Disubstituted-7-pyrrolidinonaphthyridine antibacterial agents

• US 4,735,949 A
• Filed: 06/22/1987
• Issued: 04/05/1988
• Est. Priority Date: 02/18/1986
• Status: Expired due to Term

• Current Assignee: Warner-Lambert Company (Pfizer Inc.)
• Original Assignee: Warner-Lambert Company (Pfizer Inc.)
• Inventors: Solomon, Marjorie S., Prugh, Susan E., Domagala, John M., Sanchez, Joseph P.
• Primary Examiner(s): Jiles, Henry R.
• Assistant Examiner(s): Dentz, Bernard I.
• Application Number:
  US07/064,439
• Time in Patent Office: 288 Days
• Field of Search: 546/123, 514/300
• US Class Current: 514/300
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond

Abstract

Disubstituted 7-pyrrolidinoquinoline- and -naphthyridine-3-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections.

Claims

1. A compound of the formula ##STR5## wherein X is N;

R₁ is hydrogen or alkyl of one to six carbon atoms;

R₂ is alkyl of one to four carbon atoms, vinyl, haloalkyl or hydroxyalkyl of two to four carbon atoms, or cycloalkyl of three to six carbon atoms;

n is zero to three;

R₃ is OR₄ or NR₄ R₅, in which R₄ and R₅ are each independently hydrogen or alkyl of one to six carbon atoms;

Ar is phenyl or phenyl substituted by alkyl of one to four carbon atoms, halogen, trifluoromethyl, OR₄ or NR₄ R₅, or a pharmaceutically acceptable acid addition or base salt thereof.

2. A compound according to claim 1, wherein R₂ is ethyl, vinyl, 2-fluoroethyl, hydroxyethyl or cyclopropyl;

n is zero or one;

R₃ is OH, NH₂, methylamino, dimethylamino, ethylamino or diethylamino, and Ar is phenyl or phenyl substituted by methyl, methoxy, fluorine, chlorine, hydroxy, trifluoromethyl, amino, methylamino, dimethylamino, ethylamino, or diethylamino.

3. A compound according to claim 2, wherein X is N;

R₁ is hydrogen, methyl or ethyl;

R₂ is ethyl, vinyl, 2-fluoroethyl or cyclopropyl;

R₃ is OH or NH₂, and Ar is phenyl or phenyl substituted by methyl, methoxy, fluorine, chlorine, hydroxy, trifluoromethyl or amino.

4. A compound according to claim 3, wherein R₁ is hydrogen;

R₂ is cyclopropyl, and Ar is phenyl.

5. An antibacterial composition comprising an antibacterially effective amount of a compound as claimed in claim 1 together with a pharmaceutically acceptable carrier or diluent.

6. A method of treating bacterial infections in a mammal which comprises administering to said mammal suffering therefrom an antibacterial composition as claimed in claim 5.