US20060178406A1 - Process for production of sulfoxide derivatives or salts thereof in the amorphous state - Google Patents

Process for production of sulfoxide derivatives or salts thereof in the amorphous state Download PDF

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US20060178406A1
US20060178406A1 US10/546,994 US54699405A US2006178406A1 US 20060178406 A1 US20060178406 A1 US 20060178406A1 US 54699405 A US54699405 A US 54699405A US 2006178406 A1 US2006178406 A1 US 2006178406A1
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methylsulfinyl
methoxypropoxy
methylpyridine
amorphous substance
sodium salt
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Masahiko Tsujii
Yukio Morita
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Eisai R&D Management Co Ltd
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Eisai Co Ltd
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Assigned to EISAI CO., LTD. reassignment EISAI CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MORITA, YUKIO, TSUJII, MASAHIKO
Publication of US20060178406A1 publication Critical patent/US20060178406A1/en
Assigned to EISAI R&D MANAGEMENT CO., LTD. reassignment EISAI R&D MANAGEMENT CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: EISAI CO., LTD.
Priority to US11/939,418 priority Critical patent/US7754887B2/en
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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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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 present invention relates to a method of effectively preparing an amorphous substance of sulfoxide derivative or the salt thereof, wherein the substance is useful as medical drugs such as inhibitors of gastric acid secretion and anti-ulcer agents, and said method comprises heat-drying a solvated crystal of sulfoxide derivative or the salt thereof.
  • the method of preparing an amorphous substance by freeze-dry is general means for obtaining drugs, as a solid, mainly unstable protein drugs and antibiotics.
  • an object of the present invention is to provide a method of effectively preparing an amorphous substance of sulfoxide derivative (I) or the salt thereof in industrial scale, said method overcoming the above-mentioned problem caused in the freeze-dry method.
  • the inventors have assiduously conducted investigations in light of the above-mentioned things. They have consequently found that a colorless amorphous substance of sulfoxide derivative (I) or the salt thereof is successively, stably obtained in industrial scale by subjecting a solvated crystal of sulfoxide derivative (I) or the salt thereof to heat-drying at high temperature which defies the prior common sense, and that said drying method provides the amorphous substance of sulfoxide derivative (I) or the salt thereof, whose particle diameter is in a uniformly arranged condition. This finding has led to the completion of the present invention.
  • the present invention provides the following ⁇ 1> to ⁇ 32>:
  • a method of preparing an amorphous substance of sulfoxide derivative (I) or the salt thereof which comprises heat-drying an solvated crystal of sulfoxide derivative represented by the following formula (I) or the salt thereof: wherein R 1 represents a hydrogen atom, a methoxy group or a difluoromethoxy group; R 2 represents a methyl group or a methoxy group; R 3 represents a 3-methoxypropoxy group, a methoxy group or a 2,2,2-trifluoroethoxy group; R 4 represents a hydrogen atom or a methyl group; respectively, and B represents a hydrogen atom, an alkaline metal or 1 ⁇ 2 alkaline earth metal.
  • sulfoxide derivative is 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]-methylsulfinyl]-1H-benzimidazole, 2-[[4-(2,2,2-trifluoroethoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole, 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridyl)methylsulfinyl]-1H-benzimidazole or 5-difluoromethoxy-2-[(4,5-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole.
  • a method of preparing an amorphous substance of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt comprising heat-drying an acetone complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt or an acetonitrile complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-
  • a method of preparing an amorphous substance of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt which comprises heat-drying an acetone complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt under reduced pressure.
  • amorphous substance of sulfoxide derivative (I) or the salt thereof has 50 ⁇ m or less of average particle diameter and 80 ⁇ m or less of 90% cumulative diameter, measured by laser diffractometry.
  • ⁇ 11> The method according to any one of the above items ⁇ 1> to ⁇ 9>, wherein the amorphous substance of sulfoxide derivative (I) or the salt thereof has 30 ⁇ m or less of average particle diameter and 50 ⁇ m or less of 90% cumulative diameter, measured by laser diffractometry.
