CR8686A - Biconversion estereoselectiva de dinitrilos alifaticos en acidos cianocarboxilicos - Google Patents
Biconversion estereoselectiva de dinitrilos alifaticos en acidos cianocarboxilicosInfo
- Publication number
- CR8686A CR8686A CR8686A CR8686A CR8686A CR 8686 A CR8686 A CR 8686A CR 8686 A CR8686 A CR 8686A CR 8686 A CR8686 A CR 8686A CR 8686 A CR8686 A CR 8686A
- Authority
- CR
- Costa Rica
- Prior art keywords
- stereoselective
- acids
- dinitrils
- cyanocarboxyl
- biconversion
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 230000000707 stereoselective effect Effects 0.000 title abstract 2
- -1 CYANOCARBOXYL ACIDS Chemical class 0.000 title 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 abstract 2
- 229960001233 pregabalin Drugs 0.000 abstract 2
- MGWZYUMZVZMKTN-ZETCQYMHSA-N (3s)-3-cyano-5-methylhexanoic acid Chemical compound CC(C)C[C@H](C#N)CC(O)=O MGWZYUMZVZMKTN-ZETCQYMHSA-N 0.000 abstract 1
- KOINRLSRVTULIE-UHFFFAOYSA-N 2-(2-methylpropyl)butanedinitrile Chemical compound CC(C)CC(C#N)CC#N KOINRLSRVTULIE-UHFFFAOYSA-N 0.000 abstract 1
- 208000014644 Brain disease Diseases 0.000 abstract 1
- 208000028017 Psychotic disease Diseases 0.000 abstract 1
- 208000027520 Somatoform disease Diseases 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical class OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 208000027753 pain disease Diseases 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
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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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
-
- 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
- C12P13/002—Nitriles (-CN)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- 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
- C12P13/001—Amines; Imines
-
- 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
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/20—Oxygen containing
- Y10T436/200833—Carbonyl, ether, aldehyde or ketone containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/20—Oxygen containing
- Y10T436/207497—Molecular oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
La presente invencion esta dirigida a una bioconversion regio- y estereoselectiva de dinitrilos alifaticos seleccionados en los correspondientes acidos cianocarboxilicos. Mas particularmente, la presente invencion proporciona metodos para la conversion de 2-isobutil-succinonitrilo en acido (s) -3-ciano- 5- metilhexanoico, el cual es un producto intermedio util en la sintesis de acido (s)-3 (aminometil)-5-metilhexanoico (pregabalina). La pregabalina puede usarse para tratar ciertas enfermedades cerebrales, por ejemplo, en el tratamiento y prevencion de trastornos repentinos, dolor y trastornos psicoticos.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56213304P | 2004-04-14 | 2004-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CR8686A true CR8686A (es) | 2006-11-21 |
Family
ID=34962755
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CR8686A CR8686A (es) | 2004-04-14 | 2006-10-12 | Biconversion estereoselectiva de dinitrilos alifaticos en acidos cianocarboxilicos |
| CR20110356A CR20110356A (es) | 2004-04-14 | 2011-06-22 | Bioconversion estereoselectiva de dinitrilos alifaticos en acidos cianocarboxilicos (divisional exp. 8686) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CR20110356A CR20110356A (es) | 2004-04-14 | 2011-06-22 | Bioconversion estereoselectiva de dinitrilos alifaticos en acidos cianocarboxilicos (divisional exp. 8686) |
Country Status (43)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100491282B1 (ko) | 1996-07-24 | 2005-05-24 | 워너-램버트 캄파니 엘엘씨 | 통증 치료용 이소부틸가바 및 그의 유도체 |
| AT412092B (de) * | 2003-02-27 | 2004-09-27 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung chiraler alpha-hydroxycarbonsäuren durch enzymatische hydrolyse von chiralen cyanhydrinen |
| EP1866275A1 (en) | 2005-04-06 | 2007-12-19 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of pregabalin |
