RU2440330C2 - ПРОИЗВОДНЫЕ 4-(2-АМИНО-1-ГИДРОКСИЭТИЛ)ФЕНОЛА, КАК АГОНИСТЫ β2 АДРЕНЕРГИЧЕСКОГО РЕЦЕПТОРА - Google Patents

ПРОИЗВОДНЫЕ 4-(2-АМИНО-1-ГИДРОКСИЭТИЛ)ФЕНОЛА, КАК АГОНИСТЫ β2 АДРЕНЕРГИЧЕСКОГО РЕЦЕПТОРА Download PDF

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RU2440330C2
RU2440330C2 RU2007146798/04A RU2007146798A RU2440330C2 RU 2440330 C2 RU2440330 C2 RU 2440330C2 RU 2007146798/04 A RU2007146798/04 A RU 2007146798/04A RU 2007146798 A RU2007146798 A RU 2007146798A RU 2440330 C2 RU2440330 C2 RU 2440330C2
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amino
hexyl
hydroxyethyl
difluoro
hydroxymethyl
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Карлос ПУИГ-ДУРАН (ES)
Карлос Пуиг-Дуран
Мария-Исабель КРЕСПО-КРЕСПО (ES)
Мария-Исабель КРЕСПО-КРЕСПО
Хулио-Сесар КАСТРО-ПАЛОМИНО-ЛАРИЯ (ES)
Хулио-Сесар КАСТРО-ПАЛОМИНО-ЛАРИЯ
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Сильвия ГВАЛ-РОИГ
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Abstract

Изобретение относится к новым соединениям формулы (I), а также к их фармацевтически приемлемым солям или стереоизомерам, обладающим активностью в отношении β2 адренергического рецептора. В формуле (I)
Figure 00000106
R1 обозначает группу, выбранную из -СН2ОН, -NHC(O)H, и R2 обозначает атом водорода; или R1 вместе с R2 образуют группу -NH-C(O)-CH=CH-, где атом азота связан с атомом углерода фенильного кольца, содержащего R1, и атом углерода связан с атомом углерода фенильного кольца, содержащего R2; R3 выбран из группы, включающей атомы водорода и галогена, или обозначает группу, выбранную из -NH-CO-NH2, гидантоиновой группы, С1-С4алкила и С1-С4алкоксигруппы; R4 выбран из группы, включающей атомы водорода, атомы галогена и С1-С4алкильные группы; n, р и q независимо равны 0, 1, 2, 3 или 4; m и s независимо равны 0, 1, 2 или 3; r равно 0, 1 или 2; при условиях, что по меньшей мере одно из m и r не равно 0, сумма n+m+p+q+r+s равна 7, 8, 9, 10, 11, 12 или 13, сумма q+r+s равна 2, 3, 4, 5 или 6. Изобретение относится также к фармацевтической композиции, способам лечения и модуляции. 4 н. и 16 з.п. ф-лы.

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Claims (20)

