RU2334735C2 - Производные сульфониламиноуксусной кислоты и их применение в качестве антагонистов рецепторов орексина - Google Patents

Производные сульфониламиноуксусной кислоты и их применение в качестве антагонистов рецепторов орексина Download PDF

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RU2334735C2
RU2334735C2 RU2005114486/04A RU2005114486A RU2334735C2 RU 2334735 C2 RU2334735 C2 RU 2334735C2 RU 2005114486/04 A RU2005114486/04 A RU 2005114486/04A RU 2005114486 A RU2005114486 A RU 2005114486A RU 2334735 C2 RU2334735 C2 RU 2334735C2
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Russia
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amino
tert
butylbenzenesulfonyl
mixtures
ethyl
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RU2005114486/04A
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RU2005114486A (ru
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Амед ЭССАУИ (FR)
Амед ЭССАУИ
Мартин КЛОЗЕЛЬ (CH)
Мартин КЛОЗЕЛЬ
Томас ВЕЛЛЕР (CH)
Томас Веллер
Ральф КОБЕРШТАЙН (DE)
Ральф КОБЕРШТАЙН
Тьерри СИФФЕРЛЕН (FR)
Тьерри Сифферлен
Вальтер ФИШЛЬ (CH)
Вальтер ФИШЛЬ
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Актелион Фармасьютиклз Лтд.
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Abstract

Изобретение относится к производным сульфониламиноуксусной кислоты общей формулы I
Figure 00000001
в которой R1 - (низш.)алкил, циклоалкил, гидрокси(низш.)алкил, или циано(низш.)алкил;
R2 - (низш.)алкил, гидрокси(низш.)алкил, циклоалкил, незамещенный или замещенный фенил;
А означает 4-этилфенил, 4-изопропилфенил, 4-трет-бутилфенил, 2-метилфенил, 3-метилфенил, 4-циклопропилфенил, 3-фторфенил, 2-хлорфенил, 3-хлорфенил, 4-бромфенил, 2-трифторметилфенил, 3-трифторметилфенил, 4-(1-гидрокси-1-метилэтил)фенил, 3-хлор-4-метилфенил, 2-метокси-4-метилфенил, 3,4-дифторфенил, 1,2,3,4-тетрагидроизохинолин-7-ил, 2-метил-1,2,3,4-тетрагидроизохинолин-7-ил, 2-формил-1,2,3,4-тетрагидроизохинолин-7-ил, фенилэтенил, 1-нафтил, 2-нафтил, 3-метилпиридин-2-ил, 5-метилпиридин-2-ил, 5-изопропилпиридин-2-ил, 6-диметиламинопиридин-3-ил, 6-бром-5-хлорпиридин-3-ил или 8-хинолинил;
В означает фенил, шестичленную гетероарильную или девяти- либо десятичленную бициклическую гетероарильную группу, выбранную из пиридина, хинолина, изохинолина, бензимидазола, индола, которые являются незамещенными или независимо моно- или дизамещенными. Соединения могут быть использованы в качестве антагонистов рецепторов орексина. 15 з.п. ф-лы.

Description

Текст описания приведен в факсимильном виде.
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Claims (16)

