RU2005121554A - Хиральные арилкетоны в лечении нейтрофил-зависимых воспалительных заболеваний - Google Patents

Хиральные арилкетоны в лечении нейтрофил-зависимых воспалительных заболеваний Download PDF

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RU2005121554A
RU2005121554A RU2005121554/04A RU2005121554A RU2005121554A RU 2005121554 A RU2005121554 A RU 2005121554A RU 2005121554/04 A RU2005121554/04 A RU 2005121554/04A RU 2005121554 A RU2005121554 A RU 2005121554A RU 2005121554 A RU2005121554 A RU 2005121554A
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phenyl
isobutylphenyl
methyl
oxopentanoate
oxobutyl
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Марчелло АЛЛЕГРЕТТИ (IT)
Марчелло Аллегретти
Риккардо БЕРТИНИ (IT)
Риккардо БЕРТИНИ
Мари Кандида ЧЕСТА (IT)
Мария Кандида ЧЕСТА
Чинци БИЦЦАРРИ (IT)
Чинция БИЦЦАРРИ
Франческо КОЛОТТА (IT)
Франческо Колотта
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Claims (7)

1. Применение (R,S)-1-арилэтилкетонов формулы I и их идивидуальных (R) и (S) энантиомеров
Figure 00000001
где Ar представляет собой фенил, необязательно замещенный от одного до трех заместителей, которые могут быть одинаковыми или отличаться друг от друга, выбранными из
галогена, С1-С4-алкила, С1-С4-алкокси, гидрокси, С1-С4-ацилокси, фенокси, циано, нитро, амино, С1-С4-ациламино, галоген-С1-С3-алкила, галоген-С1-С3-алкокси, бензоила;
или Ar представляет собой 4-тиеноилфенил, 4-(1-оксо-2-изоиндолинил)фенил, 3-хлор-4-(2,5-дигидро-1Н-пиррол-1-ил)фенил, 6-метокси-β-нафтил, 1-гидроксифенил-1-метил;
или Ar представляет собой группу формулы (III)
Figure 00000002
где А представляет собой бензил, фенокси, бензоил, бензоилоксим, 1-гидроксифенил-1-метил; В представляет собой гидрокси, С1-С4-ацилокси или группу формулы -О-С(=S)-N(СН3)2, или -S-С(=О)-N(СН3)2;
Ra и Rb независимо выбраны из группы, включающей водород, линейный или разветвленный С1-С6-алкил, фенил, α- или β-нафтил, 2,3,4-пиридил, С1-С4-алкилфенил, С1-С4-алкил(α- или β-нафтил), С1-С4-алкил(2,3,4-пиридил), циано (-CN), карбоксамид, карбоксил или карбоксиэфиры формулы CO2R", в которой R" представляет собой остаток линейного или разветвленного алифатического С1-С6-спирта, фосфонат PO(OR")2, где R" имеет вышеуказанные значения, или группу формулы Х-(СН2)n-Z, где Х представляет собой СО, SO или SO2 группу; Z представляет собой водород, трет-бутил, изопропил, CO2R", CN, фенил, α- или β-нафтил, 2,3,4-пиридил, С3-С6-циклоалкил, NH-BOC, NH2; n равно нулю или целому числу от 1 до 3;
или Ra и Rb вместе с атомом углерода, к которому они присоединены, образуют циклический остаток 2,2-дизамещенный 4,6-диоксо-1,3-диоксанил формулы II
Figure 00000003
где R' представляет собой метил или этил, или две группы R' образуют циклогексановое или циклопентановое кольцо,
для изготовления лекарственного препарата для лечения заболеваний, которые связаны с хемотаксисом PMN человека, вызванным ИЛ-8.
