Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-12-17
2001-06-19
Seaman, D. Margaret (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S312000, C544S128000, C546S157000
Reexamination Certificate
active
06248739
ABSTRACT:
FIELD OF THE INVENTION
The present invention provides 4-oxo-1,4-dihydro-3-quinolinecarboxamide derivatives. These compounds are useful as antiviral agents, in particular, as agents against viruses of the herpes family.
BACKGROUND OF THE INVENTION
The herpesviruses comprise a large family of double stranded DNA viruses. They are also a source of the most common viral illnesses in man. Eight of the herpes viruses, herpes simplex virus types 1 and 2 (HSV-1 and HSV-2), varicella zoster virus (VZV), human cytomegalovirus (HCMV), epstein-Barr virus (EBV), and human herpes viruses 6, 7, and 8 (HHV-6, HHV-7, and (HHV-8), have been shown to infect humans.
HSV-1 and HSV-2 cause herpetic lesions on the lips and genitals, respectively. They also occasionally cause infections of the eye and encephalitis. HCMV causes birth defects in infants and a variety of diseases in immunocompromised patients such as retinitis, pneumonia, and gastrointestinal disease. VZV is the causitive agent of chicken pox and shingles. EBV causes infectious mononucleosis. It can also cause lymphomas in immunocompromised patients and has been associated with Burkitt's lymphoma, nasopharyngeal carcinoma, and Hodgkins disease. HHV-6 is the causitive agent of roseola and may be associated with multiple sclerosis and chronic fatigue syndrome. HHV-7 disease association is unclear, but it may be involved in some cases of roseola. HHV-8 has been associated with Karposi's sarcoma, body cavity based lymphomas, and multiple myeloma.
Compounds of the present invention are distinct from other hydroxyquinoline antiviral agents in that the 4-substituent on the benzyl amide of the present invention (i.e. the chloro, bromo, cyano, or nitro substituent) provides significantly improved antiviral activity. Certain compounds of formula (I) also possess unique substituents R
4
that provide improved antiviral activity.
INFORMATION DISCLOSURE
U.S. Pat. No. 5,891,878 and WO 97/04775 disclose compounds that are reported to be useful in the treatment of a disease state capable of being modulated by inhibition of production of phosphodiesterase IV or tumor necrosis factor. The genera of compounds disclosed in these applications are believed to overlap with the compounds of formula I disclosed herein. However, no specific compounds are prepared in these PCT applications having the 4-substitutedbenzamide group of the compounds of formula I herein.
U.S. Pat. No. 3,960,868 discloses derivatives of 6, 7, or 8 cycloalkyl-4-oxoquinoline-3-carboxylic acid that are reported to possess analgesic, anti-inflammatory, anti-microbial, and histamine liberating properties. The structure of these compounds differs from the structure of the compounds of formula I by requiring a cycloalkyl substituent at the 6, 7, or 8 position of the quinoline ring.
U.S. Pat. No. 4,959,363 discloses quinolonecarboxamide compounds that are reported to possess antiviral activity. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide, and at the 6-position by requiring a hydrogen or fluoro substituent.
U.S. Pat. No. 5,175,151, discloses quinolone compounds that are reported to possess antihypertensive and antiviral activity. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide, and at the 2-position by requiring an oxygen linked substituent.
U.K. Patent Application 1,191,443 discloses quinoline derivatives that are reported to possess antiviral activity. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein by not including a 4-substitutedbenzamide at the 3-position, and by requiring a fused furan heterocyclic ring at the 5,6-, 6,7-, or 7,8-position of the quinolone.
WO 97/14682 discloses quinoline derivatives that are reported to be useful to treat specific hormone dependent diseases. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide, at the 1-position, by requiring a halogenoaralkyl, and at the 7-position by requiring an acylaminoaryl group.
U.S. Pat. No. 4,786,644, discloses 1-aryl-3-quinolinecarboxamides that are reported to be useful to treat pain and inflammation. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide, and at the 1-position by requiring an optionally substituted phenyl substituent.
U.S. Pat. No. 4,835,163, discloses N-alkoxyalkyl derivatives of quinolone carboxamides that are reported to possess anticonvulsive and psychotonic activity. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide substituent.
U.S. Pat. No. 5,096,901; U.K. Application Number 2 236 751; and T. J. Ward et al.,
Med. Chem. Res.
(1993), 4, 267-272 disclose quinolone-3-(azabicyclo)carboxamides that are reported to possess 5-HT3 activity and to be useful to treat neuro-psychiatric disorders. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein by requiring an azabicyclo containing substituent at the 3-position.
JP 02124871 discloses quinolone compounds that are reported to possess 5-lipoxygenase activity. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide substituent.
EP 0 332 930A2, discloses quinolone compounds that are reported to possess antibacterial antiviral activity. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide, and at the 6-position by requiring a hydrogen, halo, or nitro substituent.
Chem. Abstracts (1969), 71, 101735q, discloses quinolone compounds that are reported to possess antiinflamatory activity. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide substituent.
U.S. Pat. Nos. 5,051,418 and 4,908,366, disclose 8-cyano-quinolone compounds that are reported to possess antibacterial activity. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide, and at the 8-position by requiring a cyano substituent.
EP 0 370 686, discloses a process for preparing quinolone carboxylic acid intermediates. The structure of the disclosed compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide, and at the 6-position by requiring a fluoro substituent.
U.S. Pat. No. 4,621,088, discloses quinolone amino acid derivatives that are reported to possess antiallergic activity, central nervous system activity and cardiovascular activity. The structure of these compounds differs from the structure of the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide.
U.S. Pat. No. 5,328,887 discloses an array of compounds including numerous quinolone compounds that are reported to be useful as fluorescent donor elements for use in a thermal transfer possess. The single specific 4-quinolone compound prepared and tested in the application differs from the compounds of formula I disclosed herein at the 3-position by not including a 4-substitutedbenzamide, at the 2-position by having a phenyl substituent, at the 6-position by having a hydrogen, and at the 1-position by being unsubstituted.
U.S. Pat. No. 4,855,291, discloses quinolone compounds that are reported to possess antihypertensive activity. The structure of these compounds differs from the structure
Schnute Mark E.
Strohbach Joseph Walter
Thaisrivongs Suvit
Tucker John Alan
Turner Steven Ronald
Pharmacia & Upjohn Company
Seaman D. Margaret
Yang Lucy X.
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