US4416884A
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Piperazinylbenzoheterocyclic compounds
Assignee: Otsuka Pharmaceutical Co Ltd
•
Filing: 1980-10-09
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Granted: 1983-11-22
•
Expires: 2000-10-09
Abstract
Abstract A piperazinylbenzoheterocyclic compound having antimicrobial properties and represented by the formula (I) ##STR1## wherein R 1 represents hydrogen or lower alkyl; R 2 represents hydrogen; R 3 represents hydrogen, lower alkyl, lower alkanoyl, lower alkylsulfonyl, phenylalkyl, benzoyl, p-toluenesulfonyl, a group represented by the formula ##STR2## lower alkyl substituted with one to three of halogen and hydroxy, lower alkanoyl substituted with one to seven of halogen, phenylalkyl substituted with one to three of lower alkoxy on the phenyl ring, lower alkylsulfonyl substituted with one to three of halogen, lower alkenyl or lower alkynyl; R 4 represents hydrogen or halogen, and n is an integer of 0 or 1, except that when n is 0, R 1 and R 2 together can represent the atoms necessary to form a cyclohexane ring, and when R 3 represents lower alkyl substituted with one to three of halogen and hydroxy, lower alkanoyl substituted with one to seven of halogen, phenylalkyl substituted with one to three of lower alkoxy on the phenyl ring, lower alkylsulfonyl substituted with one to three of halogen, lower alkenyl or lower alkynyl, n is 1.
Inventors
- 👤 Hiroshi Ishikawa
- 👤 Fujio Tabusa
- 👤 Kazuyuki Nakagawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 22:33
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; C07D215/227; C07D209/00; C07D209/02; C07D209/04; C07D209/08; C07D209/56; C07D209/80; C07D209/82; C07D209/88; C07D215/04; C07D215/06; C07D215/18; C07D455/00; C07D455/03; C07D455/04; C07D471/00; C07D471/02; C07D471/06; C07D499/00
Claims Analysis
Total Claims: 66
Claim 1
Independent Claim
216 words
A piperazinylbenzoheterocyclic compound represented by the formula (I) ##STR28## wherein R 1 represents hydrogen or lower alkyl; R 2 represents hydrogen; R 3 represents hydrogen, lower alkyl, lower alkanoyl, lower alkylsulfonyl, phenylalkyl wherein the alkyl moiety contains 1 to 4 carbon atoms, benzoyl, p-toluenesulfonyl, a group represented by the formula ##STR29## lower alkyl substituted with one to three of halogen and hydroxy, lower alkanoyl substituted with one to seven of halogen selected from the group consisting of fluorine, chlorine and bromine, phenylalkyl substituted with one to three of lower alkoxy on the phenyl ring, lower alkylsulfonyl substituted with one to three of halogen, lower alkenyl or lower alkynyl; R 4 represents hydrogen or halogen, and n is an integer of 0 or 1, except that when n is 0, R 1 and R 2 together can represent the atoms necessary to form a cyclohexane ring, and when R 3 represents lower alkyl substituted with one to three of halogen and hydroxy, lower alkanoyl substituted with one to seven of halogen selected from the group consisting of fluorine, chlorine and bromine, phenylalkyl substituted with one to three of lower alkoxy on the phenyl ring, lower alkylsulfonyl substituted with one to three of halogen, lower alkenyl or lower alkynyl, n is 1; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
216 words
A piperazinylbenzoheterocyclic compound represented by the formula (I) ##STR28## wherein R 1 represents hydrogen or lower alkyl; R 2 represents hydrogen; R 3 represents hydrogen, lower alkyl, lower alkanoyl, lower alkylsulfonyl, phenylalkyl wherein the alkyl moiety contains 1 to 4 carbon atoms, benzoyl, p-toluenesulfonyl, a group represented by the formula ##STR29## lower alkyl substituted with one to three of halogen and hydroxy, lower alkanoyl substituted with one to seven of halogen selected from the group consisting of fluorine, chlorine and bromine, phenylalkyl substituted with one to three of lower alkoxy on the phenyl ring, lower alkylsulfonyl substituted with one to three of halogen, lower alkenyl or lower alkynyl; R 4 represents hydrogen or halogen, and n is an integer of 0 or 1, except that when n is 0, R 1 and R 2 together can represent the atoms necessary to form a cyclohexane ring, and when R 3 represents lower alkyl substituted with one to three of halogen and hydroxy, lower alkanoyl substituted with one to seven of halogen selected from the group consisting of fluorine, chlorine and bromine, phenylalkyl substituted with one to three of lower alkoxy on the phenyl ring, lower alkylsulfonyl substituted with one to three of halogen, lower alkenyl or lower alkynyl, n is 1; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
16 words
A piperazinylbenzoheterocyclic compound or pharmaceutically acceptable salt thereof as in claim 1 wherein n is 1.
