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US20080182988A1 - Aripiprazole crystalline forms - Google Patents

Aripiprazole crystalline forms Download PDF

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Publication number
US20080182988A1
US20080182988A1 US11/869,961 US86996107A US2008182988A1 US 20080182988 A1 US20080182988 A1 US 20080182988A1 US 86996107 A US86996107 A US 86996107A US 2008182988 A1 US2008182988 A1 US 2008182988A1
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Prior art keywords
aripiprazole
solution
ethylenedichloride
methanolate
solvate
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US11/869,961
Inventor
Bandi Parthasaradhi Reddy
Kura Rathnakar Reddy
Rapolu Raji Reddy
Dasari Murallidhara Reddy
Kesireddy Subash Chander Reddy
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Hetero Drugs Ltd
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Hetero Drugs Ltd
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Priority to US11/869,961 priority Critical patent/US20080182988A1/en
Assigned to HETERO DRUGS LIMITED reassignment HETERO DRUGS LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MURALIDHARA REDDY, DASARI, PARTHASARADHI REDDY, BANDI, RAJI REDDY, RAPOLU, RATHNAKAR REDDY, KURA, SUBASH CHANDER REDDY, KESIREDDY
Publication of US20080182988A1 publication Critical patent/US20080182988A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2

Definitions

  • the present invention provides novel crystalline forms of aripiprazole and processes for their preparation.
  • aripiprazole aripiprazole methanolate and aripiprazole ethylene dichloride solvate.
  • the novel crystalline form of aripiprazole is non hygroscopic, do not have the tendency to convert to other forms and suitable for pharmaceutical preparations.
  • the methanolate and ethylene dichloride solvate are non-hygroscopic, obtainable in pure form and can be converted to crystalline forms of aripiprazole and aripiprazole hydrates.
  • the solvates are useful as intermediates for preparing pure aripiprazole or aripiprazole hydrates in any crystalline form.
  • one object of the present invention is to provide stable, non-hygroscopic crystalline form of aripiprazole, process for preparing this form and pharmaceutical compositions containing it.
  • Another object of the present invention is to provide aripiprazole methanolate and aripiprazole ethylenedichloride solvate and process for preparing the solvates; and use of these solvates to prepare other forms of aripiprazole.
  • a novel crystalline form of aripiprazole is designated as aripiprazole form III and typical form III x-ray powder diffraction spectrum of aripiprazole form III is shown in FIG. 1 .
  • Aripiprazole form III is characterized by peaks in the powder x-ray diffraction spectrum having 20 angle positions at about 8.8, 11.2, 11.4, 11.9, 13.6, 14.4, 15.0, 15.9, 16.4, 17.8, 18.7, 20.4, 20.8, 21.4, 22.2, 23.5, 25.0, 25.9 and 26.5 degrees.
  • Aripiprazole used in the process can be in any of the crystalline forms.
  • Aripiprazole solvate or hydrate form can also be used in the process to produce aripiprazole form III.
  • the solution of aripiprazole is usually prepared at elevated temperature, preferably at reflux temperature and then the solution is cooled preferably to 0° C. to 30° C., more preferably to 15° C. to 30° C.
  • the precipitated form III crystals are collected by filtration or centrifugation.
  • aripiprazole methanolate In accordance with the present invention, there is provided aripiprazole methanolate.
  • the content of methanol is between about 2 to 6% of the weight of aripiprazole methanolate.
  • Aripiprazole methanolate typically shows a crystalline form, which is designated as aripiprazole methanolate form IV and typical form IV x-ray powder diffraction spectrum of aripiprazole methanolate form IV is shown in FIG. 2 .
  • Aripiprazole methanolate form IV is characterized by peaks in the powder x-ray diffraction spectrum having 20 angle positions at about 9.8, 11.0, 11.8, 12.1, 12.6, 13.6, 17.4, 18.8, 20.1, 23.3, 24.6, 25.0, 25.9, 27.2, 28.4, 29.3, 30.1 and 31.5 degrees.
