RU2011152891A - Diarylhydantoins - Google Patents

Diarylhydantoins Download PDF

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RU2011152891A
RU2011152891A RU2011152891/04A RU2011152891A RU2011152891A RU 2011152891 A RU2011152891 A RU 2011152891A RU 2011152891/04 A RU2011152891/04 A RU 2011152891/04A RU 2011152891 A RU2011152891 A RU 2011152891A RU 2011152891 A RU2011152891 A RU 2011152891A
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pharmaceutically acceptable
acceptable salt
group
compound
compound according
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RU2638833C2 (en
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Чарлз Л. СОЙЕРС
Майкл Э. ЮНГ
Чарли Д. ЧЭН
Самеди Оук
Дерек УЭЛСБИ
Крис ТРАН
Джон ВОНГВАЙПАТ
Донгвон УО
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Те Риджентс Оф Те Юниверсити Оф Калифорния
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1. Соединение со следующей формулой1. The compound with the following formula
Figure 00000001
Figure 00000001
 или его фармацевтически приемлемая соль,or a pharmaceutically acceptable salt thereof, в которой Х выбран из группы, состоящей из трифторметила и йода,in which X is selected from the group consisting of trifluoromethyl and iodine, W выбран из группы, состоящей из О т NR5,W is selected from the group consisting of O t NR5, в которой R5 выбран из группы, состоящей из Н, метила, иin which R5 is selected from the group consisting of H, methyl, and
Figure 00000002
Figure 00000002
 где D является S или О и Е является NH или О и G является алкилом, арилом, замещенным алкилом или замещенным арилом; или D является S или О и E-G совместно являются С1-С4 алкилами,where D is S or O and E is NH or O and G is alkyl, aryl, substituted alkyl or substituted aryl; or D is S or O and E-G together are C1-C4 alkyl, R1 и R2 совместно включают восемь или менее атомов углерода и выбраны из группы, состоящей из алкила, замещенного алкила, включая галоалкил, и вместе с углеродом, к которому они присоединены, циклоалкила или замещенной циклоалкильной группы,R1 and R2 together include eight or less carbon atoms and are selected from the group consisting of alkyl, substituted alkyl, including haloalkyl, and together with the carbon to which they are attached, cycloalkyl or substituted cycloalkyl group, R3 выбран из группы, состоящей из водорода, галогена, метила, С1-С4 алкокси, формила, галоацетокси, трифторметил, циано, нитро, гидроксила, фенила, амино, метилкарбамоила, метоксикарбонила, ацетамидо, метансульфорамидо, метансульфонила, 4-метансульфонил-1-пиперазинила, пипаразинила и С1-С6 алкила или алкенила необязательно замещенных гидроксилом, метоксикарбонилом, амино, амидо или нитро,R3 is selected from the group consisting of hydrogen, halogen, methyl, C1-C4 alkoxy, formyl, haloacetoxy, trifluoromethyl, cyano, nitro, hydroxyl, phenyl, amino, methylcarbamoyl, methoxycarbonyl, acetamido, methanesulfonamido, methanesulfonyl, 4-methanesulfonyl-1 piperazinyl, piparasinyl and C1-C6 alkyl or alkenyl optionally substituted with hydroxyl, methoxycarbonyl, amino, amido or nitro, R4 выбран из группы, состоящей из водорода, галогена, алкила и галоалкила,R4 is selected from the group consisting of hydrogen, halogen, alkyl and haloalkyl, R3 не является метиламинометилом или диметиламинометилом.R3 is not methylaminomethyl or dimethylaminomethyl. 2. Соединение по п.1, где R5 является2. The compound according to claim 1, where R5 is
Figure 00000003
,
Figure 00000004
,
Figure 00000005
или
Figure 00000006
.
