WO2004092143A1 - A novel crystalline form of risperidone - Google Patents
A novel crystalline form of risperidone Download PDFInfo
- Publication number
- WO2004092143A1 WO2004092143A1 PCT/IN2003/000157 IN0300157W WO2004092143A1 WO 2004092143 A1 WO2004092143 A1 WO 2004092143A1 IN 0300157 W IN0300157 W IN 0300157W WO 2004092143 A1 WO2004092143 A1 WO 2004092143A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- risperidone
- crystalline form
- novel crystalline
- ray powder
- solvent
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Definitions
- the present invention relates to a novel crystalline form of risperidone, to a process for its preparation and to a pharmaceutical composition containing it.
- Risperidone chemically 3-[2-[4-(6-Fluoro-1 ,2-benzisoxazol-3-yl)-1- piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1 ,2-a]pyrimidin-4-one is known to be useful for the treatment of psychotic diseases.
- the chemical structure of risperidone is:
- the object of the present invention is to provide a novel crystalline form of risperidone, process for preparing it and a pharmaceutical composition containing it.
- a novel crystalline form of risperidone designated as form C, characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 6.8, 10.5, 11.3, 14.0, 14.7, 15.3, 16.3, 18.3, 18.8, 19.6, 21.1 , 22.3, 23.0, 25.1 , 28.3 and 28.8 degrees.
- Figure 1 shows typical form C x-ray powder diffraction pattern.
- a process is provided for preparation of risperidone form C.
- risperidone is dissolved in a suitable solvent and risperidone form C is isolated from the solution.
- Risperidone in any crystalline form may also be used in the process.
- Risperidone form C can be isolated by the techniques like cooling, partial removal of the solvent, using an anti-solvent or combination thereof.
- the suitable solvents are selected from the group consisting of tetrahydrofuran, 1 ,4-dioxane, diethyl ketone and a mixture of methyl tert-butyl ether and dimethylformamide.
- Preferable solvents are 1 ,4- dioxane and tetrahydrofuran.
- a pharmaceutical composition comprising form C of risperidone and a pharmaceutically acceptable carrier or diluent.
- Figure 1 is a x-ray powder diffraction spectrum of risperidone form C. x-Ray powder diffraction spectrum was measured on a Siemens D5000 x- ray powder diffractometer having a copper-K ⁇ radiation.
- Example 1 Risperidone (5.0 gm, obtained by the process described in example 5 of EP 0196132) is mixed with 1 ,4-dioxane (50 ml), heated to about 60°C and stirred for 1 hour at 60°C to 65°C. The solution obtained is slowly cooled to 25°C and stirred for 6 hours at 25°C to 30°C. The contents are cooled to 0°C and the solid is isolated by filtration to give 3.1 gm of risperidone form C.
- EP 0196132 is mixed with tetrahydrofuran (25 ml), heated to about 56°C and the solution obtained is slowly cooled to 25°C and stirred for 2 hours at 25°C to 30°C. The contents are then cooled to 0°C and the solid is filtered off and dried to give 3.5 gm of risperidone form C.
Abstract
A novel crystalline form of 3-[2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (risperidone) and a pharmaceutical composition comprising it.
Description
A NOVEL CRYSTALLINE FORM OF RISPERIDONE
FIELD OF THE INVENTION
The present invention relates to a novel crystalline form of risperidone, to a process for its preparation and to a pharmaceutical composition containing it.
BACKGROUND OF THE INVENTION
Risperidone, chemically 3-[2-[4-(6-Fluoro-1 ,2-benzisoxazol-3-yl)-1- piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1 ,2-a]pyrimidin-4-one is known to be useful for the treatment of psychotic diseases. The chemical structure of risperidone is:
The synthesis and therapeutic uses of risperidone are disclosed in EP 0196132.
Preparation of two crystalline forms of risperidone, form A and form B, are described in US 2002/0193386.
