WO2010146428A1 - Procédé amélioré de préparation du rabéprazole - Google Patents

Procédé amélioré de préparation du rabéprazole Download PDF

Info

Publication number
WO2010146428A1
WO2010146428A1 PCT/IB2010/001371 IB2010001371W WO2010146428A1 WO 2010146428 A1 WO2010146428 A1 WO 2010146428A1 IB 2010001371 W IB2010001371 W IB 2010001371W WO 2010146428 A1 WO2010146428 A1 WO 2010146428A1
Authority
WO
WIPO (PCT)
Prior art keywords
rabeprazole
formula
crude
sodium
preparation
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/IB2010/001371
Other languages
English (en)
Inventor
Buchi Reddy Reguri
Nagamani Nagabushanam
Alagudurai Anandan
Venkateshwar Goud Thirumani
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Orchid Pharma Ltd
Original Assignee
Orchid Chemicals and Pharmaceuticals Ltd
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 Orchid Chemicals and Pharmaceuticals Ltd filed Critical Orchid Chemicals and Pharmaceuticals Ltd
Publication of WO2010146428A1 publication Critical patent/WO2010146428A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention provides an improved process for the preparation of
  • Rabeprazole sodium is chemically designated as 2-[[[4-(3-methoxypropoxy)- 3-methyl-2-pyridinyl]-methyl]sulfmyl]-lH-benzimidazole sodium salt.
  • Rabeprazole is an antiulcer drug in the class of proton pump inhibitors. It was developed by Eisai Co. and is marketed under the brand name ACIP ⁇ EX® which is available for oral administration as delayed-release, enteric-coated tablets containing 20 mg of Rabeprazole sodium.
  • US 6,313,303 discloses the preparation of sulfoxides by oxidizing thio ether with a peroxoborate salt in the presence of an acid anhydride or a metal catalyst; and the preparation of sulfoxides by oxidizing thio ether with an N- halosuccinimide, l,3-dihalo-5,5-dimethyl-hydantoin or dichloroisocyanuric acid salt in the presence of a base.
  • US 7,060,837 discloses the purification of lansoprazole using ammonia, ammonium hydroxide, diethylamine, triethylamine and methylamine in the presence of solvent.
  • the said patent utilizes acid for the isolation of lanzoprazole in pure form.
  • US 2008/0161579 discloses a process for the preparation of Rabeprazole sodium comprising oxidation of Rabeprazole sulfide with sodium hypohalite in water or a mixture of water and water miscible solvent using alkali metal hydroxide and catalyst. It also discloses a process for the preparation of Rabeprazole sulfide.
  • Rabeprazole by oxidizing the corresponding sulfide compound using about 0.8 to 1.25 equivalents of an oxidizing agent in the presence of less than or about 2.25 equivalents of a base where aqueous sodium hypohalite used as an oxidizing agent.
  • WO 2006/024890 discloses a process for the preparation of Rabeprazole in which the Rabeprazole obtained was treated with the triethylamine in hexane.
  • the use of n-hexane in the final stage is not suitable for manufacturing point of view as it is difficult to remove residual hexane solvent.
  • the main objective of the present invention is to provide a simple and economical process to produce Rabeprazole.
  • Another objective of the present invention is to provide an efficient and robust process for the purification of Rabeprazole.
  • the present invention provides a process for the preparation of compound of formula (I), or its salts.
  • the present invention provides a purification process for preparing pure Rabeprazole, which comprises treating crude Rabeprazole with diethyl amine in a solvent.
  • Rabeprazole is done by any conventional manner, for example treating the compound of formula (II) with oxidizing agent such as N-chloro succinimide, sodium hypochlorite and in the presence of sodium hydroxide.
  • oxidizing agent such as N-chloro succinimide, sodium hypochlorite and in the presence of sodium hydroxide.
  • the oxidation is preferably carried out using the organic solvent selected from ethanol, isopropanol, butanol, dichloromethane, chloroform, acetonitrile, tetrahydrofuran, acetone, ethyl acetate, butyl acetate or mixtures thereof.
  • the percentage of sodium hypochlorite used for oxidation of Rabeprazole sulfide is in the range of 6% to 20%.
  • the sodium hypochlorite was added to the reaction mass either portion wise or in a single lot and about 1.3 to 2 equivalents of an oxidizing agent and about 2 to 14 equivalents of sodium hydroxide solution was preferably employed for oxidation.
  • sodium hypochlorite with sodium hydroxide for the oxidation of Rabeprazole sulfide as reported in the prior art provides Rabeprazole containing sulfone impurity less than 0.1%, it associated with the problem that the final Rabeprazole contains higher level of unknown impurities, which ultimately affects the quality of the product.
  • the mass (molecular or formula weight) number of the impurities were identified using LCMS.
  • the obtained product contains unknown impurities of higher molecular weight in the range of 0.1-1.0 % at relative retention time (RRT) of 2.12, 3.51, 4.47, 4.85, and 4.54 RRT as measured by high performance liquid chromatography (HPLC) method provided below.
  • the purity of the product obtained is determined by high performance liquid chromatography method under the conditions mentioned below.
  • Mobile phase A 1.36g KH 2 PO4 to 1 litre water, 0.5ml OfEt 3 N, Mobile phase B: Methanol: ACN (95:5),
  • the crude Rabeprazole (purity by HPLC is 90% - 98.99%) obtained is taken in an organic solvent and treated with diethylamine to obtain the pure Rabeprazole base (purity by HPLC is 99.1% - 99.9%).
  • the obtained Rabeprazole contains less than 0.05 % of higher molecular weight impurities, particularly at 2.12 RRT, 3.51 RRT, 4.47 RRT, 4.85 RRT and 4.54 RRT.
  • the treatment of Rabeprazole with amine may optionally contain phase transfer catalyst such as TBAB (tetrabutylammmonium bromide).
  • step-iii) purification is selected from ethylacetate, methylisobutylketone, toluene acetonitrile isopropylalcohol and dichloromethane, preferably ethyl acetate.
  • the obtained rabeprazole may optionally re-crystallized using mixture of toluene: acetonitrile.
  • Rabeprazole sulfide compound of formula (II) or Rabeprazole sodium can be prepared using the methods reported in the prior arts or by following the process provided in Reference example.
  • the crude Rabeprazole (Purity by HPLC: ⁇ 99.0%) obtained was taken in ethyl acetate and treated with 0.45 equivalent of diethylamine and optionally addition of TBAB (Tetrabutylammonium bromide), heated to 50-55° C. Carbon was added over it and filtered at through the hyflo bed at 50-55 0 C. Reaction mass gradually cooled to 0-5 °C and solid obtained was filtered and washed with ethylacetate under nitrogen atmosphere. Finally material was dried under vacuum at 50-55°C till LOD is less than 0.5%. Comparative Table:
  • rabeprazole sodium having particle size less than about 120 microns, preferably less than about 90 microns.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un procédé de purification du composé rabéprazole de formule (I) ou de son sel de sodium. Formule (I)
PCT/IB2010/001371 2009-06-15 2010-06-08 Procédé amélioré de préparation du rabéprazole Ceased WO2010146428A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1407CH2009 2009-06-15
IN1407/CHE/2009 2009-06-15