Figure 00000003
,
Figure 00000004
,
Figure 00000005
or
Figure 00000006
. или его фармацевтически приемлемая соль.or a pharmaceutically acceptable salt thereof. 3. Соединение по п.1, формулы3. The compound according to claim 1, the formula
Figure 00000007
Figure 00000007
 в которой R3 выбран из группы, состоящей из гидроксила, метилкарбамоила, метилкарбамоилпропила, метилкарбамоилэтила, метилкарбамоилметила, метилсульфонкарбамоилпропила, метиламинометила, диметиламинометила, метилсульфонилоксиметила, карбамоилметила, карбамоилэтила, метоксикарбонилметила, метансульфонила, 4-метансульфонил-1-пиперазинила, пиперазинила и метоксикарбонила, иin which R3 is selected from the group consisting of hydroxyl, methylcarbamoyl, methylcarbamoylpropyl, methylcarbamoylethyl, methylcarbamoylmethyl, methylsulfonocarbamoylpropyl, methylaminomethylmethylmethyl-1-methanesulfonylmethyl-methyl-1-methanesulfonylmethyloxymethyl-methonomethyl-methonomethyl-methonomethyl-methonomethyl-methonomethyl-4-methylcarbonylmethyl-methyl-methanes-methyl-1-methyl-methanesulfonyl] R10 и R11 оба являются Н или соответственно, F и Н или Н и FR10 and R11 are both H or F, respectively, and H or H and F или его фармацевтически приемлемая соль.or a pharmaceutically acceptable salt thereof. 4. Соединение по п.3, где R10 и R11 оба являются Н или его фармацевтически приемлемая соль.4. The compound according to claim 3, where R10 and R11 are both H or a pharmaceutically acceptable salt thereof. 5. Соединение по п.3, где R10 и R11 являются соответственно F и Н или его фармацевтически приемлемая соль.5. The compound according to claim 3, where R10 and R11 are respectively F and H or a pharmaceutically acceptable salt thereof. 6. Соединение по п.3, где R3 является метилкарбамоилом или его фармацевтически приемлемая соль.6. The compound according to claim 3, where R3 is methylcarbamoyl or its pharmaceutically acceptable salt. 7. Соединение по п.3, где R3 является метилкарбамоилом и R10 и R11 являются соответственно F и H или его фармацевтически приемлемая соль.7. The compound according to claim 3, where R3 is methylcarbamoyl and R10 and R11 are respectively F and H or a pharmaceutically acceptable salt thereof. 8. Соединение по п.1, где R1 и R2 независимо являются метилом или вместе с углеродом, к которому они присоединены, циклоалкильной группой с 4-5 атомами углерода,8. The compound according to claim 1, where R1 and R2 are independently methyl or together with the carbon to which they are attached, cycloalkyl group with 4-5 carbon atoms, R3 является метилкарбамоилом и R4 является Н или F или его фармацевтически приемлемая соль.R3 is methylcarbamoyl and R4 is H or F or a pharmaceutically acceptable salt thereof. 9. Соединение по п.8, где R4 является 3-фтор или его фармацевтически приемлемая соль.9. The compound of claim 8, where R4 is 3-fluoro or a pharmaceutically acceptable salt thereof. 10. Соединение по п.1, где R1 и R2 независимо являются метилом или вместе с углеродом, к которому они присоединены, циклоалкильной группой с 4-5 атомами углерода,10. The compound according to claim 1, where R1 and R2 are independently methyl or together with the carbon to which they are attached, cycloalkyl group with 4-5 carbon atoms, R3 выбран из группы, состоящей из циано, гидроксила, метилкарбамоила, метоксикарбонила, ацетамидо, метансульфонамидо, 4-метансульфонил-1-пиперазинила и пиперазинила и R4 является F или его фармацевтически приемлемая соль.R3 is selected from the group consisting of cyano, hydroxyl, methylcarbamoyl, methoxycarbonyl, acetamido, methanesulfonamido, 4-methanesulfonyl-1-piperazinyl and piperazinyl and R4 is F or a pharmaceutically acceptable salt thereof. 11. Соединение по п.1 формулы11. The compound according to claim 1 of the formula
Figure 00000008
Figure 00000008
 в которой R3 выбран из группы, состоящей из метилкарбонила, ацетамидо и метансульфонамидо и R4 выбран из группы, состоящей из F и Н или его фармацевтически приемлемая соль.in which R3 is selected from the group consisting of methylcarbonyl, acetamido and methanesulfonamido, and R4 is selected from the group consisting of F and H or a pharmaceutically acceptable salt thereof. 12. Соединение по п.1 формулы12. The compound according to claim 1 of the formula
Figure 00000009
Figure 00000009
 в которой R4 выбран из группы, состоящей из F и Н или его фармацевтически приемлемая соль.in which R4 is selected from the group consisting of F and H or a pharmaceutically acceptable salt thereof. 13. Соединение по п.1, где R1 и R2 вместе с углеродом, к которому они присоединены, являются13. The compound according to claim 1, where R1 and R2 together with the carbon to which they are attached, are
Figure 00000010
,
Figure 00000011
или
Figure 00000012
или его фармацевтически приемлемая соль.