We discovered a novel crystalline form of risperidone. The novel crystalline form is stable and is not spontaneously converted to other forms of risperidone. The novel form is distinguishable from other forms by x-ray diffractions. The object of the present invention is to provide a novel crystalline form of risperidone, process for preparing it and a pharmaceutical composition containing it.
DETAILED DESCRIPTION OF THE INVENTION
In accordance with the present invention, there is provided a novel crystalline form of risperidone, designated as form C, characterized by an x-ray powder diffraction pattern having peaks expressed as 2Θ at about 6.8, 10.5, 11.3, 14.0, 14.7, 15.3, 16.3, 18.3, 18.8, 19.6, 21.1 , 22.3, 23.0, 25.1 , 28.3 and 28.8 degrees. Figure 1 shows typical form C x-ray powder diffraction pattern.
In accordance with the present invention, a process is provided for preparation of risperidone form C. Thus, risperidone is dissolved in a suitable solvent and risperidone form C is isolated from the solution. Risperidone in any crystalline form may also be used in the process. Risperidone form C can be isolated by the techniques like cooling, partial removal of the solvent, using an anti-solvent or combination thereof. The suitable solvents are selected from the group consisting of tetrahydrofuran, 1 ,4-dioxane, diethyl ketone and a mixture of methyl tert-butyl ether and dimethylformamide. Preferable solvents are 1 ,4- dioxane and tetrahydrofuran.
In accordance with the present invention, there is provided a pharmaceutical composition comprising form C of risperidone and a pharmaceutically acceptable carrier or diluent.
BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a x-ray powder diffraction spectrum of risperidone form C. x-Ray powder diffraction spectrum was measured on a Siemens D5000 x- ray powder diffractometer having a copper-Kα radiation.
The following examples are given for the purpose of illustrating the present invention and should not be considered as limitations on the scope or spirit of the invention.
Example 1 Risperidone (5.0 gm, obtained by the process described in example 5 of EP 0196132) is mixed with 1 ,4-dioxane (50 ml), heated to about 60°C and stirred for 1 hour at 60°C to 65°C. The solution obtained is slowly cooled to 25°C
and stirred for 6 hours at 25°C to 30°C. The contents are cooled to 0°C and the solid is isolated by filtration to give 3.1 gm of risperidone form C.
Example 2 Risperidone (5.0 gm, obtained by the process described in example 5 of
EP 0196132) is mixed with tetrahydrofuran (25 ml), heated to about 56°C and the solution obtained is slowly cooled to 25°C and stirred for 2 hours at 25°C to 30°C. The contents are then cooled to 0°C and the solid is filtered off and dried to give 3.5 gm of risperidone form C.
Claims
1. A crystalline risperidone form C, characterized by an x-ray powder diffraction pattern having peaks expressed as 2Θ at about 6.8, 10.5, 11.3, 14.0, 14.7, 15.3, 16.3, 18.3, 18.8, 19.6, 21.1 , 22.3, 23.0, 25.1 , 28.3 and 28.8 degrees.
2. A crystalline risperidone form C as defined in claim 1 , further characterized by an x-ray powder diffraction pattern as in figure 1.
3. A process for preparation of risperidone form C as defined in claim 1 , which comprises the steps of: a) dissolving risperidone in a suitable solvent; and b) isolating risperidone form C from the solution; wherein the suitable solvent is selected from the group consisting of tetrahydrofuran, 1 ,4-dioxane, diethyl ketone and a mixture of methyl tert-butyl ether and dimethylformamide. 4. A process according to claim 3, wherein su itable solvent is 1 ,
4-dioxane.
