US4730000A
Expired / Lapsed
US
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Quinoline antibacterial compounds
Assignee: Abbott Laboratories
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Filing: 1985-10-04
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Granted: 1988-03-08
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Expires: 2005-10-04
Abstract
Abstract Quinoline compounds having the formula: <IMAGE> wherein R is a phenyl group or an aromatic heterocyclic group, Z is an aliphatic heterocyclic group or an amine, and R1 is hydrogen or a carboxy-protecting group. The compounds here disclosed have antibacterial properties.
Inventors
- 👤 Daniel T. Chu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 09:19
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D401/00; C07D401/02; C07D401/04; C07D405/00; C07D405/02; C07D405/04; C07D409/00; C07D409/02; C07D409/04; C07D417/00; C07D417/02; C07D417/04; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
368 words
A compound having the formula: ##STR75## wherein R 1 is hydrogen or a carboxy protecting group; R is selected from the group consisting of (1) an aromatic heterocyclic ring having 5 to 6 atoms therein, with 1 to 2 hetero atoms being selected from the group consisting of S, O and N and the remaining atoms in the ring being carbon atoms and substituted derivatives of said aromatic heterocyclic ring wherein the aromatic heterocyclic ring is mono-substituted with C 1 to C 6 alkyl; and (2) a phenyl group having the formula: ##STR76## wherein R 2 is one, two or three substituents independently selected from the group consisting of hydrogen, halogen, cyano, C 1 to C 6 alkyl, halo-substituted C 1 to C 6 alkyl, a group having the formula: --Y--R.sub.3 wherein --Y-- is --O-- or --S-- or R 3 is hydrogen or C 1 to C 6 alkyl, and NH 2 ; and Z is selected from the group consisting of (1) an aliphatic heterocyclic ring having the structure: ##STR77## wherein R 8 is CH 2 , (CH 2 ) 2 or a group of the formula --(CH 2 ) n --R 9 -- wherein R 9 is --N--, --O--, or --S-- and n is 0, 1 or 2, and substituted derivatives thereof wherein the aliphatic heterocyclic ring is substituted with one, two or three substituents independently selected from the group consisting of C 1 to C 6 alkyl, C 1 to C 3 alkylamino-substituted C 1 to C 6 alkyl, amino-substituted C 1 to C 6 alkyl, hydroxy, alkanoyl having 1 to 6 carbon atoms, alkanoylamido having 1 to 6 carbon atoms, halogen, an amine of the formula: ##STR78## wherein R 10 and R 11 are each independently selected from the group consisting of hydrogen and C 1 to C 6 alkyl; and (2) an amino group of the formula: ##STR79## wherein R 6 is hydrogen or C 1 to C 6 alkyl, and R 7 is selected from the group consisting of C 1 to C 6 alkyl, NH 2 , a mono-(C 1 to C 4 ) alkylamino group and a di-(C 1 to C 4 ) alkylamino group, and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
368 words
A compound having the formula: ##STR75## wherein R 1 is hydrogen or a carboxy protecting group; R is selected from the group consisting of (1) an aromatic heterocyclic ring having 5 to 6 atoms therein, with 1 to 2 hetero atoms being selected from the group consisting of S, O and N and the remaining atoms in the ring being carbon atoms and substituted derivatives of said aromatic heterocyclic ring wherein the aromatic heterocyclic ring is mono-substituted with C 1 to C 6 alkyl; and (2) a phenyl group having the formula: ##STR76## wherein R 2 is one, two or three substituents independently selected from the group consisting of hydrogen, halogen, cyano, C 1 to C 6 alkyl, halo-substituted C 1 to C 6 alkyl, a group having the formula: --Y--R.sub.3 wherein --Y-- is --O-- or --S-- or R 3 is hydrogen or C 1 to C 6 alkyl, and NH 2 ; and Z is selected from the group consisting of (1) an aliphatic heterocyclic ring having the structure: ##STR77## wherein R 8 is CH 2 , (CH 2 ) 2 or a group of the formula --(CH 2 ) n --R 9 -- wherein R 9 is --N--, --O--, or --S-- and n is 0, 1 or 2, and substituted derivatives thereof wherein the aliphatic heterocyclic ring is substituted with one, two or three substituents independently selected from the group consisting of C 1 to C 6 alkyl, C 1 to C 3 alkylamino-substituted C 1 to C 6 alkyl, amino-substituted C 1 to C 6 alkyl, hydroxy, alkanoyl having 1 to 6 carbon atoms, alkanoylamido having 1 to 6 carbon atoms, halogen, an amine of the formula: ##STR78## wherein R 10 and R 11 are each independently selected from the group consisting of hydrogen and C 1 to C 6 alkyl; and (2) an amino group of the formula: ##STR79## wherein R 6 is hydrogen or C 1 to C 6 alkyl, and R 7 is selected from the group consisting of C 1 to C 6 alkyl, NH 2 , a mono-(C 1 to C 4 ) alkylamino group and a di-(C 1 to C 4 ) alkylamino group, and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
36 words
A compound as defined in claim 1 wherein the aliphatic heterocyclic ring is selected from the group consisting of piperazinyl groups, piperidinyl groups, pyrrolidinyl groups, morpholino groups, thiomorpholino groups and homopiperazinyl groups and substituted derivatives thereof.
Claim 4
Dependent Claim
24 words
A compound as defined in claim 1 wherein the aromatic heterocyclic group is selected from the group consisting of pyridyl, pyrazinyl, thiazoyl, furyl, thienyl.
