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RU2012132692A - Новые ингибиторы s-нитрозоглутатионредуктазы - Google Patents

Новые ингибиторы s-нитрозоглутатионредуктазы Download PDF

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RU2012132692A
RU2012132692A RU2012132692/13A RU2012132692A RU2012132692A RU 2012132692 A RU2012132692 A RU 2012132692A RU 2012132692/13 A RU2012132692/13 A RU 2012132692/13A RU 2012132692 A RU2012132692 A RU 2012132692A RU 2012132692 A RU2012132692 A RU 2012132692A
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hydroxy
chromen
oxadiazol
trifluoromethyl
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Сичэн СУНЬ
Цзянь ЦЮ
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Н30 Фармасьютиклз, ИНК.
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Abstract

1. Соединение формулы (I)в которойХ выбран из группы, включающей О и S;Y выбран из группы, включающей О и S;Z выбран из группы, включающей Z, Z, Zи Z, гдеZобозначает,Zобозначает,Zобозначает, иZобозначаетпри условии, что Z обозначает только Z, когда по меньшей мере один из Х или Y обозначает S;Rвыбран из группы, включающей водород, (С-С)алкил, (С-С)циклоалкил, (С-С)галогеналкил, незамещенный арил(С-С)алкил, замещенный арил(С-С)алкил, (С-С)гетероалкил, замещенный или незамещенный арил и замещенный или незамещенный гетероарил;Rвыбран из группы, включающей водород, галоген, цианогруппу и (С-С)алкоксигруппу;Rвыбран из группы, включающей водород, галоген, (С-С)алкил, (С-С)галогеналкил, (С-С)алкоксигруппу, цианогруппу и N,N-диметиламиногруппу;Rвыбран из группы, включающей тетразол, оксадиазолон, тиадиазолон, метилсульфонилкарбамоил и N-гидроксикарбамоил; иRвыбран из группы, включающей карбоксигруппу, тетразол, оксадиазолон, тиадиазолон, метилсульфонилкарбамоил и N-гидроксикарбамоил.2. Соединение по п. 1, в которомRвыбран из группы, включающей тетразол, 1,2,4-оксадиазол-5(4Н)-он-3-ил, 1,2,4-тиадиазол-5(4Н)-он-3-ил, 1,3,4-оксадиазол-2(3Н)-он-5-ил, 1,3,4-тиадиазол-2(3Н)-он-5-ил, 1,2,4-тиадиазол-3(2Н)-он-5-ил, 1,2,4-оксадиазол-3(2Н)-он-5-ил, метилсульфонилкарбамоил и N-гидроксикарбамоил; иRвыбран из группы, включающей карбоксигруппу, тетразол, 1,2,4-оксадиазол-5(4Н)-он-3-ил, 1,2,4-тиадиазол-5(4Н)-он-3-ил, 1,3,4-оксадиазол-2(3Н)-он-5-ил, 1,3,4-тиадиазол-2(3Н)-он-5-ил, 1,2,4-тиадиазол-3(2Н)-он-5-ил, 1,2,4-оксадиазол-3(2Н)-он-5-ил, метилсульфонилкарбамоил и N-гидроксикарбамоил.3. Соединение по п. 1, в которомRвыбран из группы, включающей водород, CF, CFH, CFCH, CFCHCH, метил, изопропил, изобутил, циклопентил, СНОСН, SCH, бензил, 4-карбоксибенз�

Claims (8)