2. Применение по п.1, где в соединении Ar представляет собой группу 4-изобутилфенил, 3-бензоилфенил, 5-бензоилфенил, 2-ацетоксифенил, 3-феноксифенил.
3. Применение по п.1 или 2, где соединение выбрано из:
метил-(R)(-)-4-[(4'-изобутил)фенил]-3-оксопентаноат;
метил-(S)(+)-4-[(4'-изобутил)фенил]-3-оксопентаноат;
(R,S)-4-[(4'-изобутил)фенил]-3-оксопентановая кислота;
метил-(R)(-)-4-[(3'-бензоил)фенил]-3-оксопентаноат;
(R)(-)-3-[(4'-изобутил)фенил]бутан-2-он;
(S)(+)-3-[(4'-изобутил)фенил]бутан-2-он;
(R)(-)-3-[(3'-бензоил)фенил]бутан-2-он;
(R)(-)-диметил-3-(4-изобутилфенил)-2-оксобутан-1-фосфонат;
(S)(±)-диметил-3-(3'-феноксифенил)-2-оксобутил-1-фосфонат;
(R)(-)-2-(4-изобутилфенил)пентан-3-он;
(S)(+)-этил-4-[(3'-бензоил)фенил]-3-оксопентаноат;
(S)(+)-3-[(3'-бензоил)фенил]бутан-2-он;
(R)(-)-2-[(4-изобутилфенил)-4-фенилбутан-3-он;
(R)(-)-2-(4-изобутилфенил)-5-фенилпентан-3-он;
(R)(-)-2-(4-изобутилфенил)-5-(пирид-3-ил)-пентан-3-он;
(R,S)-5-(4'-изобутилфенил)гексан-2,4-дион;
(R,S)-1-фенил-5-(4'-изобутилфенил)-2,4-гександион;
(R,S)-1-(пирид-2-ил)-4-(4'-изобутилфенил)-1,3-пентандион;
(R)(-)-2-(4-изобутилфенил)-7-трет-бутоксикарбониламиногептан-3-он;
(R,S)-2-(4'-изобутилфенил)-3-оксобутил, метилсульфоксид;
(R,S)-2-(3'-бензоилфенил)-3-оксобутил, метилсульфоксид;
(R,S)-2-(4'-изобутилфенил)-3-оксобутил, метилсульфон;
(R,S)-2-(3'-бензоилфенил)-3-оксобутил, метилсульфон;
(R,S)-2-(3'-феноксифенил)-3-оксобутил, метилсульфон;
(R,S)-2-(4'-изобутилфенил)-3-оксобутил, фенилсульфон;
(R)(-)-4-(4'-пиридил)-2-[(4"-изобутил)фенил]бутан-3-он;
(R)(+)-5-[2-(4-изобутилфенил)пропион-1-ил]-2,2-диметил-1,3-диоксан-4,6-дион;
(R)(-)-5-[2-(3'-бензоилфенил)пропион-1-ил]-2,2-диметил-1,3-диоксан-4,6-дион;
(R)-2-[4-(1-оксо-2-изоиндолинил)фенил]-3-оксовалерамид;
(R)-2-[4-(1-оксо-2-изоиндолинил)фенил]-3-оксовалеронитрил.
4. Применение соединений
(R)(-)-метил-4-[(4'-бензоилокси)фенил]-3-оксопентаноат;
(R)(-)-метил-4-[(4'-изопропилсульфонилокси)фенил]-3-оксопентаноат; и
(R)(-)-метил-4-{[(4'-(2"-этил)фенилсульфониламино]фенил}-3-оксопентаноат
для изготовления лекарственного препарата для лечения заболеваний, которые связаны с хемотаксисом PMN человека, вызванным ИЛ-8.
5. Применение по п.1 или 2, где в соединении пространственная конфигурация атома углерода, к которому присоединена группа Ar, соответствует (R) энантиомеру.
6. Фармацевтическая композиция, содержащая соединение по любому из пп.1-5 в смеси с подходящим носителем.
7. Применение соединений, охарактеризованных в любом из пп.1-5, для изготовления лекарственных препаратов для лечения псориаза, ревматоидного артрита, язвенного колита, острого респираторного дистресс-синдрома (ARDS), идиопатического фиброза, гломерулонефрита, буллезной пузырчатки, и для профилактики и лечения повреждений, вызванных ишемией и реперфузией.
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