RU2006112428A - Производные 2-пиридона в качестве ингибиторов эластазы нейтрофилов и их применение - Google Patents
Производные 2-пиридона в качестве ингибиторов эластазы нейтрофилов и их применение Download PDFInfo
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Claims (10)
1. Соединение формулы (I)
где Y представляет собой CR3 или N;
R1 представляет собой Н или С1-6алкил;
R2 представляет собой фенил или пяти- или шестичленное гетероароматическое кольцо, содержащее от 1 до 4 гетероатомов, независимо выбранных из О, S и N; где указанное ароматическое кольцо возможно замещено 1-3 заместителями, выбранными независимо из ОН, галогена, C1-6алкила, С1-6алкокси, NR58COR50, COOR51, COR52, CONR53R54 и NR47R48; где указанный алкил возможно дополнительно замещен ОН, C1-6алкокси, CN или CO2R49;
R47 и R48 независимо представляют собой Н, С1-6алкил или С2-6алканоил;
R3 представляет собой Н или F;
G1 представляет собой фенил или пяти- или шестичленное гетероароматическое кольцо, содержащее от 1 до 3 гетероатомов, независимо выбранных из О, S и N;
R5 представляет собой Н, галоген, C1-6алкил, CN, С1-6алкокси, NO2, NR14R15, C1-3алкил, замещенный одним или более чем одним атомом F, или C1-3алкокси, замещенный одним или более чем одним атомом F;
R14 и R15 независимо представляют собой Н или С1-3алкил; где указанный алкил возможно дополнительно замещен одним или более чем одним атомом F;
n представляет собой целое число 1, 2 или 3 и, когда n представляет собой 2 или 3, каждая группа R5 выбрана независимо;
R4 представляет собой Н или С1-6алкил; где указанный алкил возможно дополнительно замещен ОН или С1-6алкокси;
либо R4 и L соединены вместе так, что группа -NR4L- представляет собой 5-7-членное азациклическое кольцо, возможно включающее один дополнительный гетероатом, выбранный из О, S и NR16;
L представляет собой связь, О, S(O)p, NR29 или С1-6алкил; где указанный алкил возможно включает гетероатом, выбранный из О, S и NR16; и указанный алкил возможно дополнительно замещен ОН или ОМе;
G2 представляет собой моноциклическую кольцевую систему, выбранную из
1) фенила или фенокси,
2) 5- или 6-членного гетероароматического кольца, содержащего от одного до трех гетероатомов, независимо выбранных из О, S и N,
3) С3-6 насыщенного или частично ненасыщенного циклоалкила или
4) С4-7 насыщенного или частично ненасыщенного гетероциклического кольца, содержащего один или два гетероатома, независимо выбранные из О, S(O)p и NR17, и, возможно, дополнительно включающего карбонильную группу; или
G2 представляет собой бициклическую кольцевую систему, в которой каждое из двух колец независимо выбрано из
1) фенила,
2) 5- или 6-членного гетероароматического кольца, содержащего от одного до трех гетероатомов, независимо выбранных из О, S и N,
3) С3-6 насыщенного или частично ненасыщенного циклоалкила или
4) С4-7 насыщенного или частично ненасыщенного гетероциклического кольца, содержащего один или два гетероатома, независимо выбранные из О, S(O)p и NR17, и, возможно, дополнительно включающего карбонильную группу;
и эти два кольца либо конденсированы вместе, либо связаны вместе прямой связью, либо разделены линкерной группой, выбранной из О, S(O)q или CH2,
где указанная моноциклическая или бициклическая кольцевая система возможно дополнительно замещена заместителями в количестве от одного до трех, независимо выбранными из CN, ОН, С1-6алкила, С1-6алкокси, галогена, NR18R19, NO2, OSO2R38, CO2R20, C(=NH)NH2, C(O)NR21R22, C(S)NR23R24, SC(=NH)NH2, NR31C(=NH)NH2, S(O)sR25, SO2NR26R27, C1-3алкокси, замещенного одним или более чем одним атомом F, и C1-3алкила, замещенного SO2R39, NR56R57 или одним или более чем одним атомом F; или
когда L не представляет собой связь, G2 может также представлять собой Н;
в каждом случае p, q, s и t независимо представляют собой целое число 0, 1 или 2;
R18 и R19 независимо представляют собой Н, С1-6алкил, формил, C2-6алканоил, S(O)tR32 или SO2R33R34; где указанная алкильная группа возможно дополнительно замещена галогеном, CN, С1-4алкокси или CONR31R42;
R25 представляет собой Н, С1-6алкил или С3-6циклоалкил; где указанная алкильная группа возможно дополнительно замещена одним или более чем одним заместителем, выбранным независимо из ОН, CN, CONR35R36, CO2R37, OCOR40, С3-6циклоалкила, С4-7 насыщенного гетероциклического кольца, содержащего один или два гетероатома, независимо выбранные из О, S(O)p и NR43, и фенила или 5- или 6-членного гетероароматического кольца, содержащего от одного до трех гетероатомов, независимо выбранных из О, S и N; где указанное ароматическое кольцо возможно дополнительно замещено одним или более чем одним заместителем, выбранным независимо из галогена, CN, С1-4алкила, С1-4алкокси, ОН, CONR44R45, CO2R46, S(O)sR55 и NHCOCH3;
R32 представляет собой Н, С1-6алкил или С3-6циклоалкил;
R16, R17, R20, R21, R22, R23, R24, R26, R27, R29, R31, R33, R34, R35, R36, R37, R38, R39, R40, R41, R42, R43, R44, R45, R46, R49, R50, R51, R52, R53, R54, R55, R56, R57 и R58 независимо представляют собой Н или C1-6алкил;
и его фармацевтически приемлемые соли.
