EA022420B1 - Гетероциклические ингибиторы глутаминилциклазы (qc, ec 2.3.2.5) - Google Patents
Гетероциклические ингибиторы глутаминилциклазы (qc, ec 2.3.2.5) Download PDFInfo
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Abstract
Изобретение относится к новым гетероциклическим производным формулы (I)в качестве ингибиторов глутаминилциклазы (QC, ЕС 2.3.2.5). QC катализирует внутримолекулярную циклизацию N-концевых глутаминовых остатков с образованием пироглутаминовой кислоты (5-оксопролил, pGlu*) с выделением в свободном состоянии аммиака, и внутримолекулярную циклизацию N-концевых глутаматных остатков с образованием пироглутаминовой кислоты с выделением в свободном состоянии воды.
Description
(57) Изобретение относится к новым гетероциклическим производным формулы (I)
(I), в качестве ингибиторов глутаминилциклазы (ОС. ЕС 2.3.2.5). ОС катализирует внутримолекулярную циклизацию Ν-концевых глутаминовых остатков с образованием пироглутаминовой кислоты (5-оксопролил, рС1и*) с выделением в свободном состоянии аммиака, и внутримолекулярную циклизацию Ν-концевых глутаматных остатков с образованием пироглутаминовой кислоты с выделением в свободном состоянии воды.
Область техники, к которой относится изобретение
Claims (20)
1. Соединение формулы (I) или его фармацевтически приемлемая соль или полиморф, включая все его стереоизомеры, в которой
К1 обозначает -СгС6алкил, -С6-С8арил, -Сэ-С6циклоалкил, -хинолин, -Сэ-С6гетероциклил, -Сэ-С6 циклоалкил, замещенный фенилом, -Сэ-С6циклоалкил, замещенный феноксигруппой, -фенил, замещенный Сэ-С6циклоалкилом, -фенил, замещенный фенилом, Сэ-С6гетероциклил, замещенный фенилом, фенил, замещенный Сэ-С6гетероциклилом, фенил, замещенный -О-Сэ-С6циклоалкилом, или фенил, замещенный -Сэ-С6циклоалкил-С3-С6гетероциклилом, где любой из вышеуказанных Сэ-С6гетероциклилов содержит один или два гетероатома, выбранных из N и О и где любая из вышеуказанных С6-С8арильных, Сэ-С6циклоалкильных, Сэ-С6гетероциклильных, фенильных или феноксигрупп необязательно может быть замещена 1,2 или 3 группами, выбранными из СгС6алкила и галогена;
К2 обозначает -СгС6алкил, СгС6галогеналкил, -С6-С8арил;
где вышеуказанная арильная группа необязательно может быть замещена 1, 2 или 3 группами галогена; и
К3 обозначает СгС6алкил или СгС6галогеналкил.
2. Соединение по п.1, в котором К1 обозначает -СгС6алкил, -С6-С8арил, -Сэ-С6циклоалкил, -Сэ-С6 циклоалкил, замещенный фенилом, -Сэ-С6циклоалкил, замещенный феноксигруппой, -фенил, замещенный Сэ-С6циклоалкилом, -фенил, замещенный фенилом, Сэ-С6гетероциклил, замещенный фенилом, фенил, замещенный Сэ-С6гетероциклилом, фенил, замещенный -О-Сэ-С6циклоалкилом, или фенил, замещенный -Сэ-С6циклоалкил-С3-С6гетероциклилом.
3. Соединение по п.2, в котором К1 обозначает -СгС6алкил, -С6-С8арил, -Сэ-С6циклоалкил, -Сэ-С6 гетероарил, -фенил, замещенный фенилом, фенил, замещенный Сэ-С6гетероциклилом, или фенил, замещенный -О-Сэ-С6циклоалкилом, где указанная фенильная группа необязательно замещена 1, 2 или 3 группами галогена, где указанная гетероциклильная группа необязательно замещена 1, 2 или 3 СгС6алкильными группами и где указанная циклоалкильная группа необязательно замещена 1, 2 или 3 группами галогена.
4. Соединение по п.3, в котором К1 обозначает фенил, необязательно замещенный 1, 2 или 3 группами галогена, такой как 2,3-дифторфенил.
5. Соединение по одному из пп.1-4, в котором К2 обозначает метил, этил, пропил, изопропил, трифторметил или фенил, необязательно замещенный 1, 2 или 3 группами галогена.
6. Соединение по п.5, в котором К2 обозначает метил или незамещенный фенил.
7. Соединение по одному из пп.1-6, в котором К3 обозначает метил.
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8. Соединение по одному из пп.1-7, в котором К3 обозначает 2,2,2-трифторэтил или 2,2,3,3тетрафторпропил.
9. Соединение по одному из примеров 1-35 или его фармацевтически приемлемая соль или стереоизомер.
10. Соединение по п.1, которое представляет собой 1-(1Н-бензо[й]имидазол-6-ил)-5-(2,3дифторфенил)-3-метокси-4-метил-1Н-пиррол-2(5Н)-он или его фармацевтически приемлемую соль или полиморф.
11. Применение соединения по пп.1-10 в качестве лекарственного средства, обладающего ингибирующей активностью в отношении глутаминилциклазы.
12. Фармацевтическая композиция, содержащая соединение по одному из пп.1-10 в комбинации с одним или несколькими терапевтически приемлемыми разбавителями или носителями.
13. Фармацевтическая композиция по п.12, которая дополнительно содержит по меньшей мере одно соединение, выбранное из группы, включающей нейрозащитные средства, ингибиторы отложения амилоидного белка и ингибиторы синтеза бета-амилоида.
