IP Library Granted Patent US 9,085,592
Granted Patent B2
US 9,085,592 · App. 13/496,281 · Granted Jul 21, 2015

Process for the preparation of fosamprenavir calcium

Inventors: Satish Manohar Bhoge (Ahmed Nagar, IN); Prakash Kshirsagar (Pune, IN); Santosh Richhariya (Sagar, IN); Kaptan Singh (Ghaziabad, IN)
Assignee: RANBAXY LABORATORIES LIMITED
C07F9/65515
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Quick Facts
Patent No.
US 9,085,592
App. No.
13/496,281
Granted
Jul 21, 2015
Kind
B2
Abstract

The present invention relates to process for the preparation of fosamprenavir calcium.

Claims (14)

1. A process for the preparation of fosamprenavir calcium, wherein the process comprises

a) treating (3S)-tetrahydrofuran-3-yl[(2S,3R)-4-{(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino}-1-phenyl-3-(phosphonooxy)butan-2-yl]carbamate of Formula II

or a starting salt of (3S)-tetrahydrofuran-3-yl[(2S,3R)-4-{(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino}-1-phenyl-3-(phosphonooxy)butan-2-yl]carbamate of Formula II, with a source of calcium ions, to obtain a calcium salt of the compound (3S)-tetrahydrofuran-3-yl[(2S,3R)-4-{(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino}-1-phenyl-3-(phosphonooxy)butan-2-yl]carbamate of Formula II, wherein the starting salt is selected from lithium, sodium, potassium, magnesium, and ammonium;

b) isolating the solid calcium salt of the compound (3S)-tetrahydrofuran-3-y1[(2S,3R)-4-{(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino}-1-phenyl-3-(phosphonooxy)butan-2-yl]carbamate of Formula II from the reaction mixture thereof;

c) reducing the nitro group of the calcium salt of the compound (3S)-tetrahydrofuran-3-yl[(2S,3R)-4-{(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino}-1-phenyl-3-(phosphonooxy)butan-2-yl]carbamate of Formula II to an amino group; and

d) isolating fosamprenavir calcium from the reaction mixture thereof.

2. The process according to claim 1 , wherein the reduction is carried out using a reducing agent which does not use hydrogen gas or which uses hydrogen gas and a hydrogenation catalyst.

3. The process according to claim 1 , wherein the reduction is carried out in the presence of a solvent.

4. The process according to claim 3 , wherein the solvent is C 1-3 alkanol, ethyl acetate, water, acetone, denaturated or industrial methylated spirit or a mixture thereof.

5. The process according to claim 1 , wherein step a) is carried out in the presence of a solvent system comprising an organic solvent, water or a mixture thereof.

6. The process according to claim 5 , wherein the organic solvent is a water miscible organic solvent.

7. The process according to claim 6 , wherein the water miscible organic solvent is a C 1-3 alkanol.

8. The process according to claim 1 , wherein the source of calcium ions is calcium acetate, calcium chloride or calcium hydroxide.

9. The process according to claim 1 wherein the starting salt used in step a) is a sodium or potassium salt.

Assignments (2)
MERGER Recorded Jan 13, 2016
From: RANBAXY LABORATORIES LIMTED
To: SUN PHARMACEUTICAL INDUSTRIES LIMITED
Reel/Frame 037513/0475 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 15, 2012
From: BHOGE, SATISH MANOHAR; KSHIRSAGAR, PRAKASH; RICHHARIYA, SANTOSH; SINGH, KAPTAN
To: RANBAXY LABORATORIES LIMITED
Reel/Frame 027868/0397 →
Priority Claims (1)
IN 1933/DEL/2009 · Sep 16, 2009 · national
Continuity (1)
Related Publication 20120220786A1 · Aug 30, 2012