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EP0146228A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Substituted 2-mercapto-imidazoles and their preparation and use

Assignee: Farmos Yhtyma Oy
•
Filing: 1984-10-16
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Granted: —
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Expires: 2004-10-16
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Abstract

Abstract The invention provides novel 1-substituted-5-hydroxymethyl-2-mercapto-imidazoles of the formula wherein R is pyridylmethyl, alkyl of 1 to 4 carbon atoms, or a radical of formula: R 1 is hydrogen or halogen and n is 1-3. These compounds are prepared by reacting together dihydroxyacetone dimer, the amine R-NH 2 , and potassium thiocyanate. The compounds of formula (I) are useful as starting materials in the preparation of known therapeutically valuable imidazole derivatives, by removing the mercapto group, oxidizing the alcohol group to an aldehyde group and condensing the aldehyde with an appropriate phenyl or phenylalkyl magnesium halide.

Inventors

  • 👤 Seppo S.L. Parhi

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-06 14:10
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/06; C07D233/00; C07D233/54; C07D233/66; C07D233/84

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 38 words
1-Substituted-5-hydroxymethyl-2-mercapto- imidazoles of the formula and their acid addition salts, wherein R is pyridylmethyl, alkyl of 1 to 4 carbon atoms, or a radical of formula: in which R 1 is hydrogen or halogen and n is 1-3.
Claim 2
Dependent Claim 38 words
1-Substituted-5-hydroxymethyl-2-mercapto- imidazoles of the formula and their acid addition salts, wherein R is pyridylmethyl, alkyl of 1 to 4 carbon atoms, or a radical of formula: in which R 1 is hydrogen or halogen and n is 1-3.
Claim 3
Dependent Claim 17 words
A substituted imidazole according to claim 1 in which R is benzyl, 4-chlorobenzyl, 2-phenylethyl, 2-pyridyl-methyl, or ethyl.
Claim 4
Dependent Claim 1 words
1-Benzyl-2-mercapto-5-hydroxymethyl-imidazole.
Claim 5
Dependent Claim 1 words
1-Benzyl-2-mercapto-5-hydroxymethyl-imidazole.
Claim 6
Dependent Claim 52 words
A process for the preparation of a compound as claimed in claim 1 which comprises reacting dihydroxyacetone dimer with potassium thiocyanate and a primary amine of formula: wherein R is as defined in claim 1, in a lower alcohol in the presence of an acid at a temperature of 10 - 100°C.
Claim 7
Dependent Claim 57 words
Process for the preparation of a compound of formula: wherein R is as defined in claim 1, which comprises reacting a compound of formula I as claimed in claim 1 with an oxidizing agent to remove the mercapto group and oxidizing the primary alcohol group in the compound as claimed in claim 1 to an aldehyde group.

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