2. Соединение формулы (I) по п.1, где Y представляет собой CR3.
3. Соединение формулы (I) по п.1, где G1 представляет собой фенил.
4. Соединение формулы (I) по п.1, где R5 представляет собой Cl, СН3, CN или CF3.
5. Соединение формулы (I) по п.1 или его фармацевтически приемлемая соль для применения в качестве лекарства.
6. Фармацевтическая композиция, содержащая соединение формулы (I), как оно определено в любом из пп.1-4, или его фармацевтически приемлемую соль, возможно в смеси с фармацевтически приемлемым разбавителем или носителем.
7. Способ лечения или снижения риска заболевания или состояния человека, при котором благоприятно ингибирование активности эластазы нейтрофилов, при котором субъекту, страдающему таким заболеванием или состоянием или склонному к нему, вводят терапевтически эффективное количество соединения формулы (I), как оно определено в любом из пп.1-4, или его фармацевтически приемлемой соли.
8. Применение соединения формулы (I), как оно определено в любом из пп.1-4, или его фармацевтически приемлемой соли в производстве лекарства для лечения или профилактики заболеваний или состояний человека, при которых благоприятно ингибирование активности эластазы нейтрофилов.
9. Применение соединения формулы (I), как оно определено в любом из пп.1-4, или его фармацевтически приемлемой соли в производстве лекарства для лечения или профилактики воспалительных заболеваний или состояний.
10. Способ получения соединения формулы (I), как оно определено в любом из пп.1-4, и его оптических изомеров, рацематов и таутомеров, а также фармацевтически приемлемых солей, при котором
а) подвергают взаимодействию соединение формулы (II)
где R1, R4, R5, Y, G1, G2, L и n являются такими, как определено в формуле (I), и Hal представляет собой атом галогена, предпочтительно бромо или йодо;
с нуклеофилом R2-M, где R2 является таким, как определено в формуле (I), a M представляет собой группу оловоорганической или борорганической кислоты; либо
б) когда R2 представляет собой кольцо 1,3,4-оксадиазол-2-ил или 1,3,4-тиадиазол-2-ил, подвергают взаимодействию соединение формулы (III)
где R1, R4, R5, Y, G1, G2, L и n являются такими, как определено в формуле (I), Z представляет собой О или S, и Х представляет собой C1-6алкил или NR47R48, a R47 и R48 являются такими, как определено в формуле (I); с подходящим дегидратирующим агентом, таким как фосфорилхлорид или триметилсилилполифосфат; либо
в) подвергают взаимодействию соединение формулы (XV)
где R1, R2, R5, n, G1 и Y являются такими, как определено в формуле (I), a L1 представляет собой уходящую группу,
с соединением формулы (IX) или его солью
где R4, G2 и L являются такими, как определено в формуле (I);
и, где желательно или необходимо, превращают полученное в результате соединение формулы (I) или другую его соль в его фармацевтически приемлемую соль; или превращают одно соединение формулы (I) в другое соединение формулы (I); и, где желательно, превращают полученное в результате соединение формулы (I) в его оптический изомер.
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CN101481352A (zh) * | 2008-01-10 | 2009-07-15 | 上海恒瑞医药有限公司 | 双环取代吡唑酮偶氮类衍生物、其制备方法及其在医药上的应用 |
TW201036957A (en) * | 2009-02-20 | 2010-10-16 | Astrazeneca Ab | Novel salt 628 |
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