RU2013132389A - Фосфорные производные в качестве модуляторов хемокиновых рецепторов - Google Patents

Фосфорные производные в качестве модуляторов хемокиновых рецепторов Download PDF

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RU2013132389A
RU2013132389A RU2013132389/04A RU2013132389A RU2013132389A RU 2013132389 A RU2013132389 A RU 2013132389A RU 2013132389/04 A RU2013132389/04 A RU 2013132389/04A RU 2013132389 A RU2013132389 A RU 2013132389A RU 2013132389 A RU2013132389 A RU 2013132389A
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chloro
phenyl
substituted
unsubstituted
trifluoromethyl
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RU2013132389/04A
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Хайцин ЮАНЬ
Ричард Л. БИРД
Сяося ЛЮ
Джон Е. ДОНЕЛЛО
Веена ВИСВАНАТ
Майкл Е. ГАРСТ
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Аллерган, Инк.
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Abstract

1. Соединение, имеющее Формулу I, его энантиомеры, диастереоизомеры, гидраты, сольваты, кристаллические формы и индивидуальные изомеры, таутомеры или их фармацевтически приемлемые соли:где Rявляется Н или замещенным или незамещенным Cвалкилом;Rявляется замещенным или незамещенным Cалкилом, замещенным или незамещенным ОСалкилом, замещенным или незамещенным гетероциклом, замещенным или незамещенным Сциклоалкилом, замещенным или незамещенным Сциклоалкенилом или замещенным или незамещенным Сарилом;Rявляется C-R;Rявляется C-R;Rявляется -P(O)R;Rявляется замещенным или незамещенным Cалкилом, замещенным или незамещенным гетероциклом, замещенным или незамещенным Сциклоалкилом, замещенным или незамещенным Сциклоалкенилом или замещенным или незамещенным Сарилом;Rявляется Н, замещенным или незамещенным Cалкилом, замещенным или незамещенным гетероциклом, замещенным или незамещенным Сциклоалкилом, замещенным или незамещенным Сциклоалкенилом, замещенным или незамещенным Сарилом, галогеном, замещенным или незамещенным OCалкилом, CN, Салкенилом, Салкинилом, C(O)R, NRRили гидроксилом;Rявляется Н, замещенным или незамещенным Cалкилом, галогеном, замещенным или незамещенным ОСалкилом, CN, Салкенилом, Салкинилом или C(O)R;Rявляется Н, замещенным или незамещенным Cалкилом, ОН, ОСалкилом или HNCалкилом;Rявляется Н или замещенным или незамещенным Cалкилом;Rявляется Н или замещенным или незамещенным Cалкилом;Rявляется Н или замещенным или незамещенным Cалкилом;Rявляется Н, замещенным или незамещенным Cалкилом, галогеном, ОСалкилом, CN, Салкенилом, Салкинилом, C(O)R, NRRили гидроксилом; иRявляется Н, замещенным или незамещенным Cалкилом, галогеном, O

Claims (15)

