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US4334077A Expired / Lapsed US ⏱️ 0.0 years remaining

Stereospecific sulfoxidation of dibenzo thiepins

Assignee: Merck and Co Inc
•
Filing: 1981-01-28
•
Granted: 1982-06-08
•
Expires: 2001-01-28
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Abstract

Abstract The present invention relates to a process for the preparation of an enantiomer of 7 or 8-fluoro-dibenzo[b,f]thiepin-3-carboxylic acid having a negative rotation and prostaglandin antagonist activity. The process involves preparation and separation of novel diastereoisomeric esters of 10-hydroxy-7 or 8 fluro-dibenzothiepin-3 carboxylic acid ester followed by stereospecific sulfoxidation of the selected diastereoisomer to produce the corresponding novel sulfoxide having a preponderance of the desired configuration of the sulfoxide entity followed by treatment of the product with a strong base to produce directly the desired (-)7 or 8 fluoro-dibenzo[b,f]thiepin-3 carboxylic acid 5-oxide having the structural formula shown below: ##STR1##

Inventors

  • 👤 Patrice C. Belanger
  • 👤 Joshua Rokach
  • 👤 Robert N. Young
  • 👤 John Scheigetz

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 13:42
CPC Classifications
C; C07; C07D; C07D337/00; C07D337/02; C07D337/06; C07D337/10; C07D337/14

Claims Analysis

Total Claims: 4
Claim 1
Independent Claim 37 words
A compound of the formula: ##STR5## wherein the F substituent is attached to the 7 or 8 carbon; R* is an α-substituted benzyl substituent selected from α-methoxy-α-trifluoromethylbenzyl and α-methoxy benzyl; and R is a lower alkyl substituent.
Claim 2
Dependent Claim 37 words
A compound of the formula: ##STR5## wherein the F substituent is attached to the 7 or 8 carbon; R* is an α-substituted benzyl substituent selected from α-methoxy-α-trifluoromethylbenzyl and α-methoxy benzyl; and R is a lower alkyl substituent.
Claim 3
Dependent Claim 11 words
A compound according to claim 1 which comprises cis 10-R-((-)-α-methoxy-α-trifluoro-methylphenylacetoxy)8-fluoro-3-carbomethoxydibenzo [b,f]thiepin-5-oxide.
Claim 4
Dependent Claim 12 words
A compound according to claim 1 which comprises cis 10-R-((-)-α-methoxyphenylacetyl) 8-fluoro-3-carbomethoxydibenzo [b,f]thiepin-5-oxide.

References Cited (Backward Citations)

US3509154A Cited
US4104280A Cited
US4237160A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-06-07 1985-12-07 1986-06-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-06-07 1989-12-07 1990-06-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-06-07 1993-12-07 1994-06-08 $7700.00 Window Closed / Lapsed

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