RU2007118932A - Xanthine derivatives with activity NM74A - Google Patents

Xanthine derivatives with activity NM74A Download PDF

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RU2007118932A
RU2007118932A RU2007118932/04A RU2007118932A RU2007118932A RU 2007118932 A RU2007118932 A RU 2007118932A RU 2007118932/04 A RU2007118932/04 A RU 2007118932/04A RU 2007118932 A RU2007118932 A RU 2007118932A RU 2007118932 A RU2007118932 A RU 2007118932A
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aryl
chemical compound
alkyl
compound according
heteroaryl
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Ричард Джонатан Дэниэл ХЭТЛИ (GB)
Ричард Джонатан Дэниэл Хэтли
Иван Лео ПИНТО (GB)
Иван Лео Пинто
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Смитклайн Бичам Корпорейшн (US)
Смитклайн Бичам Корпорейшн
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Priority claimed from GB0427079A external-priority patent/GB0427079D0/en
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    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3

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Claims (15)

1. По меньшей мере одно химическое соединение, выбранное из соединений формулы (I)1. At least one chemical compound selected from compounds of formula (I)
Figure 00000001
(I)
Figure 00000001
(I) и его фармацевтически приемлемые производные, гдеand its pharmaceutically acceptable derivatives, where R1 представляет собой группу, выбранную из водорода, C1-10алкила, C2-10алкенила, C2-10алкинила и -(алк)m-X-(алк)n-Y,R 1 represents a group selected from hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl and - (alk) m —X— (alk) n —Y, где X представляет собой A, A1, A2 или прямую связь;where X represents A, A1, A2 or a direct bond; A представляет собой группу, выбранную из циклоалкилена, циклоалкенилена, арила, гетероарила, гетероциклила, -CH2-OC(O)-;A represents a group selected from cycloalkylene, cycloalkenylene, aryl, heteroaryl, heterocyclyl, —CH 2 —OC (O) -; A1 представляет собой группу, выбранную изA1 is a group selected from -CH2-O-(CH2)qарил-O-, -CH2-O-(CH2)wN(R5)C(O)0-, -CH2-N(R5)C(O)O-, -CH2-N(R5)C(O)-, -CH2-(O)p-(CH2)qC(O)NR5-, -CH2-N(R5)C(O)N(R5)-, -CH2-C(O)N((CH2)WOH)-, -CH2-NR5-S(O)2-, CH2-S(O)2NR5-, -CH2-C(O)O-, -O-, -NR5-, -S-;-CH 2 -O- (CH 2 ) q aryl-O-, -CH 2 -O- (CH 2 ) w N (R 5 ) C (O) 0-, -CH 2 -N (R 5 ) C ( O) O-, -CH 2 -N (R 5 ) C (O) -, -CH 2 - (O) p - (CH 2 ) q C (O) NR 5 -, -CH 2 -N (R 5 ) C (O) N (R 5 ) -, -CH 2 -C (O) N ((CH 2 ) W OH) -, -CH 2 -NR 5 -S (O) 2 -, CH 2 -S ( O) 2 NR 5 -, -CH 2 -C (O) O-, -O-, -NR 5 -, -S-; A2 представляет собой -CH(OH)-;A2 represents —CH (OH) -; где X представляет собой A, A1 или A2, Y представляет собой группу, выбранную из гетероарила, гетероциклила, арила, циклоалкила, циклоалкенила, -O(CH2)n-арила, -C(O)O-арила, -CH(арил)2, -CH(гетероарил)2, -C1-6галоидалкила, -C(O)R4, -NR5R7, -C(O)NR5R7, -NR5C(O)R7, -NR5C(O)OR7, -C(O)(CH2)qOR4, галогена, циано, -N(R5)C(O)OR7, -OC(O)NR5R6, -NR5C(O)R8, -OR5, -OC(O)R4;where X represents A, A1 or A2, Y represents a group selected from heteroaryl, heterocyclyl, aryl, cycloalkyl, cycloalkenyl, -O (CH 2 ) n -aryl, -C (O) O-aryl, -CH (aryl ) 2 , -CH (heteroaryl) 2 , -C 1-6 haloalkyl, -C (O) R 4 , -NR 5 R 7 , -C (O) NR 5 R 7 , -NR 5 C (O) R 7 , -NR 5 C (O) OR 7 , -C (O) (CH 2 ) q OR 4 , halogen, cyano, -N (R 5 ) C (O) OR 7 , -OC (O) NR 5 R 6 , -NR 5 C (O) R 8 , -OR 5 , -OC (O) R 4 ; когда X представляет собой A1 и Y выбирают из -O(CH2)n-арила, -O-гетероарила, -OR5, -OC(O)R5, -NH-арила, -OC(O)NR5R6,when X is A1 and Y is selected from —O (CH 2 ) n -aryl, —O-heteroaryl, —OR 5 , —OC (O) R 5 , —NH-aryl, —OC (O) NR 5 R 6 , n является целым числом, выбранным из 2, 3, 4 и 5;n is an integer selected from 2, 3, 4 and 5; когда X представляет собой A1 и Y представляет собой -CF3, или когда X представляет собой A2, n является целым числом, выбранным из 1, 2, 3, 4 и 5;when X is A1 and Y