U.S. patent application number 12/403709 was filed with the patent office on 2009-09-10 for pharmaceutical compositions of valdecoxib.
This patent application is currently assigned to HETERO DRUGS LIMITED. Invention is credited to Bandi Parthasaradhi Reddy, Dasari Muralidhara Reddy, Kesireddy Subadsh Chander Reddy, Kura Rathnakar Reddy, Rapolu Raji Reddy.
Application Number | 20090227645 12/403709 |
Document ID | / |
Family ID | 33104984 |
Filed Date | 2009-09-10 |
United States Patent
Application |
20090227645 |
Kind Code |
A1 |
Reddy; Bandi Parthasaradhi ;
et al. |
September 10, 2009 |
PHARMACEUTICAL COMPOSITIONS OF VALDECOXIB
Abstract
The present invention relates to novel crystalline forms of
valdecoxib, to processes for their preparation and to
pharmaceutical compositions containing them.
Inventors: |
Reddy; Bandi Parthasaradhi;
(Hyderabad, IN) ; Reddy; Kura Rathnakar;
(Hyderabad, IN) ; Reddy; Rapolu Raji; (Hyderabad,
IN) ; Reddy; Dasari Muralidhara; (Hyderabad, IN)
; Reddy; Kesireddy Subadsh Chander; (Hyderabad,
IN) |
Correspondence
Address: |
CAESAR, RIVISE, BERNSTEIN,;COHEN & POKOTILOW, LTD.
11TH FLOOR, SEVEN PENN CENTER, 1635 MARKET STREET
PHILADELPHIA
PA
19103-2212
US
|
Assignee: |
HETERO DRUGS LIMITED
Hyderabad
IN
|
Family ID: |
33104984 |
Appl. No.: |
12/403709 |
Filed: |
March 13, 2009 |
Related U.S. Patent Documents
|
|
|
|
|
|
Application
Number |
Filing Date |
Patent Number |
|
|
10510333 |
Oct 5, 2004 |
7538126 |
|
|
PCT/IN03/00139 |
Apr 4, 2003 |
|
|
|
12403709 |
|
|
|
|
Current U.S.
Class: |
514/378 |
Current CPC
Class: |
C07D 261/08 20130101;
A61P 29/00 20180101 |
Class at
Publication: |
514/378 |
International
Class: |
A61K 31/42 20060101
A61K031/42; A61P 29/00 20060101 A61P029/00 |
Foreign Application Data
Date |
Code |
Application Number |
Apr 4, 2003 |
IN |
PCT/IN03/00139 |
Claims
1-14. (canceled)
15. A pharmaceutical composition comprising stable valdecoxib form
I characterized by an x-ray powder diffraction pattern having peaks
expressed as 2.theta. at about 9.7, 13.1, 14.0, 14.5, 17.0, 17.1,
17.7, 19.4, 20.9, 21.3, 21.8, 24.1, 25.4, 26.3 and 29.1 degrees and
a pharmaceutically acceptable carrier or diluent.
16-17. (canceled)
18. The pharmaceutical composition of claim 15, wherein the
valdecoxib form I is further characterized by an x-ray powder
diffraction pattern as in FIG. 1.
19. The pharmaceutical composition of claim 15, wherein the
valdecoxib form I is prepared by a process which comprises the
steps of: (a) dissolving valdecoxib in dimethyl formamide or
N,N-dimethyl acetamide; and (b) isolating valdecoxib form I from
the solution.
20. The pharmaceutical composition of claim 19, wherein valdecoxib
is dissolved in dimethyl formamide.
21. The pharmaceutical composition of claim 19, wherein the
solution formed in (a) is cooled to 25.degree. C. to 30.degree. C.
and the separated crystals are collected by filtration or
centrifugation.
Description
FIELD OF THE INVENTION
[0001] The present invention relates to novel crystalline forms of
valdecoxib, to processes for their preparation and to
pharmaceutical compositions containing them.
BACKGROUND OF THE INVENTION
Valdecoxib of Formula (I)
##STR00001##
[0002] or 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide is a
highly selective and potent cyclooxygenase-2 inhibitor in human
whole blood and useful for the treatment of arthritis and pain. The
therapeutic uses of valdecoxib are disclosed in WO 9625405.
[0003] Two crystalline forms of valdecoxib, form A and form B, are
mentioned in WO 9806708.
[0004] We have discovered three stable novel crystalline forms of
valdecoxib and these forms are found to be suitable for
pharmaceutical preparations.
[0005] The object of the present invention is to provide stable
novel crystalline forms of valdecoxib, processes for preparing
these forms and pharmaceutical compositions containing them.
DETAILED DESCRIPTION OF THE INVENTION
[0006] In accordance with the present invention, there is provided
a novel crystalline form of valdecoxib, designated as form 1,
characterized by an x-ray powder diffraction pattern having peaks
expressed as 2.theta. at about 9.7, 13.1, 14.0, 14.5, 17.0, 17.1,
17.7, 19.4, 20.9, 21.3, 21.8, 24.1, 25.4, 26.3 and 29.1 degrees.
FIG. 1 shows typical form I x-ray powder diffraction pattern.
[0007] In accordance with the present invention, a process is
provided for preparation of valdecoxib form I. In this process,
valdecoxib is dissolved in dimethyl formamide or N,N-dimethyl
acetamide and valdecoxib form I is isolated from the solution.
