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RU2002100037A - Using derivatives of (-) (3-trihalomethylphenoxy) - (4-halophenyl) acetic acid for the treatment of insulin resistance, type II diabetes, hyperlipidemia and hyperuricemia - Google Patents

Using derivatives of (-) (3-trihalomethylphenoxy) - (4-halophenyl) acetic acid for the treatment of insulin resistance, type II diabetes, hyperlipidemia and hyperuricemia

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RU2002100037A
RU2002100037A RU2002100037/14A RU2002100037A RU2002100037A RU 2002100037 A RU2002100037 A RU 2002100037A RU 2002100037/14 A RU2002100037/14 A RU 2002100037/14A RU 2002100037 A RU2002100037 A RU 2002100037A RU 2002100037 A RU2002100037 A RU 2002100037A
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compound
lower alkoxy
alkylamino
alkoxy
substituted
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RU2002100037/14A
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Russian (ru)
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RU2281762C2 (en
Inventor
Кеннет Л. ЛАСКИ
Джайн ЛУО
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Метаболекс, Инк.
Диатекс, Инк.
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Priority claimed from US09/325,997 external-priority patent/US6262118B1/en
Application filed by Метаболекс, Инк., Диатекс, Инк. filed Critical Метаболекс, Инк.
Publication of RU2002100037A publication Critical patent/RU2002100037A/en
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Claims (53)

1. Способ модулирования диабета II типа у млекопитающего, включающий введение указанному млекопитающему терапевтически эффективного количества (-)стереоизомера соединения формулы I1. A method for modulating type II diabetes in a mammal, comprising administering to said mammal a therapeutically effective amount of a (-) stereoisomer of a compound of formula I
Figure 00000001
Figure 00000001
 где R - выбран из группы, состоящей из гидрокси, низшего аралкокси, ди-низшего алкиламино-низшего алкокси, низшего алканамидо низшего алкокси, бензамидо-низшего алкокси, уреидо-низшего алкокси, N'-низшего алкил–уреидо-низшего алкокси, карбамоил-низшего алкокси, галофеноксизамещенного низшего алкокси, карбамоилзамещенного фенокси, карбонил-низшего алкиламино, N,N-ди-низшего алкиламино-низшего алкиламино, галогензамещенного низшего алкиламино, гидроксизамещенного низшего алкиламино, низшего алканолилоскизамещенного низшего алкиламино, уреидо и низшего алкоксикарбониламино; иwhere R is selected from the group consisting of hydroxy, lower aralkoxy, lower lower alkylamino lower alkoxy, lower alkanamido lower alkoxy, benzamide lower alkoxy, ureido lower alkoxy, N'-lower alkyl-ureido lower alkoxy, carbamoyl- lower alkoxy, halophenoxy substituted lower alkoxy, carbamoyl substituted phenoxy, carbonyl lower alkylamino, N, N-di-lower alkylamino lower alkylamino, halogen substituted lower alkylamino, hydroxy substituted lower alkylamino, lower alkanolylamino substituted lower alkyl reido and lower alkoxycarbonylamino; and Х представляет собой галоген; или его фармацевтически приемлемой соли, причем это соединение по существу не содержит своего (+)стереоизомера.X is halogen; or a pharmaceutically acceptable salt thereof, wherein the compound is substantially free of its (+) stereoisomer. 2. Способ по п.1, в котором соединение представляет собой соединение формулы II2. The method according to claim 1, in which the compound is a compound of formula II
Figure 00000002
Figure 00000002
