RU2003110577A - HETEROCYCLIC COMPOUNDS CONNECTING TO CHEMOKINE RECEPTORS - Google Patents

HETEROCYCLIC COMPOUNDS CONNECTING TO CHEMOKINE RECEPTORS

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RU2003110577A
RU2003110577A RU2003110577/04A RU2003110577A RU2003110577A RU 2003110577 A RU2003110577 A RU 2003110577A RU 2003110577/04 A RU2003110577/04 A RU 2003110577/04A RU 2003110577 A RU2003110577 A RU 2003110577A RU 2003110577 A RU2003110577 A RU 2003110577A
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Prior art keywords
benzenedimethanamine
pyridinylmethyl
tetrahydro
quinolinyl
ylmethyl
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RU2003110577/04A
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Russian (ru)
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RU2289581C2 (en
Inventor
Гари БРИДЖЕР
Ренато СКЕРЛДЖ
Эл КЭЛЛЕР
Кертис ХАРВИГ
Дэвид БОГУЦКИЙ
Тревор Р. УИЛСОН
Джейсон КРОФОРД
Эрнест Дж. МАКИЧЕРН
Бем АТСМА
Сиквайао НАН
Юанкси ЗОУ
Доминик СХОЛС
Кристофер Деннис СМИТ
ФЛУРИ Розариа Мария ДИ
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Анормед, Инк.
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Claims (19)

1. Соединение формулы1. The compound of the formula
Figure 00000001
Figure 00000001
 и его соли и пролекарства, гдеand its salts and prodrugs, where кольцо А необязательно содержит гетероатом, выбранный из N, O или S;ring A optionally contains a heteroatom selected from N, O or S; пунктирные линии представляют необязательную ненасыщенность;dashed lines represent optional unsaturation; R1, R2 и R3 представляют заместители, не создающие препятствий;R 1 , R 2 and R 3 are non-obstructing substituents; k равно 0-4;k is 0-4; m равно 0-2;m is 0-2; L1 представляет связующее звено 1,5-10
Figure 00000002
;L 1 represents a link 1,5-10
Figure 00000002
; Х представляет незамещенный или замещенный С или N или представляет О или S;X represents unsubstituted or substituted C or N or represents O or S; Ar представляет остаток ароматического фрагмента;Ar represents the remainder of the aromatic fragment; каждый n независимо равен 0-2;each n is independently 0-2; каждый R независимо представляет Н или алкил (1-6С); иeach R independently represents H or alkyl (1-6C); and Y представляет ароматическую или гетероароматическую или другую гетероциклическую группу.Y represents an aromatic or heteroaromatic or other heterocyclic group. 2. Соединение по п.1, при условии что указанное соединение отлично от2. The compound according to claim 1, provided that the specified connection is different from MD7186: N-(5-этилтиофен-2-илметил)-N’-(2-пиридинилметил)-N-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,MD7186: N- (5-ethylthiophen-2-ylmethyl) -N ’- (2-pyridinylmethyl) -N- (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine, AMD7208: N-(1-метилпиррол-2-илметил)-N’-(2-пиридинилметил)-N-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD7208: N- (1-methylpyrrol-2-ylmethyl) -N ’- (2-pyridinylmethyl) -N- (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine, AMD7222: N-(1-метилбензимидазол-2-илметил)-N’-(2-пиридинилметил)-N-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD7222: N- (1-methylbenzimidazol-2-ylmethyl) -N ’- (2-pyridinylmethyl) -N- (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine, AMD8780: N-(2-пиридинилметил)-N’-(транс-2-аминоциклогексил)-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина (бромоводородной соли),AMD8780: N- (2-pyridinylmethyl) -N ’- (trans-2-aminocyclohexyl) -N’ - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine (hydrobromic salt), AMD8931: N-(2-пиридинилметил)-N-(4-фенил-1Н-имидазол-2-илметил)-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8931: N- (2-pyridinylmethyl) -N- (4-phenyl-1H-imidazol-2-ylmethyl) -N '- (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine , AMD8821: N-(2-пиридинилметил)-N’-[2-фуранилметил]-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8821: N- (2-pyridinylmethyl) -N ’- [2-furanylmethyl] -N’ - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine, AMD8828: N-(2-пиридинилметил)-N’-[2-[(2-фуранилметил)амино]этил]-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8828: N- (2-pyridinylmethyl) -N '- [2 - [(2-furanylmethyl) amino] ethyl] -N' - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4- benzenedimethanamine, AMD8835: N-(2-пиридинилметил)-N’-[2-[(1Н-имидазол-2-илметил)амино]этил]-N’-(1,2,3,4-тетрагидро-1-нафталинил)-1,4-бензолдиметанамина,AMD8835: N- (2-pyridinylmethyl) -N '- [2 - [(1H-imidazol-2-ylmethyl) amino] ethyl] -N' - (1,2,3,4-tetrahydro-1-naphthalenyl) - 1,4-benzenedimethanamine, AMD8836: N-(2-пиридинилметил)-N’-[2-тиофенилметил]-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8836: N- (2-pyridinylmethyl) -N ’- [2-thiophenylmethyl] -N’ - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine, AMD8839: N-(2-пиридинилметил)-N’-(транс-2-аминоциклопентил)-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8839: N- (2-pyridinylmethyl) -N ’- (trans-2-aminocyclopentyl) -N’ - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine, AMD8841: N-(2-пиридинилметил)-N’-[2-тиазолилметил]-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8841: N- (2-pyridinylmethyl) -N ’- [2-thiazolylmethyl] -N’ - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine, AMD8751: N-(2-пиридинилметил)-N’-(1Н-имидазол-2-илметил)-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8751: N- (2-pyridinylmethyl) -N ’- (1H-imidazol-2-ylmethyl) -N’ - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine, AMD8887: N-(2-пиридинилметил)-N’-[2-[(1Н-имидазол-2-илметил)амино]этил]-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8887: N- (2-pyridinylmethyl) -N '- [2 - [(1H-imidazol-2-ylmethyl) amino] ethyl] -N' - (5,6,7,8-tetrahydro-8-quinolinyl) - 1,4-benzenedimethanamine, AMD8728: N-(2-пиридинилметил)-N’-[2-пирролилметил]-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8728: N- (2-pyridinylmethyl) -N ’- [2-pyrrolylmethyl] -N’ - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine, AMD8907: N-(2-пиридинилметил)-N’-(1Н-бензимидазол-2-илметил]-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8907: N- (2-pyridinylmethyl) -N ’- (1H-benzimidazol-2-ylmethyl] -N’ - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine, AMD8926: N-(2-пиридинилметил)-N’-(5-нитро-1Н-бензимидазол-2-илметил]-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8926: N- (2-pyridinylmethyl) -N '- (5-nitro-1H-benzimidazol-2-ylmethyl] -N' - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4- benzenedimethanamine, AMD8927: N-(2-пиридинилметил)-N’-(5,6-диметил-1Н-бензимидазол-2-илметил]-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина,AMD8927: N- (2-pyridinylmethyl) -N '- (5,6-dimethyl-1H-benzimidazol-2-ylmethyl] -N' - (5,6,7,8-tetrahydro-8-quinolinyl) -1, 4-benzenedimethanamine, AMD8929: N-(2-пиридинилметил)-N’-[(1Н)-5-азабензимидазол-2-илметил]-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина илиAMD8929: N- (2-pyridinylmethyl) -N '- [(1H) -5-azabenzimidazol-2-ylmethyl] -N' - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4- benzenedimethanamine or AMD8764: N-(2-пиридинилметил)-N’-(2-бензоксазолил)-N’-(5,6,7,8-тетрагидро-8-хинолинил)-1,4-бензолдиметанамина.AMD8764: N- (2-pyridinylmethyl) -N ’- (2-benzoxazolyl) -N’ - (5,6,7,8-tetrahydro-8-quinolinyl) -1,4-benzenedimethanamine. 3. Соединение по п.1 или 2, где L1 связан с положением 2 кольца Е.3. The compound according to claim 1 or 2, where L 1 is associated with position 2 of the ring E. 4. Соединение по п.3, где пунктирная линия в кольце Е представляет двойную связь между показанным атомом азота и положением 2.4. The compound according to claim 3, where the dashed line in the ring E represents a double bond between the shown nitrogen atom and position 2. 5. Соединение по п.4, где R2 и R3 связаны с образованием бензозаместителя в кольце Е.5. The compound according to claim 4, where R 2 and R 3 are associated with the formation of a benzosubstituent in ring E. 6. Соединение по п.1, где кольцо А является насыщенным.6. The compound according to claim 1, where ring A is saturated. 7. Соединение по п.6, где m равно 1 и k равно 0 или 1.7. The compound according to claim 6, where m is 1 and k is 0 or 1. 8. Соединение формулы8. The compound of the formula
Figure 00000003
Figure 00000003
 и его соли и пролекарства, гдеand its salts and prodrugs, where R, m, n, Ar и каждый Y, такие как определено для формулы 1;R, m, n, Ar and each Y, such as defined for formula 1; каждый Z независимо представляет CR2, NR, О или S, при условии что только два Z могут быть отличными от CR2; иeach Z independently represents CR 2 , NR, O, or S, provided that only two Z can be different from CR 2 ; and L2 представляет связующее звено 1,5-8