  • the solution of aripiprazole is usually prepared at elevated temperature, preferably at reflux temperature and then the solution is cooled preferably to 0° C. to 30° C.
  • the precipitated form IV crystals are collected by filtration or centrifugation.
  • Aripiprazole methanolate can be used to prepare aripiprazole forms by crystallizing from the appropriate solvent system.
  • aripiprazole form III can be prepared by preparing a solution of aripiprazole methanolate in a mixture of methyl tert-butyl ether, acetonitrile and tetrahydrofuran and isolating aripiprazole form III from the solution.
  • aripiprazole ethylenedichloride solvate In accordance with the present invention, there is provided aripiprazole ethylenedichloride solvate.
  • the content of ethylenedichloride is between about 15 to 40% of the weight of aripiprazole ethylenedichloride solvate.
  • Aripiprazole ethylenedichloride solvate typically shows a crystalline form, which is designated as aripiprazole ethylenedichloride solvate form V and the typical form V x-ray powder diffraction spectrum of aripiprazole ethylenedichloride solvate form V is shown in FIG. 3 .
  • Aripiprazole ethylenedichloride solvate form V is characterized by peaks in the powder x-ray diffraction spectrum having 20 angle positions at about 10.7, 17.6, 17.8, 20.6, 22.1, 23.4, 24.7 and 26.4 degrees.
  • the solution of aripiprazole is usually prepared at elevated temperature, preferably at reflux temperature and then the solution is cooled preferably to 0° C. to 30° C.
  • the precipitated form V crystals are collected by filtration or centrifugation.
  • Aripiprazole ethylenedichloride solvate can be used to prepare aripiprazole forms by crystallizing from the appropriate solvent system.
  • aripiprazole form III can be prepared by preparing a solution of aripiprazole ethylenedichloride in a mixture of methyl tert-butyl ether, acetonitrile and tetrahydrofuran and isolating aripiprazole form III from the solution.
  • a pharmaceutical composition comprising aripiprazole form III and a pharmaceutically acceptable carrier or diluent.
  • FIG. 1 is a x-ray powder diffraction spectrum of aripiprazole form III.
  • FIG. 2 is a x-ray powder diffraction spectrum of aripiprazole methanolate form IV.
  • FIG. 3 is a x-ray powder diffraction spectrum of aripiprazole ethylenedichloride solvate form V.
  • x-Ray powder diffraction spectrum was measured on a Bruker axs D8 advance x-ray powder diffractometer having a copper-K ⁇ radiation.
  • Aripiprazole (3 gm) is mixed with methyl tert-butyl ether (25 ml) and heated to reflux temperature. Then acetonitrile (45 ml) and tetrahydrofuran (25 ml) are added to the mixture and heated to about 55° C. to form a clear solution. The solution is slowly cooled to 25° C., stirred for 1 hour at about 25° C. and the precipitated crystals are collected by filtration to give 2 gm of aripiprazole form III.
  • Aripiprazole (3 gm), obtained by a known method is mixed with methanol (30 ml) and heated to reflux temperature. Then tetrahydrofuran (25 ml) is added at the same temperature to form a clear solution. The solution is slowly cooled to about 25° C., stirred for 1 hour at about 25° C. and the separated crystals are collected by filtration to give 2.9 gm of aripiprazole methanolate form IV.
  • Example 1 is repeated using aripiprazole methanolate obtained as in example 2 instead of aripiprazole to give aripiprazole form III.
  • Aripiprazole (3 gm) is mixed with ethylenedichloride (30 ml) and heated to 50° C. to form a clear solution. The solution is slowly cooled to 25° C., stirred for 1 hour at about 25° C. and the separated crystals are collected by filtration to give 2.5 gm of aripiprazole ethylenedichloride solvate form V.
  • Example 1 is repeated using aripiprazole ethylenedichloride solvate obtained as in example 4 instead of aripiprazole to give aripiprazole form III.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention provides novel crystalline forms of aripiprazole and processes for their preparation.