Figure 00000010
,
Figure 00000011
or
Figure 00000012
or a pharmaceutically acceptable salt thereof. 14. Фармацевтическая композиция для лечения гиперпролиферативных заболеваний, содержащая терапевтически эффективное количеств соединения по п.1, или фармацевтически приемлемой его соли и фармацевтически приемлемые носитель или разбавитель.14. A pharmaceutical composition for treating hyperproliferative diseases, comprising a therapeutically effective amount of a compound according to claim 1, or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier or diluent. 15. Фармацевтическая композиция для лечения гиперпролиферативных заболеваний, содержащая терапевтически эффективное количеств соединения по п.9, или фармацевтически приемлемой его соли и фармацевтически приемлемые носитель или разбавитель.15. A pharmaceutical composition for treating hyperproliferative diseases, comprising a therapeutically effective amount of a compound according to claim 9, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent. 16. Фармацевтическая композиция по п.14, в которой фармацевтически приемлемые носитель или разбавитель представляют собой один или более диметилсульфоксид (DMSO), полиэтиленгликоль (PEG) и воду.16. The pharmaceutical composition of claim 14, wherein the pharmaceutically acceptable carrier or diluent is one or more dimethyl sulfoxide (DMSO), polyethylene glycol (PEG), and water. 17. Соединение по п.1 или его фармацевтически приемлемая соль, где17. The compound according to claim 1 or its pharmaceutically acceptable salt, where R3 выбран из группы, состоящей из Н, F, Br, I, метила, С1-С4 алкокси, формила, галоацетокси, трифторметила, циано, нитро, гидроксила, фенила, метилкарбамоила, метоксикарбонила, ацетамидо, метансульфонамидо, метансульфонила, 4-метансульфонил-1-пиперазинила, пиперазинила и С1-С6 алкила или алкенила, необязательно замещенных гидроксилом, метаноксикарбонилом, амино, амидо и нитро или его фармацевтически приемлемая соль.R3 is selected from the group consisting of H, F, Br, I, methyl, C1-C4 alkoxy, formyl, haloacetoxy, trifluoromethyl, cyano, nitro, hydroxyl, phenyl, methylcarbamoyl, methoxycarbonyl, acetamido, methanesulfonamido, methanesulfonyl, 4-methanesulfonyl- 1-piperazinyl, piperazinyl and C1-C6 alkyl or alkenyl optionally substituted with hydroxyl, methoxycarbonyl, amino, amido and nitro, or a pharmaceutically acceptable salt thereof. 18. Соединение по п.1 или его фармацевтически приемлемая соль, где Х представляет собой трифторметил, W выбран из группы, состоящей из O и NR5, R5 выбран из группы, состоящей из Н, метила,18. The compound according to claim 1 or its pharmaceutically acceptable salt, where X is trifluoromethyl, W is selected from the group consisting of O and NR5, R5 is selected from the group consisting of H, methyl,
Figure 00000003
,
Figure 00000004
,
Figure 00000005
и
Figure 00000006
,
Figure 00000003
,
Figure 00000004
,
Figure 00000005
and
Figure 00000006
, R3 выбран из группы, состоящей из Н, F, Br, I, трифторметила, циано, гидроксила, фенила, метилкарбамоила, метоксикарбонила, меиансульфонила, этила, н-пропила, изо-пропила, н-бутила, втор-бутила, изо-бутила, трет-бутила, пентила, гексила, изогексила, 2-метилпентила, С1-С6 алкила, замещенного гидроксилом, метоксикарбамоилом и С1-С6 алкенила необязательно замещенного гидроксилом, иR3 is selected from the group consisting of H, F, Br, I, trifluoromethyl, cyano, hydroxyl, phenyl, methylcarbamoyl, methoxycarbonyl, meansulfonyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl , tert-butyl, pentyl, hexyl, isohexyl, 2-methylpentyl, C1-C6 alkyl substituted with hydroxyl, methoxycarbamoyl and C1-C6 alkenyl optionally substituted with hydroxyl, and где R4 выбран из группы, состоящей из Н и галогена.where R4 is selected from the group consisting of H and halogen. 19. Соединение по п.1 или его фармацевтически приемлемая соль, где19. The compound according to claim 1 or its pharmaceutically acceptable salt, where Х представляет собой трифторметил,X represents trifluoromethyl, W является O,W is O, R1 и R2 вместе состоят из 8 или менее атомов углерода и выбраны из группы, состоящей из алкила и циалоалкила,R1 and R2 together consist of 8 or less carbon atoms and are selected from the group consisting of alkyl and cyaloalkyl, R3 представляет собой метилкарбамоил иR3 is methylcarbamoyl and R4 выбран из группы, состоящей из Н и F.R4 is selected from the group consisting of H and F. 20. Способ лечения гиперпролиферативного заболевания, включающий введение субъекту, нуждающемуся в этом терапевтически эффективного количества соединения по любому из пп.1-13 или 17-19 или его фармацевтически приемлемой соли, включая фармацевтически приемлемые соли следующих соединений20. A method of treating a hyperproliferative disease, comprising administering to a subject in need of a therapeutically effective amount of a compound according to any one of claims 1 to 13 or 17-19 or a pharmaceutically acceptable salt thereof, including pharmaceutically acceptable salts of the following compounds
