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RU2005111985A - Производные 4-(фенил-пиперазинил-метил)бензамида и их применение для лечения боли или желудочно-кишечных расстройств - Google Patents

Производные 4-(фенил-пиперазинил-метил)бензамида и их применение для лечения боли или желудочно-кишечных расстройств Download PDF

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RU2005111985A
RU2005111985A RU2005111985/04A RU2005111985A RU2005111985A RU 2005111985 A RU2005111985 A RU 2005111985A RU 2005111985/04 A RU2005111985/04 A RU 2005111985/04A RU 2005111985 A RU2005111985 A RU 2005111985A RU 2005111985 A RU2005111985 A RU 2005111985A
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alkyl
methyl
phenyl
diethylamino
carbonyl
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Уиль м БРАУН (CA)
Уильям БРАУН
Эндрю ГРИФФИН (CA)
Эндрю Гриффин
Пол ДЖОУНС (CA)
Пол ДЖОУНС
Дэниел ПЭЙДЖ (CA)
Дэниел ПЭЙДЖ
Никлас ПЛОБЕК (SE)
Никлас ПЛОБЕК
Кристофер УОЛПОЛ (CA)
Кристофер Уолпол
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Астразенека Аб (Se)
Астразенека Аб
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Claims (15)

1. Соединение формулы (I), его фармацевтически приемлемая соль, его диастереомеры, энантиомеры или их смеси,
Figure 00000001
где R1 выбран из -Н, С6-10арила, С2-6гетероарила, С6-10арил-С1-4алкила и С2-6гетероарил-С1-4алкила, причем указанные С6-10арил, С2-6гетероарил, С6-10арил-С1-4алкил и С2-6гетероарил-С1-4алкил возможно замещены одной или более чем одной группой, выбранной из -R, -NO2, -OR, Cl, -Br, -I, -F, -CF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород или С1-6алкил;
R2 выбран из -Н, С1-6алкила и С3-6циклоалкила, причем указанные С1-6алкил и С3-6циклоалкил возможно замещены одной или более чем одной группой, выбранной из -OR, -Cl, -Br, -I, -F, -CF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3H, -SO2R, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород или С1-6алкил; и
R3 выбран из C1-6алкила и С3-6циклоалкила, причем указанные С1-6алкил и С3-6циклоалкил возможно замещены одной или более чем одной группой, выбранной из -OR, -Cl, -Br, -I, -F, -CF3, -C(=C)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород или С1-6алкил.
2. Соединение по п.1, где
R1 представляет собой -CH2-R4, где R4 выбран из фенила, пиридила, тиенила, фурила, имидазолила, триазолила, пирролила, тиазолила и N-оксидо-пиридила, причем указанные фенил, пиридил, тиенил, фурил, имидазолил, триазолил, пирролил, тиазолил и N-оксидо-пиридил возможно замещены одной или более чем одной группой, выбранной из С1-6алкила, галогенированного C1-6алкила, -NO2, -CF3, С1-6алкокси, хлоро, фторо, бромо и йодо;
R2 выбран из -Н и С1-3алкила; и
R3 выбран из С1-6алкила и С3-6циклоалкила.
3. Соединение по п.2,
где R4 выбран из фенила, пиридила, тиенила, фурила, имидазолила, пирролила и тиазолила;
R2 выбран из -Н и метила; и
R3 выбран из метила, этила, пропила и изопропила.
4. Соединение по п.1, где
R1 представляет собой -Н;
R2 выбран из -Н и С1-3алкила; и
R3 выбран из С1-6алкила и С3-6циклоалкила.
5. Соединение по п.1, выбранное из
метил-3-[(4-[(диэтиламино)карбонил]фенил)(4-бензил-пиперазин-1-ил)метил]фенилкарбамата;
метил-3-{{4-[(диэтиламино)карбонил]фенил}[4-(тиен-2-илметил)пиперазин-1-ил]метил}фенилкарбамата;
метил-3-{{4-[(диэтиламино)карбонил]фенил}[4-(тиен-3-илметил)пиперазин-1-ил]метил}фенилкарбамата;
метил-3-{{4-[(диэтиламино)карбонил]фенил}[4-(2-фурилметил)пиперазин-1-ил]метил}фенилкарбамата;
метил-3-{{4-[(диэтиламино)карбонил]фенил}[4-(3-фурилметил)пиперазин-1-ил]метил}фенилкарбамата;
метил-3-{{4-[(диэтиламино)карбонил]фенил}[4-(1Н-имидазол-2-илметил)пиперазин-1-ил]метил}фенилкарбамата;
метил-3-{{4-[(диэтиламино)карбонил]фенил}[4-(пиридин-2-илметил)пиперазин-1-ил]метил}фенилкарбамата;
метил-3-{{4-[(диэтиламино)карбонил]фенил}[4-(пиридин-4-ил-метил)пиперазин-1-ил}метил}фенилкарбамата;
метил-3-{{4-[(диэтиламино)карбонил]фенил}[4-(1,3-тиазол-2-илметил)пиперазин-1-ил]метил}фенилкарбамата;
метилового эфира [3-[[4-[(диэтиламино)карбонил]фенил][4-(фенилметил)-1-пиперазинил]метил]фенил]-карбаминовой кислоты;
метилового эфира [3-[(S)-[4-[(диэтиламино)карбонил]фенил][4-(3-пиридинилметил)-1-пиперазинил]метил]фенил]-карбаминовой кислоты;
метилового эфира [3-[(S)-[4-[(диэтиламино)карбонил]фенил][4-(2-тиазолилметил)-1-пиперазинил]метил]фенил]-карбаминовой кислоты;
метил-3-{(R)-{4-[(диэтиламино)карбонил]фенил}[4-(1,3-тиазол-4-илметил)пиперазин-1-ил]метил}фенилкарбамата;
метил-3-{(S)-{4-[(диэтиламино)карбонил]фенил}[4-(1,3-тиазол-4-илметил)пиперазин-1-ил]метил}фенилкарбамата;
метил-3-{(R)-{4-[(диэтиламино)карбонил]фенил}[4-(1,3-тиазол-5-илметил)пиперазин-1-ил]метил}фенилкарбамата;
