RU2010101633A - Новое сульфонамидное производное малоновой кислоты и его фармацевтическое применение - Google Patents

Новое сульфонамидное производное малоновой кислоты и его фармацевтическое применение Download PDF

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RU2010101633A
RU2010101633A RU2010101633/04A RU2010101633A RU2010101633A RU 2010101633 A RU2010101633 A RU 2010101633A RU 2010101633/04 A RU2010101633/04 A RU 2010101633/04A RU 2010101633 A RU2010101633 A RU 2010101633A RU 2010101633 A RU2010101633 A RU 2010101633A
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Russia
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optionally substituted
alkyl
malonamide
amino
naphthylsulfonyl
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RU2010101633/04A
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English (en)
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RU2462454C2 (ru
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Томохиро ЙОСИДА (JP)
Томохиро Йосида
Хироси САКАСИТА (JP)
Хироси Сакасита
Ацуси НУМАТА (JP)
Ацуси НУМАТА
Саори ТАХАРА (JP)
Саори ТАХАРА
Хисаси КАВАСУМИ (JP)
Хисаси КАВАСУМИ
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Мицубиси Танабе Фарма Корпорейшн (Jp)
Мицубиси Танабе Фарма Корпорейшн
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    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract

1. Производное сульфонилмалонамида, представленное следующей формулой (I) ! ! где R1 представляет собой необязательно замещенный C1-8 алкил, необязательно замещенный C2-6 алкенил, необязательно замещенный C2-6 алкинил, необязательно замещенный C3-10 циклоалкил, необязательно замещенный C3-10 циклоалкил C1-6 алкил, необязательно замещенный гетероцикл, необязательно замещенный арил, необязательно замещенный арил C1-6 алкил, необязательно замещенный арилокси C1-6 алкил, необязательно замещенный арил C2-6 алкенил, необязательно замещенный гетероарил, необязательно замещенный гетероарил C1-6 алкил, необязательно замещенный гетероарилокси C1-6 алкил или необязательно замещенный гетероарил C2-6 алкенил; ! один из R2 и R3 представляет собой атом водорода или атом галогена, а другой представляет собой атом галогена, необязательно замещенный C1-6 алкил, необязательно замещенный C1-6 алкокси, необязательно замещенный C2-6 алкенил, необязательно замещенный C2-6 алкинил, -(CH2)n-С(O)-NR5R6 (где n представляет собой целое число от 1 до 6, R5 и R6 являются одинаковыми или разными, и каждый представляет собой атом водорода, C1-6 алкил, необязательно замещенный арил или необязательно замещенный гетероарил, или R5 и R6 вместе с соединенным с ними атомом азота необязательно образуют необязательно замещенный циклический амино), необязательно замещенный C3-10 циклоалкил, необязательно замещенный гетероцикл, необязательно замещенный C3-10 циклоалкил C1-6 алкил, необязательно замещенный гетероцикл C1-6 алкил, необязательно замещенный арил, необязательно замещенный арил C1-6 алкил, необязательно замещенный арилокси C1-6 алкил, необязательно замещенный арил C2-6 алкенил, необязат�

Claims (16)

1. Производное сульфонилмалонамида, представленное следующей формулой (I)
Figure 00000001
где R1 представляет собой необязательно замещенный C1-8 алкил, необязательно замещенный C2-6 алкенил, необязательно замещенный C2-6 алкинил, необязательно замещенный C3-10 циклоалкил, необязательно замещенный C3-10 циклоалкил C1-6 алкил, необязательно замещенный гетероцикл, необязательно замещенный арил, необязательно замещенный арил C1-6 алкил, необязательно замещенный арилокси C1-6 алкил, необязательно замещенный арил C2-6 алкенил, необязательно замещенный гетероарил, необязательно замещенный гетероарил C1-6 алкил, необязательно замещенный гетероарилокси C1-6 алкил или необязательно замещенный гетероарил C2-6 алкенил;
