RU2007108536A - Соединения, которые усиливают рецептор глутамата, и их применение в медицине - Google Patents

Соединения, которые усиливают рецептор глутамата, и их применение в медицине Download PDF

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RU2007108536A
RU2007108536A RU2007108536/04A RU2007108536A RU2007108536A RU 2007108536 A RU2007108536 A RU 2007108536A RU 2007108536/04 A RU2007108536/04 A RU 2007108536/04A RU 2007108536 A RU2007108536 A RU 2007108536A RU 2007108536 A RU2007108536 A RU 2007108536A
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propanesulfonamide
inden
dihydro
pyridinyl
alkyl
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RU2007108536/04A
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RU2403242C2 (ru
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Дэниел Маркус БРЭДЛИ (GB)
Дэниел Маркус Брэдли
Кевин Майкл ТЬЮЛИЗ (GB)
Кевин Майкл Тьюлиз
Саймон Эдвард УОРД (GB)
Саймон Эдвард Уорд
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Глэксо Груп Лимитед (GB)
Глэксо Груп Лимитед
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Priority claimed from GB0417708A external-priority patent/GB0417708D0/en
Priority claimed from GB0508473A external-priority patent/GB0508473D0/en
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Claims (21)

1. Соединение формулы (I), его фармацевтически приемлемая соль, сольват или пролекарство
Figure 00000001
где R1 означает С1-6алкил, галогенС1-6алкил, С2-6алкенил, амино, моноС1-4алкиламино или диС1-4алкиламино;
R2 и R3, которые могут быть одинаковыми или разными, представляют водород, галоген, С1-6алкил, галогенС1-6алкил, С1-4алкокси, галогенС1-4алкокси, циано, амино, моноС1-4алкиламино или диС1-4алкиламино;
каждый R4, которые могут быть одинаковыми или разными, означает С1-6алкил, галоген, галогенС1-6алкил, С1-4алкокси, галогенС1-4алкокси, циано, нитро, амино, моноС1-4алкиламино или диС1-4алкиламино;
p означает 0, 1 или 2;
n означает 1 или 2;
R5 и R6, которые могут быть одинаковыми или разными, представляют водород, галоген, С1-6алкил, галогенС1-6алкил, С1-4алкокси, галогенС1-4алкокси, циано, амино, моноС1-4алкиламино или диС1-4алкиламино, и
Het означает тиенил, пиридил, пиримидинил, пиридазинил, пиразинил, имидазолил, пиразолил, пирролил, хинолил, тиазолил или фурил, каждый из которых может быть замещенным одной или несколькими группами, независимо выбранными из списка, состоящего из С1-6алкила, С1-6алкокси, ацетила, галогена, галогенС1-6алкила, циано, нитро, амино, моноС1-4алкиламино и диС1-4алкиламино.
2. Соединение по п.1, где R1 представляет С1-6алкил.
3. Соединение по п.1 или п.2, где R2 и R3, которые могут быть одинаковыми или разными, представляют водород, галоген или С1-6алкил.
4. Соединение по п.1, где p означает 0.
5. Соединение по п.1, где каждый R4, которые могут быть одинаковыми или разными, представляет С1-6алкил или галоген.
6. Соединение по п.1, где R5 и R6, которые могут быть одинаковыми или разными, представляют водород, галоген или С1-6алкил.
7. Соединение по п.1, где n означает 1.
8. Соединение по п.1, где Het представляет пиридил (например, 3-пиридил), пиримидинил (например, 5-пиримидинил, 2-пиримидинил), тиенил (например, 3-тиенил, 2-тиенил), пиридазинил (например, 3-пиридазинил), имидазолил (например, 1H-4-имидазолил) или пиразолил (например, 1H-4-пиразолил), каждый из которых является необязательно замещенным одной-тремя группами, независимо выбранными из группы, состоящей из С1-6алкила (такого как метил), ацетила, циано, галогена (такого как фтор или хлор), галогенС1-6алкила (такого как CF3) и С1-6алкокси (такой как метокси).
9. Соединение по п.1, имеющее общую формулу (IA), или его фармацевтически приемлемая соль, сольват или пролекарство:
Figure 00000002
где R1, R2, R3, R4, R5, R6, n, p и Het имеют значения, указанные в любом из пп.1-8.
10. Соединение по п.1, имеющее общую формулу (Ic), или его фармацевтически приемлемая соль, сольват или пролекарство
Figure 00000003
где Het и R1 имеют значения, указанные в любом из пп.1-8.
11. Соединение по п.1, которым является
