RU2004134561A - Производные дикетогидразина и лекарственные средства, содержащие эти производные в качестве активного ингредиента - Google Patents

Производные дикетогидразина и лекарственные средства, содержащие эти производные в качестве активного ингредиента Download PDF

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RU2004134561A
RU2004134561A RU2004134561/04A RU2004134561A RU2004134561A RU 2004134561 A RU2004134561 A RU 2004134561A RU 2004134561/04 A RU2004134561/04 A RU 2004134561/04A RU 2004134561 A RU2004134561 A RU 2004134561A RU 2004134561 A RU2004134561 A RU 2004134561A
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alkyl
substituted
disease
cusa
compound
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RU2004134561/04A
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RU2368600C2 (ru
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ХАТАЯМА Акира (JP)
ХАТАЯМА Акира
ЦУРУТА Хироши (JP)
ЦУРУТА Хироши
ОЧИ Ясуо (JP)
ОЧИ Ясуо
ИМАВАКА Харуо (JP)
ИМАВАКА Харуо
ОХМОТО Казуюки (JP)
ОХМОТО Казуюки
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Оно Фармасьютикл Ко., Лтд. (Jp)
Оно Фармасьютикл Ко., Лтд.
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    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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Claims (23)

1. Соединение формулы (I)
Figure 00000001
где R представляет собой (1) водород, (2) СусА, (3) С1-8 алкил, необязательно замещенный 1-5 группами, выбранными из галогена, СусА, нитро, трифторметила и циано,
Figure 00000002
Figure 00000003
Figure 00000004
Figure 00000005
Figure 00000006
Figure 00000007
или
Figure 00000008
где СусА представляет собой С3-15 моно-, би- или трициклическое карбокольцо или 3-15-членное моно-, би- или трициклическое гетерокольцо, включающее 1-4 атома азота, 1-2 атома кислорода и/или 1-2 атома серы;
R16 представляет собой (1) С1-8 алкил, (2) С2-8 алкенил, (3) С2-8 алкинил, (4) СусА или
(5) С1-8 алкил, С2-8 алкенил или С2-8 алкинил, замещенный 1-5 группами, выбранными из галогена, нитро, трифторметила, циано, СусА, -NR18R19, -OR18, -SR18, -NHC(О)-CycA и -NHC(O)-(C1-8 алкила);
R17, R18 и R19 каждый независимо представляет собой водород, С1-4 алкил, СусА, С1-4 алкил, замещенный СусА,
АА1 представляет собой (1) связь, или
Figure 00000009
где R1 и R2 каждый независимо представляет собой (i) водород, (ii) С1-8 алкил, (iii) СусА или (iv) С1-8 алкил, замещенный 1-5 группами, выбранными из следующих (а)-(и):
(a) –NR21R22, (б) -OR23, (в) -SR23, (г) -COR24, (д) -NR25C(O)NR21R22, (е) гуанидино, (ж) амидино, (з) СусА, (и) –NR25SO2R21; или
R1 и R2 вместе образуют С2-8 алкилен, где один атом углерода алкиленовой цепи может быть замещен атомом кислорода, серы или –NR20- и алкилен может быть замещен –NR21R22, -OR23 или оксо,
где R20 представляет собой водород, С1-4 алкил, -С(O)O-(С1-4 алкил), СусА или С1-4 алкил, замещенный СусА; R21, R22, R23 и R25 каждый независимо представляет собой водород, С1-4 алкил, СусА или С1-4 алкил, замещенный СусА; R24 представляет собой С1-4 алкил, СусА, -NR21R22, -OR23,-SR23 или С1-4 алкил, замещенный СусА,
R3 представляет собой водород, С1-8 алкил, СусА или С1-8 алкил, замещенный СусА, или R3 может вместе с R1 образовывать С2-6 алкилен, где один атом углерода алкиленовой цепи может быть замещен атомом кислорода, серы или –NR20- и алкилен может быть замещен –NR21R22, -OR23, -SR23 или оксо, или
