RU2013128602A - Производные дифениламина: применение, способ синтеза и фрамацевтические композиции - Google Patents

Производные дифениламина: применение, способ синтеза и фрамацевтические композиции Download PDF

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RU2013128602A
RU2013128602A RU2013128602/04A RU2013128602A RU2013128602A RU 2013128602 A RU2013128602 A RU 2013128602A RU 2013128602/04 A RU2013128602/04 A RU 2013128602/04A RU 2013128602 A RU2013128602 A RU 2013128602A RU 2013128602 A RU2013128602 A RU 2013128602A
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group
alkyl
phenyl
cancer
formula
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RU2013128602/04A
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СОЛАНЕС Роса РОДЕС
ДОМИНГЕС Нефтали ГАРСИЯ
ОРТЕГА Беатрис ЛОПЕС
ДЕ МОН СОТО Мельчор АЛЬВАРЕС
ЛА ЭРА МАРТИНЕС Антонио ДЕ
МУНЬОС Ан МУНЬОС
ГОМЕС Франсиско ЛЕДО
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Фаэс Фарма, С.А.
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  • Pyridine Compounds (AREA)

Abstract

1. Соединение формулы (I) или его соль, пролекарство или сольват:где Ph обозначает фенил;n равно 2, 3 или 4;Rвыбран из группы, включающей атом водорода и C-Cалкил;Rобозначает радикал формулы -[[CH(R)]-R], где m равно 1;R, где предусмотрен, выбран из группы, включающей атом водорода, фенил и C-Cалкил;Rвыбран из группы, включающей радикалы: незамещенный гетероарил, замещенный гетероарил и замещенный арил,причем указанные заместители выбраны из группы, включающей C-Cалкил, C-Cарилалкил, фенил, 5- или 6-членный гетероарил, F, Cl, Br, I, трифторметил, циано, -N(R)(R), -OR, -SRили -C(O)R; где R, R, R, Rи Rнезависимо выбраны из атома водорода, C-Cалкила, фенила и трифторметила; илиесли Rи/или Rотличны от атома водорода, то Rтакже может обозначать незамещенный фенил; илиRи Rвместе с атомом азота, к которому они присоединены, образуют замещенную или незамещенную гетероарильную группу, в которой указанные заместители такие, как определено выше,при условии, что:2-[(4,4-дифенилбут-3-ениламино)метил]фенол,3-[(4,4-дифенилбут-3-ениламино)метил]-фенол,5-[(4,4-дифенилбут-3-ениламино)метил]-2-метоксифенол,4-[(4,4-дифенилбут-3-ениламино)метил]-2,6-дифторфенол,бензил-(5,5-дифенилпент-4-енил)этиламин,6-хлор-9-(4,4-дифенилбут-3-енил)-9H-пурин,9-(4,4-дифенилбут-3-енил)-9H-пурин-6-иламин, и5-(4,4-дифенилбут-3-енил)-4,5,6,7-тетрагидроизоксазоло[4,5-c]пиридин-3-ол не включены в формулу (I).2. Соединение по п.1, где каждый из указанных заместителей выбран из группы, включающей C-Cалкил, C-Cарилалкил, фенил, 5- или 6-членный гетероарил, F, Br, I, трифторметил, циано, -N(R)(R), -OR, -SRили -C(O)R; где R, R, Rи Rнезависимо выбраны из атома водорода, C-Cалкила, фенила и трифторметила и Rвыбран из группы, включающей C-Cалкил, фенил и трифторметил, при условии, что -N(R)(R) н�

Claims (14)