Figure 00000013
или
Figure 00000014
или
Figure 00000013
or
Figure 00000014
or
Figure 00000015
Figure 00000015
 21. Способ по п.20, где гиперпролиферативное заболевание представляет собой рак простаты.21. The method according to claim 20, where the hyperproliferative disease is prostate cancer. 22. Способ по п.20, где гиперпролиферативным заболеванием является невосприимчивый к гормонам рак простаты.22. The method according to claim 20, where the hyperproliferative disease is hormone-resistant prostate cancer. 23. Способ по п.20, где гиперпролиферативное заболевание является чувствительным к гормоном раком простаты.23. The method according to claim 20, where the hyperproliferative disease is hormone-sensitive prostate cancer. 24. Способ по п.20, где гиперпролиферативным заболеванием является доброкачественная гиперплазия простаты.24. The method according to claim 20, where the hyperproliferative disease is benign prostatic hyperplasia. 25. Способ по п.20, где гиперпролиферативным заболеванием является рак груди.25. The method according to claim 20, where the hyperproliferative disease is breast cancer. 26. Способ по п.20, где гиперпролиферативным заболеванием является рак яичника.26. The method according to claim 20, where the hyperproliferative disease is ovarian cancer. 27. Фармацевтически приемлемая соль соединения формулы27. A pharmaceutically acceptable salt of a compound of formula
Figure 00000013
или
Figure 00000014
, или
Figure 00000013
or
Figure 00000014
, or
Figure 00000015
Figure 00000015
 28. Фармацевтически приемлемая соль по п.27, где соединение имеет формулу28. The pharmaceutically acceptable salt of claim 27, wherein the compound has the formula
Figure 00000016
.
Figure 00000016
. 29. Фармацевтически приемлемая соль по п.27, где соединение имеет формулу29. The pharmaceutically acceptable salt of claim 27, wherein the compound has the formula
Figure 00000017
.
Figure 00000017
. 30. Фармацевтически приемлемая соль по п.27, где соединение имеет формулу30. The pharmaceutically acceptable salt of claim 27, wherein the compound has the formula
Figure 00000018
.
Figure 00000018
. 31. Способ лечения гиперпролиферативного заболевания включающий введение субъекту, нуждающемуся в этом терапевтически эффективного количества соединения формулы31. A method of treating a hyperproliferative disease comprising administering to a subject in need of a therapeutically effective amount of a compound of the formula
Figure 00000019
или
Figure 00000019
or
Figure 00000020
, или
Figure 00000020
, or
Figure 00000021
,
Figure 00000021
, или его фармацевтически приемлемой соли,or a pharmaceutically acceptable salt thereof, где гиперпролиферативное заболевание выбрано из группы, состоящей из чувствительного к гормонам рака простаты, доброкачественной гиперплазии простаты, рака груди и рака яичника.where the hyperproliferative disease is selected from the group consisting of hormone-sensitive prostate cancer, benign prostatic hyperplasia, breast cancer and ovarian cancer. 32. Способ по п.31, где гиперпролиферативное заболевание представляет собой чувствительней к гормонам рак простаты.32. The method according to p, where the hyperproliferative disease is more susceptible to hormones prostate cancer. 33. Способ по п.31, где гиперпролиферативное заболевание представляет собой доброкачественную гиперплазию простаты.33. The method of claim 31, wherein the hyperproliferative disease is benign prostatic hyperplasia. 34. Способ по п.31, где гиперпролиферативное заболевание представляет собой рак груди.34. The method of claim 31, wherein the hyperproliferative disease is breast cancer. 35. Способ по п.31, где гиперпролиферативное заболевание представляет собой рак яичника.35. The method of claim 31, wherein the hyperproliferative disease is ovarian cancer. 36. Способ по любому из пп.31-35, где соединение имеет формулу36. The method according to any one of paragraphs.31-35, where the compound has the formula
Figure 00000016
.
Figure 00000016
. 37. Способ по любому из пп.31-35, где соединение имеет формулу37. The method according to any one of paragraphs.31-35, where the compound has the formula
Figure 00000017
.
Figure 00000017
. 38. Способ по любому из пп.31-35, где соединение имеет формулу38. The method according to any one of paragraphs.31-35, where the compound has the formula
Figure 00000018
.
Figure 00000018
.
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