US20040235903A1 - Amorphous form of esomeprazole salts - Google Patents

Amorphous form of esomeprazole salts Download PDF

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Publication number
US20040235903A1
US20040235903A1 US10/690,897 US69089703A US2004235903A1 US 20040235903 A1 US20040235903 A1 US 20040235903A1 US 69089703 A US69089703 A US 69089703A US 2004235903 A1 US2004235903 A1 US 2004235903A1
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United States
Prior art keywords
esomeprazole
salt
amorphous form
cation
solution
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Abandoned
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US10/690,897
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English (en)
Inventor
Mahavir Khanna
Bakthavathsalan Vijayaraghavan
Mohan Prasad
Yatendra Kumar
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Ranbaxy Laboratories Ltd
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Ranbaxy Laboratories Ltd
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Assigned to RANBAXY LABORATORIES LIMITED reassignment RANBAXY LABORATORIES LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KHANNA, MAHAVIR SINGH, KUMAR, YATENDRA, PRASAD, MOHAN, VIJAYARAGHAVAN, BAKTHAVATHSALAN
Publication of US20040235903A1 publication Critical patent/US20040235903A1/en
Priority to US11/946,193 priority Critical patent/US7482463B2/en
Abandoned legal-status Critical Current

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Definitions

  • the field of the invention relates to an amorphous form of the salts of the ( ⁇ ) enantiomer or (S)-enantiomer of omeprazole, i.e., esomeprazole.
  • the invention also relates to processes for preparing amorphous esomeprazole salts and pharmaceutical compositions that include the amorphous esomeprazole salts.
  • omeprazole is 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole.
  • Omeprazole and therapeutically acceptable salts thereof are described in U.S. Pat. No. 4,255,431.
  • Certain specific alkaline salts of omeprazole are disclosed in U.S. Pat. No. 4,738,974.
  • Omeprazole is transformed into an effective inhibitor of gastric acid secretion in mammals, and is therefore useful as an anti-ulcer agent.
  • Omeprazole may be used to prevent and/or treat gastric acid related disorders and gastrointestinal inflammatory diseases in mammals. In man, for example, omeprazole may be used to prevent and/or treat gastritis, gastric ulcer and duodenal ulcer.
  • Omeprazole is a racemic mixture of its two single enantiomers, the (R)- and (S)-enantiomer of omeprazole. These enantiomers are commonly referred to as (R)-omeprazole and (S)-omeprazole, respectively.
  • the enantiomer, (S)-omeprazole is commonly referred to as esomeprazole.
  • WO 94/27988 discloses certain salts of the single enantiomers of omeprazole and their preparation. These compounds are described as having improved pharmacokinetic properties which give an improved therapeutic profile, such as a lower degree of variation between individuals taking the compound.
  • WO 96/02535 discloses a process for preparing the single enantiomers of omeprazole and salts thereof.
  • WO 98/54171 discloses a process for the preparation of the trihydrate of the magnesium salt of (ES)-omeprazole.
  • Esomeprazole like many other similar benzimidazole compounds, is not stable in its free form and is susceptible to degradation in acid and neutral media. It has been found that alkali metal or alkaline earth metal salts of esomeprazole are more stable during storage than the corresponding neutral form.
  • U.S. Pat. No. 5,714,505 describes alkaline salts of the ( ⁇ ) enantiomer of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridiniyl)methyl]sulfinyl]-1H-benzimidazoles (i.e., esomeprazole) including the magnesium salt, which are used for inhibiting gastric acid secretion.
  • Esomeprazole magnesium is prepared according to Examples 5, 6, and 7 of the '505 patent in optically pure crystalline form by precipitation/crystallization.
  • U.S. Pat. No. 6,124,464 discloses another process for preparing crystalline esomeprazole magnesium.
  • U.S. Pat. No. 6,369,085 discloses three different types of crystalline esomeprazole magnesium viz. dihydrate form A, dihydrate form B and the trihydrate form.
  • the inventors are not aware of any disclosure of an amorphous form of esomeprazole salts, including amorphous esomeprazole magnesium, in the prior art. It is known that different morphs of biologically active compounds may have different absorption profile in vivo and consequently different pharmacokinetic profile.
  • Embodiments of the amorphous form of the salt of esomeprazole may include one or more of the following features.
  • the cation may be selected from the group that includes Na, Mg, Li, K, Ca, and N(R) 4 , where R is hydrogen or an alkyl with 1-4 carbon atoms.
  • the amorphous form of the salt of esomeprazole may have the X-ray diffraction pattern of FIG. 1 and the IR spectra of FIG. 2.
  • composition that includes a therapeutically effective amount of an amorphous form of a salt of esomeprazole; and one or more pharmaceutically acceptable carriers, excipients or diluents.
