US4235920A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-Alkylated derivatives of thienamycin
Assignee: Merck and Co Inc
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Filing: 1977-12-16
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Granted: 1980-11-25
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Expires: 1997-12-16
Abstract
Abstract Disclosed are N-alkylated derivatives of the antibiotic thienamycin, which has the following structure: <IMAGE> Such compounds and their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such derivatives, pharmaceutical compositions comprising such derivatives, and methods of treatment comprising administering such derivatives and compositions when an antibiotic effect is indicated.
Inventors
- 👤 Burton G. Christensen
- 👤 Raymond A. Firestone
- 👤 William J. Leanza
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 20:03
CPC Classifications
C; C07; C07D; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20; C07D205/00; C07D205/02; C07D205/06; C07D205/08
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
165 words
A compound having the structural formulae: ##STR101## wherein R 4 is a member selected from the group consisting of hydrogen, loweralkyl, sulfo, loweralkoxyloweralkyl, loweralkoxycarbonyl, loweralkanoyl and aminoloweralkanoyl; R 5 , R 6 , and R 7 are independently selected from the group consisting of hydrogen (not all of R 5 , R 6 and R 7 are hydrogen at the same time), CH 3 , CH 2 CH 3 , CH 2 CH═CH 2 , CH 2 CH 2 CH 3 , CH 2 (C 6 H 5 ), CH(C 6 H 5 ), C(C 6 H 5 ) 3 , ##STR102## X of the group, --COXR is O or S; R is selected from the group consisting of hydrogen, methyl, t-butyl, phenacyl, p-bromophenacyl; pivaloyloxymethyl, 2,2,2-trichloroethyl, allyl, 3-methyl-2-butenyl, 2-methyl-2-propenyl, benzyl, benzylhydryl, p-t-butylbenzyl, phthalidyl, phenyl, 5-indanyl, acetylthiomethyl, acetoxymethyl, propionyloxymethyl, methallyl, 3-butenyl, 4-pentenyl, 2-butenylacetoxyacetylmethyl, pivaloylacetylmethyl, diethylamino, dimethylaminoethyl, methoxymethyl, p-acetoxybenzyl, p-pivaloylbenzyl, p-isopropoxybenzyl, 5-indanylmethyl, benzyloxymethyl, methylthioethyl, dimethylaminoacetoxymethyl, crotonolacton-3-yl, acetamidomethyl, acetylthioethyl, pivaloylthiomethyl, methylthiomethyl; and A is a pharmaceutically acceptable anion.
Claim 2
Dependent Claim
165 words
A compound having the structural formulae: ##STR101## wherein R 4 is a member selected from the group consisting of hydrogen, loweralkyl, sulfo, loweralkoxyloweralkyl, loweralkoxycarbonyl, loweralkanoyl and aminoloweralkanoyl; R 5 , R 6 , and R 7 are independently selected from the group consisting of hydrogen (not all of R 5 , R 6 and R 7 are hydrogen at the same time), CH 3 , CH 2 CH 3 , CH 2 CH═CH 2 , CH 2 CH 2 CH 3 , CH 2 (C 6 H 5 ), CH(C 6 H 5 ), C(C 6 H 5 ) 3 , ##STR102## X of the group, --COXR is O or S; R is selected from the group consisting of hydrogen, methyl, t-butyl, phenacyl, p-bromophenacyl; pivaloyloxymethyl, 2,2,2-trichloroethyl, allyl, 3-methyl-2-butenyl, 2-methyl-2-propenyl, benzyl, benzylhydryl, p-t-butylbenzyl, phthalidyl, phenyl, 5-indanyl, acetylthiomethyl, acetoxymethyl, propionyloxymethyl, methallyl, 3-butenyl, 4-pentenyl, 2-butenylacetoxyacetylmethyl, pivaloylacetylmethyl, diethylamino, dimethylaminoethyl, methoxymethyl, p-acetoxybenzyl, p-pivaloylbenzyl, p-isopropoxybenzyl, 5-indanylmethyl, benzyloxymethyl, methylthioethyl, dimethylaminoacetoxymethyl, crotonolacton-3-yl, acetamidomethyl, acetylthioethyl, pivaloylthiomethyl, methylthiomethyl; and A is a pharmaceutically acceptable anion.
Claim 3
Dependent Claim
24 words
A compound according to claim 1 wherein R 4 is hydrogen, X is oxygen, and R is hydrogen, and the pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
23 words
A compound according to claim 2 wherein R 5 , R 6 and R 7 are hydrogen or loweralkyl having 1-6 carbon atoms.
Claim 5
Dependent Claim
10 words
The compound according to claim 3 having the structure: ##STR103##
Claim 6
Dependent Claim
10 words
The compound according to claim 3 having the structure: ##STR104##
Claim 7
Dependent Claim
17 words
A compound according to claim 3 having the structure: ##STR105## wherein A is a pharmaceutically acceptable anion.
Claim 8
Dependent Claim
10 words
The compound according to claim 6 wherein A is chloro.
Claim 9
Dependent Claim
23 words
An antibiotic pharmaceutical composition consisting essentially of a therapeutically effective amount of a compound according to claim 1 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) | 1983-11-25 | 1984-05-26 | 1984-11-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-25 | 1988-05-26 | 1988-11-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-25 | 1992-05-26 | 1992-11-25 | $7700.00 | Window Closed / Lapsed |