 где R2 - выбран из группы, состоящей из фенил-низшего алкила, низшего алканамидо-низшего алкила и бензамидо-низшего алкила.where R 2 is selected from the group consisting of phenyl lower alkyl, lower alkanamido lower alkyl, and benzamido lower alkyl. 3. Способ по п.1, в котором соединение представляет собой (-)2-ацетамидоэтил-4-хлорфенил-(3-трифторметилфенокси)ацетат.3. The method according to claim 1, wherein the compound is (-) 2-acetamidoethyl-4-chlorophenyl- (3-trifluoromethylphenoxy) acetate. 4. Способ по п.1, в котором соединение вводят путем внутривенного вливания, чрескожно или перорально.4. The method according to claim 1, in which the compound is administered by intravenous infusion, transdermally or orally. 5. Способ по п.1, в котором вводимое количество соединения составляет от около 100 до около 3000 мг в день.5. The method according to claim 1, in which the administered amount of the compound is from about 100 to about 3000 mg per day. 6. Способ по п.1, в котором вводимое количество соединения составляет от около 500 до около 1500 мг в день.6. The method according to claim 1, in which the administered amount of the compound is from about 500 to about 1500 mg per day. 7. Способ по п.1, в котором вводимое количество соединения оставляет от около 5 до около 250 мг в день.7. The method according to claim 1, in which the administered amount of the compound leaves from about 5 to about 250 mg per day. 8. Способ по п.1, в котором соединение вводят вместе с фармацевтически приемлемым носителем.8. The method according to claim 1, in which the compound is administered together with a pharmaceutically acceptable carrier. 9. Способ по п.1, в котором соединение модулирует гипергликемию путем понижения уровней содержания в крови глюкозы у млекопитающего.9. The method according to claim 1, in which the compound modulates hyperglycemia by lowering blood glucose levels in a mammal. 10. Способ по п.1, в котором соединение модулирует гемоглобин A1c у млекопитающего.10. The method according to claim 1, in which the compound modulates hemoglobin A 1c in a mammal. 11. Способ по п.1, в котором соединение модулирует микрососудистое и макрососудистое осложнения, связанные с диабетом.11. The method according to claim 1, in which the compound modulates microvascular and macrovascular complications associated with diabetes. 12. Способ по п.11, в котором микрососудистое осложнение представляет собой ретинопатию, невропатию или нефропатию.12. The method according to claim 11, in which the microvascular complication is retinopathy, neuropathy or nephropathy. 13. Способ по п.11, в котором макрососудистое осложнение представляет собой сердечно-сосудистое заболевание или заболевание периферических сосудов.13. The method according to claim 11, in which the macrovascular complication is a cardiovascular disease or a disease of peripheral vessels. 14. Способ по п.1, в котором соединение модулирует атеросклероз.14. The method of claim 1, wherein the compound modulates atherosclerosis. 15. Способ по п.1, в котором соединение предотвращает развитие диабета у млекопитающего.15. The method according to claim 1, in which the compound prevents the development of diabetes in a mammal. 16. Способ по п.1, в котором соединение вводят в сочетании с соединением, выбранным из группы, состоящей из: сульфонилмочевины или другого секретера инсулина, тиазолидиндиона, фибрата, ингибитора HMG-CoA-редуктазы, бигуанида, смолы, связывающей желчную кислоту, никотиновой кислоты, ингибитора α-глюкозидазы и инсулина.16. The method according to claim 1, in which the compound is administered in combination with a compound selected from the group consisting of: sulfonylurea or another insulin secretion, thiazolidinedione, fibrate, HMG-CoA reductase inhibitor, biguanide, bile acid binding resin, nicotinic acid, α-glucosidase inhibitor and insulin. 17. Способ модулирования резистентности к инсулину у млекопитающего, включающий введение указанному млекопитающему терапевтически эффективного количества (-)стереоизомера соединения формулы I17. A method for modulating insulin resistance in a mammal, comprising administering to said mammal a therapeutically effective amount of a (-) stereoisomer of a compound of formula I
