RU2006144863A - Модуляторы андрогеновых рецепторов и способ лечения заболеваний с их помощью - Google Patents

Модуляторы андрогеновых рецепторов и способ лечения заболеваний с их помощью Download PDF

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RU2006144863A
RU2006144863A RU2006144863/04A RU2006144863A RU2006144863A RU 2006144863 A RU2006144863 A RU 2006144863A RU 2006144863/04 A RU2006144863/04 A RU 2006144863/04A RU 2006144863 A RU2006144863 A RU 2006144863A RU 2006144863 A RU2006144863 A RU 2006144863A
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Russia
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azabicyclo
oct
cyanonaphthalen
endo
carbonitrile
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RU2006144863/04A
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Натали ШЛИНГЕР (DK)
Натали ШЛИНГЕР
Ян ПАВЛАС (DK)
Ян ПАВЛАС
Алма ФЕЙЗИЧ (DK)
Алма ФЕЙЗИЧ
Роджер ОЛССОН (SE)
Роджер ОЛССОН
Бригитте Винтер ЛУНД (DK)
Бригитте Винтер ЛУНД
Фабрицио БАДАЛАССИ (DK)
Фабрицио БАДАЛАССИ
Расмус ЛЕВИНСКИ (DK)
Расмус ЛЕВИНСКИ
Миккель Боас ТЮГЕСЕН (DK)
Миккель Боас ТЮГЕСЕН
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Акэдиа Фармасьютикалз Инк. (Us)
Акэдиа Фармасьютикалз Инк.
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Publication of RU2006144863A publication Critical patent/RU2006144863A/ru

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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Claims (20)

1. Соединение, представленное формулой I
Figure 00000001
где R1 и R2 независимо друг от друга выбраны из группы, состоящей из водорода, низшего алкила, алкенила, алкинила, галогена, нитро, циано, гидрокси, амино, низшего аминоалкила, низшего алкокси, арила, гетероарила, COOR4, CONR4R5, NHCOR4, NHSO2R4, OCOR4, COR4, SR4, S(O)nR8, SO2NR8R9;
R3 выбран из группы, состоящей из циано, нитро, S(O)nR8, SO2NR8R9, OSO2R4, P(O)(OR4)(OR5), P(O)(OH)(NR4R5), PO(NR4R5)2, COOR4;
кольцо А представляет собой 5- или 6-членный необязательно ароматический, частично насыщенный или полностью насыщенный карбоцикл или гетероцикл, содержащий до двух гетероатомов или гетерогрупп, выбранных из группы, состоящей из NR6R7, О, SO2, S, С=O и C=S;
кольцо В представляет собой необязательно замещенный моноциклический или бициклический гетероцикл, содержащий до трех гетероатомов или гетерогрупп, выбранных из группы, состоящей из NR6R7, О, SO2, S, С=O и C=S;
Y1 и Y2 представляют собой CR6R7;
R4 и R5 независимо друг от друга выбраны из группы, состоящей из водорода, циано, необязательно замещенного алкила, необязательно замещенного алкенила, необязательно замещенного алкинила, необязательно замещенного циклоалкила, необязательно замещенного гетероциклилалкила, необязательно замещенного арилалкила, необязательно замещенного арила, необязательно замещенного гетероарилалкила, необязательно замещенного гетероарила;
R6 и R7 независимо друг от друга выбраны из группы, состоящей из водорода, галогена, циано, гидрокси, необязательно замещенного алкенила, необязательно замещенного алкинила, необязательно замещенного циклоалкила, необязательно замещенного гетероциклилалкила, необязательно замещенного арилалкила, необязательно замещенного арила, необязательно замещенного гетероарилалкила, необязательно замещенного гетероарила, OR4, NR4R5, SR4, COR4, COOR4, CONR4R5, NHCOR4, OCOR4, CSR4, CSOR4, CSNR4R5, NHCSR4, OCSR4, S(O)nR4, SO2NR4R5, OSO2R4, NHSO2R4;
R8 и R9 независимо друг от друга выбраны из группы, состоящей из водорода, необязательно замещенного алкила, необязательно замещенного алкенила, необязательно замещенного алкинила, необязательно замещенного циклоалкила, необязательно замещенного гетероциклилалкила, необязательно замещенного арилалкила, необязательно замещенного гетероарилалкила; и
n означает целое число от 1 до 3;
либо их фармацевтически приемлемые соли, сложные эфиры, амиды, пролекарственные формы или стереоизомеры.
