WO2020237643A1 - Procédé de préparation d'une forme cristalline alpha de silodosine - Google Patents

Procédé de préparation d'une forme cristalline alpha de silodosine Download PDF

Info

Publication number
WO2020237643A1
WO2020237643A1 PCT/CN2019/089584 CN2019089584W WO2020237643A1 WO 2020237643 A1 WO2020237643 A1 WO 2020237643A1 CN 2019089584 W CN2019089584 W CN 2019089584W WO 2020237643 A1 WO2020237643 A1 WO 2020237643A1
Authority
WO
WIPO (PCT)
Prior art keywords
solvent
xerodoxine
crystal form
preparing
ether
Prior art date
Application number
PCT/CN2019/089584
Other languages
English (en)
Chinese (zh)
Inventor
李文华
王松
西亮
魏帅
Original Assignee
上海汇伦生命科技有限公司
上海汇伦医药科技有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 上海汇伦生命科技有限公司, 上海汇伦医药科技有限公司 filed Critical 上海汇伦生命科技有限公司
Priority to PCT/CN2019/089584 priority Critical patent/WO2020237643A1/fr
Publication of WO2020237643A1 publication Critical patent/WO2020237643A1/fr

Links

Images

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D9/00—Crystallisation
    • B01D9/02—Crystallisation from solutions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Definitions