Figure 00000003
Figure 00000003
 где R - выбран из группы, состоящей из гидрокси, низшего аралкокси, ди-низшего алкиламино-низшего алкокси, низшего алканамидо низшего алкокси, бензамидо-низшего алкокси, уреидо-низшего алкокси, N'-низшего алкил-уреидо-низшего алкокси, карбамоил-низшего алкокси, галофеноксизамещенного низшего алкокси, карбамоилзамещенного фенокси, карбонил-низшего алкиламино, N,N-ди-низшего алкиламино-низшего алкиламино, галогензамещенного низшего алкиламино, гидроксизамещенного низшего алкиламино, низшего алканолилоскизамещенного низшего алкиламино, уреидо и низшего алкоксикарбониламино; иwhere R is selected from the group consisting of hydroxy, lower aralkoxy, di-lower alkylamino-lower alkoxy, lower alkanamido-lower alkoxy, benzamido-lower alkoxy, ureido-lower alkoxy, N'-lower alkyl-ureido-lower alkoxy, carbamoyl- lower alkoxy, halophenoxy substituted lower alkoxy, carbamoyl substituted phenoxy, carbonyl lower alkylamino, N, N-di-lower alkylamino lower alkylamino, halogen substituted lower alkylamino, hydroxy substituted lower alkylamino, lower alkanolylamino substituted lower alkyl eido and lower alkoxycarbonylamino; and Х представляет собой галоген; или его фармацевтически приемлемой соли, причем это соединение по существу не содержит своего (+)стереоизомера.X is halogen; or a pharmaceutically acceptable salt thereof, wherein the compound is substantially free of its (+) stereoisomer. 18. Способ по п.17, в котором соединение представляет собой соединение формулы II18. The method according to 17, in which the compound is a compound of formula II
Figure 00000004
Figure 00000004
 где R2 - выбран из группы, состоящей из фенил-низшего алкила, низшего алканамидо-низшего алкила и бензамидо-низшего алкила.where R 2 is selected from the group consisting of phenyl lower alkyl, lower alkanamido lower alkyl, and benzamido lower alkyl. 19. Способ по п.17, в котором соединение представляет собой (-)2-ацетамидоэтил-4-хлорфенил-(3-трифторметилфенокси)ацетат.19. The method of claim 17, wherein the compound is (-) 2-acetamidoethyl-4-chlorophenyl- (3-trifluoromethylphenoxy) acetate. 20. Способ по п.17, в котором соединение вводят путем внутривенного вливания, чрескожно или перорально.20. The method according to 17, in which the compound is administered by intravenous infusion, transdermally or orally. 21. Способ по п.17, в котором вводимое количество соединения составляет от около 100 до около 3000 мг в день.21. The method according to 17, in which the administered amount of the compound is from about 100 to about 3000 mg per day. 22. Способ по п.17, в котором вводимое количество соединения составляет от около 500 до около 1500 мг в день.22. The method according to 17, in which the administered amount of the compound is from about 500 to about 1500 mg per day. 23. Способ по п.17, в котором вводимое количество соединения составляет от около 5 до около 250 мг в день.23. The method according to 17, in which the administered amount of the compound is from about 5 to about 250 mg per day. 24. Способ по п.17, в котором соединение вводят вместе с фармацевтически приемлемым носителем.24. The method according to 17, in which the compound is administered together with a pharmaceutically acceptable carrier. 25. Способ по п.17, в котором соединение предотвращает развитие резистентности к инсулину у млекопитающего.25. The method according to 17, in which the compound prevents the development of insulin resistance in a mammal. 26. Способ по п.17, в котором соединение модулирует синдром поликистоза яичников.26. The method of claim 17, wherein the compound modulates polycystic ovary syndrome. 27. Способ по п.17, в котором соединение модулирует ослабленную толерантность к глюкозе.27. The method of claim 17, wherein the compound modulates impaired glucose tolerance. 