1. Соединение формулы (I)
Figure 00000105

в которой R1 обозначает группу, выбранную из группы, включающей -СН2ОН, -NHC(O)H, и
R2 обозначает атом водорода; или
R1 вместе с R2 образуют группу -NH-C(O)-CH=CH-, где атом азота связан с атомом углерода фенильного кольца, содержащего R1, и атом углерода связан с атомом углерода фенильного кольца, содержащего R2;
R3 выбран из группы, включающей атомы водорода и галогена, или обозначает группу, выбранную из группы, включающей -NH-CO-NH2, гидантоиновую группу, С1-С4алкил и С1-С4алкоксигруппу;
R4 выбран из группы, включающей атомы водорода, атомы галогена и С1-С4алкильные группы;
n, р и q независимо равны 0, 1, 2, 3 или 4;
m и s независимо равны 0, 1, 2 или 3;
r равно 0, 1 или 2;
при условиях, что:
по меньшей мере одно из m и r не равно 0,
сумма n+m+p+q+r+s равна 7, 8, 9, 10, 11, 12 или 13,
сумма q+r+s равна 2, 3, 4, 5 или 6,
или его фармацевтически приемлемая соль или стереоизомер.
2. Соединение по п.1, в котором по меньшей мере одно из m и r равно 1.
3. Соединение по п.2, в котором сумма m+r равна 1.
4. Соединение по п.1, в котором сумма n+m+p+q+r+s равна 8, 9 или 10.
5. Соединение по п.1, в котором сумма q+r+s равна 2, 3 или 4.
6. Соединение по п.1, в котором s равно 0 или 1.
7. Соединение по п.1, в котором сумма n+р равна 4, 5 или 6.
8. Соединение по п.1, в котором сумма q+s равна 1, 2, 3 или 4.
9. Соединение по п.1, в котором R3 обозначает атом водорода, атом галогена или метильную группу.
10. Соединение по п.9, в котором R3 обозначает атом хлора или фтора.
11. Соединение по п.9, в котором R3 обозначает метильную группу.
12. Соединение по п.1, в котором R4 обозначает атом водорода.
13. Соединение по п.1, в котором R4 обозначает атом хлора.
14. Соединение по п.1, выбранное из группы, включающей:
(R,S)-4-(2-{[6-(2,2-дифтор-4-фенилбутокси)гексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)фенол,
(R,S)-4-(2-{[6-(2,2-дифтор-2-фенилэтокси)гексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)фенол,
(R,S)-4-(2-{[4,4-дифтор-6-(4-фенилбутокси)гексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)фенол,
(R,S)-4-(2-{[6-(4,4-дифтор-4-фенилбутокси)гексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)фенол,
(R,S)-5-(2-{[6-(2,2-дифтор-2-фенилэтокси)гексил]амино}-1-гидроксиэтил)-8-гидроксихинолин-2(1H)-он,
(R,S)-4-[2-({6-[2,2-дифтор-2-(3-метилфенил)этокси]гексил}амино)-1-гидроксиэтил]-2-(гидроксиметил)фенол,
4-((1R)-2-{[6-(2,2-дифтор-2-фенилэтокси)гексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)фенол,
(R,S)-2-(гидроксиметил)-4-(1-гидрокси-2-{[4,4,5,5-тетрафтор-6-(3-фенил-пропокси)гексил]амино}этил)фенол,
(R,S)-[5-(2-{[6-(2,2-дифтор-2-фенилэтокси)гексил]амино}-1-гидроксиэтил)-2-гидроксифенил]формамид,
(R,S)-4-[2-({6-[2-(3-бромфенил)-2,2-дифторэтокси]гексил}амино)-1-гидроксиэтил]-2-(гидроксиметил)фенол,
(R,S)-N-[3-(1,1-дифтор-2-{[6-({2-гидрокси-2-[4-гидрокси-3-(гидроксиметил)фенил]этил}амино)гексил]окси}этил)фенил]мочевину,
(R,S)-3-[3-(1,1-дифтор-2-{[6-({2-гидрокси-2-[4-гидрокси-3-(гидроксиметил)фенил]этил}амино)гексил]окси}этил)фенил]имидазолидин-2,4-дион,
(R,S)-4-[2-({6-[2,2-дифтор-2-(3-метоксифенил)этокси]гексил}амино)-1-гидроксиэтил]-2-(гидроксиметил)фенол,
5-((1R)-2-{[6-(2,2-дифтор-2-фенилэтокси)гексил]амино}-1-гидроксиэтил)-8-гидроксихинолин-2(1H)-он,
4-((1R)-2-{[4,4-дифтор-6-(4-фенилбутокси)гексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)фенол,
(R,S)-4-(2-{[6-(3,3-дифтор-3-фенилпропокси)гексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)фенол,
(R)-4-(2-{[6-(2,2-дифтор-2-фенилэтокси)-4,4-дифторгексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)фенол,
гидрохлорид (R,S)-4-(2-{[6-(2,2-дифтор-3-фенилпропокси)гексил]амино}-1-гидроксиэтил)-2-(гидроксиметил)фенола,
и их фармацевтически приемлемые соли.
15. Фармацевтическая композиция, обладающая активностью в отношении β2 адренергического рецептора, включающая терапевтически эффективное количество соединения по любому из пп.1-14 и фармацевтически приемлемый носитель.
16. Фармацевтическая композиция по п.15 в форме, пригодной для введения путем ингаляции.
17. Способ лечения заболевания или патологического состояния, связанного с активностью β2 адренергического рецептора, включающий введение терапевтически эффективного количества фармацевтической композиции по п.15.
18. Способ по п.17, в котором заболеванием или патологическим состоянием является заболевание легких.
19. Способ по п.18, в котором заболеванием легких является астма или хроническое обструктивное заболевание легких.
20. Способ модуляции активности β2 адренергического рецептора, включающий стимулирование β2 адренергического рецептора модулирующим количеством соединения по любому из пп.1-14.
RU2007146798/04A 2005-05-20 2006-05-17 ПРОИЗВОДНЫЕ 4-(2-АМИНО-1-ГИДРОКСИЭТИЛ)ФЕНОЛА, КАК АГОНИСТЫ β2 АДРЕНЕРГИЧЕСКОГО РЕЦЕПТОРА RU2440330C2 (ru)

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