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RU2386622C2 - Гетероароматические производные мочевины и их применение в качестве активаторов глюкокиназы - Google Patents

Гетероароматические производные мочевины и их применение в качестве активаторов глюкокиназы Download PDF

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RU2386622C2
RU2386622C2 RU2006122209/04A RU2006122209A RU2386622C2 RU 2386622 C2 RU2386622 C2 RU 2386622C2 RU 2006122209/04 A RU2006122209/04 A RU 2006122209/04A RU 2006122209 A RU2006122209 A RU 2006122209A RU 2386622 C2 RU2386622 C2 RU 2386622C2
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alkyl
independently selected
nitrogen atom
optionally substituted
compound according
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RU2386622C9 (ru
RU2006122209A (ru
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Энтони МЮРРЕЙ (DK)
Энтони Мюррей
Йеспер ЛАУ (DK)
Йеспер ЛАУ
Лон ЙЕППЕСЕН (DK)
Лон ЙЕППЕСЕН
Майкл АНКЕРСЕН (DK)
Майкл АНКЕРСЕН
Пер ВЕДСЁ (DK)
Пер ВЕДСЁ
Жан Мари ЛУНДБЕК (DK)
Жан Мари ЛУНДБЕК
Марит КРИСТИАНСЕН (DK)
Марит КРИСТИАНСЕН
Мария Кармен ВАЛСАРСЕ-ЛОПЕС (SE)
Мария Кармен ВАЛСАРСЕ-ЛОПЕС
Дхарма Рао ПОЛИСЕТТИ (US)
Дхарма Рао Полисетти
Говиндан СУБРАМАНИАН (US)
Говиндан Субраманиан
Роберт Карл ЭНДРЮС (US)
Роберт Карл Эндрюс
Даниель П. КРИСТЕН (US)
Даниель П. КРИСТЕН
Джереми Т. КУПЕР (US)
Джереми Т. КУПЕР
Калпати Чидамбаресваран САНТОШ (US)
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Abstract

