US4150145A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-alkylated derivatives of thienamycin sulfoxide and sulfone
Assignee: Merck and Co Inc
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Filing: 1977-09-15
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Granted: 1979-04-17
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Expires: 1997-09-15
Abstract
Abstract Disclosed are N-alkylated derivatives of thienamycin sulfoxide (I, n=1) and sulfone (I, n=2): <IMAGE> I wherein n=1 or 2; and R5, R6, and R7 are, inter alia, hydrogen or alkyl. Such compounds the their pharmaceutically acceptable O- and carboxyl- 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
2026-11-03 12:11
CPC Classifications
C; C07; C07D; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
111 words
A compound selected from the group consisting of thienamycin sulfoxides and sulfones having the formulae: ##STR108## wherein: n=1 or 2; A is selected from the group consisting of halo, phosphate and sulfate; R 4 is selected from the group consisting of: hydrogen, sulfo, phosphono, carbamoyl, methylsulfonyl, sulfamoyl, dimethylsulfamoyl, N-methylcarbamoyl, bromoacetyl, hydroxyacetyl, aminoacetyl, dimethylaminoacetyl, trimethylammoniumacetyl, amidinoacetyl, guanidinoacetyl, methoxyacetyl, guanylacetyl, guanylthioacetyl, phosphamoyl, phosphonothioyl, thiocarbamoyl, methoxymethyl, hydroxyethyl, methoxyethyl, dimethylaminomethyl, dimethylaminoethyl, methylthiomethyl, amidinomethyl, and guanidinoethyl; R is hydrogen, ##STR109## 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), ##STR110##
Claim 2
Dependent Claim
111 words
A compound selected from the group consisting of thienamycin sulfoxides and sulfones having the formulae: ##STR108## wherein: n=1 or 2; A is selected from the group consisting of halo, phosphate and sulfate; R 4 is selected from the group consisting of: hydrogen, sulfo, phosphono, carbamoyl, methylsulfonyl, sulfamoyl, dimethylsulfamoyl, N-methylcarbamoyl, bromoacetyl, hydroxyacetyl, aminoacetyl, dimethylaminoacetyl, trimethylammoniumacetyl, amidinoacetyl, guanidinoacetyl, methoxyacetyl, guanylacetyl, guanylthioacetyl, phosphamoyl, phosphonothioyl, thiocarbamoyl, methoxymethyl, hydroxyethyl, methoxyethyl, dimethylaminomethyl, dimethylaminoethyl, methylthiomethyl, amidinomethyl, and guanidinoethyl; R is hydrogen, ##STR109## 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), ##STR110##
Claim 3
Dependent Claim
24 words
A compound according to claim 1 wherein R 5 , R 6 and R 7 are hydrogen or lower alkyl having 1-6 carbon atoms.
Claim 4
Dependent Claim
10 words
A compound according to claim 2 having the structure: ##STR111##
Claim 5
Dependent Claim
10 words
A compound according to claim 2 having the structure: ##STR112##
Claim 6
Dependent Claim
10 words
A compound according to claim 2 having the structure: ##STR113##
Claim 7
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.
Claim 8
Dependent Claim
27 words
An antibiotic pharmaceutical composition consisting essentially of, in unitary dosage form, a therapeutically effective amount of a compound according to claim 1 and a pharmaceutical carrier therefor.
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) | 1982-04-16 | 1982-10-16 | 1983-04-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-04-16 | 1986-10-16 | 1987-04-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-04-16 | 1990-10-16 | 1991-04-17 | $7700.00 | Window Closed / Lapsed |