| US7488846B2 (en) | 2005-04-11 | 2009-02-10 | Teva Pharmaceuical Industries Ltd. | Pregabalin free of lactam and a process for preparation thereof |
| CA2604624A1 (en) | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid |
| JP2008505980A (ja) | 2005-05-10 | 2008-02-28 | テバ ファーマシューティカル インダストリーズ リミティド | イソブチルグルタル酸を有さないプレガバリン及びその調製方法 |
| US7763749B2 (en) | 2005-05-10 | 2010-07-27 | Teva Pharmaceutical Industries Ltd. | Method for the preparation of Pregabalin and salts thereof |
| ES2398579T3 (es) | 2005-09-19 | 2013-03-20 | Teva Pharmaceutical Industries Ltd | Una síntesis asimétrica de ácido (S)-(+)-3-(aminometil)-5-metilhexanoico |
| US20070141684A1 (en) * | 2005-12-21 | 2007-06-21 | Pfizer Inc | Preparation of gamma-amino acids having affinity for the alpha-2-delta protein |
| TW200815323A (en) | 2006-05-24 | 2008-04-01 | Teva Pharma | Processes for the preparation of R-(+)-3-(carbamoylmethyl)-5-methylhexanoic acid and salts thereof |
| EP2071032A3 (en) * | 2006-05-31 | 2009-07-08 | Teva Pharmaceutical Industries Ltd | The use of enzymatic resolution for the preparation of intermediates of pregabalin |
| EP1881077A1 (en) * | 2006-07-19 | 2008-01-23 | Solvay Organics GmbH | Process for the production of fluorine containing a-hydroxy carboxylic acids |
| CA2681313C (en) | 2007-03-22 | 2012-09-11 | Teva Pharmaceutical Industries Ltd. | Synthesis of (s)-(+)-3-(aminomethyl)-5-methyl hexanoic acid |
| WO2009087650A2 (en) * | 2007-10-15 | 2009-07-16 | V.B. Medicare Pvt. Ltd. | A novel process for synthesis of pregabalin from substituted cyclopropane intermediate and a process for enzymatic resolution of racemic pregabalin |
| EA019285B1 (ru) | 2008-05-21 | 2014-02-28 | Сандоз Аг | Способ стереоселективного ферментативного гидролиза эфира 5-метил-3-нитрометилгексановой кислоты |
| US8614081B2 (en) | 2009-07-23 | 2013-12-24 | Codexis, Inc. | Nitrilase biocatalysts |
| WO2011141923A2 (en) | 2010-05-14 | 2011-11-17 | Lupin Limited | Improved synthesis of optically pure (s) - 3-cyano-5-methyl-hexanoic acid alkyl ester, an intermediate of (s)- pregabalin |
| US8604062B2 (en) * | 2011-10-20 | 2013-12-10 | Hoffman-La Roche Inc. | Process for the preparation of isoxazolyl-methoxy nicotinic acids |
| JP6482465B2 (ja) * | 2012-11-07 | 2019-03-13 | ハイカル リミテッド | プレガバリンの調製方法 |
| 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 |
| CN105017072B (zh) * | 2015-06-30 | 2017-10-03 | 河北诚信有限责任公司 | 异丁基琥珀腈的合成方法 |
| CN105176955B (zh) | 2015-08-27 | 2018-11-02 | 浙江工业大学 | 来源于高山南芥的腈水解酶、基因、载体、工程菌及其应用 |
| CN108424900B (zh) * | 2018-02-09 | 2020-11-03 | 浙江工业大学 | 一种腈水解酶突变体及其构建方法和应用 |
| CN111100856B (zh) * | 2020-01-13 | 2021-12-07 | 浙江工业大学 | 腈水解酶突变体及在普瑞巴林手性中间体合成中的应用 |
| CN113651717B (zh) * | 2021-08-05 | 2024-08-30 | 浙江工业大学 | 一种光学纯异丁基丁二腈的消旋方法 |
| CN116041214B (zh) * | 2022-11-15 | 2025-04-22 | 奥锐特药业股份有限公司 | 一种普瑞巴林中间体的制备方法及其应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5593871A (en) * | 1990-09-20 | 1997-01-14 | E. I. Du Pont De Nemours And Company | Process for the preparation of enantiometric 2-alkanoic acid amides from nitriles |
| JP3218133B2 (ja) * | 1993-02-03 | 2001-10-15 | 三菱レイヨン株式会社 | フェニル基を有する光学活性α−ヒドロキシカルボン酸の製造法 |
| US5637767A (en) * | 1995-06-07 | 1997-06-10 | Warner-Lambert Company | Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| US5858736A (en) * | 1996-05-17 | 1999-01-12 | E. I. Du Pont De Nemours And Company | Preparation of lactams from aliphatic α,ω-dinitriles |
| DE69834204T2 (de) | 1997-10-27 | 2007-03-29 | Warner-Lambert Co. Llc | Zyklische aminosäuren und deren derivate als arzneimittel |
| US6642398B2 (en) | 1999-06-10 | 2003-11-04 | Warner-Lambert Company | Mono-and disubstituted 3-propyl gamma-aminobutyric acids |
| US6551804B2 (en) | 1999-07-12 | 2003-04-22 | E. I. Du Pont De Nemours And Company | Process for preparing 4-cyanopentanoic acid |
| US20040014195A1 (en) | 1999-12-29 | 2004-01-22 | Diversa Corporation | Nitrilases, nucleic acids encoding them and methods for making and using them |
