Patent US5100720A successfully refreshed from Google Patents.
Patent US4309346A successfully refreshed from Google Patents.
US4309346A
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Process for the preparation of 1-carbapenems and intermediates via trithioorthoacetates
Assignee: Merck and Co Inc
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Filing: 1980-03-27
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Granted: 1982-01-05
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Expires: 2000-03-27
Abstract
Abstract Disclosed is a process for the total synthesis of 1-carbapenem antibiotics (I) from L-aspartic acid via intermediates II and III: <IMAGE> I <IMAGE> II <IMAGE> III wherein R is hydrogen, a pharmaceutically acceptable ester moiety or salt cation, or a readily removable blocking group; R6 and R7 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl; R1' is hydrogen or a protecting group; and Ra, Rb and Rc are independently selected from alkyl, aryl and aralkyl.
Inventors
- 👤 Burton G. Christensen
- 👤 Ronald W. Ratcliffe
- 👤 Thomas N. Salzmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 18:44
CPC Classifications
C; C07; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; A; A61; A61P; A61P31/00; A61P31/04; C07D477/00; C07D477/02; C07D477/04; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/10; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
242 words
A compound having the structural formula: ##STR281## wherein R 1' is hydrogen or a readily removable trialkylsilyl protecting group; R a , R b and R c are independently selected from the group consisting of alkyl having 1-6 carbon atoms, phenyl and phenylalkyl having 7-10 carbon atoms; and wherein R 6 and R 7 are independently selected from the group consisting of: hydrogen; mono 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 aliphatic portion has 1-6 carbon atoms; wherein the substituent or substituents relative to the above-named radicals are selected from the group consisting of: chloro, bromo, fluoro, R 1 , ##STR282## wherein, relative to the above listed substituents on R 6 , and R 7 , the group R 1 and R 2 are independently selected from: hydrogen, 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 aliphatic portion has 1-6 carbon atoms; R 6 and R 7 are not both hydrogen at the same time; when R 6 /R 7 is hydrogen, then R 7 /R 6 is not ##STR283##
Claim 2
Dependent Claim
242 words
A compound having the structural formula: ##STR281## wherein R 1' is hydrogen or a readily removable trialkylsilyl protecting group; R a , R b and R c are independently selected from the group consisting of alkyl having 1-6 carbon atoms, phenyl and phenylalkyl having 7-10 carbon atoms; and wherein R 6 and R 7 are independently selected from the group consisting of: hydrogen; mono 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 aliphatic portion has 1-6 carbon atoms; wherein the substituent or substituents relative to the above-named radicals are selected from the group consisting of: chloro, bromo, fluoro, R 1 , ##STR282## wherein, relative to the above listed substituents on R 6 , and R 7 , the group R 1 and R 2 are independently selected from: hydrogen, 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 aliphatic portion has 1-6 carbon atoms; R 6 and R 7 are not both hydrogen at the same time; when R 6 /R 7 is hydrogen, then R 7 /R 6 is not ##STR283##
Claim 3
Dependent Claim
17 words
A compound according to claim 1, wherein R a , R b and R c are methyl.
Claim 4
Dependent Claim
22 words
A compound according to claim 1 wherein R 7 is hydrogen and R 6 is selected from the group consisting of: ##STR284##
Claim 5
Dependent Claim
165 words
A compound according to claim 1 wherein R 6 and R 7 are independently selected from the group consisting of: hydrogen; monosubstituted and unsubstituted: alkyl, alkenyl and alkynyl having from 1-10 carbon atoms, cycloalkyl, cycloalkyalkyl 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 aliphatic portion has 1-6 carbon atoms; wherein the substituent or substituents relative to the above-named radicals are selected from the group consisting of: ##STR285## wherein, relative to the above listed substituents on R 6 , and R 7 , the groups R 1 and R 2 are independently selected from: hydrogen, 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 aliphatic portion has 1-6 carbon atoms.
Claim 6
Dependent Claim
13 words
A compound according to claim 1 wherein R 7 is hydrogen or methyl.
Claim 7
Dependent Claim
42 words
A compound according to claim 5 wherein R 6 is selected from the group consisting of: substituted and unsubstituted: alkyl, alkenyl and cycloalkylalkyl wherein the substituent or substituents are selected from hydroxyl, alkoxyl having from 1-6 carbon atoms, phenoxy, amino, and carboxy.
Claim 8
Dependent Claim
37 words
A compound according to claims 5 or 6 wherein R 6 is selected from the group consisting of alkyl, cycloalkylalkyl, alkyl substituted by one or more hydroxyl groups, or cycloalkylalkyl substituted by one or more hydroxyl groups.
Claim 9
Dependent Claim
11 words
A compound according to claim 5 wherein R 7 is hydrogen.
References Cited (Backward Citations)
US4122262A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-01-04 | 1985-07-06 | 1986-01-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-01-04 | 1989-07-06 | 1990-01-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-01-04 | 1993-07-06 | 1994-01-05 | $7700.00 | Window Closed / Lapsed |