Description

    FIELD OF THE INVENTION
  • The present invention provides novel crystalline forms of aripiprazole and processes for their preparation.
    • BACKGROUND OF THE INVENTION
  • Aripiprazole of formula (I):
  • Figure US20080182988A1-20080731-C00001
  • or 7-[4-[4-(2,3-Dichlorophenyl)-1-piperazinyl]butoxy]-3,4-dihydro-2(1H)-quinolinone and its salts are useful for treating schizophrenia and their therapeutic uses were disclosed in U.S. Pat. No. 5,006,528.
  • Processes for the preparation of aripiprazole and its salts were described in U.S. Pat. No. 5,006,528. Various crystalline forms of aripiprazole and its hydrates were disclosed in WO 03/026659, Japanese Unexamined Patent Publication No. 191256/1990 and 4th Japanese-Korean Symposium on Separation Technology (Oct. 6-8, 1996).
  • We have discovered a novel crystalline form of aripiprazole, aripiprazole methanolate and aripiprazole ethylene dichloride solvate. The novel crystalline form of aripiprazole is non hygroscopic, do not have the tendency to convert to other forms and suitable for pharmaceutical preparations.
  • The methanolate and ethylene dichloride solvate are non-hygroscopic, obtainable in pure form and can be converted to crystalline forms of aripiprazole and aripiprazole hydrates.
  • Therefore, the solvates are useful as intermediates for preparing pure aripiprazole or aripiprazole hydrates in any crystalline form.
  • Thus, one object of the present invention is to provide stable, non-hygroscopic crystalline form of aripiprazole, process for preparing this form and pharmaceutical compositions containing it.
  • Another object of the present invention is to provide aripiprazole methanolate and aripiprazole ethylenedichloride solvate and process for preparing the solvates; and use of these solvates to prepare other forms of aripiprazole.
    • DESCRIPTION OF THE INVENTION
  • In accordance with the present invention, there is provided a novel crystalline form of aripiprazole. The crystalline form is designated as aripiprazole form III and typical form III x-ray powder diffraction spectrum of aripiprazole form III is shown in FIG. 1.
  • Aripiprazole form III is characterized by peaks in the powder x-ray diffraction spectrum having 20 angle positions at about 8.8, 11.2, 11.4, 11.9, 13.6, 14.4, 15.0, 15.9, 16.4, 17.8, 18.7, 20.4, 20.8, 21.4, 22.2, 23.5, 25.0, 25.9 and 26.5 degrees.
  • In accordance with the present invention, there is provided a process for preparation of the aripiprazole form III comprising the steps of:
    • a) preparing a solution of aripiprazole in a mixture of methyl tert-butyl ether, acetonitrile and tetrahydrofuran; and
    • b) isolating aripiprazole form III from the solution.
  • Aripiprazole used in the process can be in any of the crystalline forms. Aripiprazole solvate or hydrate form can also be used in the process to produce aripiprazole form III.
  • The solution of aripiprazole is usually prepared at elevated temperature, preferably at reflux temperature and then the solution is cooled preferably to 0° C. to 30° C., more preferably to 15° C. to 30° C. The precipitated form III crystals are collected by filtration or centrifugation.
  • In accordance with the present invention, there is provided aripiprazole methanolate. The content of methanol is between about 2 to 6% of the weight of aripiprazole methanolate. Aripiprazole methanolate typically shows a crystalline form, which is designated as aripiprazole methanolate form IV and typical form IV x-ray powder diffraction spectrum of aripiprazole methanolate form IV is shown in FIG. 2.
  • Aripiprazole methanolate form IV is characterized by peaks in the powder x-ray diffraction spectrum having 20 angle positions at about 9.8, 11.0, 11.8, 12.1, 12.6, 13.6, 17.4, 18.8, 20.1, 23.3, 24.6, 25.0, 25.9, 27.2, 28.4, 29.3, 30.1 and 31.5 degrees.
  • In accordance with the present invention, there is provided a process for preparation of the aripiprazole methanolate form IV comprising the steps of:
    • a) preparing a solution of aripiprazole in a mixture of methanol and tetrahydrofuran; and
    • b) isolating aripiprazole methanolate form IV from the solution.
  • The solution of aripiprazole is usually prepared at elevated temperature, preferably at reflux temperature and then the solution is cooled preferably to 0° C. to 30° C. The precipitated form IV crystals are collected by filtration or centrifugation.
