ES2048653A1 - Proceso para la produccion de acido s-(+)-2-(3-benzoilfenil) propionico por transesterificacion enantioselectiva catalizada enzimaticamente en un disolvente organico. - Google Patents
Proceso para la produccion de acido s-(+)-2-(3-benzoilfenil) propionico por transesterificacion enantioselectiva catalizada enzimaticamente en un disolvente organico.Info
- Publication number
- ES2048653A1 ES2048653A1 ES9201190A ES9201190A ES2048653A1 ES 2048653 A1 ES2048653 A1 ES 2048653A1 ES 9201190 A ES9201190 A ES 9201190A ES 9201190 A ES9201190 A ES 9201190A ES 2048653 A1 ES2048653 A1 ES 2048653A1
- Authority
- ES
- Spain
- Prior art keywords
- opt
- ester
- benzoylphenyl
- propionic acid
- catalysed
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 150000002148 esters Chemical class 0.000 title abstract 7
- 238000005809 transesterification reaction Methods 0.000 title abstract 4
- 230000000707 stereoselective effect Effects 0.000 title abstract 3
- 102000004190 Enzymes Human genes 0.000 title abstract 2
- 108090000790 Enzymes Proteins 0.000 title abstract 2
- 230000007062 hydrolysis Effects 0.000 title abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 title abstract 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 title abstract 2
- 230000000813 microbial effect Effects 0.000 title abstract 2
- 229940121363 anti-inflammatory agent Drugs 0.000 title 1
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 229960000991 ketoprofen Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004122 cyclic group Chemical group 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 3
- 102000004882 Lipase Human genes 0.000 abstract 2
- 108090001060 Lipase Proteins 0.000 abstract 2
- 239000004367 Lipase Substances 0.000 abstract 2
- 235000019421 lipase Nutrition 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 abstract 1
- 102000013392 Carboxylesterase Human genes 0.000 abstract 1
- 108010051152 Carboxylesterase Proteins 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 241000235395 Mucor Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005233 alkylalcohol group Chemical group 0.000 abstract 1
- 230000001760 anti-analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000012074 organic phase Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PROCESO PARA LA PRODUCCION DE ACIDO S-(+)-2-(3-BENZOILFENIL) PROPIONICO POR TRANSESTERIFICACION ENANTIOSELECTIVA CATALIZADA ENZIMATICAMENTE EN UN DISOLVENTE ORGANICO. LA PRESENTE INVENCION CORRESPONDE A UN PROCEDIMIENTO PARA LA OBTENCION DEL ACIDO S-(+)-2-(3-BENZOILFENIL) PROPIONICO POR TRANSESTERIFICACION ESTEREOSELECTIVA CATALIZADA POR UNA LIPASA EN MEDIO ORGANICO, DEL ENANTIOMERO R DE UN ESTER ACTIVADO DEL ACIDO RACEMICO 2-(3-BENZOILFENIL) PROPIONICO CON UN ALCOHOL ALQUIRAL. LA MEZCLA DE ESTERES OBTENIDA SE SOMETE A UN TRATAMIENTO EN MEDIO ACUOSO ALCALINO DE FORMA QUE EL ESTER ACTIVADO REMANENTE SE HIDROLICE QUEMOSELECTIVAMENTE. EL S-ACIDO FINAL RESULTANTE Y EL R-ESTER SE SEPARAN POR EXTRACCION EN MEDIO BASICO CON UN DISOLVENTE ORGANICO INMISCIBLE EN AGUA, QUEDANDO EL ESTER EN LA FASE ORGANICA Y EN LA ACUOSA EL ACIDO S-(+)-2-(3-BENZOILFENIL) PROPIONICO OPTICAMENTE ACTIVO RESULTANTE. EL COMPUESTO DEL TITULO ASI COMO SUS SALES FARMACEUTICAMENTE ACEPTABLES TIENEN PROPIEDADES ANTI-INFLAMATORIAS Y ANALGESICAS.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9201190A ES2048653B1 (es) | 1992-06-08 | 1992-06-08 | Proceso para la produccion de acido s-(+)-2-(3-benzoilfenil) propionico por transesterificacion enantioselectiva catalizada enzimaticamente en un disolvente organico. |