  • Embodiments of the pharmaceutical composition may include one or more of the following features.
  • the cation may be selected from the group that includes Na, Mg, Li, K, Ca, and N(R) 4 , where R is hydrogen or an alkyl with 1-4 carbon atoms.
  • the amorphous form of the salt of esomeprazole may have the X-ray diffraction pattern of FIG. 1 and the IR spectra of FIG. 2.
  • a process for the preparation of a salt of the amorphous form of esomeprazole includes preparing a solution of a salt of esomeprazole in one or more solvents; and recovering the salt of esomeprazole in the amorphous form from the solution thereof by the removal of the solvent.
  • Embodiments of the process may include one or more of the following features.
  • the cation may be selected from the group that includes Na, Mg, Li, K, Ca, and N(R) 4 , where R is hydrogen or an alkyl with 1-4 carbon atoms.
  • the solvent may be one or more of lower alkanol, ketone, ester, chlorinated solvent, acetonitrile or mixtures thereof.
  • the lower alkanol may include one or more of primary, secondary and tertiary alcohol having from one to six carbon atoms.
  • the lower alkanol may include one or more of methanol, ethanol, denatured spirit, n-propanol, isopropanol, n-butanol, isobutanol, and t-butanol.
  • the lower alkanol may include one or more of methanol, ethanol, and denatured spirit.
  • the ketone may include one or more of acetone, 2-butanone, and 4-methylpentan-2-one.
  • the ester may include one or more of ethyl acetate and n-butyl acetate.
  • the chlorinated solvent may include one or more of chloroform and dichloromethane. Removing the solvent may include one or more of distillation, distillation under vacuum, evaporation, spray drying, and freeze drying.
  • the salt of esomeprazole in an amorphous form may be recovered from the solution by spray drying.
  • the salt of esomeprazole in an amorphous form may be recovered from the solution by freeze-drying.
  • the process may include further forming of the product so obtained into a finished dosage form.
  • the process may include further drying of the product obtained from the solution.
  • the process may further include adding one or both of an organic amine and ammonia to the solution.
  • the organic amine and/or ammonia may be added to the solution prior to removal of the solvent.
  • the process may produce the amorphous form of the salt of esomeprazole having the X-ray diffraction pattern of FIG. 1 and the IR spectra of FIG. 2.
  • FIG. 1 is an x-ray powder diffraction pattern of amorphous esomeprazole.
  • FIG. 2 is an infra-red spectra in KBr of amorphous esomeprazole magnesium prepared as described herein.
  • the mentors have found a new form of esomeprazole salts, the amorphous form and, in particular, the amorphous esomeprazole magnesium salt.
  • the new form is characterized by its X-ray powder diffraction pattern and IR spectra as shown in FIGS. 1 and 2, respectively.
  • the inventors also have developed a process for the preparation of the amorphous form of esomeprazole salts, including the esomeprazole magnesium salt, by recovering the amorphous esomeprazole salt from a solution thereof in a suitable solvent by spray drying.
  • the resulting amorphous form of salts of esomeprazole include, for example, Na, Mg, Li, K, Ca, and N(R) 4 , where R is hydrogen or an alkyl group with 1-4 carbon atoms.
  • the inventors also have developed pharmaceutical compositions that contain the amorphous form of the esomeprazole salts, including the esomeprazole magnesium salt, in admixture with one or more solid or liquid pharmaceutical diluents, carriers, and/or excipients. These pharmaceutical compositions may be used for the treatment of gastric acid-related diseases by inhibition of gastric acid secretion.
  • the solution of esomeprazole salt may be obtained by dissolving a crystalline esomeprazole salt in a suitable solvent.
  • a suitable solvent such a solution may be obtained directly from a reaction in which esomeprazole salt is formed.
  • the solvent may be removed from the solution by a technique which includes, for example, distillation, distillation under vacuum, evaporation, spray drying, and freeze drying.
  • a salt of esomeprazole in amorphous form is recovered from the solution using a spray drying technique.
  • a Mini-Spray Dryer Model: Buchi 190, Switzerland
  • the Buchi 190 Mini-Spray Dryer operates on the principle of nozzle spraying in a parallel flow, i.e., the sprayed product and the drying gas flow in the same direction.
  • the drying gas can be air or inert gases such as nitrogen, argon and carbon dioxide.
  • a salt of esomeprazole in amorphous form can be recovered from the solution using a freeze drying technique.
  • a freeze dryer Model:Virtis Genesis SQ Freeze Dryer
  • the Virtis Genesis SQ Freeze Dryer operates on the principle of lyophilization, i.e., a process of stabilizing initially wet materials (aqueous solution or suspensions) by freezing them, then subliming the ice while simultaneously desorbing some of the bound moisture (primary drying). Following removal of the ice, desorption may be continued (secondary drying). This process may be carried out under vacuum.
