RU2006134026A - Производные гетероарилалкилкарбаматов, их получение и их применение в качестве ингибиторов фермента faah - Google Patents

Производные гетероарилалкилкарбаматов, их получение и их применение в качестве ингибиторов фермента faah Download PDF

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RU2006134026A
RU2006134026A RU2006134026/04A RU2006134026A RU2006134026A RU 2006134026 A RU2006134026 A RU 2006134026A RU 2006134026/04 A RU2006134026/04 A RU 2006134026/04A RU 2006134026 A RU2006134026 A RU 2006134026A RU 2006134026 A RU2006134026 A RU 2006134026A
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Russia
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ethyl
oxazolidinedione
group
formula
pyridinyl
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RU2006134026/04A
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RU2364586C2 (ru
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Ахмед АБУАБДЕЛЛА (FR)
Ахмед Абуабделла
Режин БАРЧ-ЛИ (FR)
Режин БАРЧ-ЛИ
Кристиан ХОРНАРТ (FR)
Кристиан Хорнарт
Антуан РАВЕ (FR)
Антуан Раве
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Санофи-Авентис (Fr)
Санофи-Авентис
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Abstract

1. Соединение, отвечающее общей формуле (I)в которойА выбран из одной или нескольких групп X, Y и/или Z;X означает метиленовую группу, необязательно замещенную одной или двумя группами, представляющими C-алкил, C-циклоалкил или C-циклоалкил-C-алкилен;Y означает или C-алкениленовую группу, необязательно замещенную одной или двумя группами, представляющими C-алкил, C-циклоалкил или C-циклоалкил-C-алкилен; или C-алкиниленовую группу;Z означает группу формулы:m означает целое число от 1 до 5;p и q означают целые числа и определены так, что p+q является числом от 1 до 5;n означает целое число от 1 до 7;Rозначает группу R, необязательно замещенную одной или несколькими группами Rи/или R;Rозначает группу, выбранную из пиридинила, пиримидинила, пиридазинила, пиразинила, триазинила, пирролила, фуранила, тиенила, имидазолила, оксазолила, тиазолила, пиразолила, изоксазолила, изотиазолила, оксадиазолила, тиадиазолила, триазолила, тетразолила, нафтила, хинолинила, тетрагидрохинолинила, изохинолинила, тетрагидроизохинолинила, 2-оксо-3,4-дигидрохинолинила, 1-оксо-3,4-дигидроизохинолинила, хиназолинила, хиноксалинила, фталазинила, циннолинила, нафтиридинила, бензофуранила, дигидробензофуранила, бензотиенила, дигидробензотиенила, индолила, индолинила, индазолила, изоиндолила, бензимидазолила, бензоксазолила, бензизоксазолила, бензотиазолила, бензизотиазолила, бензотриазолила, бензоксадиазолила, бензотиадиазолила, пирролопиридинила, фуропиридинила, тиенопиридинила, имидазопиридинила, оксазолопиридинила, тиазолопиридинила, пиразолопиридинила, изоксазолопиридинила, изотиазолопиридинила;Rозначает группу, выбранную из атомов галогена, групп циа�

Claims (12)

1. Соединение, отвечающее общей формуле (I)
Figure 00000001
в которой
А выбран из одной или нескольких групп X, Y и/или Z;
X означает метиленовую группу, необязательно замещенную одной или двумя группами, представляющими C1-6-алкил, C3-7-циклоалкил или C3-7-циклоалкил-C1-3-алкилен;
Y означает или C2-алкениленовую группу, необязательно замещенную одной или двумя группами, представляющими C1-6-алкил, C3-7-циклоалкил или C3-7-циклоалкил-C1-3-алкилен; или C2-алкиниленовую группу;
Z означает группу формулы:
Figure 00000002
m означает целое число от 1 до 5;
