Acyl derivatives of 2-amino-4-substituted-5-hydroxy pyrimidines

Details Acyl derivatives of 2-amino-4-substituted-5-hydroxy pyrimidines Acyl derivatives of 2-amino-4-substituted-5-hydroxy pyrimidines

C - Chemistry, Metallurgy

07

D

167/211, 260/261

C07D 239/47 (2006.01) A61K 31/505 (2006.01) C07D 239/46 (2006.01) C07D 409/12 (2006.01) C07D 413/12 (2006.01)

Patent

CA 1336516

Disclosed are acyl derivatives of 2-Amino-4-substituted- 5-hydroxy pyrimidines of the formula: Image I wherein R1 is hydrogen or (C1-C15)alkyl; R2 is hydrogen, (C1- C15)alkyl, cyclopentyl, cyclohexyl, (C3-C15)alkenyl, phenyl, substituted phenyl, (C7-C20)phenylalkyl, or substituted (C7- C20)phenylalkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a pyrrolidinyl or piperidyl group which may be substituted by one (C1-C6)alkyl, phenyl or (C7- C20)phenylalkyl; R3 is (C1-C6)alkyl, phenyl, substituted phenyl, (C7-C20)phenylalkyl, substituted (C7-C20)phenylalkyl, furyl, thienyl, furyl substituted by one (C1-C3)alkyl, or thienyl be substituted by one (C1-C3)alkyl; R4 is hydrogen, (C1-C6)alkyl, phenyl, substituted phenyl, (C7-C20)phenylalkyl, or substituted (C7-C20)phenylalkyl; and R5 is (C1-C10)alkyl, (C1-C10)alkoxy, phenyl, substituted phenyl, (C7-C20)phenylalkyl, substituted (C7- C20)phenylalkyl, (C2-C3)alkylcarboxy, -NR6R7, wherein R6 and R7 are independently selected from the group consisting of (C1- C10)alkyl, phenyl, substituted phenyl, (C7-C20)phenylalkyl and substituted (C7-C20)phenylalkyl; wherein the phenyl moieties on the substituted phenyl and the substituted phenylalkyl are substituted by one or two moieties selected from the group consisting of fluoro, chloro, (C1-C3)alkyl, (C1-C3)alkoxy and CF3; with the proviso that when R1 and R2 are both hydrogen, R5 cannot be methyl; pharmaceutically acceptable acid addition salts thereof, and, when R5 is (C2-C3)alkylcarboxy, pharmaceutically acceptable base addition salts thereof. The compounds are inhibitors of leukotriene synthesis and are, therefore, useful for the treatment of pulmonary, inflammatory, dermatological, allergic and cardiovascular diseases. The compounds are also cytoprotective and therefore, useful in the treatment of peptic ulcers.

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