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RU2003108745A - METHOD FOR OBTAINING OLANZAPINE HYDRATES AND TRANSFORMING THEM IN CRYSTAL FORMS OF OLANZAPINE - Google Patents

METHOD FOR OBTAINING OLANZAPINE HYDRATES AND TRANSFORMING THEM IN CRYSTAL FORMS OF OLANZAPINE Download PDF

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RU2003108745A
RU2003108745A RU2003108745/04A RU2003108745A RU2003108745A RU 2003108745 A RU2003108745 A RU 2003108745A RU 2003108745/04 A RU2003108745/04 A RU 2003108745/04A RU 2003108745 A RU2003108745 A RU 2003108745A RU 2003108745 A RU2003108745 A RU 2003108745A
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methyl
olanzapine
thieno
hydrochloride
benzodiazepine
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RU2003108745/04A
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Бучи Редди РЕГУРИ (IN)
Бучи Редди РЕГУРИ
Рамеш ЧАККА (IN)
Рамеш ЧАККА
Роберт КОПРОВСКИ (US)
Роберт КОПРОВСКИ
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Др. Редди`З Лабораториз Лтд. (In)
Др. Редди`З Лабораториз Лтд.
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Publication of RU2003108745A publication Critical patent/RU2003108745A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
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  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Psychiatry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (21)

1. Соединение, которое представляет собой моногидрат-1 оланзапина.1. The compound, which is olanzapine monohydrate-1. 2. Соединение, которое представляет собой дигидрат-1 оланзапина.2. A compound that is olanzapine dihydrate-1. 3. Соединение, которое представляет собой моногидрат-1 оланзапина, имеющее следующую рентгеновскую дифракцию на порошке:3. The compound, which is olanzapine monohydrate-1, having the following x-ray powder diffraction: значение dd value I/I0 I / I 0 10.17610.176 100100 6.89956.8995 77 6.35676.3567 1212 6.17146.1714 11eleven 4.87564.8756 5151 4.72624.7262 2222 4.59054.5905 3434 4.49374.4937 77 4.43154.4315 13thirteen 4.34144.3414 1010 4.14114.1411 66 3.91743.9174 9nine 3.86693.8669 2323 3.78573.7857 2626 3.64803.6480 9nine 3.57013.5701 15fifteen 3.44513.4451 33 3.25003.2500 44 3.20653.2065 44 2.96462.9646 55 2.87152.8715 33 2.85722.8572 33 2.68682.6868 33 2.67432.6743 33
4. Соединение, которое представляет собой дигидрат-1 оланзапина, имеющее следующую рентгеновскую дифракцию на порошке:4. A compound that is olanzapine dihydrate-1 having the following x-ray powder diffraction: значение dd value I/I0 I / I 0 9.99499.9949 100 100 9.68879.6887 77 7.04187.0418 22 6.41176.4117 22 6.24956.2495 77 6.12056.1205 66 5.45345.4534 66 5.23585.2358 22 4.82304.8230 3333 4.71624.7162 9nine 4.57174.5717 15fifteen 4.48474.4847 66 4,39244.3924 88 4.30804.3080 44 4.20704.2070 33 4.07354.0735 33 3.99743.9974 33 3.92423.9242 9nine 3.84383.8438 1212 3.76993.7699 9nine 3.73863.7386 13thirteen 3.68373.6837 33 3.65093.6509 44 3.60723.6072 55 3.52563.5256 11eleven 3.42423.4242 22 3.17733.1773 22 3.12073.1207 22 2.99172.9917 22 2.95692.9569 33 2.87332.8733 22 2.84832.8483 22 2.78952.7895 22
5. Способ получения моногидрата-1 оланзапина, включающий следующие стадии:5. A method of producing olanzapine monohydrate-1, comprising the following steps: a) кипячение с обратным холодильником смеси хлоргидрата 4-амино-2-метил-10Н-тиено-[2,3-b][1,5]бензодиазепина, N-метилпиперазина, диметилсульфоксида и толуола в течение 5-20 ч;a) refluxing a mixture of 4-amino-2-methyl-10H-thieno [2,3-b] [1,5] benzodiazepine hydrochloride, N-methylpiperazine, dimethyl sulfoxide and toluene hydrochloride for 5-20 hours; b) охлаждение смеси до температуры от 20 до 90°С;b) cooling the mixture to a temperature of from 20 to 90 ° C; c) добавление воды;c) adding water; d) охлаждение смеси до температуры от -5 до 25°С и перемешивание в течение 2-10 ч;d) cooling the mixture to a temperature of from -5 to 25 ° C and stirring for 2-10 hours; e) фильтрование смеси и промывание водой; иe) filtering the mixture and washing with water; and f) сушка при температуре от 30 до 50°С до постоянного веса.f) drying at a temperature of from 30 to 50 ° C to constant weight. 