R и АА1 могут вместе образовывать
Figure 00000010
где СусВ представляет собой 5-12-членное моно- или бициклическое гетерокольцо и другие символы имеют значения, указанные выше,
АА2 представляет собой (1) связь,
Figure 00000011
Figure 00000012
или
Figure 00000013
где R4 и R5 каждый независимо представляет собой (i) водород, (ii) С1-8 алкил, (iii) СусА или (iv) С1-8 алкил, замещенный 1-5 группами, выбранными из следующих (а)-(и):
(a) –NR31R32, (б) -OR33, (в) -SR33, (г) -COR34, (д) -NR35C(O)NR31R32, (е) гуанидино, (ж) амидино, (з) СусА, (и) –NR35SO2R31; или
R4 и R5 могут вместе образовывать С2-8 алкилен, где один атом углерод алкиленовой цепи может быть замещен атомом кислорода, серы или –NR30- и алкилен может быть замещен –NR31R32, -OR33, -SR33 или оксо,
где R30 представляет собой водород, С1-4 алкил, -С(O)O-(С1-4 алкил), СусА или С1-4 алкил, замещенный СусА; R31, R32, R33 и R35 каждый независимо представляет собой водород, С1-4 алкил, СусА или С1-4 алкил, замещенный СусА; R34 представляет собой С1-4 алкил, СусА, -NR31R32, -OR33, -SR33 или С1-4 алкил, замещенный СусА,
R6 представляет собой водород, С1-8 алкил, СусА или С1-8 алкил, замещенный СусА, или R6 может вместе с R4 или R образовывать С2-6 алкилен, где один атом углерода алкиленовой цепи может быть замещен атомом кислорода, серы или –NR30- и алкилен может быть замещен NR31R32, OR33, SR33 или оксо,
R38 представляет собой водород, С1-4 алкил, СусА или С1-4 алкил, замещенный СусА или
когда АА1 представляет собой связь, R38 может вместе с R образовывать С2-6 алкилен, где один атом углерода алкиленовой цепи может быть замещен атомом кислорода, серы или –NR37-, где R37 представляет собой водород или С1-4 алкил,
СусС представляет собой 3-17-членное моно- или бициклическое гетерокольцо, CycD представляет собой С3-14-моно- или бициклическое карбокольцо или 3-14-членное моно- или бициклическое гетерокольцо, или
АА2 может вместе с АА1 образовывать
Figure 00000014
или
Figure 00000015
где СусЕ представляет собой 4-18-членное моно- или бициклическое гетерокольцо, CycF представляет собой 5-8-членное моноциклическое гетерокольцо, и другие символы имеют значения, указанные выше,
R7 и R8 каждый независимо представляет собой (1) водород, (2) С1-8 алкил, (3) СусА или (4) С1-8 алкил, замещенный 1-5 группами, выбранными из следующих (i)~(x);
(i) –NR41R42, (ii) -OR43, (iii) -SR43, (iv) -COR44, (v) –NR45C(O)NR41R42, (vi) гуанидино, (vii) амидино, (viii) CycA, (ix) –NR45SO2R41, (x) –P(O)(OR46)(OR47), или
R7 и R8 могут вместе образовывать С2-8 алкилен, где один атом углерода алкиленовой цепи может быть замещен атомом кислорода, серы или –NR40-и алкилен может быть замещен –NR41R42, -OR43, -SR43 или оксо,
R40 представляет собой водород, С1-4 алкил, -С(O)O-(С1-4 алкил), СусА или С1-4 алкил, замещенный СусА,
R41, R42, R43 и R45 каждый независимо представляет собой водород, С1-4 алкил, СусА или С1-4 алкил, замещенный СусА, R44 представляет собой С1-4 алкил, СусА, -NR41R42, -OR43, -SR43 или С1-4 алкил, замещенный СусА,
R46 и R47 каждый независимо представляет собой водород или С1-8 алкил,
R9 представляет собой водород, С1-8 алкил, СусА или С1-8 алкил, замещенный СусА или