1. Соединение, имеющее Формулу I, его энантиомеры, диастереоизомеры, гидраты, сольваты, кристаллические формы и индивидуальные изомеры, таутомеры или их фармацевтически приемлемые соли:
Figure 00000001
где R1 является Н или замещенным или незамещенным C1-6валкилом;
R2 является замещенным или незамещенным C1-6алкилом, замещенным или незамещенным ОС1-6алкилом, замещенным или незамещенным гетероциклом, замещенным или незамещенным С3-8циклоалкилом, замещенным или незамещенным С3-8 циклоалкенилом или замещенным или незамещенным С6-10арилом;
R3 является C-R7;
R4 является C-R8;
R5 является -P(O)R10;
R6 является замещенным или незамещенным C1-6алкилом, замещенным или незамещенным гетероциклом, замещенным или незамещенным С3-6циклоалкилом, замещенным или незамещенным С3-8циклоалкенилом или замещенным или незамещенным С6-10арилом;
R7 является Н, замещенным или незамещенным C1-6алкилом, замещенным или незамещенным гетероциклом, замещенным или незамещенным С3-8циклоалкилом, замещенным или незамещенным С3-8циклоалкенилом, замещенным или незамещенным С6-10арилом, галогеном, замещенным или незамещенным OC1-6алкилом, CN, С2-6алкенилом, С2-6алкинилом, C(O)R12, NR13R14 или гидроксилом;
R8 является Н, замещенным или незамещенным C1-6алкилом, галогеном, замещенным или незамещенным ОС1-6алкилом, CN, С2-6алкенилом, С2-6алкинилом или C(O)R12;
R10 является Н, замещенным или незамещенным C1-6алкилом, ОН, ОС1-6алкилом или HNC1-3алкилом;
R12 является Н или замещенным или незамещенным C1-6алкилом;
R13 является Н или замещенным или незамещенным C1-6алкилом;
R14 является Н или замещенным или незамещенным C1-6алкилом;
R15 является Н, замещенным или незамещенным C1-6алкилом, галогеном, ОС1-6алкилом, CN, С2-6алкенилом, С2-6алкинилом, C(O)R12, NR13R14 или гидроксилом; и
R16 является Н, замещенным или незамещенным C1-6алкилом, галогеном, OC1-6алкилом, CN, С2-6алкенилом, С2-6алкинилом, C(O)R12, NR13R14 или гидроксилом.
2. Соединение по п.1, отличающееся тем, что:
R1 является Н;
R2 является замещенным или незамещенным C1-6алкилом, замещенным или незамещенным ОС1-6алкилом, замещенным или незамещенным гетероциклом или замещенным или незамещенным фенилом;
R3 является C-R7;
R4 является C-R8;
R5 является -P(O)R10;
R6 является замещенным или незамещенным фенилом;
R7 является Н, замещенным или незамещенным C1-6алкилом или галогеном;
R8 является Н, замещенным или незамещенным C1-6алкилом или галогеном;
R10 является замещенным или незамещенным C1-6алкилом, ОН или является замещенным или незамещенным ОС1-6алкилом;
R15 является Н; и
R16 является Н.
3. Соединение по п.2, отличающееся тем, что:
R2 является н-бутокси, 4-оксопиперидин-1-илом, морфолин-4-илом, фенилом, метилом, 2,5-диметилфенилом или метокси.
4. Соединение по п.2, отличающееся тем, что:
R10 является н-бутокси, ОН, этокси или метилом.
5. Соединение по п.2, отличающееся тем, что:
R7 является галогеном.
6. Соединение по п.5, отличающееся тем, что:
R7 является хлором.
7. Соединение по п.2, отличающееся тем, что:
R6 является замещенным или незамещенным фенилом.
8. Соединение по п.7, отличающееся тем, что:
R6 является 4-хлор-3-фторметилфенилом.
9. Соединение по п.2, отличающееся тем, что:
R1 является Н;
R2 является н-бутокси, 4-оксопиперидин-1-илом, морфолин-4-илом, фенилом, метилом, 2,5-диметилфенилом или метокси;
R3 является C-R7;
R4 является C-R8;
R5 является -P(O)R10;
R6 является 4-хлор-3-фторметилфенилом;
R7 является хлором;
R8 является Н;
R10 является н-бутокси, ОН, этокси или метилом;
R15 является Н; и
R16 является Н.
10. Соединение по п.1, отличающееся тем, что соединение выбрано из:
Этил[4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]метилфосфината;
Дибутил[4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]фосфоната;
Диэтил(4-хлор-2-(4-хлор-3-(трифторметил)фенилсульфонамидо)фенил)фосфоната;
Метил гидро[4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]фосфоната;
[4-Хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]метилфосфиновой кислоты;