2. Соединение по п.1, в котором кольцо А представляет собой бензол, циклогексил или пиридин.
3. Соединение по п.1, в котором R3 означает циано, нитро, S(O)nR8 или SO2NR8R9.
4. Соединение по п.1, в котором R3 означает циано или нитро.
5. Соединение по п.1, в котором кольцо В необязательно замещено одной или несколькими группами, выбранными из группы, состоящей из водорода, галогена, гидрокси, необязательно замещенного алкокси, необязательно замещенного алкила, необязательно замещенного алкенила, необязательно замещенного алкинила, необязательно замещенного аминоалкила и NHCOR4.
6. Соединение по п.1, в котором кольцо В необязательно замещено одной или несколькими гидроксигруппами.
7. Соединение по п.1, в котором R6 или R7 означает гидрокси или алкил.
8. Пролекарственная форма - сложный эфир, карбонат, карбамат, сульфат, фосфат или фосфорамидат соединения по п.1.
9. Соединение, выбранное из группы, состоящей из:
4-(3-эндо-гидрокси-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(3-оксо-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-{3-[2-(1Н-имидазол-4-ил)этиламино]-8-азабицикло[3.2.1]окт-8-ил}нафталин-1-карбонитрил, дигидрохлорид,
4-[3-(циклогексилметиламино)-8-азабицикло[3.2.1]окт-8-ил]нафталин-1-карбонитрил, гидрохлорид,
4-[3-(2-морфолин-4-илэтиламино)-8-азабицикло[3.2.1]окт-8-ил]нафталин-1-карбонитрил, дигидрохлорид,
метоксиуксусной кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир,
3-морфолин-4-илпропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, гидрохлорид,
3-(4-этилпиперазин-1-ил)пропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, гидрохлорид,
3-диэтиламинопропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, гидрохлорид,
хлоруксусной кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир,
морфолин-4-илуксусной кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, гидрохлорид,
имидазол-1-илуксусной кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, гидрохлорид,
(4-этилпиперазин-1-ил)уксусной кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, дигидрохлорид,
диэтиламиноуксусной кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, гидрохлорид,
янтарной кислоты эндо-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]овый моноэфир,
трифторуксусной кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир,
4-(эндо-3-метокси-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
N-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]-2-(4-этилпиперазин-1-ил)ацетамид, дигидрохлорид,
4-(3-эндо-гидрокси-3-экзо-метил-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(3-эндо-гидрокси-3-экзо-пропил-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(эндо-спиро[8-азабицикло[3.2.1]октан-3,2'-оксиран]-8-ил)нафталин-1-карбонитрил,
4-(3-экзо-цианометил-3-эндо-гидрокси-8-азабицикло [3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-нитробензойной кислоты экзо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир,
4-(3-экзо-гидрокси-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(3-экзо-метокси-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(8-азабицикло[3.2.1]окт-2-ен-8-ил)нафталин-1-карбонитрил,
4-(8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
3-пирролидин-1-илпропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, фумарат,
3-имидазол-1-илпропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, фумарат,
3-пиразол-1-илпропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, фумарат,
4-(2-метил-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил-фосфат двукислый,
2-экзо-[8-(4-цианонафталин-1-ил)-3-эндо-гидрокси-8-азабицикло[3.2.1]окт-3-ил]-N,N-диметилэтансульфонамид,
4-(3-эндо-гидрокси-3-экзо-метил-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил, гидрохлорид,
4-(3-метил-8-азабицикло[3.2.1]окт-2-ен-8-ил)нафталин-1-карбонитрил,
3-пиперазин-1-илпропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, дигидрохлорид,
3-[бис(2-гидроксиэтил)амино]пропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, фумарат,
3-(3-диметиламинопирролидин-1-ил)пропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, дифумарат,
3-(4-метилпиперазин-1-ил)пропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, дифумарат, и
4-(3-диэтиламинометил-3-гидрокси-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил, гидрохлорид.
