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New process for the synthesis of imidazo[4,5‐ b ]pyridine derivatives as potent orally active thromboxane a 2 receptor antagonists
Author(s) -
Nicolaï E.,
Claude S.,
Teulon J. M.
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310113
Subject(s) - chemistry , orally active , pyridine , antagonist , acetic anhydride , combinatorial chemistry , acetic acid , bicyclic molecule , stereochemistry , receptor antagonist , receptor , medicinal chemistry , organic chemistry , in vitro , biochemistry , catalysis
A new synthetic route to prepare the 4‐[3‐(4‐chlorophenyl)methyl‐6‐chloroimidazo[4,5‐ b ]pyridin‐2‐yl]‐3,3‐dimethylbutanoic acid (UP 116‐77) is described. UP 116‐77 is a potent orally active TXA 2 /PGH 2 receptor antagonist currently under pharmacological investigation. Its development needed a suitable synthesis for industrial processing. The cyclization of 3‐amino‐5‐chloro‐2‐(4‐chlorophenyl)methylaminopyridine 4 with 3,3‐dimethylglutaric anhydride in refluxing acetic acid affords a new efficient and simple way to UP 116‐77 and subsequently to various 2‐substituted imidazo[4,5‐ b ]pyridine derivatives.