  • suitable solvent includes any solvent or solvent mixture in which esomeprazole salt, including esomeprazole magnesium, is soluble, including, for example, nitriles, cyclic ethers, lower alkanol, ketones, esters, chlorinated solvents, acetonitrile and mixtures thereof.
  • alcohols include methanol, ethanol, isopropanol, and the like.
  • halogenated hydrocarbons include dichloromethane, dichloroethane, dibromoethane, and the like.
  • nitrile include acetonitrile and the like.
  • cyclic ethers include tetrahydrofuran, dioxane, and the like.
  • alkanol examples include those primary, secondary and tertiary alcohols having from one to six carbon atoms.
  • Suitable lower alkanol solvents include methanol, ethanol, denatured spirit, n-propanol, isopropanol, n-butanol, isobutanol and t-butanol.
  • ketones or esters include solvents such as acetone, 2-butanone, 4-methylpentan-2-one, ethyl acetate and n-butylacetate.
  • a suitable chlorinated solvent includes one or both of dichloromethane and chloroform. Mixtures of all of these solvents are also contemplated.
  • An organic amine or ammonia may optionally be added to the solution of esomeprazole salt, including esomeprazole magnesium, before spray drying.
  • the organic amine may be one or more of diethylamine, triethylamine, and the like.
  • One purpose of adding the organic amine or ammonia is to provide stability to the esomprazole during processing.
  • crystalline esomeprazole magnesium may be in the form of any of the various polymorphic forms known in the prior art including dihydrate form A, dihydrate form B, trihydrate, etc.
  • Esomeprazole magnesium may be prepared by any of the known methods such as those cited in U.S. Pat. Nos. 5,714,504; 6,124,464; and 6,369,085.
  • a solution of esomeprazole magnesium obtained in situ during the preparation process may be used as such for spray drying.
  • the spray drying may be accomplished using a spray dryer which operates on the principle of nozzle spraying in a parallel flow, i.e., the sprayed product and the drying gas flow in the same direction.
  • the drying gas can be air or one or more inert gases such as nitrogen, argon, and carbon dioxide.
  • the product obtained may be further or additionally dried to achieve the desired moisture values.
  • the product may be further or additionally dried in a tray drier, dried under vacuum and/or in a Fluid Bed Dryer.
  • the resulting amorphous form of esomeprazole salt and, in particular, esomeprazole magnesium may be formulated into ordinary dosage forms such as, for example, tablets, capsules, pills, solutions, etc.
  • the medicaments can be prepared by conventional methods with conventional pharmaceutical excipients.
  • the amorphous form of esomeprazole magnesium may also be administered by controlled release means and/or delivery devices.
  • the amorphous esomeprazole salt dosage forms described herein can be used in a method for treatment of gastric acid related diseases.
  • the method of treatment includes administering to a mammal in need of treatment a dosage form that includes a therapeutically effective amount of the amorphous form of esomeprazole salt, including the esomeprazole magnesium salt.
  • Esomeprazole magnesium trihydrate 200 g was dissolved in a mixture of dichloromethane (1200 ml) and methanol (1200 ml) at 25-30° C. Any undissolved material was filtered off and triethylamine (2 ml) was added to the filtrate. The clear solution thus obtained was spray dried in a mini spray dryer (Model Buchi-190) with an inlet temperature of 65-68° C. and an outlet temperature of 22-42° C. in 2 to 3 hours. The solid was further dried under vacuum at 60-65° C. for 14 to 15 hours to yield 120 g of esomeprazole magnesium of amorphous form.
  • Esomeprazole magnesium trihydrate (20 g) was dissolved in methanol (200 ml) at 25-30° C. Any undissolved material was filtered off and triethylamine (0.2 ml) was added to the filtrate. The clear solution thus obtained was subjected to spray drying with an inlet temperature of 65-68° C. and an outlet temperature of 22-42° C. The solid was further dried under vacuum at 60-65° C. for 14 to 15 hours to yield 11.5 g of esomeprazole magnesium of amorphous form.
  • Esomeprazole magnesium trihydrate (10 g) was dissolved in a mixture of dichloromethane (50 ml) and ethanol (70 ml) at 25-30° C. Any undissolved material was filtered off. The clear solution thus obtained was spray dried with an inlet temperature of 70-80° C. and an outlet temperature of 22-42° C. The solid was further dried under vacuum at 60-65° C. for 14 to 15 hours to yield 5.82 g of esomeprazole magnesium of amorphous form.
  • Esomeprazole magnesium trihydrate (100 g) was dissolved in methanol (1000 ml) at 25-30° C. Any undissolved material was filtered off. The clear solution thus obtained was spray dried with an inlet temperature of 65-68° C. and an outlet temperature of 22-42° C. The solid was further dried under vacuum at 60-65° C. for 14 to 15 hours to yield 55 g of esomeprazole magnesium of amorphous form.