  • ⁇ 12> The method according to any one of the above items ⁇ 1> to ⁇ 9>, wherein the amorphous substance of sulfoxide derivative (I) or the salt thereof has from 1 to 75 ⁇ m of particle diameter, from 5 to 30 ⁇ m of average particle diameter and from 10 to 50 ⁇ m of 90% cumulative diameter, measured by laser diffractometry.
  • amorphous substance of sulfoxide derivative (I) or the salt thereof has from 1 to 50 ⁇ m of particle diameter, from 5 to 15 ⁇ m of average particle diameter and from 10 to 25 ⁇ m of 90% cumulative diameter, measured by laser diffractometry.
  • ⁇ 14> The method according to any one of the above items ⁇ 1> to ⁇ 9>, wherein the amorphous substance of sulfoxide derivative (I) or the salt thereof has from 1 to 75 ⁇ m of particle diameter, measured by laser diffractometry.
  • ⁇ 15> The method according to any one of the above items ⁇ 1> to ⁇ 9> and ⁇ 14>, wherein the amorphous substance of sulfoxide derivative (I) or the salt thereof has from 1 to 50 ⁇ m of particle diameter, measured by laser diffractometry.
  • ⁇ 16> The method according to any one of the above items ⁇ 1> to ⁇ 9>, ⁇ 14> and ⁇ 15>, wherein the amorphous substance of sulfoxide derivative (I) or the salt thereof has from 5 to 30 ⁇ m of average particle diameter, measured by laser diffractometry.
  • ⁇ 17> The method according to any one of the above items ⁇ 1> to ⁇ 9> and ⁇ 14> to ⁇ 16>, wherein the amorphous substance of sulfoxide derivative (I) or the salt thereof has from 5 to 15 ⁇ m of average particle diameter, measured by laser diffractometry.
  • ⁇ 18> The method according to any one of the above items ⁇ 1> to ⁇ 9> and ⁇ 14> to ⁇ 17>, wherein the amorphous substance of sulfoxide derivative (I) or the salt thereof has from 10 to 50 ⁇ m of 90% cumulative diameter, measured by laser diffractometry.
  • amorphous substance according to the above items ⁇ 20> to ⁇ 23> which has from 1 to 75 ⁇ m of particle diameter, from 5 to 30 ⁇ m of average particle diameter and from 10 to 50 ⁇ m of 90% cumulative diameter, measured by laser diffractometry.
  • amorphous substance according to the above items ⁇ 20>to ⁇ 23> which has from 1 to 50 ⁇ m of particle diameter, from 5 to 15 ⁇ m of average particle diameter and from 10 to 25 ⁇ m of 90% cumulative diameter, measured by laser diffractometry.
  • ⁇ 26> The amorphous substance according to the above items ⁇ 20>to ⁇ 23>, which has from 1 to 75 ⁇ m of particle diameter, measured by laser diffractometry.
  • ⁇ 27> The amorphous substance according to the above items ⁇ 20> to ⁇ 23> and ⁇ 26>, which has from 1 to 50 ⁇ m of particle diameter, measured by laser diffractometry.
  • ⁇ 28> The amorphous substance according to the above items ⁇ 20> to ⁇ 23>, ⁇ 26> and ⁇ 27>, which has from 5 to 30 ⁇ m of average particle diameter, measured by laser diffractometry.
  • ⁇ 29> The amorphous substance according to the above items ⁇ 20> to ⁇ 23> and ⁇ 26> to ⁇ 28>, which has from 5 to 15 ⁇ m of average particle diameter, measured by laser diffractometry.
  • amorphous substance according to the above items ⁇ 20> to ⁇ 23> and ⁇ 26> to ⁇ 29> which has from 10 to 50 ⁇ m of 90% cumulative diameter, measured by laser diffractometry.