R9 может вместе с R7 или R образовывать С2-6 алкилен, где один атом углерода алкиленовой цепи может быть замещен атомом кислорода, серы или –NR40- и алкилен может быть замещен –NR41R42, -OR43, -SR43 или оксо, где все символы имеют значения, указанные выше,
Figure 00000016
представляет собой группу, выбранную из следующих (1), (2) или (3):
Figure 00000017
где RA1 и RA2 каждый независимо представляет собой (i) водород, (и) С1-8 алкил, (iii) C2-8 алкенил, (iv) –NRZ1RZ2, (v) –ORZ3, (vi) –SRZ3, (vii) –CORZ4, (viii) CycP или (ix) С1-8 алкил или C2-8 алкенил, замещенные 1-5 группами, выбранными из CycP, -NRZ1RZ2, -ORZ3, -SRZ3, -CORZ4, -SO2RZ4, -COORZ3, -CONRZ1RZ2, -SO2NRZ1RZ2 и -Р(O)(ORZ5)(ORZ6),
где RZ1 и RZ2 каждый независимо представляет собой водород, С1-8 алкил, C2-8 алкенил, CycP, C2-8 ацил или С1-8 алкил, замещенный CycP, C2-8 ацилом, С1-8 алкокси, С1-8 алкилтио, С1-8 моноалкиламино или ди(С1-8 алкил)амино;
RZ3 представляет собой водород, С1-8 алкил, C2-8 алкенил, CycP или С1-8 алкил, замещенный 1-5 группами, выбранными из CycP, С1-8 алкокси, С1-8 алкилтио, амино, С1-8 моноалкиламино, ди(С1-8 алкил)амино и C2-8 ацила;
RZ4 представляет собой С1-8 алкил, CycP или С1-8 алкил, замещенный 1-5 группами, выбранными из CycP, С1-8 алкокси, С1-8 алкилтио, моно(С1-8 алкил)амино, ди(С1-8 алкил)амино или C2-8 ацила;
RZ5 и RZ6 каждый независимо представляет собой водород или С1-8 алкил,
CycP представляет собой С4-10 карбокольцо или 5-10-членное гетерокольцо, включающее 1-4 атома азота, 1-2 атома кислорода и/или 1-2 атома серы и R10 имеет значения, указанные выше, или
RA1 и RA2 может вместе с соседним атомом углерода обозначать СусН
Figure 00000018
где СусН представляет собой С4-10 моно- или бициклическое карбокольцо или 4-10-членное моно- или бициклическое гетерокольцо и R10 имеет значения, указанные выше, или
RA1 и R10 может вместе с соседними атомами углерода и азота представлять собой
Figure 00000019
где CycJ представляет собой 5-10-членное моно- или бициклическое гетерокольцо и RA2 имеет значения, указанные выше,
Figure 00000020
где RA3 представляет собой (i) С1-8 алкил, (ii) C2-8 алкенил, (iii)-NRZ1RZ2, (ix) -ORZ3, (v) –SRZ3, (vi) –CORZ4, (vii) CycP или С1-8 алкил или C2-8 алкенил, замещенные 1-5 группами, выбранными из –NRZ1RZ2, -ORZ3, -SRZ3, -CORZ4, -SO2RZ4, CycP и –P(O)(ORZ5)(ORZ6), где все символы имеют значения, указанные выше,
RA4 представляет собой (i) водород, (ii) С1-8 алкил, (iii) C2-8 алкенил, (iv) -COR, (v) CycP или (vi) С1-8 алкил или C2-8 алкенил, замещенные 1-5 группами, выбранными из CycP, -NRZ1RZ2, -ORZ3, -SRZ3, -CORZ4, -SO2RZ4, -COORZ3, -CONRZ1RZ2, -SO2NRZ1RZ2 и -P(O)(ORZ5)(ORZ6), где все символы имеют значения, указанные выше,
R10 имеет значения, указанные выше, или
RA3 и RA4 могут вместе с соседними атомами углерода и азота представлять собой
Figure 00000021
где СусК представляет собой 5-10-членное моно- или бициклическое гетерокольцо и R10 имеет значения, указанные выше,
RA3 и R10 могут вместе с соседними атомами углерода и азота представлять собой
Figure 00000022
где CycL представляет собой 5-10-членное моно- или бициклическое гетерокольцо и RA4 имеет значения, указанные выше,
Figure 00000023
где n имеет значение 1 или 2, и другие символы имеют значения, указанные выше, и RA3 и RA4 могут вместе с соседними атомами азота и серы представлять собой
Figure 00000024