1. Соединение формулы (I)
Figure 00000125
где А означает 4-этилфенил, 4-изопропилфенил, 4-трет-бутилфенил, 2-метилфенил, 3-метилфенил, 4-циклопропилфенил, 3-фторфенил, 2-хлорфенил, 3-хлорфенил, 4-бромфенил, 2-трифторметилфенил, 3-трифторметилфенил, 4-(1-гидрокси-1-метилэтил)фенил, 3-хлор-4-метилфенил, 2-метокси-4-метилфенил, 3,4-дифторфенил, 1,2,3,4-тетрагидроизохинолин-7-ил, 2-метил-1,2,3,4-тетрагидроизохинолин-7-ил, 2-формил-1,2,3,4-тетрагидроизохинолин-7-ил, фенилэтенил, 1-нафтил, 2-нафтил, 3-метилпиридин-2-ил, 5-метилпиридин-2-ил, 5-изопропилпиридин-2-ил, 6-диметиламинопиридин-3-ил, 6-бром-5-хлорпиридин-3-ил или 8-хинолинил;
В означает фенил, шестичленную гетероарильную или девяти- либо десятичленную бициклическую гетероарильную группу, выбранную из пиридина, хинолина, изохинолина, бензимидазола, индола, индазола и бензотиазола, которые являются незамещенными или независимо моно- или дизамещенными с помощью циано, галоида, (низш.)алкила, гидрокси(низш.)алкила, (низш.)алкокси, трифторметила, трифторметокси, амино или аминокарбонила; или циклогексильную группу, которая является незамещенной или монозамещенной с помощью (низш.)алкила; при условии, что в случае когда А означает 2-метилфенил или 4-бромфенил, фенильное кольцо, представленное В, является замещенным;
R1 означает (низш.)алкил, циклоалкил, гидрокси(низш.)алкил или циано(низш.)алкил;
R2 означает (низш.)алкил, гидрокси(низш.)алкил, циклоалкил; незамещенную или моно- либо дизамещенную фенильную группу, независимо замещенную с помощью циано, галоида, гидрокси, (низш.)алкила, (низш.)алкокси, амино или амино(низш.)алкила; незамещенную или моно- либо дизамещенную пяти- или шестичленную гетероарильную группу, выбранную из пиридина, пиррола, имидазола и тиазола, замещенную независимо с помощью (низш.)алкила, амино или амино(низш.)алкила; незамещенную девяти- или десятичленную бициклическую гетероарильную группу, выбранную из хинолина, изохинолина и индола;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
2. Соединение формулы (I) по п.1,
где А означает 4-этилфенильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
3. Соединение формулы (I) по п.1,
где А означает 4-изопропилфенильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
4. Соединение формулы (I) по п.1,
где А означает 4-трет-бутилфенильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
5. Соединение формулы (I) по п.1,
где А означает 2-метилфенильную группу;
В имеет значение, приведенное в п.1 при условии, что фенильная группа замещена;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
6. Соединение формулы (I) по п.1,
где А означает 3-метилфенильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
7. Соединение формулы (I) по п.1,
где А означает 4-(1-гидрокси-1-метилэтил)фенильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
8. Соединение формулы (I) по п.1,
где А означает 3-хлор-4-метилфенильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
9. Соединение формулы (I) по п.1,
где А означает 2-формил-1,2,3,4-тетрагидроизохинолин-7-ильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
10. Соединение формулы (I) по п.1,
где А означает 2-нафтильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
11. Соединение формулы (I) по п.1,
где А означает 3-метилпиридин-2-ильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
12. Соединение формулы (I) по п.1,
где А означает 5-изопропилпиридин-2-ильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
13. Соединение формулы (I) по п.1,
где А означает 6-диметиламинопиридин-3-ильную группу;
или его чистый энантиомер, смеси энантиомеров, чистый диастереоизомер, смеси диастереоизомеров, диастереоизомерный рацемат, смесь диастереоизомерных рацематов и мезо-формы; или его фармацевтически приемлемая соль, комплекс с растворителем, или его морфологическая форма.
14. Соединение по п.1, выбранное из группы, включающей
2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N,N-диэтилацетамид;
2-[(4-трет-бутилбензолсульфонил)(4-метоксифенил)амино]-N,N-диэтилацетамид;
2-[(4-трет-бутилбензолсульфонил)(3-метоксифенил)амино]-N,N-диэтилацетамид;
2-[(4-трет-бутилбензолсульфонил)-м-толиламино]-N,N-диэтилацетамид;
2-[(6-диметиламинопиридин-3-сульфонил)-n-толиламино]-N-этил-N-пиридин-2-илметилацетамид;
