1-Alkyl-1,4-dihydro-4-oxo-7-triazenyl-3-quinolinecarboxylic acids
US4137227A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Aug 29, 1977 |
| Grant date | Jan 30, 1979 |
| Priority date | — |
| Expiry date | Aug 29, 1997 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D215/56
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Compounds useful as antibacterial agents are 1-R-1,4-dihydro-4-oxo-7-(BN--N.dbd.N)-3-quinolinecarboxylic acids (I), wherein: (a) BN is dimethylamino where R is methyl, ethyl, n-propyl, n-butyl, n-pentyl or n-octyl; (b) BN is diethylamino where R is n-propyl; or, (c) BN is 4-methyl-1-piperazinyl where R is ethyl. These compounds are prepared by reacting lower-alkyl 7-amino-1-R-1,4-dihydro-4-oxo-3-quinolinecarboxylate (II) with a mineral acid and an alkali nitrite in aqueous medium to produce the corresponding diazonium salt of said 7-aminoquinoline, reacting said diazonium salt with an amine of the formula BNH in the presence of an acid-acceptor to produce lower-alkyl 1-R-1,4-dihydro-4-oxo-7-(BN--N.dbd.N)-3-quinolinecarboxylate and hydrolyzing said 3-quinolinecarboxylate to produce the corresponding 3-carboxylic acid (I). The intermediate lower-alkyl 7-amino-1-R-1,4-dihydro-4-oxo-3-quinolinecarboxylate (II) are prepared in several steps by conventional means starting with m-aniline.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.