US4269873A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-, 5-, and 6-Substituted-1-carbadethiapen-2-em-3-carboxylic acids
Assignee: Merck and Co Inc
•
Filing: 1979-07-25
•
Granted: 1981-05-26
•
Expires: 1999-07-25
Abstract
Abstract Disclosed are 2-, 5- and 6-substituted-1-carbadethiapen-2-em-3-carboxylic acids having the structure: <IMAGE> I wherein R6, R7, R8 and R9 are, inter alia, independently selected from the group consisting of hydrogen, (R9 is not 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 and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
Inventors
- 👤 Burton G. Christensen
- 👤 David B. R. Johnston
- 👤 Susan M. Schmitt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 09:58
CPC Classifications
C; C07; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07C; C07C205/00; C07C205/39; C07C205/42; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/10
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
126 words
A compound having the structure: ##STR270## and the pharmaceutically acceptable salts thereof; wherein R 6 is selected from the group consisting of hydrogen and loweralkyl; R 7 is selected from the group consisting of: hydroxyloweralkyl which may be substituted with cycloloweralkyl, phenyl, trifluoromethyl, dioxolane, carboxyl, methyltetrazole and aminomethylphenyl and aminoloweralkyl; R 8 is selected from the group consisting of hydrogen, loweralkyl which may be substituted with amino, formamidino, acetamidino, guanidino, loweralkanoyl, hydroxy, halo and morpholane, phenyl which may be substituted with aminomethyl, formamidinomethyl and acetamidinomethyl, methylthiadiazole, methyltetrazole, pyridine, aminomethylthiadiazole and aminomethyltetrazole; and R 9 is selected from the group consisting of loweralkyl, cycloloweralkyl, cycloloweralkylloweralkyl, phenyl, halophenyl, loweralkoxyphenyl and trifluoromethyl; and wherein R 7 is not 1-hydroxyethyl when R 6 is hydrogen and R 8 is 2-aminoethyl.
Claim 2
Dependent Claim
126 words
A compound having the structure: ##STR270## and the pharmaceutically acceptable salts thereof; wherein R 6 is selected from the group consisting of hydrogen and loweralkyl; R 7 is selected from the group consisting of: hydroxyloweralkyl which may be substituted with cycloloweralkyl, phenyl, trifluoromethyl, dioxolane, carboxyl, methyltetrazole and aminomethylphenyl and aminoloweralkyl; R 8 is selected from the group consisting of hydrogen, loweralkyl which may be substituted with amino, formamidino, acetamidino, guanidino, loweralkanoyl, hydroxy, halo and morpholane, phenyl which may be substituted with aminomethyl, formamidinomethyl and acetamidinomethyl, methylthiadiazole, methyltetrazole, pyridine, aminomethylthiadiazole and aminomethyltetrazole; and R 9 is selected from the group consisting of loweralkyl, cycloloweralkyl, cycloloweralkylloweralkyl, phenyl, halophenyl, loweralkoxyphenyl and trifluoromethyl; and wherein R 7 is not 1-hydroxyethyl when R 6 is hydrogen and R 8 is 2-aminoethyl.
Claim 3
Dependent Claim
72 words
A compound according to claim 1 wherein R 9 is selected from the group consisting of loweralkyl, cycloloweralkyl, cycloloweralkylloweralkyl, phenyl and loweralkoxyphenyl; R 8 is selected from the group consisting of aminoloweralkyl, formamidinoloweralkyl, acetamidinoloweralkyl and guanidinoloweralkyl; R 7 is selected from the group consisting of hydroxyloweralkyl which may be substituted with cycloloweralkyl, phenyl, carboxyl, trifluoromethyl, dioxalane, methyltetrazole and aminomethylphenyl; and R 6 is selected from the group consisting of hydrogen and methyl.
Claim 4
Dependent Claim
26 words
A compound according to claim 2 wherein R 9 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, cyclopropyl, cyclobutyl, cyclohexyl, cyclopropylmethyl and methoxyphenyl.
Claim 5
Dependent Claim
21 words
A compound according to claim 2 wherein R 8 is selected from the group consisting of aminoethyl, formamidinoethyl, acetamidinoethyl and guanidinoethyl.
Claim 6
Dependent Claim
13 words
A compound according to claim 1 selected from the group consisting of: ##STR271##
Claim 7
Dependent Claim
23 words
A compound according to claim 5 wherein the aminoethylthio side chain, ##STR272## is replaced by a member of the group consisting of: ##STR273##
Claim 8
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.
References Cited (Backward Citations)
US4181733A
Cited
US4153714A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-05-25 | 1984-11-24 | 1985-05-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-05-25 | 1988-11-24 | 1989-05-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-05-25 | 1992-11-24 | 1993-05-26 | $7700.00 | Window Closed / Lapsed |