RU2007143507A - Производные фенилацетилена, обладающие сродством к рецептору mglur 5 - Google Patents

Производные фенилацетилена, обладающие сродством к рецептору mglur 5 Download PDF

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RU2007143507A
RU2007143507A RU2007143507/04A RU2007143507A RU2007143507A RU 2007143507 A RU2007143507 A RU 2007143507A RU 2007143507/04 A RU2007143507/04 A RU 2007143507/04A RU 2007143507 A RU2007143507 A RU 2007143507A RU 2007143507 A RU2007143507 A RU 2007143507A
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compound
formula
alkyl
free base
hydrogen
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RU2007143507/04A
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Ральф ГЛАТТАР (DE)
Ральф ГЛАТТАР
Томас Й. ТРОКСЛЕР (CH)
Томас Й. ТРОКСЛЕР
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Новартис АГ (CH)
Новартис Аг
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  • Thiazole And Isothizaole Compounds (AREA)

Abstract

1. Соединение формулы (I) ! ! в которой ! R1 обозначает водород или С1-С4алкил и ! R2 обозначает незамещенный или замещенный гетероцикл, или ! R1 обозначает водород или С1-С4алкил и ! R2 обозначает арил или замещенный арил, или ! R1 и R2 совместно с атомом азота образуют незамещенный или замещенный гетероцикл; ! R3 обозначает (С1-С4)алкил, (С1-С4)алкоксигруппу, трифторметил, галоген, цианогруппу, нитрогруппу, -СНО, -СОО(С1-С4)алкил, -СО(С1-С4)алкил; ! n равно 0, 1, 2, 3, 4 или 5; ! R4 обозначает ОН и ! R5 и R6 обозначают Н или С1-С4алкил, или ! R4 и R5 образуют связь и ! R6 обозначает Н или С1-С4алкил, или ! R4 и R6 образуют связь и ! R5 обозначает Н или С1-С4алкил, ! в форме свободного основания или соли присоединения с кислотой. ! 2. Соединение формулы (I') ! ! в которой R1, R2, R3 являются такими, как определено в п.1. ! 3. Соединение формулы (II) ! ! в которой R6, R5, R3, n являются такими, как определено в п.1. ! 4. Способ получения соединения формулы (I) по п.1 или его соли, который включает стадии ! а) получения соединения формулы (I), в которой i) R4 обозначает гидроксигруппу, ! R1 обозначает водород или С1-С4алкил и R2 обозначает незамещенный или замещенный гетероцикл или ii) R1 обозначает водород или С1-С4алкил и R2 обозначает арил или замещенный арил, с помощью восстановительного аминирования соединения формулы (II) ! ! в которой R6, R5, R3, n являются такими, как определено выше, соединением формулы (III) ! ! в которой R1 и R2 являются такими, как определено выше, или ! b) получения соединения формулы (I), в которой R4 обозначает гидроксигруппу, R1 и R2 совместно с атомом азота образуют незамещенный или замещенный гетероцикл, с помощью циклоконденсации соединения формулы (IV) ! ! или ! с) получения соединения формулы (I), в которо

Claims (10)