28. Способ по п.17, в котором соединение модулирует ожирение.28. The method of claim 17, wherein the compound modulates obesity. 29. Способ по п.17, в котором соединение модулирует диабет беременных.29. The method according to 17, in which the compound modulates the diabetes of pregnant women. 30. Способ по п.17, в котором соединение модулирует синдром X.30. The method according to 17, in which the compound modulates syndrome X. 31. Способ по п.17, в котором соединение модулирует атеросклероз.31. The method according to 17, in which the compound modulates atherosclerosis. 32. Способ по п.17, в котором соединение вводят в сочетании с соединением, выбранным из группы, состоящей из: сульфонилмочевины или другого секретора инсулина, тиазолидиндиона, фибрата, ингибитора HMG-CoA-редуктазы, бигуанида, смолы, связывающей желчную кислоту, никотиновой кислоты, ингибитора α-глюкозидазы и инсулина.32. The method according to 17, in which the compound is administered in combination with a compound selected from the group consisting of: sulfonylurea or another insulin secretion, thiazolidinedione, fibrate, HMG-CoA reductase inhibitor, biguanide, bile acid binding resin, nicotinic acid, α-glucosidase inhibitor and insulin. 33. Способ облегчения гиперлипидемии у млекопитающего, включающий введение указанному млекопитающему терапевтически эффективного количества (-)стереоизомера соединения формулы I33. A method of alleviating hyperlipidemia in a mammal, comprising administering to said mammal a therapeutically effective amount of a (-) stereoisomer of a compound of formula I
Figure 00000005
Figure 00000005
 где R - выбран из группы, состоящей из гидрокси, низшего аралкокси, ди-низшего алкиламино-низшего алкокси, низшего алканамидо низшего алкокси, бензамидо-низшего алкокси, уреидо-низшего алкокси, N'-низшего алкил-уреидо-низшего алкокси, карбамоил-низшего алкокси, галофеноксизамещенного низшего алкокси, карбамоилзамещенного фенокси, карбонил-низшего алкиламино, N,N-ди-низшего алкиламино-низшего алкиламино, галогензамещенного низшего алкиламино, гидроксизамещенного низшего алкиламино, низшего алканолилоскизамещенного низшего алкиламино, уреидо и низшего алкоксикарбониламино; иwhere R is selected from the group consisting of hydroxy, lower aralkoxy, di-lower alkylamino-lower alkoxy, lower alkanamido-lower alkoxy, benzamido-lower alkoxy, ureido-lower alkoxy, N'-lower alkyl-ureido-lower alkoxy, carbamoyl- lower alkoxy, halophenoxy substituted lower alkoxy, carbamoyl substituted phenoxy, carbonyl lower alkylamino, N, N-di-lower alkylamino lower alkylamino, halogen substituted lower alkylamino, hydroxy substituted lower alkylamino, lower alkanolylamino substituted lower alkyl eido and lower alkoxycarbonylamino; and Х представляет собой галоген; или его фармацевтически приемлемой соли, причем это соединение по существу не содержит своего (+)стереоизомера.X is halogen; or a pharmaceutically acceptable salt thereof, wherein the compound is substantially free of its (+) stereoisomer. 34. Способ по п.33, в котором соединение представляет собой соединение формулы II34. The method according to p, in which the compound is a compound of formula II
Figure 00000006
Figure 00000006
 где R2 - выбран из группы, состоящей из фенил-низшего алкила, низшего алканамидо-низшего алкила и бензамидо-низшего алкила.where R 2 is selected from the group consisting of phenyl lower alkyl, lower alkanamido lower alkyl, and benzamido lower alkyl. 35. Способ по п.33, в котором соединение представляет собой (-)2-ацетамидоэтил-4-хлорфенил-(3-трифторметилфенокси)ацетат.35. The method according to claim 33, wherein the compound is (-) 2-acetamidoethyl-4-chlorophenyl- (3-trifluoromethylphenoxy) acetate. 36. Способ по п.33, в котором соединение вводят путем внутривенного вливания, чрескожно или перорально.36. The method according to p, in which the compound is administered by intravenous infusion, transdermally or orally. 