WO1992008716A1 - Separation d'enantiomeres - Google Patents

Separation d'enantiomeres Download PDF

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Publication number
WO1992008716A1
WO1992008716A1 PCT/EP1991/002096 EP9102096W WO9208716A1 WO 1992008716 A1 WO1992008716 A1 WO 1992008716A1 EP 9102096 W EP9102096 W EP 9102096W WO 9208716 A1 WO9208716 A1 WO 9208716A1
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WO
WIPO (PCT)
Prior art keywords
methyl
pyridinyl
benzimidazole
sulfinyl
methoxy
Prior art date
Application number
PCT/EP1991/002096
Other languages
German (de)
English (en)
Inventor
Bernhard Kohl
Jörg Senn-Bilfinger
Original Assignee
Byk Gulden Lomberg Chemische Fabrik Gmbh
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 Byk Gulden Lomberg Chemische Fabrik Gmbh filed Critical Byk Gulden Lomberg Chemische Fabrik Gmbh
Publication of WO1992008716A1 publication Critical patent/WO1992008716A1/fr

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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 invention relates to a process for the separation of chiral pyridylmethylsulfinyl-1H-benzimidazoles into their enantiomers.
  • the enantiomers are used in the pharmaceutical industry to manufacture drugs.
  • R1 is hydrogen, 1-4C-alkyl or 1-4C-alkoxy
  • R2 is hydrogen, trifluoromethyl, 1-4C-alkyl, 1-4C-alkoxy, completely or predominantly fluorine-substituted 1-4C-alkoxy, chlorodifluoromethoxy,
  • Chlorotrif1uorethylenedioxy means
  • R3 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy, completely or predominantly substituted by fluorine-1-4C-alkoxy, chlorodifluoromethoxy, 2-chloro-1,1,2-trifluoroethoxy or together with R2 if desired in whole or in part by fluorine substituted 1-2C-alkylenedioxy or chlorotrifluoroethylene dioxy means
  • R4 represents hydrogen or 1-4C-alkyl
  • R5 is hydrogen, 1-4C-alkyl or 1-4C-alkoxy
  • R6 denotes 1-4C-alkoxy, completely or predominantly substituted by fluorine-substituted 1-4C-alkoxy or benzyloxy
  • Rchi - X (II) in which Rchi represents a configuratively uniform, chiral radical and X represents a leaving group, converts the isomer or diastereomer mixture III obtained, wherein R1, R2, R3, R4, R5 and R6 have the meanings given above and Rchi represents a configuratively uniform, chiral radical, separates and releases the configuratively uniform, optically pure compounds I from the optically pure diastereomers by solvolysis in a strongly acidic medium.
  • 1-4C-alkyl represents straight-chain or branched alkyl radicals;
  • the butyl, i-butyl, sec-butyl, t-butyl, propyl, isopropyl, ethyl and especially the methyl radical may be mentioned.
  • 1-4C-Alkoxy stands for straight-chain or branched alkoxy radicals; Examples include the butoxy, i-butoxy, sec.-butoxy, t-butoxy, propoxy, isopropoxy, ethoxy and in particular the methoxy radical.
  • Examples of 1,24-trifluoroethoxy-, 2,2,3,3,3-pentafluoropropoxy-, perfluoroethoxy- and in particular 1,1,2- as completely or predominantly substituted by fluorine-alkoxy include 2-tetrafluoroethoxy, the trifluoromethoxy, the 2,2,2-trifluoroethoxy and the difluoromethoxy radical called.
  • R2 and R3 together mean completely or partially fluorine-substituted 1-2C-alkylenedioxy or chlorotrifluoroethyl endi oxy, the substituents R2 and R3 are bonded in adjacent positions on the benzo part of the benzimidazole ring.
  • fluorine-substituted 1-2C-alkylenedioxy are, for example, the 1,1-difluoroethylene dioxy- (-O-CF 2 -CH 2 -O-), the 1,1,2,2-tetra-fluoroethylene dioxy- ( -O-CF 2 -CF 2 -O-) and in particular the difluoromethylene dioxy (-O-CF 2 -O-) and the 1,1,2-trifluoroethylene dioxy radical (-O-CF 2 -CHF-O-).
  • Suitable compounds of the formula II are in principle all chiral, configuratively uniform compounds which are capable of reacting with the compound I or its anion with elimination of the leaving group X and the rest of which can be split off smoothly after the diastereomer separation and without undesired side reactions .
  • Rchi are all configuratively uniform residues which can be derived from naturally occurring or synthetically accessible chiral compounds and which can be cleaved solvolytically from compounds III under acidic conditions. Rchi may be mentioned in particular as residues
  • glycosyl residues which are derived from glycopyranoses, glycofuranoses or oligosaccharides and which, if desired, are partially or completely protected with protective groups customary in carbohydrate chemistry, or
  • radicals Rchi are radicals of the formula IV
  • glycosyl radicals R'-O- are those which are derived from naturally occurring mono- or disaccharides, such as arabinose, fructose, galactose, glucose, lactose, mannose, ribose, xylose, maltose, sorbose or N-acetyl-D- Derive glucosamine.
  • chiral terpene alcohol radicals R'-O- those radicals may be mentioned which are derived from a naturally occurring or synthetically easily accessible terpene alcohol.
