US4262009A
Expired / Lapsed
US
⏱️ 0.0 years remaining
6- And 1,1-disubstituted-1-carbadethiapen-2-em-3-carboxylic acid
Assignee: Merck and Co Inc
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Filing: 1979-12-03
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Granted: 1981-04-14
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Expires: 1999-12-03
Abstract
Abstract Disclosed are 6- and 1-substituted-1-carbadethiapen-2-em-3-carboxylic acids I of the following structure: <IMAGE> I wherein R1, R2, R3 and R4 are, inter alia, independently selected from the group consisting of 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 03:58
CPC Classifications
C; C07; C07D; C07D477/00; C07D477/10; C07D477/12; C07D477/14; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/10; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/568
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
144 words
A compound having the structure: ##STR69## 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, and substituted and unsubstituted: alkyl having 1-6 carbon atoms; phenyl; phenylalkyl wherein the alkyl moiety has 1-6 carbon atoms; cycloalkyl and cycloalkylalkyl having 3 to 6 ring carbon atoms and 1-6 carbon atoms in the alkyl moiety; and spirocycloalkyl having 3 to 6 carbon atoms; wherein the substituent or substituents on R 1 , R 2 , R 3 and R 4 are selected from chloro, bromo, fluoro, hydroxyl, amino, mono-, di-, and trialkylamino (each alkyl having 1-6 carbon atoms), alkoxyl having 1-6 carbon atoms, cyano and carboxyl; wherein R 1 and R 2 are not hydrogen and R 3 and R 4 are not both hydrogen at the same time.
Claim 2
Dependent Claim
144 words
A compound having the structure: ##STR69## 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, and substituted and unsubstituted: alkyl having 1-6 carbon atoms; phenyl; phenylalkyl wherein the alkyl moiety has 1-6 carbon atoms; cycloalkyl and cycloalkylalkyl having 3 to 6 ring carbon atoms and 1-6 carbon atoms in the alkyl moiety; and spirocycloalkyl having 3 to 6 carbon atoms; wherein the substituent or substituents on R 1 , R 2 , R 3 and R 4 are selected from chloro, bromo, fluoro, hydroxyl, amino, mono-, di-, and trialkylamino (each alkyl having 1-6 carbon atoms), alkoxyl having 1-6 carbon atoms, cyano and carboxyl; wherein R 1 and R 2 are not hydrogen and R 3 and R 4 are not both hydrogen at the same time.
Claim 3
Dependent Claim
47 words
A compound according to claim 1 wherein R 1 and R 2 are selected from: alkyl, cyclopropyl, spirocyclopropyl, and benzyl and phenyl; R 4 is alkyl and phenylalkyl substituted by hydroxyl or amino; and R 3 is hydrogen or alkyl or phenylalkyl substituted by hydroxyl or amino.
Claim 4
Dependent Claim
34 words
A compound according to claim 2 wherein R 1 and R 2 are selected from: methyl, ethyl, isopropyl, t-butyl, spirocyclopropyl, or phenyl; R 4 is 1-hydroxyethyl, methyl, or hydroxymethyl; and R 3 is hydrogen.
Claim 5
Dependent Claim
10 words
A compound according to claim 1 having the structure: ##STR70##
Claim 6
Dependent Claim
10 words
A compound according to claim 1 having the structure: ##STR71##
Claim 7
Dependent Claim
26 words
An antibiotic pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1, 2, 3, 4 or 5 and a pharmaceutical carrier therefor.
Claim 8
Independent Claim
22 words
A method of treatment comprising administering an antibiotically effective amount of a compound according to claims 1, 2, 3, 4 or 5.
References Cited (Backward Citations)
US4181733A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-04-13 | 1984-10-13 | 1985-04-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-13 | 1988-10-13 | 1989-04-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-13 | 1992-10-13 | 1993-04-14 | $7700.00 | Window Closed / Lapsed |