Figure 00000004
.L 2 represents a link 1,5-8
Figure 00000004
. 9. Соединение по п.8, где L2 представляет метилен или этилен.9. The compound of claim 8, where L 2 represents methylene or ethylene. 10. Соединение по п.8, где m равно 1 и все Z представляют CR2.10. The compound of claim 8, where m is 1 and all Z are CR 2 . 11. Соединение по п.10, где все Z представляют СН2.11. The compound of claim 10, where all Z are CH 2 . 12. Соединение по п.8, где каждый Y независимо представляет пиримидил, пиридил, фенил, бензимидазол или бензоксазол.12. The compound of claim 8, where each Y independently represents pyrimidyl, pyridyl, phenyl, benzimidazole or benzoxazole. 13. Соединение формулы13. The compound of the formula
Figure 00000005
Figure 00000005
 и его соли и пролекарства, гдеand its salts and prodrugs, where W1 представляет моноциклическую (5-6-членную) или конденсированную бициклическую (8-12-членную) незамещенную или замещенную кольцевую систему, содержащую по крайней мере один гетероатом, выбранный из N, O и S;W 1 represents a monocyclic (5-6 membered) or fused bicyclic (8-12 membered) unsubstituted or substituted ring system containing at least one heteroatom selected from N, O and S; W2 представляет Н или выбран из группы, состоящей из необязательно замещенной С1-6 алкильной группы; С0-6 алкильной группы, замещенной необязательно замещенной ароматической или гетероциклической группой; необязательно замещенной С0-6 алкиламино- или С3-7 циклоалкиламиногруппы и необязательно замещенной карбонильной или сульфонильной группы;W 2 represents H or is selected from the group consisting of an optionally substituted C 1-6 alkyl group; A C 0-6 alkyl group substituted with an optionally substituted aromatic or heterocyclic group; an optionally substituted C 0-6 alkylamino or C 3-7 cycloalkylamino group and an optionally substituted carbonyl or sulfonyl group; Ar, R и n, такие как определено для формулы 1, иAr, R and n, as defined for formula 1, and
Figure 00000006
Figure 00000006
 представляет насыщенное или ненасыщенное 5-членное кольцо, содержащее 1-2 гетероатома, выбранных из N, O или S.represents a saturated or unsaturated 5-membered ring containing 1-2 heteroatoms selected from N, O or S. 14. Соединение формулы14. The compound of the formula
Figure 00000007
Figure 00000007
 или его соли и пролекарства, гдеor its salts and prodrugs, where W1 и W2, такие как определено в п.13, и Ar, R и n, такие как определено в п.1, иW 1 and W 2 , such as defined in clause 13, and Ar, R and n, such as defined in clause 1, and
Figure 00000008
Figure 00000008
 представляет конденсированную кольцевую систему из 10 членов, необязательно содержащую 1 или 2 гетероатома, выбранных из N, O и S.represents a condensed ring system of 10 members, optionally containing 1 or 2 heteroatoms selected from N, O and S. 15. Фармацевтическая композиция, содержащая эффективное терапевтическое количество соединения по любому из пп.1-14.15. A pharmaceutical composition comprising an effective therapeutic amount of a compound according to any one of claims 1-14. 16. Применение соединения по любому из пп.1-14 для изготовления лекарственного средства для лечения больных, инфицированных ВИЧ или ВИК.16. The use of a compound according to any one of claims 1 to 14 for the manufacture of a medicament for the treatment of patients infected with HIV or VIC. 17. Применение соединения по любому из пп.1-14 для лечения больных, инфицированных ВИЧ или ВИК.17. The use of compounds according to any one of claims 1 to 14 for the treatment of patients infected with HIV or VIC. 18. Фармацевтическая композиция для лечения больного путем модулирования хемокинового рецептора, содержащая эффективное терапевтическое количество соединения по любому из пп.1-14.18. A pharmaceutical composition for treating a patient by modulating a chemokine receptor, comprising an effective therapeutic amount of a compound according to any one of claims 1-14. 19. Применение соединения по любому из пп.1-14 для изготовления лекарственного средства для модулирования хемокинового рецептора.19. The use of a compound according to any one of claims 1-14 for the manufacture of a medicament for modulating a chemokine receptor.
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