RU2007121697A - Гидроксибензоатные соли метаникотиновых соединений - Google Patents
Гидроксибензоатные соли метаникотиновых соединений Download PDFInfo
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Abstract
1. Соль, полученная как продукт реакции (4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амина и гидроксибензойной кислоты, где гидроксибензойная кислота имеет формулугде гидроксигруппа может присутствовать в орто-, мета- или пара-положении относительно группы карбоновой кислоты, Z представляет собой неводородный заместитель, выбранный из группы, состоящей из алкила, замещенного алкила, алкенила, замещенного алкенила, гетероциклила, замещенного гетероциклила, циклоалкила, замещенного циклоалкила, арила, замещенного арила, алкиларила, замещенного алкиларила, арилалкила, замещенного арилалкила, F, Cl, Br, I, NR'R", CF, CN, NO, CR', SH, SCH, N, SOCH, OR', (CR'R")OR', O-(CR'R")CR', SR', C(=O)NR'R", NR'C(=O)R", C(=O)R', C(=O)OR', OC(=O)R', (CR'R")OCHCR', (CR'R")C(=O)R', (CR'R")C(CHCH)OR', O(CR'R")C(=O)OR', (CR'R")C(=O)NR'R", (CR'R")NR'R", CH=CHR', OC(=O)NR'R" и NR'C(=O)OR",где q представляет собой целое число, имеющее значение от 1 до 6, и R' и R", каждый независимо представляет собой водород, Cалкил, циклоалкил, неароматическое гетероциклическое кольцо, где гетероатом гетероциклического фрагмента отделен от какого-либо другого атома азота, кислорода или серы, по меньшей мере, двумя атомами углерода, или группу, содержащую ароматическую группу, выбранную из группы, состоящей из пиридинила, хинолинила, пиримидинила, фуранила, фенила и бензила, где любой из вышеуказанных может быть подходящим образом замещен, по меньшей мере, одной группой заместителя, такой как заместители алкил, гидроксил, алкоксил, галоген или амино,и j представляет собой число, имеющее значение от нуля до трех, представляющее количество заместителей Z, которое может присутствовать в кольце,где молярное отношение (4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амина к гидрокси
Claims (11)
1. Соль, полученная как продукт реакции (4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амина и гидроксибензойной кислоты, где гидроксибензойная кислота имеет формулу
где гидроксигруппа может присутствовать в орто-, мета- или пара-положении относительно группы карбоновой кислоты, Z представляет собой неводородный заместитель, выбранный из группы, состоящей из алкила, замещенного алкила, алкенила, замещенного алкенила, гетероциклила, замещенного гетероциклила, циклоалкила, замещенного циклоалкила, арила, замещенного арила, алкиларила, замещенного алкиларила, арилалкила, замещенного арилалкила, F, Cl, Br, I, NR'R", CF3, CN, NO2, C2R', SH, SCH3, N3, SO2CH3, OR', (CR'R")qOR', O-(CR'R")qC2R', SR', C(=O)NR'R", NR'C(=O)R", C(=O)R', C(=O)OR', OC(=O)R', (CR'R")qOCH2C2R', (CR'R")qC(=O)R', (CR'R")qC2(CHCH3)OR', O(CR'R")qC(=O)OR', (CR'R")qC(=O)NR'R", (CR'R")qNR'R", CH=CHR', OC(=O)NR'R" и NR'C(=O)OR",
где q представляет собой целое число, имеющее значение от 1 до 6, и R' и R", каждый независимо представляет собой водород, C1-10 алкил, циклоалкил, неароматическое гетероциклическое кольцо, где гетероатом гетероциклического фрагмента отделен от какого-либо другого атома азота, кислорода или серы, по меньшей мере, двумя атомами углерода, или группу, содержащую ароматическую группу, выбранную из группы, состоящей из пиридинила, хинолинила, пиримидинила, фуранила, фенила и бензила, где любой из вышеуказанных может быть подходящим образом замещен, по меньшей мере, одной группой заместителя, такой как заместители алкил, гидроксил, алкоксил, галоген или амино,
и j представляет собой число, имеющее значение от нуля до трех, представляющее количество заместителей Z, которое может присутствовать в кольце,
где молярное отношение (4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амина к гидроксибензойной кислоте находится в интервале от 1:2 до 2:1.
