US4533663A
Expired / Lapsed
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Quino-benzothiazine antibacterial compounds
Assignee: Abbott Laboratories
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Filing: 1984-04-26
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Granted: 1985-08-06
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Expires: 2004-04-26
Abstract
Abstract Quino-benzothiazine compounds having the formula ##STR1## wherein R 2 is one or more constituents; R 1 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
2026-10-27 20:13
CPC Classifications
C; C07; C07D; C07D513/00; C07D513/02; C07D513/06; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
337 words
A compound having the formula ##STR43## wherein R 1 is hydrogen or a carboxy protecting group; R 2 is one or more groups selected from the group consisting of hydrogen, halogen, nitro, carboxyl, methylenedioxy, cyano, C 1 to C 6 alkyl halo-substituted C 1 to C 6 alkyl, hydroxy-substituted C 1 to C 6 alkyl, a group 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 an amine group having the formula: ##STR44## wherein R 4 and R 5 are independently hydrogen or C 1 to C 6 alkyl; and Z is selected from the group consisting of an aliphatic heterocyclic ring having the structure ##STR45## wherein R 8 is methylene, dimethylene or a group of the formula --CH 2 --CH 2 --R 9 --CH 2 or --CH 2 --R 9 --CH 2 -- wherein R 9 is selected from the group consisting of --S--, --O-- and --N--; substituted derivatives thereof having one or more substitutents selected from the group consisting of C 1 to C 6 alkyl, C 1 to C 6 hydroxyalkyl, hydroxy, alkanoyl contaning 1 to 6 carbon atoms, alkanoylamido containing 1 to 6 carbon atoms and an amine of the formula ##STR46## wherein R 10 and R 11 are each independently selected from the group consisting of 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 an amino group of the formula ##STR47## wherein R 6 is hydrogen or 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 the group consisting of C 1 to C 10 alkyl, halo-substituted C 1 to C 10 alkyl, hydroxy-substituted C 1 to C 10 alkyl, an amine group, a mono-(C 1 to C 6 )alkylamino group and a di-(C 1 to C 6 )alkylamino group, and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
337 words
A compound having the formula ##STR43## wherein R 1 is hydrogen or a carboxy protecting group; R 2 is one or more groups selected from the group consisting of hydrogen, halogen, nitro, carboxyl, methylenedioxy, cyano, C 1 to C 6 alkyl halo-substituted C 1 to C 6 alkyl, hydroxy-substituted C 1 to C 6 alkyl, a group 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 an amine group having the formula: ##STR44## wherein R 4 and R 5 are independently hydrogen or C 1 to C 6 alkyl; and Z is selected from the group consisting of an aliphatic heterocyclic ring having the structure ##STR45## wherein R 8 is methylene, dimethylene or a group of the formula --CH 2 --CH 2 --R 9 --CH 2 or --CH 2 --R 9 --CH 2 -- wherein R 9 is selected from the group consisting of --S--, --O-- and --N--; substituted derivatives thereof having one or more substitutents selected from the group consisting of C 1 to C 6 alkyl, C 1 to C 6 hydroxyalkyl, hydroxy, alkanoyl contaning 1 to 6 carbon atoms, alkanoylamido containing 1 to 6 carbon atoms and an amine of the formula ##STR46## wherein R 10 and R 11 are each independently selected from the group consisting of 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 an amino group of the formula ##STR47## wherein R 6 is hydrogen or 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 the group consisting of C 1 to C 10 alkyl, halo-substituted C 1 to C 10 alkyl, hydroxy-substituted C 1 to C 10 alkyl, an amine group, a mono-(C 1 to C 6 )alkylamino group and a di-(C 1 to C 6 )alkylamino group, and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
34 words
A compound as defined in claim 1 wherein the aliphatic heterocyclic ring is selected from the group consisting of azetidinyl groups, piperazinyl groups, piperidinyl groups, pyrrolidinyl groups, morpholino groups, thiomorpholino groups and homopiperazinyl groups.
