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RU2018120216A - TENELIGLIPTIN OXALATE SALTS AND THEIR SOLVATS, THEIR INTERMEDIATE COMPOUNDS, PRODUCTION METHOD AND MARKERS - Google Patents

TENELIGLIPTIN OXALATE SALTS AND THEIR SOLVATS, THEIR INTERMEDIATE COMPOUNDS, PRODUCTION METHOD AND MARKERS Download PDF

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RU2018120216A
RU2018120216A RU2018120216A RU2018120216A RU2018120216A RU 2018120216 A RU2018120216 A RU 2018120216A RU 2018120216 A RU2018120216 A RU 2018120216A RU 2018120216 A RU2018120216 A RU 2018120216A RU 2018120216 A RU2018120216 A RU 2018120216A
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ylcarbonyl
piperazin
thiazolidine
phenyl
methyl
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Махадев Кадам Суреш
Парсоттам Кансагра Бипин
Кантилал Кале Шрикришна
Бхаскар Бхируд Шекхар
Кумар Двиведи Раджеш
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Гленмарк Фармасьютикалс Лимитед
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Claims (20)

1. Оксалат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин 2-илкарбонил}тиазолидина и его сольваты.1. Oxalate of 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin 2-ylcarbonyl} thiazolidine and its solvates. 2. Оксалат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольваты по п. 1, отличающийся тем, что указанный сольват представляет собой n. гидрат, причем n равен от 1,0 до 4,0.2. Oxalate of 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine and its solvates according to claim 1, characterized in that said solvate is n. hydrate, where n is from 1.0 to 4.0. 3. Оксалат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольваты по п. 1, отличающийся тем, что представляет собой кристаллическую форму n. гидрата 2,5 оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина, причем n равен от 1,0 до 4,03. Oxalate of 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine and its solvates according to claim 1, characterized in that it is a crystalline form n. hydrate 2.5 oxalate 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine, where n is from 1.0 to 4.0
Figure 00000001
.
Figure 00000001
... 4. Оксалат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольваты по п. 3, отличающийся тем, что кристаллическая форма n. гидрата 2,5 оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина, причем n равен от 1,0 до 4,0, характеризуется диаграммой рентгеновской порошковой дифракции, содержащей пики отражения при 5,68°, 6,56°, 16,44°, 17,72°, 18,34°, 21,12°, 21,67°, 23,15°, 23,86°, 24,99°±0.2°
Figure 00000002
.4. Oxalate of 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine and its solvates according to claim 3, characterized in that the crystalline form n. hydrate 2.5 oxalate 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine, where n is from 1.0 to 4.0, characterized by an X-ray powder diffraction diagram containing reflection peaks at 5.68 °, 6.56 °, 16.44 °, 17.72 °, 18.34 °, 21.12 °, 21.67 °, 23.15 °, 23.86 °, 24.99 ° ± 0.2 °
Figure 00000002
... 5. Оксалат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольваты по п. 3, отличающийся тем, что кристаллическая форма n. гидрата 2,5 оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина, где n равен от 1,0 до 4,0, характеризуется термограммой дифференциальной сканирующей калориметрии (ДСК), имеющей эндотерму при 152,76°С и 169,68°С.5. Oxalate of 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine and its solvates according to claim 3, characterized in that the crystalline form n. hydrate 2.5 oxalate 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine, where n is from 1.0 to 4.0, characterized by a differential scanning calorimetry (DSC) thermogram having an endotherm at 152.76 ° C and 169.68 ° C. 6. Оксалат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольваты по п. 3, отличающийся тем, что кристаллическая форма n. гидрата 2,5 оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина, где n равен от 1,0 до 4,0, характеризуется пиками на спектре инфракрасного поглощения с Фурье-преобразованием (Фурье-ИК) при 3452,22, 3011,77, 2540,88, 1721,37, 1650,04, 1207,43, 922,34, 708,96, 477,35 см-1.6. Oxalate 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine and its solvates according to claim 3, characterized in that the crystalline form n. hydrate 2.5 oxalate 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine, where n is from 1.0 to 4.0, characterized by peaks in the infrared absorption spectrum with Fourier transform (FTIR) at 3452.22, 3011.77, 2540.88, 1721.37, 1650.04, 1207, 43, 922.34, 708.96, 477.35 cm -1 . 7. Оксалат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольваты по п. 1, отличающийся тем, что представляет собой кристаллическую форму n. гидрата 3,0 оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина, где n равен от 1,0 до 4,07. Oxalate of 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine and its solvates according to claim 1, characterized in that it is a crystalline form n. 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine oxalate hydrate, where n is from 1.0 to 4.0
Figure 00000003
.
Figure 00000003
... 8. Оксалат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольваты по п. 7, отличающийся тем, что кристаллическая форма n. гидрата 3,0 оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина, где n равен от 1,0 до 4,0, характеризуется диаграммой рентгеновской порошковой дифракции, содержащей пики отражения при 5,69°, 6,57°, 16,43°, 17,71°, 21,66°, 23,15°, 23,86°, 24,99°±0.2°