2. Соль по п.1, где гидроксибензойная кислота представляет собой о-, м- или п-гидроксибензойную кислоту.
3. Соль по п.1, где гидроксибензойная кислота представляет собой гентизиновую кислоту (2,5-дигидроксибензойную кислоту).
4. Соединение, обозначенное как п-гидроксибензоат (2S)-(4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амина.
5. Соль по п.1, где (4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амин представляет собой (2S)-(4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амин.
6. Фармацевтическая композиция, содержащая соль по любому из пп.1-5 вместе с фармацевтически приемлемым носителем.
7. Способ лечения расстройства ЦНС, включающий введение субъекту, нуждающемуся в этом, эффективного количества композиции, содержащей соль по любому из пп.1-5, где указанную соль необязательно можно вводить вместе с фармацевтически приемлемым носителем.
8. Способ получения (2S)-(4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амина или его соответствующей гидроксибензоатной соли,
включающий стадии
a) осуществления реакции сочетания Гека между 3-галоген-5-изопропоксипиридином и соединением формулы (S)-CH2=CH-CH2-CH(CH3)-N(CH3)(pg), где pg представляет собой защитную группу для амина, и
b) снятия защиты с аминогруппы, или
c) осуществления реакции сочетания Гека между 3-галоген-5-изопропоксипиридином и соединением формулы (R)-CH2=CH-CH2-CH(CH3)-OH и
d) преобразования группы OH в группу NHCH3,
для получения смеси соединений, содержащей (2S)-(4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амин, соответствующее Z-метаникотиновое соединение и другие изомеры,
e) образования гидроксибензоатной соли путем взаимодействия указанной смеси с гидроксибензойной кислотой формулы
где гидроксигруппа может присутствовать в орто-, мета- или пара-положении относительно группы карбоновой кислоты, Z представляет собой неводородный заместитель, выбранный из группы, состоящей из алкила, замещенного алкила, алкенила, замещенного алкенила, гетероциклила, замещенного гетероциклила, циклоалкила, замещенного циклоалкила, арила, замещенного арила, алкиларила, замещенного алкиларила, арилалкила, замещенного арилалкила, F, Cl, Br, I, NR'R", CF3, CN, NO2, C2R', SH, SCH3, N3, SO2CH3, OR', (CR'R")qOR', O-(CR'R")qC2R', SR', C(=O)NR'R", NR'C(=O)R", C(=O)R', C(=O)OR', OC(=O)R', (CR'R")qOCH2C2R', (CR'R")qC(=O)R', (CR'R")qC2(CHCH3)OR', O(CR'R")qC(=O)OR', (CR'R")qC(=O)NR'R", (CR'R")qNR'R", CH=CHR', OC(=O)NR'R" и NR'C(=O)OR",
где q представляет собой целое число, имеющее значение от 1 до 6, и R' и R", каждый независимо представляет собой водород, C1-10 алкил, циклоалкил, неароматическое гетероциклическое кольцо, где гетероатом гетероциклического фрагмента отделен от какого-либо другого атома азота, кислорода или серы, по меньшей мере, двумя атомами углерода, или группу, содержащую ароматическую группу, выбранную из группы, состоящей из пиридинила, хинолинила, пиримидинила, фуранила, фенила и бензила, где любой из вышеуказанных может быть подходящим образом замещен, по меньшей мере, одной группой заместителя, такой как заместители алкил, гидроксил, алкоксил, галоген или амино,
и j представляет собой число, имеющее значение от нуля до трех, представляющее количество заместителей Z, которое может присутствовать в кольце,
где молярное отношение E-метаникотина к гидроксибензойной кислоте находится в интервале от 1:2 до 2:1,
f) выделения гидроксибензоатной соли (2S)-(4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амина и
g) необязательно, преобразования гидроксибензоатной соли (2S)-(4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амина в (2S)-(4E)-N-метил-5-(5-изопропокси-3-пиридинил)-4-пентен-2-амин.
9. Способ по п.8, где гидроксибензойная кислота представляет собой о-, м- или п-гидроксибензойную кислоту.
10. Способ по п.8 или 9, где гидроксибензоатую соль преобразуют в другую фармацевтически приемлемую солевую форму.
11. Применение композиции, содержащей соль по любому из пп.1-5 для получения лекарственного средства, полезного для лечения расстройства ЦНС.
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