  • terpene alcohols are: isopulegol, neomenthol, isomenthol, menthol, carveol, dihydrocarveol, terpinen-4-ol, mirtenol, citronellol, isoborneol, borneol, isopinocampheol and in particular fenchol.
  • R'-O- are, for example, the residues derived from the following alcohols: almond acid esters, cinchonidine, cinchonine, ephedrine, serine methyl ester, sitosterol, 3-hydroxy-2-methyl-propionic acid methyl ester and lactic acid ethyl ester.
  • a particularly preferred radical Rchi is the fenchyloxymethyl radical.
  • reaction of compound I with compound II is carried out in a manner familiar to the person skilled in the art.
  • it is expedient to deprotonate them i.e. starting from the salts of the compounds I with bases.
  • bases examples of basic salts are sodium, potassium, calcium, aluminum, magnesium, titanium, ammonium or guanidinium salts, for example by reacting the compounds I with the corresponding hydroxides (for example sodium hydroxide or potassium hydroxide) in a customary manner can be obtained.
  • reaction of the compounds I with compounds II is carried out in inert, protic or aprotic solvents.
  • inert, protic or aprotic solvents for example, methanol, isopropanol, dimethyl sulfoxide, acetone, acetonitrile, dioxane, dimethylformamide and preferably N-methylpyrrolidone are suitable.
  • the reaction is preferably carried out at temperatures between -30 ° C and + 100 ° C, in particular at temperatures between 0 ° C and 50 ° C.
  • the diastereomer mixture obtained after the reaction of I with II is separated in a manner known per se, for example by chromatography on suitable columns or preferably by fractional crystallization.
  • the isomers are expediently separated from one another before the diastereomers are separated, for example by column chromatography on a suitable support material (for example silica gel) and with suitable eluents (for example ethyl acetate).
  • the conformatively uniform compounds I are released from the optically pure diastereomers III by solvolysis under strongly acidic conditions.
  • suitable reagents for solvolysis are strong, more highly concentrated acids (e.g. 60-100% sulfuric acid, concentrated hydrochloric acid, anhydrous or water-containing tetrafluoroboric acid, methanesulfonic acid, trifluoromethanesulfonic acid, phosphoric acid or perchloric acid), preferably about 90
  • the release is preferably at temperatures between 0 ° and 40 ° C.
  • the procedure is advantageously such that the pH is increased as quickly as possible, for example by introducing the strongly acidic solution in buffer solution or preferably in alkali.
  • the compounds of the formula II are known or can be obtained in an analogous manner from known compounds in a manner familiar to those skilled in the art.
  • the compounds II in which Rchi has the meaning of the formula IV and X represents a chlorine atom can be obtained by chloromethylation of corresponding alcohols [e.g. in analogy to R.C. Ronald et al., J. Org. Chem. 45 (1980) 2224].
  • the compounds of formula III are new and also a subject of the invention.
  • the configuratively uniform, optically pure compounds of the formula I are likewise new and are therefore also an object of the invention.
  • connections are particularly preferred connections which can be produced by the method according to the invention.
  • pyridylmethylsulfinyl-1H-benzimidazoles can be split into their optical antipodes for the first time.
  • the fact that the release of the optically pure compounds from the diastereomers is carried out with the aid of highly concentrated mineral acids is particularly surprising, although it is known that the pyridylmethylsulfinyl-1H-benzimidazoles are very acid-labile compounds.
  • the compounds prepared according to the invention are used as active ingredients in medicaments for the treatment of gastric and intestinal diseases.
  • the active ingredients e.g. refer to European patent 166 287.

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

Abstract

La présente invention se rapporte à des pyridylméthylsulfinyle-1H-benzimidazols énantiomériquement pures et configurativement homogènes, à un procédé pour leur fabrication, ainsi qu'à de nouveaux produits intermédiaires requis par ce procédé.
PCT/EP1991/002096 1990-11-08 1991-11-06 Separation d'enantiomeres WO1992008716A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19904035455 DE4035455A1 (de) 1990-11-08 1990-11-08 Enantiomerentrennung
DEP4035455.5 1990-11-08

Publications (1)

Publication Number Publication Date
WO1992008716A1 true WO1992008716A1 (fr) 1992-05-29

Family

ID=6417839

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1991/002096 WO1992008716A1 (fr) 1990-11-08 1991-11-06 Separation d'enantiomeres

Country Status (3)

Country Link
AU (1) AU8840691A (fr)
DE (1) DE4035455A1 (fr)
WO (1) WO1992008716A1 (fr)

