US4543257A
Expired / Lapsed
US
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1-Carba-2-penem-3-carboxylic acid
Assignee: Merck and Co Inc
•
Filing: 1980-01-04
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Granted: 1985-09-24
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Expires: 2000-01-04
Abstract
Abstract Disclosed are 1-carba-2-penem-3-carboxylic acids of the following structure: <IMAGE> wherein R1, R2 and R3 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
- 👤 Lovji D. Cama
- 👤 Burton G. Christensen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 23:42
CPC Classifications
C; C07; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D477/00; C07D477/10; 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: 44
Claim 1
Independent Claim
156 words
A compound having the structural formula: ##STR590## and the pharmaceutically acceptable salts thereof wherein R 1 , R 2 and R 3 are independently selected from the group consisting of: hydrogen, mono-substituted and unsubstituted: alkyl having from 1 to 10 carbon atoms, alkenyl and akynyl having from 2 to 10 carbon atoms, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl and cycloalkenylalkyl wherein the preceding cycloalkyl or cycloalkenyl moieties comprise 3 to 6 carbon atoms and the alkyl or alkenyl moieties comprise 1 to 6 carbon atoms, phenyl, phenylalkyl, phenylalkenyl and phenylalkynyl having 1-6 carbon atoms in the chain; and wherein the substituent relative to the above-listed groups is selected from the group consisting of amino, hydroxyl, mercapto, alkylthio having from 1 to 6 carbon atoms, sulfamoyl, amidino, guanidino, nitro, chloro, bromo, fluoro, cyano, and carboxyl; with the proviso that when one of R 1 or R 2 is hydrogen and the other is 1-hydroxyethyl, then R 3 is not hydrogen.
Claim 2
Dependent Claim
156 words
A compound having the structural formula: ##STR590## and the pharmaceutically acceptable salts thereof wherein R 1 , R 2 and R 3 are independently selected from the group consisting of: hydrogen, mono-substituted and unsubstituted: alkyl having from 1 to 10 carbon atoms, alkenyl and akynyl having from 2 to 10 carbon atoms, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl and cycloalkenylalkyl wherein the preceding cycloalkyl or cycloalkenyl moieties comprise 3 to 6 carbon atoms and the alkyl or alkenyl moieties comprise 1 to 6 carbon atoms, phenyl, phenylalkyl, phenylalkenyl and phenylalkynyl having 1-6 carbon atoms in the chain; and wherein the substituent relative to the above-listed groups is selected from the group consisting of amino, hydroxyl, mercapto, alkylthio having from 1 to 6 carbon atoms, sulfamoyl, amidino, guanidino, nitro, chloro, bromo, fluoro, cyano, and carboxyl; with the proviso that when one of R 1 or R 2 is hydrogen and the other is 1-hydroxyethyl, then R 3 is not hydrogen.
Claim 3
Dependent Claim
112 words
A compound according to claim 1 wherein R 2 is hydrogen and R 1 and R 3 are independently selected from the group consisting of hydrogen (R 3 is not hydrogen), mono-substituted or unsubstituted: alkyl having from 1 to 6 carbon atoms, aralkyl wherein the aryl moiety is phenyl and the alkyl moiety contains 1 to 6 carbon atoms, aralkyl wherein the aryl moiety is phenyl and the alkyl moiety contains 1 to 6 carbon atoms, aralkenyl wherein the aryl moiety is phenyl and the alkenyl moiety contains 2 to 6 carbon atoms, and phenyl; wherein the substituent is selected from the group consisting of hydroxyl, amino, chloro, bromo, fluoro and carboxyl.
Claim 4
Dependent Claim
20 words
A compound according to claim 2 having the structure: ##STR591## wherein n is an integer selected from 1 to 4.
Claim 5
Dependent Claim
35 words
A compound having the structural formula: ##STR592## and the pharmaceutically acceptable salts thereof wherein R 2 is selected from the group consisting of: ##STR593## and R 3 is selected from the group consisting of: ##STR594##
Claim 6
Dependent Claim
35 words
A compound having the structural formula: ##STR592## and the pharmaceutically acceptable salts thereof wherein R 2 is selected from the group consisting of: ##STR593## and R 3 is selected from the group consisting of: ##STR594##
Claim 7
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR595##
Claim 8
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR596##
Claim 9
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR597##
Claim 10
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR598##
Claim 11
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR599##
Claim 12
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR600##
Claim 13
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR601##
Claim 14
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR602##
Claim 15
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR603##
Claim 16
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR604##
Claim 17
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR605##
Claim 18
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR606##
Claim 19
Dependent Claim
20 words
A compound according to claim 4 wherein R 2 is ##STR607## and R 3 is --C.tbd.C--CH 2 NH 2 .
Claim 20
Dependent Claim
18 words
A compound according to claim 4 wherein R 2 is --CH 2 OH and R 3 is ##STR608##
Claim 21
Dependent Claim
18 words
A compound according to claim 4 wherein R 2 is --CH 2 OH and R 3 is ##STR609##
Claim 22
Dependent Claim
18 words
A compound according to claim 4 wherein R 2 is --CH 2 OH and R 3 is ##STR610##
Claim 23
Dependent Claim
18 words
A compound according to claim 4 wherein R 2 is --CH 2 OH and R 3 is ##STR611##
Claim 24
Dependent Claim
18 words
A compound according to claim 4 wherein R 2 is --CH 2 OH and R 3 is ##STR612##
Claim 25
Dependent Claim
18 words
A compound according to claim 4 wherein R 2 is --CH 2 OH and R 3 is ##STR613##
Claim 26
Dependent Claim
22 words
A compound according to claim 4 wherein R 2 is --CH 2 OH and R 3 is --C.tbd.C--CH 2 NH 2 .
Claim 27
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR614##
Claim 28
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR615##
Claim 29
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR616##
Claim 30
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR617##
Claim 31
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR618##
Claim 32
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR619##
Claim 33
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR620##
Claim 34
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR621##
Claim 35
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR622##
Claim 36
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR623##
Claim 37
Dependent Claim
11 words
A compound according to claim 4 wherein R 2 is ##STR624##
Claim 38
Dependent Claim
18 words
A compound according to claim 4 wherein R 2 is CF 3 CH(OH)-- and R 3 is phenyl.
Claim 39
Dependent Claim
18 words
A compound according to claim 4 wherein R 2 is CF 3 CH(OH)-- and R 3 is ##STR625##
Claim 40
Dependent Claim
18 words
A compound according to claim 4 wherein R 2 is CF 3 CH(OH)-- and R 3 is ##STR626##
Claim 41
Dependent Claim
20 words
An antibiotic composition comprising a therapeutically effective amount of a compound according to claim 1 and a pharmaceutical carrier therefor.
Claim 42
Dependent Claim
24 words
An antibiotic composition comprising, in unitary dosage form, a therapeutically effective amount of a compound according to claim 1 and a pharmaceutical carrier therefor.
Claim 43
Dependent Claim
6 words
The compound which is benzyl 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate.
Claim 44
Dependent Claim
6 words
The compound which is benzyl 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-09-23 | 1989-03-25 | 1989-09-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-23 | 1993-03-25 | 1993-09-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-23 | 1997-03-25 | 1997-09-24 | $7700.00 | Window Closed / Lapsed |