US4260627A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1-, 6- And 2-substituted-1-carba-2-penem-3-carboxylic acids
Assignee: Merck and Co Inc
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Filing: 1978-10-24
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Granted: 1981-04-07
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Expires: 1998-10-24
Abstract
Abstract Disclosed are 1-, 6- and 2-substituted-1-carba-2-penem-3-carboxylic acids of the following structure: <IMAGE> wherein R1, R2, R3 and R4 are, 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
- 👤 Burton G. Christensen
- 👤 David H. Shih
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 06:15
CPC Classifications
C; C07; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; A; A61; A61P; A61P31/00; A61P31/04; C07C; C07C205/00; C07C205/39; C07C205/42; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/72; C07C45/74; C07D477/00; C07D477/10; C07D477/12; C07D477/14; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/568
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
142 words
A compound having the structure: ##STR184## and the pharmaceutically acceptable salts thereof; wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen (R 3 is not hydrogen), and substituted and unsubstituted: alkyl having 1-6 carbon atoms, alkenyl and alkynyl having 2-6 carbon atoms, aryl and aralkyl having 6-10 ring carbon atoms and 1-6 carbon atoms in the alkyl chain, cycloalkyl and cycloalkylalkyl having 3 to 6 ring carbon atoms and 1-6 carbon atoms in the alkyl moiety; wherein the substituents on R 1 , R 2 , R 3 and R 4 are selected from chloro, bromo, fluoro, hydroxyl, amino, mono-, di- and trialkyl substituted amino (each alkyl having 1-6 carbon atoms) alkoxyl having 1-6 carbon atoms, guanidino, cyano, amidino and carboxyl; with the proviso that R 4 is not hydrogen.
Claim 2
Dependent Claim
142 words
A compound having the structure: ##STR184## and the pharmaceutically acceptable salts thereof; wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen (R 3 is not hydrogen), and substituted and unsubstituted: alkyl having 1-6 carbon atoms, alkenyl and alkynyl having 2-6 carbon atoms, aryl and aralkyl having 6-10 ring carbon atoms and 1-6 carbon atoms in the alkyl chain, cycloalkyl and cycloalkylalkyl having 3 to 6 ring carbon atoms and 1-6 carbon atoms in the alkyl moiety; wherein the substituents on R 1 , R 2 , R 3 and R 4 are selected from chloro, bromo, fluoro, hydroxyl, amino, mono-, di- and trialkyl substituted amino (each alkyl having 1-6 carbon atoms) alkoxyl having 1-6 carbon atoms, guanidino, cyano, amidino and carboxyl; with the proviso that R 4 is not hydrogen.
Claim 3
Dependent Claim
40 words
A compound having the structure: ##STR185## and the pharmaceutically acceptable salts thereof; wherein R 3 and R 4 are alkyl, cyclopropyl, benzyl or phenyl; R 1 is hydrogen and R 2 is alkyl or phenylalkyl substituted by hydroxyl or amino.
Claim 4
Dependent Claim
40 words
A compound having the structure: ##STR185## and the pharmaceutically acceptable salts thereof; wherein R 3 and R 4 are alkyl, cyclopropyl, benzyl or phenyl; R 1 is hydrogen and R 2 is alkyl or phenylalkyl substituted by hydroxyl or amino.
Claim 5
Dependent Claim
27 words
A compound according to claim 2 wherein R 3 and R 4 are methyl, ethyl, isopropyl, t-butyl or phenyl and R 2 is 1-hydroxyethyl, methyl, or hydroxymethyl.
Claim 6
Dependent Claim
138 words
A compound having the structure: ##STR186## and the pharmaceutically acceptable salts thereof: wherein R 4 is selected from the group consisting of: ##STR187## and wherein R 1 , R 2 and R 3 are independently selected from the group consisting of hydrogen (R 3 is not hydrogen), and substituted and unsubstituted: alkyl having 1-6 carbon atoms, alkenyl and alkynyl having 2-6 carbon atoms, aryl and aralkyl having 6-10 ring carbon atoms and 1-6 carbon atoms in the alkyl chain, cycloalkyl and cycloalkylalkyl having 3-6 ring carbon atoms and 1-6 carbon atoms in the alkyl moiety; wherein the substituents on R 1 , R 2 , and R 3 are selected from chloro, bromo, fluoro, hydroxyl, amino, mono-, di- and trialkyl substituted amino (each alkyl having 1-6 carbon atoms) alkoxyl having 1-6 carbon atoms, guanidino, cyano, amidino, and carboxyl.
Claim 7
Dependent Claim
138 words
A compound having the structure: ##STR186## and the pharmaceutically acceptable salts thereof: wherein R 4 is selected from the group consisting of: ##STR187## and wherein R 1 , R 2 and R 3 are independently selected from the group consisting of hydrogen (R 3 is not hydrogen), and substituted and unsubstituted: alkyl having 1-6 carbon atoms, alkenyl and alkynyl having 2-6 carbon atoms, aryl and aralkyl having 6-10 ring carbon atoms and 1-6 carbon atoms in the alkyl chain, cycloalkyl and cycloalkylalkyl having 3-6 ring carbon atoms and 1-6 carbon atoms in the alkyl moiety; wherein the substituents on R 1 , R 2 , and R 3 are selected from chloro, bromo, fluoro, hydroxyl, amino, mono-, di- and trialkyl substituted amino (each alkyl having 1-6 carbon atoms) alkoxyl having 1-6 carbon atoms, guanidino, cyano, amidino, and carboxyl.
Claim 8
Dependent Claim
17 words
A compound according to claim 4 wherein R 3 is alkyl having 1-6 carbon atoms or phenyl.
Claim 9
Dependent Claim
26 words
An antibiotic pharmaceutical composition comprising a therapeutically effective amount of a compound according to claims 1, 2, 3, 4 or 5 and a pharmaceutical carrier therefor.
References Cited (Backward Citations)
US3950357A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-04-06 | 1984-10-06 | 1985-04-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-06 | 1988-10-06 | 1989-04-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-06 | 1992-10-06 | 1993-04-07 | $7700.00 | Window Closed / Lapsed |