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  • Organic Chemistry (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
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  • Plural Heterocyclic Compounds (AREA)
US10/690,897 2002-10-22 2003-10-22 Amorphous form of esomeprazole salts Abandoned US20040235903A1 (en)

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US (2) US20040235903A1 (fr)
EP (1) EP1556043A1 (fr)
CN (1) CN1728997A (fr)
AU (1) AU2003278406A1 (fr)
BR (1) BR0315574A (fr)
EA (1) EA200500673A1 (fr)
NO (1) NO20052474L (fr)
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US20070116729A1 (en) * 2005-11-18 2007-05-24 Palepu Nageswara R Lyophilization process and products obtained thereby
US20070149573A1 (en) * 2005-12-23 2007-06-28 Savanovic Lidija V S-omeprazole magnesium
EP1856101A2 (fr) * 2005-03-08 2007-11-21 Dr. Reddy's Laboratories Ltd. Procede de preparation de sels amorphes
WO2007008588A3 (fr) * 2005-07-07 2009-04-23 Reddys Lab Ltd Dr Omeprazole de forme b
US20090197919A1 (en) * 2006-06-07 2009-08-06 Rolf Bergman Novel Method for Preparation of Ammonium Salts of Esomeprazole
WO2009047775A3 (fr) * 2007-10-08 2010-02-18 Hetero Drugs Limited Polymorphes de sels de l'ésoméprazole
EP2842953A1 (fr) 2007-02-21 2015-03-04 Cipla Limited Procédé pour la Préparation de Ésoméprazole Magnésium Dihydraté