Изобретение относится к соединениям общей формулы (I) и к их фармацевтически приемлемым солям, оптическим изомерам или их смеси в качестве активаторов глюкокиназы. Соединения могут найти применение для лечения и профилактики заболеваний, опосредованных низкой активностью глюкокиназы, таких как диабет типа 2. В общей формуле (I)
Figure 00000352
где R1 представляет собой С3-8-циклоалкил, С3-8-циклоалкенил, 6-членный гетероциклил с 1 атомом азота, конденсированный фенил-С3-8-циклоалкил, каждый из которых возможно замещен одним или двумя заместителями R3, R4, R5 и R6; R2 представляет собой С3-8-циклоалкил, 5-6-членный гетероциклил с 1-2 гетероатомами, выбранными из N, O или S, каждый из которых возможно замещен одним или двумя заместителями R30, R31, R32 и R33, и R3, R4, R5, R6, R30, R31, R32 и R33 независимо выбраны из группы, состоящей из - галогена, гидрокси, оксо, -CF3; либо -NR10R11; либо C1-6-алкила, фенила, C1-6-алкокси, С1-6-алкил-С(O)-O-C1-6-алкила, каждый из которых возможно замещен одним заместителем, независимо выбранным из R12; либо -C(O)-R27, -S(O)2-R27; либо два заместителя, выбранные из R3, R4, R5 и R6 или R30, R31, R32 и R33, присоединенные к одному и тому же атому или к соседним атомам, вместе образуют радикал -O-(СН2)2-O-; R10 и R11 независимо представляют собой водород, C1-6-алкил, -С(O)-С1-6-алкил, -С(O)-O-С1-6-алкил, -S(O)2-С1-6-алкил; R27 представляет собой C1-6-алкил, C1-6-алкокси, С3-8-циклоалкил, С3-8-циклоалкил-С1-6-алкил, фенил, фенил-С1-6-алкил, 5-6-членный гетероарил с 1-2 гетероатомами, выбранными из N или S, 6-членный гетероарил-C1-6-алкил с 1 атомом азота, 6-членный гетероциклил-С1-6-алкил с 1-2 гетероатомами, выбранными из N или О, R10R11-N-С1-6-алкил, каждый из которых возможно замещен одним заместителем, независимо выбранным из R12; R12 представляет собой галоген, -CF3, C1-6-алкокси, -NR10R11; А представляет собой 5-9-членный гетероарил с 1-3 гетероатомами, выбранными из N, О или S, который возможно замещен одним или двумя заместителями, независимо выбранным из R7, R8 и R9; R7, R8 и R9 независимо выбраны из галогена, циано, -CF3; либо C1-6-алкила, С2-6-алкенила, C1-6-алкокси, C1-6-алкилтио, -С(O)-O-С1-6-алкила, формила, -С1-6-алкил-С(O)-O-С1-6-алкила, -С1-6-алкил-O-С(O)-С1-6-алкила или гидрокси-С1-6-алкила, каждый из которых возможно замещен одним заместителем, независимо выбранным из R16; либо фенила, 5-членный гетероарил-С1-6-алкилтио с 2-4 атомами азота фенилтио, 5-6-членный гетероарилтио с 1-2 атомами азота, каждый из которых возможно замещен на арильной или гетероарильной части одним или двумя заместителями, независимо выбранным из R17; либо С3-8-циклоалкила; либо 6-членного гетероциклила с 2 атомами азота, 5-7-членного гетероциклил-С1-6-алкилтио с 1-2 гетероатомами, выбранными из N или О, каждый из которых возможно замещен одним заместителем, независимо выбранным из R16; либо C1-6-алкил-NR19R20, -S(O)2-R21 или -S(O)2-NR19R20; либо -C(O)NR22R23; R16, R17 и R18 независимо представляют собой C1-6-алкил, карбокси, -С(O)-O-С1-6-алкил, -NR19R20, -C(O)NR19R20; R19 и R20 независимо представляют собой водород, C1-6-алкил, фенил, 5-членный гетероарил с 2 гетероатомами, выбранными из N или S, 6-членный гетероциклил с 1 атомом азота, -С(O)-O-C1-6-алкил или -S(O)2-С1-6-алкил, каждый из которых возможно замещен одним заместителем, независимо выбранным из R24; либо R19 и R20 вместе с атомом азота, к которому они присоединены, образуют 5-7-членное гетероциклическое кольцо с указанным атомом азота, где это гетероциклическое кольцо возможно содержит один дополнительный гетероатом, выбранный из азота, кислорода и серы, где это гетероциклическое кольцо возможно замещено одним заместителем, независимо выбранным из R24; R21 выбран из С2-6-алкенила; либо R22 и R23 независимо выбраны из водорода, -С1-6-алкил-С(O)-O-С1-6-алкила, -C1-6-алкил-S(O)2-C1-6-алкила, С3-8-циклоалкила; либо R22 и R23 вместе с атомом азота, к которому они присоединены, образуют 6-членное гетероциклическое кольцо с указанным атомом азота, где это гетероциклическое кольцо возможно замещено одним заместителем, независимо выбранным из R24; R24 представляет собой оксо, C1-6-алкил, карбокси-С1-6-алкил, 6-членный гетероциклил с 1 атомом азота, -NH-S(O)2R28 или -S(O)2R28, где каждая циклическая группировка возможно замещена одним заместителем, независимо выбранным из R29; R28 представляет собой C1-6-алкил, -С1-6-алкил-С(O)-O-С1-6-алкил или -NH(СН3)2; R29 представляет собой C1-6-алкил. 1 н. и 20 з.п. ф-лы, 1 табл.

Description

Текст описания приведен в факсимильном виде.
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Claims (21)