  • ⁇ 31> The amorphous substance according to the above items ⁇ 20> to ⁇ 23> and ⁇ 26> to ⁇ 30>, which has from 10 to 25 ⁇ m of 90% cumulative diameter, measured by laser diffractometry.
  • FIG. 1 is a graph showing powder X-ray diffraction pattern as for an acetone complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]-methylsulfinyl]-1H-benzimidazole sodium salt.
  • FIG. 2 is a graph showing powder X-ray diffraction pattern as for the freeze-dried product (Reference Example 2).
  • FIG. 3 is a graph showing powder X-ray diffraction pattern as for the heat-dried product (Example 1).
  • FIG. 4 is a graph showing particle size distribution as for the freeze-dried product (Reference Example 2).
  • FIG. 5 is a graph showing particle size distribution as for the heat-dried product (Example 3).
  • FIG. 6 is a graph showing the result of thermal analysis as for the acetone complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]-methylsulfinyl]-1H-benzimidazole sodium salt.
  • FIG. 7 is a graph showing 1 H-NMR chart as for the acetonitrile complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt.
  • FIG. 8 is a graph showing powder X-ray diffraction pattern as for the acetonitrile complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]-methylsulfinyl]-1H-benzimidazole sodium salt.
  • FIG. 9 is a graph showing powder X-ray diffraction pattern as for the heat-dried product (Example 16).
  • alkaline metal used herein concretely means, for example, sodium, potassium, lithium and the like.
  • alkaline earth metal concretely means, for example, calcium, magnesium and the like. Sodium or magnesium is preferable. Sodium is more preferable.
  • the salt of sulfoxide derivative is represented by the following formula (II): wherein each of R 1 , R 2 , R 3 and R 4 has the same meaning as defined above, and B′ represents an alkaline earth metal.
  • the sulfoxide derivative (I) or the salt thereof may include, for example, 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole disclosed in U.S. Pat. No. 5,045,552 (general designation: Rabeprazole); 2-[[4-(2,2,2-trifluoroethoxy)-3-methylpyridine-2-yl]-methylsulfinyl]-1H-benzimidazole disclosed in U.S. Pat. No.
  • the solvated crystal of sulfoxide derivative (I) or the salt thereof may include, for example, the acetone complex (acetone-solvate crystal), the acetonitrile complex (acetonitrile-solvate crystal) or the ethyl acetate complex (ethyl acetate-solvate crystal) of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole, 2-[[4-(2,2,2-trifluoroethoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole, 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridyl)methylsulfinyl]-1H-benzimidazole or 5-difluoromethoxy-2-[(4,5-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole
  • the acetone complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt and the acetonitrile complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt are preferable.
  • the acetone complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt is more preferable.
  • the solvated crystal of sulfoxide derivative (I) or the salt thereof is basically obtained by, for example, contacting sulfoxide derivative (I) or the salt thereof with a solvent or dissolving it in a solvent, and then treating the resultant, for example, crystallizing the resultant.
  • acetone complex of sulfoxide derivative (I) or the salt thereof is disclosed in U.S. Pat. No. 6,180,652, and, in particular, is represented by the following formula.
  • the complex or the salt thereof can be prepared according to the method disclosed in the specification: wherein R 1 represents a hydrogen atom, a methoxy group or a difluoromethoxy group; R 2 represents a methyl group or a methoxy group; R 3 represents a 3-methoxypropoxy group, a methoxy group or a 2,2,2-trifluoroethoxy group; R 4 represents a hydrogen atom or a methyl group; respectively, m and n each independently represents an integer of 1 to 4, and B represents a hydrogen atom, an alkaline metal or 1 ⁇ 2 alkaline earth metal.
  • the acetonitrile complex of sulfoxide derivative (I) or the salt thereof can be prepared by dissolving sulfoxide derivative (I) or the salt thereof in acetonitrile, being left to stand, filtering off the precipitated crystal and drying it.
  • the acetone complex or acetonitrile complex of sulfoxide derivative (I) or the salt thereof can be used after filtering off without drying in the method of preparing the amorphous substance.
