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1. WO1996033990 - SYNTHESIS OF (S)-3-(2-THIENYLTHIO) BUTYRIC ACID AND ANALOGS

Publication Number WO/1996/033990
Publication Date 31.10.1996
International Application No. PCT/US1996/005623
International Filing Date 22.04.1996
Chapter 2 Demand Filed 11.11.1996
IPC
C07D 333/34 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
333Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
02not condensed with other rings
04not substituted on the ring sulfur atom
26with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
30Hetero atoms other than halogen
34Sulfur atoms
C07D 495/04 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
495Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
CPC
C07D 333/34
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
333Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
02not condensed with other rings
04not substituted on the ring sulfur
26with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
30Hetero atoms other than halogen
34Sulfur atoms
C07D 495/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
495Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
Applicants
  • MERCK & CO., INC. [US]/[US] (AllExceptUS)
  • MATHRE, David, J. [US]/[US] (UsOnly)
  • SOHAR, Paul [US]/[US] (UsOnly)
  • BROWN, Lynn, May [US]/[US] (UsOnly)
Inventors
  • MATHRE, David, J.
  • SOHAR, Paul
  • BROWN, Lynn, May
Common Representative
  • MERCK & CO., INC.
Priority Data
08/430,21426.04.1995US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) SYNTHESIS OF (S)-3-(2-THIENYLTHIO) BUTYRIC ACID AND ANALOGS
(FR) SYNTHESE D'ACIDE (S)-3-2-THIENYLTHIO) BUTYRIQUE ET D'ANALOGUES
Abstract
(EN)
This invention is concerned with an improved process for the synthesis of and intermediate en route to 5,6-dihydro-(s)-4-(ethylamino)-(s)-6-methyl-4h-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide and related compounds. The instant process reduces the reaction time for the synthesis of the key intermediate from 3 to 4 days to from about 2 to about 4 hours while retaining the high enantiomeric purity of the product.
(FR)
Procédé amélioré de synthèse d'un intermédiaire en vue de la préparation de 5,6-dihydro-(s)-4-(éthylamino)-(s)-6-méthyl-4h-thiéno(2,3-b)thiopyrane-2-sulfonamide 7,7-dioxyde et de composés associés. Ce procédé réduit le temps de réaction pour la synthèse de cet intermédiaire essentiel, le faisant passer de 3 à 4 jours à 2 à 4 heures environ, tout en préservant la pureté énantiomérique élevée du produit.
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