один из R2 и R3 представляет собой атом водорода или атом галогена, а другой представляет собой атом галогена, необязательно замещенный C1-6 алкил, необязательно замещенный C1-6 алкокси, необязательно замещенный C2-6 алкенил, необязательно замещенный C2-6 алкинил, -(CH2)n-С(O)-NR5R6 (где n представляет собой целое число от 1 до 6, R5 и R6 являются одинаковыми или разными, и каждый представляет собой атом водорода, C1-6 алкил, необязательно замещенный арил или необязательно замещенный гетероарил, или R5 и R6 вместе с соединенным с ними атомом азота необязательно образуют необязательно замещенный циклический амино), необязательно замещенный C3-10 циклоалкил, необязательно замещенный гетероцикл, необязательно замещенный C3-10 циклоалкил C1-6 алкил, необязательно замещенный гетероцикл C1-6 алкил, необязательно замещенный арил, необязательно замещенный арил C1-6 алкил, необязательно замещенный арилокси C1-6 алкил, необязательно замещенный арил C2-6 алкенил, необязательно замещенный гетероарил, необязательно замещенный гетероарил C1-6 алкил, необязательно замещенный гетероарилокси C1-6 алкил или необязательно замещенный гетероарил C2-6 алкенил, или R2 и R3 вместе с соединенным с ними атомом углерода необязательно образуют C=CX'Y' (где X' и Y' являются одинаковыми или разными, и каждый представляет собой атом водорода, необязательно замещенный C1-6 алкил, необязательно замещенный арил или необязательно замещенный гетероарил), или необязательно замещенный C3-10 циклоалкил; и
R4 представляет собой следующую формулу
Figure 00000002
где R7 и R8 являются одинаковыми или разными, и каждый представляет собой атом водорода, необязательно замещенный C1-6 алкил, необязательно замещенный C2-6 алкенил, необязательно замещенный арил, необязательно замещенный арил C1-6 алкил, необязательно замещенный гетероарил, необязательно замещенный гетероарил C1-6 алкил, необязательно замещенный C3-10 циклоалкил или необязательно замещенный гетероцикл, или R7 и R8 вместе с соединенным с ними атомом азота необязательно образуют необязательно замещенный циклический амино,
или его фармакологически приемлемая соль, или его сольват.
2. Производное сульфонилмалонамида по п.1, где R1 представляет собой необязательно замещенный нафтил, необязательно замещенный бифенил, необязательно замещенный фенил, необязательно замещенный тиофен, необязательно замещенный фенил C1-6 алкил, необязательно замещенный фенокси C1-6 алкил, необязательно замещенный тиазолил C1-6 алкил, необязательно замещенный C1-8 алкил, необязательно замещенный C2-6 алкенил, необязательно замещенный C3-10 циклоалкил или следующую формулу
Figure 00000003
где Ar представляет собой необязательно замещенный фенил, необязательно замещенный пиридил или необязательно замещенный тиазолил,
или его фармакологически приемлемая соль, или его сольват.
3. Производное сульфонилмалонамида по п.1, где один из R2 и R3 представляет собой атом водорода, а другой представляет собой C1-6 алкил, аллил, пренил, 2-пропинил, циклопентил, -CH2-R9 (где R9 представляет собой циклопропил, циано, необязательно замещенный циклогексил, необязательно N-замещенный 4-пиперидинил или -CO-NR5R6, где R5 и R6 такие, как определено выше по п.1), -(CH2)2-R9' (где R9' представляет собой циано, C1-6 алкокси, C1-6 алкилтио, C1-6 алкилсульфинил, C1-6 алкилсульфонил, N-замещенный-4-пиперидинил или N-замещенный-4-пиперазинил), -(CH2)n-Ar1 или -CH2-CH=CH-Ar1 (где n представляет собой целое число от 0 до 6, и Ar1 представляет собой необязательно замещенный арил или необязательно замещенный гетероарил),
или его фармакологически приемлемая соль, или его сольват.
4. Производное сульфонилмалонамида по п.1, где R4 представлен следующей формулой
Figure 00000004
где R10 и R11 являются одинаковыми или разными, и каждый представляет собой необязательно замещенный C1-6 алкил, необязательно замещенный C2-6 алкенил, необязательно замещенный арил, необязательно замещенный арил C1-6 алкил, необязательно замещенный гетероарил, необязательно замещенный C3-10 циклоалкил или необязательно замещенный гетероцикл, или R10 и R11 вместе с соединенным с ними атомом азота необязательно образуют необязательно замещенный циклический амино,
или его фармакологически приемлемая соль, или его сольват.
5. Лиганд AT2 рецептора, содержащий производное сульфонилмалонамида по любому из пп.1-4 или его фармакологически приемлемую соль, или его сольват.
