RU2013127155A - Новые замещенные бициклические ароматические соединения в качестве ингибиторов s-нитрозоглутатион-редуктазы - Google Patents

Новые замещенные бициклические ароматические соединения в качестве ингибиторов s-нитрозоглутатион-редуктазы Download PDF

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RU2013127155A
RU2013127155A RU2013127155/04A RU2013127155A RU2013127155A RU 2013127155 A RU2013127155 A RU 2013127155A RU 2013127155/04 A RU2013127155/04 A RU 2013127155/04A RU 2013127155 A RU2013127155 A RU 2013127155A RU 2013127155 A RU2013127155 A RU 2013127155A
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group
compound according
hydroxynaphthalen
compound
benzoic acid
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RU2013127155/04A
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Сичэн СУНЬ
Цзянь ЦЮ
Адам СТАУТ
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Н30 Фармасьютикалс, Инк.
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Publication of RU2013127155A publication Critical patent/RU2013127155A/ru

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Abstract

1. Соединение Формулы 1:Формула 1где Rвыбран из группы, состоящей из Н, F и Cl;Rи Rнезависимо выбраны из группы, состоящей из Н, F, Cl, Br, Me, ОСНи циано;Rвыбран из группы, состоящей из Н, F, Cl, Br, Me и ОСН;Х выбран из группы, состоящей из,,,,,,,,,,, и;А выбран из группы, состоящей из,,,,,,, и;Rвыбран из группы, состоящей из F, Cl, Br, СН, CF, ОСН, циано, N(СН)и морфолино;n выбран из группы, состоящей из 0, 1 и 2;Rвыбран из группы, состоящей из Н, F, Cl, Br, СН, CF, ОСН, циано, N(СН)и морфолино;при условии, что если Х является, а A является СООН, то по меньшей мере один из R, R, R, Rи Rне является водородом, или n должен быть >0, и R, будучи в мета-положении к нафталину, не может быть СН.2. Соединение по п.1, отличающееся тем, чтоХ выбран из группы, состоящей из,,, и.3. Соединение по п.1, отличающееся тем, что Х является.4. Соединение по п.3, отличающееся тем, что Rявляется водородом.5. Соединение по п.3, отличающееся тем, что Rявляется водородом.6. Соединение по п.1, отличающееся тем, что соединением является соединение Формулы 2Формула 27. Соединение по п.6, отличающееся тем, чтоRвыбран из группы, состоящей из Н и F;Rвыбран из группы, состоящей из Н, F, Cl, Br и циано;Rвыбран из группы, состоящей из Н, F и Cl;Rявляется Н; иRвыбран из группы, состоящей из Н, F, Cl и циано.8. Соединение по п.6, отличающееся тем, что Rвыбран из группы, состоящей из F и Cl.9. Соединение по п.6, отличающееся тем, что Rвыбран из группы, состоящей из F, Cl, Br, Me, ОСНи циано.10. Соединение по п.6, отличающееся тем, что Rвыбран из группы, состоящей из F, Cl, Br, Me, ОСНи циано.11. Соединение по п.6, отличающееся тем, что Rвыбран из группы, состоящей из F, Cl, Br, Me и ОСН;12. Соединение по п.6, отличающееся тем, что Rвыбран из группы, состоящей из F, Cl, Br, СН, CF, ОСН, циано, N(СН)и морфолин�

Claims (32)

