BRPI0803092A2 - sìntese de (s)-(+)-3-(aminometil)-5-metil ácido hexanóico, (s)-pregabalina - Google Patents
sìntese de (s)-(+)-3-(aminometil)-5-metil ácido hexanóico, (s)-pregabalina Download PDFInfo
- Publication number
- BRPI0803092A2 BRPI0803092A2 BRPI0803092-8A BRPI0803092A BRPI0803092A2 BR PI0803092 A2 BRPI0803092 A2 BR PI0803092A2 BR PI0803092 A BRPI0803092 A BR PI0803092A BR PI0803092 A2 BRPI0803092 A2 BR PI0803092A2
- Authority
- BR
- Brazil
- Prior art keywords
- aminomethyl
- synthesis
- pregabalin
- hexanoic acid
- methyl hexanoic
- Prior art date
Links
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 title abstract 4
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 229960001233 pregabalin Drugs 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- AYXYPKUFHZROOJ-UHFFFAOYSA-N 3-(azaniumylmethyl)-5-methylhexanoate Chemical compound CC(C)CC(CN)CC(O)=O AYXYPKUFHZROOJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SìNTESE DE (S)-(+)-3-(AMINOMETIL)-5-METIL áCIDO HEXANóICO, (S)-PREGABALINA. A invenção abrange a síntese de (S)-(+)-3-(aminometil)-5-ácido metilhexanóico, (S)-pregabalina, via um quiral intermediário da seguinte fórmula 4 em que Ar é um grupo aromático C~6-10~, R é um alquil, éster, ou ácido carboxilico C~1-4~ direto ou ramificado, e R~1~ é um alquil, araiquil, ou aralquil substituído C~1-5~ direto ou ramificado.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91957507P | 2007-03-22 | 2007-03-22 | |
| US93231707P | 2007-05-29 | 2007-05-29 | |
| PCT/US2008/003898 WO2008118427A2 (en) | 2007-03-22 | 2008-03-24 | Synthesis of (s)-(+)-3-(aminomethyl)-5-methyl hexanoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0803092A2 true BRPI0803092A2 (pt) | 2011-08-30 |
Family
ID=39567149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0803092-8A BRPI0803092A2 (pt) | 2007-03-22 | 2008-03-24 | sìntese de (s)-(+)-3-(aminometil)-5-metil ácido hexanóico, (s)-pregabalina |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8097754B2 (pt) |
| EP (1) | EP2021318A2 (pt) |
| KR (1) | KR101036536B1 (pt) |
| BR (1) | BRPI0803092A2 (pt) |
| CA (1) | CA2681313C (pt) |
| MX (1) | MX2008014759A (pt) |
| TW (1) | TW200846308A (pt) |
| WO (1) | WO2008118427A2 (pt) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2619472A1 (en) | 2005-09-19 | 2007-03-29 | Teva Pharmaceutical Industries Ltd. | Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key intermediates for the new synthesis of (s)-pregabalin |
| KR101036536B1 (ko) | 2007-03-22 | 2011-05-24 | 테바 파마슈티컬 인더스트리즈 리미티드 | (s)-(+)-3-(아미노메틸)-5-메틸 헥산산의 합성 |
| US20110245536A1 (en) * | 2008-06-02 | 2011-10-06 | Actavis Group Ptc Ehf | Process for preparing pregabalin |
| WO2011086565A1 (en) * | 2010-01-15 | 2011-07-21 | Lupin Limited | Method for preparation of enantiomerically enriched and/or racemic gamma-amino 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 |
| WO2017019791A1 (en) | 2015-07-27 | 2017-02-02 | Teva Pharmaceuticals International Gmbh | Synthesis of (s)-pregabalin |