4-Хлор-N-{5-хлор-2-[метил(морфолин-4-ил)фосфорил]фенил}-3-(трифторметил)бензолсульфонамида;
4-хлор-N-{5-хлор-2-[метил(4-оксопиперидин-1-ил)фосфорил]фенил}-3-(трифторметил)бензолсульфонамида;
бутил гидро[4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]фосфоната;
этил гидро(4-хлор-2-(4-хлор-3-(трифторметил)фенилсульфонамидо)фенил) фосфоната;
бутил [4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил](4-оксопиперидин-1-ил)фосфината;
этил [4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]морфолин-4-илметилфосфината;
метил [4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил](4-оксопиперидин-1-ил)фосфината;
Этил (4-хлор-2-(4-хлор-3-(трифторметил)фенилсульфонамидо)фенил)(фенил)фосфината;
этил [4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил](2,5-диметилфенил)фосфината;
4-хлор-N-[5-хлор-2-(диметилфосфорил)фенил]-3-(трифторметил)бензолсульфонамида;
[4-Хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]фенилфосфиновой кислоты; и
[4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил](2,5-диметилфенил)фосфиновой кислоты.
11. Фармацевтическая композиция, включающая в качестве активного ингредиента терапевтически эффективное количество соединения по п.1 и фармацевтически приемлемый адъювант, разбавители или носитель.
12. Фармацевтическая композиция по п.11, отличающаяся тем, что соединение выбрано из:
Этил [4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]метилфосфината;
Дибутил [4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]фосфоната;
Диэтил (4-хлор-2-(4-хлор-3-(трифторметил)фенилсульфонамидо)фенил)фосфоната;
Метил гидро[4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]фосфоната;
[4-Хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]метилфосфиновой кислоты;
4-Хлор-N-{5-хлор-2-[метил(морфолин-4-ил)фосфорил]фенил}-3-(трифторметил)бензолсульфонамида;
4-хлор-N-{5-хлор-2-[метил(4-оксопиперидин-1-ил)фосфорил]фенил}-3-(трифторметил)бензолсульфонамида;
бутил гидро[4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]фосфоната;
этил гидро(4-хлор-2-(4-хлор-3-(трифторметил)фенилсульфонамидо)фенил)фосфоната;
бутил [4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил](4-оксопиперидин-1-ил)фосфината;
этил [4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]морфолин-4-илметилфосфината;
метил [4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил](4-оксопиперидин-1-ил)фосфината;
Этил (4-хлор-2-(4-хлор-3-(трифторметил)фенилсульфонамидо)фенил)(фенил)фосфината;
этил [4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил](2,5-диметилфенил)фосфината;
4-хлор-N-[5-хлор-2-(диметилфосфорил)фенил]-3-(трифторметил)бензолсульфонамида;
[4-Хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил]фенилфосфиновой кислоты;
[4-хлор-2-({[4-хлор-3-(трифторметил)фенил]сульфонил}амино)фенил](2,5-диметилфенил)фосфиновой кислоты.
13. Способ лечения расстройства, связанного с модулированием хемокинового рецептора, который включает введение млекопитающему, нуждающемуся в этом, фармацевтической композиции, включающей терапевтически эффективное количество, по меньшей мере, одного соединения Формулы I
Figure 00000001
где R1 является Н;
R2 является замещенным или незамещенным C1-6алкилом, замещенным или незамещенным ОС1-6алкилом, замещенным или незамещенным гетероциклом или замещенным или незамещенным фенилом;
R3 является C-R7;
R4 является C-R8;
R5 является -P(O)R10;
R6 является замещенным или незамещенным фенилом;
R7 является Н, замещенным или незамещенным C1-6алкилом или галогеном;
R8 является Н, замещенным или незамещенным C1-6алкилом или галогеном;
R10 является замещенным или незамещенным C1-6алкилом, ОН или является замещенным или незамещенным ОС1-6алкилом;
R15 является Н; и
R16 является H.
14. Способ по п.13, отличающийся тем, что фармацевтическая композиция вводится млекопитающему для лечения воспалительных заболеваний глаз и кожных воспалительных заболеваний и состояний.
15. Способ по п.14, отличающийся тем, что млекопитающим является человек.
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