| SK287303B6 (sk) | 2000-01-27 | 2010-06-07 | Warner-Lambert Company | Spôsob prípravy derivátu (S)-3-kyano-5-metyl-hexánovej kyseliny, spôsob a medziprodukt na prípravu pregabalínu |
| FR2824823A1 (fr) * | 2001-05-21 | 2002-11-22 | Aventis Animal Nutrition Sa | Procede de preparation d'acides carboxyliques aliphatiques par hydrolyse enzymatique de composes nitriles aliphatiques |
| WO2004111256A1 (en) * | 2003-06-19 | 2004-12-23 | Pfizer Products Inc. | Biocatalytic preparation of 1-cyanocyclohexaneacetic acid |
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2005
- 2005-01-04 UA UAA200610837A patent/UA82292C2/uk unknown
- 2005-04-01 AU AU2005233371A patent/AU2005233371B2/en not_active Ceased
- 2005-04-01 ES ES05718347T patent/ES2331140T3/es not_active Expired - Lifetime
- 2005-04-01 JP JP2007507859A patent/JP4051082B2/ja not_active Expired - Fee Related
- 2005-04-01 EP EP05718347A patent/EP1745136B1/en not_active Expired - Lifetime
- 2005-04-01 HR HR20090562T patent/HRP20090562T1/xx unknown
- 2005-04-01 CA CA2563307A patent/CA2563307C/en not_active Expired - Fee Related
- 2005-04-01 DK DK05718347T patent/DK1745136T3/da active
- 2005-04-01 EA EA200601574A patent/EA010305B1/ru not_active IP Right Cessation
- 2005-04-01 NZ NZ549698A patent/NZ549698A/en not_active IP Right Cessation
- 2005-04-01 BR BRPI0509908-0A patent/BRPI0509908A/pt not_active Application Discontinuation
- 2005-04-01 ME MEP-2009-320A patent/ME01107B/me unknown
- 2005-04-01 AP AP2006003764A patent/AP2301A/xx active
- 2005-04-01 RS RSP-2009/0451A patent/RS50994B/sr unknown
- 2005-04-01 AT AT05718347T patent/ATE445019T1/de active
- 2005-04-01 DO DO2005000055A patent/DOP2005000055A/es unknown
- 2005-04-01 PL PL05718347T patent/PL1745136T3/pl unknown
- 2005-04-01 PT PT05718347T patent/PT1745136E/pt unknown
- 2005-04-01 CN CN2005800109287A patent/CN1942587B/zh not_active Expired - Fee Related
- 2005-04-01 GE GEAP20059657A patent/GEP20084530B/en unknown
- 2005-04-01 DE DE602005017027T patent/DE602005017027D1/de not_active Expired - Lifetime
- 2005-04-01 US US10/599,899 patent/US7727749B2/en not_active Expired - Fee Related
- 2005-04-01 SI SI200530805T patent/SI1745136T1/sl unknown
- 2005-04-01 WO PCT/IB2005/000873 patent/WO2005100580A1/en not_active Ceased
- 2005-04-01 KR KR1020067021286A patent/KR100887777B1/ko not_active Expired - Fee Related
- 2005-04-12 PE PE2005000405A patent/PE20060252A1/es not_active Application Discontinuation
- 2005-04-12 UY UY28851A patent/UY28851A1/es not_active Application Discontinuation
- 2005-04-12 HN HN2005000162A patent/HN2005000162A/es unknown
- 2005-04-12 MY MYPI20051622A patent/MY144296A/en unknown
- 2005-04-12 AR ARP050101423A patent/AR048690A1/es not_active Application Discontinuation
- 2005-04-13 PA PA20058629801A patent/PA8629801A1/es unknown
- 2005-04-13 TW TW094111638A patent/TWI304095B/zh not_active IP Right Cessation
- 2005-04-13 GT GT200500086A patent/GT200500086A/es unknown
- 2005-04-13 NL NL1028762A patent/NL1028762C2/nl not_active IP Right Cessation
- 2005-04-14 SV SV2005002085A patent/SV2005002085A/es active IP Right Grant
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2006
- 2006-09-06 IL IL177918A patent/IL177918A/en not_active IP Right Cessation
- 2006-09-07 ZA ZA200607476A patent/ZA200607476B/en unknown
- 2006-10-10 EC EC2006006917A patent/ECSP066917A/es unknown
- 2006-10-12 CR CR8686A patent/CR8686A/es unknown
- 2006-10-13 TN TNP2006000329A patent/TNSN06329A1/fr unknown
- 2006-10-13 MA MA29391A patent/MA28536B1/fr unknown
- 2006-11-10 NO NO20065181A patent/NO335624B1/no not_active IP Right Cessation
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2009
- 2009-10-30 CY CY20091101131T patent/CY1109556T1/el unknown
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2010
- 2010-04-20 US US12/763,570 patent/US8304252B2/en not_active Expired - Fee Related
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2011
- 2011-06-22 CR CR20110356A patent/CR20110356A/es unknown
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