EA201001671A1 - Способ стереоселективного ферментативного гидролиза эфира 5-метил-3-нитрометилгексановой кислоты - Google Patents

Способ стереоселективного ферментативного гидролиза эфира 5-метил-3-нитрометилгексановой кислоты

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Publication number
EA201001671A1
EA201001671A1 EA201001671A EA201001671A EA201001671A1 EA 201001671 A1 EA201001671 A1 EA 201001671A1 EA 201001671 A EA201001671 A EA 201001671A EA 201001671 A EA201001671 A EA 201001671A EA 201001671 A1 EA201001671 A1 EA 201001671A1
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EA
Eurasian Patent Office
Prior art keywords
methyl
acid
nitromethylhexanoic
nitroethyl
acid ester
Prior art date
Application number
EA201001671A
Other languages
English (en)
Other versions
EA019285B1 (ru
Inventor
Мартин Альберт
Фердинанд Зерек
Андреас Бергер
Ваандер Риезортс
Хельмут Шваб
Дэниел Лушниг
Питер Ремлер
Джоерг Салченеггер
Дорис Осл
Доминик Де Соуза
Original Assignee
Сандоз Аг
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 Сандоз Аг filed Critical Сандоз Аг
Publication of EA201001671A1 publication Critical patent/EA201001671A1/ru
Publication of EA019285B1 publication Critical patent/EA019285B1/ru

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C205/51—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/008—Preparation of nitrogen-containing organic compounds containing a N-O bond, e.g. nitro (-NO2), nitroso (-NO)
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Данное изобретение относится к способам получения эфира 5-метил-3-нитрометилгексановой кислоты и ее солей. Также описаны способы получения соли 5-метил-3-нитрометилгексановой кислоты и способ получения 3-(аминометил)-5-метилгексановой кислоты. Также описаны (S)-5-метил-3-нитрометилгексановая кислота или (R)-5-метил-3-нитрометилгексановая кислота в энантионасыщенной или энантиочистой формах, а также их соли, эфир (S)-5-метил-3-нитрометилгексановой кислоты или эфир (R)-5-метил-3-нитрометилгексановой кислоты в энантионасыщенной или энантиочистой формах и соединение, а именно соединение формулы (XIII), в рацемической форме, энантионасыщенной или энантиочистой формах.
EA201001671A 2008-05-21 2009-05-19 Способ стереоселективного ферментативного гидролиза эфира 5-метил-3-нитрометилгексановой кислоты EA019285B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12837108P 2008-05-21 2008-05-21
PCT/EP2009/056099 WO2009141362A2 (en) 2008-05-21 2009-05-19 Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester

Publications (2)

Publication Number Publication Date
EA201001671A1 true EA201001671A1 (ru) 2011-10-31
EA019285B1 EA019285B1 (ru) 2014-02-28

Family

ID=41319680

Family Applications (1)

Application Number Title Priority Date Filing Date
EA201001671A EA019285B1 (ru) 2008-05-21 2009-05-19 Способ стереоселективного ферментативного гидролиза эфира 5-метил-3-нитрометилгексановой кислоты

Country Status (13)

Country Link
US (1) US8546112B2 (ru)
EP (1) EP2294207B1 (ru)
KR (1) KR20110025917A (ru)
CN (1) CN102099482B (ru)
AU (1) AU2009248750B2 (ru)
BR (1) BRPI0913094A2 (ru)
CA (1) CA2724828C (ru)
EA (1) EA019285B1 (ru)
IL (1) IL209271A (ru)
MX (1) MX2010012698A (ru)
SI (1) SI2294207T1 (ru)
UA (1) UA103997C2 (ru)
WO (1) WO2009141362A2 (ru)

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US20090312560A1 (en) * 2008-06-10 2009-12-17 Lambertus Thijs Processes for making pregabalin and intermediates therefor
CN103833562B (zh) * 2013-12-04 2015-08-12 惠州市莱佛士制药技术有限公司 一种不对称合成普瑞巴林的制备方法
CN106488906B (zh) 2014-06-12 2018-10-26 斯福瑞有限公司 β-取代的γ-氨基羧酸的制备方法
WO2016075082A1 (en) 2014-11-10 2016-05-19 Sandoz Ag Stereoselective reductive amination of alpha-chiral aldehydes using omega-transaminases for the synthesis of precursors of pregabalin and brivaracetam
EP3088383A1 (de) * 2015-04-29 2016-11-02 K.H.S. Pharma Holding GmbH Optimierte synthese von pregabalin sowie 4-aminobutansäuren unter einsatz eines verbesserten herstellverfahrens von konjugierten nitroalkenen
CN108358799B (zh) * 2018-04-24 2020-11-10 贵州师范大学 一种普瑞巴林的制备方法
EP3819290A4 (en) * 2018-06-06 2022-01-26 Zhejiang Huahai Pharmaceutical Co., Ltd METHOD FOR THE PREPARATION OF PREGABALIN
CN108997128B (zh) * 2018-08-03 2021-02-02 浙江工业大学 一种普瑞巴林中间体3-硝甲基-5-甲基己酸乙酯的制备方法
CN109503403B (zh) * 2018-12-21 2021-11-16 卓和药业集团股份有限公司 一种普瑞巴林的拆分方法
CN110256229A (zh) * 2019-07-29 2019-09-20 常州工程职业技术学院 一种制备3-异丁基戊二酸的方法
CN110803993B (zh) * 2019-11-19 2023-06-30 陕西科技大学 一种普瑞巴林中间体2-羧乙基-3-硝基亚甲基-5-甲基己酸乙酯的合成方法
CN110803994B (zh) * 2019-11-19 2023-06-30 陕西科技大学 一种普瑞巴林中间体3-硝基亚甲基-5-甲基-己酸乙酯的合成方法
CN110862322B (zh) * 2019-11-19 2023-06-30 陕西科技大学 一种普瑞巴林中间体2-乙酰基-3-硝基亚甲基-5-甲基-己酸乙酯的合成方法
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Also Published As

Publication number Publication date
IL209271A (en) 2015-05-31
US20110165636A1 (en) 2011-07-07
UA103997C2 (ru) 2013-12-25
EA019285B1 (ru) 2014-02-28
EP2294207B1 (en) 2012-09-26
CA2724828C (en) 2016-01-12
KR20110025917A (ko) 2011-03-14
IL209271A0 (en) 2011-01-31
BRPI0913094A2 (pt) 2015-08-11
SI2294207T1 (sl) 2013-01-31
MX2010012698A (es) 2011-03-15
CA2724828A1 (en) 2009-11-26
US8546112B2 (en) 2013-10-01
AU2009248750B2 (en) 2015-05-21
WO2009141362A3 (en) 2010-04-15
CN102099482B (zh) 2014-04-16
EP2294207A2 (en) 2011-03-16
CN102099482A (zh) 2011-06-15
AU2009248750A1 (en) 2009-11-26
WO2009141362A2 (en) 2009-11-26

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