USRE45573E1 - Process for producing imide compound - Google Patents

Process for producing imide compound Download PDF

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Publication number
USRE45573E1
USRE45573E1 US14/137,464 US200414137464A USRE45573E US RE45573 E1 USRE45573 E1 US RE45573E1 US 200414137464 A US200414137464 A US 200414137464A US RE45573 E USRE45573 E US RE45573E
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Prior art keywords
hydrochloric acid
aqueous hydrochloric
hydrochloride
acid solution
imide compound
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US14/137,464
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English (en)
Inventor
Yuzo Kakiya
Mayumi Oda
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Sumitomo Pharma Co Ltd
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Sumitomo Dainippon Pharma Co Ltd
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Application filed by Sumitomo Dainippon Pharma Co Ltd filed Critical Sumitomo Dainippon Pharma Co Ltd
Priority to US14/137,464 priority Critical patent/USRE45573E1/en
Assigned to SUMITOMO DAINIPPON PHARMA CO., LTD. reassignment SUMITOMO DAINIPPON PHARMA CO., LTD. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: DAINIPPON SUMITOMO PHARMA CO., LTD.
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Assigned to Sumitomo Pharma Co., Ltd. reassignment Sumitomo Pharma Co., Ltd. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: SUMITOMO DAINIPPON PHARMA CO., LTD.
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a process for producing an imide compound of the formula (2) or an enantiomer thereof, which is useful as a psychotropic substance.
  • the imide compound hydrochloride of the above formula (2) can be produced by treating an imide compound in free form of the formula (1):
  • An object of the present invention is to provide an excellent industrial process for producing the above imide compound hydrochloride.
  • the present inventors have intensively studied in order to solve the above-mentioned problems, and found that the imide compound hydrochloride of the above formula (2) can be obtained in high quality and high yield under moderate and simple reaction conditions by treating the compound of the above formula (1) with an aqueous hydrochloric acid solution in a hydrophilic solvent, and crystallizing the resultant, and they have accomplished the present invention.
  • the present invention relates to the following:
  • the imide compound hydrochloride of the above formula (2) or an enantiomer thereof (hereinafter, occasionally simply referred to as the imide compound hydrochloride of the formula (2) or the imide compound hydrochloride (2)) can be produced by treating a solution of the compound of the above formula (1) or an enantiomer thereof (hereinafter, occasionally simply referred to as the compound of the formula (1) or the compound (1)) in a hydrophilic solvent with an aqueous hydrochloric acid solution, and crystallizing the resultant.
  • the compound of the formula (1) can be produced according to the method disclosed in JP-A-5-17440.
  • the hydrophilic solvent includes, for example, ketone solvents, ether solvents, and alcohol solvents, and preferable ones are ketone solvents.
  • the ketone solvent includes, for example, dialkyl ketones having not more than 6 carbon atoms such as acetone, methyl ethyl ketone, 4-methyl-2-pentanone, etc. Preferable ones are acetone, methyl ethyl ketone, and most preferable one is acetone.
  • the ether solvent includes, for example, cyclic ethers having not more than 6 carbon atoms such as tetrahydrofuran, dioxane, etc., and acyclic dialkyl ethers having not more than 6 carbon atoms such as dimethyl ether, diethyl ether, etc. Preferable one is tetrahydrofuran.
  • the alcohol solvent includes, for example, alcohols having not more than 6 carbon atoms such as 2-propanol, ethanol, methanol, ethylene glycol, etc., and preferable one is 2-propanol.
  • the hydrophilic solvent is usually used in an amount of 3 to 100 times (by weight) of the amount of the compound (1), preferably in an amount of 5 to 30 times (by weight) of the amount of the compound (1), and more preferably in an amount of 7 to 15 times (by weight) of the amount of the compound (1).
  • the temperature for dissolving the compound (1) in a hydrophilic solvent is usually in the range of 0° C. to a reflux temperature, preferably in the range of 25° C. to a reflux temperature.
  • the temperature is more preferably in the range of 45° C. to a reflux temperature.
