US4372965A
Expired / Lapsed
US
⏱️ 0.0 years remaining
6-, 1- And 2-substituted-thio-1-carbadethiapen-2-em-3-carboxylic acid S-oxides
Assignee: Merck and Co Inc
•
Filing: 1981-01-08
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Granted: 1983-02-08
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Expires: 2001-01-08
Abstract
Abstract Disclosed are S-oxides of 6-, 1- and 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids having the structure: <IMAGE> wherein: n is 1 or 2; and R1, R6, R7 and R8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, 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
2026-11-09 12:00
CPC Classifications
C; C07; C07D; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
135 words
A compound having the structure: ##STR11## wherein: R 1 , R 6 , R 7 and R 8 are independently selected from the group consisting of hydrogen, (R 1 is not H) substituted and unsubstituted: alkyl, alkenyl, and alkynyl, having from 1-10 carbon atoms; cycloalkyl, cycloalkylalkyl, and alkylcycloalkyl, having 3-6 carbon atoms in the cycloalkyl ring and 1-6 carbon atoms in the alkyl moieties; phenyl; aralkyl, aralkenyl and aralkynyl wherein the aryl moiety is phenyl and the alkyl chain has 1-6 carbon atoms; wherein the substituents or substituents relative to the above-named radicals are selected from the group consisting of: amino, mono-, di-, and trialkylamino, hydroxyl, alkoxyl, sulfamoyl, amidino, guanidino, nitro, chloro, bromo, fluoro, cyano and carboxy; and wherein the alkyl moieties of the above-recited substituents have 1-6 carbon atoms; n is 1 or 2.
Claim 2
Dependent Claim
135 words
A compound having the structure: ##STR11## wherein: R 1 , R 6 , R 7 and R 8 are independently selected from the group consisting of hydrogen, (R 1 is not H) substituted and unsubstituted: alkyl, alkenyl, and alkynyl, having from 1-10 carbon atoms; cycloalkyl, cycloalkylalkyl, and alkylcycloalkyl, having 3-6 carbon atoms in the cycloalkyl ring and 1-6 carbon atoms in the alkyl moieties; phenyl; aralkyl, aralkenyl and aralkynyl wherein the aryl moiety is phenyl and the alkyl chain has 1-6 carbon atoms; wherein the substituents or substituents relative to the above-named radicals are selected from the group consisting of: amino, mono-, di-, and trialkylamino, hydroxyl, alkoxyl, sulfamoyl, amidino, guanidino, nitro, chloro, bromo, fluoro, cyano and carboxy; and wherein the alkyl moieties of the above-recited substituents have 1-6 carbon atoms; n is 1 or 2.
Claim 3
Dependent Claim
15 words
A compound according to claim 1 wherein R 1 is alkyl, phenyl, benzyl or cycloalkyl.
Claim 4
Dependent Claim
26 words
A compound according to claim 1 wherein R 6 is H or methyl and R 7 is alkyl, phenyl, aralkyl or hydroxyl-substituted alkyl, phenyl or aralkyl.
Claim 5
Dependent Claim
142 words
A compound having the structure: ##STR12## wherein: n is 1; R 6 is hydrogen or methyl and R 8 is selected from the group consisting of: ##STR13## R 7 is selected from: ##STR14## and R 1 is independently selected from the group consisting of substituted and unsubstituted: alkyl, alkenyl, and alkynyl, having from 1-10 carbon atoms; cycloalkyl, cycloalkylalkyl, and alkylcycloalkyl, having 3-6 carbon atoms in the cycloalkyl ring and 1-6 carbon atoms in the alkyl moieties; phenyl; aralkyl, aralkenyl, and aralkynyl wherein the aryl moiety is phenyl and the alkyl chain has 1-6 carbon atoms; wherein the substituent or substituents relative to the above-named radicals are selected from the group consisting of: amino, mono-, di-, and trialkylamino, hydroxyl, alkoxyl, sulfamoyl, amidino, guanidino, nitro, chloro, bromo, fluoro, cyano and carboxy; and wherein the alkyl moieties of the above-recited substituents have 1-6 carbon atoms.
Claim 6
Dependent Claim
142 words
A compound having the structure: ##STR12## wherein: n is 1; R 6 is hydrogen or methyl and R 8 is selected from the group consisting of: ##STR13## R 7 is selected from: ##STR14## and R 1 is independently selected from the group consisting of substituted and unsubstituted: alkyl, alkenyl, and alkynyl, having from 1-10 carbon atoms; cycloalkyl, cycloalkylalkyl, and alkylcycloalkyl, having 3-6 carbon atoms in the cycloalkyl ring and 1-6 carbon atoms in the alkyl moieties; phenyl; aralkyl, aralkenyl, and aralkynyl wherein the aryl moiety is phenyl and the alkyl chain has 1-6 carbon atoms; wherein the substituent or substituents relative to the above-named radicals are selected from the group consisting of: amino, mono-, di-, and trialkylamino, hydroxyl, alkoxyl, sulfamoyl, amidino, guanidino, nitro, chloro, bromo, fluoro, cyano and carboxy; and wherein the alkyl moieties of the above-recited substituents have 1-6 carbon atoms.
Claim 7
Dependent Claim
18 words
A compound according to claim 4 wherein R 1 is methyl, ethyl, isopropyl, phenyl, benzyl, cyclopropyl, or cyclopropylmethyl.
Claim 8
Dependent Claim
139 words
A compound according to claim 1 wherein R 6 , R 7 and R 8 are independently selected from the group consisting of hydrogen, substituted and unsubstituted: alkyl, alkenyl, and alkynyl, having from 1-10 carbon cycloalkyl, cycloalkylalkyl, and alkylcycloalkyl, having 3-6 carbon atoms in the cycloalkyl ring and 1-6 carbon atoms in the alkyl moieties; phenyl; aralkyl, aralkenyl, and aralkynyl wherein the aryl moiety is phenyl and the alkyl chain has 1-6 carbon atoms; wherein the substituent or substituents relative to the above-named radicals are selected from the group consisting of: amino, mono-, di- and trialkylamino, hydroxyl, alkoxyl, sulfamoyl, amidino, guanidino, nitro, chloro, bromo, fluoro, cyano and carboxy; and wherein the alkyl moieties of the above-recited substituents have 1-6 carbon atoms; and R 1 is selected from the group consisting of methyl, ethyl, propyl, isopropyl cyclopropyl, phenyl and benzyl.
Claim 9
Dependent Claim
21 words
An antibiotic pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1 and a pharmaceutical carrier therefor.
Claim 10
Dependent Claim
17 words
A method of treatment comprising administering an antibacterial effective amount of a compound according to claim 1.
References Cited (Backward Citations)
US4181733A
Cited
US4123547A
Cited
US4150145A
Cited
US4218462A
Cited
US4232036A
Cited
US4341791A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-02-07 | 1986-08-09 | 1987-02-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-02-07 | 1990-08-09 | 1991-02-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-02-07 | 1994-08-09 | 1995-02-08 | $7700.00 | Window Closed / Lapsed |