p и q означают целые числа и определены так, что p+q является числом от 1 до 5;
n означает целое число от 1 до 7;
R1 означает группу R2, необязательно замещенную одной или несколькими группами R3 и/или R4;
R2 означает группу, выбранную из пиридинила, пиримидинила, пиридазинила, пиразинила, триазинила, пирролила, фуранила, тиенила, имидазолила, оксазолила, тиазолила, пиразолила, изоксазолила, изотиазолила, оксадиазолила, тиадиазолила, триазолила, тетразолила, нафтила, хинолинила, тетрагидрохинолинила, изохинолинила, тетрагидроизохинолинила, 2-оксо-3,4-дигидрохинолинила, 1-оксо-3,4-дигидроизохинолинила, хиназолинила, хиноксалинила, фталазинила, циннолинила, нафтиридинила, бензофуранила, дигидробензофуранила, бензотиенила, дигидробензотиенила, индолила, индолинила, индазолила, изоиндолила, бензимидазолила, бензоксазолила, бензизоксазолила, бензотиазолила, бензизотиазолила, бензотриазолила, бензоксадиазолила, бензотиадиазолила, пирролопиридинила, фуропиридинила, тиенопиридинила, имидазопиридинила, оксазолопиридинила, тиазолопиридинила, пиразолопиридинила, изоксазолопиридинила, изотиазолопиридинила;
R3 означает группу, выбранную из атомов галогена, групп циано, нитро, C1-6-алкил, C3-7-циклоалкил, C1-6-алкокси, гидроксил, C1-6-тиоалкил, C1-6-фторалкил, C1-6-фторалкокси, C1-6-фтортиоалкил, NR5R6, NR5COR6, NR5CO2R6, NR5SO2R6, COR5, CO2R5, CONR5R6, SO2R5, SO2R5R6, -О-(C1-3-алкилен)-O и фенил, причем фенильная группа необязательно замещена одним или несколькими атомами галогена;
R4 означает группу, выбранную из групп: фенил, фенилокси, бензилокси, нафтил, пиридинил, пиримидинил, пиридазинил, пиразинил; причем группа или группы R4 могут быть замещены одной или несколькими группами R3, одинаковыми или отличающимися друг от друга;
R5 и R6 независимо друг от друга означают атом водорода или C1-6-алкильную группу, или вместе с атомом или атомами, с которыми они связаны, образуют цикл, выбранный из азетидинового, пирролидинового, пиперидинового, морфолинового, тиоморфолинового, азепинового или пиперазинового цикла, причем этот цикл необязательно замещен C1-6-алкильной или бензильной группой;
R7 означает атом водорода или C1-6-алкильную группу;
R8 означает атом водорода или группу C1-6-алкил, C3-7-циклоалкил, C3-7-циклоалкил-C1-3-алкилен;
в виде основания, кислотно-аддитивной соли, гидрата или сольвата.
2. Соединение формулы (I) по п. 1, отличающееся тем, что
А выбран из одной или нескольких групп X и/или Y;
X означает метиленовую группу;
Y означает C2-алкиниленовую группу;
n означает целое число от 1 до 5;
R1 означает группу R2, необязательно замещенную одной или несколькими группами R3 и/или R4;
R2 означает группу, выбранную из пиридинила, пиримидинила, пиридазинила, имидазолила, оксазолила, пиразолила, изоксазолила, оксадиазолила, нафтила, хинолинила, изохинолинила, дигидроизохинолинила, 2-оксо-3,4-дигидрохинолинила, индолила, бензимидазолила, пирролопиридинила;
R3 означает группу, выбранную из атомов галогена, групп C1-6-алкил, C3-7-циклоалкил, C1-6-алкокси, NR5R6 и фенил;
R4 означает группу, выбранную из групп: фенил, нафтил, пиридинил; причем группа или группы R4 могут быть замещены одной или несколькими группами R3, одинаковыми или отличающимися друг от друга;
R5 и R6 независимо друг от друга означают C1-6-алкильную группу;
R7 означает атом водорода или C1-6-алкильную группу;
R8 означает атом водорода или группу C1-6-алкил, C3-7-циклоалкил, C3-7-циклоалкил-C1-3-алкилен;
в виде основания, кислотно-аддитивной соли, гидрата или сольвата.