1. Соединение формулы (I) или его соль, пролекарство или сольват:
Figure 00000001
где Ph обозначает фенил;
n равно 2, 3 или 4;
R1 выбран из группы, включающей атом водорода и C1-C6 алкил;
R2 обозначает радикал формулы -[[CH(R3)]m-R4], где m равно 1;
R3, где предусмотрен, выбран из группы, включающей атом водорода, фенил и C1-C6 алкил;
R4 выбран из группы, включающей радикалы: незамещенный гетероарил, замещенный гетероарил и замещенный арил,
причем указанные заместители выбраны из группы, включающей C1-C6 алкил, C7-C11 арилалкил, фенил, 5- или 6-членный гетероарил, F, Cl, Br, I, трифторметил, циано, -N(Ra)(Rb), -ORc, -SRd или -C(O)Re; где Ra, Rb, Rc, Rd и Re независимо выбраны из атома водорода, C1-C6 алкила, фенила и трифторметила; или
если R1 и/или R3 отличны от атома водорода, то R4 также может обозначать незамещенный фенил; или
R1 и R2 вместе с атомом азота, к которому они присоединены, образуют замещенную или незамещенную гетероарильную группу, в которой указанные заместители такие, как определено выше,
при условии, что:
2-[(4,4-дифенилбут-3-ениламино)метил]фенол,
3-[(4,4-дифенилбут-3-ениламино)метил]-фенол,
5-[(4,4-дифенилбут-3-ениламино)метил]-2-метоксифенол,
4-[(4,4-дифенилбут-3-ениламино)метил]-2,6-дифторфенол,
бензил-(5,5-дифенилпент-4-енил)этиламин,
6-хлор-9-(4,4-дифенилбут-3-енил)-9H-пурин,
9-(4,4-дифенилбут-3-енил)-9H-пурин-6-иламин, и
5-(4,4-дифенилбут-3-енил)-4,5,6,7-тетрагидроизоксазоло[4,5-c]пиридин-3-ол не включены в формулу (I).
2. Соединение по п.1, где каждый из указанных заместителей выбран из группы, включающей C1-C6 алкил, C7-C11 арилалкил, фенил, 5- или 6-членный гетероарил, F, Br, I, трифторметил, циано, -N(Ra)(Rb), -ORc, -SRd или -C(O)Re; где Ra, Rb, Rd и Re независимо выбраны из атома водорода, C1-C6 алкила, фенила и трифторметила и Rc выбран из группы, включающей C1-C6 алкил, фенил и трифторметил, при условии, что -N(Ra)(Rb) не является NH2.
3. Соединение по п.1 или 2 формулы (IA) или его соль, пролекарство и/или сольват
Figure 00000002
где Ph, n, R1 и R4 такие, как определено в любом из предыдущих пунктов.
4. Соединение по п.3, где R4 обозначает незамещенный гетероарил или замещенный гетероарил, выбранный из группы, включающей тиенил, фурил, пиридил, 1H-бензимидазол, 9H-пурин, 1H-имидазол и 1H-пиразоло[3,4-d]пиримидин.
5. Соединение по п.1, где R4 обозначает группу формулы (V) или (VI)
Figure 00000003
где A и B независимо выбраны из -CH- и -N-;
D независимо выбран из группы, включающей -O-, -S- и -NH-;
p равно целому числу 0, 1, 2 или 3;
каждый R5 выбран из группы, включающей C1-C3 алкил, фенил, фенилметил,
5- или 6-членный гетероарил, F, Br, I, трифторметил, -N(Ra)(Rb), -SRd или -C(O)Re; где Ra, Rb, Rd и Re независимо выбраны из атома водорода, C1-C3 алкила, фенила и трифторметила, при условии, что в соединении формулы (V) -N(Ra)(Rb) не является -NH2 ;
причем указанная группа формулы (V) или (VI) присоединена к остатку молекулы через любое из свободных положений.
6. Соединение по п.1, где R1 и R2 вместе с атомом азота, к которому они присоединены, образуют радикал, выбранный из группы, включающей 1H-бензимидазол, 9H-пурин, 1H-имидазол и 1H-пиразоло[3,4-d]пиримидин.
7. Соединение по п.1, где R4 обозначает группу формулы (VII)
Figure 00000004
где R6 выбран из группы, включающей -OCF3, OC1-С3алкил, F, Cl, Br, I и -CN; и q равно целому числу 1, 2 или 3, и указанная группа формулы (VII) присоединена к остатку молекулы через любое из свободных положений.
8. Соединение по п.1, где R1 обозначает атом водорода или метил.
9. Соединение по п.1, выбранное из группы, включающей:
Figure 00000005
Figure 00000006
Figure 00000007
Figure 00000008
или его соль, пролекарство и/или сольват.
10. Фармацевтическая композиция, содержащая соединение формулы I или его фармацевтически приемлемую соль, пролекарство или сольват и, по меньшей мере, один фармацевтически приемлемый носитель.
11. Применение соединения формулы (I) или его фармацевтически приемлемой соли, пролекарства или сольвата:
Figure 00000009
где Ph обозначает фенил;
n равно 2, 3 или 4;
R1 выбран из группы, включающей атом водорода и C1-C6 алкил;
R2 обозначает радикал формулы -[[CH(R3)]m-R4], где
m равно целому числу 1, 0 или 2;
каждый R3, где предусмотрен, выбран из группы, включающей атом водорода и C1-C6 алкил;
R4 выбран из группы, включающей радикалы: незамещенный гетероарил, замещенный гетероарил, незамещенный арил и замещенный арил,
причем указанные заместители выбраны из группы, включающей C1-C6 алкил, C7-C11 арилалкил, фенил, 5- или 6-членный гетероарил, F, Cl, Br, I, трифторметил, циано, -N(Ra)(Rb), -ORc, -SRd или -C(O)Re; где Ra, Rb, Rc, Rd и Re независимо выбраны из атома водорода, C1-C6 алкила, фенила и трифторметила; или
R1 и R2 вместе с атомом азота, к которому они присоединены, образуют замещенную или незамещенную гетероарильную группу, в которой указанные заместители такие, как определено выше;
с целью производства лекарственного средства для лечения воспалительных заболеваний.
12. Применение по п.11, где воспалительное заболевание выбрано из группы, включающей воспалительное заболевание кишечника (IBD), ревматоидный артрит (RA), доброкачественную гиперплазию простаты, болезнь Баррета, астму, восстановление скелетных мышц и сухожилий, язвенный колит, лейшманиоз и аутоиммунные заболевания, предпочтительно болезнь Крона.
13. Применение по п.11, где заболевание является раковым заболеванием.
14. Применение по п.11, где заболевание является раковым заболеванием, выбранным из группы, включающей метастаз, рак груди, рак пищевода, рак толстой кишки, карциному толстой кишки, рак желудка, лейкемию, меланому, карциному матки, немелкоклеточный рак легких, мелкоклеточный рак легких, рак яичника, карциномы яичников, рак простаты, почечный рак, рак печени, карциному поджелудочной железы, рак почек, рак мочевого пузыря, рак простаты, тестикулярный рак, рак костей, рак кожи, саркому, саркомы Капоши, опухоли головного мозга, миосаркомы, нейробластомы, лимфомы и множественную миелому.
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