1. Соединение Формулы 1:
Figure 00000001
Формула 1
где R1 выбран из группы, состоящей из Н, F и Cl;
R2a и R2b независимо выбраны из группы, состоящей из Н, F, Cl, Br, Me, ОСН3 и циано;
R2c выбран из группы, состоящей из Н, F, Cl, Br, Me и ОСН3;
Х выбран из группы, состоящей из
Figure 00000002
,
Figure 00000003
,
Figure 00000004
,
Figure 00000005
,
Figure 00000006
Figure 00000007
,
Figure 00000008
,
Figure 00000009
,
Figure 00000010
,
Figure 00000011
Figure 00000012
,
Figure 00000013
,
Figure 00000014
, и
Figure 00000015
;
А выбран из группы, состоящей из
Figure 00000016
,
Figure 00000017
,
Figure 00000018
,
Figure 00000019
,
Figure 00000020
,
Figure 00000021
,
Figure 00000022
, и
Figure 00000023
;
R3 выбран из группы, состоящей из F, Cl, Br, СН3, CF3, ОСН3, циано, N(СН3)2 и морфолино;
n выбран из группы, состоящей из 0, 1 и 2;
R4 выбран из группы, состоящей из Н, F, Cl, Br, СН3, CF3, ОСН3, циано, N(СН3)2 и морфолино;
при условии, что если Х является
Figure 00000002
, а A является СООН, то по меньшей мере один из R1, R2a, R2b, R2c и R4 не является водородом, или n должен быть >0, и R3, будучи в мета-положении к нафталину, не может быть СН3.
2. Соединение по п.1, отличающееся тем, что
Х выбран из группы, состоящей из
Figure 00000002
,
Figure 00000004
,
Figure 00000003
, и
Figure 00000005
.
3. Соединение по п.1, отличающееся тем, что Х является
Figure 00000002
.
4. Соединение по п.3, отличающееся тем, что R2c является водородом.
5. Соединение по п.3, отличающееся тем, что R2b является водородом.
6. Соединение по п.1, отличающееся тем, что соединением является соединение Формулы 2
Figure 00000024
Формула 2
7. Соединение по п.6, отличающееся тем, что
R1 выбран из группы, состоящей из Н и F;
R2a выбран из группы, состоящей из Н, F, Cl, Br и циано;
R2b выбран из группы, состоящей из Н, F и Cl;
R2c является Н; и
R4 выбран из группы, состоящей из Н, F, Cl и циано.
8. Соединение по п.6, отличающееся тем, что R1 выбран из группы, состоящей из F и Cl.
9. Соединение по п.6, отличающееся тем, что R2a выбран из группы, состоящей из F, Cl, Br, Me, ОСН3 и циано.
10. Соединение по п.6, отличающееся тем, что R2b выбран из группы, состоящей из F, Cl, Br, Me, ОСН3 и циано.
11. Соединение по п.6, отличающееся тем, что R2c выбран из группы, состоящей из F, Cl, Br, Me и ОСН3;
12. Соединение по п.6, отличающееся тем, что R4 выбран из группы, состоящей из F, Cl, Br, СН3, CF3, ОСН3, циано, N(СН3)2 и морфолино.
13. Соединение по п.1, отличающееся тем, что соединением является соединение Формулы 3
Figure 00000025
Формула 3
14. Соединение по п.13, отличающееся тем, что Х является
Figure 00000002
15. Соединение по п.14, отличающееся тем, что А является СООН.
16. Соединение по п.13, отличающееся тем, что соединением является соединение Формулы 4
Figure 00000026
Формула 4
17. Соединение по п.16, отличающееся тем, что R2c является Н.
18. Соединение по п.16, отличающееся тем, что R2b является Н.
19. Соединение по п.16, отличающееся тем, что
R1 выбран из группы, состоящей из Н и F;
R2b выбран из группы, состоящей из Н, F и Cl;
R2c является Н; и
R4 выбран из группы, состоящей из Н, F, Cl и циано.
20. Соединение по п.1, отличающееся тем, что соединением является соединение Формулы 5
