RU2011143740A - Соединение пиримидина - Google Patents

Соединение пиримидина Download PDF

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Publication number
RU2011143740A
RU2011143740A RU2011143740/04A RU2011143740A RU2011143740A RU 2011143740 A RU2011143740 A RU 2011143740A RU 2011143740/04 A RU2011143740/04 A RU 2011143740/04A RU 2011143740 A RU2011143740 A RU 2011143740A RU 2011143740 A RU2011143740 A RU 2011143740A
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RU
Russia
Prior art keywords
lower alkyl
alkylene
halogen
cycloalkyl
lower alkylene
Prior art date
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RU2011143740/04A
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English (en)
Inventor
Юдзи МАЦУСИМА
Хироказу КУБОТА
Хисао ХАМАГУТИ
Есинори ОКАМОТО
Такеси ХОНДО
Фусако НИСИГАКИ
Original Assignee
Астеллас Фарма Инк.
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Application filed by Астеллас Фарма Инк. filed Critical Астеллас Фарма Инк.
Publication of RU2011143740A publication Critical patent/RU2011143740A/ru

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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Abstract

1. Соединение формулы (I) или его сольгде Rнизший алкил, Сциклоалкил, -О-низший алкил, галоген-низший алкил, низший алкилен-Сциклоалкил или низший алкилен-О-низший алкил;R-С(О)R, -С(О)NRR, низший алкилен-R, низший алкилен-NRR, низший алкилен-NRC(О)R, низший алкилен-OR, -NRC(О)R, -NRC(О)OR, -NRC(О)NRR, -NRS(О)Rили -NRS(О)NRR;W -СН-, -NR-, -О- или -S(O)-;RСалкил; Салкенил; Салкинил; галоген-Салкил; Салкил, замещенный 1-5 группами, выбранными из группы G; R; -Салкилен-R; -Салкилен-О-R; -Салкилен-О-низший алкилен-R; -Салкилен-S(О)-R; -Х-С(R)(фенил)или -СН(фенил)-СН(ОН)-фенил;где Салкилен может содержать от 1 до 5 заместителей, выбранных из группы G;или W и R, объединенные друг с другом, представляют собойилиRодинаковые или отличаются друг от друга, при этом каждый представляет собой Н или низший алкил;Rазотсодержащая насыщенная гетероциклическая группа, которая может содержать от 1 до 5 заместителей, выбранных из группы G;Rнизший алкил, галоген-низший алкил, низший алкилен-OR, низший алкилен-О-низший алкилен-OR, низший алкилен-О-галоген-низший алкил или -Х-Сциклоалкил, низший алкилен-О-Сциклоалкил, -Х-Сциклоалкенил, низший алкилен-О-Сциклоалкенил, -Х-арил, низший алкилен-О-Х-арил, низший алкилен-S(О)-арил, -Х-гетероциклическая группа, низший алкилен-О-Х-гетероциклическая группа или низший алкилен-S(О)- гетероциклическая группа, каждый из которых может содержать от 1 до 5 заместителей, выбранных из группы Gв цикле;RН, низший алкил или низший алкилен-OR,RСциклоалкил, Сциклоалкенил, арил или гетероциклическая группа;где Rможет содержать от 1 до 5 заместителей, выбранных из группы G;Rодинаковые или отличаются друг от друга, при этом каждый представляет собой низший алкил, галоген, -О-низший алкил, галоген-ни�

Claims (15)

1. Соединение формулы (I) или его соль
Figure 00000001
где R1 низший алкил, С3-6 циклоалкил, -О-низший алкил, галоген-низший алкил, низший алкилен-С3-6 циклоалкил или низший алкилен-О-низший алкил;
