ES2128959B1 - Procedimiento de separacion de carbinoles. - Google Patents
Procedimiento de separacion de carbinoles.Info
- Publication number
- ES2128959B1 ES2128959B1 ES009602666A ES9602666A ES2128959B1 ES 2128959 B1 ES2128959 B1 ES 2128959B1 ES 009602666 A ES009602666 A ES 009602666A ES 9602666 A ES9602666 A ES 9602666A ES 2128959 B1 ES2128959 B1 ES 2128959B1
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- pyrazole
- phenyl
- procedure
- carbinol
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title abstract 4
- 238000000926 separation method Methods 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title 2
- ZMDMCKKOZJKHKG-UHFFFAOYSA-N (1-methyl-5-phenylpyrazol-3-yl)methanol Chemical compound CN1N=C(CO)C=C1C1=CC=CC=C1 ZMDMCKKOZJKHKG-UHFFFAOYSA-N 0.000 abstract 1
- 102000004882 Lipase Human genes 0.000 abstract 1
- 108090001060 Lipase Proteins 0.000 abstract 1
- 239000004367 Lipase Substances 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 235000019421 lipase Nutrition 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Steroid Compounds (AREA)
- Extraction Or Liquid Replacement (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
Procedimiento de separación de carbinoles. Procedimiento para preparar predominantemente el enantiómero (R)-(+)-5-(fenil)hidroximetil-1-metil-1H-pirazol, (R)-(+)-1, compuesto con propiedades analgésicas, por separación de la mezcla racémica (+-)-5-(fenil) hidroximetil-1-metil-1H-pirazol, de fórmula 1, que se caracteriza por un procedimiento secuencial que comprende la utilización de una lipasa o un material derivado de la misma que posea actividad enzimática en una reacción de transesterificación, así como la hidrólisis del éster formado, (S)-(-)-5-(fenil)alquilcarboniloximetil-1-metil-1H-pirazol, de fórmula (S)-(-)-4 en la cual R{sub,1 representa un radical metilo o etilo.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9514414A FR2742147B1 (fr) | 1995-12-06 | 1995-12-06 | Procede de separation de carbinols |
Publications (2)
Publication Number | Publication Date |
---|---|
ES2128959A1 ES2128959A1 (es) | 1999-05-16 |
ES2128959B1 true ES2128959B1 (es) | 2000-01-16 |
Family
ID=9485191
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES009602666A Expired - Fee Related ES2128959B1 (es) | 1995-12-06 | 1996-12-05 | Procedimiento de separacion de carbinoles. |
Country Status (23)
Country | Link |
---|---|
US (1) | US5849931A (es) |
EP (1) | EP0808308B1 (es) |
JP (1) | JPH11501943A (es) |
KR (1) | KR100452248B1 (es) |
CN (1) | CN1066716C (es) |
AT (1) | ATE199546T1 (es) |
AU (1) | AU703479B2 (es) |
CA (1) | CA2211156A1 (es) |
CZ (1) | CZ292548B6 (es) |
DE (1) | DE69611988T2 (es) |
DK (1) | DK0808308T3 (es) |
ES (1) | ES2128959B1 (es) |
FR (1) | FR2742147B1 (es) |
GR (1) | GR3035875T3 (es) |
HU (1) | HU221661B1 (es) |
IL (1) | IL121460A (es) |
NO (1) | NO318596B1 (es) |
NZ (1) | NZ324707A (es) |
PL (1) | PL188910B1 (es) |
PT (1) | PT808308E (es) |
RU (1) | RU2162464C2 (es) |
TR (1) | TR199700764T1 (es) |
WO (1) | WO1997020817A1 (es) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2130079B1 (es) | 1997-07-10 | 2000-01-16 | Esteve Labor Dr | Resolucion de aminas |
US20040142929A1 (en) * | 2001-07-06 | 2004-07-22 | Ramon Merce-Vidal | Derivatives of aryl (or heteroaryl) azolylcarbinoles for the treatment of urinary incontinence |
TW200533657A (en) * | 2004-02-17 | 2005-10-16 | Esteve Labor Dr | Substituted pyrazoline compounds, their preparation and use as medicaments |
EP1584335A3 (en) * | 2004-04-05 | 2006-02-22 | Laboratorios Del Dr. Esteve, S.A. | Active substance combination comprising a carbinol composition and an opioid |
ES2244326B1 (es) * | 2004-04-05 | 2007-02-16 | Laboratorios Del Dr. Esteve, S.A. | Combinacion de substancias activas. |