6. Производное сульфонилмалонамида по п.1, которое представлено следующей формулой (II)
Figure 00000005
где R12 представляет собой 2-нафтил, транс-β-стирил, фенетил, 3-феноксипропил или 4-фенилбутил;
один из R13 и R14 представляет собой атом водорода, а другой представляет собой изопропил, изобутил, неопентил, аллил, -CH2-R16, где R16 представляет собой необязательно замещенный C3-10 циклоалкил, необязательно замещенный гетероцикл или -CO-NR5R6 (где R5 и R6 такие, как определено выше по п.1), -(CH2)2-R16' (где R16' представляет собой циано или C1-6 алкокси) или -(CH2)n-Ar2 (где n представляет собой целое число от 1 до 3, и Ar2 представляет собой замещенный фенил или необязательно замещенный гетероарил), или R13 и R14 вместе с соединенным с ними атомом углерода необязательно образуют следующую формулу
Figure 00000006
, и
R15 представляет собой ди(C1-6 алкил)амино или следующую формулу
Figure 00000007
где Z представляет собой атом водорода, атом галогена или трифторметил, Y представляет собой атом азота или CH, R17 представляет собой этил, изопропил или 3-пентил при условии, что когда Y представляет собой атом азота, то Z представляет собой атом водорода,
или его фармакологически приемлемая соль, или его сольват.
7. Производное сульфонилмалонамида по п.6, где Ar2 для R13 или R14 представляет собой замещенный фенил, представленный следующей формулой
Figure 00000008
где X представляет собой атом фтора, атом хлора, атом брома, циано, нитро, амино (исключая замещение в орто-положении), -NHCOAr3, -NHCOOAr3, -NHCONHAr3, -NHSO2Ar3, -OAr3 (где Ar3 представляет собой необязательно замещенный арил или необязательно замещенный гетероарил), -NHCOR18 (где R18 представляет собой необязательно замещенный C1-6 алкил, необязательно замещенный C3-10 циклоалкил или необязательно замещенный гетероцикл), необязательно замещенный C1-6 алкоксикарбонил, ди(C1-6 алкил)амино, необязательно замещенный C1-6 алкокси, необязательно замещенный гетероцикл, необязательно замещенный арил или необязательно замещенный гетероарил,
или его фармакологически приемлемая соль, или его сольват.
8. Производное сульфонилмалонамида по п.6, которое представлено следующей формулой (III)
Figure 00000009
где R12, R17, Y и Z такие, как определено по п.6, один из R19 и R20 представляет собой атом водорода, а другой представляет собой изопропил, изобутил, неопентил, аллил, циклопропилметил или -CH2-Ar2, где Ar2 такой, как определено по п.6,
или его фармакологически приемлемая соль, или его сольват.
9. Производное сульфонилмалонамида по п.6, которое представлено следующей формулой (IV)
Figure 00000010
где n представляет собой целое число от 1 до 3, Ar2 такой, как определено по п.6,
или его фармакологически приемлемая соль, или его сольват.
10. Производное сульфонилмалонамида по п.9, где Ar2 представляет собой замещенный фенил, представленный следующей формулой
Figure 00000011
где R21 представляет собой атом фтора, атом хлора, нитро, циано, амино (исключая замещение в орто-положении), диметиламино, метокси, трифторметокси, метоксикарбонил, фенил, 2-пиридилокси, 1-имидазолил, 2-изоиндолинил, 1-оксо-2-изоиндолинил или следующую формулу
где Ar3 такой, как определено по п.7,
или его фармакологически приемлемая соль, или его сольват.
11. Производное сульфонилмалонамида по п.9, где Ar2 представляет собой замещенный фенил, представленный следующей формулой
Figure 00000013
где Ar4 представляет собой 2-тиенил, 2-фурил, 4-пиридил, 3-пиридил, 2-пиридил или следующую формулу
Figure 00000014
где R22 и R25 являются одинаковыми или разными, и каждый представляет собой атом водорода, амино, атом фтора, гидрокси, метокси, метил или атом хлора, R23 представляет собой атом водорода или атом фтора, R24 представляет собой атом водорода, атом фтора, атом хлора, метил, амино, метокси или циано, и n представляет собой 1,
или его фармакологически приемлемая соль, или его сольват.