метил-3-{(S)-{4-[(диэтиламино)карбонил]фенил}[4-(1,3-тиазол-5-илметил)пиперазин-1-ил]метил}фенилкарбамата;
метилового эфира [3-[[4-[(диэтиламино)карбонил]фенил]-1-пиперазинилметил]фенил]-карбаминовой кислоты;
его энантиомеров; и его фармацевтически приемлемых солей.
6. Соединение по любому из пп.1-5 для применения в качестве лекарства.
7. Применение соединения по любому из пп.1-5 в изготовлении лекарства для лечения боли, тревоги или функциональных желудочно-кишечных расстройств.
8. Фармацевтическая композиция, содержащая соединение по любому из пп.1-5 и фармацевтически приемлемый носитель.
9. Способ лечения боли у теплокровного животного, включающий введение указанному животному, нуждающемуся в таком лечении, терапевтически эффективного количества соединения по любому из пп.1-5.
10. Способ лечения функциональных желудочно-кишечных расстройств у теплокровного животного, включающий введение указанному животному, нуждающемуся в таком лечении, терапевтически эффективного количества соединения по любому из пп.1-5.
11. Способ лечения тревоги у теплокровного животного, включающий введение указанному животному, нуждающемуся в таком лечении, терапевтически эффективного количества соединения по любому из пп.1-5.
12. Способ получения соединения формулы II, включающий
Figure 00000002
а) взаимодействие соединения формулы III
Figure 00000003
с соединением формулы IV
Figure 00000004
в присутствие бензотриазола; и
б) взаимодействие продукта, образовавшегося на стадии (а) с соединением формулы V с образованием соединения формулы II,
Figure 00000005
где R8 выбран из С1-6алкил-O-С(=O)-, С6-10арил-С1-4алкила и С2-6гетероарил-С1-4алкила, причем указанные С1-6алкил-O-С(=O)-, С6-10арил-С1-4алкил и С2-6гетероарил-С1-4алкил возможно замещены одной или более чем одной группой, выбранной из C1-6алкила, галогенированного C1-6алкила, -NO2, -CF3, С1-6алкокси, хлоро, фторо, бромо и йодо;
М выбран из Li, Na, К, -ZnX1 и -MgX1, где X1 представляет собой галоген; и
R9 выбран из водорода, -R, -NO2, -OR, Cl, -Br, -I, -F, -CF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -S(=O)R, -CN, -OH, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород или С1-6гидрокарбил.
13. Способ получения соединения формулы VII
Figure 00000006
включающий
взаимодействие соединения формулы VIII
Figure 00000007
с С1-6алкилкарбаматом с образованием соединения формулы VII, где
R8 выбран из С1-6алкил-O-С(=O)-, С6-10арил-С1-4алкила и С2-6гетероарил-С1-4алкила, причем указанные С1-6алкил-O-С(=O)-, С6-10арил-С1-4алкил и С2-6гетероарил-С1-4алкил возможно замещены одной или более чем одной группой, выбранной из -OR, Cl, -Br, -I, -F, -CF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3H, -SO2R, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород или С1-6алкил;
Х выбран из галогена, трифлата и сульфонамида; и
R11 представляет собой C1-6алкил.
14. Способ получения соединения формулы X,
Figure 00000008
включающий
взаимодействие соединения формулы IX
Figure 00000009
с R4-CHO с образованием соединения формулы X, где
R4 выбран из фенила, пиридила, тиенила, фурила, имидазолила, триазолила, пирролила, тиазолила и N-оксидо-пиридила, причем указанные фенил, пиридил, тиенил, фурил, имидазолил, триазолил, пирролил, тиазолил и N-оксидо-пиридил возможно замещены одной или более чем одной группой, выбранной из C1-6алкила, галогенированного C1-6алкила, -NO2, -CF3, С1-6алкокси, хлоро, фторо, бромо и йодо;
R2 выбран из -Н, С1-6алкила и С3-6циклоалкила, причем указанные С1-6алкил и С3-6циклоалкил возможно замещены одной или более чем одной группой, выбранной из -OR, -Cl, -Br, -I, -F, -CF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород или С1-6алкил; и
R3 выбран из -Н, С1-6алкила и С3-6циклоалкила, причем указанные C1-6алкил и С3-6циклоалкил возможно замещены одной или более чем одной группой, выбранной из -OR, -Cl, -Br, -I, -F, -CF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -S(=O)R, -CN, -OH, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород или С1-6алкил.
15. Соединение формулы XI, его фармацевтически приемлемая соль, его диастереомеры, энантиомеры или их смеси,
Figure 00000010
где R1 выбран из -Н, С6-10арила, С2-6гетероарила, С6-10арил-С1-4алкила и С2-6гетероарил-С1-4алкила, причем указанные С6-10арил, С2-6гетероарил, С6-10арил-С1-4алкил и С2-6гетероарил-С1-4алкил возможно замещены одной или более чем одной группой, выбранной из -R, -NO2, -OR, Cl, -Br, -I, -F, -CF3, -C(=O)R, -C(=O)OH, -NH2, -SH, -NHR, -NR2, -SR, -SO3Н, -SO2R, -S(=O)R, -CN, -ОН, -C(=O)OR, -C(=O)NR2, -NRC(=O)R и -NRC(=O)-OR, где R независимо представляет собой водород или С1-6алкил.
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