R2 -С(О)R20, -С(О)NR21R22, низший алкилен-R20, низший алкилен-NR21R22, низший алкилен-NR0C(О)R21, низший алкилен-OR21, -NR0C(О)R21, -NR0C(О)OR21, -NR0C(О)NR21R22, -NR0S(О)2R21 или -NR0S(О)2NR21R22;
W -СН2-, -NR0-, -О- или -S(O)m-;
R3 С3-10 алкил; С2-6 алкенил; С2-6 алкинил; галоген-С3-6 алкил; С1-10 алкил, замещенный 1-5 группами, выбранными из группы G1; R30; -С1-10 алкилен-R30; -С1-10 алкилен-О-R30; -С1-10 алкилен-О-низший алкилен-R30; -С1-10 алкилен-S(О)2-R30; -Х-С(R0)(фенил)2 или -СН(фенил)-СН(ОН)-фенил;
где С1-10 алкилен может содержать от 1 до 5 заместителей, выбранных из группы G1;
или W и R3, объединенные друг с другом, представляют собой
Figure 00000002
или
Figure 00000003
R0 одинаковые или отличаются друг от друга, при этом каждый представляет собой Н или низший алкил;
R20 азотсодержащая насыщенная гетероциклическая группа, которая может содержать от 1 до 5 заместителей, выбранных из группы G2;
R21 низший алкил, галоген-низший алкил, низший алкилен-OR0, низший алкилен-О-низший алкилен-OR0, низший алкилен-О-галоген-низший алкил или -Х-С3-10 циклоалкил, низший алкилен-О-С3-10 циклоалкил, -Х-С3-10 циклоалкенил, низший алкилен-О-С3-10 циклоалкенил, -Х-арил, низший алкилен-О-Х-арил, низший алкилен-S(О)m-арил, -Х-гетероциклическая группа, низший алкилен-О-Х-гетероциклическая группа или низший алкилен-S(О)m- гетероциклическая группа, каждый из которых может содержать от 1 до 5 заместителей, выбранных из группы G3 в цикле;
R22 Н, низший алкил или низший алкилен-OR0,
R30 С3-10 циклоалкил, С5-10 циклоалкенил, арил или гетероциклическая группа;
где R30 может содержать от 1 до 5 заместителей, выбранных из группы G3;
R31 одинаковые или отличаются друг от друга, при этом каждый представляет собой низший алкил, галоген, -О-низший алкил, галоген-низший алкил, -С(О)OR0 или нитро;
Группа G1: галоген, -С(О)OR0, -С(О)N(R0)2, -CN, -OR0, -О- низший алкилен-OR0, -О-галоген-низший алкил, -N(R0)2, -N(R0)-фенил, -N(низший алкилен-OR0)2, -NHC(O)-низший алкил, -N(R0)С(О)N(R0)2, -S(O)m-низший алкил и -S(O)2N(R0)2;
Группа G2: низший алкил, галоген, галоген-низший алкил, -С(О)OR0, -С(О)N(R0)2, -CN, -Х-OR0, -О-низший алкилен-OR0, -О-галоген-низший алкил, -ОС(О)-низший алкил, -Х-N(R0)2, оксо, -Х- С3-6 циклоалкил, -Х-О-Х-С3-6 циклоалкил, -Х-фенил и -Х-морфолинил;
Группа G3: низший алкил, С2-6 алкенил, С2-6 алкинил, галоген, галоген-низший алкил, -Х-С(О)OR0, -Х-С(О)N(R0)2, -CN, -Х-С(О)R0, -Х-OR0, -О-низший алкилен-О-R0, -О-галоген-низший алкил, -ОС(О)-низший алкил, -Х-N(R0)2, -Х-S(O)m-низший алкил, оксо, -Х-С3-10 циклоалкил, -Х-О-Х-С3-10 циклоалкил, -Х-арил, -Х-С(О)-арил, -Х-О-Х-арил, -Х-S(O)m-арил, -Х-гетероциклическая группа, -Х-О-Х-гетероциклическая группа, -Х-S(O)m-гетероциклическая группа и -О-СН2СН2-О-, связанная с одним и тем же атомом углерода;
где арил и гетероциклическая группа могут быть замещены низшим алкилом, галогеном, галоген-низшим алкилом, -О-низшим алкилом или оксо;
D: связь или -С(R31)2-;
Е: связь, -[C(R31)2]1-3- или -О-С(R31)2-;
где О связан с бензольным кольцом;
Х - одинаковые или отличаются друг от друга, при этом каждый представляет собой связь или низший алкилен;
m - одинаковые или отличаются друг от друга, при этом каждый равен 0, 1 или 2;