  • the invention belongs to the field of medicinal chemistry, and specifically relates to a method for preparing xerodoxine ⁇ -crystal form.
  • Silodosin also known as silodosin, is an ⁇ 1 -adrenergic receptor antagonist developed by Tachibana Pharmaceutical Co., Ltd., which can be used to treat dysuria.
  • Xelodosin 1-(3-hydroxypropyl)-5-[(2R)-2-( ⁇ 2-[2-(2,2,2-trifluoroethoxy)phenoxy ]Ethyl ⁇ amino)propyl]-2,3-dihydro-1H-indole-7-carboxamide, its structural formula is as follows:
  • the purpose of the present invention is to solve the problem that the solvent residue is likely to exceed the standard during the preparation process of the ⁇ -crystalline form of xerodoxine, thereby providing a new method for preparing the ⁇ -crystalline form of xerodoxine.
  • the preparation method dissolves xerodoxine in a solvent and then cools and crystallizes.
  • the solvent includes a good solvent and a poor solvent.
  • the method has simple operation, high product yield, high purity, low solvent residue, and has high application and market promotion prospects.
  • the present invention provides a method for preparing xerodoxine ⁇ -crystal form as shown in formula I, and the method includes the following steps:
  • the solvent includes a good solvent and a poor solvent
  • the good solvent includes a ketone solvent
  • the poor solvent includes an ether solvent and/or an alkane solvent.
  • the ketone solvent is preferably one or more of methyl ethyl ketone, acetone, cyclohexanone, methyl methyl ethyl ketone and methyl isobutyl ketone, and more preferably methyl ethyl ketone, acetone, cyclohexanone And one or more of methyl isobutyl ketone.
  • the ketone solvent of the present invention is a mixed form of multiple ketone substances, the volume ratio of the various ketone substances is not particularly limited, as long as the experimental purpose can be achieved, for example, it can be mixed in equal volume.
  • the ether solvent is preferably one or more of diethyl ether, dipropyl ether, butyl ether, isopropyl ether and methyl tert-butyl ether, more preferably methyl tert-butyl ether And/or isopropyl ether. If the ether solvent of the present invention is a mixed form of multiple ether substances, the volume ratio of the various ether substances is not particularly limited, as long as the experimental purpose can be achieved.
  • the alkane solvent is a C 4 -C 10 alkane solvent, preferably a C 5 -C 8 alkane solvent, more preferably n-hexane, cyclohexane, n-heptane and n-octane One or more of, more preferably n-hexane and/or n-heptane. If the alkane solvent of the present invention is a mixed form of multiple alkane substances, the volume ratio of the various alkane substances is not particularly limited, as long as it can achieve the experimental purpose.
  • the volume ratio of the good solvent to the poor solvent is 1:1-8, preferably the volume ratio is 1:2-6, and more preferably 1:3-6.
  • the mass-volume ratio between the xerodoxine and the good solvent is preferably 1:1-10 g/ml, more preferably 1:1-5 g/ml.
  • the mass-volume ratio of the xerodoxine to the poor solvent is 1:1-20 g/ml, preferably 1:5-15 g/ml.
  • the method for dissolving xerodoxine in a solvent may be a conventional dissolution method in the art, such as heating to dissolve, and the heating temperature may be 30-80°C, more preferably 40-70°C .
  • the cooling method in the present invention may be a conventional cooling method in the art, and the cooling temperature is 20°C or less, preferably 10°C, and more preferably 5°C or less.
  • the present invention when preparing the ⁇ -crystal form of xerodoxine, it is optional to add or not add seed crystals of the ⁇ -crystal form and ⁇ -crystal form to induce crystallization.
  • the method for preparing the ⁇ -crystal form of xerodoxine of the present invention may further include the operations of filtration and drying after crystallization.
  • the filtration can be a conventional filtration operation in the field, such as vacuum filtration.
  • the drying may be a conventional drying operation in the art, such as vacuum drying, etc., and the drying temperature is preferably 20-80°C, more preferably 40-70°C.
  • room temperature can be defined as a conventional room temperature in the art, unless otherwise specified, it generally refers to an ambient temperature of 25°C.
  • the preparation method of the ⁇ -crystal form of xerodoxine of the present invention uses a good solvent and a poor solvent as the crystallization solvent.
  • the method is simple to operate, the product obtained has high yield, high purity, less solvent residue, and can significantly reduce drying time , Has a high application and market promotion prospects.
  • Fig. 1 is an X-ray diffraction pattern of ⁇ -crystal form xerodosin prepared in Example 1.
  • the obtained crystals were subjected to X-ray diffraction pattern measurement.
  • the characteristic peaks are shown in Figure 1.
  • the main peak 2 ⁇ angles are 5.380, 5.920, 9.678, 10.940, 12.040, 16.260, 19.500, 19.779, which are similar to the ⁇ -crystal form reported in the literature.
  • the X-ray diffraction pattern data of lodoxine are consistent.
  • Example 10 ⁇ seed crystals were added for induction.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention concerne un procédé de préparation d'une forme cristalline alpha de silodosine. Le procédé comprend les étapes suivantes : dissolution de silodosine dans un solvant, puis refroidissement et cristallisation de celle-ci. Le solvant comprend un bon solvant et un solvant médiocre. Le bon solvant comprend un solvant à base de cétone, et le solvant médiocre comprend un solvant à base d'éther et/ou un solvant à base d'alcane. Le procédé de préparation selon la présente invention a un mode opératoire simple, un rendement élevé du produit obtenu et un faible solvant résiduel, et peut réduire de manière significative le temps de séchage.
PCT/CN2019/089584 2019-05-31 2019-05-31 Procédé de préparation d'une forme cristalline alpha de silodosine WO2020237643A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/CN2019/089584 WO2020237643A1 (fr) 2019-05-31 2019-05-31 Procédé de préparation d'une forme cristalline alpha de silodosine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2019/089584 WO2020237643A1 (fr) 2019-05-31 2019-05-31 Procédé de préparation d'une forme cristalline alpha de silodosine

Publications (1)

Publication Number Publication Date
WO2020237643A1 true WO2020237643A1 (fr) 2020-12-03

Family

ID=73551961

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2019/089584 WO2020237643A1 (fr) 2019-05-31 2019-05-31 Procédé de préparation d'une forme cristalline alpha de silodosine

Country Status (1)

