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RU2008129129A - Пиперазины и пиперидины в качестве mglur5 потенцирующих средств - Google Patents

Пиперазины и пиперидины в качестве mglur5 потенцирующих средств Download PDF

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RU2008129129A
RU2008129129A RU2008129129/04A RU2008129129A RU2008129129A RU 2008129129 A RU2008129129 A RU 2008129129A RU 2008129129/04 A RU2008129129/04 A RU 2008129129/04A RU 2008129129 A RU2008129129 A RU 2008129129A RU 2008129129 A RU2008129129 A RU 2008129129A
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piperazin
ethanone
phenyl
benzyloxy
ylmethoxy
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RU2008129129/04A
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Абдельмалик СЛАССИ (CA)
Абдельмалик Сласси
Метвин ИСААК (CA)
Метвин Исаак
Джалай АРОРА (CA)
Джалай Арора
Дин Дж. БРАУН (US)
Дин Дж. БРАУН
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Астразенека Аб (Se)
Астразенека Аб
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Abstract

1. Соединение формулы I или его фармацевтически приемлемая соль или сольват ! ! где Аr1 выбран из группы, состоящей из фенила и пиридила, которые могут быть замещены заместителями в количестве вплоть до 4, независимо выбранными из группы, состоящей из алкила, галогено, галогеноалкила и СN; ! Аr2 выбран из группы, состоящей из фенила и гетероарила, которые могут быть замещены заместителями в количестве вплоть до 4, независимо выбранными из группы, состоящей из алкила, галогено и галогеноалкила; ! А выбран из группы, состоящей из С(O), C(S) и S(O)2; ! Х выбран из группы, состоящей из О и S; ! Y выбран из группы, состоящей из С и N; ! m выбран из группы, состоящей из 1 и 2; ! n выбран из группы, состоящей из 1 и 2; ! R1 выбран из группы, состоящей из Н и алкила, ! R2, R3, R4 и R5 независимо выбраны из группы, состоящей из Н и алкила; ! при условии, что соединение не представляет собой ! 1-[(бензилокси)ацетил]-4-(4-хлорфенил)пиперазин, ! 1-[(бензилокси)ацетил]-4-(2-метоксифенил)пиперазин, ! 1-[(бензилокси)ацетил]-4-(4-метоксифенил)пиперазин, ! 1-[(бензилокси)ацетил]-4-(3-хлорфенил)пиперазин или ! 2-бензилокси-1-[4-(3-метил-пиридин-2-ил)-пиперазин-1-ил]-этанон. ! 2. Соединение по п.1, где Аr1 представляет собой фенил. ! 3. Соединение по п.2, где Аr2 выбран из группы, состоящей из фенила, тиенила, тиазолила и пиридила. ! 4. Соединение по п.3, где Аr2 выбран из группы, состоящей из тиенила и пиридила. ! 5. Соединение, выбранное из группы, состоящей из ! 2-бензилокси-1-[4-(4-фторфенил)-пиперазин-1-ил]-этанона, ! 2-бензилокси-1-[4-(2-хлор-5-трифторметил-фенил)-пиперазин-1-ил]-этанона, ! 2-бензилокси-1-[4-(3,5-дихлор-пиридин-4-ил)-пиперазин-1-ил]-этанона, ! 2-бензилокси-1-[4-(5-хлор-2-метил-фенил)-пиперазин-1-ил]-этанона, ! 4-[4-(2-бензилоксиацет

Claims (12)