n - одинаковые или отличаются друг от друга, при этом каждый равен 0, 1 или 2;
при условии, что
(1) в случае, когда R2 представляет собой -С(О)R20, R1 представляет собой группу, отличающуюся от метила, и -W-R3 представляет собой группу, отличающуюся от -NH-фенила, который может быть замещен;
(2) в случае, когда R2 представляет собой -С(О)NR21R22, R3 представляет собой С5-10 циклоалкил или низший алкилен-С5-10 циклоалкил, и С5-10 циклоалкил может содержать от 1 до 5 заместителей, выбранных из группы G3;
(3) в случае, когда R2 представляет собой низший алкилен-R20 или низший алкилен-NR21R22, и W представляет собой -СН2-, -NR0-, -О- или -S(O)m-, R3 представляет собой С7-10 циклоалкил или низший алкилен-С7-10 циклоалкил, и С7-10 циклоалкил может содержать от 1 до 5 заместителей, выбранных из группы G3;
(4) в случае, когда R2 представляет собой низший алкилен-NR0C(О)R21, R1 представляет собой группу, отличающуюся от метила;
(5) в случае, когда R2 представляет собой -NR0C(О)R21, -NR0C(О)OR21, -NR0C(О)NR21R22, -NR0S(O)2R21 или -NR0S(O)2NR21R22, R1 представляет собой группу, отличающуюся от метила, и -W-R3 представляет собой группу, отличающуюся от -СН2-1Н-пиразол-1-ила, который может быть замещен, и -СН2-1Н-1,2,4-триазол-1-ила, который может быть замещен; и
следующие соединения исключаются:
2-(циклогексиламино)-N-(3,5-дихлорфенил)-4-(трифторметил)пиримидин-5-карбоксамид;
2-(циклогексиламино)-N,N-диэтил-4-изопропилпиримидин-5-карбоксамид;
N-циклогексил-2-(циклогексиламино)-4-метилпиримидин-5-карбоксамид;
трет-бутил({2-[(3-хлор-4-фторфенил)амино]-4-(трифторметил)-5-пиримидинил}метил)(циклопропилметил)карбамат,
1-{[5-(метоксиметил)-4-(трифторметил)-2-пиримидинил]амино}-3-метил-1Н-пиррол-2,5-дион,
1-{[4-этил-5-(метоксиметил)-2-пиримидинил](метил)амино}-3-метил-1Н-пиррол-2,5-дион,
N-бутил-5-(феноксиметил)-4-(трифторметил)пиримидин-2-амин,
2-хлор-5-гидрокси-N-[2-[[4-[2-(1-пирролидинил)этокси]фенил]амино]-4-(трифторметил)-5-пиримидинил]бензамид,
N-{4-метокси-2-[2-(пропиламино)этокси]-5-пиримидинил}-4-(трифторметокси)бензолсульфонамид и
N-{4-метокси-2-[2-(пропиламино)этокси]-5-пиримидинил}-4-изопропилбензолсульфонамид].
2. Соединение или его соль по п.1, где R1 представляет собой низший алкил, С3-6 циклоалкил или галоген-низший алкил, R2 представляет собой -С(О)R20, W представляет собой -NH-, и R3 представляет собой С7-10 циклоалкил, который может содержать от 1 до 5 заместителей, выбранных из низшего алкила, галогена и ОН.
3. Соединение или его соль по п.2, где R1 представляет собой низший алкил или С3-6 циклоалкил.
4. Соединение или его соль по п.2, где R1 представляет собой галоген-низший алкил.
5. Соединение или его соль по п.2, где R20 представляет собой 1-пирролидил, 1-пиперидил, морфолин-4-ил, тиоморфолин-4-ил или 1,1-диоксидотиоморфолин-4-ил, которые могут содержать от 1 до 5 заместителей, выбранных из низшего алкила и галогена.
6. Соединение или его соль по п.5, где R20 представляет собой морфолин-4-ил или 1,1-диоксидотиоморфолин-4-ил.
7. Соединение или его соль по п.6, где R3 представляет собой С7-10 циклоалкил, который может содержать от 1 до 5 заместителей, выбранных из низшего алкила, галогена и ОН на кольце, и имеет мостик.