14. Фармацевтическая композиция по п.12 или 13, которая дополнительно содержит по меньшей мере одно соединение, выбранное из группы, включающей антитела к бета-амилоиду; ингибиторы ацетилхолинэстеразы (АСЕ), ингибиторы бета-секретаз, ингибиторы гамма-секретаз и антагонисты рецептора ММОА.
15. Применение соединения по одному из пп.1-10 или фармацевтической композиции по одному из пп.12-14 для лечения заболевания, выбранного из группы, включающей болезнь Кеннеди, рак двенадцатиперстной кишки, сопровождающийся или не сопровождающийся инфекциями НеНсоЬас1ег ру1оп, колоректальный рак, синдром Золлигера-Эллисона, рак желудка, сопровождающийся или не сопровождающийся инфекциями НеНсоЬас1ег ру1оп, патогенные психотические состояния, шизофрению, бесплодие, неоплазию, воспалительные ответы организма, рак, злокачественные метастазы, меланому, псориаз, нарушенные гуморальные и клеточно-опосредуемые иммунные ответы, процессы адгезии и миграции лейкоцитов в эндотелии, нарушенное всасывание пищи, нарушения сна-бодрствования, нарушенную гомеостатическую регуляцию энергетического метаболизма, нарушенную функцию вегетативной нервной системы, нарушенный гормональный баланс или нарушенную регуляцию жидкостей организма, рассеянный склероз, синдром Гийена-Барре и хроническую воспалительную демиелинизирующую полирадикулоневропатию.
16. Применение соединения по одному из пп.1-10 или фармацевтической композиции по одному из пп.12-14 для лечения заболевания, выбранного из группы, включающей умеренное когнитивное нарушение, болезнь Альцгеймера, семейную британскую деменцию, семейную датскую деменцию, нейродегенерацию при синдроме Дауна и болезнь Гентингтона.
17. Применение соединения по одному из пп.1-10 или фармацевтической композиции по одному из пп.12-14 для лечения заболевания, выбранного из группы, включающей ревматоидный артрит, атеросклероз, панкреатит и рестеноз.
18. Способ лечения или предупреждения заболевания, выбранного из группы, включающей болезнь Кеннеди, язвенное заболевание, рак двенадцатиперстной кишки, сопровождающийся или не сопровождающийся инфекциями НеПсоЬасЮг ру1оп, колоректальный рак, синдром Золлигера-Эллисона, рак желудка, сопровождающийся или не сопровождающийся инфекциями НеПсоЬасЮг ру1оп, патогенные психотические состояния, шизофрению, бесплодие, неоплазию, воспалительные ответы организма, рак, злокачественные метастазы, меланому, псориаз, нарушенные гуморальные и клеточно-опосредуемые иммунные ответы, процессы адгезии и миграции лейкоцитов в эндотелии, нарушенное всасывание пищи, нарушения сна-бодрствования, нарушенную гомеостатическую регуляцию энергетического метаболизма, нарушенную функцию вегетативной нервной системы, нарушенный гормональный баланс или нарушенную регуляцию жидкостей организма, рассеянный склероз, синдром Гийена-Барре и хроническую воспалительную демиелинизирующую полирадикулоневропатию, включающий введение субъекту соединения по одному из пп.1-10 или фармацевтической композицию по одному из пп.12-14 в эффективном количестве.
19. Способ лечения или предупреждения заболевания, выбранного из группы, включающей умеренное когнитивное нарушение, болезнь Альцгеймера, семейную британскую деменцию, семейную датскую деменцию, нейродегенерацию при синдроме Дауна и болезнь Гентингтона, включающий введение субъекту соединения по одному из пп.1-10 или фармацевтической композиции по одному из пп.12-14 в эффективном количестве.
20. Способ лечения или предупреждения заболевания, выбранного из группы, включающей ревматоидный артрит, атеросклероз, панкреатит и рестеноз, включающий введение субъекту соединения по одному из пп.1-10 или фармацевтической композиции по одному из пп.12-14 в эффективном количестве.
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US31233910P | 2010-03-10 | 2010-03-10 | |
PCT/EP2011/053576 WO2011110613A1 (en) | 2010-03-10 | 2011-03-10 | Heterocyclic inhibitors of glutaminyl cyclase (qc, ec 2.3.2.5) |
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EA201201275A1 (ru) | 2013-04-30 |
HK1178528A1 (zh) | 2013-09-13 |
AU2011226074B2 (en) | 2015-01-22 |
US20110224254A1 (en) | 2011-09-15 |
BR112012022478A2 (pt) | 2017-02-14 |
EP2545047A1 (en) | 2013-01-16 |
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JP2013521325A (ja) | 2013-06-10 |
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AU2011226074A1 (en) | 2012-10-04 |
WO2011110613A1 (en) | 2011-09-15 |
DK2545047T3 (da) | 2014-07-28 |
BR112012022478B1 (pt) | 2021-09-21 |
CN102791704A (zh) | 2012-11-21 |
SG183229A1 (en) | 2012-09-27 |
EP2545047B9 (en) | 2015-06-10 |
NZ602312A (en) | 2014-02-28 |
EP2545047B1 (en) | 2014-04-23 |
CA2789440C (en) | 2020-03-24 |
US8269019B2 (en) | 2012-09-18 |
JP5688745B2 (ja) | 2015-03-25 |
MX2012010470A (es) | 2012-10-09 |
CN102791704B (zh) | 2015-11-25 |
KR20130016208A (ko) | 2013-02-14 |
CA2789440A1 (en) | 2011-09-15 |
US20120283259A1 (en) | 2012-11-08 |
IL221243A (en) | 2016-06-30 |
IL221243A0 (en) | 2012-10-31 |
ES2481823T3 (es) | 2014-07-31 |
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