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US4542234A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the separation of (S,S) diastereoisomers

Assignee: USV Pharmaceutical Corp
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Filing: 1983-10-06
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Granted: 1985-09-17
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Expires: 2003-10-06
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Abstract

Abstract The (S,S) optical isomer of a compound having the general formula ##STR1## wherein R and R 1-5 are as defined herein, is recovered essentially free of the (R,S) and (S,R) isomers, by forming a solution of the esters of the (S,S) and the (R,S) and/or (S,R) isomers of said compound, selectively precipitating an acid salt (e.g. maleate) of the (S,S) ester from the solution, and treating the precipitate to form the desired free acid.

Inventors

  • 👤 Laurence W. Reilly, Jr.
  • 👤 Jeffrey N. Barton

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 10:26
CPC Classifications
C; C07; C07C; C07C227/00; C07C227/30; C07C227/34

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 148 words
A process for separating the (S,S) diastereoisomer of a compound of the formula ##STR7## from a solution containing said (S,S) isomer and one or both of the corresponding (R,S) and (S,R) diastereoisomers in a non-polar, water-immiscible organic solvent selected from the group consisting of toluene, methylene chloride, diethyl ether, chloroform, ethyl acetate, and mixtures thereof, wherein R 6 is t-butyl or benzyl, comprising (i) reacting said diastereoisomers with an acid, selected from the group consisting of maleic, tartaric, p-nitrocinnamic, cinnamic, hippuric, citric, and 2,4-dichlorobenzoic acids, which forms acid addition salts with said diastereoisomers which salts are characterized in that the salts of the (R,S) and (S,R) diastereoisomers are soluble in said solution and said salt of the (S,S) diastereoisomer is not, under conditions wherein the salt of the (S,S) diastereoisomer selectively precipitates from said solution, and (ii) converting said precipitated salt to the (S,S) compound of formula (A).
Claim 2
Dependent Claim 148 words
A process for separating the (S,S) diastereoisomer of a compound of the formula ##STR7## from a solution containing said (S,S) isomer and one or both of the corresponding (R,S) and (S,R) diastereoisomers in a non-polar, water-immiscible organic solvent selected from the group consisting of toluene, methylene chloride, diethyl ether, chloroform, ethyl acetate, and mixtures thereof, wherein R 6 is t-butyl or benzyl, comprising (i) reacting said diastereoisomers with an acid, selected from the group consisting of maleic, tartaric, p-nitrocinnamic, cinnamic, hippuric, citric, and 2,4-dichlorobenzoic acids, which forms acid addition salts with said diastereoisomers which salts are characterized in that the salts of the (R,S) and (S,R) diastereoisomers are soluble in said solution and said salt of the (S,S) diastereoisomer is not, under conditions wherein the salt of the (S,S) diastereoisomer selectively precipitates from said solution, and (ii) converting said precipitated salt to the (S,S) compound of formula (A).
Claim 3
Dependent Claim 11 words
The process of claim 1 wherein the acid is maleic acid.
Claim 4
Dependent Claim 64 words
A process for forming a compound of the formula ##STR8## and having an (S,S) diastereomeric configuration, comprising (i) treating a solution of the (S,S) diastereoisomer of a compound of the formula ##STR9## and one or both of the corresponding (R,S) and (S,R) diastereoisomers in accordance with the process of claim 1; and (ii) converting the (S,S) diastereoisomer obtained by said process into compound (B).
Claim 5
Dependent Claim 11 words
The process of claim 3 wherein the acid is maleic acid.

References Cited (Backward Citations)

US3887606A Cited
US3976680A Cited
US3983162A Cited
US4344949A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-09-16 1989-03-18 1989-09-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-09-16 1993-03-18 1993-09-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-09-16 1997-03-18 1997-09-17 $7700.00 Window Closed / Lapsed

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