| DE69316238T DE69316238D1 (de) | 1992-06-08 | 1993-05-26 | Verfahren zur herstellung von s-(+)-2-(-3benzoylphenyl)propionsäure durch enzym katalysierte enanthioselektieve umesterung in einem organischen lösungsmittel. |
| EP93912796A EP0672165B1 (en) | 1992-06-08 | 1993-05-26 | A process for the preparation of s-(+)-2-(3-benzoylphenyl)propionic acid by enzyme-catalysed enantioselective transesterification in an organic solvent |
| AU43182/93A AU4318293A (en) | 1992-06-08 | 1993-05-26 | A process for the preparation of s-(+)-2-(3-benzoylphenyl)propionic acid by enzyme-catalysed enantioselective transesterification in an organic solvent |
| PCT/EP1993/001322 WO1993025704A1 (en) | 1992-06-08 | 1993-05-26 | A process for the preparation of s-(+)-2-(3-benzoylphenyl)propionic acid by enzyme-catalysed enantioselective transesterification in an organic solvent |
| AT93912796T ATE161890T1 (de) | 1992-06-08 | 1993-05-26 | Verfahren zur herstellung von s-(+)-2-(- 3benzoylphenyl)propionsäure durch enzym katalysierte enanthioselektieve umesterung in einem organischen lösungsmittel. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9201190A ES2048653B1 (es) | 1992-06-08 | 1992-06-08 | Proceso para la produccion de acido s-(+)-2-(3-benzoilfenil) propionico por transesterificacion enantioselectiva catalizada enzimaticamente en un disolvente organico. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2048653A1 true ES2048653A1 (es) | 1994-03-16 |
| ES2048653B1 ES2048653B1 (es) | 1994-12-16 |
Family
ID=8277266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES9201190A Expired - Fee Related ES2048653B1 (es) | 1992-06-08 | 1992-06-08 | Proceso para la produccion de acido s-(+)-2-(3-benzoilfenil) propionico por transesterificacion enantioselectiva catalizada enzimaticamente en un disolvente organico. |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES2048653B1 (es) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0396447A1 (fr) * | 1989-05-02 | 1990-11-07 | Rhone-Poulenc Chimie | Procédé de séparation énantiomériquement sélective des esters des acides halogéno-2 propioniques |
| EP0407033A2 (en) * | 1989-06-05 | 1991-01-09 | Rhone-Poulenc Inc. | Lipase and isozymes, notably of Candida rugosa, and their use |
| EP0498706A1 (fr) * | 1991-02-08 | 1992-08-12 | Synthelabo | Procédé de préparation du (-)-(2R,3S)-2,3-époxy-3-(4-méthoxyphényl)propionate de méthyle |
| ES2033203A1 (es) * | 1990-05-17 | 1993-03-01 | Zambon Spa | Procedimiento para la preparacion de intermediarios utiles para la sintesis de benzotiacepinas. |
-
1992
- 1992-06-08 ES ES9201190A patent/ES2048653B1/es not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0396447A1 (fr) * | 1989-05-02 | 1990-11-07 | Rhone-Poulenc Chimie | Procédé de séparation énantiomériquement sélective des esters des acides halogéno-2 propioniques |
| EP0407033A2 (en) * | 1989-06-05 | 1991-01-09 | Rhone-Poulenc Inc. | Lipase and isozymes, notably of Candida rugosa, and their use |
| ES2033203A1 (es) * | 1990-05-17 | 1993-03-01 | Zambon Spa | Procedimiento para la preparacion de intermediarios utiles para la sintesis de benzotiacepinas. |
| EP0498706A1 (fr) * | 1991-02-08 | 1992-08-12 | Synthelabo | Procédé de préparation du (-)-(2R,3S)-2,3-époxy-3-(4-méthoxyphényl)propionate de méthyle |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2048653B1 (es) | 1994-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 20000401 |