1. Соединение формулы (I)
Figure 00000001
в которой
R1 обозначает водород или С1-С4алкил и
R2 обозначает незамещенный или замещенный гетероцикл, или
R1 обозначает водород или С1-С4алкил и
R2 обозначает арил или замещенный арил, или
R1 и R2 совместно с атомом азота образуют незамещенный или замещенный гетероцикл;
R3 обозначает (С1-С4)алкил, (С1-С4)алкоксигруппу, трифторметил, галоген, цианогруппу, нитрогруппу, -СНО, -СОО(С1-С4)алкил, -СО(С1-С4)алкил;
n равно 0, 1, 2, 3, 4 или 5;
R4 обозначает ОН и
R5 и R6 обозначают Н или С1-С4алкил, или
R4 и R5 образуют связь и
R6 обозначает Н или С1-С4алкил, или
R4 и R6 образуют связь и
R5 обозначает Н или С1-С4алкил,
в форме свободного основания или соли присоединения с кислотой.
2. Соединение формулы (I')
Figure 00000002
в которой R1, R2, R3 являются такими, как определено в п.1.
3. Соединение формулы (II)
Figure 00000003
в которой R6, R5, R3, n являются такими, как определено в п.1.
4. Способ получения соединения формулы (I) по п.1 или его соли, который включает стадии
а) получения соединения формулы (I), в которой i) R4 обозначает гидроксигруппу,
R1 обозначает водород или С1-С4алкил и R2 обозначает незамещенный или замещенный гетероцикл или ii) R1 обозначает водород или С1-С4алкил и R2 обозначает арил или замещенный арил, с помощью восстановительного аминирования соединения формулы (II)
Figure 00000003
в которой R6, R5, R3, n являются такими, как определено выше, соединением формулы (III)
Figure 00000004
в которой R1 и R2 являются такими, как определено выше, или
b) получения соединения формулы (I), в которой R4 обозначает гидроксигруппу, R1 и R2 совместно с атомом азота образуют незамещенный или замещенный гетероцикл, с помощью циклоконденсации соединения формулы (IV)
Figure 00000005
или
с) получения соединения формулы (I), в которой R4 обозначает гидроксигруппу, R1 и R2 совместно с атомом азота образуют незамещенный или замещенный гетероцикл, с помощью восстановительного алкилирования соединения формулы (V)
Figure 00000006
в которой R6, R5, R2, R1 являются такими, как определено выше, соединением формулы (VI)
Figure 00000007
в которой R3 и n являются такими, как определено выше, или
d) получения соединения формулы (I), в которой i) R4 и R5 образуют связь и R6 обозначает водород или С1-С4алкил или ii) в которой R4 и R6 образуют связь и R5 обозначает водород, с помощью дегидратации соединения формулы (I), в которой R4 обозначает гидроксигруппу, R5 и R6 обозначают водород или С1-С4алкил;
и выделения полученного соединения формулы (I) в форме свободного основания или соли присоединения с кислотой.
5. Соединение по п.1 в форме свободного основания или фармацевтически приемлемой соли присоединения с кислотой, предназначенное для применения в качестве фармацевтического средства.
6. Соединение по п.1 в форме свободного основания или фармацевтически приемлемой соли присоединения с кислотой, предназначенное для применения для предупреждения, лечения или задержки прогрессирования нарушений, связанных с нерегулярностью глутаматергической передачи сигнала, нарушений желудочно-кишечного тракта и мочевых путей, и нервной системы, полностью или частично опосредуемых mGluR5.
7. Фармацевтическая композиция, включающая соединение по п.1 в форме свободного основания или фармацевтически приемлемой соли присоединения с кислотой совместно с фармацевтическим носителем или разбавителем.
8. Применение соединения по п.1 в форме свободного основания или фармацевтически приемлемой соли присоединения с кислотой для предупреждения, лечения или задержки прогрессирования нарушений, связанных с нерегулярностью глутаматергической передачи сигнала, нарушений желудочно-кишечного тракта и мочевых путей, и нервной системы, полностью или частично опосредуемых mGluR5.
9. Применение соединения по п.1 в форме свободного основания или фармацевтически приемлемой соли присоединения с кислотой для приготовления фармацевтической композиции, предназначенной для предупреждения, лечения или задержки прогрессирования нарушений, связанных с нерегулярностью глутаматергической передачи сигнала, нарушений желудочно-кишечного тракта и мочевых путей, и нервной системы, полностью или частично опосредуемых mGluR5.
10. Способ лечения нарушений, связанных с нерегулярностью глутаматергической передачи сигнала, и нарушений нервной системы, полностью или частично опосредуемых mGluR5, способ включает введение субъекту, нуждающемуся в таком лечении, терапевтически эффективного количества соединения по п.1 в форме свободного основания или фармацевтически приемлемой соли присоединения с кислотой.
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