Publications (1)

Publication Number Publication Date
WO2010146428A1 true WO2010146428A1 (fr) 2010-12-23

Family

ID=43355936

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2010/001371 Ceased WO2010146428A1 (fr) 2009-06-15 2010-06-08 Procédé amélioré de préparation du rabéprazole

Country Status (1)

Country Link
WO (1) WO2010146428A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102675897A (zh) * 2012-05-18 2012-09-19 陕西师范大学 硫脲/脲芳胺染料及其制备方法和应用
CN104418837A (zh) * 2013-08-19 2015-03-18 长沙市如虹医药科技有限公司 一种氧化硫醚成亚砜的方法
CN114609268A (zh) * 2022-02-10 2022-06-10 南京海纳医药科技股份有限公司 一种右旋雷贝拉唑钠原料药中有关物质的检测方法
CN114933588A (zh) * 2022-06-16 2022-08-23 岳阳职业技术学院 雷贝拉唑钠粗品的精制方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004018454A1 (fr) * 2002-08-21 2004-03-04 Teva Pharmaceutical Industries Ltd. Procede de purification de lansoprazole
WO2004063188A1 (fr) * 2003-01-15 2004-07-29 Cipla Limited Procede pharmaceutique et composes prepares au moyen de ce procede
WO2006024890A1 (fr) * 2004-08-30 2006-03-09 Apollo International Limited Procede ameliore de preparation de rabeprazole sodique sous forme amorphe
WO2006117802A2 (fr) * 2005-02-21 2006-11-09 Cipla Limited Procede de synthese d'inhibiteurs de pompe a protons
WO2008045777A2 (fr) * 2006-10-06 2008-04-17 Dr. Reddy's Labortories, Ltd. Procédé pour la préparation de dérivés de benzimidazole, et de leurs sels