где СусМ представляет собой 5-10-членное моно- или бициклическое гетерокольцо и другие символы имеют значения, указанные выше, или
RA3 и R10 могут вместе с атомами азота и серы представлять собой
Figure 00000025
где CycN представляет собой 5-10-членное моно- или бициклическое гетерокольцо и другие символы имеют значения, указанные выше, СусА, СусВ, СусС, CycD, CycE, CycF, CycH, CycJ, CycK, CycL, CycM, CycN и СусР может быть каждый независимо замещен 1-5 R27,
R27 представляет собой (1) С1-8 алкил, (2) галоген, (3) –NR11R12, (4) -OR13, (5) -SR13, (6) CycG, (7) нитро, (8) циано, (9) оксо, (10) -COR14, (11) -SO2R14, (12) -P(O)(OR15)(OR16), (13) гуанидино, (14) амидино или (15) C1-8 алкил, замещенный 1-5 группами, выбранными из следующих (i)-(xii):
(i) галоген, (ii) -NR11R12, (iii) -OR13, (iv) -SR13, (v) CycG, (vi) нитро, (vii) циано, (viii) -COR14, (ix) -SO2R14, (x) -P(O)(OR15)(OR16), (xi) гуанидино, (xii) амидино
где R11 и R12 каждый независимо представляет собой водород, С1-4 алкил, С1-4 алкокси, -С(O)O-(С1-4 алкил), CycG или С1-4 алкил, замещенный CycG,
R13 представляет собой водород, С1-4 алкил, трифторметил, CycG или С1-4 алкил, замещенный CycG,
CycG каждый независимо представляет собой С4-10 моно- или бициклическое карбокольцо или 5-10-членное моно- или бициклическое гетерокольцо, включающее 1-4 атома азота, 1-2 атома кислорода и/или 1-2 атома серы,
R14 представляет собой С1-8 алкил, CycG, -NR11R12, -OR13, -SR13 или C1-8 алкил, замещенный CycG, -NR11R12, -OR13 или -SR13,
R15 каждый независимо представляет собой водород или Cl-8 алкил, когда в CycH, CycJ, CycK, CycL, CycM или CycN присутствует насыщенный атом углерода, насыщенный атом углерода может образовывать спиро-связь с СусО (где CycQ представляет собой С3-10 насыщенное или частично ненасыщенное моноциклическое карбокольцо или 5-8-членное насыщенное или частично ненасыщенное моноциклическое гетерокольцо, включающее 1 –NRQ -, где RQ представляет собой C1-8 алкил, С2-8 ацил, -SO2-(С1-8 алкил), бензоил, бензолсульфонил или толуолсульфонил), 1 атом кислорода и/или 1 атом серы, которые могут быть окислены, или его фармацевтически приемлемые соли.
2. Соединение по п.1, где в соединении формулы (I)
Figure 00000026
т.е. соединение формулы (I-i)
Figure 00000027
где все символы имеют значения, указанные в п.1, или его фармацевтически приемлемая соль.
3. Соединение по п.1, где в соединении формулы (I)
Figure 00000028
т.е. соединение формулы (I-ii)
Figure 00000029
где все символы имеют значения, указанные в п.1, или его фармацевтически приемлемая соль.
4. Соединение по п.1, где в соединении формулы (I)
Figure 00000030
т.е. соединение формулы (I-iii)
Figure 00000031
где все символы имеют значения, указанные в п.1, или его фармацевтически приемлемая соль.
5. Фармацевтическая композиция, включающая соединение формулы (I) или его фармацевтически приемлемую соль, описанные в п.1.
6. Фармацевтическая композиция по п.5, которая является ингибитором цистеинпротеазы.
7. Фармацевтическая композиция по п.5, которая является ингибитором резорбции кости.
8. Ингибитор цистеинпротеазы, включающий соединение формулы (I) или его фармацевтически приемлемую соль, описанные в п.1, в качестве активного ингредиента.
9. Ингибитор по п.8, где цистеинпротеаза представляет собой катепсин К, катепсин S, катепсин L, катепсин В, катепсин Н, катепсин F, катепсин Y, катепсин С, кальпаин или каспазу-1.
