RU2436780C2 - Производные 5-фенилтиазола и их применение в качестве ингибиторов рi3 киназы - Google Patents

Производные 5-фенилтиазола и их применение в качестве ингибиторов рi3 киназы Download PDF

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RU2436780C2
RU2436780C2 RU2009132712/04A RU2009132712A RU2436780C2 RU 2436780 C2 RU2436780 C2 RU 2436780C2 RU 2009132712/04 A RU2009132712/04 A RU 2009132712/04A RU 2009132712 A RU2009132712 A RU 2009132712A RU 2436780 C2 RU2436780 C2 RU 2436780C2
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Айан БРЮС (GB)
Айан Брюс
Питер ФИНАН (GB)
Питер ФИНАН
Кэтрин ЛЕБЛАНК (GB)
Кэтрин ЛЕБЛАНК
Клайв МАККАРТНИ (CH)
Клайв МАККАРТНИ
Льюис УАЙТХЕД (US)
Льюис Уайтхед
Никола Элейн ПРЕСС (GB)
Никола Элейн ПРЕСС
Грэм Чарлз БЛУМФИЛД (GB)
Грэм Чарлз Блумфилд
Джуди ХЕЙЛЕР (GB)
Джуди ХЕЙЛЕР
Луиса КЕРМАН (US)
Луиса КЕРМАН
Мриналини Сачин ОЗА (GB)
Мриналини Сачин ОЗА
Лена ШУКЛА (GB)
Лена ШУКЛА
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Новартис Аг
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Abstract

Изобретение относится к соединению формулы I или его фармацевтически приемлемой соли, где R1 представляет собой C1-C8-алкиламинокарбонил, который необязательно замещен 5- или 6-членным гетероциклическим кольцом, содержащим 3-4 кольцевых гетероатома, выбранных из группы, состоящей из кислорода, азота и серы, где кольцо необязательно может быть замещено C1-C8-алкилом или C1-C8-алкоксигруппой; R2 представляет собой C1-С3-алкил или галоген; один из R3 и R4 представляет собой R6, а другой представляет собой R7; R5 представляет собой водород или галоген; R6 представляет собой водород, гидроксигруппу, аминогруппу, -SO2R8, -SO2NH2, -SO2NR9R10, -COR8, -CONHR8, -NHSO2R8, нитрил, карбокси, -OR8 или C1-C8-галогеналкил; R7 представляет собой водород, -OR11, галоген, карбокси, -SO2R8, цианогруппу или С1-С8-галогеналкил, или когда R4 представляет собой R7, то R7 также может представлять собой -NR12R13; R8 и R11 независимо представляют собой C1-C8-алкил или С3-С8-циклоалкил, которые необязательно могут быть замещены гидроксигруппой, С1-С8-алкоксигруппой, нитрилом, аминогруппой, C1-C8-алкиламиногруппой или ди(С1-С8-алкил)аминогруппой; любой R9 представляет собой C1-C8-алкил или С3-С8-циклоалкил, которые необязательно могут быть замещены гидроксигруппой, C1-C8-алкоксигруппой, нитрилом, аминогруппой, C1-C8-алкиламиногруппой, ди(С1-С8-алкил)аминогруппой или 5- или 6-членным гетероциклическим кольцом, содержащим один или два кольцевых гетероатома, выбранных из группы, состоящей из кислорода и азота, где кольцо необязательно может быть замещено C1-C8-алкилом, и R10 представляет собой водород или C1-C8-алкил; или R9 и R10 вместе с атомом азота, к которому они присоединены, образуют 5- или 6-членное гетероциклическое кольцо, которо�

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Claims (6)

1. Соединение формулы (I) или его фармацевтически приемлемая соль
Figure 00000098