10. Соединение, выбранное из группы, состоящей из:
4-(3-эндо-гидрокси-8-азабипикло[3.2,1]окт-8-ил)нафталин-1-карбонитрил,
3-(4-этилпиперазин-1-ил)пропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, гидрохлорид,
3-диэтиламинопропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир, гидрохлорид,
4-(3-эндо-гидрокси-3-экзо-метил-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(3-эндо-гидрокси-3-экзо-пропил-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(эндо-спиро[8-азабицикло[3.2.1]октан-3,2'-оксиран]-8-ил)нафталин-1-карбонитрил,
4-(8-азабицикло[3.2.1]окт-2-ен-8-ил)нафталин-1-карбонитрил,
4-(8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(2-метил-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(3-эндо-гидрокси-3-экзо-метил-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил, гидрохлорид, и
4-(3-метил-8-азабицикло[3.2.1]окт-2-ен-8-ил)нафталин-1-карбонитрил.
11. Соединение, выбранное из группы, состоящей из:
4-(3-пропиламино-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил, гидрохлорид,
4-(3-диметиламино-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил, гидрохлорид,
4-[3-(3-гидроксипропиламино-8-азабицикло[3.2.1]окт-8-ил]нафталин-1-карбонитрил, гидрохлорид,
4-[3-(2-этоксиэтиламино-8-азабицикло[3.2.1]окт-8-ил]нафталин-1-карбонитрил, гидрохлорид,
4-(3-циклопропиламино-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил, гидрохлорид,
4-[3-(2-диметиламиноэтиламино)-8-азабицикло[3.2.1]окт-8-ил]нафталин-1-карбонитрил, дигидрохлорид,
4-{3-[(фуран-2-илметил)амино]-8-азабицикло[3.2.1]окт-8-ил}нафталин-1-карбонитрил,гидрохлорид,
4-{3-[(пиридин-2-илметил)амино]-8-азабицикло[3.2.1]окт-8-ил}нафталин-1-карбонитрил, дигидрохлорид,
4-[3-(2-изопропоксиэтиламино)-8-азабицикло[3.2.1]окт-8-ил]нафталин-1-карбонитрил, гидрохлорид,
4-(3-гидроксиимино-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
3-хлорпропионовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир,
4-(3-экзо-этинил-3-эндо-гидрокси-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-[3-(2-[1,3]диоксан-2-илэтил)-3-гидрокси-8-азабицикло[3.2.1]окт-8-ил] нафталин-1-карбонитрил,
4-(3-амино-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил, гидрохлорид,
2-хлор-N-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]ацетамид, гидрохлорид,
N-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]-2-(4-этилпиперазин-1 -ил)ацетамид, дигидрохлорид,
2-цианоэтил-эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил-N,N-диизопропиламидофосфат,
эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил-N,N-диизопропил-амидофосфат кислый,
[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]мочевина,
диметилкарбаминовой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло-[3.2.1]окт-3-иловый эфир,
4-[экзо-(4-этилпиперазин-1-илметил)-3-эндо-гидрокси-8-азабицикло [3.2.1]окт-8-ил]нафталин-1-карбонитрил,
4-(3-эндо-гидрокси-3-экзо-гидроксиметил-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(3-эндо-гидрокси-3-экзо-{[2-(1Н-имидазол-4-ил)этиламино]метил}-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(3-эндо-гидрокси-3-экзо-метоксиметил-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
акриловой кислоты эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-иловый эфир,
4-(2-метил-3-оксо-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
4-(3-экзо-бензил-3-эндо-гидрокси-8-азабицикло[3.2.1]окт-8-ил)нафталин-1-карбонитрил,
8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-2-ен-2-карбоновой кислоты метиловый эфир,
8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]октан-2-карбоновой кислоты метиловый эфир,
4-(2-гидроксиметил-8-азабицикло[3.2.1]окт-2-ен-8-ил)нафталин-1-карбонитрил,
(1R,2R,3S,5S)-3-бензоилокси-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]октан-2-карбоновой кислоты метиловый эфир,
(1R,2R,3S,5S)-4-(3-гидрокси-2-гадроксиметил-8-азабицикло[3.2.1]окт-8-ил)-нафталин-1-карбонитрил,
2-цианоэтил-эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил-N,N-диизопропиламидофосфит,
2-цианоэтил-эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил-диизопропиламидофосфат,
2-цианоэтил-этил-эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил-фосфат,
этил-эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил-фосфат кислый,
бис(2-цианоэтил)-эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил-фосфат,
2-цианоэтил-эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил-фенилфосфат,
эндо-8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил-фенилфосфат кислый,
N-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]ацетамид,
3-хлор-N-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]пропанамид,
N-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]-3-(4-этилпиперазин-1-ил)пропанамид, дигидрохлорид,
N-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]-3-диэтиламино-пропионамид, гидрохлорид,
N-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]-3-(1Н-имидазол-1-ил)пропанамид, гидрохлорид,
N-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]-2-(этоксиэтокси)-ацетамид,
N'-[8-(4-цианонафталин-1-ил)-8-азабицикло[3.2.1]окт-3-ил]-4-метилбензол-сульфонилгидразон и
3-экзо-[8-(4-цианонафталин-1-ил)-3-эндо-гидрокси-8-азабицикло[3.2.1]окт-3-ил]-N,N-диметилпропанамид.