  • Aripiprazole methanolate can be used to prepare aripiprazole forms by crystallizing from the appropriate solvent system. Thus, for example aripiprazole form III can be prepared by preparing a solution of aripiprazole methanolate in a mixture of methyl tert-butyl ether, acetonitrile and tetrahydrofuran and isolating aripiprazole form III from the solution.
  • In accordance with the present invention, there is provided aripiprazole ethylenedichloride solvate. The content of ethylenedichloride is between about 15 to 40% of the weight of aripiprazole ethylenedichloride solvate. Aripiprazole ethylenedichloride solvate typically shows a crystalline form, which is designated as aripiprazole ethylenedichloride solvate form V and the typical form V x-ray powder diffraction spectrum of aripiprazole ethylenedichloride solvate form V is shown in FIG. 3.
  • Aripiprazole ethylenedichloride solvate form V is characterized by peaks in the powder x-ray diffraction spectrum having 20 angle positions at about 10.7, 17.6, 17.8, 20.6, 22.1, 23.4, 24.7 and 26.4 degrees.
  • In accordance with the present invention, there is provided a process for preparation of the Aripiprazole ethylenedichloride solvate form V comprising the steps of:
    • a) preparing a solution of aripiprazole in ethylenedichloride and
    • b) isolating aripiprazole ethylenedichloride solvate form V from the solution.
  • The solution of aripiprazole is usually prepared at elevated temperature, preferably at reflux temperature and then the solution is cooled preferably to 0° C. to 30° C. The precipitated form V crystals are collected by filtration or centrifugation.
  • Aripiprazole ethylenedichloride solvate can be used to prepare aripiprazole forms by crystallizing from the appropriate solvent system. Thus, for example aripiprazole form III can be prepared by preparing a solution of aripiprazole ethylenedichloride in a mixture of methyl tert-butyl ether, acetonitrile and tetrahydrofuran and isolating aripiprazole form III from the solution.
  • In accordance with the present invention, there is provided a pharmaceutical composition comprising aripiprazole form III and a pharmaceutically acceptable carrier or diluent.
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 is a x-ray powder diffraction spectrum of aripiprazole form III.
  • FIG. 2 is a x-ray powder diffraction spectrum of aripiprazole methanolate form IV.
  • FIG. 3 is a x-ray powder diffraction spectrum of aripiprazole ethylenedichloride solvate form V.
    •
  • x-Ray powder diffraction spectrum was measured on a Bruker axs D8 advance x-ray powder diffractometer having a copper-Kα radiation.
  • The invention will now be further described by the following examples, which are illustrative rather than limiting.
    • EXAMPLE 1
  • Aripiprazole (3 gm) is mixed with methyl tert-butyl ether (25 ml) and heated to reflux temperature. Then acetonitrile (45 ml) and tetrahydrofuran (25 ml) are added to the mixture and heated to about 55° C. to form a clear solution. The solution is slowly cooled to 25° C., stirred for 1 hour at about 25° C. and the precipitated crystals are collected by filtration to give 2 gm of aripiprazole form III.
    • EXAMPLE 2
  • Aripiprazole (3 gm), obtained by a known method is mixed with methanol (30 ml) and heated to reflux temperature. Then tetrahydrofuran (25 ml) is added at the same temperature to form a clear solution. The solution is slowly cooled to about 25° C., stirred for 1 hour at about 25° C. and the separated crystals are collected by filtration to give 2.9 gm of aripiprazole methanolate form IV.
    • EXAMPLE 3
  • Example 1 is repeated using aripiprazole methanolate obtained as in example 2 instead of aripiprazole to give aripiprazole form III.
    • EXAMPLE 4
  • Aripiprazole (3 gm) is mixed with ethylenedichloride (30 ml) and heated to 50° C. to form a clear solution. The solution is slowly cooled to 25° C., stirred for 1 hour at about 25° C. and the separated crystals are collected by filtration to give 2.5 gm of aripiprazole ethylenedichloride solvate form V.
    • EXAMPLE 5
  • Example 1 is repeated using aripiprazole ethylenedichloride solvate obtained as in example 4 instead of aripiprazole to give aripiprazole form III.