1. Соединение общей формулы (I)
Figure 00000309

где R1 представляет собой С3-8-циклоалкил, С3-8-циклоалкенил, 6-членный гетероциклил с 1 атомом азота, конденсированный фенил-С3-8-циклоалкил, каждый из которых возможно замещен одним или двумя заместителями R3, R4, R5 и R6;
R2 представляет собой С3-8-циклоалкил, 5-6-членный гетероциклил с 1-2 гетероатомами, выбранными из N, O или S, каждый из которых возможно замещен одним или двумя заместителями R30, R31, R32 и R33, и
R3, R4, R5, R6, R30, R31, R32 и R33 независимо выбраны из группы, состоящей из
галогена, гидрокси, оксо, -CF3; либо
- NR10R11; либо -C1-6-алкила, фенила, С1-6-алкокси, С1-6-алкил-С(O)-O-С1-6-алкила, каждый из которых возможно замещен одним заместителем, независимо выбранным из R12; либо -C(O)-R27, -S(O)2-R27; либо два заместителя, выбранные из R3, R4, R5 и R6 или R30, R31, R32 и R33, присоединенные к одному и тому же атому или к соседним атомам, вместе образуют радикал -O-(СН2)2-O-;
R10 и R11 независимо представляют собой водород, C1-6-алкил, -С(O)-С1-6-алкил, -С(O)-O-C1-6-алкил, -S(O)2-С1-6-алкил;
R27 представляет собой C1-6-алкил, C1-6-алкокси, С3-8-циклоалкил, С3-8-циклоалкил-С1-6-алкил, фенил, фенил-С1-6-алкил, 5-6-членный гетероарил с 1-2 гетероатомами, выбранными из N или S, 6-членный гетероарил-С1-6-алкил с 1 атомом азота, 6-членный гетероциклил-С1-6-алкил с 1-2 гетероатомами, выбранными из N или О, R10R11-N-C1-6-алкил, каждый из которых возможно замещен одним заместителем, независимо выбранным из R12;
R12 представляет собой галоген, -CF3, C1-6-алкокси, -NR10R11;
А представляет собой 5-9-членный гетероарил с 1-3 гетероатомами, выбранными из N, О или S, который возможно замещен одним или двумя заместителями, независимо выбранными из R7, R8 и R9;
R7, R8 и R9 независимо выбраны из галогена, циано, -CF3; либо -C1-6-алкила, С2-6-алкенила, C1-6-алкокси, C1-6-алкилтио, -С(O)-O-С1-6-алкила, формила, -С1-6-алкил-С(O)-O-С1-6-алкила, -С1-6-алкил-O-С(O)-С1-6-алкила или гидрокси-С1-6-алкила, каждый из которых возможно замещен одним заместителем, независимо выбранным из R16; либо фенила, 5-членный гетероарил-С1-6-алкилтио с 2-4 атомами азота фенилтио, 5-6-членный гетероарилтио с 1-2 атомами азота, каждый из которых возможно замещен на арильной или гетероарильной части одним или двумя заместителями, независимо выбранными из R17; либо - С3-8-циклоалкила; либо - 6-членного гетероциклила с 2 атомами азота, 5-7-членного гетероциклил-С1-6-алкилтио с 1-2 гетероатомами, выбранными из N или О, каждый из которых возможно замещен одним заместителем, независимо выбранным из R16; либо
- C1-6-алкил-NR19R20, -S(O)2-R21 или -S(O)2-NR19R20; либо -C(O)NR22R23;
R16, R17 и R18 независимо представляют собой C1-6-алкил, карбокси, -С(O)-O-С1-6-алкил, -NR19R20, -C(O)NR19R20;
R19 и R20 независимо представляют собой водород, C1-6-алкил, фенил, 5-членный гетероарил с 2 гетероатомами, выбранными из N или S, 6-членный гетероциклил с 1 атомом азота, -С(O)-O-С1-6-алкил или -S(O)2-С1-6-алкил, каждый из которых возможно замещен одним заместителем, независимо выбранным из R24; либо R19 и R20 вместе с атомом азота, к которому они присоединены, образуют 5-7-членное гетероциклическое кольцо с указанным атомом азота, где это гетероциклическое кольцо возможно содержит один дополнительный гетероатом, выбранный из азота, кислорода и серы, где это гетероциклическое кольцо возможно замещено одним заместителем, независимо выбранным из R24;
R21 выбран из
-С2-6-алкенила; либо
R22 и R23 независимо выбраны из водорода, -С1-6-алкил-С(O)-O-С1-6-алкила, -C1-6-алкил-S(O)2-С1-6-алкила, С3-8-циклоалкила; либо R22 и R23 вместе с атомом азота, к которому они присоединены, образуют 6-членное гетероциклическое кольцо с указанным атомом азота, где это гетероциклическое кольцо возможно замещено одним заместителем, независимо выбранным из R24;
R24 представляет собой оксо, C1-6-алкил, карбокси-С1-6-алкил, 6-членный гетероциклил с 1 атомом азота, -NH-S(O)2R28 или -S(O)2R28, где каждая циклическая группировка возможно замещена одним заместителем, независимо выбранным из R29;
R28 представляет собой C1-6-алкил, -С1-6-алкил-С(O)-O-С1-6-алкил или -N(CH3)2;
R29 представляет собой C1-6-алкил;
а также любая его соль с фармацевтически приемлемой кислотой или основанием или любой оптический изомер или смесь оптических изомеров, включая рацемическую смесь.
2. Соединение по п.1, где R1 выбран из
Figure 00000310
,
Figure 00000311
,
Figure 00000312
,
Figure 00000313
,
Figure 00000314
,
Figure 00000315
,
Figure 00000316
или
Figure 00000317
3. Соединение по п.2, где R1 выбран из
Figure 00000318
,
Figure 00000319
Figure 00000320
,
Figure 00000321
,
Figure 00000322
,
Figure 00000323
,
Figure 00000324
,
Figure 00000315
,
Figure 00000325
или
Figure 00000326
4. Соединение по п.1, где R2 выбран из
Figure 00000327
,
Figure 00000328
,
Figure 00000329
,
Figure 00000330
,
Figure 00000331