37. Способ по п.33, в котором соединение понижает уровень содержания холестерина, уровень содержания триглицеридов или оба этих показателя.37. The method of claim 33, wherein the compound lowers cholesterol, triglycerides, or both. 38. Способ по п.33, в котором вводимое количество соединения составляет от около 100 до около 3000 мг в день.38. The method according to p, in which the administered amount of the compound is from about 100 to about 3000 mg per day. 39. Способ по п.33, в котором вводимое количество соединения составляет от около 500 до около 1500 мг в день.39. The method according to p, in which the administered amount of the compound is from about 500 to about 1500 mg per day. 40. Способ по п.33, в котором вводимое количество соединения составляет от около 5 до около 250 мг в день.40. The method according to p, in which the administered amount of the compound is from about 5 to about 250 mg per day. 41. Способ по п.33, в котором соединение вводят вместе с фармацевтически приемлемым носителем.41. The method according to p, in which the compound is administered together with a pharmaceutically acceptable carrier. 42. Способ по п.33, в котором соединение вводят в сочетании с соединением, выбранным из группы, состоящей из сульфонилмочевины или другого секретера инсулина, тиазолидиндиона, фибрата, ингибитора HMG-CoA-редуктазы, бигуанида, смолы, связывающей желчную кислоту, никотиновой кислоты, ингибитора α-глюкозидазы и инсулина.42. The method according to claim 33, wherein the compound is administered in combination with a compound selected from the group consisting of sulfonylurea or another insulin secretion, thiazolidinedione, fibrate, HMG-CoA reductase inhibitor, biganide, bile acid binding resin, nicotinic acid , an inhibitor of α-glucosidase and insulin. 43. Фармацевтическая композиция, включающая фармацевтически приемлемый носитель и терапевтически эффективное количество (-)стереоизомера соединения формулы I43. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a (-) stereoisomer of a compound of formula I
Figure 00000007
Figure 00000007
 где R - выбран из группы, состоящей из гидрокси, низшего аралкокси, ди-низшего алкиламино-низшего алкокси, низшего алканамидо низшего алкокси, бензамидо-низшего алкокси, уреидо-низшего алкокси, N'-низшего алкил–уреидо-низшего алкокси, карбамоил-низшего алкокси, галофеноксизамещенного низшего алкокси, карбамоилзамещенного фенокси, карбонил-низшего алкиламино, N,N-ди-низшего алкиламино-низшего алкиламино, галогензамещенного низшего алкиламино, гидроксизамещенного низшего алкиламино, низшего алканолилоскизамещенного низшего алкиламино, уреидо и низшего алкоксикарбониламино; иwhere R is selected from the group consisting of hydroxy, lower aralkoxy, lower lower alkylamino lower alkoxy, lower alkanamido lower alkoxy, benzamide lower alkoxy, ureido lower alkoxy, N'-lower alkyl-ureido lower alkoxy, carbamoyl- lower alkoxy, halophenoxy substituted lower alkoxy, carbamoyl substituted phenoxy, carbonyl lower alkylamino, N, N-di-lower alkylamino lower alkylamino, halogen substituted lower alkylamino, hydroxy substituted lower alkylamino, lower alkanolylamino substituted lower alkyl reido and lower alkoxycarbonylamino; and Х представляет собой галоген; или его фармацевтически приемлемую соль, причем это соединение по существу не содержит своего (+)стереоизомера.X is halogen; or a pharmaceutically acceptable salt thereof, wherein the compound is substantially free of its (+) stereoisomer. 44. Фармацевтическая композиция по п.43, которая модулирует диабет II типа.44. The pharmaceutical composition according to item 43, which modulates type II diabetes. 45. Фармацевтическая композиция по п.43, которая модулирует резистентность к инсулину.45. The pharmaceutical composition according to item 43, which modulates insulin resistance. 46. Фармацевтическая композиция по п.43, которая модулирует гиперлипидемию.46. The pharmaceutical composition according to item 43, which modulates hyperlipidemia. 47. Фармацевтическая композиция по п.43, включающая терапевтически эффективное количество (-)стереоизомера формулы II47. The pharmaceutical composition according to item 43, comprising a therapeutically effective amount of a (-) stereoisomer of formula II