is —CF 3 , or when X is A2, n is an integer selected from 1, 2, 3, 4, and 5; когда X представляет собой прямую связь, Y представляет собой группу, выбранную из -C(O)(CH2)qOR5, -C(O)-арила, -C(O)-гетероарила, -C(O)-гетероциклила, -гетероарила, -гетероциклила, -арила, -циклоалкила, -циклоаленила, -C1-6галоидалкила, -галогена, -циано, системы 3 или 4 конденсированных колец, -CH(арил)2, -CH(гетероарил)2, -OR5, -NR5R7, -NCOOR8, -(O)PC(O)NR5R6, -NR5C(O)R8, -OR5, -(O)PC(O)R4;when X is a direct bond, Y is a group selected from —C (O) (CH 2 ) q OR 5 , —C (O) aryl, —C (O) heteroaryl, —C (O) heterocyclyl , -heteroaryl, -heterocyclyl, -aryl, -cycloalkyl, -cycloalenyl, -C 1-6 haloalkyl, -halogen, -cyano, a system of 3 or 4 fused rings, -CH (aryl) 2 , -CH (heteroaryl) 2 , -OR 5 , -NR 5 R 7 , -NCOOR 8 , - (O) P C (O) NR 5 R 6 , -NR 5 C (O) R 8 , -OR 5 , - (O) P C (O ) R 4 ; когда Y включает кольцо, то кольцо может быть необязательно замещено одним или несколькими из C1-6алкила, C2-6алкенила, C2-6алкинила, галогена, -NH2, (CH2)q-NR5R7, -(CH2)q-(O)p-(CH2)q-N(R5)C(O)OR8, -(CH2)q-N(R5)C(O)R8, -(CH2)q-(O)p-(CH2)q-C(O)NR5R6, -(CH2)q-N(R5)C(O)N(R5)R6, -(CH2)q-C(O)N((CH2)mOH)R5, -(CH2)q-N(R5)-S(O)2R8, -CH2-S(O)2N(R5)R6, -C1-6галоидалкила, -OCF3, -OCH(F)2, -OCH2F, -COOR5, -OR5, -(R8)PCN, -S(O2)R9, -(CH2)nгетероарила, -(CH2)nгетероциклила, -(CH2)nциклоалкила, -(CH2)nциклоалкенила, -(CH2)nарила;when Y includes a ring, the ring may optionally be substituted with one or more of C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, halogen, —NH 2 , (CH 2 ) q —NR 5 R 7 , - (CH 2 ) q - (O) p - (CH 2 ) q -N (R 5 ) C (O) OR 8 , - (CH 2 ) q -N (R 5 ) C (O) R 8 , - (CH 2 ) q - (O) p - (CH 2 ) q -C (O) NR 5 R 6 , - (CH 2 ) q -N (R 5 ) C (O) N (R 5 ) R 6 , - (CH 2 ) q -C (O) N ((CH 2 ) m OH) R 5 , - (CH 2 ) q -N (R 5 ) -S (O) 2 R 8 , -CH 2 -S ( O) 2 N (R 5 ) R 6 , —C 1-6 haloalkyl, —OCF 3 , —OCH (F) 2 , —OCH 2 F, —COOR 5 , —OR 5 , - (R 8 ) P CN, -S (O 2 ) R 9 , - (CH 2 ) n heteroaryl, - (CH 2 ) n heterocyclyl, - (CH 2 ) n cycloalkyl, - (CH 2 ) n cycloalkenyl, - (CH 2 ) n aryl; R2 выбирают из водорода или C1-10алкила, C2-10алкенила, C2-10алкинила, циклоалкила, циклоалкенила, гетероциклила, арила и гетероарила, каждый из которых может быть необязательно замещен одним или несколькими из C1-10алкила, C2-10алкенила, C2-10алкинила, циклоалкила, гетероциклила, арила, гетероарила, C1-6галоидалкила, галогена, -CN, -OR4, -(CH2)nCOR4, -C(O)OR4, -OCOR4, -(CH2)nNR5R6, -(NH)pCONR5R6, -OCONR5R7 и -NHC(O)OR7;R 2 is selected from hydrogen or C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and heteroaryl, each of which may optionally be substituted with one or more of C 1-10 alkyl , C 2-10 alkenyl, C 2-10 alkynyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, C 1-6 haloalkyl, halogen, —CN, —OR 4 , - (CH 2 ) n COR 4 , —C (O) OR 4 , -OCOR 4 , - (CH 2 ) n NR 5 R 6 , - (NH) p CONR 5 R 6 , -OCONR 5 R 7 and -NHC (O) OR 7 ; R3 выбирают из фторированного C1-6алкила;R 3 is selected from fluorinated C 1-6 alkyl; R4 выбирают из водорода, C1-6алкила, C2-6алкенила, C2-6алкинила -(CH2)nциклоалкила, -(CH2)nциклоаленила, -(CH2)nгетероциклила, -(CH2)nарила и -(CH2)nгетероарила;R 4 is selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl - (CH 2 ) n cycloalkyl, - (CH 2 ) n cycloalenyl, - (CH 2 ) n heterocyclyl, - (CH 2 ) n aryl and - (CH 2 ) n heteroaryl; R5 и R6 выбирают из водорода и C1-4алкила;R 5 and R 6 are selected from hydrogen and C 1-4 alkyl; R7 выбирают из водорода, C1-6алкила, C2-6алкенила, C2-6алкинила, -(CH2)tциклоалкила, -(CH2)nциклоалкенила, -(CH2)tгетероциклила, -(CH2)tарила и -(CH2)tгетероарила;R 7 is selected from hydrogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, - (CH 2 ) t cycloalkyl, - (CH 2 ) n cycloalkenyl, - (CH 2 ) t heterocyclyl, - ( CH 2 ) t aryl and - (CH 2 ) t heteroaryl; R8 выбирают из C1-4алкила;R 8 is selected from C 1-4 alkyl; R9 выбирают из C1-6алкила, C2-6алкенила, C2-6алкинила -(CH2)nциклоалкила, -(CH2)nциклоаленила, -(CH2)nгетероциклила, -(CH2)nарила и -(CH2)nгетероарила, CN;R 9 is selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl - (CH 2 ) n cycloalkyl, - (CH 2 ) n cycloalenyl, - (CH 2 ) n heterocyclyl, - (CH 2 ) n aryl and - (CH 2 ) n heteroaryl, CN; m является целым числом, выбранным из 0, 1, 2, 3, 4 и 5;m is an integer selected from 0, 1, 2, 3, 4 and 5; n является целым числом, выбранным из 0, 1, 2, 3, 4 и 5;n is an integer selected from 0, 1, 2, 3, 4 and 5; p является целым числом, выбранным из 0 и 1;p is an integer selected from 0 and 1; q является целым числом, выбранным из 0, 1 и 2;q is an integer selected from 0, 1 and 2; t является целым числом, выбранным из 1 и 2;t is an integer selected from 1 and 2; w является целым числом, выбранным из 2, 3 и 4;w is an integer selected from 2, 3 and 4; при условии чтоprovided that i) когда R1 представляет собой водород или C1-3алкил, R2 отличен от R1;i) when R 1 is hydrogen or C 1-3 alkyl, R 2 is other than R 1 ; ii) когда R1 представляет собой этил и R3 представляет собой CF3, R2 отличен от CH2-CH=CH2; иii) when R 1 is ethyl and R 3 is CF 3 , R 2 is other than CH 2 —CH═CH 2 ; and iii) когда R1 представляет собой метил и R3 представляет собой CF3, R2 отличен от изобутила.iii) when R 1 is methyl and R 3 is CF 3 , R 2 is other than isobutyl. 2. По меньшей мере одно химическое соединение по п.1, где R1 выбирают из водорода, C1-10алкила и -(алк)m-X-(алк)n-Y.2. At least one chemical compound according to claim 1, wherein R 1 is selected from hydrogen, C 1-10 alkyl, and - (alk) m —X— (alk) n —Y. 3. По меньшей мере одно химическое соединение по п.1, где X представляет собой A или прямую связь.3. At least one chemical compound according to claim 1, where X represents A or a direct bond. 4. По меньшей мере одно химическое соединение по п.1, где R1 выбирают из водорода и C1-6алкила.4. At least one chemical compound according to claim 1, wherein R 1 is selected from hydrogen and C 1-6 alkyl. 5. По меньшей мере одно химическое соединение по п.1, где R2 выбирают из C4-6алкила.5. At least one chemical compound according to claim 1, wherein R 2 is selected from C 4-6 alkyl. 6. По меньшей мере одно химическое соединение по п.1, где R3 представляет собой CF3.6. At least one chemical compound according to claim 1, where R 3 represents CF 3 . 7. По меньшей мере одно химическое соединение по любому из пп.1-6 для применения в медицине или ветеринарии.7. At least one chemical compound according to any one of claims 1 to 6 for use in medicine or veterinary medicine. 8. По меньшей мере одно химическое соединение по любому из пп.1-6, для применения при лечении нарушений метаболизма липидов, включая дислипидемию и гиперлипопротеинемию и/или воспалительных заболеваний или состояний.8. At least one chemical compound according to any one of claims 1 to 6, for use in the treatment of disorders of lipid metabolism, including dyslipidemia and hyperlipoproteinemia and / or inflammatory diseases or conditions. 9. По меньшей мере одно химическое соединение по любому из пп.1-6, для применения при лечении диабетической дислипидемии, смешанной дислипидемии, сердечной недостаточности, гиперхолестеринемии, сердечно-сосудистого заболевания, включая атеросклероз, артериосклероз и гипертриглицеридемию, диабет II-го типа, диабет I-го типа, инсулинорезистентность, гиперлипидемию, нервную анорексию, ожирение, коронарно-артериальное заболевание, тромбоз, ангину, хроническую почечную недостаточность, болезнь периферических сосудов или инсульт.9. At least one chemical compound according to any one of claims 1 to 6, for use in the treatment of diabetic dyslipidemia, mixed dyslipidemia, heart failure, hypercholesterolemia, cardiovascular disease, including atherosclerosis, arteriosclerosis and hypertriglyceridemia, type II diabetes, type I diabetes, insulin resistance, hyperlipidemia, anorexia nervosa, obesity, coronary arterial disease, thrombosis, tonsillitis, chronic renal failure, peripheral vascular disease or stroke. 