10. Ингибитор по п.8, где цистеинпротеаза представляет собой катепсин К.
11. Медицинский состав, включающий соединение формулы (I) или его фармацевтически приемлемую соль, описанные в п.1, вместе с по крайней мере одним компонентом, выбранным из бисфосфоната, стероидного агента, производного витамина К, производного витамина D, ингибитора каспазы-1, производного PTHrP, лиганда PG, ингибитор металлопротеазы, агониста фарнезоидного Х рецептора, агониста эстрогена и агониста прогестерона.
12. Фармацевтическая композиция для лечения и/или профилактики воспалительного заболевания, иммунного заболевания, ишемического заболевания, респираторного заболевания, заболевания циркуляции, заболевания крови, нервного заболевания, заболевания печени или желчного пузыря, заболевания костей или суставов или метаболического заболевания, которая включает соединение формулы (I) или его фармацевтически приемлемую соль, описанную в п.1.
13. Фармацевтическая композиция для лечения и/или профилактики заболевания, включающего апоптоз, заболевания, вызванного разрушением белков, которые составляют организм, или шока, которая включает соединение формулы (I) или его фармацевтически приемлемую соль, описанную в п.1.
14. Композиция для лечения и/или профилактики по п.12, где заболевание костей или суставов представляет собой остеопороз, ревматоидный артрит, артрит, остеоартрит, гипокальцемию, метастаз кости при раке или перелом кости.
15. Способ ингибирования цистеинпротеазы у млекопитающего, при котором млекопитающему вводят эффективное количество соединения формулы (I) или его фармацевтически приемлемой соли по п.1.
16. Способ лечения и/или профилактики воспалительного заболевания, иммунного заболевания, ишемического заболевания, респираторного заболевания, заболевания циркуляции, заболевания крови, нервного заболевания, заболевания печени или желчного пузыря, заболевания костей или суставов или метаболического заболевания у млекопитающего, при котором млекопитающему вводят эффективное количество соединения формулы (I) или его фармацевтически приемлемой соли по п.1.
17. Способ профилактики и/или лечения заболевания, вызванного апоптозом, заболевания, вызванного разрушением белков, которые составляют организм, или шока, при котором млекопитающему вводят эффективное количество соединения формулы (I) или его фармацевтически приемлемой соли по п.1.
18. Способ лечения и/или профилактики по п.16, где заболевания костей или суставов представляют собой остеопороз, ревматоидный артрит, артрит, остеоартрит, гипокальцемию, остеометастазы при раке или перелом кости.
19. Применение соединения или его фармацевтически приемлемой соли по п.1 для получения ингибитора цистеинпротеазы.
20. Применение соединение формулы (I) или его фармацевтически приемлемой соли по п.1 для получения фармацевтического состава для профилактики и/или лечения воспалительного заболевания, иммунного заболевания, ишемического заболевания, респираторного заболевания, заболевания циркуляции, заболевания крови, нервного заболевания, заболевания печени или желчного пузыря, заболевания костей или суставов или метаболического заболевания.
21. Применение соединения формулы (I) или его фармацевтически приемлемой соли по п.1 для получения фармацевтического состава для профилактики и/или лечения заболевания, вызванного апоптозом, заболевания, вызванного разрушением белков, которые составляют организм, или шока.
22. Применение по п.21, где заболевание костей и суставов представляет собой остеопороз, ревматоидный артрит, артрит, остеоартрит, гипокальцемию.
23. Соединение по п.1, описанное в примерах 1-10(66) или его фармацевтически приемлемая соль.
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CA2483998A1 (en) 2003-11-06
US20060111303A1 (en) 2006-05-25
JP3812678B2 (ja) 2006-08-23
PL217947B1 (pl) 2014-09-30
EP1498411A4 (en) 2005-11-30
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WO2003091202A1 (fr) 2003-11-06
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EP1498411A1 (en) 2005-01-19
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JP4826282B2 (ja) 2011-11-30
AU2003235118A1 (en) 2003-11-10
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US8138182B2 (en) 2012-03-20
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