Claim 4
Dependent Claim
18 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 2 wherein R 4 represents halogen.
Claim 5
Dependent Claim
20 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 3 wherein R 4 represents chlorine or fluorine.
Claim 6
Dependent Claim
25 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 4 wherein R 1 represents alkyl having from 1 to 4 carbon atoms.
Claim 7
Dependent Claim
35 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 5 wherein R 3 represents hydrogen, alkyl having from 1 to 4 carbon atoms or alkanoyl having from 1 to 4 carbon atoms.
Claim 8
Dependent Claim
49 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 5 wherein R 3 represents alkylsulfonyl having from 1 to 4 carbon atoms, phenylalkyl consisting of phenyl and alkyl having from 1 to 4 carbon atoms, benzoyl group, p-toluenesulfonyl or a group represented by the formula ##STR30##
Claim 9
Dependent Claim
52 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 5 wherein R 3 represents alkyl having from 1 to 4 carbon atoms substituted with from 1 to 3 of halogen and hydroxy or alkanoyl having from 1 to 4 carbon atoms substituted with from 1 to 7 of halogen.
Claim 10
Dependent Claim
79 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 5 wherein R 3 represents phenylalkyl consisting of phenyl substituted with from 1 to 3 of alkoxy each having from 1 to 4 carbon atoms and alkylene having from 1 to 4 carbon atoms, alkylsulfonyl having from 1 to 4 carbon atoms substituted with from 1 to 3 of halogen, alkenyl having from 2 to 4 carbon atoms, or alkynyl having from 2 to 4 carbon atoms.
Claim 11
Dependent Claim
18 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 4 wherein R 1 represents hydrogen.
Claim 12
Dependent Claim
35 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 10 wherein R 3 represents hydrogen, alkyl having from 1 to 4 carbon atoms, or alkanoyl having from 1 to 4 carbon atoms.
Claim 13
Dependent Claim
18 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 2 wherein R 4 represents hydrogen.
Claim 14
Dependent Claim
25 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 12 wherein R 1 represents alkyl having from 1 to 4 carbon atoms.
Claim 15
Dependent Claim
35 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 13 wherein R 3 represents hydrogen, alkyl having from 1 to 4 carbon atoms or alkanoyl having from 1 to 4 carbon atoms.
Claim 16
Dependent Claim
18 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 12 wherein R 1 represents hydrogen.
Claim 17
Dependent Claim
29 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 1 wherein n is 0, R 1 represents hydrogen or lower alkyl, and R 2 represents hydrogen.
Claim 18
Dependent Claim
18 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 16 wherein R 4 represents halogen.
Claim 19
Dependent Claim
25 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 17 wherein R 1 represents alkyl having from 1 to 4 carbon atoms.
Claim 20
Dependent Claim
35 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 18 wherein R 3 represents hydrogen, alkyl having from 1 to 4 carbon atoms, or alkanoyl having from 1 to 4 carbon atoms.