Figure 00000002
.8. Oxalate 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine and its solvates according to claim 7, characterized in that the crystalline form n. 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine oxalate hydrate, where n is from 1.0 to 4.0, characterized by an X-ray powder diffraction diagram containing reflection peaks at 5.69 °, 6.57 °, 16.43 °, 17.71 °, 21.66 °, 23.15 °, 23.86 °, 24.99 ° ± 0.2 °
Figure 00000002
... 9. Оксалат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольваты по п. 7, отличающийся тем, что кристаллическая форма n. гидрата 3,0 оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина, где n равен от 1,0 до 4,0, характеризуется пиками на спектре инфракрасного (ИК) поглощения при 3464,93, 3011,34, 2537,55, 1911,30, 1720,10, 1651,64, 1456,82, 1363,34, 1209,29, 922,88, 709,74, 475,21 см-1.9. Oxalate of 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine and its solvates according to claim 7, characterized in that the crystalline form n. 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine oxalate hydrate, where n is from 1.0 to 4.0, characterized by peaks in the infrared (IR) absorption spectrum at 3464.93, 3011.34, 2537.55, 1911.30, 1720.10, 1651.64, 1456.82, 1363.34, 1209.29, 922.88, 709.74, 475.21 cm -1 . 10. Оксалат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольваты по п. 1, имеющий чистоту по меньшей мере 99% и содержащий менее 1% по массе соединения Формулы (II)10. Oxalate of 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine and its solvates according to claim 1, having a purity of at least 99% and containing less than 1% by weight of a compound of Formula (II)
Figure 00000004
.
Figure 00000004
... 11. Способ получения оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольватов, включающий стадии:11. A method of obtaining oxalate 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine and its solvates, including the stages: (a) получения раствора 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина или его соли в растворителе, выбранном из воды, спирта, такого как метанол, галогенированного растворителя, такого как дихлорметан или их смеси;(a) preparing a solution of 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine, or its salts in a solvent selected from water, an alcohol such as methanol, a halogenated solvent such as dichloromethane, or mixtures thereof; (b) обработки раствора 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина или его соли, полученного на стадии (а), подходящим основанием;(b) treating a solution of 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine, or its salt obtained in stage (a) with a suitable base; (c) приведения в контакт раствора, полученного на стадии (а) или стадии (b), с подходящим источником оксалат-иона; и(c) contacting the solution obtained in step (a) or step (b) with a suitable source of oxalate ion; and (d) выделения оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина и его сольватов, полученных на стадии (с), где соль 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина, используемая на стадии (а), представляет собой дибензоил-L-тартрат 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина или его сольват.(d) isolating 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine oxalate, and its solvates obtained in step (c), where salt 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidine -2-ylcarbonyl} thiazolidine used in step (a) is dibenzoyl-L-tartrate 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazole-5- yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine or a solvate thereof. 12. Способ по п. 11, отличающийся тем, что приводит к образованию n. гидрата 2,5 оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина в кристаллической форме, где n равен от 1,0 до 4,0, или n. гидрата 3,0 оксалата 3-{(2S,4S)-4-[4-(3-метил-1-фенил-1Н-пиразол-5-ил)пиперазин-1-ил]пирролидин-2-илкарбонил}тиазолидина в кристаллической форме, где n равен от 1,0 до 4,0.12. The method according to claim 11, characterized in that it leads to the formation of n. hydrate 2.5 oxalate 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine c crystalline form, where n is from 1.0 to 4.0, or n. 3.0 oxalate hydrate 3 - {(2S, 4S) -4- [4- (3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-ylcarbonyl} thiazolidine c crystalline form, where n is from 1.0 to 4.0. 13. Способ по п. 11, отличающийся тем, что подходящий источник оксалат-иона выбран из группы, состоящей из щавелевой кислоты или ее гидрата, солей щелочных металлов щавелевой кислоты, таких как натриевая, калиевая, литиевая, магниевая и смешанная натриево-калиевая соль щавелевой кислоты, аммониевой соли щавелевой кислоты, а также кислых солей вышеперечисленных соединений, таких как гидрооксалат натрия, гидрооксалат калия, тетраоксалат калия и гидрооксалат аммония.13. The method according to claim 11, characterized in that the suitable source of oxalate ion is selected from the group consisting of oxalic acid or its hydrate, alkali metal salts of oxalic acid such as sodium, potassium, lithium, magnesium and mixed sodium-potassium salt oxalic acid, ammonium salt of oxalic acid, as well as acidic salts of the above compounds, such as sodium hydroxalate, potassium hydroxalate, potassium tetraoxalate and ammonium hydroxalate.
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