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WO2005105054A1 (fr) * 2004-04-15 2005-11-10 Dr. Reddy's Laboratories Ltd. Forme de dosage ayant une stabilité polymorphique
NZ551970A (en) 2004-06-24 2010-01-29 Astrazeneca Ab New process for the preparation of crystal modifications for use in the preparation of esomeprazole sodium salt
ES2246149B1 (es) * 2004-07-02 2007-06-01 Esteve Quimica, S.A. Formas solidas de la sal magnesica de s-omeprazol y procedimientos para su preparacion.
CN101111233A (zh) 2004-12-23 2008-01-23 兰贝克赛实验室有限公司 稳定的口服苯并咪唑组合物及其制备方法
DE102005008412A1 (de) * 2005-02-24 2006-09-07 Ratiopharm Gmbh Piperazinsalz des Omeprazols und dessen Enantiomere
WO2007031845A2 (fr) * 2005-09-14 2007-03-22 Glenmark Pharmaceuticals Limited Formes polymorphiques de sels de magnesium de (s)-omeprazole et procedes de preparation desdites formes
EP1948637A4 (fr) * 2005-11-14 2010-09-08 Hetero Drugs Ltd Procédé d'obtention d'ésoméprazole amorphe
CA2631919A1 (fr) 2005-12-05 2007-06-14 Astrazeneca Ab Nouveau procede de fabrication d'esomeprazole sous forme non saline
EP1801110A1 (fr) 2005-12-22 2007-06-27 KRKA, tovarna zdravil, d.d., Novo mesto Sel d'arginine d'ésoméprazole
EA200900985A1 (ru) 2007-01-31 2009-12-30 Крка, Товарна Здравил, Д. Д., Ново Место Способ получения оптически чистого омепразола
US8911787B2 (en) 2008-02-26 2014-12-16 Ranbaxy Laboratories Limited Stable oral benzimidazole compositions and process of preparation thereof
EP2147918A1 (fr) 2008-07-21 2010-01-27 LEK Pharmaceuticals D.D. Procédé de préparation de magnésium d'oméprazole S dans une forme stable
WO2010097583A1 (fr) * 2009-02-24 2010-09-02 Cipla Limited Polymorphe de l'ésoméprazole de potassium et sa préparation
WO2011095984A1 (fr) * 2010-02-02 2011-08-11 Glenmark Generics Limited Procédé de préparation d'ésoméprazole amorphe
FR3062129B1 (fr) * 2017-01-23 2019-04-05 Minakem Procede d'obtention du sel de magnesium dihydrate de l'esomeprazole
CN113387929A (zh) * 2021-06-30 2021-09-14 江苏中邦制药有限公司 一种艾司奥美拉唑镁三水合物的制备方法

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US4738974A (en) * 1983-03-04 1988-04-19 Aktiebolaget Hassle Base addition salts of omeprazole
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US5714505A (en) * 1994-01-05 1998-02-03 Astra Aktiebolag Method for treatment of psoriasis, by omeprazole or related compounds
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US6369085B1 (en) * 1997-05-30 2002-04-09 Astrazeneca Ab Form of S-omeprazole
US6207188B1 (en) * 1997-06-27 2001-03-27 Astrazeneca Ab Omeprazole sodium salt
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US20080146615A1 (en) * 2004-12-20 2008-06-19 Dr. Reddy's Laboratories Limited Pharmaceutical Compositions Comprising Amorphous Benzimidazole Compounds
US20090324728A1 (en) * 2004-12-20 2009-12-31 Dr. Reddy's Laboratories Limited Pharmaceutical compositions comprising amorphous benzimidazole compounds
WO2006069159A3 (fr) * 2004-12-20 2006-12-21 Reddys Lab Ltd Dr Compositions pharmaceutiques comprenant des composes de benzimidazole amorphe
EP1856101A4 (fr) * 2005-03-08 2009-10-21 Reddys Lab Ltd Dr Procede de preparation de sels amorphes
EP1856101A2 (fr) * 2005-03-08 2007-11-21 Dr. Reddy's Laboratories Ltd. Procede de preparation de sels amorphes
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US20070149573A1 (en) * 2005-12-23 2007-06-28 Savanovic Lidija V S-omeprazole magnesium
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US20090197919A1 (en) * 2006-06-07 2009-08-06 Rolf Bergman Novel Method for Preparation of Ammonium Salts of Esomeprazole
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WO2009047775A3 (fr) * 2007-10-08 2010-02-18 Hetero Drugs Limited Polymorphes de sels de l'ésoméprazole

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EP1556043A1 (fr) 2005-07-27
BR0315574A (pt) 2005-09-20
CN1728997A (zh) 2006-02-01
NO20052474D0 (no) 2005-05-23
US7482463B2 (en) 2009-01-27
EA200500673A1 (ru) 2005-12-29
AU2003278406A1 (en) 2004-05-13
NO20052474L (no) 2005-05-23
WO2004037253A1 (fr) 2004-05-06
US20080119654A1 (en) 2008-05-22

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