US4218459A
Expired / Lapsed
US
⏱️ 0.0 years remaining
6-Amido-1-carba-2-penem-3-carboxylic acid
Assignee: Merck and Co Inc
•
Filing: 1977-12-28
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Granted: 1980-08-19
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Expires: 1997-12-28
Abstract
Abstract Disclosed are 6-amido-1-carba-2-penem-3-carboxylic acids of the following structure: <IMAGE> wherein R1 is hydrogen or acyl and R3 is, inter alia, independently selected from the group consisting of hydrogen, alkyl, aryl, and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
Inventors
- 👤 Lovji D. Cama
- 👤 Burton G. Christensen
- 👤 Ravindra N. Guthikonda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:25
CPC Classifications
C; C07; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/085; C07C; C07C205/00; C07C205/39; C07C205/42; C07D477/00; C07D477/10; C07D477/24; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/568
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
91 words
A compound having the following structural formula: ##STR69## wherein R is a pharmaceutically acceptable salt or benzyl, p-nitrobenzyl, o-nitrobenzyl, t-butyl, bromo-t-butyl, t-butyl-dimethylsilyl, trimethylsilyl, trichloroethyl; R 1 is phenylacetyl, D-phenylglycyl, (α-carboxy)-2-thienylacetyl, (α-carboxy)phenylacetyl, α-hydroxyphenylacetyl, or 3-isothiazoylacetyl; and R 3 is substituted and unsubstituted: loweralkyl having from 1 to 4 carbon atoms, lower alkenyl having 2-6 carbon atoms, or phenyl wherein the substituent is selected from the group consisting of hydroxyl, amino, amidino, guanidino, phenyl, aminoalkyl, hydroxyalkyl, mercapto, carboxyl, trifluoromethyl, loweralkylthio, and loweralkoxyl wherein the alkyl or alkoxyl has 1 to 6 carbon atoms.
Claim 2
Dependent Claim
91 words
A compound having the following structural formula: ##STR69## wherein R is a pharmaceutically acceptable salt or benzyl, p-nitrobenzyl, o-nitrobenzyl, t-butyl, bromo-t-butyl, t-butyl-dimethylsilyl, trimethylsilyl, trichloroethyl; R 1 is phenylacetyl, D-phenylglycyl, (α-carboxy)-2-thienylacetyl, (α-carboxy)phenylacetyl, α-hydroxyphenylacetyl, or 3-isothiazoylacetyl; and R 3 is substituted and unsubstituted: loweralkyl having from 1 to 4 carbon atoms, lower alkenyl having 2-6 carbon atoms, or phenyl wherein the substituent is selected from the group consisting of hydroxyl, amino, amidino, guanidino, phenyl, aminoalkyl, hydroxyalkyl, mercapto, carboxyl, trifluoromethyl, loweralkylthio, and loweralkoxyl wherein the alkyl or alkoxyl has 1 to 6 carbon atoms.
Claim 3
Dependent Claim
19 words
The compound of claim 1 wherein R 3 is H, C 6 H 5 , CH 3 , ##STR70##
Claim 4
Dependent Claim
16 words
A compound according to claim 2 wherein R 1 is ##STR71## and R 3 is H.
Claim 5
Dependent Claim
20 words
A compound according to claim 2 wherein R 2 is ##STR72## and R 3 is C 6 H 5 .
Claim 6
Dependent Claim
18 words
A compound according to claim 2 wherein R 1 is ##STR73## and R 3 is CH 3 .
Claim 7
Dependent Claim
8 words
A compound according to claim 2 wherein ##STR74##
Claim 8
Dependent Claim
8 words
A compound according to claim 2 wherein ##STR75##
Claim 9
Dependent Claim
8 words
A compound according to claim 2 wherein ##STR76##
Claim 10
Dependent Claim
8 words
A compound according to claim 2 wherein ##STR77##
Claim 11
Dependent Claim
8 words
A compound according to claim 2 wherein ##STR78##
Claim 12
Dependent Claim
8 words
A compound according to claim 2 wherein ##STR79##
Claim 13
Dependent Claim
8 words
A compound according to claim 2 wherein ##STR80##
Claim 14
Dependent Claim
8 words
A compound according to claim 2 wherein ##STR81##
Claim 15
Dependent Claim
8 words
A compound according to claim 2 wherein ##STR82##
Claim 16
Dependent Claim
25 words
A pharmaceutical antibiotic compositions comprising, in unitary dosage form, a therapeutically effective amount of a compound according to claim 2 and a pharmaceutical carrier therefor.
References Cited (Backward Citations)
US4011216A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-08-19 | 1984-02-18 | 1984-08-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-08-19 | 1988-02-18 | 1988-08-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-08-19 | 1992-02-18 | 1992-08-19 | $7700.00 | Window Closed / Lapsed |