RU2004117531A - Использование производных 2-амино-4-пиридилметилтиазолина в качестве ингибиторов индуцибельной no-синтазы - Google Patents

Использование производных 2-амино-4-пиридилметилтиазолина в качестве ингибиторов индуцибельной no-синтазы Download PDF

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RU2004117531A
RU2004117531A RU2004117531/04A RU2004117531A RU2004117531A RU 2004117531 A RU2004117531 A RU 2004117531A RU 2004117531/04 A RU2004117531/04 A RU 2004117531/04A RU 2004117531 A RU2004117531 A RU 2004117531A RU 2004117531 A RU2004117531 A RU 2004117531A
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formula
compound
ylmethyl
tert
compounds
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Эрик БАК (FR)
Эрик Бак
Антони БИГО (FR)
Антони Биго
Жан-Кристоф КАРРИ (FR)
Жан-Кристоф Карри
Серж МИНЬЯНИ (FR)
Серж Миньяни
Батист РОНАН (FR)
Батист Ронан
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Мишель Табар
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Авентис Фарма С.А. (Fr)
Авентис Фарма С.А.
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Claims (18)

1. Соединение формулы (I)
Figure 00000001
где R1 и R2 либо идентичны и представляют собой гидроксильные радикалы, (C1-C4) алкил, атом хлора или (C1-C4) алкоксильный радикал, либо, по меньшей мере, один из R1 или R2 представляет атом водорода, а другой представляет радикал (C1-C4) алкил, (C1-C4) алкокси, гидрокси или атом хлора, где (C1-C4) алкильный и (C1-C4) алкоксильный радикалы содержат от 1 до 4 атомов углерода в линейной или разветвленной цепи,
его рацемические смеси, энантиомеры, диастереоизомеры и их смеси, его таутомеры, а также их фармацевтически приемлемые соли.
2. Соединение по п.1, где соединение формулы (I) является одним из следующих соединений:
4-(2-гидроксипиридин-4-илметил)-4,5-дигидротиазол-2-иламин,
4-(2-хлорпиридин-4-илметил)-4,5-дигидро-1,3-тиазол-2-иламин,
4-(2,6-дихлорпиридин-4-илметил)-4,5-дигидро-1,3-тиазол-2-иламин,
их рацемические смеси, энантиомеры, диастереоизомеры и их смеси, их таутомеры, а также их фармацевтически приемлемые соли.
3. Соединение по пп.1–2, где соединение формулы (I) является одним из следующих соединений:
(+)-4-(2-гидроксипиридин-4-илметил)-4,5-дигидротиазол-2-иламин,
4-(2-хлорпиридин-4-илметил)-4,5-дигидро-1,3-тиазол-2-иламин,
4-(2,6-дихлорпиридин-4-илметил)-4,5-дигидро-1,3-тиазол-2-иламин,
их таутомеры, а также их фармацевтически приемлемые соли.
4. Соединение по пп.1-3 для применения в качестве лекарственного препарата.
5. Фармацевтическая композиция, содержащая соединение по п.п. 1–3 в фармацевтически приемлемой среде.
6. Лекарственный препарат по п.4, который содержит, по меньшей мере, одно соединение по пп.1–3, предназначенный для терапевтического применения при лечении заболеваний, при которых происходит аномальное образование оксида азота (NO) в результате индукции индуцибельной NO-синтазы (NOS-2).
7. Лекарственный препарат по п.4, который содержит, по меньшей мере, одно соединение по пп.1–3, предназначенный для терапевтического применения при лечении болезни Паркинсона.
8. Способ получения соединений формулы (I), определенных в п.1, включающий стадию циклизации производного формулы
Figure 00000002
где R1 и R2 имеют те же значения, что и в п.1, и, необязательно, преобразования его в фармацевтически приемлемую соль.
9. Способ получения по п.8, в котором циклизацию проводят в кислой среде при температуре около 100°С.
10. Способ получения по п.9, в котором в качестве кислой среды предпочтительно используют 6 н. соляную кислоту.
11. Способ получения соединений формулы (II), определенных в п.8, в которых R1 и R2 имеют то же значение, что и в п.1, включающий стадию взаимодействия соединения формулы (IIa)
Figure 00000003
где Ra либо атом водорода, либо защитная группа аминной функции, например, CO2-трет-Bu или Ac; и
Rb - либо (C1-C4) алкильный радикал, либо алкоксикарбонильный радикал,
с восстановителем для получения соединения формулы (IIb)
Figure 00000004
которое подвергают воздействию вещества, снимающего защитные группы для получения соединения формулы (IIc)
Figure 00000005
которое подвергают взаимодействию с трет-бутилизотиоцианатом для получения соединения формулы (II)
Figure 00000006
12. Способ получения соединений формулы (I), определенных в п.1, где R 1 - ОН, а R2 - H, включающий стадию циклизации производного формулы
Figure 00000007
и, необязательно, превращение продукта в фармацевтически приемлемую соль.
13. Способ получения по п.12, в котором циклизацию проводят в кислой среде при температуре около 100°С.
14. Способ получения по п.13, в котором в качестве кислой среды предпочтительно используют 6 н. соляную кислоту.
15. Способ получения соединений формулы (IV) по п.12, включающий стадию реакции соединения формулы (V)
Figure 00000008
,
где Ra и Rc либо атомы водорода, либо защитные группы аминной и спиртовой функции, такие как COMe или COO-трет-Bu для Ra, и такие как трет-бутилдиметилсилил для Rc,
с пара-толуолсульфонилхлоридом в присутствии основания в спиртовых растворах для получения соединения формулы (VI)
Figure 00000009
которое подвергают воздействию вещества, снимающего защитные группы для получения соединения формулы (VII)
Figure 00000010
которое подвергают взаимодействию с трет-бутилизотиоцианатом для получения соединения формулы (IV), определенного как указано в п.12.
16. Соединения формул IV, V, VI, VII, определенные как указано в п.15.
17. Соединения формул II, IIa, IIb, IIc, определенные как указано в п.11, за исключением 2-ацетиламин-3-(2-этоксипиридин-4-ил)этилпропионата.
18. Соединения, представляющие собой следующие соединения:
N-(трет-бутил)-N'-[2-гидрокси-1-(3-метоксипиридин-4-илметил)этил]тиомочевина,
2-амино-3-(3-метоксипиридин-4-ил)-1-пропанол,
N-[1-(трет-бутилдиметилсиланилоксиметил)-2-(3-метоксипиридин-4-ил)этил]ацетамид и
N-[1-(трет-бутилдиметилсиланилоксиметил)-2-(1-оксипиридин-4-ил)этил]ацетамид.
RU2004117531/04A 2001-11-09 2002-11-07 Использование производных 2-амино-4-пиридилметилтиазолина в качестве ингибиторов индуцибельной no-синтазы RU2004117531A (ru)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR01/14508 2001-11-09
FR0114508A FR2832150B1 (fr) 2001-11-09 2001-11-09 Utilisation de derives de 2-amino-4-pyridylmethyl-thiazoline comme inhibiteurs de no-synthase inductible
US35297802P 2002-01-30 2002-01-30
US60/352,978 2002-01-30

