RU2494095C2 - Модифицированные миметики лизина - Google Patents

Модифицированные миметики лизина Download PDF

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RU2494095C2
RU2494095C2 RU2008126246/04A RU2008126246A RU2494095C2 RU 2494095 C2 RU2494095 C2 RU 2494095C2 RU 2008126246/04 A RU2008126246/04 A RU 2008126246/04A RU 2008126246 A RU2008126246 A RU 2008126246A RU 2494095 C2 RU2494095 C2 RU 2494095C2
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benzamido
carboxamide
pyrrolidine
carboxylic acid
aminoacetyl
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Бьярн Дью ЛАРСЕН
Йорген Соберг Петерсен
Кетил Йорген ХАУГАН
Джон А. БУТЕРА
Джеймс К. ХЕНАН
Эдвард Х. КЕРНС
Евгений Львович ПЯТНИЦКИЙ
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Вайет
Зиланд Фарма А/С
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Abstract

Изобретение относится к модифицированным миметикам лизина формулы III:
Figure 00000112
или его фармацевтически приемлемой соли, где R1 означает Н; Y' означает NR2R3; R2 означает Н; R3 означает Н, С1-10алкил, C(O)R6, C(O)OR6; R4 означает ОН или NH2; R5 независимо означает Н, С1-10алкил, возможно замещенный галогеном, циклопропил, циклобутил, циклопентил; R6 независимо означает Н, С1-10алкил, возможно замещенный галогеном; Z' означает бензоил, который возможно содержит в качестве заместителей 1-5 групп Q, при этом Q независимо означает F, Cl, Br, I, C1-10алкил, CF3, OCF3, NO2, O-C1-10алкил, ОН, NH2, NH(C1-10алкил), N(C1-10алкил)2 и NHC(O)C1-10алкил. Соединения проявляют антиаритмическую активность, что позволяет использовать их для лечения сердечно-сосудистого заболевания. 4 н. и 16 з.п. ф-лы, 3 табл., 17 схем, 1 ил.

Description

Текст описания приведен в факсимильном виде.
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Claims (20)

1. Соединение, представленное Формулой III:
Figure 00000112

или его фармацевтически приемлемая соль, где
R1 представляет собой Н;
Y' представляет собой NR2R3;
R2 представляет собой Н;
R3 выбран из Н, C1-10алкила, C(O)R6 и C(O)OR6;
R4 представляет собой ОН или NH2;
R5 независимо выбран из Н и C1-10алкила, возможно замещенного галогеном, циклопропила, циклобутила, циклопентила, и R6 независимо выбран из Н и C1-10алкила, возможно замещенного галогеном; и
Z' представляет собой бензоил, который возможно содержит в качестве заместителей 1-5 групп Q, при этом каждая группа Q независимо выбрана из F, Cl, Br, I, C1-10алкила, CF3, OCF3, NO2, O-C1-10алкила, ОН, NH2, NH(C1-10алкил), N(C1-10алкил)2 и NHC(O)C1-10алкила.
2. Соединение по п.1, отличающееся тем, что R3 представляет собой Н.
3. Соединение по п.1, отличающееся тем, что R3 представляет собой C(O)R6, и R6 представляет собой Н или C1-10алкил, возможно замещенный галогеном.
4. Соединение по любому из пп.1-3 следующей структуры:
Figure 00000113

или его фармацевтически приемлемая соль.
5. Соединение по любому из пп.1-3 следующей структуры:
Figure 00000114

или его фармацевтически приемлемая соль.
6. Соединение по любому из пп.1-3 следующей структуры:
Figure 00000115

или его фармацевтически приемлемая соль.
7. Соединение по любому из пп.1-3 следующей структуры:
Figure 00000116

