BRPI0608445A2 - processo para preparação de ácidos e-(2s)-alquil-5-halopent-enóicos enantiopuros e seus ésteres - Google Patents
processo para preparação de ácidos e-(2s)-alquil-5-halopent-enóicos enantiopuros e seus ésteresInfo
- Publication number
- BRPI0608445A2 BRPI0608445A2 BRPI0608445-1A BRPI0608445A BRPI0608445A2 BR PI0608445 A2 BRPI0608445 A2 BR PI0608445A2 BR PI0608445 A BRPI0608445 A BR PI0608445A BR PI0608445 A2 BRPI0608445 A2 BR PI0608445A2
- Authority
- BR
- Brazil
- Prior art keywords
- alkyl
- halopent
- esters
- preparation
- salt
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 5
- 150000002148 esters Chemical class 0.000 title abstract 4
- 150000007513 acids Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 3
- VDMAQVANUGNDOM-NSHDSACASA-N (2s)-3-methyl-2-phenylbutan-1-amine Chemical compound CC(C)[C@H](CN)C1=CC=CC=C1 VDMAQVANUGNDOM-NSHDSACASA-N 0.000 abstract 2
- 235000001258 Cinchona calisaya Nutrition 0.000 abstract 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 abstract 2
- 229960000948 quinine Drugs 0.000 abstract 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PROCESSO PARA PREPARAçãO DE áCIDOS E-(2S)-ALQUIL-5-HALOPENT-ENóICOS ENANTIOPUROS E SEUS éSTERES. Processo para preparação de ácidos E-(2S)-alquil-5-halopent-4-enóicos enantiopuros e seus ésteres da fórmula (I). onde R é um radical alquila C~ 1~-C~ 6~, R~ 1~ é H ou alquila C~ 1~-C~ 4~ e X é cloro, bromo ou iodo, onde o ácido 2-alquil-5-halopent-4-enóico correspondente: a) é reagido em um primeiro solvente apropriado com (S)-3-metil-2-fenilbutilamina, quinina ou com N-metil-D-glucamina, após o que b) o sal de (S)-3-metil-2-fenilbutilamina, sal de quinina ou de glucamina correspondente do ácido (R) - pentenóico é precipitado e removido, e c) o filtrado remanescente é misturado com uma segunda base quiral ou um sal inorgânico, após o que o sal correspondente do ácido (S)-pentenóico é precipitado, e d) é então convertido no ácido E-(2S)-alquil-5- halopent-4-enóico correspondente e subseqúentemente, quando apropriado, no éster correspondente da fórmula (1), onde R~ 1~ é alquila C~ 1~-C~ 4~
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT4002005 | 2005-03-09 | ||
| PCT/EP2006/001597 WO2006099926A1 (en) | 2005-03-09 | 2006-02-22 | Process for preparing enantiopure e-(2s)-alkyl-5-halopent-4-enoic acids and esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0608445A2 true BRPI0608445A2 (pt) | 2009-12-29 |
Family
ID=36072408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0608445-1A BRPI0608445A2 (pt) | 2005-03-09 | 2006-02-22 | processo para preparação de ácidos e-(2s)-alquil-5-halopent-enóicos enantiopuros e seus ésteres |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20080281125A1 (pt) |
| EP (1) | EP1856008A1 (pt) |
| JP (1) | JP2008536810A (pt) |
| KR (1) | KR20070110510A (pt) |
| CN (1) | CN101137602A (pt) |
| BR (1) | BRPI0608445A2 (pt) |
| CA (1) | CA2599409A1 (pt) |
| EA (1) | EA200701925A1 (pt) |
| IL (1) | IL185636A0 (pt) |
| MX (1) | MX2007011006A (pt) |
| WO (1) | WO2006099926A1 (pt) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5182615B2 (ja) * | 2005-12-16 | 2013-04-17 | 旭硝子株式会社 | 光学活性な（４ｅ）−５−クロロ−２−イソプロピル−４−ペンテン酸またはその塩基性アミノ酸塩の製造方法 |
| CN104524543A (zh) * | 2014-12-28 | 2015-04-22 | 白玲强 | 一种含依那普利的抗高血压药物组合物及用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1200390T3 (da) * | 1999-07-29 | 2008-12-01 | Speedel Pharma Ag | Fremstilling af N-substituerede 2,7-dialkyl-4-hydroxy-5-amino-8-aryl-octanoylamider |
| CA2445014C (en) * | 2001-05-15 | 2011-10-11 | Speedel Pharma Ag | Process for the preparation of substituted carboxylic acid esters by enzymatic hydrolysis |
| DE60312214T3 (de) * | 2002-12-09 | 2015-02-26 | Asahi Glass Co., Ltd. | Verfahren zur herstellung von(4e)-5-chloro-2-isopropyl-4-pentensäureester und optischaktivem isomer davon |
-
2006
- 2006-02-22 BR BRPI0608445-1A patent/BRPI0608445A2/pt not_active IP Right Cessation
- 2006-02-22 CN CNA2006800077083A patent/CN101137602A/zh active Pending
- 2006-02-22 MX MX2007011006A patent/MX2007011006A/es not_active Application Discontinuation
- 2006-02-22 CA CA002599409A patent/CA2599409A1/en not_active Abandoned
- 2006-02-22 WO PCT/EP2006/001597 patent/WO2006099926A1/en not_active Ceased
- 2006-02-22 JP JP2008500069A patent/JP2008536810A/ja not_active Withdrawn
- 2006-02-22 EP EP06707162A patent/EP1856008A1/en not_active Withdrawn
- 2006-02-22 US US11/885,740 patent/US20080281125A1/en not_active Abandoned
- 2006-02-22 KR KR1020077020450A patent/KR20070110510A/ko not_active Withdrawn
- 2006-02-22 EA EA200701925A patent/EA200701925A1/ru unknown
-
2007
- 2007-08-30 IL IL185636A patent/IL185636A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008536810A (ja) | 2008-09-11 |
| EA200701925A1 (ru) | 2008-02-28 |
| EP1856008A1 (en) | 2007-11-21 |
| CA2599409A1 (en) | 2006-09-28 |
| IL185636A0 (en) | 2008-01-06 |
| KR20070110510A (ko) | 2007-11-19 |
| MX2007011006A (es) | 2007-11-08 |
| WO2006099926A1 (en) | 2006-09-28 |
| US20080281125A1 (en) | 2008-11-13 |
| CN101137602A (zh) | 2008-03-05 |
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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 AS 5A E 6A ANUIDADES. |
|
| 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 8.6 PUBLICADO NA RPI 2161 DE 05/06/2012. |