Figure 00000008
Figure 00000008
 где R2 - выбран из группы, состоящей из фенил-низшего алкила, низшего алканамидо-низшего алкила и бензамидо-низшего алкила.where R 2 is selected from the group consisting of phenyl lower alkyl, lower alkanamido lower alkyl, and benzamido lower alkyl. 48. Фармацевтическая композиция по п.43, в которой соединение представляет собой (-)2-ацетамидоэтил-4-хлорфенил-(3-трифторметилфенокси)ацетат.48. The pharmaceutical composition according to item 43, in which the compound is (-) 2-acetamidoethyl-4-chlorophenyl- (3-trifluoromethylphenoxy) acetate. 49. Фармацевтическая композиция по п.43 в форме таблеток или капсул.49. The pharmaceutical composition according to item 43 in the form of tablets or capsules. 50. Способ лечения гиперурикемии у млекопитающего, включающий введение введение указанному млекопитающему терапевтически эффективного количества (-)стереоизомера соединения формулы I50. A method of treating hyperuricemia in a mammal, comprising administering to said mammal a therapeutically effective amount of a (-) stereoisomer of a compound of formula I
Figure 00000009
Figure 00000009
 где R - выбран из группы, состоящей из гидрокси, низшего аралкокси, ди-низшего алкиламино-низшего алкокси, низшего алканамидо низшего алкокси, бензамидо-низшего алкокси, уреидо-низшего алкокси, N'-низшего алкил–уреидо-низшего алкокси, карбамоил-низшего алкокси, галофеноксизамещенного низшего алкокси, карбамоилзамещенного фенокси, карбонил-низшего алкиламино, N,N-ди-низшего алкиламино-низшего алкиламино, галогензамещенного низшего алкиламино, гидроксизамещенного низшего алкиламино, низшего алканолилоскизамещенного низшего алкиламино, уреидо и низшего алкоксикарбониламино; иwhere R is selected from the group consisting of hydroxy, lower aralkoxy, lower lower alkylamino lower alkoxy, lower alkanamido lower alkoxy, benzamide lower alkoxy, ureido lower alkoxy, N'-lower alkyl-ureido lower alkoxy, carbamoyl- lower alkoxy, halophenoxy substituted lower alkoxy, carbamoyl substituted phenoxy, carbonyl lower alkylamino, N, N-di-lower alkylamino lower alkylamino, halogen substituted lower alkylamino, hydroxy substituted lower alkylamino, lower alkanolylamino substituted lower alkyl reido and lower alkoxycarbonylamino; and Х представляет собой галоген;X is halogen; или его фармацевтически приемлемой соли, причем это соединение по существу не содержит своего (+)стереоизомера.or a pharmaceutically acceptable salt thereof, wherein the compound is substantially free of its (+) stereoisomer. 51. Способ по п.50, в котором соединение представляет собой соединение формулы II51. The method of claim 50, wherein the compound is a compound of formula II
Figure 00000010
Figure 00000010
 где R2 - выбран из группы, состоящей из фенил-низшего алкила, низшего алканамидо-низшего алкила и бензамидо-низшего алкила.where R 2 is selected from the group consisting of phenyl lower alkyl, lower alkanamido lower alkyl, and benzamido lower alkyl. 52. Способ по п.50, в котором соединение представляет собой (-)2-ацетамидоэтил-4-хлорфенил-(3-трифторметилфенокси)ацетат.52. The method of claim 50, wherein the compound is (-) 2-acetamidoethyl-4-chlorophenyl- (3-trifluoromethylphenoxy) acetate. 53. Способ по п.50, в котором соединение вводят вместе с фармацевтически приемлемым носителем.53. The method of claim 50, wherein the compound is administered together with a pharmaceutically acceptable carrier.
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