12. Производное сульфонилмалонамида по п.6, которое представляет собой следующее соединение:
N,N-диэтил-2-{4-[(2,6-дифторбензоил)амино]бензил}-N'-(2-нафтилсульфонил)малонамид,
(2S)-2-[4-(бензоиламино)бензил]-N,N-диэтил-N'-(2-нафтилсульфонил)малонамид,
(2S)-N,N-диэтил-2-{4-[(2-фторбензоил)амино]бензил}-N'-(2-нафтилсульфонил)малонамид,
(2S)-N,N-диэтил-2-{4-[(3-фторбензоил)амино]бензил}-N'-(2-нафтилсульфонил)малонамид,
(2S)-N,N-диэтил-2-{4-[(2,4-дифторбензоил)амино]бензил}-N'-(2-нафтилсульфонил)малонамид,
(2S)-N,N-диэтил-2-{4-[(4-метилбензоил)амино]бензил}-N'-(2-нафтилсульфонил)малонамид,
(2S)-N,N-диэтил-N'-(2-нафтилсульфонил)-2-{4-[(2-тиеноил)амино]бензил}малонамид,
(2S)-N,N-диэтил-2-{4-[(2-фуроил)амино]бензил}-N'-(2-нафтилсульфонил)малонамид,
(2S)-2-{4-[(2-амино-5-фторбензоил)амино]бензил}-N,N-диэтил-N'-(2-нафтилсульфонил)малонамид,
(2S)-2-{4-[(2-амино-6-фторбензоил)амино]бензил}-N,N-диэтил-N'-(2-нафтилсульфонил)малонамид,
(2S)-N,N-диэтил-N'-(2-нафтилсульфонил)-2-{4-[(2-пиридилкарбонил)амино]бензил}малонамид,
(2S)-2-{4-[(2-амино-4-хлорбензоил)амино]бензил}-N,N-диэтил-N'-(2-нафтилсульфонил)малонамид,
(2S)-2-{4-[(2-аминобензоил)амино]бензил}-N,N-диэтил-N'-(2-нафтилсульфонил)малонамид,
(2S)-2-{4-[(2-амино-5-хлорбензоил)амино]бензил}-N,N-диэтил-N'-(2-нафтилсульфонил)малонамид,
(2S)-2-{4-[(2-амино-4,5-дифторбензоил)амино]бензил}-N,N-диэтил-N'-(2-нафтилсульфонил)малонамид,
(2S)-2-{4-[(2-амино-4-фторбензоил)амино]бензил}-N,N-диэтил-N'-(2-нафтилсульфонил)малонамид,
(2S)-2-{4-[(2-амино-5-метилбензоил)амино]бензил}-N,N-диэтил-N'-(2-нафтилсульфонил)малонамид,
2-(4-фторбензил)-N-изопропил-N-(3-пиридил)-N'-((E)-стирилсульфонил)малонамид,
2-аллил-N-(4-фторфенил)-N-изопропил-N'-((E)-стирилсульфонил)малонамид,
N-(4-фторфенил)-2-изобутил-N-изопропил-N'-((E)-стирилсульфонил)малонамид,
N-(4-фторфенил)-2-изобутил-N-изопропил-N'-фенетилсульфонилмалонамид,
N-(4-фторфенил)-2-изобутил-N-изопропил-N'-(2-нафтилсульфонил)малонамид,
(2S или 2R)-2-циклопропилметил-N-(4-фторфенил)-N-изопропил-N'-((E)-2-стирилсульфонил)малонамид,
2-циклопропилметил-N-(4-фторфенил)-N-изопропил-N'-фенетилсульфонилмалонамид или
2-циклопропилметил-N-(4-фторфенил)-N-изопропил-N'-(2-нафтилсульфонил)малонамид,
или его фармакологически приемлемая соль, или его сольват.
13. Фармацевтическая композиция, содержащая производное сульфонилмалонамида по любому из пп.6-12 или его фармакологически приемлемую соль, или его сольват, в качестве активного компонента.
14. Агонист AT2 рецептора, содержащий производное сульфонилмалонамида по любому из пп.6-12 или его фармакологически приемлемую соль, или его сольват.
15. Агонист AT2 рецептора по п.14, содержащий производное сульфонилмалонамида по п.12 или его фармакологически приемлемую соль, или его сольват.
16. Агонист AT2 рецептора по п.15, который является селективным к AT2 рецептору.
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