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DE10240735A1 (de) * 2002-08-29 2004-03-18 Eberhard-Karls-Universität Tübingen Universitätsklinikum Verwendung von Modulatoren der NO-Signalkaskade und pharmazeutische Zusammensetzung
EP1942105B8 (en) * 2005-10-25 2014-08-13 Shionogi&Co., Ltd. Aminodihydrothiazine derivative
US8653067B2 (en) 2007-04-24 2014-02-18 Shionogi & Co., Ltd. Pharmaceutical composition for treating Alzheimer's disease
KR20100017255A (ko) 2007-04-24 2010-02-16 시오노기 앤드 컴파니, 리미티드 환식기로 치환된 아미노다이하이드로싸이아진 유도체
US8637504B2 (en) 2008-06-13 2014-01-28 Shionogi & Co., Ltd. Sulfur-containing heterocyclic derivative having beta secretase inhibitory activity
EP2360155A4 (en) 2008-10-22 2012-06-20 Shionogi & Co 2-AMINOPYRIDIN-4-ON AND 2-AMINOPYRIDINE DERIVATIVE WITH BACE1-HEMDERING EFFECT
RU2012129168A (ru) 2009-12-11 2014-01-20 Сионоги Энд Ко. Лтд. Производные оксазина
CA2816285A1 (en) 2010-10-29 2012-05-03 Shionogi & Co., Ltd. Naphthyridine derivative
JP5766198B2 (ja) 2010-10-29 2015-08-19 塩野義製薬株式会社 縮合アミノジヒドロピリミジン誘導体
CN103608345A (zh) 2011-04-26 2014-02-26 盐野义制药株式会社 噁嗪衍生物和含有该噁嗪衍生物的bace1抑制剂
WO2014065434A1 (en) 2012-10-24 2014-05-01 Shionogi & Co., Ltd. Dihydrooxazine or oxazepine derivatives having bace1 inhibitory activity

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WO1996014842A1 (en) * 1994-11-15 1996-05-23 Merck & Co., Inc. Substituted heterocycles as inhibitors of nitric oxide synthase
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IL161843A0 (en) 2005-11-20
CN1288153C (zh) 2006-12-06
JP2005517634A (ja) 2005-06-16
CY1110284T1 (el) 2015-01-14
IL161843A (en) 2011-08-31
DK1450750T3 (da) 2010-03-08
NO20033131D0 (no) 2003-07-08
MXPA04004213A (es) 2004-07-08
PL370267A1 (en) 2005-05-16
US20030153605A1 (en) 2003-08-14
CA2465877C (fr) 2009-12-29
DE60234117D1 (de) 2009-12-03
NO20033131L (no) 2003-08-27
HUP0402033A2 (hu) 2005-02-28
WO2003039446A2 (fr) 2003-05-15
WO2003039446A3 (fr) 2003-11-27
EP1450750A2 (fr) 2004-09-01
CA2465877A1 (fr) 2003-05-15
BR0206368A (pt) 2004-02-10
CN1602311A (zh) 2005-03-30
MA27143A1 (fr) 2005-01-03
HRP20040402A2 (en) 2004-10-31
EP1450750B1 (fr) 2009-10-21
ATE446295T1 (de) 2009-11-15
PT1450750E (pt) 2010-01-18
SI1450750T1 (sl) 2010-02-26
JP4342309B2 (ja) 2009-10-14

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