10. По меньшей мере одно химическое соединение по любому из пп.1-6, для применения в производстве лекарственного препарата для лечения нарушений метаболизма липидов, включая дислипидемию и гиперлипопротеинемию и/или воспалительных заболеваний или состояний.10. At least one chemical compound according to any one of claims 1 to 6, for use in the manufacture of a medicament for the treatment of disorders of lipid metabolism, including dyslipidemia and hyperlipoproteinemia and / or inflammatory diseases or conditions. 11. По меньшей мере одно химическое соединение по любому из пп.1-6, для применения в производстве лекарственного препарата для лечения диабетической дислипидемии, смешанной дислипидемии, сердечной недостаточности, гиперхолестеринемии, сердечно-сосудистого заболевания, включая атеросклероз, артериосклероз и гипертриглицеридемию, диабет II-го типа, диабет I-го типа, инсулинорезистентность, гиперлипидемию, нервную анорексию, ожирение, коронарно-артериальное заболевание, тромбоз, ангину, хроническую почечную недостаточность, болезнь периферических сосудов или инсульт.11. At least one chemical compound according to any one of claims 1 to 6, for use in the manufacture of a medicament for the treatment of diabetic dyslipidemia, mixed dyslipidemia, heart failure, hypercholesterolemia, cardiovascular disease, including atherosclerosis, arteriosclerosis and hypertriglyceridemia, diabetes II type I diabetes, type I diabetes, insulin resistance, hyperlipidemia, anorexia nervosa, obesity, coronary arterial disease, thrombosis, tonsillitis, chronic renal failure, peripheral disease vascular vessels or stroke. 12. По меньшей мере одно химическое соединение по любому из пп.1-6, для применения в производстве лекарственного препарата для лечения состояния, где субактивация рецептора HM74A делает свой вклад в состояние или где активация рецептора будет полезна.12. At least one chemical compound according to any one of claims 1 to 6, for use in the manufacture of a medicament for the treatment of a condition where subactivation of the HM74A receptor contributes to the condition or where activation of the receptor will be useful. 13. Фармацевтическая композиция, содержащая по меньшей мере одно химическое соединение по любому из пп.1-6 и один или несколько фармацевтически приемлемых разбавителей, эксципиентов или носителей.13. A pharmaceutical composition comprising at least one chemical compound according to any one of claims 1 to 6 and one or more pharmaceutically acceptable diluents, excipients or carriers. 14. Комбинация для введения совместно или раздельно, последовательно или одновременно в отдельных или объединенных фармацевтических композициях, указанная комбинация содержит по меньшей мере одно химическое соединение по любому из пп.1-6 совместно с другим терапевтически активным агентом.14. A combination for administration together or separately, sequentially or simultaneously in separate or combined pharmaceutical compositions, said combination contains at least one chemical compound according to any one of claims 1-6 together with another therapeutically active agent. 15. Фармацевтическая композиция, содержащая 15. A pharmaceutical composition comprising (i) по меньшей мере одно химическое соединение по любому из пп.1-6;(i) at least one chemical compound according to any one of claims 1 to 6; (ii) одно или несколько активных ингредиентов, выбранных из статинов, фибратов, смол, связывающих желчные кислоты и никотиновой кислоты; и(ii) one or more active ingredients selected from statins, fibrates, bile resins and nicotinic acid binding resins; and (iii) один или несколько фармацевтически приемлемых разбавителей, эксципиентов или носителей.(iii) one or more pharmaceutically acceptable diluents, excipients or carriers.
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