Claim 21
Dependent Claim
52 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 18 wherein R 3 represents alkylsulfonyl having from 1 to 4 carbon atoms, phenylalkyl consisting of phenyl and alkylene having from 1 to 4 carbon atoms, a benzoyl group, a p-toluenesulfonyl group or a group represented by the formula ##STR31##
Claim 22
Dependent Claim
18 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 17 wherein R 1 represents hydrogen.
Claim 23
Dependent Claim
35 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 21 wherein R 3 represents hydrogen, alkyl having from 1 to 4 carbon atoms, or alkanoyl having from 1 to 4 carbon atoms.
Claim 24
Dependent Claim
18 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 16 wherein R 4 represents hydrogen.
Claim 25
Dependent Claim
25 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 23 wherein R 1 represents alkyl having from 1 to 4 carbon atoms.
Claim 26
Dependent Claim
35 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 24 wherein R 3 represents hydrogen, alkyl having from 1 to 4 carbon atoms, or alkanoyl having from 1 to 4 carbon atoms.
Claim 27
Dependent Claim
18 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 23 wherein R 1 represents hydrogen.
Claim 28
Dependent Claim
33 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 1 wherein n is 0 and R 1 and R 2 together represent the atoms necessary to form a cyclohexane ring.
Claim 29
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 14 wherein said compound is 8-(1-piperazinyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 30
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 25 wherein said compound is 9-(1-piperazinyl)-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid.
Claim 31
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 15 wherein said compound is 8-(1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 32
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 26 wherein said compound is 9-(1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid.
Claim 33
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 27 wherein said compound is 1-(1-piperazinyl)-7a,8,9,10,11,11a-hexahydro-4H-pyrido[3,2,1-jk]carbazole-4-oxo-5-carboxylic acid.
Claim 34
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 6 wherein said compound is 8-(1-piperazinyl)-9-fluoro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 35
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 6 wherein said compound is 8-(1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 36
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 6 wherein said compound is 8-(4-methyl-1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid.
Claim 37
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 6 wherein said compound is 8-(4-formyl-1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid.
Claim 38
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 6 wherein said compound is 8-(4-methyl-1-piperazinyl)-9-fluoro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid.
Claim 39
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 6 wherein said compound is 8-(4-formyl-1-piperazinyl)-9-fluoro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid.
Claim 40
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 6 wherein said compound is 8-(4-acetyl-1-piperazinyl)-9-fluoro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid.
Claim 41
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 6 wherein said compound is 8-(4-ethyl-1-piperazinyl)-9-fluoro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid.
Claim 42
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 19 wherein said compound is 8-chloro-9-(1-piperazinyl)-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid.
Claim 43
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 19 wherein said compound is 8-chloro-9-(4-methyl-1-piperazinyl)-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo-[3,2,1-ij]quinoline-5-carboxylic acid.
Claim 44
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 19 wherein said compound is 8-chloro-9-(4-formyl-1-piperazinyl)-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo-[3,2,1-ij]quinoline-5-carboxylic acid.
Claim 45
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 19 wherein said compound is 8-chloro-9-(4-acetyl-1-piperazinyl)-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo-[3,2,1-ij]quinoline-5-carboxylic acid.
Claim 46
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 19 wherein said compound is 8-fluoro-9-(1-piperazinyl)-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid.
Claim 47
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 19 wherein said compound is 8-fluoro-9-(4-formyl-1-piperazinyl)-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo-[3,2,1-ij]quinoline-5-carboxylic acid.
Claim 48
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 8 wherein said compound is 8-(4-trifluoroacetyl-1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 49
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 8 wherein said compound is 8-[4-(2,2,2-trifluoroethyl)-1-piperazinyl]-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 50
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 8 wherein said compound is 8-[4-(2-hydroxyethyl)-1-piperazinyl]-9-fluoro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 51
Dependent Claim
19 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 19 wherein said compound is 8-Fluoro-9-(4-methyl-1-piperazinyl)-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid.
