Preparation of deoxycholic acid
AssigneeCrystal Pharma, S.A.U.
InventorsAntonio LORENTE BONDE-LARSEN, Ignacio HERRAIZ SIERRA, Yolanda FERNANDEZ SAINZ, Jose Luis BARREDO FUENTE, Alfonso PEREZ ENCABO, Jose Angel TURIEL HERNANDEZ, Francisco Javier GUERRA NAVARRO
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Abstract
The present invention relates to new and improved processes for the preparation of deoxycholic acid (DCA) and pharmaceutically acceptable salts thereof, as well as to DCA and pharmaceutically acceptable salts thereof, the carbon atoms of which are derived solely from plant sources.
Claims25
A method of making deoxycholic acid or a pharmaceutically acceptable salt thereof of formula (DCA)
- said method comprising:
- providing a compound of formula Int A8:
- and
- converting the primary alcohol in the formula Int A8 into a leaving group (X) to obtain an intermediate of formula Int A9:
- wherein X is halogen, O-tosyl, or OP, wherein P is an alcohol protecting group;
- and
- elongating the carbon chain of the compound of the formula Int A9 to obtain DCA:
- wherein all carbon atoms of the DCA or the pharmaceutically acceptable salt thereof are solely from plant sources.
A method of making a compound of the general formula II or a pharmaceutically acceptable salt thereof
- wherein
- R1 is OH, NHCH2CH2SO3H or NHCH2COOH and
- R2 and R3 is H or OH, said method comprising:
- converting a compound of the general formula I
- wherein
- R1 is COOR2, CH2OH, CH2OP, CH2X, CH2CHO, CH2—CH2—OH, CH2—CH2OP, CH2—CH2X or CH2—CH2—CHO;
- R2 is H or a linear or branched C1-C6-alkyl group;
- P is an alcohol protection group;
- X is a halogen atom;
- is either a C—C bond or a C═C bond;
- is either ═O or OR3 where R3 is either P or R2;
- and
- OR4 is either OH or R4 is the C3 carbon in the A ring;
- under conditions to form the compound of the general formula II or a pharmaceutically acceptable salt thereof;
- wherein all carbon atoms of the compound of formula II or the pharmaceutically acceptable salt thereof are solely from plant sources.
Dependencies are inferred from the claim text.