Figure 00000027
Формула 5
21. Соединение по п.20, отличающееся тем, что Х является
Figure 00000002
.
22. Соединение по п.21, отличающееся тем, что А является СООН.
23. Соединение по п.20, отличающееся тем, что соединением является соединение Формулы 6
Figure 00000028
Формула 6
24. Соединение по п.23, отличающееся тем, что R2c является Н.
25. Соединение по п.23, отличающееся тем, что K2b является Н.
26. Соединение по п.23, отличающееся тем, что
R2a выбран из группы, состоящей из Н, F, Cl, Br и циано;
R2a выбран из группы, состоящей из Н, F и Cl;
R2c является H; и
R4 выбран из группы, состоящей из Н, F, Cl и циано.
27. Соединение по п.1, отличающееся тем, что соединение выбрано из группы, состоящей из
3-хлор-4-(6-гидроксинафталин-2-ил)бензойной кислоты;
3-фтор-4-(6-гидроксинафталин-2-ил)бензойной кислоты;
4-(6-гидроксинафталин-2-ил)-3-метоксибензойной кислоты;
3-(диметиламино)-4-(6-гидроксинафталин-2-ил)бензойной кислоты;
3-циано-4-(6-гидроксинафталин-2-ил)бензойной кислоты;
4-(6-гидроксинафталин-2-ил)-3-морфолинобензойной кислоты;
4-(1-бром-6-гидроксинафталин-2-ил)бензойной кислоты;
4-(6-гидрокси-1-метилнафталин-2-ил)бензойной кислоты;
4-(1-циано-6-гидроксинафталин-2-ил)бензойной кислоты;
4-(6-гидрокси-3-метоксинафталин-2-ил)бензойной кислоты;
4-(1-хлор-6-гидроксинафталин-2-ил)бензойной кислоты;
6-(4-(1Н-тетразол-5-ил)фенил)нафталин-2-ола;
5-(6-гидроксинафталин-2-ил)пиколиновой кислоты;
6-(6-гидроксинафталин-2-ил)никотиновой кислоты;
5-(6-гидроксинафталин-2-ил)пиразин-2-карбоновой кислоты;
2-(6-гидроксинафталин-2-ил)пиримидин-5-карбоновой кислоты;
6-(6-гидроксинафталин-2-ил)пиридазин-3-карбоновой кислоты;
5-(6-гидроксинафталин-2-ил)пиримидин-2-карбоновой кислоты;
6-(1H-бензо[d][1,2,3]триазол-6-ил)нафталин-2-ола;
4-(6-гидроксинафталин-2-ил)-3-(трифторметил)бензойной кислоты;
3-хлор-4-(3-фтор-6-гидроксинафталин-2-ил)бензойной кислоты;
4-(3-хлор-6-гидроксинафталин-2-ил)бензойной кислоты;
4-(3-фтор-6-гидроксинафталин-2-ил)бензойной кислоты;
4-(6-гидрокси-1-метоксинафталин-2-ил)бензойной кислоты;
4-(1-фтор-6-гидроксинафталин-2-ил)бензойной кислоты;
4-(6-гидрокси-3-метилнафталин-2-ил)бензойной кислоты;
4-(1-циано-5-фтор-6-гидроксинафталин-2-ил)бензойной кислоты;
4-(1-циано-6-гидроксинафталин-2-ил)-3-фторбензойной кислоты;
3-хлор-4-(5-фтор-6-гидроксинафталин-2-ил)бензойной кислоты;
4-(5-фтор-6-гидроксинафталин-2-ил)бензойной кислоты;
3-фтор-4-(5-фтор-6-гидроксинафталин-2-ил)бензойной кислоты; и
4-(5-фтор-6-гидроксинафталин-2-ил)-3-метилбензойной кислоты.
28. Применение соединения Формулы 1 по п.1 или его фармацевтически приемлемой соли в качестве ингибитора GSNOR.
29. Применение соединения по п.27 или его фармацевтически приемлемой соли в качестве ингибитора GSNOR.
30. Фармацевтическая композиция, включающая терапевтически эффективное количество соединения по п.1 вместе с фармацевтически приемлемым носителем или формообразующим средством.
31. Способ лечения заболевания или состояния, который включает введение терапевтически эффективного количества соединения Формулы 1 по п.1 пациенту, нуждающемуся в этом.
32. Способ получения соединения Формулы 1 по п.1.
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