Title:
PREPARATION OF RACEMIC PILOSININE DERIVATIVE
Document Type and Number:
Japanese Patent JP3174600
Kind Code:
B2
Abstract:
PURPOSE: To easily obtain a pilosinine deriv. which can be used as a precursor of pilocarpine having pharmaceutical effects such as perspiration, stimulation on parasympathetic nervous system and miotic effect, from an easily available starting substance without by-products with high yield.
CONSTITUTION: A compd. expressed by formula I (R1 is a 1 to 6 C straight-chain or branched alkyl) is allowed to react with a substd. or unsubstd. thiophenol, alkanethiol or alkenethiol under refluxing conditions to convert into a new substance expressed by formula II (R2, R3 are each a 1 to 5 C alkyl, substd. or unsubstd. phenyl or benzyl, R2 and R3 may form a 1 to 5 C alkylene). Then the obtd. substance is subjected to deprotonation in the presence of a base, preferably an org. alkali metal compd., and to the reaction with γ-crotonolactone to obtain a new substance expressed by formula III. Moreover, preferably the new substance is reduced by using a hydrogenated multimetal compd. (such as LiAlH4, NaB2H7) or Raney nickel to advantageously obtain a pilosinine deriv. expressed by formula IV with high yield.
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Inventors:
Ulrich Haveng
Michael Custo
Michael schwarz
Michael Custo
Michael schwarz
Application Number:
JP27381791A
Publication Date:
June 11, 2001
Filing Date:
October 22, 1991
Export Citation:
Assignee:
Merck Patent Gesellschaft Mitt Beschlenktel Haftung
International Classes:
A61P27/02; B01J25/02; C07B61/00; C07D233/54; A61K31/415; C07D233/58; C07D241/18; C07D405/06; (IPC1-7): C07D405/06; C07D241/18
Attorney, Agent or Firm:
Nobuyuki Kaneda (2 others)