US4774246A
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Quinoline antibacterial compounds
Assignee: Abbott Laboratories
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Filing: 1986-09-12
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Granted: 1988-09-27
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Expires: 2006-09-12
Abstract
Abstract Quinoline compounds having the formula: <IMAGE> wherein R is a phenyl or substituted phenyl group or an aromatic heterocyclic group, R1 is a hydrogen or a carboxy-protecting group and Z is an amine group or an aliphatic heterocyclic group. The compounds have antibacterial activity.
Inventors
- 👤 Daniel T. Chu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 03:04
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56; C07D405/00; C07D405/02; C07D405/04; C07D409/00; C07D409/02; C07D409/04; C07D417/00; C07D417/02; C07D417/04; C07D491/00; C07D491/02; C07D491/04; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
333 words
A compound having the formula: ##STR53## wherein R 1 is hydrogen or a carboxy protecting group; R is phenyl having the formula: ##STR54## wherein R 2 is methylenedioxy or one or two substituents independently selected from hydrogen, halogen, nitro, carboxyl, cyano, C 1 to C 6 alkyl, hydroxy-substituted C 1 to C 6 alkyl, halo substituted C 1 to C 6 alkyl, a substituent having the formula: --Y--R.sub.3 wherein --Y-- is --O-- or --S-- and R 3 is hydrogen or C 1 to C 6 alkyl, and a substituent of the formula: ##STR55## wherein R 4 and R 5 are independently hydrogen or C 1 or C 6 alkyl; and, Z is selected from (1) an aliphatic heterocyclic ring having the structure: ##STR56## wherein R 8 is CH 2 , (CH 2 ) 2 , or -CH 2 R 9 (CH 2 ) n - wherein R 9 is selected from the group consisting of --S, --O-- and --N-- and n is O or 1; (2) substituted derivatives of said aliphatic heterocyclic ring having one or two substitutents independently selected from C 1 to C 6 alkyl, C 1 to C 6 hydroxyalkyl, hydroxy, alkanoyl having 1 to 6 carbon atoms, alkanoylamino having 1 to 6 carbon atoms and a substituent of the formula: ##STR57## wherein R 10 and R 11 are each independently selected from hydrogen, C 1 to C 6 alkyl, halo-substituted C 1 to C 6 alkyl and hydroxy-substituted C 1 to C 6 alkyl; and (3) a substituent of the formula: ##STR58## wherein R 6 is hydrogen, C 1 to C 10 alkyl, halo-substituted C 1 to C 10 alkyl or hydroxy-substituted C 1 to C 10 alkyl, and R 7 is selected from C 1 to C 10 alkyl, halo-substituted C 1 to C 10 alkyl, hydroxy-substituted C 1 to C 10 alkyl, --NH 2 , a mono-(C 1 to C 6 ) alkylamino and a di-(C 1 to C 6 ) alkylamino; and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
333 words
A compound having the formula: ##STR53## wherein R 1 is hydrogen or a carboxy protecting group; R is phenyl having the formula: ##STR54## wherein R 2 is methylenedioxy or one or two substituents independently selected from hydrogen, halogen, nitro, carboxyl, cyano, C 1 to C 6 alkyl, hydroxy-substituted C 1 to C 6 alkyl, halo substituted C 1 to C 6 alkyl, a substituent having the formula: --Y--R.sub.3 wherein --Y-- is --O-- or --S-- and R 3 is hydrogen or C 1 to C 6 alkyl, and a substituent of the formula: ##STR55## wherein R 4 and R 5 are independently hydrogen or C 1 or C 6 alkyl; and, Z is selected from (1) an aliphatic heterocyclic ring having the structure: ##STR56## wherein R 8 is CH 2 , (CH 2 ) 2 , or -CH 2 R 9 (CH 2 ) n - wherein R 9 is selected from the group consisting of --S, --O-- and --N-- and n is O or 1; (2) substituted derivatives of said aliphatic heterocyclic ring having one or two substitutents independently selected from C 1 to C 6 alkyl, C 1 to C 6 hydroxyalkyl, hydroxy, alkanoyl having 1 to 6 carbon atoms, alkanoylamino having 1 to 6 carbon atoms and a substituent of the formula: ##STR57## wherein R 10 and R 11 are each independently selected from hydrogen, C 1 to C 6 alkyl, halo-substituted C 1 to C 6 alkyl and hydroxy-substituted C 1 to C 6 alkyl; and (3) a substituent of the formula: ##STR58## wherein R 6 is hydrogen, C 1 to C 10 alkyl, halo-substituted C 1 to C 10 alkyl or hydroxy-substituted C 1 to C 10 alkyl, and R 7 is selected from C 1 to C 10 alkyl, halo-substituted C 1 to C 10 alkyl, hydroxy-substituted C 1 to C 10 alkyl, --NH 2 , a mono-(C 1 to C 6 ) alkylamino and a di-(C 1 to C 6 ) alkylamino; and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
27 words
A compound as defined in claim 1 wherein the aliphatic heterocyclic ring is selected from the group consisting of azetidinyl, piperazinyl piperidinyl, pyrrolidinyl, morpholino, thiomorpholino and homopiperazinyl.