| BR112018070480A2 (pt) * | 2016-04-06 | 2019-01-29 | Rhodia Operations | composto da fórmula, processo para fabricar o composto da fórmula, mistura, uso do composto da fórmula, e, composição em gel |
| CN108456143A (zh) * | 2017-02-22 | 2018-08-28 | 尚科生物医药(上海)有限公司 | 不对称制备(s)-3-氨甲基-5-甲基己酸 |
| EP3466398A1 (en) | 2017-10-05 | 2019-04-10 | Rhodia Operations | N-hydrocarbyldiamide composition with gelating properties |
| CN116554062A (zh) * | 2021-10-08 | 2023-08-08 | 浙江华海药业股份有限公司 | 一种普瑞巴林中间体杂质化合物ii及其制备方法 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2053582T3 (es) | 1986-08-13 | 1994-08-01 | Ciba Geigy Ag | Procedimiento para la obtencion de derivados del acido 5-amino-4-hidroxivalerianico. |
| US6197819B1 (en) | 1990-11-27 | 2001-03-06 | Northwestern University | Gamma amino butyric acid analogs and optical isomers |
| US5616793A (en) | 1995-06-02 | 1997-04-01 | Warner-Lambert Company | Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| US5637767A (en) | 1995-06-07 | 1997-06-10 | Warner-Lambert Company | Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| DE19530637A1 (de) | 1995-08-21 | 1997-02-27 | Bayer Ag | Verfahren zur Herstellung von 2,2-Difluorbenzo[1.3]dioxolcarbaldehyden |
| NZ332762A (en) | 1996-07-24 | 2000-09-29 | Warner Lambert Co | Isobutylgaba and its derivatives for the treatment of pain |
| GB9812413D0 (en) | 1998-06-10 | 1998-08-05 | Glaxo Group Ltd | Compound and its use |
| FR2781793B1 (fr) | 1998-08-03 | 2001-07-20 | Prographarm Lab | Procede de fabrication de granules de gabapentine enrobes |
| US6642398B2 (en) | 1999-06-10 | 2003-11-04 | Warner-Lambert Company | Mono-and disubstituted 3-propyl gamma-aminobutyric acids |
| ME00921B (me) | 2000-01-27 | 2012-06-20 | Warner Lambert Co | Asimetrična sinteza pregabalina |
| WO2001074741A2 (en) | 2000-04-04 | 2001-10-11 | Brandeis University | Catalytic asymmetric desymmetrization of meso compounds |
| US6833458B2 (en) | 2000-06-05 | 2004-12-21 | Development Center For Biotechnology | Practical syntheses of chiral trans-3, 4-disubstituted piperidines and the intermediates |
| DE10203122A1 (de) | 2002-01-25 | 2003-07-31 | Gruenenthal Gmbh | Verfahren zur Herstellung von substituierten Acrylsäureestern bzw. deren Einsatz zur Herstellung von substituierten gamma-Aminosäuren |
| US20030225149A1 (en) | 2002-04-30 | 2003-12-04 | Blazecka Peter G. | Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids |
| ATE371496T1 (de) | 2004-03-12 | 2007-09-15 | Warner Lambert Co | C1-symmetrische bisphosphinliganden und deren verwendung bei der asymmetrischen synthese von pregabalin |
| EP1735324B1 (en) | 2004-04-01 | 2008-08-20 | Warner-Lambert Company LLC | Preparation of p-chirogenic phospholanes and their use in asymetric synthesis |
| UA82292C2 (uk) | 2004-04-14 | 2008-03-25 | Пфайзер Продактс Инк. | Спосіб стереоселективного біоперетворення аліфатичних динітрилів в ціанокарбонові кислоти (варіанти) |
| CN102102114B (zh) | 2004-06-21 | 2013-08-14 | 沃尼尔·朗伯有限责任公司 | 普瑞巴林和相关化合物的制备 |
| WO2006008640A1 (en) | 2004-07-15 | 2006-01-26 | Pharmacia & Upjohn Company Llc | Non-aqueous suspension containing a drug having an unpleasant taste |