1. Соединение формулы (I)
Figure 00000001
в которой
Х выбран из группы, включающей О и S;
Y выбран из группы, включающей О и S;
Z выбран из группы, включающей Z1, Z2, Z3 и Z4, где
Z1 обозначает
Figure 00000002
,
Z2 обозначает
Figure 00000003
,
Z3 обозначает
Figure 00000004
, и
Z4 обозначает
Figure 00000005
при условии, что Z обозначает только Z4, когда по меньшей мере один из Х или Y обозначает S;
R1 выбран из группы, включающей водород, (С1-С6)алкил, (С3-С7)циклоалкил, (С1-С6)галогеналкил, незамещенный арил(С1-С4)алкил, замещенный арил(С1-С6)алкил, (С1-С6)гетероалкил, замещенный или незамещенный арил и замещенный или незамещенный гетероарил;
R2 выбран из группы, включающей водород, галоген, цианогруппу и (С1-С6)алкоксигруппу;
R3 выбран из группы, включающей водород, галоген, (С1-С6)алкил, (С1-С6)галогеналкил, (С1-С6)алкоксигруппу, цианогруппу и N,N-диметиламиногруппу;
R4 выбран из группы, включающей тетразол, оксадиазолон, тиадиазолон, метилсульфонилкарбамоил и N-гидроксикарбамоил; и
R5 выбран из группы, включающей карбоксигруппу, тетразол, оксадиазолон, тиадиазолон, метилсульфонилкарбамоил и N-гидроксикарбамоил.
2. Соединение по п. 1, в котором
R4 выбран из группы, включающей тетразол, 1,2,4-оксадиазол-5(4Н)-он-3-ил, 1,2,4-тиадиазол-5(4Н)-он-3-ил, 1,3,4-оксадиазол-2(3Н)-он-5-ил, 1,3,4-тиадиазол-2(3Н)-он-5-ил, 1,2,4-тиадиазол-3(2Н)-он-5-ил, 1,2,4-оксадиазол-3(2Н)-он-5-ил, метилсульфонилкарбамоил и N-гидроксикарбамоил; и
R5 выбран из группы, включающей карбоксигруппу, тетразол, 1,2,4-оксадиазол-5(4Н)-он-3-ил, 1,2,4-тиадиазол-5(4Н)-он-3-ил, 1,3,4-оксадиазол-2(3Н)-он-5-ил, 1,3,4-тиадиазол-2(3Н)-он-5-ил, 1,2,4-тиадиазол-3(2Н)-он-5-ил, 1,2,4-оксадиазол-3(2Н)-он-5-ил, метилсульфонилкарбамоил и N-гидроксикарбамоил.
3. Соединение по п. 1, в котором
R1 выбран из группы, включающей водород, CF3, CF2H, CF2CH3, CF2CH2CH3, метил, изопропил, изобутил, циклопентил, СН2ОСН3, SCH3, бензил, 4-карбоксибензил, тиофен-2-ил и тиофен-3-ил;
R2 выбран из группы, включающей водород, фтор, хлор, метоксигруппу и цианогруппу; и
R3 выбран из группы, включающей водород, фтор, хлор, метил, CF3, метоксигруппу, цианогруппу и N,N-диметиламиногруппу.
4. Соединение по п. 1, в котором R1 выбран из группы, включающей водород, CF3, CF2H, метил и 4-карбоксибензил;
R2 выбран из группы, включающей водород и фтор;
R3 выбран из группы, включающей водород, фтор, хлор и метил;
R4 выбран из группы, включающей тетразол, 1,2,4-оксадиазол-5(4Н)-он-3-ил, 1,2,4-тиадиазол-5(4Н)-он-3-ил, 1,3,4-оксадиазол-2(3Н)-он-5-ил, метилсульфонилкарбамоил и N-гидроксикарбамоил; и
R5 выбран из группы, включающей карбоксигруппу, тетразол, 1,2,4-оксадиазол-5(4Н)-он-3-ил, 1,2,4-тиадиазол-5(4Н)-он-3-ил, 1,3,4-оксадиазол-2(3Н)-он-5-ил, метилсульфонилкарбамоил и N-гидроксикарбамоил.
5. Соединение по п. 1, выбранное из группы, включающей 3-(4-(1Н-тетразол-5-ил)фенил)-7-гидрокси-2-(трифторметил)-4Н-хромен-4-он;
5-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)тиофен-2-карбоновую кислоту;
(транс)-4-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)циклогексанкарбоновую кислоту;
(цис)-4-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)циклогексанкарбоновую кислоту;
3-(4-(1Н-тетразол-5-ил)фенил)-2-(дифторметил)-7-гидрокси-4Н-хромен-4-он;
3-(4-(1Н-тетразол-5-ил)фенил)-7-гидрокси-2-метил-4Н-хромен-4-он;
4-(2-(4-карбоксибензил)-7-гидрокси-4-оксо-4Н-тиохромен-3-ил)бензойную кислоту;
4-(7-гидрокси-2-метил-4-оксо-4Н-тиохромен-3-ил)бензойную кислоту;
3-(4-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)фенил)-1,2,4-оксадиазол-5(4Н)-он;
4-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)-N-(метилсульфонил)бензамид;
3-(4-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)фенил)-1,2,4-тиадиазол-5(4Н)-он;
3-(4-(1Н-тетразол-5-ил)фенил)-7-гидрокси-2-метил-4Н-тиохромен-4-он;
5-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)тиофен-3-карбоновую кислоту;
3-((транс)-4-(1Н-тетразол-5-ил)циклогексил)-7-гидрокси-2-(трифторметил)-4Н-хромен-4-он;
N-гидрокси-4-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)бензамид;
3-(2-хлор-4-(1Н-тетразол-5-ил)фенил)-7-гидрокси-2-(трифторметил)-4Н-хромен-4-он;
3-(3-хлор-4-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)фенил)-1,2,4-оксадиазол-5(4Н)-он;
3-(3-фтор-4-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)фенил)-1,2,4-оксадиазол-5(4Н)-он;
3-(3-хлор-4-(1Н-тетразол-5-ил)фенил)-7-гидрокси-2-(трифторметил)-4Н-хромен-4-он; и
3-(4-(1Н-тетразол-5-ил)фенил)-7-гидрокси-4Н-хромен-4-он; и
5-(4-(7-гидрокси-4-оксо-2-(трифторметил)-4Н-хромен-3-ил)фенил)-1,3,4-оксадиазол-2(3Н)-он.
6. Фармацевтическая композиция, содержащая терапевтически эффективное количество соединения по любому из предыдущих пунктов вместе с фармацевтически приемлемым носителем или инертным наполнителем.
7. Способ лечения заболевания или патологического состояния, который включает введение нуждающемуся в нем пациенту терапевтически эффективного количества соединения формулы I по любому из предыдущих пунктов.
8. Способ получения соединения формулы I по любому из предыдущих пунктов.
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