где R1 представляет собой С1-С8-алкиламинокарбонил, который необязательно замещен 5- или 6-членным гетероциклическим кольцом, содержащим 3-4 кольцевых гетероатома, выбранных из группы, состоящей из кислорода, азота и серы, где кольцо необязательно может быть замещено C1-C8-алкилом или С1-С8-алкоксигруппой;
R2 представляет собой C1-С3-алкил или галоген;
один из R3 и R4 представляет собой R6, а другой представляет собой R7;
R5 представляет собой водород или галоген;
R6 представляет собой водород, гидроксигруппу, аминогруппу, -SO2R8, -SO2NH2, -SO2NR9R10, -COR8, -CONHR8, -NHSO2R8, нитрил, карбокси, -OR8 или C1-C8-галогеналкил;
R7 представляет собой водород, -OR11, галоген, карбокси, -SO2R8, цианогруппу или C1-C8-галогеналкил, или когда R4 представляет собой R7, то R7 также может представлять собой -NR12R13;
R8 и R11 независимо представляют собой C1-C8-алкил или С3-С8-циклоалкил, которые необязательно могут быть замещены гидроксигруппой, C1-C8-алкоксигруппой, нитрилом, аминогруппой, C1-C8-алкиламиногруппой или ди(С1-С8-алкил)аминогруппой;
любой R9 представляет собой C1-C8-алкил или С3-С8-циклоалкил, которые необязательно могут быть замещены гидроксигруппой, C1-C8-алкоксигруппой, нитрилом, аминогруппой, С1-С8-алкиламиногруппой, ди(С1-С8-алкил)аминогруппой или 5- или 6-членным гетероциклическим кольцом, содержащим один или два кольцевых гетероатома, выбранных из группы, состоящей из кислорода и азота, где кольцо необязательно может быть замещено C1-C8-алкилом, и R10 представляет собой водород или C1-C8-алкил; или R9 и R10 вместе с атомом азота, к которому они присоединены, образуют 5- или 6-членное гетероциклическое кольцо, которое содержит один или два дополнительных гетероатома азота, где кольцо необязательно может быть замещено C1-C8-алкилом;
любой R12 представляет собой C1-C8-алкил или С3-С8-циклоалкил, которые могут быть необязательно замещены ди(С1-С8-алкил)аминогруппой, и R13 представляет собой водород или С1-С8-алкил; или R12 и R13 вместе с атомом азота, к которому они присоединены, образуют 5- или 6- членное гетероциклическое кольцо, которое содержит один или два дополнительных гетероатома азота, где кольцо необязательно может быть замещено С1-С8-алкилом.
2. Соединение формулы (I) по п.1, где
R1 представляет собой C1-C8-алкиламинокарбонил, который необязательно может быть замещен 5- или 6-членным гетероциклическим кольцом, содержащим 3-4 кольцевых гетероатома, выбранных из группы, состоящей из кислорода, азота и серы, где кольцо необязательно может быть замещено C1-C8-алкилом или C1-C8-алкоксигруппой;
R2 представляет собой C1-С3-алкил;
один из R3 и R4 представляет собой R6, а другой представляет собой R7;
R5 представляет собой водород или галоген;
R6 представляет собой водород, гидроксигруппу, аминогруппу, -SO2R8, -SO2NH2, -SO2NR9R10, -COR8, -CONHR8, -NHSO2R8, нитрил, карбокси, -OR8 или C1-C8-галогеналкил;
и все остальные заместители имеют значения, определенные в п.1.
3. Соединение формулы (I) по п.1, где
R1 представляет собой С1-С8-алкиламинокарбонил, который необязательно может быть замещен 5- или 6-членным гетероциклическим кольцом, содержащим 3-4 кольцевых гетероатома, выбранных из группы, состоящей из кислорода, азота и серы, где кольцо необязательно может быть замещено C1-C8-алкилом или C1-C8-алкоксигруппой;
R2 представляет собой С1-С3-алкил;
один из R3 и R4 представляет собой R6, а другой представляет собой R7;
R5 представляет собой водород или галоген;
R6 представляет собой водород, гидроксигруппу, аминогруппу, -SO2R8, -SO2NH2, -SO2NR9R10, -COR8, -CONHR8, -NHSO2R8, нитрил, карбокси, -OR8 или C1-C8-галогеналкил;
R7 представляет собой водород, -OR11, фтор, хлор, бром, цианогруппу или С1-С4-галогеналкил;
и все остальные заместители имеют значения, определенные в п.1.
4. Соединение по п.1, выбранное из
1-[2-(2-этил-2Н-тетразол-5-ил)этил]-3-[5-(3-фтор-4-метансульфонилфенил)-4-метилтиазол-2-ил]мочевины;
1-[2-(1-этил-1Н-тетразол-5-ил)этил]-3-[5-(3-фтор-4-метансульфонилфенил)-4-метилтиазол-2-ил]мочевины; и
1-[5-(3-фтор-4-метансульфонилфенил)-4-метилтиазол-2-ил]-3-[2-(1Н-тетразол-5-ил)этил]мочевины.
5. Применение соединения по любому из пп.1-4 для получения фармацевтического средства, предназначенного для лечения заболеваний, опосредуемых фосфатидилинозитол 3-киназой.
6. Способ лечения заболевания, опосредуемого фосфатидилинозитол 3-киназой, включающий введение пациенту, нуждающемуся в таком лечении, соединения по п.1 в эффективном количестве.
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