или его фармацевтически приемлемая соль.
8. Соединение по п.1, представляющее собой:
1-(2-Амино-ацетил)-4-(4-нитро-бензоиламино)-пирролидин-2-карбоновую кислоту;
1-(2-Амино-ацетил)-4-бензоиламино-пирролидин-2-карбоновую кислоту;
1-(2-Амино-ацетил)-4-(4-метил-бензоиламино)-пирролидин-2-карбоновую кислоту;
1-(2-Амино-ацетил)-4-(4-метокси-бензоиламино)-пирролидин-2-карбоновую кислоту;
или 1-(2-Амино-ацетил)-4-(4-гидрокси-бензоиламино)-пирролидин-2-карбоновую кислоту;
или его фармацевтически приемлемая соль.
9. Соединение по п.1 или 8, представляющее собой:
(2S,4R) 1-(2-Амино-ацетил)-4-(4-нитро-бензоиламино)-пирролидин-2-карбоновую кислоту;
(2S,4R) 1-(2-Амино-ацетил)-4-бензоиламино-пирролидин-2-карбоновую кислоту;
(2S,4R) 1-(2-Амино-ацетил)-4-(4-метил-бензоиламино)-пирролидин-2-карбоновую кислоту;
(2S,4R) 1-(2-Амино-ацетил)-4-(4-метокси-бензоиламино)-пирролидин-2-карбоновую кислоту; или
(2S,4R) 1-(2-Амино-ацетил)-4-(4-гидрокси-бензоиламино)-пирролидин-2-карбоновую кислоту;
или его фармацевтически приемлемую соль.
10. Соединение по п.1, выбранное из:
1-(2-аминоацетил)-4-бензамидопирролидин-2-карбоксамида;
1-(2-аминоацетил)-4-бензамидо-N-метилпирролидин-2-карбоксамида;
1-(2-аминоацетил)-4-бензамидо-N-этилпирролидин-2-карбоксамида;
1-(2-аминоацетил)-4-бензамидо-N-изопропилпирролидин-2-карбоксамида;
1-(2-амипоацстил)-4-бензамидо-N-циклопропилпирролидин-2-карбоксамида;
4-бензамидо-1-(2-(трет-бутоксикарбониламино)-ацетил)пирролидин-2-карбоксамида;
1-(2-аминоацетил)-4-бензамидо-N-(пентан-3-ил)пирролидин-2-карбоксамида;
1-(2-аминоацетил)-4-бензамидо-N-циклопентилпирролидин-2-карбоксамида;
1-(2-аминоацетил)-4-бензамидо-N-изобутилпирролидин-2-карбоксамида:
1-(2-аминоацетил)-4-бензамидо-N-циклобутилпирролидин-2-карбоксамида;
1-(2-аминоацетил)-4-бензамидо-N-трет-бутилпирролидин-2-карбоксамида;
или его фармацевтически приемлемой соли.
11. Соединение по пп.1 или 10, выбранное из:
(2S,4R) 1-(2-аминоацетил)-4-бензамидопирролидин-2-карбоксамида;
(2S,4R) 1-(2-аминоацетил)-4-бензамидо-N-метилпирролидин-2-карбоксамида;
(2S,4R) 1-(2-аминоацетил)-4-бензамидо-N-этилпирролидина-2-карбоксамида;
(2S,4R) 1-(2-аминоацетил)-4-бензамидо-N-изопропилпирролидин-2-карбоксамида;
(2S,4R) 1-(2-аминоацетил)-4-бензамидо-N-циклопропилпилпирролидин-2-карбоксамида;
(2S,4R) 4-бензамидо-1-(2-трет-бутоксикарбониламино)ацетил)пирролидин-2-карбоксамида;
(2S,4R) 1-(2-аминоацетил)-4-бензамидо-N-(пентан-3-ил)пирролидин-2-карбоксамида;
(2S,4R) 1-(2-аминоацетил)-4-бензамидо-N-циклопентипирролидин-2-карбоксамида;
(2S,4R) 1-(2-аминоацетил)-4-бензамидо-N-изобутилпирролидин-2-карбоксамида;
(2S,4R) 1-(2-аминоацетил)-4-бензамидо-N-циклобутилпирролидин-2-карбоксамида;
(2S,4R) 1-(2-аминоацетил)-4-бензамидо-N-трет-бутилпирролидин-2-карбоксамида;
и его фармацевтически приемлемой соли.
12. Соединение по п.1, представляющее собой:
1-(2-ацетамидоацетил)-4-бензамидопирролидин-2-карбоновую кислоту;
4-бензамидо-1-(2-метиламино)ацетил)-пирролидин-2-карбоновую кислоту;
4-бензамидо-1-(2-(2,2,2-трифторацетамидо)ацетил)пирролидин-2-карбоновую кислоту;
4-бензамидо-1-(2-(трет-бутоксикарбониламино)ацетил)-пирролидин-2-карбоновую кислоту; и
4-бензамидо-1-(2-формамидоацетил)пирролидин-2-карбоновую кислоту;
или его фармацевтически приемлемую соль.
13. Соединение по п.1 или 12, представляющее собой:
(2S,4R) 1-(2-ацетамидоацетил)-4-бензамидопирролидин-2-карбоновую кислоту;
(2S,4R) 4-бензамидо-1-(2-метиламино)ацетил)-пирролидин-2-карбоновую кислоту;
(2S, 4R) 4-бензамидо-1-(2-(2,2,2-трифторацетамидо)ацетил)-пирролидин-2-карбоновую кислоту;
(2S,4R)4-бензамидо-1-(2-трет-бутоксикарбониламино)ацетил)-пирролидин-2-карбоновую кислоту; или
(2S,4R) 4-бензамидо-1-(2-формамидоацетил)-пирролидин-2-карбоновую кислоту или его фармацевтически приемлемую соль.
14. Соединение по п.1, представляющее собой 1-(2-аминоацетил)-4-бензоиламино-пирролидин-2-карбоновой кислоту или ее фармацевтически приемлемую соль.
15. Соединение по п.14, представляющее собой (2S,4R) 1-(2-аминоацетил)-4-бензоиламино-пирролидин-2-карбоновую кислоту или ее фармацевтически приемлемую соль.
16. Фармацевтическая композиция, проявляющая антиаритмическую активность, содержащая соединение по любому из пп.1-15 или его фармацевтически приемлемую соль и фармацевтически приемлемый носитель.
17. Способ лечения или профилактики патологического состояния, включающий введение субъекту, который в этом нуждается, терапевтически эффективного количества соединения или фармацевтической композиции по любому из пп.1-16, при этом патологическим состоянием является сердечно-сосудистое заболевание.
18. Способ по п.17, отличающийся тем, что сердечно-сосудистое заболевание выбирают из фибрилляции предсердий, трепетания предсердий, вентрикулярной тахикардии и вентрикулярной фибрилляции.
19. Применение соединения по любому из пп.1-15 для получения лекарственного средства для профилактики или лечения патологического состояния, при этом патологическим состоянием является сердечно-сосудистое заболевание.
20. Применение по п.19, отличающееся тем, что сердечно-сосудистое заболевание выбирают из фибрилляции предсердий, трепетания предсердий, вентрикулярной тахикардии и вентрикулярной фибрилляции.
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