  • the concentration of hydrogen chloride in the aqueous hydrochloric acid solution is not necessarily specified.
  • an aqueous hydrochloric acid solution in a concentration of 0.3-36% may be exemplified.
  • the concentration of hydrogen chloride in the aqueous hydrochloric acid solution is preferably a 1.8 to 14.4% aqueous hydrochloric acid solution, more preferably about 3.0 to 5.0% aqueous hydrochloric acid solution, from view point of (i) the amount of the hydrophilic solvent contained in the crystals of the imide compound hydrochloride, (ii) the amount of the impurities contained in the crystals of the imide compound hydrochloride, and (iii) the yield (see Table 1).
  • the equivalents of the hydrochloric acid to be used is usually in the range of 0.9 to 3 equivalents, preferably in the range of 1.0 to 2.0 equivalents, more preferably in the range of 1.0 to 1.3 equivalent, to one equivalent of the compound (1).
  • the temperature for treating the compound (1) with an aqueous hydrochloric acid solution in a hydrophilic solvent and crystallizing the resultant is not necessarily specified, and these processes may be carried out either under cooling or warming.
  • the reaction temperature is usually in the range of 0° C. to a reflux temperature, preferably in the range of 25° C. to a reflux temperature, and more preferably in the range of 50° C. to a reflux temperature.
  • the method for mixing a solution of the compound (1) in a hydrophilic solvent and an aqueous hydrochloric acid solution is not necessarily specified.
  • a method of adding an aqueous hydrochloric acid solution into a solution of the compound (1) in a hydrophilic solvent, a method of adding a solution of the compound (1) in a hydrophilic solvent into an aqueous hydrochloric acid solution, a method of simultaneously adding both a solution of the compound (1) in a hydrophilic solvent and an aqueous hydrochloric acid solution into the reactor vessel, a method of adding a mixture of an aqueous hydrochloric acid solution and a hydrophilic solvent into a solution of the compound (1) in a hydrophilic solvent, a method of adding a solution of the compound (1) in a hydrophilic solvent into a mixture of an aqueous hydrochloric acid solution and a hydrophilic solvent, etc. are exemplified.
  • the time to be needed for mixing a solution of the compound (1) in a hydrophilic solvent and an aqueous hydrochloric acid solution is not necessarily specified.
  • a method of mixing both solutions at once a method of mixing by adding one of them into the other with spending an extended period of time, are exemplified.
  • a method of mixing by adding one of them into the other with spending an extended period of time is usually employed.
  • the time to be needed is, for example, in the range of from one minute to 6 hours, preferably in the range of from 3 minutes to 3 hours.
  • the crystals of the imide compound hydrochloride precipitated by treatment with hydrochloric acid are separated by a conventional method, for example, by filtration, to give the imide compound hydrochloride of the above formula (2).
  • the temperature of the reaction slurry prior to the filtration is not necessarily specified, and the filtration is usually carried out after the reaction slurry is sufficiently crystallized by cooling or warming.
  • the temperature for keeping the reaction slurry is usually in the range of ⁇ 20° C. to 60° C., preferably in the range of ⁇ 10° C. to 25° C., more preferably in the range of 0 to 10° C.
  • the imide compound hydrochloride (2) thus separated may be obtained in the solvent-free form by drying.
  • the drying method is not necessarily specified, for example, drying under reduced pressure, drying under atmospheric pressure, drying with aeration of inert gas such as nitrogen or air flow.
  • the drying temperature is not necessarily specified, and the drying is carried either under cooling or warming, preferably at a temperature of 0 to 50° C.
  • the imide compound hydrochloride represented by the above formula (2) has been known to be useful as an agent for treatment of schizophrenia, etc. (cf., JP-A-5-17440).
  • the amounts of acetone in the crystals were determined by gas chromatography using a capillary column and FID detector, and the amounts of impurities were determined by liquid chromatography using a reversed phase ODS column and a UV detector.
US14/137,464 2003-07-29 2004-07-27 Process for producing imide compound Active 2025-07-18 USRE45573E1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US14/137,464 USRE45573E1 (en) 2003-07-29 2004-07-27 Process for producing imide compound

