Nova Patents
EP0343524A1

Pyridonecarboxylic acids and antibacterial agents.

Abstract

Novel pyridonecarboxylic acids of the formula : or the pharmaceutically acceptable salts thereof having a more potent and longer lasting antibacterial activites against gram-­positive and gram-negative bacteria than known analogues, useful for antibacterial agents at an oral dose of 1-500 mg, preferably 50-100 mg per day to an adult.

EP0343524A1, drawing sheet 1
Sheet 1 of 27

Term

Term ended

Projected expiry passed 19 May 2009, 17.3 years ago.

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5 claims: 1 independent, 4 dependent

  1. 1
    A compound of the formula :wherein R¹ is hydrogen, hydroxy, C₁-C₄ alkyl, C₁-C₄ alkoxy, oxo, halogen, or amino optionally substituted by C₁-C₄ alkyl and/or C₁-C₄ alkanoyl;R² is azido, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkanoyl, or amino optionally substituted by C₁-C₄ alkyl and/or C₁-C₄ alkanoyl;A is R³ is hydrogen or carboxy-protecting group;R⁴ is C₁-C₄ alkyl, C₂-C₅ alkenyl, C₃-C₅ cycloalkyl, mono- or di-fluorophenyl or 5- or 6-membered heterocyclic group optionally substituted by halogen and/or C₁-C₄ alkyl;R⁵ is hydrogen, amino, hydroxy, or C₁-C₄ alkoxy;R⁶ is halogen;X is CH-(C₁-C₄alkyl), C=CH₂, N-H, or N-(C₁-C₄alkyl);Z is CQ or N;Q is hydrogen, C₁-C₄ alkoxy, halogen, C₁-C₄ alkyl, or cyano;m is an integer of 0 or 1;n and p each is an integer of 1 to 3 or the pharmaceutically acceptable salts thereof. 1. A compound of the formula : wherein R¹ is hydrogen, hydroxy, C₁-C₄ alkyl, C₁-C₄ alkoxy, oxo, halogen, or amino optionally substituted by C₁-C₄ alkyl and/or C₁-C₄ alkanoyl;R² is azido, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkanoyl, or amino optionally substituted by C₁-C₄ alkyl and/or C₁-C₄ alkanoyl;A is R³ is hydrogen or carboxy-protecting group;R⁴ is C₁-C₄ alkyl, C₂-C₅ alkenyl, C₃-C₅ cycloalkyl, mono- or di-fluorophenyl or 5- or 6-membered heterocyclic group optionally substituted by halogen and/or C₁-C₄ alkyl;R⁵ is hydrogen, amino, hydroxy, or C₁-C₄ alkoxy;R⁶ is halogen;X is CH-(C₁-C₄alkyl), C=CH₂, N-H, or N-(C₁-C₄alkyl);Z is CQ or N;Q is hydrogen, C₁-C₄ alkoxy, halogen, C₁-C₄ alkyl, or cyano;m is an integer of 0 or 1;n and p each is an integer of 1 to 3 or the pharmaceutically acceptable salts thereof. 1. A method for producing a compound of the formula: wherein R¹ is hydrogen, hydroxy, C₁-C₄ alkyl, C₁-C₄ alkoxy, oxo, halogen, or amino optionally substituted by C₁-C₄ alkyl and/or C₁-C₄ alkanoyl;R² is azido, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkanoyl, or amino optionally substituted by C₁-C₄ alkyl and/or C₁-C₄ alkanoyl;A is R³ is hydrogen or carboxy-protecting group;R⁴ is C₁-C₄ alkyl, C₂-C₅ alkenyl, C₃-C₅ cycloalkyl, mono- or di-fluorophenyl or 5- or 6-membered heterocyclic group optionally substituted by halogen and/or C₁-C₄ alkyl;R⁵ is hydrogen, amino, hydroxy, or C₁-C₄ alkoxy;R⁶ is halogen;X is CH-(C₁-C₄alkyl), C=CH₂, N-H, or N-(C₁-C₄alkyl);Z is CQ or N;Q is hydrogen, C₁-C₄ alkoxy, halogen, C₁-C₄ alkyl, or cyano;m is an integer of 0 or 1;n and p each is an integer of 1 to 3 or the pharmaceutically acceptable salts thereof, which comprises reacting a compound of the formula: Hal-A      (II) wherein Hal is halogen and A has the same meaning as defined above with a compound of the formula : wherein R¹, R², m, n, and p have the same meanings as defined above and when a substituted amino group is contained in R¹ and/or R², optionally further subjecting the compound obtained to deprotective reaction to give a compound (Ia) in which the substituent has been eliminated from the substituted amino in R¹ and/or R².