Claim 4
Dependent Claim
12 words
A compound as defined in claim 1 wherein R 1 is hydrogen.
Claim 5
Dependent Claim
84 words
A compound as defined in claim 1 wherein Z is an amino group having the formula: ##STR48## wherein R 6 is hydrogen, C 1 -C 10 alkyl, halo-substituted C 1 to C 10 alkyl, or hydroxy-substituted C 1 to C 10 alkyl, and R 7 is C 1 -C 10 alkyl, halo-substituted C 1 to C 10 alkyl, or hydroxy-substituted C 1 to C 10 alkyl, an amino group, a mono-(C 1 -C 4 )alkylamino group or a di(C 1 -C 4 )-alkylamino group.
Claim 6
Dependent Claim
59 words
A compound having the formula: ##STR49## wherein Z is piperazinyl or piperazinyl substituted with a C 1 to C 6 alkyl, or 4-acylpiperazinyl, or 3-amino-pyrrolidinyl or 3-C 1 to C 6 alkylamino-pyrrolidinyl; and R 2 is one or more of hydrogen, an alkyl group, a halogen group, a hydroxy group, and a methylenedioxy group, and pharmaceutically acceptable salts thereof.
Claim 7
Dependent Claim
59 words
A compound having the formula: ##STR49## wherein Z is piperazinyl or piperazinyl substituted with a C 1 to C 6 alkyl, or 4-acylpiperazinyl, or 3-amino-pyrrolidinyl or 3-C 1 to C 6 alkylamino-pyrrolidinyl; and R 2 is one or more of hydrogen, an alkyl group, a halogen group, a hydroxy group, and a methylenedioxy group, and pharmaceutically acceptable salts thereof.
Claim 8
Dependent Claim
20 words
A compound as defined in claim 5 wherein R 2 is hydrogen, Z is piperazinyl and R 1 is hydrogen.
Claim 9
Dependent Claim
20 words
A compound as defined in claim 5 wherein R 2 is hydrogen, Z is 4-methylpiperazinyl and R 1 is hydrogen.
Claim 10
Dependent Claim
20 words
A compound as defined in claim 5 wherein R 2 is 10-fluoro, Z is piperazinyl and R 1 is hydrogen.
Claim 11
Dependent Claim
20 words
A compound as defined in claim 5 wherein R 2 is 10-fluoro, Z is 4-methylpiperazinyl and R 1 is hydrogen.
Claim 12
Dependent Claim
20 words
A compound as defined in claim 5 wherein R 2 is hydrogen, Z is 3-aminopyrrolidinyl and R 1 is hydrogen.
Claim 13
Dependent Claim
20 words
A compound as defined in claim 5 wherein R 2 is 10-fluoro, Z is 3-aminopyrrolidinyl and R 1 is hydrogen.
Claim 14
Dependent Claim
20 words
A compound as defined in claim 5 wherein R 2 is hydrogen, Z is 3-methylaminopyrrolidinyl and R 1 is hydrogen.
Claim 15
Dependent Claim
20 words
A compound as defined in claim 5 wherein R 2 is 10-fluoro, Z is 3-dimethylaminopyrrolidinyl and R 1 is hydrogen.
Claim 16
Dependent Claim
20 words
A compound as defined in claim 5 wherein R 2 is 10-hydroxy, Z is piperazinyl and R 1 is hydrogen.
Claim 17
Dependent Claim
20 words
A compound as defined in claim 5 wherein R 2 is 8,10-difluoro, Z is 4-methylpiperazinyl 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
32 words
A method of treating a bacterial infection in a patient comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound as defined in claim 1.
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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) | 1988-08-05 | 1989-02-04 | 1989-08-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-05 | 1993-02-04 | 1993-08-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-05 | 1997-02-04 | 1997-08-06 | $7700.00 | Window Closed / Lapsed |