N-[5-(2-фтор-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(6-фтор-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(5-пиримидинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(3-тиенил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(2-тиенил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(4-метил-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(2,6-диметил-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(6-циано-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(5-ацетил-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(5-циано-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(5-фтор-2-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(4-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(2-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(6-фтор-2-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(2-метил-4-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(6-метил-3-пиридазинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(2-пиримидинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(3-фтор-4-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(6-фтор-2-метил-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(1H-имидазол-4-ил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(1,3,5-триметил-1H-пиразол-4-ил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(6-метил-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(3-метил-2-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(5-метил-2-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(6-хлор-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-{5-[6-(метилокси)-3-пиридинил]-2,3-дигидро-1H-инден-2-ил}-2-пропансульфонамид
N-[5-(5-хлор-2-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[5-(2-хлор-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-{(2S)-5-[6-(трифторметил)-3-пиридинил]-2,3-дигидро-1H-инден-2-ил}-2-пропансульфонамид
N-[(2S)-5-(5-хлор-2-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-{(2S)-5-[6-(трифторметил)-2-пиридинил]-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[(2S)-5-(5-метил-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[(2S)-5-(5-фтор-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[(2S)-5-(2-фтор-6-метил-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид
N-[(2S)-5-(2,6-дифтор-3-пиридинил)-2,3-дигидро-1H-инден-2-ил]-2-пропансульфонамид или их фармацевтически приемлемые соли, сольваты и пролекарства.
12. Способ получения соединения по п.1, включающий
взаимодействие соединения формулы (II):
Figure 00000004
где R1-R6, n и p имеют значения, указанные в п.1, и X представляет уходящую группу; с производным бороновой кислоты или сложного эфира бороновой кислоты (бороната) соединения формулы (III):
Het-B(OR)2
(III)
где Het имеет значения, указанные в п.1, и R представляет водород, алкил (такой как С1-6алкил) или две группы R образуют кольцо (такое как 5- или 6-членное кольцо);
и необязательно с последующим
удалением какой-либо защитной группы(групп); и/или
образованием соли; и/или
превращением одного соединения формулы (I) в другое соединение формулы (I).
13. Способ получения соединения по п.1, включающий
взаимодействие соединения бороновой кислоты или сложного эфира бороновой кислоты (бороната) формулы (IV)
Figure 00000005
где R1-R6, n и p имеют значения, указанные в п.1, и R представляет водород, алкил (такой как С1-6алкил) или две группы R образуют кольцо (такое как 5- или 6-членное кольцо), с соединением формулы (V):
Het-X
(V)
где Het имеет значения, указанные в п.1, и X представляет уходящую группу;
и необязательно с последующим
удалением какой-либо защитной группы(групп); и/или
образованием соли; и/или
превращением одного соединения формулы (I) в другое соединение формулы (I).
14. Фармацевтическая композиция, содержащая соединение по любому из пп.1-11 и фармацевтически приемлемый носитель или разбавитель.
15. Применение соединения по любому из пп.1-11 в производстве лекарственного средства для лечения или профилактики болезни или состояния, вызванного снижением или дисбалансом функции рецептора глутамата у млекопитающего.
16. Применение по п.15, где болезнь является шизофренией.
17. Соединение по любому из пп.1-11 для лечения или профилактики болезни или состояния, вызванного снижением или дисбалансом функции рецептора глутамата у млекопитающего.
18. Соединение по п.17, где болезнь является шизофренией.
19. Соединение по любому из пп.1-11, пригодное в качестве лекарственного средства.
20. Способ лечения и профилактики болезни или состояния, вызванного снижением или дисбалансом функции рецептора глутамата у млекопитающего, включающий введение эффективного количества соединения по любому из пп.1-11.
21. Способ по п.20, где болезнь является шизофренией.
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