| CN1634869A (zh) | 2004-12-06 | 2005-07-06 | 北京阜康仁生物制药科技有限公司 | 普瑞巴林新晶型及其制备方法 |
| MX2007012606A (es) | 2005-04-11 | 2008-01-11 | Teva Pharma | Proceso para elaborar (s)-pregabalina. |
| US7462737B2 (en) | 2005-05-10 | 2008-12-09 | Teva Pharmaceutical Industries Ltd. | Pregabalin free of isobutylglutaric acid and a process for preparation thereof |
| CA2604602A1 (en) | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Method for the preparation of pregabalin and salts thereof |
| US20060270871A1 (en) | 2005-05-30 | 2006-11-30 | Khanduri Chandra H | Polymorphic form i of pregabalin and processes for its preparation |
| CN100410242C (zh) | 2005-06-23 | 2008-08-13 | 江苏恩华药业股份有限公司 | 普瑞巴林中间体及其制备方法 |
| CZ297970B6 (cs) | 2005-08-10 | 2007-05-09 | Zentiva, A. S | Zpusob výroby (S)-3-(aminomethyl)-5-methyl-hexanové kyseliny (pregabalinu) |
| CA2619472A1 (en) | 2005-09-19 | 2007-03-29 | Teva Pharmaceutical Industries Ltd. | Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key intermediates for the new synthesis of (s)-pregabalin |
| 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 |
| ITMI20061297A1 (it) | 2006-07-04 | 2008-01-05 | Laboratorio Chimico Int Spa | Procedimento per la preparazione della'acido (r)-(-)-3-(carbamoilmetil)-5-metilesanoico e del pregabalin e intermedi di sintesi |
| WO2008007145A2 (en) | 2006-07-12 | 2008-01-17 | Generics [Uk] Limited | Process of preparing a gamma-amino acid |
| GB0614133D0 (en) | 2006-07-15 | 2006-08-23 | Pliva Istrazivanje I Razvoj D | Process for preparing a pharmaceutical compound |
| US20080014280A1 (en) | 2006-07-17 | 2008-01-17 | Glenmark Pharmaceuticals Limited | Amorphous pregabalin and process for the preparation thereof |
| KR101036536B1 (ko) | 2007-03-22 | 2011-05-24 | 테바 파마슈티컬 인더스트리즈 리미티드 | (s)-(+)-3-(아미노메틸)-5-메틸 헥산산의 합성 |
| EP1992609A1 (en) | 2007-05-14 | 2008-11-19 | Dipharma Francis S.r.l. | A process for the preparation of a (S)(+)-3-(aminomethyl)-5-methylhexanoic acid |
| EP2017273A1 (en) | 2007-07-18 | 2009-01-21 | Laboratorios del Dr. Esteve S.A. | Process for the enantioselective preparation of pregabalin |
| ITMI20072262A1 (it) | 2007-12-03 | 2009-06-04 | Dipharma Francis Srl | Procedimento per la preparazione di acido (s)(+)-3-(amminometil)-5-metilesanoico |
-
2008
- 2008-03-24 KR KR1020087028593A patent/KR101036536B1/ko not_active Expired - Fee Related
- 2008-03-24 CA CA2681313A patent/CA2681313C/en not_active Expired - Fee Related
- 2008-03-24 MX MX2008014759A patent/MX2008014759A/es unknown
- 2008-03-24 BR BRPI0803092-8A patent/BRPI0803092A2/pt not_active IP Right Cessation
- 2008-03-24 TW TW097110392A patent/TW200846308A/zh unknown
- 2008-03-24 US US12/079,225 patent/US8097754B2/en not_active Expired - Fee Related
- 2008-03-24 WO PCT/US2008/003898 patent/WO2008118427A2/en not_active Ceased
- 2008-03-24 EP EP08742247A patent/EP2021318A2/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008118427A3 (en) | 2008-12-18 |
| CA2681313A1 (en) | 2008-10-02 |
| US8097754B2 (en) | 2012-01-17 |
| EP2021318A2 (en) | 2009-02-11 |
| WO2008118427A9 (en) | 2009-02-05 |
| KR101036536B1 (ko) | 2011-05-24 |