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2003281860 2003-07-29
JP2003-281860 2003-07-29
PCT/JP2004/011035 WO2005009999A1 (ja) 2003-07-29 2004-07-27 イミド化合物の製造方法
US14/137,464 USRE45573E1 (en) 2003-07-29 2004-07-27 Process for producing imide compound
US10/565,105 US7605260B2 (en) 2003-07-29 2004-07-27 Process for producing imide compound

Publications (1)

Publication Number Publication Date
USRE45573E1 true USRE45573E1 (en) 2015-06-23

Family

ID=34100970

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US10/565,105 Active 2025-07-18 US7605260B2 (en) 2003-07-29 2004-07-27 Process for producing imide compound
US14/137,464 Active 2025-07-18 USRE45573E1 (en) 2003-07-29 2004-07-27 Process for producing imide compound

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US10/565,105 Active 2025-07-18 US7605260B2 (en) 2003-07-29 2004-07-27 Process for producing imide compound

Country Status (12)

Country Link
US (2) US7605260B2 (da)
EP (1) EP1652848B1 (da)
JP (1) JP4610485B2 (da)
KR (1) KR101085806B1 (da)
CN (1) CN100422178C (da)
AT (1) ATE543817T1 (da)
AU (1) AU2004259305B2 (da)
BR (1) BRPI0413081B8 (da)
CA (1) CA2538265C (da)
DK (1) DK1652848T3 (da)
ES (1) ES2378990T3 (da)
WO (1) WO2005009999A1 (da)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4866349B2 (ja) * 2005-06-13 2012-02-01 大日本住友製薬株式会社 可溶化型製剤
DK2144905T3 (da) 2007-04-04 2013-03-11 Merck Sharp & Dohme Terapeutiske midler
WO2011093522A1 (en) * 2010-01-28 2011-08-04 Dainippon Sumitomo Pharma Co., Ltd. A cycloalkane derivative
DK2563790T3 (da) 2010-04-26 2016-10-24 Sumitomo Dainippon Pharma Co Ltd Proces til et kvaternært ammoniumsalt
WO2012053654A1 (en) * 2010-10-18 2012-04-26 Dainippon Sumitomo Pharma Co., Ltd. Sustained-release formulation for injection
WO2012107890A2 (en) 2011-02-10 2012-08-16 Ranbaxy Laboratories Limited Crystalline forms of lurasidone hydrochloride
WO2012123858A1 (en) 2011-03-14 2012-09-20 Ranbaxy Laboratories Limited Amorphous lurasidone hydrochloride
EP2736905A4 (en) 2011-07-28 2015-07-29 Mapi Pharma Ltd INTERMEDIATE COMPOUNDS AND PROCESS FOR THE PREPARATION OF LURASIDONE AND SALTS THEREOF
CZ304027B6 (cs) * 2011-08-18 2013-08-28 Farmak, A. S. Zpusob prípravy polymorfu (1R,2S,3R,4S)-N-[(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinylmethyl]-1-cyklohexylmethyl]-2,3-bicyklo[2.2.1]heptandikarboximidu hydrochloridu
CN102952064A (zh) * 2011-08-19 2013-03-06 天津药物研究院 一种医药中间体顺式-外-二环[2.2.1]庚烷-2.3-二甲酰亚胺的制备方法
WO2013030722A1 (en) 2011-08-26 2013-03-07 Ranbaxy Laboratories Limited Crystalline lurasidone hydrochloride
CN103130795A (zh) * 2011-12-02 2013-06-05 苏州二叶制药有限公司 卢拉西酮盐酸盐的晶体a及其用途
CN103130794B (zh) * 2011-12-02 2016-06-22 苏州二叶制药有限公司 卢拉西酮盐酸盐的晶体a的制备方法
US9409899B2 (en) 2012-02-13 2016-08-09 Cadila Healthcare Limited Process for preparing benzisothiazol-3-yl-piperazin-1-yl-methyl-cyclo hexylmethanisoindol-1,3-dione and its intermediates
CN103360383B (zh) * 2012-04-11 2016-07-06 上海医药工业研究院 鲁拉西酮盐酸盐的晶型b及其制备方法
CN102746289B (zh) * 2012-04-28 2016-06-08 上海医药工业研究院 一种盐酸卢拉西酮的制备方法
WO2013190455A2 (en) * 2012-06-18 2013-12-27 Shasun Pharmaceuticals Limited Process for the preparation of lurasidone hydrochloride
CN102863437A (zh) * 2012-09-04 2013-01-09 济南百诺医药科技开发有限公司 一种鲁拉西酮的制备方法
WO2014064714A2 (en) * 2012-10-22 2014-05-01 Glenmark Pharmaceuticals Limited; Glenmark Generics Limited Process for preparation of lurasidone hydrochloride
CN102911170A (zh) * 2012-11-15 2013-02-06 苏州第壹制药有限公司 酰亚胺化合物盐酸盐的制备方法
CN104031041A (zh) * 2013-03-06 2014-09-10 江苏恩华药业股份有限公司 盐酸鲁拉西酮的新晶型及其制备方法
CN103539794A (zh) * 2013-10-17 2014-01-29 常州大学 一种盐酸鲁拉西酮的成盐方法
CZ306203B6 (cs) 2013-12-06 2016-09-29 Zentiva, K. S Způsob syntézy lurasidonu
WO2015195478A1 (en) 2014-06-16 2015-12-23 Johnson Matthey Public Limited Company Processes for making alkylated arylpiperazine and alkylated arylpiperidine compounds including novel intermediates
EP3207041B1 (en) * 2014-10-14 2019-12-04 Jubilant Generics Limited (Formerly Jubilant Life Sciences Division) An improved process for the preparation of lurasidone hydrochloride
EP3760205A4 (en) 2018-02-28 2021-10-27 Sumitomo Dainippon Pharma Co., Ltd. AQUATIC SUSPENSION TYPE PHARMACEUTICAL PREPARATION
WO2019167978A1 (ja) 2018-02-28 2019-09-06 大日本住友製薬株式会社 溶出が制御された水性懸濁型医薬製剤
CN115950695B (zh) * 2021-10-09 2023-07-28 北京阳光诺和药物研究股份有限公司 一种制备鲁拉西酮基毒杂质的方法

