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US4391752A
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Process for preparing 5H-pyrrolo[2,1-c]-[1,4]thiazepine-1,5-diones
Assignee: John Wyeth and Brother Ltd
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Filing: 1982-05-10
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Granted: 1983-07-05
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Expires: 2002-05-10
Abstract
Abstract The invention relates to the preparation of 1-bromo-2-D-alkylpropanoyl-L-proline derivatives and analogous compounds which are useful as chemical intermediates to angiotensin converting enzyme (ACE) inhibitors and to the stereospecific synthesis of such ACE inhibitors having the formula: ##STR1## wherein R 1 is lower alkyl and R 4 and R 5 are both hydrogen or together with the carbons to which they are attached represent a benzene ring optionally substituted by defined substituents. Intermediates of formula ##STR2## are also disclosed wherein R 1 , R 4 , R 5 are as defined above and B 30 is a cation.
Inventors
- 👤 Roger Crossley
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 08:30
CPC Classifications
C; C07; C07D; C07D513/00; C07D513/02; C07D513/04; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/16
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
169 words
A process for preparing a compound of formula XI ##STR21## wherein R 1 is lower alkyl, R 4 and R 5 either both represent hydrogen or together with the carbon atoms to which they are attached represent a fused benzene ring optionally substituted by a group selected from hydroxy, lower alkyl, lower alkoxy and halogen, which comprises selecting a process from the group consisting of (a) reacting a compound of formula ##STR22## substantially free from the L,L isomer, wherein R 1 , R 4 and R 5 are as defined above with a haloformate ester and a sulphide of formula XII Y--SH (XII) wherein Y represents hydrogen or an alkali metal, with the proviso that when Y is hydrogen the reaction is carried out in the presence of base, and cyclising the product by heating, and (b) cyclising by heating a compound of formula (XIII) ##STR23## substantially free of L,L stereoisomer wherein R 1 , R 4 and R 5 are as defined above and B.sup.⊕ is a cation.
Claim 2
Dependent Claim
169 words
A process for preparing a compound of formula XI ##STR21## wherein R 1 is lower alkyl, R 4 and R 5 either both represent hydrogen or together with the carbon atoms to which they are attached represent a fused benzene ring optionally substituted by a group selected from hydroxy, lower alkyl, lower alkoxy and halogen, which comprises selecting a process from the group consisting of (a) reacting a compound of formula ##STR22## substantially free from the L,L isomer, wherein R 1 , R 4 and R 5 are as defined above with a haloformate ester and a sulphide of formula XII Y--SH (XII) wherein Y represents hydrogen or an alkali metal, with the proviso that when Y is hydrogen the reaction is carried out in the presence of base, and cyclising the product by heating, and (b) cyclising by heating a compound of formula (XIII) ##STR23## substantially free of L,L stereoisomer wherein R 1 , R 4 and R 5 are as defined above and B.sup.⊕ is a cation.
Claim 3
Dependent Claim
19 words
A process as claimed in claim 1 wherein Y is hydrogen which is carried out in tertiary amine solvent.
Claim 4
Dependent Claim
13 words
A process as claimed in claim 1 wherein B.sup.⊕ is an alkylammonium cation.
Claim 5
Dependent Claim
23 words
A process as claimed in claim 1 in which the compound of formula VII is prepared by a process according to claim 4.
References Cited (Backward Citations)
US4105776A
Cited
US4192945A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-07-04 | 1987-01-03 | 1987-07-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-07-04 | 1991-01-03 | 1991-07-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-07-04 | 1995-01-03 | 1995-07-05 | $7700.00 | Window Closed / Lapsed |