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004018454A1 (fr) * 2002-08-21 2004-03-04 Teva Pharmaceutical Industries Ltd. Procede de purification de lansoprazole
WO2004063188A1 (fr) * 2003-01-15 2004-07-29 Cipla Limited Procede pharmaceutique et composes prepares au moyen de ce procede
WO2006024890A1 (fr) * 2004-08-30 2006-03-09 Apollo International Limited Procede ameliore de preparation de rabeprazole sodique sous forme amorphe
WO2006117802A2 (fr) * 2005-02-21 2006-11-09 Cipla Limited Procede de synthese d'inhibiteurs de pompe a protons
WO2008045777A2 (fr) * 2006-10-06 2008-04-17 Dr. Reddy's Labortories, Ltd. Procédé pour la préparation de dérivés de benzimidazole, et de leurs sels

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102675897A (zh) * 2012-05-18 2012-09-19 陕西师范大学 硫脲/脲芳胺染料及其制备方法和应用
CN104418837A (zh) * 2013-08-19 2015-03-18 长沙市如虹医药科技有限公司 一种氧化硫醚成亚砜的方法
CN114609268A (zh) * 2022-02-10 2022-06-10 南京海纳医药科技股份有限公司 一种右旋雷贝拉唑钠原料药中有关物质的检测方法
CN114609268B (zh) * 2022-02-10 2024-04-16 南京海纳医药科技股份有限公司 一种右旋雷贝拉唑钠原料药中有关物质的检测方法
CN114933588A (zh) * 2022-06-16 2022-08-23 岳阳职业技术学院 雷贝拉唑钠粗品的精制方法

Similar Documents

Publication Publication Date Title
EP1515963B1 (fr) Procede de preparation de composes sulfoxyde optiquement purs ou optiquement enrichis, notamment de l'esomeprazole amorphe et ses sels
CN1235899C (zh) 苯并咪唑型化合物的改进制备方法
JP2002522537A5 (fr)
US8106210B2 (en) Polymorphs of esomeprazole salts
WO2008045777A2 (fr) Procédé pour la préparation de dérivés de benzimidazole, et de leurs sels
US7439367B2 (en) Pharmaceutical process and compounds prepared thereby
CN102108077B (zh) 制备右兰索拉唑的方法
WO2010146428A1 (fr) Procédé amélioré de préparation du rabéprazole
EP2646431B1 (fr) Procédé de préparation de pazopanib à l'aide d'un nouvel intermédiaire
WO2008001392A2 (fr) Procédé amélioré de préparation de pantoprazole et de ses sels pharmaceutiquement acceptables
EP2534144B1 (fr) Procédé de préparation du sel de sodium d' Esoméprazole
KR101032600B1 (ko) 고순도 레바미피드의 제조방법
JP2014169302A (ja) （ｓ）−オメプラゾールのマグネシウム塩の固形形態とその製造方法
JP5355893B2 (ja) パントプラゾールナトリウムの製造方法
CN107074811B (zh) 改进的埃索美拉唑光学纯化方法
WO2005082888A1 (fr) Procede de preparation d'un sel magnesique d'omeprazole
CN1717402A (zh) 用于制备泮托拉唑(pantoprazole)的方法
WO2004072061A1 (fr) Procede de stabilisation de lansoprazole
EP1465890A1 (fr) Lansoprazole stable contenant plus de 500 parties par million, jusqu'a environ 3000 parties par million d'eau et plus de 200 parties par million, jusqu'a environ 5000 parties par million d'alcool
WO2004076440A1 (fr) Polymorphes de s-omeprazole
AU2003247729A1 (en) A process for preparation of optically pure or optically enriched sulfoxide compounds, including amorphous esomeprazole and salts thereof
WO2007017244A2 (fr) Procede d'elaboration de composes 2-(2-pyridylmethyl)sulfinyl-1h-benzimidazoliques substitues
WO2006134605A1 (fr) Ésoméprazole hydraté amorphe
CN101522189A (zh) 盐酸度洛西汀的多晶型

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: 10789075

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: 10789075

Country of ref document: EP

Kind code of ref document: A1