Ozanimod hydrochloride Chemical Properties

form 

Solid

color 

White to off-white

InChIKey

HAOOCAKHSFYDBU-OZYVVJTJNA-N

SMILES

N([C@H]1CCC2=C(C3=NOC(C4C=CC(OC(C)C)=C(C#N)C=4)=N3)C=CC=C12)CCO.Cl |&1:1,r|

Ozanimod hydrochloride Usage And Synthesis

Description

Ozanimod hydrochloride (RPC-1063 hydrochloride) is an orally available, selective and potent sphingosine 1-phosphate (S1P) receptor modulator that shows high affinity for S1P1 and S1P5. Ozanimod has potential anticancer activity and can be used in studying multiple sclerosis (MS), ulcerative multiple sclerosis (UMS), and other diseases. (MS), ulcerative colitis, coronavirus infections and myelodysplasia.

Chemical Properties

Ozanimod hydrochloride is a white to off-white solid with a melting point of ~240°C. It is poorly hygroscopic. The solubility of ozanimod hydrochloride in ethanol and methanol is 1.43 and 2.41 mg/mL; in a pH 5.1, aqueous medium is 3.51 mg/mL. The pKa for this compound is 7.90, and the partition coefficient (logP) is 3.28.

Uses

Ozanimod hydrochloride is an oral sphingosine 1-phosphate receptor modulator used to treat ulcerative colitis and other autoimmune diseases.

Synthesis

The carboxylic acid 187 (Western fragment) was activated using CDI (carbodiimide) and then coupled with the Eastern fragment 186 to form the oxadiazole 189. The crude product was used directly for the subsequent acetal deprotection without further purification. The deprotection reaction gave the ketone 190 in 76% yield from 187. The ketone 190 was condensed with 2-aminoethyl alcohol under Dean-Stark conditions to give the imine 191 in 96% yield. The chiral ruthenium complex 192 catalyzed the reduction of the imine 190 to give ozanimod 193 in high enantiomeric excess. Finally, the salt formation reaction with hydrochloric acid in methanol gave ozanimod hydrochloride in high yield.

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