Patent US4576743A successfully refreshed from Google Patents.
Patent US4536335A successfully refreshed from Google Patents.
US4536335A
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Carbapenem antibiotics
Assignee: Bristol Myers Co
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Filing: 1983-06-07
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Granted: 1985-08-20
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Expires: 2003-06-07
Abstract
Abstract Disclosed are novel carbapenem derivatives characterized by a 2-substituent of the formula ##STR1## in which A represents cyclopentylene, cyclohexylene or C 2 -C 6 alkylene optionally substituted by one or more C 1 -C 4 alkyl groups; R 5 represents either (a) an optionally substituted aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, aryl, araliphatic, heteroaryl, heteroaraliphatic, heterocyclyl or heterocyclyl-aliphatic radical or (b) a divalent phenylene or C 1 -C 4 alkylene group joined to the ##STR2## ring so as to form a bridged polycyclic group; and ##STR3## represents a quaternized nitrogen-containing non-aromatic heterocycle. Such derivatives are useful as potent antibacterial agents.
Inventors
- 👤 Choung U. Kim
- 👤 Peter F. Micso, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 15:04
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088; C07D487/00; C07D487/02; C07D487/04; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
106 words
A compound of the formula ##STR135## wherein R 8 is hydrogen and R 1 is hydrogen, ##STR136## or R 1 and R 8 taken together represent ##STR137## A is cyclopentylene, cyclohexylene or C 2 -C 6 alkylene optionally substituted by one or more C 1 -C 4 alkyl groups; and ##STR138## wherein Y is hydrogen, C 1 -C 6 alkyl, hydroxy, --SC 1 -C 6 alkyl, carboxyl, carbamoyl, chloro, bromo, iodo, fluoro or phenyl; or a pharmaceutically acceptable salt thereof or a benzhydryl, allyl, p-nitrobenzyl, 2-naphthylmethyl, benzyl, trichloroethyl, silyl, phenacyl, p-methoxybenzyl, acetonyl, o-nitrobenzyl, 4-pyridylmethyl, C 1 -C 6 alkyl, pivaloyloxymethyl, acetoxymethyl, phthalidyl, indanyl or methoxymethyl ester.
Claim 2
Dependent Claim
106 words
A compound of the formula ##STR135## wherein R 8 is hydrogen and R 1 is hydrogen, ##STR136## or R 1 and R 8 taken together represent ##STR137## A is cyclopentylene, cyclohexylene or C 2 -C 6 alkylene optionally substituted by one or more C 1 -C 4 alkyl groups; and ##STR138## wherein Y is hydrogen, C 1 -C 6 alkyl, hydroxy, --SC 1 -C 6 alkyl, carboxyl, carbamoyl, chloro, bromo, iodo, fluoro or phenyl; or a pharmaceutically acceptable salt thereof or a benzhydryl, allyl, p-nitrobenzyl, 2-naphthylmethyl, benzyl, trichloroethyl, silyl, phenacyl, p-methoxybenzyl, acetonyl, o-nitrobenzyl, 4-pyridylmethyl, C 1 -C 6 alkyl, pivaloyloxymethyl, acetoxymethyl, phthalidyl, indanyl or methoxymethyl ester.
Claim 3
Dependent Claim
11 words
A compound according to claim 1 wherein R 1 is ##STR139##
Claim 4
Dependent Claim
19 words
A compound according to claim 1 wherein R 1 is ##STR140## and the absolute configuration is 5R, 6S, 8R.
Claim 5
Dependent Claim
13 words
A compound according to claim 1, 2 or 3 wherein A is ##STR141##
Claim 6
Dependent Claim
105 words
A compound of the formula ##STR142## wherein R 8 is hydrogen and R 1 is hydrogen, ##STR143## or R 1 and R 8 taken together represent ##STR144## A is cyclopentylene, cyclohexylene or C 2 -C 6 alkylene optionally substituted by one or more C 1 -C alkyl groups; and ##STR145## wherein Y is hydrogen, C 1 -C 6 alkyl, hydroxy, -SC 1 -C 6 alkyl, carboxyl, carbamoyl, chloro, bromo, iodo, fluoro or phenyl; or a pharmaceutically acceptable salt thereof or a benzhydryl, allyl, p-nitrobenzyl, 2-naphthylmethyl, benzyl, trichloroethyl, silyl, phenacyl, p-methoxybenzyl, acetonyl, o-nitrobenzyl, 4-pyridylmethyl, C 1 -C 6 alkyl, pivaloyloxymethyl, acetoxymethyl, phthalidyl, indanyl or methoxymethyl ester.