1. Соединение формулы I или его фармацевтически приемлемая соль или сольват
Figure 00000001
где Аr1 выбран из группы, состоящей из фенила и пиридила, которые могут быть замещены заместителями в количестве вплоть до 4, независимо выбранными из группы, состоящей из алкила, галогено, галогеноалкила и СN;
Аr2 выбран из группы, состоящей из фенила и гетероарила, которые могут быть замещены заместителями в количестве вплоть до 4, независимо выбранными из группы, состоящей из алкила, галогено и галогеноалкила;
А выбран из группы, состоящей из С(O), C(S) и S(O)2;
Х выбран из группы, состоящей из О и S;
Y выбран из группы, состоящей из С и N;
m выбран из группы, состоящей из 1 и 2;
n выбран из группы, состоящей из 1 и 2;
R1 выбран из группы, состоящей из Н и алкила,
R2, R3, R4 и R5 независимо выбраны из группы, состоящей из Н и алкила;
при условии, что соединение не представляет собой
1-[(бензилокси)ацетил]-4-(4-хлорфенил)пиперазин,
1-[(бензилокси)ацетил]-4-(2-метоксифенил)пиперазин,
1-[(бензилокси)ацетил]-4-(4-метоксифенил)пиперазин,
1-[(бензилокси)ацетил]-4-(3-хлорфенил)пиперазин или
2-бензилокси-1-[4-(3-метил-пиридин-2-ил)-пиперазин-1-ил]-этанон.
2. Соединение по п.1, где Аr1 представляет собой фенил.
3. Соединение по п.2, где Аr2 выбран из группы, состоящей из фенила, тиенила, тиазолила и пиридила.
4. Соединение по п.3, где Аr2 выбран из группы, состоящей из тиенила и пиридила.
5. Соединение, выбранное из группы, состоящей из
2-бензилокси-1-[4-(4-фторфенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(2-хлор-5-трифторметил-фенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(3,5-дихлор-пиридин-4-ил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(5-хлор-2-метил-фенил)-пиперазин-1-ил]-этанона,
4-[4-(2-бензилоксиацетил)-пиперазин-1-ил]-бензонитрила,
2-бензилокси-1-[4-(4-трифторметил-фенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(3,5-дихлорметилфенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(2,3-дихлорфенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(2,4-дихлорфенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-(4-пара-толил-пиперазин-1-ил)-этанона,
2-бензилокси-1-[4-(2-хлорфенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-(4-фенил-пиперазин-1-ил)-этанона,
2-бензилокси-1-(4-пиридин-2-ил-пиперазин-1-ил)-этанона,
2-бензилокси-1-(3-метил-4-фенил-пиперазин-1-ил)-этанона,
2-бензилокси-1-[4-(2,4-дифтор-фенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(2-трифторметил-фенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(5-этинил-пиридин-2-ил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(2-фторфенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(5-трифторметил-пиридин-2-ил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(6-метил-пиридин-2-ил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(2,5-дихлорфенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(3,4-дихлор-фенил)-пиперазин-1-ил]-этанона,
2-[4-(2-бензилокси-ацетил)-пиперазин-1-ил]-никотинонитрила,
1-[4-(2,4-дифтор-фенил)-пиперазин-1-ил]-2-(4-фтор-бензилокси)-пропан-1-она,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(4-фтор-бензилокси)-пропан-1-она,
1-[4-(2,4-дифтор-фенил)-пиперазин-1-ил]-2-(3-метил-3Н-имидазол-4-илметокси)-пропан-1-она,
1-[4-(2,4-хлор-фенил)-пиперазин-1-ил]-2-(3-метил-3Н-имидазол-4-илметокси)-пропан-1-она,
1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-2-(пиридин-2-илметилокси)-этанона,
1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-2-(пиридин-4-илметилокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(пиридин-4-илметилокси)-этанона,
2-бензилокси-1-[4-(4-фтор-2-хлор-фенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(пиридин-2-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(пиридин-3-илметокси)-этанона,
1-[4-(2,4-дифтор-фенил)-пиперазин-1-ил]-2-(пиридин-2-илметокси)-этанона,
1-[4-(2,4-дифтор-фенил)-пиперазин-1-ил]-2-(пиридин-3-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(пиридин-4-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(3-фтор-бензилокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(4-фтор-бензилокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(2-фтор-бензилокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(2,3-дифтор-бензилокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(2,4-дифтор-бензилокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(2,5-дифтор-бензилокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(2,6-дифтор-бензилокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(3,4-дифтор-бензилокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(3,5-дифтор-бензилокси)-этанона,
