CN105051022B - 用于制备普瑞巴林的方法和中间体 - Google Patents
用于制备普瑞巴林的方法和中间体 Download PDFInfo
- Publication number
- CN105051022B CN105051022B CN201480018083.5A CN201480018083A CN105051022B CN 105051022 B CN105051022 B CN 105051022B CN 201480018083 A CN201480018083 A CN 201480018083A CN 105051022 B CN105051022 B CN 105051022B
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- Prior art keywords
- acid
- reaction
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- Expired - Fee Related
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- 0 CC(*)C=C(C1)[C@@](*)(CO)OC1=O Chemical compound CC(*)C=C(C1)[C@@](*)(CO)OC1=O 0.000 description 3
- FNEOZWRFOAPNGO-UHFFFAOYSA-N CC(C)=CC(C(O)O1)=CC1=O Chemical compound CC(C)=CC(C(O)O1)=CC1=O FNEOZWRFOAPNGO-UHFFFAOYSA-N 0.000 description 2
- AZEDQMIQBQTMOQ-FNORWQNLSA-N CC(C)=C/C=C/N(C)C Chemical compound CC(C)=C/C=C/N(C)C AZEDQMIQBQTMOQ-FNORWQNLSA-N 0.000 description 1
- MVKIPKIHASYTSN-UHFFFAOYSA-N CC(C)=CC(C(N(C)C)O1)=CC1=O Chemical compound CC(C)=CC(C(N(C)C)O1)=CC1=O MVKIPKIHASYTSN-UHFFFAOYSA-N 0.000 description 1
- XDAHUMVEWMOROU-UHFFFAOYSA-N CC(C)CC(C1)C(O)[U]C1=O Chemical compound CC(C)CC(C1)C(O)[U]C1=O XDAHUMVEWMOROU-UHFFFAOYSA-N 0.000 description 1
- AYXYPKUFHZROOJ-UHFFFAOYSA-N CC(C)CC(CC(O)=O)CN Chemical compound CC(C)CC(CC(O)=O)CN AYXYPKUFHZROOJ-UHFFFAOYSA-N 0.000 description 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N CC(C)C[C@@H](CC(O)=O)CN Chemical compound CC(C)C[C@@H](CC(O)=O)CN AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 1
- NOOLISFMXDJSKH-ZDGBYWQASA-N CC(C)[C@H](CC[C@@H](C)C1)C1O Chemical compound CC(C)[C@H](CC[C@@H](C)C1)C1O NOOLISFMXDJSKH-ZDGBYWQASA-N 0.000 description 1
- JFPGYEOALSSKKC-FBKFWFMHSA-N CC(C)[C@H]1C(C)C[C@H](C)CC1 Chemical compound CC(C)[C@H]1C(C)C[C@H](C)CC1 JFPGYEOALSSKKC-FBKFWFMHSA-N 0.000 description 1
- BQWXQEDJNDGBOJ-NETXQHHPSA-N CC([C@@](C)(CC(O)=O)CN)C=C Chemical compound CC([C@@](C)(CC(O)=O)CN)C=C BQWXQEDJNDGBOJ-NETXQHHPSA-N 0.000 description 1
Classifications
-
- 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
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- 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
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- 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
- C07C227/12—Formation of amino and carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/74—Unsaturated compounds containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/1096—Transferases (2.) transferring nitrogenous groups (2.6)
-
- 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
- C12P13/005—Amino acids other than alpha- or beta amino acids, e.g. gamma amino 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
-
- 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
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Steroid Compounds (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710882505.9A CN107556273A (zh) | 2013-03-27 | 2014-03-25 | 用于制备普瑞巴林的方法和中间体 |
| CN201710882572.0A CN107746834A (zh) | 2013-03-27 | 2014-03-25 | 用于制备普瑞巴林的方法和中间体 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361805786P | 2013-03-27 | 2013-03-27 | |
| US61/805,786 | 2013-03-27 | ||
| PCT/IB2014/060140 WO2014155291A1 (en) | 2013-03-27 | 2014-03-25 | Process and intermediates for the preparation of pregabalin |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710882572.0A Division CN107746834A (zh) | 2013-03-27 | 2014-03-25 | 用于制备普瑞巴林的方法和中间体 |
| CN201710882505.9A Division CN107556273A (zh) | 2013-03-27 | 2014-03-25 | 用于制备普瑞巴林的方法和中间体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105051022A CN105051022A (zh) | 2015-11-11 |
| CN105051022B true CN105051022B (zh) | 2017-10-27 |
Family
ID=50483187
