Derivatives of quinoline-3-carboxanilide

• US 5,310,913 A
• Filed: 08/05/1993
• Issued: 05/10/1994
• Est. Priority Date: 06/09/1989
• Status: Expired due to Fees

• Current Assignee: Pharmacia AB (Pharmacia Corp.)
• Original Assignee: Kabi Pharmacia AB (Pfizer Inc.)
• Inventors: Johansson, Kaj, Stalhandske, Torbjorn, Lundvall, Karl-Erik, Strandgarden, Kerstin, Gunnarsson, Per O.
• Primary Examiner(s): Daus, Donald G.
• Application Number:
  US08/102,393
• Time in Patent Office: 278 Days
• Field of Search: 514/312, 546/155
• US Class Current: 546/155
• CPC Class Codes: C07D 215/56 with oxygen atoms in position 4

Abstract

Compounds having formula ##STR1## wherein R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are selected from the group consisting of hydrogen, hydroxy and methoxy. At most one of R¹, R² and R³ and at most one of R⁴, R⁵, R⁶ and R⁷ is selected from the group consisting of hydroxy and methoxy. M is selected from the group consisting of hydrogen and pharmaceutically acceptable inorganic or organic cations or tautomeric forms thereof. The compounds have immunomodulating activity.

Claims

1. A novel compound having the formula ##STR5## wherein R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are selected from the group consisting of hydrogen, hydroxy and methoxy, wherein at most one of R¹, R² and R³ and at most one of R⁴, R⁵, R⁶ and R⁷ are selected from the group consisting of hydroxy and methoxy;

and M is selected from the group consisting of hydrogen and pharmaceutically acceptable inorganic or organic cations or tautomeric forms thereof.

2. A compound according to claim 1, wherein said compound is N-methyl-N-phenyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxamide.

3. A compound according to claim 1, wherein said compound is N-methyl-N-(4-methoxyphenyl)-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxamide.

4. A compound according to claim 1, wherein said compound is N-methyl-4-phenyl-1,2-dihydro-4-hydroxy-6-methoxy-2-oxo-quinoline-3-carboxamide.

5. A compound according to claim 1, wherein said compound is selected from the group consisting of N-methyl-N-(4-methoxyphenyl)-1,2-dihydro-4-hydroxy-6-methoxy-2-oxo-quinoline-3-carboxamide and N-methyl-N-(3-methoxyphenyl)-1,2-dihydro-4-hydroxy-7-methoxy-2-oxo-quinoline-3-carboxamide.

6. A compound according to claim 1, wherein said compound is N-methyl-N-(4-methoxyphenyl)-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxamide.

7. A compound according to claim 1, wherein said compound is N-methyl-N-phenyl-1,2-dihydro-4,6-hydroxy-2-oxo-quinoline-3-carboxamide.

8. A compound according to claim 1 wherein said compound is selected from the group consisting of N-methyl-N-phenyl-1,2-dihydro-4,7-dihydroxy-2-oxo-quinoline-3-carboxamide and N-methyl-N-(4-hydroxy-phenyl)-1,2-dihydro-4,6-hydroxy-2-oxo-quinoline-3-carboxamide.