1-[4-(2,4-дифтор-фенил)-пиперазин-1-ил]-2-(2-фтор-бензилокси)-этанона,
1-[4-(2,4-дифтор-фенил)-пиперазин-1-ил]-2-(4-фтор-бензилокси)-этанона,
2-(2,4-дифтор-бензилокси)-1-[4-(2,4-дифтор-фенил)-пиперазин-1-ил]-этанона,
2-бензилокси-1-[4-(2,4-дихлор-фенил)-3,6-дигидро-2Н-пиридин-1-ил]-этанона,
2-бензилокси-1-[4-(2,4-дихлор-фенил)-[1,4]диазепан-1-ил]-этанона,
1-[4-(3-хлор-пиридин-4-ил)-пиперазин-1-ил]-2-(пиридин-4-илметокси)-этанона,
1-[4-(5-хлор-пиридин-2-ил)-пиперазин-1-ил]-2-(пиридин-4-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-2-метил-пиперазин-1-ил]-2-(пиридин-4-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(1-пиридин-4-ил-этокси)-этанона,
1-[4-(2,4-дихлор-фенил)-3-метил-пиперазин-1-ил]-2-(пиридин-4-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-2-метил-пиперазин-1-ил]-2-(пиридин-2-илметокси)-этанона,
1-[(R)-4-(2,4-дихлор-фенил)-2-метил-пиперазин-1-ил]-2-(пиридин-4-илметокси)-этанона,
1-[(S)-4-(2,4-дихлор-фенил)-2-метил-пиперазин-1-ил]-2-(пиридин-4-илметокси)-этанона,
1-[4-(4-хлор-фенил)-пиперазин-1-ил]-2-(пиридин-2-илметокси)-этанона,
1-[4-(4-хлор-фенил)-пиперазин-1-ил]-2-(пиридин-4-илметокси)-этанона,
1-[4-(5-метил-пиридин-2-ил)-пиперазин-1-ил]-2-(пиридин-2-илметокси)-этанона,
1-[4-(5-фтор-пиридин-2-ил)-пиперазин-1-ил]-2-(пиридин-4-илметокси)-этанона,
1-[4-(2-хлор-4-фтор-фенил)-2-метил-пиперазин-1-ил]-2-(пиридин-4-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(3-метил-пиридин-4-илметокси)-этанона,
1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-2-(3-фтор-пиридин-4-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(3-фтор-пиридин-4-илметокси)-этанона,
1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-2-(тиазол-4-илметокси)-этанона,
1-[4-(5-хлор-пиридин-2-ил)-пиперазин-1-ил]-2-(тиазол-4-илметокси)-этанона,
1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-2-(тиазол-5-илметокси)-этанона,
1-[4-(5-хлор-пиридин-2-ил)-пиперазин-1-ил]-2-(тиазол-5-илметокси)-этанона,
1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-2-(тиазол-2-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(тиазол-5-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(тиазол-2-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(2-метил-тиазол-4-илметокси)-этанона,
1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-2-(2-метил-тиазол-4-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(4-метил-тиазол-5-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(пиразин-2-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(пиримидин-4-илметокси)-этанона,
1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-2-(пиримидин-4-илметокси)-этанона,
1-[4-(5-хлор-пиридин-2-ил)-пиперазин-1-ил]-2-(пиримидин-4-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(тиофен-2-илметокси)-этанона,
1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-2-(тиофен-2-илметокси)-этанона,
1-[4-(5-хлор-пиридин-2-ил)-пиперазин-1-ил]-2-(тиофен-2-илметокси)-этанона,
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(тиофен-3-илметокси)-этанона,
1-[4-(2-хлор-4-фтор-фенил)-пиперазин-1-ил]-2-(тиофен-3-илметокси)-этанона,
1-[4-(5-хлор-пиридин-2-ил)-пиперазин-1-ил]-2-(тиофен-3-илметокси)-этанона и
1-[4-(2,4-дихлор-фенил)-пиперазин-1-ил]-2-(тиазол-4-илметокси)-этанона.
6. Фармацевтическая композиция, включающая соединение по любому из пп.1-4 и фармацевтически приемлемый носитель или эксципиент.
7. Соединение по любому из пп.1-4 для применения в качестве лекарственного средства.
8. Применение соединения по любому из пп.1-4 в производстве лекарственного средства для терапии неврологических и психиатрических расстройств, ассоциированных с глутаматной дисфункцией.
9. Применение по п.8, где указанное расстройство представляет собой шизофрению.
10. Способ лечения или предупреждения неврологических и психиатрических расстройств, ассоциированных с глутаматной дисфункцией, у животного, нуждающегося в таком лечении, включающий стадию введения указанному животному терапевтически эффективного количества соединения по любому из пп.1-4.
11. Способ лечения или предупреждения неврологических и психиатрических расстройств, ассоциированных с глутаматной дисфункцией, у животного, нуждающегося в таком лечении, включающий стадию введения указанному животному терапевтически эффективного количества фармацевтической композиции по п.6.
12. Способ по п.9 или 10, где указанное расстройство представляет собой шизофрению.
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