3. Соединение формулы (I) по п. 1 или 2, отличающееся тем, что R2 означает группу, выбранную из пиридинила, пиримидинила, оксазолила, изоксазолила, нафтила, хинолинила, изохинолинила.
4. Соединение формулы (I) по п. 1 или 2, отличающееся тем, что R7 означает атом водорода; R8 означает атом водорода или C1-6-алкильную группу,
в виде основания, кислотно-аддитивной соли, гидрата или сольвата.
5. Способ получения соединения формулы (I) по любому из пп. 1-4, включающий стадию, состоящую в преобразовании эфира-карбамата общей формулы (IV)
Figure 00000003
в которой A, n, R1 и R7 такие, как определено в формуле (I) по п. 1, и R означает метильную или этильную группу,
путем аминолиза амином общей формулы R8NH2, в которой R8 таково, как определено в формуле (I) по п. 1.
6. Способ получения соединения формулы (I) по любому из пп. 1-4, включающий стадию,
Figure 00000004
состоящую в преобразовании производного оксазолидиндиона общей формулы (VII),
в которой A, n, R1 и R7 такие, как определено в формуле (I) по п. 1,
путем аминолиза амином общей формулы R8NH2, в которой R8 таково, как определено в формуле (I) по п. 1.
7. Соединение, отвечающее общей формуле (IV),
Figure 00000003
в которой A, n, R1 и R7 такие, как определено в формуле (I) по п. 1, и R означает метильную или этильную группу, за исключением следующих соединений:
этил-2-[({[2-(5-гидрокси-1H-индол-3-ил)этил]амино}карбонил)окси]пропаноат;
этил-2-[({[2-[5-(фенилметокси)-1H-индол-3-ил]этил}амино)карбонил]окси]пропаноат.
8. Соединение, отвечающее общей формуле (VII),
Figure 00000004
в которой A, n, R1 и R7 такие, как определено в формуле (I) по п. 1, за исключением следующих соединений:
йодид 2-[2-(2,4-диоксо-3-оксазолидинил)этил]-1-метилпиридиния;
йодид 2-[2-(2,4-диоксо-3-оксазолидинил)этил]-5-этил-1-метилпиридиния;
йодид 4-[2-(2,4-диоксо-3-оксазолидинил)этил]-1-метилпиридиния;
гидрохлорид 5-метил-3-[2-(4-пиридинил)этил]-2,4-оксазолидиндиона;
гидрохлорид 5-метил-3-[2-(2-пиридинил)этил]-2,4-оксазолидиндиона;
3-(5-имидазо[1,2-a]пиридин-5-илпентил)-2,4-оксазолидиндион;
3-[2-(5-метил-4-тиазолил)этил]-2,4-оксазолидиндион;
3-[2-(1H-пиррол-2-ил)этил]-2,4-оксазолидиндион;
3-[2-(2-тиенил)этил]-2,4-оксазолидиндион;
3-[3-(2-тиенил)пропил]-2,4-оксазолидиндион;
3-[4-(2-тиенил)бутил]-2,4-оксазолидиндион;
5-метил-3-[2-(2-тиенил)этил]-2,4-оксазолидиндион;
5-этил-3-[2-(2-тиенил)этил]-2,4-оксазолидиндион;
3-[2-(3-тиенил)этил]-2,4-оксазолидиндион;
3-[2-(5-метил-2-тиенил)этил]-2,4-оксазолидиндион;
3-[2-(5-ацетил-2-тиенил)этил]-2,4-оксазолидиндион;
3-[2-(5-бром-2-тиенил)этил]-2,4-оксазолидиндион;
5-[2-(2,4-диоксо-3-оксазолидинил)этил]-2-тиофенкарбоксальдегид;
3-[3-[1-индолинил)пропил]-2,4-оксазолидиндион;
3-[3-[1-индолинил)пропил]-5-метил-2,4-оксазолидиндион;
3-[2-(2-пиридинил)этил]-2,4-оксазолидиндион;
3-[2-(5-этил-2-пиридинил)этил]-5-метил-2,4-оксазолидиндион;
5-этил-3-[2-(5-этил-2-пиридинил)этил]-2,4-оксазолидиндион;
3-[2-(5-этил-2-пиридинил)этил]-5-изопропил-2,4-оксазолидиндион;
3-[2-(4-пиридинил)этил]-2,4-оксазолидиндион;
5-этил-3-[2-(4-пиридинил)этил]-2,4-оксазолидиндион;
5-этил-3-[2-(2-пиридинил)этил]-2,4-оксазолидиндион;
5-изопропил-3-[2-(4-пиридинил)этил]-2,4-оксазолидиндион;
5-изопропил-3-[2-(2-пиридинил)этил]-2,4-оксазолидиндион;
3-[2-(5-этил-2-пиридинил)этил]-2,4-оксазолидиндион.
