RU2007141566A - 1н-хиназолин-2,4-дионы - Google Patents

1н-хиназолин-2,4-дионы Download PDF

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RU2007141566A
RU2007141566A RU2007141566/04A RU2007141566A RU2007141566A RU 2007141566 A RU2007141566 A RU 2007141566A RU 2007141566/04 A RU2007141566/04 A RU 2007141566/04A RU 2007141566 A RU2007141566 A RU 2007141566A RU 2007141566 A RU2007141566 A RU 2007141566A
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Russia
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formula
compound
alkyl
alkylamino
amino
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RU2007141566/04A
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RU2435760C2 (ru
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Ханс АЛЛЬГАЙЕР (DE)
Ханс Алльгайер
Ив ОБЕРСОН (CH)
Ив Оберсон
Давид КАРКАШ (CH)
Давид КАРКАШ
Филипп ФЛЕРШАЙМ (CH)
Филипп ФЛЕРШАЙМ
Кристель ГИБУРДЕНШ (CH)
Кристель ГИБУРДЕНШ
Вольфганг ФРЕШТЛЬ (CH)
Вольфганг ФРЕШТЛЬ
Йерг КАЛЛЕН (CH)
Йерг КАЛЛЕН
Мануэль КОЛЛЕР (CH)
Мануэль КОЛЛЕР
Анри МАТТЕ (FR)
Анри Матте
Йоахим НОЦУЛАК (DE)
Йоахим Ноцулак
Давид ОРЕН (FR)
Давид Орен
Жоанне РЕНО (CH)
Жоанне РЕНО
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Новартис АГ (CH)
Новартис Аг
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Application filed by Новартис АГ (CH), Новартис Аг filed Critical Новартис АГ (CH)
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    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C07D239/96—Two oxygen atoms
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

1. Соединения формулы (I) ! ! где R1 означает CF3, CHF2, CH2F, СН3CHF-, СН3CF3-, этил или изопропил, а ! R2 означает алкил, замещенный одним или более заместителями, выбранными из группы, включающей галоген, нитро, циано, ацил, гидрокси, оксо (=O), алкокси, циклоалкокси, ацилокси, алкоксикарбонилокси, амино, алкиламино, диалкиламино, формил, ациламино, алкоксикарбониламино, или ! R2 означает гетероциклилалкил, замещенный одним или более заместителями, выбранными из группы, включающей галоген, нитро, циано, гидрокси, алкокси, алкилкарбонилокси, алкоксикарбонилокси, амино, алкиламино, диалкиламино, алкоксикарбониламино, или ! R2 означает фенил, замещенный одним или более заместителями, выбранными из группы, включающей циано, гидрокси, алкандиил, алкендиил, алкокси, гидроксиалкил, формил, алкилкарбонил, алкоксикарбонил, алкилкарбонилокси, алкоксикарбонилокси, амино, алкиламино, диалкиламино, аминоалкил, алкиламиноалкил, диалкиламиноалкил, алкоксикарбониламино, или ! R2 означает гетероциклил, необязательно замещенный одним или более заместителями, выбранными из группы, включающей галоген, гидрокси, амино, нитро, циано, алкил, гидроксиалкил, алкоксиалкил, аминоалкил, алкиламиноалкил, диалкиламиноалкил, ацил, алкокси, ацилокси, алкоксикарбонилокси, амино, алкиламино, диалкиламино, ациламино, алкоксикарбониламино, причем гетероцикл присоединен к фенильному циклу через атом углерода, и их соли. ! 2. Соединения по п.1, где ! R1 означает CF3 или изопропил, а ! R2 означает С1-С4алкил, замещенный одним-тремя заместителями, выбранными из группы, включающей галоген, нитро, циано, НСО, С1-С4алкилкарбонил, гидрокси, С1-С4алкокси, С1-С4алкилкарбонилокси, С1-С4алкокси�

Claims (18)

