Back to results
US 7,078,543 B2Granted
Methods for producing oxirane carboxylic acids and derivatives thereof
AssigneeMediGene AG
InventorsMagnus Cernerud, Kristina Berntsson
Life of this patent
Estimating the term…
Abstract
The invention relates to processes for preparing oxiranecarboxylic acids and derivatives thereof, in particular to processes which proceed under stereochemical control of the reaction steps, to the oxiranecarboxylic acids prepared according to the invention and derivatives thereof and to their use in pharmaceutical compositions, in particular for treating hyperlipaemia.
Claims13
A process for preparing oxiranecarboxylic acids and derivatives thereof, comprising the synthesis of a compound of the formula (X):
- in which
- R1 is a straight-chain or branched mono-, poly-, or unsubstituted alkyl group;
- a straight-chain or branched mono-, poly-, or unsubstituted alkylene group;, a straight-chain or branched mono-, poly-, or unsubstituted aralkyl or alkylaryl group;
- or a mono-, poly- or unsubstituted aryl group, and
- R6 is selected from the group consisting of OH;
- O−M+;
- O−M2+, where M is an alkali metal, an alkaline earth metal, an earth metal, or a cation of an organic nitrogen base;
- and OR, where R is a substituted or unsubstituted alkyl or alkylene group having 1 to 15 carbon atoms,
- comprising the steps:
- (a) reacting a compound of the formula (V) with an amine of the formula (VI) to give a compound of the formula (VII):
- in which
- R1 is as defined above, and
- R4 and R5 are identical or different straight-chain or branched mono-, poly-, or unsubstituted alkyl groups;
- straight-chain or branched mono-, poly-, or unsubstituted alkylene groups;
- straight-chain or branched mono-, poly-, or unsubstituted aralkyl or alkylaryl groups;
- or mono-, poly-, or unsubstituted aryl groups, where R4NCR5 may be part of a substituted or unsubstituted cyclic structure which may contain a heteroatom selected from the group consisting of N, S, and O;
- (b) converting a compound of the formula (VII) into a lactone of the formula (VIII):
- in which
- R1, R4, and R5 are as defined above,
- R1 and R4NCR5 are not simultaneously —(CH2)6—OBn, wherein Bn represents benzyl, and an unsubstituted five-membered ring, respectively, and
- X4 is a functional group capable of forming a cationic intermediate in a reaction with a C—C double bond and is a good leaving group;
- (c) converting a lactone of the formula (VIII) into a compound of the formula (IX):
- in which
- R1, R4, R5, R6, and X4 are as defined above, and
- R1 and R4NCR5 are not simultaneously —(CH2)6—OBn, wherein Bn represents benzyl, and an unsubstituted five-membered ring, respectively;
- and
- (d) converting a compound of the formula (IX) into the compound of the formula (X):
- in which R1, R6, and X4 are as defined above.
25 more elements
Dependencies are inferred from the claim text.