Claim 5
Dependent Claim
12 words
A compound as defined in claim 1 wherein R 1 is hydrogen.
Claim 6
Dependent Claim
61 words
A compound as defined in claim 1 wherein Z is an amino group having the formula: ##STR80## wherein R 6 is hydrogen or C 1 to C 6 alkyl, and R 7 is C 1 to C 6 alkyl, NH 2 , a mono-(C 1 to C 4 ) alkylamino group or a di-(C 1 to C 4 ) alkylamino group.
Claim 7
Dependent Claim
131 words
A compound having the formula: ##STR81## wherein Z is (1) mono- or di-substituted pyrrolidinyl wherein the substituent is independently selected from NH 2 , C 1 to C 3 alkyl, halogen, amino-substituted C 1 to C 6 alkyl and C 1 to C 3 alkylamino-substituted C 1 to C 6 alkyl, or (2) piperazinyl or substituted piperazinyl wherein the piperazinyl ring is substituted with one, two or three substituents independently selected from C 1 to C 6 alkyl, or C 1 to C 6 alkanoyl; R 1 is hydrogen or a carboxy protecting group, and R is phenyl or substituted phenyl wherein the phenyl ring is substituted with one, two or three substituents independently selected from C 1 to C 6 alkyl, halogen, methylenedioxy and hydroxy and pharmaceutically acceptable salts thereof.
Claim 8
Dependent Claim
131 words
A compound having the formula: ##STR81## wherein Z is (1) mono- or di-substituted pyrrolidinyl wherein the substituent is independently selected from NH 2 , C 1 to C 3 alkyl, halogen, amino-substituted C 1 to C 6 alkyl and C 1 to C 3 alkylamino-substituted C 1 to C 6 alkyl, or (2) piperazinyl or substituted piperazinyl wherein the piperazinyl ring is substituted with one, two or three substituents independently selected from C 1 to C 6 alkyl, or C 1 to C 6 alkanoyl; R 1 is hydrogen or a carboxy protecting group, and R is phenyl or substituted phenyl wherein the phenyl ring is substituted with one, two or three substituents independently selected from C 1 to C 6 alkyl, halogen, methylenedioxy and hydroxy and pharmaceutically acceptable salts thereof.
Claim 9
Dependent Claim
19 words
A compound as defined in claim 6 wherein R is phenyl, Z is piperazinyl and R 1 is hydrogen.
Claim 10
Dependent Claim
19 words
A compound as defined in claim 6 wherein R is phenyl, Z is 4-methylpiperazinyl and R 1 is hydrogen.
Claim 11
Dependent Claim
19 words
A compound as defined in claim 6 wherein R is p-fluorophenyl, Z is piperazinyl and R 1 is hydrogen.
Claim 12
Dependent Claim
19 words
A compound as defined in claim 6 wherein R is p-fluorophenyl, Z is 4-methyl-1-piperazinyl and R 1 is hydrogen.
Claim 13
Dependent Claim
19 words
A compound as defined in claim 6 wherein R is p-fluorophenyl, Z is 3-methyl-1-piperazinyl and R 1 is hydrogen.
Claim 14
Dependent Claim
19 words
A compound as defined in claim 6 wherein R is p-fluorophenyl, Z is 3-amino-1-pyrrolidinyl and R 1 is hydrogen.
Claim 15
Dependent Claim
19 words
A compound as defined in claim 6 wherein Z is 3-amino-4-methyl-1-pyrrolidinyl, R is p-fluorophenyl and R 1 is hydrogen.
Claim 16
Dependent Claim
19 words
A compound as defined in claim 6 wherein Z is cis-3-aminomethyl-4-chloro-1-pyrrolidinyl, R is p-fluorophenyl and R 1 is hydrogen.
Claim 17
Dependent Claim
19 words
A compound as defined in claim 6 wherein Z is 3-ethylaminomethyl-1-pyrrolidinyl, R is p-fluorophenyl and R 1 is hydrogen.
Claim 18
Dependent Claim
19 words
A compound as defined in claim 6 wherein Z is piperazinyl, R is 2,4-difluorophenyl and R 1 is hydrogen.
Claim 19
Dependent Claim
19 words
A compound as defined in claim 6 wherein Z is 4-methyl-1-piperazinyl, R is 2,4-difluorophenyl and R 1 is hydrogen.
Claim 20
Dependent Claim
19 words
A compound as defined in claim 6 wherein Z is 3-methyl-1-piperazinyl, R is 2,4-difluorophenyl and R 1 is hydrogen.
Claim 21
Dependent Claim
19 words
A compound as defined in claim 6 wherein Z is 3-amino-1-pyrrolidinyl, R is 2,4-difluorophenyl and R 1 is hydrogen.
Claim 22
Dependent Claim
19 words
A compound as defined in claim 6 wherein Z is 3-amino-4-methyl-1-pyrrolidinyl, R is 2,4-difluorophenyl and R 1 is hydrogen.
Claim 23
Dependent Claim
19 words
A compound as defined in claim 6 wherein Z is cis-3-aminomethyl-4-chloro-1-pyrrolidinyl, R is 2,4-difluorophenyl and R 1 is hydrogen.
Claim 24
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 25
Dependent Claim
20 words
A composition having antibacterial activity in pharmaceutical dosage form containing a diluent and a compound as defined in claim 6.
Claim 26
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 27
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 6.
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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) | 1991-03-08 | 1991-09-07 | 1992-03-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-03-08 | 1995-09-07 | 1996-03-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-03-08 | 1999-09-07 | 2000-03-08 | $7700.00 | Window Closed / Lapsed |