Claim 7
Dependent Claim
105 words
A compound of the formula ##STR142## wherein R 8 is hydrogen and R 1 is hydrogen, ##STR143## or R 1 and R 8 taken together represent ##STR144## A is cyclopentylene, cyclohexylene or C 2 -C 6 alkylene optionally substituted by one or more C 1 -C alkyl groups; and ##STR145## wherein Y is hydrogen, C 1 -C 6 alkyl, hydroxy, -SC 1 -C 6 alkyl, carboxyl, carbamoyl, chloro, bromo, iodo, fluoro or phenyl; or a pharmaceutically acceptable salt thereof or a benzhydryl, allyl, p-nitrobenzyl, 2-naphthylmethyl, benzyl, trichloroethyl, silyl, phenacyl, p-methoxybenzyl, acetonyl, o-nitrobenzyl, 4-pyridylmethyl, C 1 -C 6 alkyl, pivaloyloxymethyl, acetoxymethyl, phthalidyl, indanyl or methoxymethyl ester.
Claim 8
Dependent Claim
11 words
A compound according to claim 5 wherein R 1 is ##STR146##
Claim 9
Dependent Claim
19 words
A compound according to claim 5 wherein R 1 is ##STR147## and the absolute configuration is 5R, 6S, 8R.
Claim 10
Dependent Claim
25 words
A compound according to claim 5, 6, or 7 wherein A is --CH 2 CH 2 --, --CH 2 CH 2 CH 2 --, ##STR148##
Claim 11
Dependent Claim
81 words
A compound of the formula ##STR149## wherein R 8 is hydrogen and R 1 is hydrogen, ##STR150## or R 1 and R 8 taken together represent ##STR151## A is cyclopentylene, cyclohexylene or C 2 -C 6 alkylene optionally substituted by one or more C 1 -C 4 alkyl groups; and ##STR152## pharmaceutically acceptable salt thereof or a benzhydryl allyl, p-nitrobenzyl, 2-naphthylmethyl, benzyl, trichloroethyl, silyl, phenacyl, p-methoxybenzyl, acetonyl, o-nitrobenzyl, 4-pyridylmethyl, C 1 -C 6 alkyl, pivaloyloxymethyl, acetoxymethyl, phthalidyl, indanyl or methoxymethyl ester.
Claim 12
Dependent Claim
81 words
A compound of the formula ##STR149## wherein R 8 is hydrogen and R 1 is hydrogen, ##STR150## or R 1 and R 8 taken together represent ##STR151## A is cyclopentylene, cyclohexylene or C 2 -C 6 alkylene optionally substituted by one or more C 1 -C 4 alkyl groups; and ##STR152## pharmaceutically acceptable salt thereof or a benzhydryl allyl, p-nitrobenzyl, 2-naphthylmethyl, benzyl, trichloroethyl, silyl, phenacyl, p-methoxybenzyl, acetonyl, o-nitrobenzyl, 4-pyridylmethyl, C 1 -C 6 alkyl, pivaloyloxymethyl, acetoxymethyl, phthalidyl, indanyl or methoxymethyl ester.
Claim 13
Dependent Claim
11 words
A compound according to claim 9 wherein R 1 is ##STR153##
Claim 14
Dependent Claim
19 words
A compound according to claim 9 wherein R 1 is ##STR154## and the absolute configuration is 5R, 6S, 8R.
Claim 15
Dependent Claim
25 words
A compound according to claim 9, 10, and 11 wherein A is --CH 2 CH 2 --, --CH 2 CH 2 CH 2 --, ##STR155##
Claim 16
Dependent Claim
38 words
A compound of the formula ##STR156## or a pharmaceutically acceptable salt thereof or a benzhydryl, allyl, p-nitrobenzyl, 2-naphthylmethyl, benzyl, trichloroethyl, silyl, phenacyl, p-methoxybenzyl, acetonyl, o-nitrobenzyl, 4-pyridylmethyl, C 1 -C 6 alkyl, pivaloyloxymethyl, acetoxymethyl, phthalidyl, indanyl or methoxymethyl ester.
Claim 17
Dependent Claim
38 words
A compound of the formula ##STR156## or a pharmaceutically acceptable salt thereof or a benzhydryl, allyl, p-nitrobenzyl, 2-naphthylmethyl, benzyl, trichloroethyl, silyl, phenacyl, p-methoxybenzyl, acetonyl, o-nitrobenzyl, 4-pyridylmethyl, C 1 -C 6 alkyl, pivaloyloxymethyl, acetoxymethyl, phthalidyl, indanyl or methoxymethyl ester.
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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) | 1988-08-19 | 1989-02-18 | 1989-08-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-19 | 1993-02-18 | 1993-08-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-19 | 1997-02-18 | 1997-08-20 | $7700.00 | Window Closed / Lapsed |