5. A process according to claim 3, wherein su table solvent is tetrahydrofuran.
6. A pharmaceutical composition comprising ri speridone form C of claim 1 and a pharmaceutically acceptable carrier or diluent.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2003/000157 WO2004092143A1 (en) | 2003-04-16 | 2003-04-16 | A novel crystalline form of risperidone |
| AU2003245028A AU2003245028A1 (en) | 2003-04-16 | 2003-04-16 | A novel crystalline form of risperidone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2003/000157 WO2004092143A1 (en) | 2003-04-16 | 2003-04-16 | A novel crystalline form of risperidone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2004092143A1 true WO2004092143A1 (en) | 2004-10-28 |
Family
ID=33187211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2003/000157 WO2004092143A1 (en) | 2003-04-16 | 2003-04-16 | A novel crystalline form of risperidone |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2003245028A1 (en) |
| WO (1) | WO2004092143A1 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002014286A1 (en) * | 2000-08-14 | 2002-02-21 | Teva Pharmaceutical Industries Ltd. | Preparation of risperidone |
-
2003
- 2003-04-16 AU AU2003245028A patent/AU2003245028A1/en not_active Abandoned
- 2003-04-16 WO PCT/IN2003/000157 patent/WO2004092143A1/en not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002014286A1 (en) * | 2000-08-14 | 2002-02-21 | Teva Pharmaceutical Industries Ltd. | Preparation of risperidone |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003245028A1 (en) | 2004-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2683040C (en) | Polymorphic forms of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoylbenzofuran-5-yl)piperazine hydrochloride | |
| EP1606262A1 (en) | Novel crystalline forms of aripiprazole | |
| WO2002014286A9 (en) | Preparation of risperidone | |
| WO2007109799A2 (en) | Polymorphs of eszopiclone malate | |
| ZA200507100B (en) | Process for preparing a polymorph of rosigitazone maleate | |
| CN114920739A (en) | Crystal form of MRTX849 compound and preparation method and application thereof | |
| US20050143396A1 (en) | Novel crystalline forms of ziprasidone hydrochloride | |
| WO2018113801A1 (en) | Crystalline forms of2-[1-ethylsulfonyl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrile with phosphoric acid and a method of their preparation | |
| WO2004085393A1 (en) | Novel crystalline forms of tegaserod maleate | |
| AU2004312159B2 (en) | Method for preparing phthalocyanines | |
| WO2002012200A1 (en) | Preparation of risperidone | |
| EP1611139A1 (en) | Methods of preparing olanzapine | |
| WO2004092143A1 (en) | A novel crystalline form of risperidone | |
| US20090233932A1 (en) | Novel crystalline forms of lamotrigine | |
| US7393874B2 (en) | Polymorphs of tolterodine tartrate | |
| WO2004083180A1 (en) | Novel crystalline forms of levetiracetam | |
| IE920303A1 (en) | Resolution of trans-2-(2-pyrimidinyl)-7-(hydroxymethyl) octahydro-2H-pyrido[1,2-A]pyrazine | |
| WO2004089952A1 (en) | Novel crystalline forms of abacavir sulfate | |
| US20090227645A1 (en) | Pharmaceutical compositions of valdecoxib | |
| WO2015062562A1 (en) | A stable polymorph of the salt of (2r)-4-oxo-4-[3-(trifiuoromethyl)-5,6- dihydro[l,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl]-l-(2,4,54rifluorophenyl)butan-2-amine with l-tartaric acid | |
| WO2004099183A1 (en) | Novel polymorphs of pantoprazole sodium | |
| WO2004087682A1 (en) | Novel crystalline forms of parecoxib sodium | |
| EP1611138A1 (en) | A novel crystalline form of dorzolamide hydrochloride | |
| WO2004085416A1 (en) | Novel crystalline forms of (s)-citalopram oxalate | |
| WO2002060440A1 (en) | Novel forms of 2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo (1,2-a)pyridine-6-carboxamide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WWE | Wipo information: entry into national phase |
Ref document number: 914/CHENP/2003 Country of ref document: IN |
|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| 122 | Ep: pct application non-entry in european phase | ||
| NENP | Non-entry into the national phase |
Ref country code: JP |
|
| WWW | Wipo information: withdrawn in national office |
Ref document number: JP |