Process for making seladelpar
AssigneeCymaBay Therapeutics, Inc.
InventorsXin CHEN, Bharat GURALE, Dumitru IONESCU, Eric Jason KISER, Stephen STEFFKE, Hi TAING, Buchi VADDULA, Fei YU
Life of this patent
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Abstract
The present disclosure relates generally to processes for preparing seladelpar, an agonist of peroxisome proliferator-activated receptor (PPAR)-delta, and compositions thereof.
Claims27
A method of making a compound of formula I:
- or a pharmaceutically acceptable salt or hydrate thereof,
- comprising:
- contacting a compound of formula (A):
- or a salt thereof,
- with CH3CH2-LG, wherein LG is a leaving group,
- under conditions sufficient to form a compound of formula I or a pharmaceutically acceptable salt or hydrate thereof.
A method of making a compound of formula I:
- or a pharmaceutically acceptable salt or hydrate thereof,
- comprising:
- (a) contacting a compound of formula (B):
- with a compound of formula (C):
- or a salt thereof,
- under conditions sufficient to form a compound of formula (A):
- or a salt thereof;
- and (b) contacting a compound of formula (A), or a salt thereof, with CH3CH2-LG, wherein LG is a leaving group,
- under conditions sufficient to form a compound of formula I or a pharmaceutically acceptable salt or hydrate thereof.
A method of making a compound of formula I:
- or a pharmaceutically acceptable salt or hydrate thereof,
- comprising:
- (a) contacting a compound of formula (G):
- wherein R1 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, heterocyclyl, aryl, or heteroaryl;
- with CH3CH2-LG, wherein LG is a leaving group,
- in the presence of sodium hydroxide and dimethylsulfoxide (DMSO) and water,
- under conditions sufficient to form a compound of formula III:
- and (b) hydrolyzing the compound of formula III under conditions sufficient to form a compound of formula I or a pharmaceutically acceptable salt or hydrate thereof.
The method of any one of the preceding claims, further comprising:
- contacting a compound of formula I with L-lysine under conditions sufficient to form a lysine salt of a compound of formula I-a1:
A composition comprising a lysine salt of a compound of formula I-a:
- wherein the composition comprises less than about 2% a/a of a compound selected from:
- or a combination thereof.
A composition comprising a compound of formula I:
- or a pharmaceutically acceptable salt or hydrate thereof,
- wherein the composition comprises less than 0.1% a/a of a compound of formula II:
- or a pharmaceutically acceptable salt thereof.
A composition comprising a compound of formula I-b1:
- wherein the composition comprises less than 0.1% a/a of a compound of formula II-a:
A composition comprising a compound of formula I-b1:
- wherein the composition comprises at least about 97% w/w of the compound of formula I-b1, and less than about 2% w/w of a compound selected from:
- or a combination thereof.
Dependencies are inferred from the claim text.