12. Способ активирования андрогеновых рецепторов, включающий контактирование данных рецепторов с соединением по п.1.
13. Способ облегчения симптомов гипогонадизма, включающий идентифицирование нуждающегося в этом пациента и введение данному пациенту соединения по п.1.
14. Способ лечения заболевания или облегчения его симптомов, включающий идентифицирование нуждающегося в этом пациента и введение данному пациенту соединения по п.1;
где заболевание выбрано из группы, состоящей из пониженного уровня тестостерона в плазме крови, бесплодия у мужчин, сперматогенеза у мужчин, расстройства эрекции у мужчин, андропаузы у мужчин, эндометриоза у женщин, диспарейнии у женщин, вагинизма у женщин, расстройства полового возбуждения у женщин, расстройства сексуального оргазма у женщин, нарушения либидо у мужчин, кахексии, истощения при ВИЧ-инфекции, критических болезней, при которых наблюдается мышечное истощение; саркопении; хрупкости; малого роста; карликовости; падения плотности костной ткани; расстройства настроения, в том числе плохого самочувствия, упадка сил, гнева, раздражительности, грусти, усталости и нервозности; депрессии; нарушений познавательной способности, в том числе беглости речи и пространственной памяти; нейродегенеративных заболеваний, в том числе болезни Альцгеймера, слабого нарушения познавательной способности (MCI), деменции тельца Льюиса и фронтотемпоральной деменции; ксерофтальмии; метаболических нарушений, в том числе дислипидемии, атеросклероза и независимого от инсулина диабета (NIDDM); сердечно-сосудистых нарушений, в том числе, но не ограничиваясь этим, гипертензии, заболеваний коронарной артерии и перфузии миокарда; ожирения; анемии; рака простаты и шизофрении.
15. Способ гормональной заместительной терапии, включающий идентифицирование нуждающегося в этом пациента и введение этому пациенту соединения по п.1.
16. Способ по п.15, в котором необходимость в гормональной заместительной терапии вызвана орхидэктомией, проведенной хирургическим или химическим способом.
17. Способ увеличения мышечной силы при заболеваниях, в том числе мышечной дистрофии, миотонической дистрофии, астме при лечении глюкокортикоидами, включающий идентифицирование нуждающегося в этом пациента и введение этому пациенту соединения по п.1.
18. Способ профилактики заболевания, выбранного из группы, состоящей из падения плотности костной ткани; ксерофтальмии; метаболических нарушений, в том числе дислипидемии, атеросклероза и независимого от инсулина диабета (NIDDM); сердечно-сосудистых нарушений, в том числе гипертензии, заболеваний коронарной артерии и перфузии миокарда; ожирения и рака простаты, включающий введение пациенту соединения по п.1.
19. Способ улучшения связанных со здоровьем параметров качества жизни, выбранных из группы, состоящей из выживаемости, ущербности, функционального статуса восприятия состояния здоровья и перспектив, включающий введение пациенту соединения по п.1.
20. Способ замедления развития рака простаты, включающий введение пациенту соединения по п.1.
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