2008-04-15 Toray Fine Chemicals Co., Ltd. Processes for the recovery of optically active diacyltartaric acids
US9061989B1 (en) * 2014-03-21 2015-06-23 Far Eastern New Century Corporation Method for producing terephthalic acid

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EP3795553A1 (en) 2021-03-24
CN107922287A (zh) 2018-04-17
US11192847B2 (en) 2021-12-07
US20220234990A1 (en) 2022-07-28
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