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480018083.5A Expired - Fee Related CN105051022B (zh) | 2013-03-27 | 2014-03-25 | 用于制备普瑞巴林的方法和中间体 |
| CN201710882505.9A Pending CN107556273A (zh) | 2013-03-27 | 2014-03-25 | 用于制备普瑞巴林的方法和中间体 |
| CN201710882572.0A Pending CN107746834A (zh) | 2013-03-27 | 2014-03-25 | 用于制备普瑞巴林的方法和中间体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710882505.9A Pending CN107556273A (zh) | 2013-03-27 | 2014-03-25 | 用于制备普瑞巴林的方法和中间体 |
| CN201710882572.0A Pending CN107746834A (zh) | 2013-03-27 | 2014-03-25 | 用于制备普瑞巴林的方法和中间体 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20160024540A1 (enExample) |
| EP (2) | EP3216863A1 (enExample) |
| JP (1) | JP2016516744A (enExample) |
| KR (1) | KR20150121202A (enExample) |
| CN (3) | CN105051022B (enExample) |
| AU (2) | AU2014240833B2 (enExample) |
| BR (2) | BR112015024859A2 (enExample) |
| CA (1) | CA2905411A1 (enExample) |
| CY (1) | CY1118945T1 (enExample) |
| DK (1) | DK2978748T3 (enExample) |
| ES (1) | ES2630128T3 (enExample) |
| HU (1) | HUE034834T2 (enExample) |
| IL (1) | IL241438A0 (enExample) |
| MX (1) | MX2015013589A (enExample) |
| PL (1) | PL2978748T3 (enExample) |
| PT (1) | PT2978748T (enExample) |
| RU (2) | RU2017125261A (enExample) |
| SG (1) | SG11201506998XA (enExample) |
| SI (1) | SI2978748T1 (enExample) |
| WO (1) | WO2014155291A1 (enExample) |
| ZA (1) | ZA201506798B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102341494B (zh) | 2009-01-08 | 2014-10-15 | 科德克希思公司 | 转氨酶多肽 |
| 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 |
| WO2016140799A1 (en) * | 2015-03-03 | 2016-09-09 | Ark Diagnostics, Inc. | Pregabalin immunoassays |
| CA3064574A1 (en) | 2017-06-14 | 2018-12-20 | Codexis, Inc. | Engineered transaminase polypeptides for industrial biocatalysis |
| MX2021000278A (es) | 2018-07-09 | 2021-03-31 | Merck Sharp & Dohme Llc | Sintesis enzimatica de analogos de nucleosido de 4'-etinilo. |
| CN111004102B (zh) * | 2019-12-23 | 2022-11-04 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法及用于该方法的催化剂 |
| CN118772033A (zh) * | 2024-06-11 | 2024-10-15 | 中国科学院成都生物研究所 | 一种普瑞巴林三聚体的合成方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1649827A (zh) * | 2002-04-30 | 2005-08-03 | 沃尼尔·朗伯有限责任公司 | 高度官能化γ－丁内酰胺和γ－氨基酸的制备方法 |
| WO2008127646A2 (en) * | 2007-04-11 | 2008-10-23 | Dsm Ip Assets B.V. | Transaminase-based processes for preparation of pregabalin |
| CN102341494A (zh) * | 2009-01-08 | 2012-02-01 | 科德克希思公司 | 转氨酶多肽 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB834100A (en) | 1957-10-26 | 1960-05-04 | Eastman Kodak Co | Improvements in the preparation of mixed aldols |
| US4239636A (en) * | 1978-10-23 | 1980-12-16 | Exxon Research & Engineering Co. | Thio-bis-(alkyl lactone acid esters) and thio-bis-(hydrocarbyl diacid esters) are useful additives for lubricating compositions |
| US6197819B1 (en) | 1990-11-27 | 2001-03-06 | Northwestern University | Gamma amino butyric acid analogs and optical isomers |
| JPH06107597A (ja) * | 1992-03-12 | 1994-04-19 | Noguchi Kenkyusho | （Ｒ）−α−ヒドロキシ−β，γ−不飽和エステルの製造法 |
| US5268387A (en) * | 1992-04-24 | 1993-12-07 | Allergan, Inc. | Pharmaceutical compositions and method for administering 3 and 4-substituted 2(5H)-furanones to a mammal for inhibiting bone loss |
| CN1106411C (zh) * | 1995-11-07 | 2003-04-23 | 美国3M公司 | 引发剂系统和由其制成的粘合剂组合物 |
| KR100491282B1 (ko) | 1996-07-24 | 2005-05-24 | 워너-램버트 캄파니 엘엘씨 | 통증 치료용 이소부틸가바 및 그의 유도체 |
| SE9801992D0 (sv) * | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl-2-hydroxypropionic acid derivative I |
| MX2007012606A (es) * | 2005-04-11 | 2008-01-11 | Teva Pharma | Proceso para elaborar (s)-pregabalina. |
| CA2618057A1 (en) * | 2005-08-11 | 2007-02-22 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| KR100846419B1 (ko) * | 2007-08-10 | 2008-07-15 | 한국과학기술원 | 프레가발린의 신규한 제조 방법 |