6. Способ по пункту 5, в котором соотношение количества хлоргидрата 4-амино-2-метил-10Н-тиено-[2,3-b][1,5]бензодиазепина и N-метилпиперазина составляет 1:2,0-8,4.6. The method according to paragraph 5, in which the ratio of the amount of 4-amino-2-methyl-10H-thieno [2,3-b] [1,5] benzodiazepine hydrochloride and N-methylpiperazine hydrochloride is 1: 2.0-8, 4. 7. Способ по пункту 5, в котором объем диметилсульфоксида представляет собой 2-8 кратные значения молей хлоргидрата 4-амино-2-метил-10Н-тиено-[2,3-b][1,5] бензодиазепина.7. The method according to paragraph 5, wherein the volume of dimethyl sulfoxide is 2-8 times the moles of 4-amino-2-methyl-10H-thieno [2,3-b] [1,5] benzodiazepine hydrochloride. 8. Способ по пункту 5, в котором объем толуола представляет собой 3-8 кратные значения молей хлоргидрата 4-амино-2-метил-10Н-тиено-[2,3-b][1,5]бензодиазепина и диметилсульфоксида.8. The method according to claim 5, wherein the toluene volume is 3-8 times the moles of 4-amino-2-methyl-10H-thieno [2,3-b] [1,5] benzodiazepine and dimethyl sulfoxide hydrochloride. 9. Способ получения дигидрата-1 оланзапина, включающий следующие стадии:9. A method of producing olanzapine dihydrate-1, comprising the following steps: a) кипячение с обратным холодильником смеси хлоргидрата 4-амино-2-метил-10Н-тиено-[2,3-b][1,5]бензодиазепина, N-метилпиперазина, диметилсульфоксида и толуола в течение 5 - 20 ч;a) refluxing a mixture of 4-amino-2-methyl-10H-thieno [2,3-b] [1,5] benzodiazepine hydrochloride, N-methylpiperazine, dimethyl sulfoxide and toluene hydrochloride for 5 to 20 hours; b) охлаждение смеси до температуры от 20 до 90°С;b) cooling the mixture to a temperature of from 20 to 90 ° C; c) добавление воды;c) adding water; d) охлаждение смеси до температуры от -5 до 25°С и перемешивание в течение 2-10 ч;d) cooling the mixture to a temperature of from -5 to 25 ° C and stirring for 2-10 hours; e) фильтрование смеси и промывание водой; иe) filtering the mixture and washing with water; and f) сушка при температуре окружающей среды до постоянного веса.f) drying at ambient temperature to constant weight. 10. Способ по пункту 9, в котором соотношение количества хлоргидрата 4-амино-2-метил-10Н-тиено-[2,3-b][1,5]бензодиазепина и N-метилпиперазина составляет 1:2,0-8,4.10. The method according to paragraph 9, in which the ratio of the amount of 4-amino-2-methyl-10H-thieno [2,3-b] [1,5] benzodiazepine hydrochloride and N-methylpiperazine hydrochloride is 1: 2.0-8, 4. 11. Способ по пункту 9, в котором объем диметилсульфоксида представляет собой 2-8 кратные значения молей хлоргидрата 4-амино-2-метил-10Н-тиено-[2,3-b][1,5]бензодиазепина.11. The method according to claim 9, wherein the volume of dimethyl sulfoxide is 2-8 times the moles of 4-amino-2-methyl-10H-thieno [2,3-b] [1,5] benzodiazepine hydrochloride. 12. Способ по пункту 9, в котором объем толуола представляет собой 3-8 кратные значения молей хлоргидрата 4-амино-2-метил-10Н-тиено-[2,3-b][1,5]бензодиазепина.12. The method of claim 9, wherein the toluene volume is 3-8 times the moles of 4-amino-2-methyl-10H-thieno [2,3-b] [1,5] benzodiazepine hydrochloride. 13. Способ получения формы-1 оланзапина из дигидрата-1 оланзапина, который включающий следующие стадии:13. A method of obtaining olanzapine form-1 from olanzapine dihydrate-1, which comprising the following steps: a) перемешивание 2-метил-4-(4-метил-1-пеперазинил)-10Н-тиено-[2,3-b][1,5]бензодиазепина (моногидрат-1 оланзапина) в дихлорметане при кипячении с обратным холодильником до получения прозрачного раствора;a) stirring 2-methyl-4- (4-methyl-1-peperazinyl) -10H-thieno [2,3-b] [1,5] benzodiazepine (olanzapine monohydrate-1) in dichloromethane under reflux to obtaining a clear solution; b) обработка раствора углем;b) treating the solution with coal; c) фильтрование смеси для получения фильтрата;c) filtering the mixture to obtain a filtrate; d) охлаждение фильтрата до температуры от 0 до 5°С;d) cooling the filtrate to a temperature of from 0 to 5 ° C; e) перемешивание в течение 60-90 мин;e) stirring for 60-90 minutes; f) фильтрование для получения твердого вещества, промывание и сушка при температуре от 60 до 70°С до получения постоянного веса.f) filtering to obtain a solid, washing and drying at a temperature of from 60 to 70 ° C until a constant weight is obtained. 