N-бензил-2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-этилацетамид;
2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-этил-N-пиридин-4-илметилацетамид;
N,N-диэтил-2-[(2-метоксифенил)(толуол-2-сульфонил)амино]ацетамид;
N-бензил-N-этил-2-[(6-метоксипиридин-3-ил)(толуол-2-сульфонил)амино]ацетамид;
N-бензил-N-этил-2-[(2-метоксифенил)(толуол-2-сульфонил)амино]ацетамид;
N-бензил-2-[(4-трет-бутилбензолсульфонил)(2-метоксифенил)амино]-N-этилацетамид;
N-бензил-N-этил-2-[(6-метоксипиридин-3-ил)(нафталин-2-сульфонил)амино]ацетамид;
2-[(4-треот-бутилбензолсульфонил)-n-толиламино]-N-этил-N-(2-гидроксиэтил)ацетамид;
2-[(3-хлор-4-метилбензолсульфонил)-n-толиламино]-N,N-диэтилацетамид;
N-бензил-2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-(2-гидроксиэтил)ацетамид;
2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-(2-цианоэтил)-N-этилацетамид;
2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-этил-N-пиридин-2-илметилацетамид;
2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-этил-N-пиридин-3 -илметилацетамид;
2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-этил-N-(6-метилпиридин-2-илметил)ацетамид;
2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-этил-N-тиазол-2-илметилацетамид;
2-[(4-трет-бутилбензолсульфонил)(3-диметиламинофенил)амино]-N,N-диэтилацетамид;
2-[(4-трет-бутилбензолсульфонил)(3-диметиламинофенил)амино]-N-этил-N-пиридин-2-илметилацетамид;
2-[(4-трет-бутилбензолсульфонил)(3-диметиламинофенил)амино]-N-этил-N-(6-метилпиридин-2-илметил)ацетамид;
2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-этил-N-(3-гидроксибензил)ацетамид;
2-[(4-трет-бутилбензолсульфонил)(1Н-индазол-6-ил)амино]-N-этил-N-(6-метилпиридин-2-илметил)ацетамид;
2-[(4-трет-бутилбензолсульфонил)(1Н-индазол-6-ил)амино]-N-этил-N-пиридин-2-илметил)ацетамид;
2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-(2-гидроксиэтил)-N-пиридин-2-илметилацетамид;
2-[(4-трет-бутилбензолсульфонил)(3-диметиламинофенил)амино]-N-(2-гидроксиэтил)-N-пиридин-2-илметилацетамид;
2-[(4-трет-бутилбензолсульфонил)-n-толиламино]-N-циклопропил-N-(3-метоксибензил)ацетамид;
2-[(4-трет-бутилбензолсульфонил)(3-диметиламинофенил)амино]-N-циклопропил-N-(3-метоксибензил)ацетамид;
N-этил-2-[(2-метоксифенил)(толуол-2-сульфонил)амино]-N-тиазол-2-илметилацетамид;
N-бензил-N-(2-гидроксиэтил)-2-[(2-метоксифенил)(толуол-2-сульфонил)амино]ацетамид;
N-этил-2-[(2-метоксифенил)(толуол-2-сульфонил)амино]-N-пиридин-2-илметилацетамид;
N-этил-N-(3-гидроксибензил)-2-[(2-метоксифенил)(толуол-2-сульфонил)амино]ацетамид;
N-этил-2-[(6-метоксипиридин-3-ил)(толуол-2-сульфонил)амино]-N-(6-метилпиридин-2-илметил)ацетамид;
N-бензил-N-(2-гидроксиэтил)-2-[(6-метоксипиридин-3-ил)(толуол-2-сульфонил)амино]ацетамид;
N-этил-2-[(6-метоксипиридин-3-ил)(толуол-2-сульфонил)амино]-N-пиридин-3-илметилацетамид;
N-этил-2-[(6-метоксипиридин-3-ил)(толуол-2-сульфонил)амино]-N-пиридин-2-илметилацетамид;
N-этил-2-[(2-метоксифенил)(3-метилпиридин-2-сульфонил)амино]-N-(6-метилпиридин-2-илметил)ацетамид;
N-бензил-N-этил-2-[(2-метоксифенил)(3-метилпиридин-2-сульфонил)амино]ацетамид;
2-[(4-трет-бутилбензолсульфонил)(6-метилпиридин-3-ил)амино]-N-этил-N-пиридин-2-илметилацетамид;
N-бензил-2-[(4-трет-бутилбензолсульфонил)(6-метилпиридин-3-ил)амино]-N-этилацетамид;
N-этил-2-[(6-метоксипиридин-3-ил)(3-метилпиридин-2-сульфонил)амино]-N-(6-метилпиридин-2-илметил)ацетамид;
N-бензил-N-этил-2-[(6-метоксипиридин-3-ил)(3-метилпиридин-2-сульфонил)амино]ацетамид,
или фармацевтически приемлемая соль такого соединения.
15. Соединение по любому из пп.1-14 или его фармацевтически приемлемая соль для применения в качестве лекарственных средств, предназначенных для лечения нарушений, которые ассоциированы с ролью орексинов.
16. Соединение по любому из пп.1-14 или его фармацевтически приемлемая соль для применения в качестве лекарственных средств, предназначенных для лечения пищевых нарушений, нарушений сна, сердечно-сосудистых нарушений, злокачественных опухолей, боли, депрессии, страха, шизофрении, нейродегенеративных нарушений или синдромов гипертермии.
RU2005114486/04A 2002-10-11 2003-10-06 Производные сульфониламиноуксусной кислоты и их применение в качестве антагонистов рецепторов орексина RU2334735C2 (ru)

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