| CN101362696A (zh) * | 2008-09-27 | 2009-02-11 | 开原亨泰精细化工厂 | 3-氨甲基-5-甲基己酸即混旋普瑞巴林的制备新方法 |
| WO2011086565A1 (en) | 2010-01-15 | 2011-07-21 | Lupin Limited | Method for preparation of enantiomerically enriched and/or racemic gamma-amino acids |
-
2014
- 2014-03-25 ES ES14717080.7T patent/ES2630128T3/es active Active
- 2014-03-25 SI SI201430236A patent/SI2978748T1/sl unknown
- 2014-03-25 CA CA2905411A patent/CA2905411A1/en not_active Abandoned
- 2014-03-25 AU AU2014240833A patent/AU2014240833B2/en not_active Ceased
- 2014-03-25 CN CN201480018083.5A patent/CN105051022B/zh not_active Expired - Fee Related
- 2014-03-25 HU HUE14717080A patent/HUE034834T2/en unknown
- 2014-03-25 RU RU2017125261A patent/RU2017125261A/ru not_active Application Discontinuation
- 2014-03-25 PL PL14717080T patent/PL2978748T3/pl unknown
- 2014-03-25 US US14/775,979 patent/US20160024540A1/en not_active Abandoned
- 2014-03-25 BR BR112015024859A patent/BR112015024859A2/pt not_active IP Right Cessation
- 2014-03-25 JP JP2016504807A patent/JP2016516744A/ja active Pending
- 2014-03-25 DK DK14717080.7T patent/DK2978748T3/en active
- 2014-03-25 CN CN201710882505.9A patent/CN107556273A/zh active Pending
- 2014-03-25 MX MX2015013589A patent/MX2015013589A/es unknown
- 2014-03-25 KR KR1020157026688A patent/KR20150121202A/ko not_active Abandoned
- 2014-03-25 PT PT147170807T patent/PT2978748T/pt unknown
- 2014-03-25 EP EP17162642.7A patent/EP3216863A1/en not_active Withdrawn
- 2014-03-25 BR BR122017006144A patent/BR122017006144A2/pt not_active IP Right Cessation
- 2014-03-25 SG SG11201506998XA patent/SG11201506998XA/en unknown
- 2014-03-25 WO PCT/IB2014/060140 patent/WO2014155291A1/en not_active Ceased
- 2014-03-25 EP EP14717080.7A patent/EP2978748B1/en not_active Not-in-force
- 2014-03-25 RU RU2015138545A patent/RU2628298C2/ru not_active IP Right Cessation
- 2014-03-25 CN CN201710882572.0A patent/CN107746834A/zh active Pending
-
2015
- 2015-09-10 IL IL241438A patent/IL241438A0/en unknown
- 2015-09-14 ZA ZA2015/06798A patent/ZA201506798B/en unknown
-
2016
- 2016-06-07 AU AU2016203782A patent/AU2016203782B2/en not_active Ceased
-
2017
- 2017-06-13 CY CY20171100622T patent/CY1118945T1/el unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1649827A (zh) * | 2002-04-30 | 2005-08-03 | 沃尼尔·朗伯有限责任公司 | 高度官能化γ－丁内酰胺和γ－氨基酸的制备方法 |
| WO2008127646A2 (en) * | 2007-04-11 | 2008-10-23 | Dsm Ip Assets B.V. | Transaminase-based processes for preparation of pregabalin |
| CN102341494A (zh) * | 2009-01-08 | 2012-02-01 | 科德克希思公司 | 转氨酶多肽 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR112015024859A2 (pt) | 2017-10-10 |
| CN107746834A (zh) | 2018-03-02 |
| CN105051022A (zh) | 2015-11-11 |
| MX2015013589A (es) | 2016-06-23 |
| CA2905411A1 (en) | 2014-10-02 |
| JP2016516744A (ja) | 2016-06-09 |
| CN107556273A (zh) | 2018-01-09 |
| EP2978748B1 (en) | 2017-05-10 |
| EP2978748A1 (en) | 2016-02-03 |
| AU2016203782B2 (en) | 2017-06-01 |
| CY1118945T1 (el) | 2018-01-10 |
| RU2017125261A (ru) | 2019-01-31 |
| KR20150121202A (ko) | 2015-10-28 |
| DK2978748T3 (en) | 2017-07-24 |
| IL241438A0 (en) | 2015-11-30 |
| EP3216863A1 (en) | 2017-09-13 |
| AU2014240833B2 (en) | 2016-07-07 |
| ZA201506798B (en) | 2019-05-29 |
| BR122017006144A2 (pt) | 2019-09-03 |
| SG11201506998XA (en) | 2015-10-29 |
| PL2978748T3 (pl) | 2017-09-29 |
| ES2630128T3 (es) | 2017-08-18 |
| RU2628298C2 (ru) | 2017-08-15 |
| RU2015138545A (ru) | 2017-05-03 |
| HUE034834T2 (en) | 2018-03-28 |
| AU2016203782A1 (en) | 2016-06-23 |
| HK1213882A1 (zh) | 2016-07-15 |
| SI2978748T1 (sl) | 2017-07-31 |
| AU2014240833A1 (en) | 2015-10-01 |
| PT2978748T (pt) | 2017-07-06 |
| WO2014155291A1 (en) | 2014-10-02 |
| US20160024540A1 (en) | 2016-01-28 |
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