14. Способ по пункту 13, где на этапе f) твердое вещество промывают дихлорметаном.14. The method of claim 13, wherein in step f), the solid is washed with dichloromethane. 15. Способ по пункту 13, в котором количество дихлорметана, использующегося на стадии а) имеет значение от 4,5 до 13 по объему/весу хлоргидрата 2-метил-4-(4-метил-1-15. The method according to claim 13, wherein the amount of dichloromethane used in step a) is from 4.5 to 13 by volume / weight of 2-methyl-4- (4-methyl-1- hydrochloride пеперазинил)-10Н-тиено-[2,3-b][1,5]бензодиазепина.peperazinyl) -10H-thieno [2,3-b] [1,5] benzodiazepine. 16. Способ получения формы-1 оланзапина из моногидрата-1 оланзапина, включающий следующие стадии:16. A method of obtaining olanzapine form-1 from olanzapine monohydrate-1, comprising the following steps: a) перемешивание 2-метил-4-(4-метил-1-пеперазинил)-10Н-тиено-[2,3-b][1,5]бензодиазепина в дихлорметане при кипячении с обратным холодильником до получения прозрачного раствора;a) stirring 2-methyl-4- (4-methyl-1-peperazinyl) -10H-thieno [2,3-b] [1,5] benzodiazepine in dichloromethane under reflux until a clear solution is obtained; b) обработка раствора углем;b) treating the solution with coal; c) фильтрование раствора для получения фильтрата;c) filtering the solution to obtain a filtrate; d) охлаждение фильтрата до температуры ниже от 0 до 5°С; иd) cooling the filtrate to a temperature below 0 to 5 ° C; and e) перемешивание в течение 60-90 мин,e) stirring for 60-90 minutes, f) отделение твердого вещества, промывание и сушка при температуре от 60 до 70°С до получения постоянного веса.f) separating the solid, washing and drying at a temperature of from 60 to 70 ° C until a constant weight is obtained. 17. Способ по пункту 16, в котором количество использующегося дихлорметана имеет значение от 4.5 до 13 по объему/весу хлоргидрата 2-метил-4-(4-метил-1-пиперазинил)-10Н-тиено-[2,3-b][1,5]бензодиазепина.17. The method according to paragraph 16, in which the amount of dichloromethane used is from 4.5 to 13 by volume / weight of 2-methyl-4- (4-methyl-1-piperazinyl) -10H-thieno [2,3-b] hydrochloride [1,5] benzodiazepine. 18. Способ по пункту 16, в котором на стадии f) твердое вещество промывают дихлорметаном.18. The method of claim 16, wherein in step f), the solid is washed with dichloromethane. 19. Способ получения формы-1 оланзапина из формы-2 оланзапина, включающий следующие этапы:19. A method of obtaining olanzapine form-1 from olanzapine form-2, comprising the following steps: a) перемешивание хлоргидрата 2-метил-10Н-тиено-[2,3-b][1,5]бензодиазепина (форма-2 оланзапина) в дихлорметане при кипячении с обратным холодильником до получения прозрачного раствора;a) stirring 2-methyl-10H-thieno [2,3-b] [1,5] benzodiazepine hydrochloride (form-2 olanzapine) in dichloromethane under reflux until a clear solution is obtained; b) фильтрование и охлаждение фильтрата до температуры от 0 до 5°С;b) filtering and cooling the filtrate to a temperature of from 0 to 5 ° C; c) перемешивание в течение 60-90 мин; иc) stirring for 60-90 minutes; and d) фильтрование для получения твердого вещества, промывание и сушка при температуре 60-70°С до получения постоянного веса.d) filtering to obtain a solid, washing and drying at a temperature of 60-70 ° C until a constant weight is obtained. 20. Способ по пункту 19, в котором количество использующегося дихлорметана имеет значение от 4,5 до 13 по объему/весу хлоргидрата 2-метил-10Н-тиено-[2,3-b][1,5]бензодиазепина.20. The method according to paragraph 19, in which the amount of dichloromethane used is from 4.5 to 13 by volume / weight of 2-methyl-10H-thieno [2,3-b] [1,5] benzodiazepine hydrochloride. 21. Способ по пункту 19, в котором на стадии d) твердое вещество промывают дихлорметаном.21. The method of claim 19, wherein in step d), the solid is washed with dichloromethane.
RU2003108745/04A 2000-08-31 2001-03-07 METHOD FOR OBTAINING OLANZAPINE HYDRATES AND TRANSFORMING THEM IN CRYSTAL FORMS OF OLANZAPINE RU2003108745A (en)

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