Valdecoxib in any crystalline form may be used. If valdecoxib form
I is used in the process, its serves as a method of purification of
valdecoxib form I. A mixture of dimethyl formamide and N,N-dimethyl
acetamide; or dimethyl formamide or N,N-dimethyl acetamide mixed
with any other solvent may be used. Valdecoxib form I can be
isolated by the techniques like cooling, partial removal of the
solvent or combination thereof. Crystallization may be initiated
with the aid of seed crystals. Preferably, valdecoxib is mixed with
dimethyl formamide or N,N-dimethyl acetamide and heated to about
50.degree. C. to reflux temperature. The solution so formed is
preferably maintained at 25.degree. C. to 30.degree. C. for 3 to 5
hours and the valdecoxib form I crystals formed are separated by
filtration or centrifugation.
[0008] In accordance with the present invention, there is provided
a novel crystalline form of valdecoxib, designated as form II,
characterized by an x-ray powder diffraction pattern having peaks
expressed as 2.theta. at about 12.2, 15.4, 15.9, 19.9, 20.6, 22.0,
23.0, 23.6, 23.9, 24.5, 25.1, 28.6 and 31.3 degrees. FIG. 2 shows
typical form II x-ray powder diffraction pattern.
[0009] In accordance with the present invention, a process is
provided for preparation of valdecoxib form II. In this process,
valdecoxib is dissolved in acetonitrile and isolated valdecoxib
form II from the solution. Valdecoxib in any crystalline form may
be used. Preferably valdecoxib is dissolved in acetonitrile at
about 40.degree. C. to 45.degree. C. and valdecoxib form II is
separated at about 25.degree. C.-30.degree. C. The valdecoxib form
II may be collected by filtration or centrifugation.
[0010] In accordance with the present invention, there is provided
a novel crystalline form of valdecoxib, designated as form III,
characterized by an x-ray powder diffraction pattern having peaks
expressed as 2.theta. at about 11.6, 12.2, 12.9, 13.3, 15.4, 15.7,
16.7, 17.0, 17.4, 18.1, 19.7, 20.6, 21.9, 22.4, 23.1, 23.4, 23.8,
24.4, 25.3, 25.7, 26.1, 28.5 and 29.7 degrees. FIG. 3 shows typical
form III x-ray powder diffraction pattern.
[0011] In accordance with the present invention, a process is
provided for preparation of valdecoxib form III. In this process,
valdecoxib is dissolved in an ester solvent and isolated valdecoxib
form III from the solution. Preferably the solution is cooled to
5.degree. C. to 30.degree. C. to get the crystals of valdecoxib
form III. The valdecoxib form III may be collected by filtration or
centrifugation. Valdecoxib in any crystalline form may be used in
the process. The suitable ester solvent is selected from n-butyl
acetate, ethyl acetate, methyl acetate, isopropyl acetate,
tert-butyl acetate, ethyl formate, methyl formate. A combination of
the ester solvents may also be used.
[0012] In accordance with the present invention, there is provided
a pharmaceutical composition comprising form I of valdecoxib and a
pharmaceutically acceptable carrier or diluent.
[0013] In accordance with the present invention, there is provided
a pharmaceutical composition comprising form II of valdecoxib and a
pharmaceutically acceptable carrier or diluent.
[0014] In accordance with the present invention, there is provided
a pharmaceutical composition comprising form III of valdecoxib and
a pharmaceutically acceptable carrier or diluent.
BRIEF DESCRIPTION OF THE DRAWINGS
[0015] FIG. 1 is a x-ray powder diffraction spectrum of valdecoxib
form I.
[0016] FIG. 2 is a x-ray powder diffraction spectrum of valdecoxib
form II.
[0017] FIG. 3 is a x-ray powder diffraction spectrum of valdecoxib
form III.
[0018] x-Ray powder diffraction spectrum was measured on a Siemens
D5000 x-ray powder diffractometer having a copper-K.alpha.
radiation.
[0019] The following examples are given for the purpose of
illustrating the present invention and should not be considered as
limitations on the scope of spirit of the invention.
Example 1
[0020] Valdecoxib (10 gm, obtained by the process described in
example 1 of WO 9625405) is dissolved in dimethyl formamide (50
ml), heated to 50.degree. C. and the solution obtained is cooled to
25.degree. C. and maintained at 25.degree. C. to 30.degree. C. for
3 hours. The separated crystals are filtered to give 9 gm of
valdecoxib form I.
Example 2
[0021] Valdecoxib (10 gm) is dissolved in acetonitrile (125 ml),
heated to 40.degree. C. and the solution obtained is cooled to
25.degree. C. and maintained at 25.degree. C. to 30.degree. C. for
6 hours. The separated crystals are filtered to give 9.5 gm of
valdecoxib form II.
Example 3
[0022] Example 1 is repeated using valdecoxib form II for
valdecoxib to give valdecoxib form I.
Example 4
[0023] Example 2 is repeated using valdecoxib form I for valdecoxib
to give valdecoxib form II.
Example 5
[0024] Valdecoxib (10 gm) is mixed with n-butyl acetate (100 ml),
heated to 80.degree. C. The solution so formed is cooled to
25.degree. C. and maintained at about 25.degree. C. for 5 hours.
The separated crystals are filtered to give 8.5 gm of valdecoxib
form III.
Example 6
[0025] Example 5 is repeated using valdecoxib form II for
valdecoxib to give valdecoxib form III.
* * * * *