Process for preparation of eletriptan and salt thereof
AssigneeUSV Limited B.S.D. Mar
InventorsDhananjay Govind Sathe, Subhash Vishwanath Damle, Subodh Shashikant Patnekar, Prashant Vijay Joshi, Samadhan Daulat Patil
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Abstract
The present invention relates to an improved process for the preparation of 3-(N-methyl-2(R)-pyrrolidinyl methyl)-5-[2-(phenyl sulfonyl)ethyl]-1H-indole or pharmaceutically acceptable salts thereof, particularly 3-(N-methyl-2(R)-pyrrolidinyl methyl)-5-[2-(phenyl sulfonyl)ethyl]-1H-indole hydrobromide (Eletriptan hydrobromide). The present invention further relates to novel polymorphs of 3-(N-methyl-2(R)-pyrrolidinyl methyl)-5-[2-(phenyl sulfonyl)ethenyl]-1H-indole hydrobromide and process for preparation thereof.
Claims16
A process for preparation of Eletripan hydrobromide comprising,
- a) coupling 3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-bromo-1H-indole with phenyl vinyl sulfone to obtain a mixture containing 3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-[2-(phenylsulfonyl)ethenyl]-1H-indole hydrobromide;
- b) isolating 3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-[2-(phenylsulfonyl)ethenyl]-1H-indole hydrobromide as a solid;
- c) converting said solid 3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-[2-(phenylsulfonyl)ethenyl]-1H-indole hydrobromide to 3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-[2-(phenylsulfonyl)ethyl]-1H-indole hydrobromide (Eletriptan hydrobromide).
3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-[2-(phenylsulfonyl)ethenyl]-1H-indole hydrobromide characterized by X-ray diffraction pattern having peaks at 2-theta values of about 11.47, 12.63, 14.41, 15.09, 18.42, 19.77, 22.22, 23.18, 23.90, 25.23, 26.94, 28.33, 29.90 and 30.85 degrees;
- or by X-ray diffraction pattern having peaks at 2-theta values of about 10.12, 11.34, 13.87, 15.63, 16.09, 16.43, 18.32, 19.95, 20.39, 20.90, 21.82, 22.75, 24.16, 24.37, 24.93, 25.69, 27.47, 27.91 and 28.85 degrees.
A process for preparation of Eletriptan hydrobromide, wherein the process comprises treating 3-(N-methyl-2(R)-pyrrolidinyl methyl)-5-[2-(phenyl sulfonyl)ethyl]-1H-indole hydrobromide having inadequate HBr content with HBr to obtain Eletriptan hydrobromide with required hydrobromide content.
3-[N-Methyl-2(R)-pyrrolidinylmethyl]-1,5-bis-(2-phenylsulfonylethyl)indole prepared by a process comprising treating 3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-[2-(phenyl sulfonyl)ethyl]-1H-indole (Eletriptan base) with phenylvinyl sulfone in presence of a base.
Dependencies are inferred from the claim text.