Claims (6)

1-5. (canceled)
6. A crystalline aripiprazole methanolate form IV, characterized by an x-ray powder diffraction spectrum having peaks expressed as 20 at about 9.8, 11.0, 11.8, 12.1, 12.6, 13.6, 17.4, 18.8, 20.1, 23.3, 24.6, 25.0, 25.9, 27.2, 28.4, 29.3, 30.1 and 31.5 degrees.
7. A crystalline aripiprazole methanolate form IV as defined in claim 6, further characterized by an x-ray powder diffraction spectrum as in FIG. 2.
8. (canceled)
9. A process according to claim 8, wherein the product obtained is aripiprazole methanolate.
10-18. (canceled)
US11/869,961 2003-07-25 2007-10-10 Aripiprazole crystalline forms Abandoned US20080182988A1 (en)

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JP5546717B2 (en) * 2003-12-16 2014-07-09 テバ ファーマシューティカル インダストリーズ リミティド Method for preparing aripiprazole crystalline form
US7714129B2 (en) * 2003-12-16 2010-05-11 Teva Pharmaceutical Industries Ltd. Methods of preparing anhydrous aripiprazole form II
MXPA06008828A (en) * 2004-02-05 2007-04-25 Teva Pharma Process for preparing aripiprazole.
EP1765782A1 (en) 2004-02-05 2007-03-28 Teva Pharmaceutical Industries Ltd Method of making 7-(4-bromobutoxy)-3,4-dihydrocarbostyril
WO2006053780A1 (en) * 2004-11-18 2006-05-26 Synthon B.V. Crystalline aripiprazole solvates
EP1686117A1 (en) * 2005-01-27 2006-08-02 Sandoz AG Polymorph and solvates of aripiprazole
WO2006079549A1 (en) * 2005-01-27 2006-08-03 Sandoz Ag Salts of aripiprazole
EP1858855B2 (en) † 2005-03-17 2021-03-03 Synthon B.V. Process of making crystalline type ii aripiprazole
CA2605128A1 (en) * 2005-04-15 2007-01-11 Medichem, S.A. Syntheses and preparations of polymorphs of crystalline aripiprazole
JP2008537540A (en) * 2005-12-22 2008-09-18 テバ ファーマシューティカル インダストリーズ リミティド A method for reducing the particle size of aripiprazole
WO2007092779A2 (en) * 2006-02-03 2007-08-16 Dr. Reddy's Laboratories Ltd. Aripiprazole co-crystals
US7799790B2 (en) 2006-07-20 2010-09-21 Helm Ag Amorphous aripiprazole and process for the preparation thereof
EP1880714A1 (en) 2006-07-20 2008-01-23 Helm AG Amorphous Aripiprazole and Process for the Preparation thereof
GB0707761D0 (en) 2007-04-21 2007-05-30 Finlay Hydrascreens Ltd Crushing machines
ES2353444T3 (en) 2008-01-23 2011-03-02 Helm Ag ARIPIPRAZOL AMORFO AND PROCEDURE FOR PREPARATION.
WO2015067313A1 (en) 2013-11-07 2015-05-14 Synthon B.V. Orodispersible pharmaceutical compositions comprising aripiprazole
CN106474058B (en) 2015-08-31 2020-01-07 南京诺瑞特医药科技有限公司 Aripiprazole injectable suspension formulation with extended shelf life

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