Dinitrile intermediates for the synthesis of omapatrilat and methods for producing same
AssigneeDixie Chemical Company
InventorsJoseph C. Rongione, Robert G. Brown, Dwight E. Raff
Life of this patent
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Abstract
Omapatrilat (I) is a potent inhibitor of angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP) both in vitro and in vivo and is currently undergoing large scale clinical trials as an anti-hypertensive. Omapatrilat may be synthesized using the S-stereoisomer of a racemic mixture. The racemic mixture may be prepared from a hydantoin (III). The hydantoin may be prepared from a novel dinitrile compound (IV): The dinitrile may be produced by reacting a monoacetal with a non-carbonate ammonium salt and an alkali cyanide.
Claims20
A compound of the formula:
- wherein each R2 is independently represented by the formula:
- wherein R3, R4, R5, and R6 are independently selected from the group consisting of —H or a C1-C5 alkyl group and R7 and R8 are independently selected from the group consisting of a C1-C5 alkyl group.
A compound of the formula:
A process of preparing a compound of the formula:
- wherein each R2 is independently selected from
- and further wherein R3, R4, R5, and R6 are independently selected from the group consisting of —H or a C1-C5 alkyl group and R7 and R8 are independently selected from the group consisting of a C1-C5 alkyl group, said process comprising mixing in an aqueous medium a monoacetal having the formula:
- with a non-carbonate ammonium salt and an alkali cyanide for a time and at a temperature sufficient to generate the compound of formula (IV).
Dependencies are inferred from the claim text.