US20060040924A1 (en) * | 2004-06-22 | 2006-02-23 | Laboratorios Dr. Esteve S.A. | Derivatives of aryl (or heteroaryl) azolylcarbinols for the treatment of renal colic |
US7897589B2 (en) * | 2005-07-15 | 2011-03-01 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
EP1757587A1 (en) * | 2005-07-15 | 2007-02-28 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
EP1743892A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios del Dr. Esteve S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
EP1743890A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | 4,5-Dihydro-1H-pyrazole derivatives, their preparation and use as medicaments |
EP1820502A1 (en) | 2006-02-10 | 2007-08-22 | Laboratorios Del Dr. Esteve, S.A. | Active substance combination comprising azolylcarbinol compounds |
EP2151234A1 (en) * | 2008-07-28 | 2010-02-10 | Laboratorios Del. Dr. Esteve, S.A. | Pharmaceutical formulation comprising a CB1-receptor compound in a solid solution and/or solid dispersion |
EP2414339B1 (en) * | 2009-04-02 | 2013-01-16 | Lupin Ltd. | Kinetic resolution of (4s)-4-phenyl-3-[5(rs)-(4-fluorophenyl)-5-hydroxypentanoyl]-1,3 oxazolidin 2-one to (5s) isomer via lipase catalyzed enantioselective esterification of the (5r) isomer |
US20100291151A1 (en) * | 2009-04-21 | 2010-11-18 | Auspex Pharmaceuticals, Inc. | 1-methylpyrazole modulators of substance p, calcitonin gene-related peptide, adrenergic receptor, and/or 5-ht receptor |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3743824C2 (de) * | 1987-12-23 | 1997-03-06 | Hoechst Ag | Verfahren zur enzymatischen Racematspaltung von racemischen Alkoholen mit/in Vinylestern durch Umesterung |
-
1995
- 1995-12-06 FR FR9514414A patent/FR2742147B1/fr not_active Expired - Fee Related
-
1996
- 1996-12-04 CN CN96192450A patent/CN1066716C/zh not_active Expired - Fee Related
- 1996-12-04 CZ CZ19972502A patent/CZ292548B6/cs not_active IP Right Cessation
- 1996-12-04 DE DE69611988T patent/DE69611988T2/de not_active Expired - Fee Related
- 1996-12-04 AT AT96943113T patent/ATE199546T1/de not_active IP Right Cessation
- 1996-12-04 CA CA002211156A patent/CA2211156A1/fr not_active Abandoned
- 1996-12-04 HU HU9800517A patent/HU221661B1/hu not_active IP Right Cessation
- 1996-12-04 TR TR97/00764T patent/TR199700764T1/xx unknown
- 1996-12-04 AU AU11945/97A patent/AU703479B2/en not_active Ceased
- 1996-12-04 DK DK96943113T patent/DK0808308T3/da active
- 1996-12-04 JP JP9521006A patent/JPH11501943A/ja not_active Ceased
- 1996-12-04 PT PT96943113T patent/PT808308E/pt unknown
- 1996-12-04 KR KR1019970705341A patent/KR100452248B1/ko not_active IP Right Cessation
- 1996-12-04 PL PL96321682A patent/PL188910B1/pl not_active IP Right Cessation
- 1996-12-04 RU RU97114840/04A patent/RU2162464C2/ru not_active IP Right Cessation
- 1996-12-04 NZ NZ324707A patent/NZ324707A/en unknown
- 1996-12-04 EP EP96943113A patent/EP0808308B1/fr not_active Expired - Lifetime
- 1996-12-04 WO PCT/EP1996/005596 patent/WO1997020817A1/fr active IP Right Grant
- 1996-12-04 IL IL12146096A patent/IL121460A/xx not_active IP Right Cessation
- 1996-12-05 ES ES009602666A patent/ES2128959B1/es not_active Expired - Fee Related
-
1997
- 1997-08-01 NO NO19973566A patent/NO318596B1/no unknown
- 1997-12-04 US US08/875,806 patent/US5849931A/en not_active Expired - Fee Related
-
2001
- 2001-05-15 GR GR20010400728T patent/GR3035875T3/el not_active IP Right Cessation
Also Published As
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EC2A | Search report published |
Date of ref document: 19990516 Kind code of ref document: A1 Effective date: 19990516 |
|
FD2A | Announcement of lapse in spain |
Effective date: 20180807 |