Country Link
WO (1) WO2020237643A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1694867A (zh) * 2002-09-06 2005-11-09 橘生药品工业株式会社 口服固体药用晶体及治疗排尿困难的包含它的口服固体药
CN102010359A (zh) * 2010-09-10 2011-04-13 北京阳光诺和药物研究有限公司 β晶型西洛多辛的制备方法
WO2012077138A1 (fr) * 2010-12-09 2012-06-14 Panacea Biotec Limited Procédés de cristallisation du (r)-1-(3-hydroxypropyl)-5-[2-[2-(2,2,2- trifluoroéthoxy)phénoxy]éthylamino]propyl]indoline-7-carboxamide
CN103360298A (zh) * 2012-04-06 2013-10-23 昆明积大制药股份有限公司 一种β型西洛多辛晶体的制备方法
WO2015093456A1 (fr) * 2013-12-17 2015-06-25 東和薬品株式会社 Cristal de silodosine de forme γ et son procédé de production
JP2018080125A (ja) * 2016-11-15 2018-05-24 宇部興産株式会社 インドリン化合物のβ型結晶の製造方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1694867A (zh) * 2002-09-06 2005-11-09 橘生药品工业株式会社 口服固体药用晶体及治疗排尿困难的包含它的口服固体药
CN102010359A (zh) * 2010-09-10 2011-04-13 北京阳光诺和药物研究有限公司 β晶型西洛多辛的制备方法
WO2012077138A1 (fr) * 2010-12-09 2012-06-14 Panacea Biotec Limited Procédés de cristallisation du (r)-1-(3-hydroxypropyl)-5-[2-[2-(2,2,2- trifluoroéthoxy)phénoxy]éthylamino]propyl]indoline-7-carboxamide
CN103360298A (zh) * 2012-04-06 2013-10-23 昆明积大制药股份有限公司 一种β型西洛多辛晶体的制备方法
WO2015093456A1 (fr) * 2013-12-17 2015-06-25 東和薬品株式会社 Cristal de silodosine de forme γ et son procédé de production
JP2018080125A (ja) * 2016-11-15 2018-05-24 宇部興産株式会社 インドリン化合物のβ型結晶の製造方法

Similar Documents

Publication Publication Date Title
US7642353B2 (en) Process of making crystalline aripiprazole
US8703788B2 (en) Polymorph of nilotinib hydrochloride
KR101604501B1 (ko) Ｎ-[2-(다이에틸아미노)에틸]-5-[(5-플루오로-1,2-다이하이드로-2-옥소-3ｈ-인돌-3-일리덴)메틸]-2,4-다이메틸-1ｈ-피롤-3-카복스아미드의 결정 형태 및 이의 제조 방법
CN105367515B (zh) 一种氢溴酸沃替西汀α晶型的制备方法
CN102010359B (zh) β晶型西洛多辛的制备方法
CN105085486B (zh) 一种右旋雷贝拉唑钠的精制方法
WO2017092703A1 (fr) Procédé de préparation d'acide obéticholique amorphe
WO2010129636A2 (fr) Lénalidomide polymorphe
WO2020237643A1 (fr) Procédé de préparation d'une forme cristalline alpha de silodosine
CN104356114B (zh) 一种三水合埃索美拉唑镁的制备方法
TW201617336A (zh) 鉀離子競爭性酸阻滯劑的晶型及其製備方法
WO2012077134A1 (fr) Méthode de préparation de polymorphes d'aripiprazole
JP2019172635A (ja) アジルサルタン微細結晶の製造方法
EP2688649B1 (fr) Forme polymorphe de lénalidomide
WO2018015974A1 (fr) Formes polymorphes de sélexipag et dispersion solide amorphe de sélexipag
CA2914669C (fr) Procede de preparation de mesylate d'imatinib cristallin
CN111410626B (zh) 赛洛多辛α-晶型的制备方法
RU2017142996A (ru) Натриевая соль ингибитора транспортера мочевой кислоты и его кристаллическая форма
CN104140414B (zh) 阿昔替尼晶型的制备方法
JP2020518573A5 (fr)
MX2011004950A (es) Metodo para preparar una forma cristalina no hidratable.
TWI429621B (zh) ２－胺基－２－〔２－〔４－（３－苄基氧基苯基硫化）－２－氯化苯基〕乙基〕－１，３－丙二醇鹽酸鹽之結晶化方法
Suresh et al. Polymorphic Control of α and β dl‐Methionine through Swift Cooling Crystallization Process
JP5889391B2 (ja) １−（２−メチル−４−（２，３，４，５−テトラヒドロ−１−ベンズアゼピン−１−イルカルボニル）ベンジルカルバモイル）−ｌ−プロリン−ｎ，ｎ−ジメチルアミドの調製方法
JP6198269B2 (ja) オルメサルタンメドキソミルの製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19930330

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19930330

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 19930330

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 19930330

Country of ref document: EP

Kind code of ref document: A1

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205A DATED 15/11/2022)

122 Ep: pct application non-entry in european phase

Ref document number: 19930330

Country of ref document: EP

Kind code of ref document: A1