Derivatives of 6,7 or 8 cycloalkyl 4-oxo quinoline 3 carboxylic acid

• US 3,960,868 A
• Filed: 05/06/1974
• Issued: 06/01/1976
• Est. Priority Date: 05/11/1973
• Status: Expired due to Term

• Current Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Haas, Georges, Rossi, Alberto, Ferrini, Pier Giorgio
• Primary Examiner(s): Rollins, Alton D.
• Assistant Examiner(s): Wheeler, David E.
• Application Number:
  US05/467,166
• Time in Patent Office: 757 Days
• Field of Search: 260/287 R, 260/287 AN
• US Class Current: 546/156
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: C07D 215/22 attached in position 2 or 4
• CPC Class Codes: C07D 215/54 attached in position 3
• CPC Class Codes: C07D 215/56 with oxygen atoms in position 4
• CPC Class Codes: C07D 265/26 Two oxygen atoms, e.g. isatoic anhydride

Abstract

##SPC1##

wherein Ph denotes a 1,2-phenylene radical which carries cycloaliphatic radical, R_x denotes a free or etherified hydroxyl group or a free or substituted amino group, R_o denotes an alkyl radical, a free hydroxyl group or a hydroxyl group etherified by lower alkyl or, above all, a hydrogen atom and R₁ denotes an aliphatic or cycloaliphatic hydrocarbon radical which is optionally substituted by hydroxyl, an araliphatic radical or a hydrogen atom, and their salts, which possess valuable analgesic, anti-inflammatory, anti-microbial and histamine liberation inhibiting properties.

Claims

1. A product of the formula ##SPC15##

wherein R_o denotes hydrogen or hydroxy, R₁ denotes hydrogen, alkyl, aklenyl or phenyl-alkyl having up to 8 carbon atoms R₂ is bound in the positions 6, 7 or 8 of the quinoline moiety and represents cycloalkyl or cycloalkenyl with 5-8 ring members, or 1-adamantyl, R₃ denotes lower alkyl, halogen or hydrogen and R_x denotes hydroxy, alkoxy with up to 8 carbon atoms, amino, N-mono-lower alkylamino, N,N-di-lower alkylamino or anilino, wherein the term "lower" denotes said moieties having up to 4 carbon atoms;

or a tautomeric form thereof, or a therapeutically acceptable salt thereof.

2. A product as claimed in claim 1 in which formula R_o represents hydrogen or hydroxy, R₁ denotes hydrogen, C₁ -C₄ -alkyl, C₃ -C₄ -alkenyl or -phenyl-C₁ -C₂ -alkyl-, R₂ denotes cycloalkyl or cycloalkenyl with 5 to 8 ring members or 1-adamantyl bound in 6-, 7- or 8-position of the quinoline moiety, R₃ denotes hydrogen or halogen and R_x denotes hydroxy, C₁ -C₃ -alkoxy or anilino;

or a tautomeric form thereof.

3. A compound as claimed in claim 1 and being the 8-cyclohexyl-1-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, or a therapeutically acceptable salt thereof.

4. A compound as claimed in claim 1 and being the 6-cyclohexyl-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, or a therapeutically acceptable salt thereof.

5. A compound as claimed in claim 1 and being the 6-cyclohexyl-4-hydroxy-quinoline-3-carboxylic acid ethyl ester, or a therapeutically acceptable salt thereof.

6. A compound as claimed in claim 1 and being the 6-cyclohexyl-4-hydroxy-quinoline-3-carboxylic acid, or a therapeutically acceptable salt thereof.

7. A compound as claimed in claim 1 and being the 7-cyclohexyl-4-hydroxy-quinoline-3-carboxylic acid, or a therapeutically acceptable salt thereof.

8. A compound as claimed in claim 1 and being the 7-cyclohexyl-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, or a therapeutically acceptable salt thereof.

9. A compound as claimed in claim 1 and being the 8-cyclohexyl-4-hydroxy-quinoline-3-carboxylic acid, or a therapeutically acceptable salt thereof.

10. A compound as claimed in claim 1 and being the 6-cycloheptyl-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester, or a therapeutically acceptable salt thereof.

11. A compound as claimed in claim 1 and being the 7-chloro-6-cyclohexyl-1-ethyl-4-oxo-1,4-dihydro-3-carboxylic acid, or a therapeutically acceptable salt thereof.