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US4479954A (en) 1981-05-29 1984-10-30 Eisai Co., Ltd. Piperazine substituted carboxamide derivatives, compositions and method of use
US4978752A (en) 1987-12-04 1990-12-18 Takeda Chemical Industries, Ltd. Crystals of cephem hydrochloride
JPH0517440A (ja) 1990-07-06 1993-01-26 Sumitomo Pharmaceut Co Ltd 新規なイミド誘導体
WO1996033185A1 (en) 1995-04-21 1996-10-24 Hexal Pharmaceuticals, Inc. A process for preparing form 1 ranitidine hydrochloride
WO2001058835A1 (en) 2000-02-11 2001-08-16 Degussa Ag Resolution of dl-racemic mixtures
WO2002053140A2 (en) * 2001-01-02 2002-07-11 Pharmacia & Upjohn Company New drug combinations of norepinehrine reuptake inhibitors and neuroleptic agents

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JPS517440A (da) * 1974-07-08 1976-01-21 Japan Storage Battery Co Ltd
WO2001076557A1 (fr) * 2000-04-10 2001-10-18 Sumitomo Pharmaceuticals Co., Ltd. Preparations a liberation prolongee

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4479954A (en) 1981-05-29 1984-10-30 Eisai Co., Ltd. Piperazine substituted carboxamide derivatives, compositions and method of use
US4978752A (en) 1987-12-04 1990-12-18 Takeda Chemical Industries, Ltd. Crystals of cephem hydrochloride
CN1020611C (zh) 1987-12-04 1993-05-12 武田药品工业株式会社 头孢烯盐酸盐的制备方法
US5780632A (en) 1990-06-07 1998-07-14 Sumitomo Pharmaceuticals Company, Limited Imide derivatives and their production and use
JPH0517440A (ja) 1990-07-06 1993-01-26 Sumitomo Pharmaceut Co Ltd 新規なイミド誘導体
US5532372A (en) 1990-07-06 1996-07-02 Sumitomo Pharmaceuticals Company, Ltd. Imide derivatives, and their production and use
WO1996033185A1 (en) 1995-04-21 1996-10-24 Hexal Pharmaceuticals, Inc. A process for preparing form 1 ranitidine hydrochloride
US5663381A (en) 1995-04-21 1997-09-02 Hexal Pharmaceuticals, Inc. Process for preparing form 1 ranitidine hydrochloride
WO2001058835A1 (en) 2000-02-11 2001-08-16 Degussa Ag Resolution of dl-racemic mixtures
US6673942B1 (en) 2000-02-11 2004-01-06 Degussa Ag Resolution of DL-racemic mixtures
WO2002053140A2 (en) * 2001-01-02 2002-07-11 Pharmacia & Upjohn Company New drug combinations of norepinehrine reuptake inhibitors and neuroleptic agents

Also Published As

Publication number Publication date
EP1652848A4 (en) 2009-04-15
BRPI0413081B1 (pt) 2018-03-20
CN1832946A (zh) 2006-09-13
CN100422178C (zh) 2008-10-01
US7605260B2 (en) 2009-10-20
KR20060052840A (ko) 2006-05-19
AU2004259305A1 (en) 2005-02-03
EP1652848A1 (en) 2006-05-03
US20060194970A1 (en) 2006-08-31
CA2538265C (en) 2012-10-02
CA2538265A1 (en) 2005-02-03
AU2004259305B2 (en) 2009-06-04
BRPI0413081B8 (pt) 2021-05-25
BRPI0413081A (pt) 2006-10-03
JP4610485B2 (ja) 2011-01-12
EP1652848B1 (en) 2012-02-01
ATE543817T1 (de) 2012-02-15
JPWO2005009999A1 (ja) 2006-09-07
DK1652848T3 (da) 2012-02-27
ES2378990T3 (es) 2012-04-19
KR101085806B1 (ko) 2011-11-22
WO2005009999A1 (ja) 2005-02-03

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