US4269772A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Synthesis of thienamycin via trans-3-carboxymethylene-4-carboxy-5-methyl-Δ2 -isoxazoline
Assignee: Merck and Co Inc
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Filing: 1980-01-14
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Granted: 1981-05-26
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Expires: 2000-01-14
Abstract
Abstract Disclosed is a process for the stereocontrolled total synthesis of thienamycin, which synthesis proceeds via intermediate II: <IMAGE> II wherein R5 and R6 are removable protecting groups.
Inventors
- 👤 David G. Melillo
- 👤 Kenneth M. Ryan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 05:35
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/16; C07D309/28; C07D309/30; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D261/00; C07D261/02; C07D261/04; C07D477/00; C07D477/02; C07D477/04; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/10; C07F7/18; C07F7/1804; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 2
Claim 1
Independent Claim
114 words
A process for preparing: ##STR22## and its pharmaceutically acceptable salts which comprise the cycloaddition of: ##STR23## with CH.sub.3 CH═CHCOOR.sup.6 to form: ##STR24## followed by reduction to yield: ##STR25## followed by cyclization and deblocking to yield: ##STR26## followed by alcoholysis with R 1 OH to form: ##STR27## followed by cyclizing to form: ##STR28## followed by carboxyl-deprotecting, activating and treating with (R 3 O 2 CCH 2 CO 2 ) 2 Mg to form: ##STR29## followed by deprotecting, diazotizing, and cyclizing to form: ##STR30## followed by activating, treating with HSCH 2 CH 2 NHR 4 and deprotecting wherein R 1 , R 3 , R 4 , R 5 and R 6 are removable protecting groups.
Claim 2
Dependent Claim
114 words
A process for preparing: ##STR22## and its pharmaceutically acceptable salts which comprise the cycloaddition of: ##STR23## with CH.sub.3 CH═CHCOOR.sup.6 to form: ##STR24## followed by reduction to yield: ##STR25## followed by cyclization and deblocking to yield: ##STR26## followed by alcoholysis with R 1 OH to form: ##STR27## followed by cyclizing to form: ##STR28## followed by carboxyl-deprotecting, activating and treating with (R 3 O 2 CCH 2 CO 2 ) 2 Mg to form: ##STR29## followed by deprotecting, diazotizing, and cyclizing to form: ##STR30## followed by activating, treating with HSCH 2 CH 2 NHR 4 and deprotecting wherein R 1 , R 3 , R 4 , R 5 and R 6 are removable protecting groups.
References Cited (Backward Citations)
No citation records indexed.
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 |