ES2100037T3 - Proceso para preparar enantiomeros sustancialmente puros de acidos fenilpropionicos. - Google Patents
Proceso para preparar enantiomeros sustancialmente puros de acidos fenilpropionicos.Info
- Publication number
- ES2100037T3 ES2100037T3 ES94901940T ES94901940T ES2100037T3 ES 2100037 T3 ES2100037 T3 ES 2100037T3 ES 94901940 T ES94901940 T ES 94901940T ES 94901940 T ES94901940 T ES 94901940T ES 2100037 T3 ES2100037 T3 ES 2100037T3
- Authority
- ES
- Spain
- Prior art keywords
- pct
- stage
- date jun
- substantially pure
- pure enantiomers
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical compound C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 abstract 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 abstract 1
- 229960002390 flurbiprofen Drugs 0.000 abstract 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 abstract 1
- 229960001680 ibuprofen Drugs 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- 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
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
SE DESCRIBE UN PROCESO PARA LA PRODUCCION DE UN PRODUCTO QUE SE ENRIQUECE EN UN ENANTIOMERO DESEADO DE UN ACIDO FENILPROPIONICO SELECCIONADO DE IBUPROFENO Y FLURBIPROFENO, O SUS SALES ACEPTADAS FARMACEUTICAMENTE, QUE COMPRENDE LAS SIGUIENTES ETAPAS: (A) UNA ETAPA DE RESOLUCION, EN LA CUAL UNA SAL DE (OMEGA)METILOBENCILAMINA DEL ACIDO FENILPROPIONICO ES PREPARADA LA CUAL ES ENRIQUECIDA EN EL ENANTIOMERO DESEADO MEDIANTE CONTACTO, EN UNA MEZCLA DE TOLUENO Y METANOL COMO DISOLVENTE, UNA MEZCLA SUBSTANCIALMENTE RACEMICA DEL ACIDO FENILPROPIONICO CON UN ENANTIOMERO DE (OMEGA)-METILOBENCILAMINA, EL PORCENTAJE MOLAR RESPECTIVO DEL ACIDO FENILPROPIONICO SUBSTANCIALMENTE RACEMICO RESPECTO A LA (OMEGA)-METILOBENCILAMINA ESTANDO EN UN RANGO DE 1:0.25 A 1:1; (B) UNA ETAPA DE RECRISTALIZACION, EN LA CUAL LA SAL ENRIQUECIDA RESULTANTE SE RECRISTALIZA DESDE UNA MEZCLA DE METANOL Y TOLUENO PARA DAR UNA SAL DE (OMEGA)-METILOBENCILAMINA DEL ACIDO FENILPROPIONICO QUE ADEMAS ES ENRIQUECIDA EN EL ENANTIOMERO DESEADO; (C) UNA ETAPA DE LIBERACION OPCIONAL, EN LA CUAL EL ACIDO FENILPROPIONICO QUE ADEMAS ESTA ENRIQUECIDO EN EL ENANTIOMERO DESEADO SE LIBERA DE LA SAL RECRISTALIZADA; (D) UNA ETAPA DE PREPARACION DE LA SAL OPCIONAL EN LA CUAL UNA SAL SOLIDA DEL ACIDO FENILPROPIONICO ENRIQUECIDO ADEMAS EN EL ENANTIOMERO DESEADO ES AISLADA, LA SAL SOLIDA OPCIONALMENTE ES INCLUSO ADEMAS ENANTIOMERICAMENTE ENRIQUECIDA EN EL ENANTIOMERO DESEADO. EL ENANTIOMERO DESEADO ES PREFERIBLEMENTE EL (S)-ENANTIOMERO, LAS SALES PREFERIDAS SON LA (OMEGA)-METILOBENCILAMINA, LISINA Y SALES DE SODIO.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB929225203A GB9225203D0 (en) | 1992-12-02 | 1992-12-02 | Process |
GB929225202A GB9225202D0 (en) | 1992-12-02 | 1992-12-02 | Process |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2100037T3 true ES2100037T3 (es) | 1997-06-01 |
Family
ID=26302084
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES94901940T Expired - Lifetime ES2100037T3 (es) | 1992-12-02 | 1993-11-30 | Proceso para preparar enantiomeros sustancialmente puros de acidos fenilpropionicos. |
Country Status (12)
Country | Link |
---|---|
US (1) | US5599969A (es) |
EP (1) | EP0672030B1 (es) |
JP (1) | JPH08504193A (es) |
KR (1) | KR100280766B1 (es) |
AT (1) | ATE151740T1 (es) |
AU (1) | AU672269B2 (es) |
CA (1) | CA2150355C (es) |
DE (1) | DE69309958T2 (es) |
ES (1) | ES2100037T3 (es) |
FI (1) | FI110776B (es) |
RU (1) | RU2133733C1 (es) |
WO (1) | WO1994012460A1 (es) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5380867A (en) * | 1992-12-02 | 1995-01-10 | Hoechst Celanese Corporation | Selective precipitation of α-aryl carboxylic acid salts |
IN189741B (es) * | 1998-11-09 | 2003-04-19 | Council Scient Ind Res | |