Figure 00000332
,
Figure 00000333
,
Figure 00000334
,
Figure 00000335
или
Figure 00000336
5. Соединение по п.4, где R2 выбран из
Figure 00000318
,
Figure 00000337
,
Figure 00000338
,
Figure 00000339
,
Figure 00000340
,
Figure 00000341

Figure 00000342
,
Figure 00000343
,
Figure 00000344
,
Figure 00000345
,
Figure 00000335
или
Figure 00000336
6. Соединение по п.1, где R1 и R2 оба представляют собой циклогексил.
7. Соединение по п.1, где R1 представляет собой
Figure 00000323

и R2 представляет собой циклогексил.
8. Соединение по п.1, где R3, R4, R5, R6, R30, R31, R32 и R33 независимо выбраны из группы, состоящей из
галогена, -CF3; либо метила, этила, пропила, изопропила, бутила, трет-бутила, фенила, метокси, этокси, пропокси, каждый из которых возможно замещен одним заместителем, независимо выбранным из R12; либо -C(O)-R27 или -S(O)2-R27.
9. Соединение по п.8, где R3, R4, R5, R6, R30, R31, R32 и R33 независимо выбраны из группы, состоящей из F, Cl, -CF3, метила, этила, пропила, изопропила, бутила, трет-бутила, метокси, этокси, пропокси, -C(O)-R27 или -S(O)2-R27.
10. Соединение по п.1, где R10 и R11 независимо представляют собой водород, метил, этил, пропил, -С(O)-СН3, -С(O)-СН2СН3, -S(O)2СН3.
11. Соединение по п.10, где R10 и R11 независимо представляют собой водород, метил, этил, -С(O)-СН3, -S(O)2СН3.
12. Соединение по п.10, где R27 представляет собой метил, этил, пропил, н-бутил, изобутил, циклопропил, циклопентил, циклопропилметил, фенил или пиридил, тиофен, имидазол или тиазол.
13. Соединение по п.1, где R12 представляет собой галоген, -CF3.
14. Соединение по п.1, где А представляет собой
Figure 00000346
,
Figure 00000347
,
Figure 00000348
, ,
Figure 00000350
или
Figure 00000351
15. Соединение по п.1, где R7, R8 и R9 независимо выбраны из Cl, F, Br, -CF3, -S-СН3, -S-СН2СН3, -S-СН2СН2СН3, метила, этила, метокси, этокси, -СН2-С(O)-O-СН2СН3, -С(O)-O-СН3, или -С(O)-O-СН2СН3, каждый из которых возможно замещен одним заместителем, независимо выбранным из R16; или гетероарилтио, где гетероарил представляет собой пиридил или имидазолил, каждый возможно замещенный на гетероарильной части одним или двумя заместителями, независимо выбранным из R17, или гетероциклил-С1-6-алкилтио, где гетероциклил представляет собой пирролидинил, пиперидил, пиперазинил или морфолинил, каждый из которых возможно замещен одним заместителем, независимо выбранным из R16.
16. Соединение по п.1, где R16, R17 и R18 независимо представляют собой метил, этил, пропил, карбокси, -С(O)-O-СН3, -С(O)-O-СН2СН3, -C(O)-O-CH2CH2CH3.
17. Соединение по п.1, где R16, R17 и R18 независимо представляют собой C1-6-алкил, -NR19R20, -С(O)-O-С1-6-алкил или -C(O)NR19R20.
18. Соединение по п.1, где R19 и R20 независимо представляют собой водород, метил, этил или пропил, либо R19 и R20 вместе с атомом азота, к которому они присоединены, образуют 5-7-членное гетероциклическое кольцо с указанным атомом азота, где это гетероциклическое кольцо представляет собой пирролидил, пиперидил; где это гетероциклическое кольцо возможно замещено одним заместителем, независимо выбранным из R24.
19. Соединение по п.1, где R22 и R23 вместе с атомом азота, к которому они присоединены, образуют 6-членное гетероциклическое кольцо с указанным атомом азота, где это гетероциклическое кольцо представляет собой пиперидил; причем это гетероциклическое кольцо возможно замещено одним заместителем, независимо выбранным из R24.
20. Соединение по п.1, где R24 представляет собой оксо, С1-6-алкил, карбокси-С1-6-алкил, 6-членный гетероциклил с 1 атомом азота или -S(O)2R28, и где каждая циклическая группировка возможно замещена одним заместителем, независимо выбранным из R29.
21. Соединение по п.1, где R28 представляет собой C1-6-алкил, -С1-6-алкил-С(O)-O-С1-6-алкил или -N(CH3)2.
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