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WO1998028294A1 (fr) * 1996-12-20 1998-07-02 Astra Aktiebolag Nouvelle forme de compose
US5776765A (en) * 1994-11-28 1998-07-07 Astra Aktiebolag Method for preparing a pharmaceutically active enantiomeric or enantiomerically enriched sulfoxide compound by enantioselective bioreduction of a racemate sulfoxide compound
US5948789A (en) * 1994-07-15 1999-09-07 Astra Aktiebolag Process for synthesis of substituted sulphoxides
CN1055469C (zh) * 1993-05-28 2000-08-16 阿斯特拉公司 旋光纯的吡啶甲基亚磺酰基－1h－苯并咪唑类化合物的盐、及其制法和应用
EP1056456A1 (fr) * 1998-01-30 2000-12-06 Sepracor, Inc. Compositions et procedes d'utilisation du r-lansoprazole
EP1056457A1 (fr) * 1998-01-30 2000-12-06 Sepracor, Inc. Compositions de s-lansoprazole et procedes d'utilisation
US6316020B1 (en) * 1999-08-26 2001-11-13 Robert R. Whittle Pharmaceutical formulations
JP2001525366A (ja) * 1997-12-08 2001-12-11 ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング 酸不安定な活性化合物を含有する新規の投与形
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US6511996B1 (en) 1999-01-28 2003-01-28 Astrazeneca Ab Potassium salt of (s)-omeprazole
US6608092B1 (en) * 1999-06-30 2003-08-19 Takeda Chemical Industries, Ltd. Crystals of benzimidazole compounds
WO2004013126A1 (fr) * 2002-07-29 2004-02-12 Altana Pharma Ag Sel de (s)-pantoprazole et ses hydrates
WO2004052881A2 (fr) 2002-12-06 2004-06-24 Altana Pharma Ag Procede de preparation de (s)-pantoprazole
WO2004052882A1 (fr) 2002-12-06 2004-06-24 Altana Pharma Ag Procede de preparation de composes actifs optiquement pures
US6780882B2 (en) 1996-01-04 2004-08-24 The Curators Of The University Of Missouri Substituted benzimidazole dosage forms and method of using same
WO2004098577A2 (fr) * 2003-05-08 2004-11-18 Altana Pharma Ag Forme posologique contenant du (s)-pantoprazole en tant qu'ingredient actif
WO2005080374A1 (fr) 2004-02-20 2005-09-01 Astrazeneca Ab Nouveau compose utile pour la synthese de s- et r-omeprazole et procede de preparation associe
AU2003204192B2 (en) * 1993-04-27 2005-11-03 Sepracor Inc. Methods and Compositions for Treating Gastric Disorders Using Optically Pure (-) Pantoprazole
US7169799B2 (en) 2000-05-15 2007-01-30 Takeda Pharmaceutical Company Limited Process for producing crystal
WO2007074099A1 (fr) * 2005-12-28 2007-07-05 Unión Químico Farmacéutica, S.A. Procede pour la preparation de l'enantiomere (s) d'omeprazole
WO2008067037A2 (fr) 2006-10-05 2008-06-05 Santarus, Inc. Nouvelles formulations pour une libération immédiate d'inhibiteurs de pompe à protons et procédés d'utilisation de ces formulations
US7514560B2 (en) 1998-11-10 2009-04-07 Astrazeneca Ab Crystalline form of omeprazole
EP2106397A1 (fr) * 2007-09-25 2009-10-07 Hetero Drugs Limited Procédé de préparation d'ésoméprazole pur sur le plan énantiomère
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AU2003204192B2 (en) * 1993-04-27 2005-11-03 Sepracor Inc. Methods and Compositions for Treating Gastric Disorders Using Optically Pure (-) Pantoprazole
CN1055469C (zh) * 1993-05-28 2000-08-16 阿斯特拉公司 旋光纯的吡啶甲基亚磺酰基－1h－苯并咪唑类化合物的盐、及其制法和应用
KR100337274B1 (ko) * 1993-05-28 2003-12-31 아스트라제네카 악티에볼라그 피리딘메틸술피닐-1h-벤즈이미다졸화합물의광학적으로순수한염
US5948789A (en) * 1994-07-15 1999-09-07 Astra Aktiebolag Process for synthesis of substituted sulphoxides
US5776765A (en) * 1994-11-28 1998-07-07 Astra Aktiebolag Method for preparing a pharmaceutically active enantiomeric or enantiomerically enriched sulfoxide compound by enantioselective bioreduction of a racemate sulfoxide compound
US6780882B2 (en) 1996-01-04 2004-08-24 The Curators Of The University Of Missouri Substituted benzimidazole dosage forms and method of using same
USRE45198E1 (en) 1996-01-04 2014-10-14 The Curators Of The University Of Missouri Omeprazole solution and method for using same
CN1109684C (zh) * 1996-12-20 2003-05-28 阿斯特拉公司 新的化合物形态
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