IP Library Granted Patent US 9,663,505
Granted Patent B2
US 9,663,505 · App. 14/780,138 · Granted May 30, 2017

Process for the preparation of rivaroxaban

Inventors: Shrikant Prabhakar Keshav (Navi Mumbai, IN); Sanjay Shashikant Bhise (Mumbai, IN); Hemant Harishchandra Kamble (Mumbai, IN); Ganesh Chaudhari (Ahemdnagar, IN); Deepak Subhash Patil (Thane, IN); Srinivas Reddy Sanikommu (Andhra Pradesh, IN); Kumar Hari Bhushan (Gurgaon, IN); Shekhar Bhaskar Bhirud (Mumbai, IN)
Assignee: GLENMARK PHARMACEUTICALS LIMITED
C07D413/14C07D413/12
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Quick Facts
Patent No.
US 9,663,505
App. No.
14/780,138
Granted
May 30, 2017
Kind
B2
Abstract

Disclosed is a process for the preparation of rivaroxaban and purifying rivaroxaban.

Claims (21)

1. A process for the preparation of rivaroxaban, a compound of Formula I,

comprising the steps of

a) contacting a compound of Formula II or salt thereof

with an oxidizing agent to form a first reaction mixture;

b) contacting the first reaction mixture with a compound of formula VIII,

to form a second reaction mixture; and

c) isolating a compound of formula I from the second reaction mixture.

2. The process as claimed in claim 1 , wherein the oxidizing agent is selected from the group consisting of tert-butyl hydroperoxide, benzoyl peroxide and cumene hydro peroxide.

3. The process as claimed in claim 2 , wherein the oxidizing agent is tert-butyl hydroperoxide.

4. The process as claimed in claim 1 , wherein the amount of the oxidizing agent is from about 1 mole to about 3 moles per mole of the compound of formula II or salt thereof.

5. The process as claimed in claim 1 , wherein the contacting step (b) is carried out at about 25° C. to about 50° C.

6. The process as claimed in claim 1 , wherein the reaction is carried out at about 5° C. to about 80° C.

7. The process as claimed in claim 1 , wherein rivaroxaban, a compound of Formula I, is free of compound of formula XI

8. The process for purifying rivaroxaban, a compound of Formula I, as prepared in claim 1 , comprising:

a) providing a solution of rivaroxaban in a mixture of an alcohol solvent and a halogenated hydrocarbon solvent or their aqueous mixtures;

b) precipitating the solid from the solution; and

c) isolating the pure rivaroxaban, a compound of Formula I.

9. The process as claimed in claim 8 , wherein the alcoholic solvent is methanol.

10. The process as claimed in claim 8 , wherein the halogenated hydrocarbon solvents dichloromethane.

11. Rivaroxaban, a compound of Formula I,

containing less than about 0.15% w/w as measured by HPLC of the compound of formula XI

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 27, 2019
From: GLENMARK PHARMACEUTICALS LIMITED
To: GLENMARK LIFE SCIENCES LIMITED
Reel/Frame 050179/0351 →
CONFIDENTALITY & SECRECY AGREEMENT Recorded Feb 1, 2017
From: REDDY, SANIKOMMU SRINIVAS
To: GLENMARK GENERICS LIMITED
Reel/Frame 041588/0191 →
MERGER Recorded Feb 1, 2017
From: GLENMARK GENERICS LIMITED
To: GLENMARK PHARMACEUTICALS LIMITED
Reel/Frame 041588/0745 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 16, 2015
From: KESHAV, SHRIKANT PRABHAKAR; BHISE, SANJAY SHASHIKANT; KAMBLE, HEMANT HARISHCHANDRA; CHAUDHARI, GANESH; PATIL, DEEPAK SUBHASH; BHUSHAN, KUMAR HARI; BHIRUD, SHEKHAR BHASKAR
To: GLENMARK PHARMACEUTICALS LIMITED
Reel/Frame 037302/0758 →
Priority Claims (1)
IN 1113/MUM/2013 · Mar 25, 2013 · national
Continuity (1)
Related Publication 20160052919A1 · Feb 25, 2016