8. Соединение или его соль по п.1, которое выбирают из группы, включающей:
N-адамантан-1-ил-5-[(4,4-дифторпиперидин-1-ил)карбонил]-4-(трифторметил)пиримидин-2-амин,
1-{5-[(1,1-диоксидотиоморфолин-4-ил)карбонил]-4-(трифторметил)пиримидин-2-ил}-4,4-диметил-1,2,3,4-тетрагидрохинолин,
рац-N-[(1R,2R,4S)-бицикло[2.2.1]гепт-2-ил]-4-изопропил-5-(морфолин-4-илкарбонил)пиримидин-2-амин,
рац-N-[(1R,2R,4S)-бицикло[2.2.1]гепт-2-ил]-4-циклопропил-5-[(1,1-диоксидотиоморфолин-4-ил)карбонил]пиримидин-2-амин,
рац-N-[(1R,2R,4S)-бицикло[2.2.1]гепт-2-ил]-4-трет-бутил-5-(морфолин-4-илкарбонил)пиримидин-2-амин,
N-[(1S,2S,4R)-бицикло[2.2.1]гепт-2-ил]-4-изопропил-5-(морфолин-4-илкарбонил)пиримидин-2-амин,
N-[(1R,2R,4S)-бицикло[2.2.1]гепт-2-ил]-4-изопропил-5-(морфолин-4-илкарбонил)пиримидин-2-амин,
3-({5-[(3,3,4,4-тетрафторпирролидин-1-ил)карбонил]-4-(трифторметил)пиримидин-2-ил}амино)адамантан-1-ол,
рац-N-[(1R,2R,4S)-бицикло[2.2.1]гепт-2-ил]-5-[(1,1-диоксидотиоморфолин-4-ил)карбонил]-4-(трифторметил)пиримидин-2-амин,
5-[(1,1-диоксидотиоморфолин-4-ил)карбонил]-4-(трифторметил)-N-[(1R,2S,4R)-1,7,7-триметилбицикло[2.2.1]гепт-2-ил]пиримидин-2-амин,
5-[(1,1-диоксидотиоморфолин-4-ил)карбонил]-N-(3,5,7-трифторадамантан-1-ил)-4-(трифторметил)пиримидин-2-амин,
N-[(1R,2R,4S)-бицикло[2.2.1]гепт-2-ил]-5-[(1,1-диоксидотиоморфолин-4-ил)карбонил]-4-(трифторметил)пиримидин-2-амин,
N-[(1S,2S,4R)-бицикло[2.2.1]гепт-2-ил]-5-[(1,1-диоксидотиоморфолин-4-ил)карбонил]-4-(трифторметил)пиримидин-2-амин,
N-бицикло[2.2.2]окт-1-ил-5-[(1,1-диоксидотиоморфолин-4-ил)карбонил]-4-(трифторметил)пиримидин-2-амин,
N-адамантан-1-ил-5-(морфолин-4-илкарбонил)-4-(трифторметил)пиримидин-2-амин,
рац-N-[(1R,2R,4S)-бицикло[2.2.1]гепт-2-ил]-5-[(4,4-дифторпиперидин-1-ил)метил]-4-(трифторметил)пиримидин-2-амин и
N-адамантан-1-ил-5-[(1,1-диоксидотиоморфолин-4-ил)метил]-4-(трифторметил)пиримидин-2-амин.
9. Фармацевтическая композиция, содержащая соединение или его соль по п.1, и фармацевтически приемлемый эксципиент.
10. Фармацевтическая композиция для предупреждения или лечения заболевания, связанного с каннабиноидным рецептором 2 типа, содержащая соединение или его соль по п.1.
11. Фармацевтическая композиция по п.10, где заболевание, связанное с каннабиноидным рецептором 2 типа, представляет собой воспалительное заболевание.
12. Фармацевтическая композиция по п.10, где заболевание, связанное с каннабиноидным рецептором 2 типа, представляет собой боль.
13. Применение соединения или его соли по п.1 для получения фармацевтической композиции для предупреждения или лечения заболевания, связанного с каннабиноидным рецептором 2 типа.
14. Применение соединения или его соли по п.1 для предупреждения или лечения заболевания, связанного с каннабиноидным рецептором 2 типа.
15. Способ предупреждения или лечения заболевания, связанного с каннабиноидным рецептором 2 типа, включающий введение пациенту эффективного количества соединения по п.1 или его фармацевтически приемлемой соли.
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