| TW200846308A (en) | 2008-12-01 |
| MX2008014759A (es) | 2009-03-09 |
| KR20090010075A (ko) | 2009-01-28 |
| US20080306292A1 (en) | 2008-12-11 |
| WO2008118427A2 (en) | 2008-10-02 |
| CA2681313C (en) | 2012-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BRPI0803092A2 (pt) | sìntese de (s)-(+)-3-(aminometil)-5-metil ácido hexanóico, (s)-pregabalina | |
| MA31831B1 (fr) | Inhibiteurs de protéase époxy-cétone peptidique cristalline, et synthèse de céto-époxydes d'acides aminés | |
| BR112014024157A2 (pt) | Composição comestível, solução de estoque e método para complementar as características de sabor ou paladar de produtos comestíveis | |
| GEP20146169B (en) | N1-pyrazolospiroketone acetyl-coa carboxylase inhibitors | |
| WO2009117987A3 (de) | Verwendung von boswelliasäuren und synthetischen boswelliasäurederivaten zur hemmung der mikrosomalen prostaglandin e2 synthase und des cathepsin g | |
| UA102817C2 (ru) | Способ синтеза агомелатина | |
| MX340125B (es) | 2-hidroxi-4-(metiltio) butironitrilo estable en almacenamiento. | |
| WO2008036967A3 (en) | Novel heterocyclic compounds as lasy activators | |
| BRPI0419067A (pt) | método para aumento da cognição utilizando ziprasidona | |
| WO2007127377A8 (en) | Combinations comprising omega-3 fatty acid compounds for the treatment of cardiovascular disease | |
| WO2008071928A3 (en) | Corrosion inhibitor intensifier compositions and associated methods | |
| MY148953A (en) | Substituted biphenyl carboxylic acids and derivatives thereof | |
| MA33069B1 (fr) | Dérivés de thiadiazoles et d'oxadiazoles, leur préparation et leur application en thérapeutique | |
| BR112013028486A2 (pt) | método para promover crescimento de planta | |
| UA107592C2 (uk) | Композиція для боротьби з захворюваннями рослин і її застосування | |
| EA200701810A1 (ru) | Производное изоксазолина и новый способ его получения | |
| EA200600878A1 (ru) | Производные феноксиуксусных кислот, применимые в качестве двойных агонистов активируемого пероксисомным пролифератором рецептора ( ppar ) | |
| MY137277A (en) | Pharmaceutically useful salts of carboxylic acid derivates | |
| BRPI0607093A2 (pt) | polimorfo cristalino de monoidrato de sal monossódico de ácido 3-(n-metil-n-pentil)amino-1-hidroxipropano-1, 1-difosfÈnico, ibandronato, processo para a preparação de um polimorfo de ibandronato cristalino, e composição farmacêutica que o compreende | |
| CY1111730T1 (el) | Διαδικασια για την παρασκευη γκαμπαπεντινης | |
| BR112012006397A2 (pt) | composição de inibidor de corrosão, e, método. | |
| BR0300673A (pt) | Método para aprimorar o clareamento da pele | |
| BRPI0814115B8 (pt) | composição farmacêutica compreendendo o composto 11-deóxi-prostaglandina e método para estabilizar o composto | |
| DE602006008962D1 (de) | Verfahren zur herstellung von valsartan | |
| MX2010006995A (es) | 3-n-fenil-1,3,4-oxadiazolonas sustituidas con 5-o para uso medico. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE A 4A ANUIDADE. |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: REFERENTE AO DESPACHO PUBLICADO NA RPI 2162 12/06/2012. |