  • amorphous substance used herein means an amorphous solid.
  • moisture gas used herein means gases comprising water and being inert to the sulfoxide derivative (I) or the salt thereof, such as moist air or moist nitrogen.
  • the moisture content of the moist gas is in the range of from 15 to 60%, preferably from 30 to 40%, in case where the temperature of the moist gas is in the range of from 20 to 35° C.
  • inert medium means gas or liquid being inert to the sulfoxide derivative (I) or the salt thereof.
  • the inert gas may include nitrogen gas, argon gas, dried air and the like.
  • the inert liquid may include, but is not limited to, for example, aliphatic hydrocarbons such as 1-heptane and cyclohexene; aromatic hydrocarbons such as toluene; ethers; and the like, as long as 1) the inert liquid does not dissolve the sulfoxide derivative (I) or the salt thereof and 2) the inert liquid has boiling point of about 60° C. or more.
  • the amorphous substance of sulfoxide derivative (I) or the salt thereof can be basically prepared by incorporating an solvated crystal of sulfoxide derivative (I) or the salt thereof into a vibrating vacuum dryer and heat-drying it while the heat medium is circulated. Preferably, heat-drying is conducted under reduced pressure.
  • the heat-drying according to the present invention can be conducted with moist gas.
  • the heat-drying is conducted by removing the solvent from the solvated crystal while the moist gas flows little by little so as to contact with the sulfoxide derivative (I) or the salt thereof at the same time of depressurizing under the heat-vibrating condition.
  • the solvent can be separated by replacing the solvent in the powder with water to facilitate the diffusion migration thereof and promote the evaporation thereof. Accordingly, said drying has an advantage that the heating temperature and depressurizing degree can be decreased by using the moist gas.
  • the heat-drying according to the present invention can be conducted in an inert medium.
  • an inert gas used as the inert medium
  • the heat-drying is conducted by flowing the inert gas little by little into the reaction container so as to contact with the sulfoxide derivative (I) or the salt thereof at the same time of heating.
  • an inert liquid used as the inert medium
  • sulfoxide derivative (I) or the salt thereof is suspended, dispersed in the inert liquid, and heated under the condition with good heat conductance.
  • the heat-drying can be usually conducted in the range of from 30 to 130° C., preferably from 60 to 120° C., more preferably 100 to 110° C.
  • the heat-drying time can be usually in the range of from 1 to 160 hour(s), preferably from 3 to 30 hours, although the drying time depends on a drying equipment, heating temperature, degree of depressurization, scale and the like.
  • the measurement of particle size distribution by laser diffractometry can be conducted, for example, by using “Microtrac X100 ” (made by Leeds And Northrup).
  • the amorphous substance of sulfoxide derivative (I) or the salt thereof which is prepared by conducting the above-mentioned heat-drying, is measured by the laser diffractometry
  • the amorphous substance of sulfoxide derivative (I) or the salt thereof has 50 ⁇ m or less, preferably 30 ⁇ m or less of average particle diameter, and 80 ⁇ m or less, preferably 50 ⁇ m or less of 90% cumulative diameter.
  • the amorphous substance of sulfoxide derivative (I) or the salt thereof which is prepared by conducting the above-mentioned heat-drying, is measured by the laser diffractometry
  • the amorphous substance of sulfoxide derivative (I) or the salt thereof has from 1 to 75 ⁇ m of particle diameter, from 5 to 30 ⁇ m of average particle diameter and from 10 to 50 ⁇ m of 90% cumulative diameter.
  • the amorphous substance has from 1 to 50 ⁇ m of particle diameter, from 5 to 15 ⁇ m of average particle diameter and from 10 to 25 ⁇ m of 90% cumulative diameter.
  • the step of making the particle diameter the uniform size can be deleted by obtaining the particles each having the above-mentioned ranges.
  • the specific surface of the particles each having relatively small particle diameter can be generally depressed, the particles each having an improved water-resistance property can be obtained.