CA2406383A1 (en) * | 2000-04-13 | 2001-10-25 | Mayo Foundation For Medical Education And Research | A.beta.42 lowering agents |
JP2002069030A (ja) * | 2000-08-30 | 2002-03-08 | Kyowa Hakko Kogyo Co Ltd | ナトリウム2−{4−[(2−オキソシクロペンチル)メチル]フェニル}プロピオネート2水和物の製造法 |
JP2006335639A (ja) * | 2003-01-23 | 2006-12-14 | Nagase & Co Ltd | 光学活性なフルルビプロフェンの製造方法 |
EP1603548A4 (en) * | 2003-02-05 | 2007-10-10 | Myriad Genetics Inc | COMPOSITION AND METHOD FOR TREATING NEURODEGENERATIVE DISORDERS |
EP1651195A4 (en) * | 2003-07-11 | 2007-10-03 | Myriad Genetics Inc | PHARMACEUTICAL PROCESSES, DOSIERSCHEMATA AND DOSAGE FORMS FOR THE TREATMENT OF ALZHEIMER DISEASE |
US20070293538A1 (en) * | 2004-04-13 | 2007-12-20 | Myriad Genetics, Incorporated | Pharmaceutical Composition And Methods For Treating Neurodegenerative Disorders |
AU2005241023A1 (en) * | 2004-04-29 | 2005-11-17 | Keystone Retaining Wall Systems, Inc. | Veneers for walls, retaining walls and the like |
WO2006020850A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
WO2006020852A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
CA2580363A1 (en) * | 2004-10-28 | 2006-05-11 | Idexx Laboratories, Inc. | Compositions for controlled delivery of pharmaceutically active compounds |
WO2007014124A2 (en) * | 2005-07-22 | 2007-02-01 | Myriad Genetics, Inc. | High drug load formulations and dosage forms |
US7754679B2 (en) * | 2005-11-16 | 2010-07-13 | Idexx Laboratories, Inc. | Pharmaceutical compositions for the administration of aptamers |
US8114440B2 (en) * | 2005-11-16 | 2012-02-14 | Idexx Laboratories Inc. | Pharmaceutical compositions for the administration of aptamers |
US20080033045A1 (en) * | 2006-07-07 | 2008-02-07 | Myriad Genetics, Incorporated | Treatment of psychiatric disorders |
CA2677125C (en) * | 2007-02-01 | 2018-07-10 | Myriad Genetics, Inc. | Drug substance preparations, pharmaceutical compositions and dosage forms |
US8828960B2 (en) * | 2007-07-17 | 2014-09-09 | Idexx Laboratories, Inc. | Amino acid vitamin ester compositions for controlled delivery of pharmaceutically active compounds |
GB0811851D0 (en) * | 2008-06-30 | 2008-07-30 | Aesica Pharmaceuticals Ltd | Process |
GB201216893D0 (en) * | 2012-09-21 | 2012-11-07 | Aesica Pharmaceuticals Ltd | Drug substance preparations, pharmaceutical compositions and dosage forms comprising s-(+)-flurbiprofen |
GB201405456D0 (en) * | 2014-03-26 | 2014-05-07 | Aesica Pharmaceuticals Ltd | Process for the manufacture of S-(+)-Flurbiprofen |
CN115286501A (zh) * | 2022-08-10 | 2022-11-04 | 浙江新和成股份有限公司 | 一种布洛芬结晶母液的综合利用方法 |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1497044A (en) * | 1974-03-07 | 1978-01-05 | Prodotti Antibiotici Spa | Salts of phenyl-alkanoic acids |
IT1059677B (it) * | 1974-03-22 | 1982-06-21 | Neopharmed Spa | Sale di lisina ad azione terapeutica |
JPS55136245A (en) * | 1979-04-09 | 1980-10-23 | Sumitomo Chem Co Ltd | Optical resolution of alpha-isopropyl-p-chlorophenyl-acetic acid |
DE3824353A1 (de) * | 1988-07-19 | 1990-01-25 | Paz Arzneimittelentwicklung | Verfahren zur trennung von gemischen enantiomerer arylpropionsaeuren |
NO902190L (no) * | 1989-05-16 | 1990-11-19 | Puetter Medice Chem Pharm | Fremgangsmaate for fremstilling av optisk aktive 2-arylalkanonsyrer, saerlig 2-arylpropionsyrer. |
DK0424028T3 (da) * | 1989-10-17 | 1996-01-29 | Merck & Co Inc | S(+)-ibuprofen-L-aminosyre og S(+)-ibuprofen-D-aminosyre som et forbedret smertestillende middel med fremskyndet indtrædelse |
US5200558A (en) * | 1989-10-17 | 1993-04-06 | Merck & Co., Inc. | S(+)-ibuprofen-L-amino acid and S(+)-ibuprofen-D-amino acid as onset-hastened enhanced analgesics |
US4994604A (en) * | 1990-01-10 | 1991-02-19 | Merck & Co., Inc. | Formation and resolution of ibuprofen lysinate |