9. Фармацевтическая композиция, содержащая по меньшей мере одно соединение формулы (I) по любому из пп. 1-4 в виде фармацевтически приемлемого основания, соли, гидрата или сольвата и необязательно один или несколько фармацевтически приемлемых эксципиентов.
10. Применение соединения формулы (I) по любому из пп. 1-4 в виде фармацевтически приемлемого основания, соли, гидрата или сольвата в качестве лекарственного средства.
11. Применение соединения формулы (I) по любому из пп. 1-4 в виде фармацевтически приемлемого основания, соли, гидрата или сольвата для получения лекарственного средства, предназначенного для предупреждения или лечения патологии, в которую вовлечены эндогенные каннабиоиды и/или любые другие субстраты, метаболизированные ферментом FAAH.
12. Применение соединения формулы (I) по любому из пп. 1-4 в виде фармацевтически приемлемого основания, соли, гидрата или сольвата, для получения лекарственного средства, предназначенного для предупреждения или лечения острых или хронических болей, головокружений, рвоты, тошноты, нарушений пищевого поведения, неврологических и психиатрических патологий, острых или хронических нейродегенеративных заболеваний, эпилепсии, нарушений сна, сердечно-сосудистых заболеваний, почечной ишемии, рака, расстройств иммунной системы, аллергических заболеваний, инфекционных паразитарных, вирусных или бактериальных заболеваний, воспалительных заболеваний, остеопороза, глазных болезней, болезней легких, желудочно-кишечных заболеваний или недержания мочи.
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EP1720829A1 (fr) 2006-11-15
RS51246B (sr) 2010-12-31
CN1926097B (zh) 2011-06-08
EP2251324A1 (fr) 2010-11-17
CA2554609A1 (fr) 2005-09-29
KR20070011297A (ko) 2007-01-24
ES2334449T3 (es) 2010-03-10
IL177329A0 (en) 2006-12-10
PT1720829E (pt) 2010-01-13
BRPI0508193A (pt) 2007-08-14
MA28367A1 (fr) 2006-12-01
HRP20100017T1 (hr) 2010-02-28
NO20064329L (no) 2006-09-25
PL1720829T3 (pl) 2010-03-31
HK1101759A1 (en) 2007-10-26
AU2005223423A1 (en) 2005-09-29
US20070021426A1 (en) 2007-01-25
DE602005017122D1 (de) 2009-11-26
AU2005223423B2 (en) 2011-04-14
US20100069405A1 (en) 2010-03-18
RU2364586C2 (ru) 2009-08-20
FR2866886A1 (fr) 2005-09-02
IL177329A (en) 2012-01-31
CY1109716T1 (el) 2014-08-13
TW200533637A (en) 2005-10-16
US7645757B2 (en) 2010-01-12
AR047973A1 (es) 2006-03-15
ATE445592T1 (de) 2009-10-15
WO2005090292A1 (fr) 2005-09-29
DK1720829T3 (da) 2010-03-01
CN1926097A (zh) 2007-03-07
ZA200606724B (en) 2007-12-27
NZ550008A (en) 2010-06-25
SI1720829T1 (sl) 2010-02-26
EP1720829B1 (fr) 2009-10-14
JP4824668B2 (ja) 2011-11-30
JP2007524705A (ja) 2007-08-30
US20110237595A1 (en) 2011-09-29
FR2866886B1 (fr) 2007-08-31

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