  • the titled compound was prepared according to the method described in U.S. Pat. No. 6,180,652 (Example 7).
  • the titled compound was prepared according to the method described in U.S. Pat. No. 5,045,552 (Example 33).
  • the drying was stopped and then, the amorphous substance of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt (9.4 kg, acetone: 130 ppm, HPLC purity: 99.3%) was obtained.
  • the powder X-ray diffraction pattern of the resulting amorphous substance was consistent with that of the freeze-dried product.
  • an acetone complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt (10 g: acetone content about 12%: 23 mmol) was placed in petri dish. The temperature of the dryer was set at 50° C., and air supply-drying was conducted for 48 hours (humidity in the room: 50%).
  • the amorphous substance of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt (9.0 g, acetone: 40 ppm, HPLC purity 99.8%) was obtained.
  • the powder X-ray diffraction pattern of the resulting amorphous substance was consistent with that of the freeze-dried product.
  • FIG. 1 shows a powder X-ray diffraction pattern as for an acetone complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt
  • FIG. 2 shows a powder X-ray diffraction pattern as for the freeze-dried product (Reference Example 2); and
  • FIG. 3 shows a powder X-ray diffraction pattern as for the heat-dried product (Example 1), respectively.
  • the powder X-ray diffraction pattern as for the resulting acetone complex denotes crystal structure. Furthermore, FIG. 7 shows a 1 H-NMR chart as for the acetonitrile complex; FIG. 8 shows a powder X-ray diffraction pattern as for the acetonitrile complex; and Table 1 shows diffraction angle and relative intensity in the powder X-ray diffraction pattern as for the acetonitrile complex; respectively.
  • the amorphous substance of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]-methylsulfinyl]-1H-benzimidazole sodium salt (4 g, acetonitrile: 4 ppm, HPLC purity: 99.7%) was obtained.
  • the powder X-ray diffraction pattern of the resulting amorphous substance was consistent with that of the freeze-dried product.
  • FIG. 9 shows a powder X-ray diffraction pattern as for the heat-dried product (Example 16).
  • the heat-drying could provide an amorphous substance having high uniformity.
  • the particle diameter and the specific surface of the heat-dried product were smaller than those of the freeze-dried product. Accordingly, it is believed that the heat-dried product has the water resistance superior to the freeze-dried product.
  • FIG. 6 shows the result of the thermal analysis.
  • the measurement result shows that at the temperature of 65.7° C. or more, the weight of the acetone complex of 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt starts to be decreased, and that at the temperature of 76.7° C. or more, the acetone starts to be effectively decreased.
  • the heat-drying method according to the present invention enables to stably obtain the amorphous substance of sulfoxide derivative (I) or the salt thereof in industrial scale from the solvated crystal of sulfoxide derivative (I) or the salt thereof Further, the drying method according to the present invention can make the particle size of the amorphous substance of sulfoxide derivative (I) or the salt thereof the same or similar size. Accordingly, the drying method according to the present invention, by comparison of the prior freeze-dry method, reduces the steps at the same time of greatly reducing the cost including time and energy, furthermore is believed to be preferred in light of environmental protection.

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MXPA05013316A (es) 2003-06-10 2006-03-17 Teva Pharma Proceso para preparar bencimidazoles 2[-(piridinil)metil]sulfinil-sustituidos y derivados clorados novedosos de pantoprazol.
US7829718B2 (en) 2004-08-06 2010-11-09 Eisai R&D Management Co., Ltd. Salts of benzimidazole derivative with amines and process for manufacturing the same
AR058440A1 (es) * 2005-08-02 2008-02-06 Medichem Sa Procesos para la produccion de rabeprazol sodico amorfo
IT1392813B1 (it) * 2009-02-06 2012-03-23 Dipharma Francis Srl Forme cristalline di dexlansoprazolo
EP2552903A1 (en) * 2010-03-31 2013-02-06 Ranbaxy Laboratories Limited Salts of dexlansoprazole and their preparation

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