US5015764A (en) * | 1990-06-18 | 1991-05-14 | Ethyl Corporation | Preparation of optically active aliphatic carboxylic acids |
DE4028906A1 (de) * | 1990-09-12 | 1992-03-19 | Paz Arzneimittelentwicklung | Arzneimittel sowie deren herstellung und deren verwendung bei der bekaempfung von schmerzen und/oder entzuendungen und/oder fieber an tieren und menschen |
HUT59692A (en) * | 1990-11-15 | 1992-06-29 | Puetter Medice Chem Pharm | Process for producing complexes containing s/+/-phenyl-alkanoic acids and aminosugars |
HUT59656A (en) * | 1990-11-15 | 1992-06-29 | Puetter Medice Chem Pharm | Process for producing s/+/-phenyl-alkanoic acids and alpha-amino-acids containing complexes and pharmaceutical compositions containing them as active components |
EP0505180B1 (en) * | 1991-03-22 | 1996-10-09 | Merck & Co. Inc. | High-content ibuprofen lysinate pharmaceutical formulation |
CA2102530C (en) * | 1991-05-13 | 2003-07-29 | Bernard J. Armitage | Therapeutic agent |
FR2687673B1 (fr) * | 1992-01-13 | 1995-07-07 | Jung Jean | Sels amines d'acides arylcarboxyliques, sterilisables, solubles dans l'eau, utilises en ophtalmologie et/ou dans la sphere otorhinolaryngologique. |
US5302751A (en) * | 1992-01-21 | 1994-04-12 | Ethyl Corporation | Profen resolution |
US5288507A (en) * | 1992-07-29 | 1994-02-22 | Merck & Co., Inc. | Ibuprofen antacid combinations |
WO1994003209A1 (en) * | 1992-07-29 | 1994-02-17 | Merck & Co., Inc. | Dexibuprofen/antacid/simethicone combinations |
AU5132893A (en) * | 1992-09-29 | 1994-04-26 | Mcneil-Ppc, Inc. | Ibuprofen-caffeine combinations |
US5248813A (en) * | 1992-10-14 | 1993-09-28 | Ethyl Corporation | Enantiomeric resolution |
US5260482A (en) * | 1992-10-14 | 1993-11-09 | Ethyl Corporation | Enantiomeric resolution |
US5278337A (en) * | 1992-10-14 | 1994-01-11 | Ethyl Corporation | Enantiomeric resolution of aryl-substituted aliphatic carboxylic acids |
US5380867A (en) * | 1992-12-02 | 1995-01-10 | Hoechst Celanese Corporation | Selective precipitation of α-aryl carboxylic acid salts |
-
1993
- 1993-11-30 RU RU95113445/04A patent/RU2133733C1/ru not_active IP Right Cessation
- 1993-11-30 EP EP94901940A patent/EP0672030B1/en not_active Expired - Lifetime
- 1993-11-30 US US08/424,517 patent/US5599969A/en not_active Expired - Lifetime
- 1993-11-30 AT AT94901940T patent/ATE151740T1/de not_active IP Right Cessation
- 1993-11-30 JP JP6512791A patent/JPH08504193A/ja active Pending
- 1993-11-30 DE DE69309958T patent/DE69309958T2/de not_active Expired - Lifetime
- 1993-11-30 ES ES94901940T patent/ES2100037T3/es not_active Expired - Lifetime
- 1993-11-30 CA CA002150355A patent/CA2150355C/en not_active Expired - Lifetime
- 1993-11-30 AU AU56504/94A patent/AU672269B2/en not_active Expired
- 1993-11-30 WO PCT/EP1993/003376 patent/WO1994012460A1/en active IP Right Grant
- 1993-11-30 KR KR1019950702237A patent/KR100280766B1/ko not_active IP Right Cessation
-
1995
- 1995-06-01 FI FI952677A patent/FI110776B/fi active
Also Published As
Publication number | Publication date |
---|---|
EP0672030A1 (en) | 1995-09-20 |
AU672269B2 (en) | 1996-09-26 |
EP0672030B1 (en) | 1997-04-16 |
DE69309958T2 (de) | 1997-07-24 |
JPH08504193A (ja) | 1996-05-07 |
RU95113445A (ru) | 1997-06-10 |
FI952677A (fi) | 1995-06-01 |
DE69309958D1 (de) | 1997-05-22 |
CA2150355A1 (en) | 1994-06-09 |
KR100280766B1 (ko) | 2001-02-01 |
FI952677A0 (fi) | 1995-06-01 |
KR950704226A (ko) | 1995-11-17 |
FI110776B (fi) | 2003-03-31 |
AU5650494A (en) | 1994-06-22 |
ATE151740T1 (de) | 1997-05-15 |
WO1994012460A1 (en) | 1994-06-09 |
US5599969A (en) | 1997-02-04 |
CA2150355C (en) | 2008-03-11 |
RU2133733C1 (ru) | 1999-07-27 |
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Legal Events
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