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US 2014/0155588 A1Published application
Azacitidine process and polymorphs
AssigneeDr. Reddy's Laboratories, Inc.
InventorsPraveen CHERUKUPALLY, Satish Kumar VUJJINI, Ganesh VARANASI, Sreenadha Charyulu KANDALA, Srinivas AREVELI, Satyanarayana Raju TIRUMALARAJU
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Abstract
Processes for preparing azacitidine. Further included are processes for the preparation of crystalline azacitidine crystalline Form I and mixtures of azacitidine crystalline Forms I and II.
Claims22
A process for preparing azacitidine, comprising:
- a) silylating 5-azacytosine to give a compound of Formula II,
- wherein R1 is an optionally substituted C1-C5 alkyl group;
- b) coupling a compound of Formula II with a compound of Formula III:
- wherein R2 is an optionally substituted acyl or aroyl group, in the presence of a non-Lewis acid compound to provide a compound of Formula V;
- and
- c) converting a compound of Formula V to azacitidine.
3 more elements
A process for preparing azacitidine, comprising converting a compound of Formula V,
- wherein R2 is an optionally substituted acyl or aroyl group, to azacitidine in the presence of an alkylamine and a C1-C4 alcohol.
A process for preparing azacitidine, comprising:
- a) silylating 5-azacytosine to give a compound of Formula II,
- wherein R1 is an optionally substituted C1-C5 alkyl group;
- b) coupling a compound of Formula II with a compound of Formula III:
- wherein R2 is an optionally substituted acyl or aroyl group, using a non-Lewis acid compound, metallic Lewis acid, or TMS-triflate coupling agent, in the presence of an ester solvent, to provide a compound of Formula V;
- and
- b) converting a compound of Formula V to azacitidine.
3 more elements
-38. (canceled)
Dependencies are inferred from the claim text.