Claim 52
Dependent Claim
20 words
A compound selected from the group consisting of 9-fluoro-6,7-dihydro-5-methyl-1-oxo-8-(1-piperazinyl)-1H,5H-benzo-[ij]quinolizine-2-carboxylic acid; 9-fluoro-6,7-dihydro-5-methyl-1-oxo-8-(4-methyl-1-piperazinyl)1H,5H-benzo[ij]quinolizine-2-carboxylic acid and the pharmaceutically acceptable acid addition salts thereof.
Claim 53
Dependent Claim
20 words
A compound selected from the group consisting of 9-fluoro-6,7-dihydro-5-methyl-1-oxo-8-(1-piperazinyl)-1H,5H-benzo-[ij]quinolizine-2-carboxylic acid; 9-fluoro-6,7-dihydro-5-methyl-1-oxo-8-(4-methyl-1-piperazinyl)1H,5H-benzo[ij]quinolizine-2-carboxylic acid and the pharmaceutically acceptable acid addition salts thereof.
Claim 54
Dependent Claim
45 words
A piperazinylbenzoheterocyclic compound or a pharmaceutically acceptable salt thereof as in claim 1, wherein R 3 represents hydrogen, lower alkyl, lower alkanoyl, lower alkylsulfonyl, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, benzoyl, p-toluenesulfonyl or a group represented by the formula ##STR32##
Claim 55
Dependent Claim
15 words
The piperazinylbenzoheterocyclic compound or pharmaceutically acceptable salt of claim 52, wherein R 3 represents hydrogen.
Claim 56
Dependent Claim
15 words
The piperazinylbenzoheterocyclic compound or pharmaceutically acceptable salt of claim 53, wherein R 4 represents hydrogen.
Claim 57
Dependent Claim
21 words
The piperazinylbenzoheterocyclic compound or pharmaceutically acceptable salt of claim 54, wherein R 1 represents alkyl having 1 to 4 carbon atoms.
Claim 58
Dependent Claim
15 words
The piperazinylbenzoheterocyclic compound or pharmaceutically acceptable salt of claim 54, wherein R 1 represents hydrogen.
Claim 59
Dependent Claim
15 words
The piperazinylbenzoheterocyclic compound or pharmaceutically acceptable salt of claim 53, wherein R 4 represents halogen.
Claim 60
Dependent Claim
21 words
The piperazinylbenzoheterocyclic compound or pharmaceutically acceptable salt of claim 57, wherein R 1 represents alkyl having 1 to 4 carbon atoms.
Claim 61
Dependent Claim
41 words
The piperazinylbenzoheterocyclic compound or pharmaceutically acceptable salt of claim 52, wherein R 3 represents lower alkyl, lower alkanoyl, lower alkylsulfonyl, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, benzoyl, p-toluenesulfonyl or a group represented by the formula ##STR33##
Claim 62
Dependent Claim
15 words
An antimicrobial composition comprising an antimicrobially effective amount of a piperazinylbenzoheterocyclic compound of claim 1.
Claim 63
Dependent Claim
11 words
An antimicrobial composition as in claim 60 wherein n is 1.
Claim 64
Dependent Claim
24 words
An antimicrobial composition as in claim 60 wherein n is 0, R 1 represents hydrogen or lower alkyl, and R 2 represents hydrogen atom.
Claim 65
Dependent Claim
27 words
An antimicrobial composition as in claim 60 wherein n is 0 and R 1 and R 2 together represent the atoms necessary to form a cyclohexane ring.
Claim 66
Dependent Claim
39 words
An antimicrobial composition as in claim 60, wherein R 3 represents hydrogen, lower alkyl, lower alkanoyl, lower alkylsulfonyl, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, benzoyl, p-toluenesulfonyl or a group represents by the formula ##STR34##
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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) | 1986-11-21 | 1987-05-23 | 1987-11-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-21 | 1991-05-23 | 1991-11-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-21 | 1995-05-23 | 1995-11-22 | $7700.00 | Window Closed / Lapsed |