ES2120881A1 - 5-Methyl-1,3-thiazine-2,4-dione enantiomers and their use in the synthesis of chiral drug intermediates - Google Patents

5-Methyl-1,3-thiazine-2,4-dione enantiomers and their use in the synthesis of chiral drug intermediates

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Publication number
ES2120881A1
ES2120881A1 ES09600265A ES9600265A ES2120881A1 ES 2120881 A1 ES2120881 A1 ES 2120881A1 ES 09600265 A ES09600265 A ES 09600265A ES 9600265 A ES9600265 A ES 9600265A ES 2120881 A1 ES2120881 A1 ES 2120881A1
Authority
ES
Spain
Prior art keywords
thiazine
dione
enantiomers
synthesis
methyl
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
Application number
ES09600265A
Other languages
Spanish (es)
Other versions
ES2120881B1 (en
Inventor
Bayo Antonio Pallares
Morales Manuel Esteban
Jimenez Ana Maria Moreno
Almaraz Pablo Garcia
La Escalera Hueso Santiago De
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DSM DERETIL SA
Deretil SA
Original Assignee
DSM DERETIL SA
DSM Deretil SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by DSM DERETIL SA, DSM Deretil SA filed Critical DSM DERETIL SA
Priority to ES9600265A priority Critical patent/ES2120881B1/en
Publication of ES2120881A1 publication Critical patent/ES2120881A1/en
Application granted granted Critical
Publication of ES2120881B1 publication Critical patent/ES2120881B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

5-Methyl-1,3-thiazine-2,4-dione enantiomers and their use in the synthesis of chiral drug intermediates. 5-Methyl-1,3-thiazine-2,4-dione enantiomers (I) are suitable for synthesis of the active ingredients of chiral drugs. In particular the S enantiomer of (I) is useful in the synthesis of S-(-)-3-acetylthio-2- methylpropionic acid (S-AMPA), a precursor of Captopril. These enantiomers can be obtained by stereoselective enzyme hydrolysis of racemic 5-methyl-1,3-thiazine-2,4- dione in the presence of a biocatalyst which contains enzymes capable of hydrolysing the said racemic mixture in a stereoselective way. <IMAGE>
ES9600265A 1996-02-05 1996-02-05 ENANTIOMERS OF 5-METHYL-1, 3-TIAZIN-2, 4-DIONA AND ITS USE IN THE INTERMEDIATE SYNTHESIS OF CHIRAL PHARMACES. Expired - Lifetime ES2120881B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ES9600265A ES2120881B1 (en) 1996-02-05 1996-02-05 ENANTIOMERS OF 5-METHYL-1, 3-TIAZIN-2, 4-DIONA AND ITS USE IN THE INTERMEDIATE SYNTHESIS OF CHIRAL PHARMACES.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES9600265A ES2120881B1 (en) 1996-02-05 1996-02-05 ENANTIOMERS OF 5-METHYL-1, 3-TIAZIN-2, 4-DIONA AND ITS USE IN THE INTERMEDIATE SYNTHESIS OF CHIRAL PHARMACES.

Publications (2)

Publication Number Publication Date
ES2120881A1 true ES2120881A1 (en) 1998-11-01
ES2120881B1 ES2120881B1 (en) 1999-11-16

Family

ID=8293694

Family Applications (1)

Application Number Title Priority Date Filing Date
ES9600265A Expired - Lifetime ES2120881B1 (en) 1996-02-05 1996-02-05 ENANTIOMERS OF 5-METHYL-1, 3-TIAZIN-2, 4-DIONA AND ITS USE IN THE INTERMEDIATE SYNTHESIS OF CHIRAL PHARMACES.

Country Status (1)

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ES (1) ES2120881B1 (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0350811A2 (en) * 1988-07-14 1990-01-17 E.R. SQUIBB &amp; SONS, INC. Enzymatic resolution process
EP0369553A1 (en) * 1988-11-18 1990-05-23 Dsm N.V. Process for the enantioselective preparation of D-(-)-3-hal-2-methylpropionic acid or derivatives thereof and the preparation of captopril therefrom
US5128263A (en) * 1988-07-14 1992-07-07 E. R. Squibb & Sons, Inc. Enzymatic resolution process hydrolyzing thio-ester
US5177006A (en) * 1988-07-14 1993-01-05 E. R. Squibb & Sons, Inc. Enzymatic resolution process

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0350811A2 (en) * 1988-07-14 1990-01-17 E.R. SQUIBB &amp; SONS, INC. Enzymatic resolution process
US5128263A (en) * 1988-07-14 1992-07-07 E. R. Squibb & Sons, Inc. Enzymatic resolution process hydrolyzing thio-ester
US5177006A (en) * 1988-07-14 1993-01-05 E. R. Squibb & Sons, Inc. Enzymatic resolution process
EP0369553A1 (en) * 1988-11-18 1990-05-23 Dsm N.V. Process for the enantioselective preparation of D-(-)-3-hal-2-methylpropionic acid or derivatives thereof and the preparation of captopril therefrom

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
AGRIC. BIOL. CHEM., Vol. 47 (6), pßginas 1363-1365, 1983. H. KUTANI et al. "Asymmetric Hydrolysis of Prochiral Dimethyl 3-Benzyoxycarbonylaminoglutarate with Microorganism." * Tabla 1 * *

Also Published As

Publication number Publication date
ES2120881B1 (en) 1999-11-16

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