Claim 4
Dependent Claim
12 words
A compound as defined in claim 1 wherein R 1 is hydrogen.
Claim 5
Dependent Claim
72 words
A compound as defined in claim 1 wherein Z is an amino group having the formula: ##STR59## wherein R 6 is hydrogen, C 1 -C 10 alkyl, halo-substituted C 1 -C 10 alkyl, hydroxy-substituted C 1 -C 10 alkyl and R 7 is C 1 -C 10 alkyl, halo-substituted C 1 -C 10 alkyl, hydroxy-substituted C 1 -C 10 alkyl, amino, mono-(C 1 -C 4 )alkylamino or di(C 1 -C 4 )alkylamino.
Claim 6
Dependent Claim
58 words
A compound having the formula: ##STR60## wherein Z is piperazinyl or C 1 to C 6 alkyl-substituted piperazinyl, or 4-acetylpiperazinyl, and R is phenyl or substituted phenyl wherein the substitutent on the phenyl group is methylenedioxy or one or two substituents independently selected from C 1 to C 6 alkyl, halo and hydroxy, and pharmaceutically acceptable salts thereof.
Claim 7
Dependent Claim
58 words
A compound having the formula: ##STR60## wherein Z is piperazinyl or C 1 to C 6 alkyl-substituted piperazinyl, or 4-acetylpiperazinyl, and R is phenyl or substituted phenyl wherein the substitutent on the phenyl group is methylenedioxy or one or two substituents independently selected from C 1 to C 6 alkyl, halo and hydroxy, and pharmaceutically acceptable salts thereof.
Claim 8
Dependent Claim
11 words
A compound as defined in claim 1 wherein R is O,p-difluorophenyl.
Claim 9
Dependent Claim
11 words
A compound as defined in claim 6 wherein Z is 4-methyl-1-piperazinyl.
Claim 10
Dependent Claim
11 words
A compound as defined in claim 1 wherein R is p-fluorophenyl.
Claim 11
Dependent Claim
11 words
A compound as defined in claim 1 wherein Z in 3-aminopyrrolidin-1-yl.
Claim 12
Dependent Claim
19 words
A compound as defined in claim 5 wherein R is phenyl, Z is piperazinyl and R 1 is hydrogen.
Claim 13
Dependent Claim
19 words
A compound as defined in claim 5 wherein R is phenyl, Z is 4-methylpiperazinyl and R 1 is hydrogen.
Claim 14
Dependent Claim
19 words
A compound as defined in claim 5 wherein R is fluorophenyl, Z is piperazinyl and R 1 is hydrogen.
Claim 15
Dependent Claim
19 words
A compound as defined in claim 5 wherein R is fluorophenyl, Z is 4-methylpiperazinyl and R 1 is hydrogen.
Claim 16
Dependent Claim
19 words
A compound as defined in claim 5 wherein R is hydroxyphenyl, Z is piperazinyl and R 1 is hydrogen.
Claim 17
Dependent Claim
19 words
A compound as defined in claim 5 wherein R is fluorophenyl, Z is 4-acetylpiperazinyl and R 1 is hydrogen.
Claim 18
Dependent Claim
20 words
A composition having antibacterial activity in pharmaceutical dosage form containing a diluent and a compound as defined in claim 1.
Claim 19
Dependent Claim
20 words
A composition having antibacterial activity in pharmaceutical dosage form containing a diluent and a compound as defined in claim 5.
Claim 20
Dependent Claim
29 words
A method of treating a bacterial infection in a patient comprising administering to a patient in need a therapeutically effective amount of a compound as defined in claim 1.
Claim 21
Dependent Claim
29 words
A method of treating a bacterial infection in a patient comprising administering to a patient in need a therapeutically effective amount of a compound as defined in claim 5.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-09-27 | 1992-03-28 | 1992-09-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-09-27 | 1996-03-28 | 1996-09-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-09-27 | 2000-03-28 | 2000-09-27 | $7700.00 | Window Closed / Lapsed |