1. Соединения формулы (I)
где R1 означает CF3, CHF2, CH2F, СН3CHF-, СН3CF3-, этил или изопропил, а
R2 означает алкил, замещенный одним или более заместителями, выбранными из группы, включающей галоген, нитро, циано, ацил, гидрокси, оксо (=O), алкокси, циклоалкокси, ацилокси, алкоксикарбонилокси, амино, алкиламино, диалкиламино, формил, ациламино, алкоксикарбониламино, или
R2 означает гетероциклилалкил, замещенный одним или более заместителями, выбранными из группы, включающей галоген, нитро, циано, гидрокси, алкокси, алкилкарбонилокси, алкоксикарбонилокси, амино, алкиламино, диалкиламино, алкоксикарбониламино, или
R2 означает фенил, замещенный одним или более заместителями, выбранными из группы, включающей циано, гидрокси, алкандиил, алкендиил, алкокси, гидроксиалкил, формил, алкилкарбонил, алкоксикарбонил, алкилкарбонилокси, алкоксикарбонилокси, амино, алкиламино, диалкиламино, аминоалкил, алкиламиноалкил, диалкиламиноалкил, алкоксикарбониламино, или
R2 означает гетероциклил, необязательно замещенный одним или более заместителями, выбранными из группы, включающей галоген, гидрокси, амино, нитро, циано, алкил, гидроксиалкил, алкоксиалкил, аминоалкил, алкиламиноалкил, диалкиламиноалкил, ацил, алкокси, ацилокси, алкоксикарбонилокси, амино, алкиламино, диалкиламино, ациламино, алкоксикарбониламино, причем гетероцикл присоединен к фенильному циклу через атом углерода, и их соли.
2. Соединения по п.1, где
R1 означает CF3 или изопропил, а
R2 означает С1-С4алкил, замещенный одним-тремя заместителями, выбранными из группы, включающей галоген, нитро, циано, НСО, С1-С4алкилкарбонил, гидрокси, С1-С4алкокси, С1-С4алкилкарбонилокси, С1-С4алкоксикарбонилокси, амино, С1-С4алкиламино, ди(С1-С4)алкиламино, ациламино, С1-С4алкоксикарбониламино, за исключением группы трифторметил, или
R2 означает гетероциклил(С1-С4)алкил, замещенный одним-тремя заместителями, выбранными из группы, включающей галоген, нитро, циано, гидрокси, С1-С4алкокси, С1-С4алкилкарбонилокси, C1-С4алкоксикарбонилокси, амино, С1-С4алкиламино, ди(С1-С4)алкиламино, С1-С4алкоксикарбониламино, причем гетероциклил содержит 3-11 атомов в цикле, из которых 1-3 атома являются гетероатомами, или
R2 означает фенил, замещенный одним-тремя заместителями, выбранными из группы, включающей циано, гидрокси, алкандиил, алкендиил, С1-С4алкокси, С1-С4алкилкарбонилокси, C1-С-алкоксикарбонилокси, амино, С1-С4алкиламино, ди(С1-С4)алкиламино, С1-С4алкоксикарбониламино, или
R2 означает гетероциклил, необязательно замещенный одним-тремя заместителями, выбранными из группы, включающей галоген, гидрокси, амино, нитро, циано, С1-С4алкил, гидрокси(С1-С4)алкил, С1-С4алкоксиалкил, амино(С1-С4)алкил, С1-С4алкиламино(С1-С4)алкил, ди(С1-С4)алкиламино(С1-С4)алкил, НСО, С1-С4алкилкарбонил, С1-С4алкокси, ацилокси, C1-С4алкоксикарбонилокси, амино, С1-С4алкиламино, ди(С1-С4)алкиламино, ациламино, С1-С4алкоксикарбониламино, причем гетероциклил содержит 3-11 атомов в цикле, из которых 1-3 атома являются гетероатомами, и гетероциклил присоединен к фенильному циклу через атом углерода.
3. Соединения по п.1 или 2, где R1 означает CF3.
4. Способ получения соединений формулы (I) по п.1, заключающийся в том, что
из соединения формулы (II)
Figure 00000002
где R1 и R2 имеют значения, указанные в п.1, а R3 означает С1-С4алкил, по реакции с 4-хлорфенилхлорформиатом, необязательно в присутствии разбавителя, и необязательно в присутствии вспомогательных реагентов, получают соединение формулы (IV)
Figure 00000003
а из соединения формулы (IV) по реакции циклоконденсации с сульфонилгидразином, H2N-NH-SO2-CH3, в инертном растворителе в присутствии или при последующем добавлении основания получают соединение формулы (I),
или
из соединения формулы (II)
Figure 00000004
где R1 и R2 имеют значения, указанные в п.1, а R3 означает С1-С4алкил, по реакции с фосгеном или трифосгеном необязательно в присутствии разбавителя и необязательно в присутствии вспомогательных реагентов получают соединение формулы (III)
Figure 00000005
а из соединения формулы (III) по реакции циклоконденсации с сульфонилгидразином, H2N-NH-SO2-CH3, необязательно в инертном растворителе в присутствии или при последующем добавлении основания получают соединение формулы (I),
или
из соединения формулы (XI)
Figure 00000006
где R1 имеет значения, указанные в п.1, при востановлении, например, водородом, необязательно в присутствии катализатора и в присутствии уксусного ангидрида, необязательно в присутствии разбавителя получают соединение формулы (I')
Figure 00000007
где R1 имеет значения, указанные в п.1, а из соединения формулы (I') по реакциям циклизации, замещения, окисления и/или восстановления получают другое соединение формулы (I).
5. Соединения по пп.1-3 для применения в качестве лекарственного средства.
6. Фармацевтическая композиция, включающая соединение по любому из пп.1-3.
7. Применение соединения по пп.1-3 для получения лекарственного средства, предназначенного для лечения состояния, опосредованного рецептором АМРА.
8. Применение соединения по пп.1-3 для получения лекарственного средства, предназначенного для лечения эпилепсии или шизофрении.
9. Способ лечения состояния, опосредованного рецептором АМРА, у субъекта, который нуждается в таком лечении, включающий введение такому субъекту терапевтически эффективного количества соединения по пп.1-3.
10. Соединение формулы (II')
Figure 00000008
где R2 имеет значение, указанное выше для соединений формулы (I), a
R3 означает водород или С1-С4алкил.
11. Соединение формулы (III')
Figure 00000009
где R2 имеет значение, указанное выше для соединений формулы (I), a
R3 означает водород или С1-С4алкил.
12. Соединение формулы (IV')
Figure 00000010
где R2 имеет значение, указанное выше для соединений формулы (I), a
R3 означает водород или С1-С4алкил.
13. Соединение формулы (VII)
Figure 00000011
где R1 имеет значение, указанное выше для соединений формулы (I), a
R3 означает водород или С1-С4алкил.
14. Соединение формулы (IIX)
Figure 00000012
где R1 имеет значение, указанное выше для соединений формулы (I), a
R3 означает водород или С1-С4алкил.
15. Соединение формулы (IX)
Figure 00000013
где R1 имеет значение, указанное выше для соединений формулы (I).
16. Соединение формулы (X)
Figure 00000014
где R1 имеет значение, указанное выше для соединений формулы (I).
17. Соединение формулы (XI)
Figure 00000006
где R1 имеет значение, указанное выше для соединений формулы (I).
18. Соединение по п.1 или 2, где R1 означает изопропил.
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