RU2215733C2 - Производные 1,3-пропандиола и их применение в качестве биологически активных веществ - Google Patents

Производные 1,3-пропандиола и их применение в качестве биологически активных веществ Download PDF

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RU2215733C2
RU2215733C2 RU97119631/04A RU97119631A RU2215733C2 RU 2215733 C2 RU2215733 C2 RU 2215733C2 RU 97119631/04 A RU97119631/04 A RU 97119631/04A RU 97119631 A RU97119631 A RU 97119631A RU 2215733 C2 RU2215733 C2 RU 2215733C2
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acid
propanediol
gamma
group
derivatives
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RU97119631/04A
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RU97119631A (ru
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Дэвид Фредерик ХОРРОБИН (GB)
Дэвид Фредерик ХОРРОБИН
Мехар МАНКУ (GB)
Мехар МАНКУ
Остин МакМОРДИ (GB)
Остин МакМОРДИ
Филип НОУЛЗ (GB)
Филип НОУЛЗ
Петер РЕДДЕН (CA)
Петер РЕДДЕН
Андреа ПИТТ (GB)
Андреа ПИТТ
Пол БРЭДЛИ (GB)
Пол БРЭДЛИ
Пол УЭЙКФИЛД (GB)
Пол УЭЙКФИЛД
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Скариста Лимитед
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Priority claimed from GBGB9508823.3A external-priority patent/GB9508823D0/en
Priority claimed from GBGB9517107.0A external-priority patent/GB9517107D0/en
Priority claimed from GBGB9605440.8A external-priority patent/GB9605440D0/en
Application filed by Скариста Лимитед filed Critical Скариста Лимитед
Publication of RU97119631A publication Critical patent/RU97119631A/ru
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Abstract

Изобретение относится к новым соединениям со структурой, связанной 1,3-пропандиолом, обладающим способностью проникать через липидные барьеры, формулы 1, где R1 обозначает ацильную группу или группу жирного спирта, производную от С12-30, предпочтительно C16-30 жирной кислоты желательно с двумя или более двойными связями в цис- или транс-положении, и R2 обозначает водород, ацильную группу или группу жирного спирта, которая является такой же или отличной от указанной для R1 либо является биологически активным остатком, отличным от остатка ниацина, химическая структура которого позволяет связаться с 1,3-пропандиолом через доступную карбоксильную, спиртовую или аминогруппу. Соединения со структурой, связанной 1,3-пропандиолом, обладающие способностью проникать через липидные барьеры, формулы 1, где R1 обозначает ацильную группу или группу жирного спирта, производную от С12-30, предпочтительно С16-30 жирной кислоты желательно с двумя или более двойными связями в цис- или транс-положении, и R2 обозначает водород, ацильную группу или группу жирного спирта, которая является такой же или отличной от указанной для R1 либо является биологически активным остатком, отличным от остатка ниацина, химическая структура которого позволяет связаться с 1,3-пропандиолом через доступную карбоксильную, спиртовую или аминогруппу, в которых между группой R1 и/или R2 и остатком 1,3-пропандиола включена фосфатная, сукцинатная или другая бифункциональная кислотная группа, в частности, когда R2 является биологически активным остатком с гидроксильной или амино функциональными группами. Лекарственный препарат для терапии для переноса лекарственного средства или другого активного вещества через липидные мембраны в организме либо имеющий действие, дополнительное, или комплементарное, или синергическое вместе с R1, содержащий в качестве активного агента соединение формулы 1. Технический результат - новые соединения, обладающие способностью проникать через липидные барьеры. 7 с. и 8 з.п.ф-лы.

Description

Текст описания в факсимильном виде (см. графическую часть).

Claims (15)

1. Соединения со структурой, связанной 1,3-пропандиолом, обладающие способностью проникать через липидные барьеры:
Figure 00000003

где R1 обозначает ацильную группу или группу жирного спирта, производную от С12-C30, предпочтительно С16-C30 жирной кислоты желательно с двумя или более двойными связями в цис- или транс-положении;
R2 обозначает водород, ацильную группу или группу жирного спирта, которая является такой же или отличной от указанной для R1 либо является биологически активным остатком, отличным от остатка ниацина, химическая структура которого позволяет связаться с 1,3-пропандиолом через доступную карбоксильную, спиртовую или аминогруппу.
2. Соединения со структурой, связанной 1,3-пропандиолом, обладающие способностью проникать через липидные барьеры:
Figure 00000004

где R1 обозначает ацильную группу или группу жирного спирта, производную от С12-C30, предпочтительно С16-C30 жирной кислоты, желательно с двумя или более двойными связями в цис- или транс-положении;
R2 обозначает водород, ацильную группу или группу жирного спирта, которая является такой же или отличной от указанной для R1 либо является биологически активным остатком, отличным от остатка ниацина, химическая структура которого позволяет связаться с 1,3-пропандиолом через доступную карбоксильную, спиртовую или аминогруппу, в которых между группой R1 и/или R2 и остатком 1,3-пропандиола включена фосфатная, сукцинатная или другая бифункциональная кислотная группа, в частности, когда R2 является биологически активным остатком с гидроксильной или амино функциональными группами.
3. Соединение по п. 1 или 2, в котором жирная кислота является незаменимой жирной кислотой ряда n-6 или n-3, или олеиновой кислотой, или колумбиновой кислотой, или паринаровой кислотой, или сопряженной линолевой кислотой.
4. Соединение по п. 3, в котором жирная кислота является гамма-линоленовой кислотой, дигомо-гамма-линоленовой кислотой, арахидоновой кислотой, адреновой кислотой, стеаридоновой кислотой, эйкозапентаеновой кислотой, докозапентаеновой кислотой n-3, докозагексаеновой кислотой или сопряженной линолевой кислотой.
5. Соединение по пп. 1-3 или 4, в котором R2 является лекарственным средством или другим активным веществом, для которого необходимо проникать через липидные мембраны в организме, чтобы оказывать необходимое действие внутри клетки или при перемещении в клетку, в которой оно должно действовать, или проходить через кожу, гематоэнцефалический или другие барьеры.
6. Соединение по пп. 1-3 или 4, в котором независимо от необходимости проникновения через липидные мембраны R2 является лекарственным средством, витамином, аминокислотой, антиоксидантом или другим активным веществом, которое требуется для оказания аддитивного, комплементарного или синергического действия вместе с R1.
7. Лекарственный препарат для терапии для переноса лекарственного средства или другого активного вещества через липидные мембраны в организме либо имеющий действие, дополнительное, или комплементарное, или синергическое вместе с R1, отличающийся тем, что в качестве активного агента включает соединение по любому из предшествующих пп. 1-4.
8. Соединения по любому из пп. 1-4 как таковые, кроме соединений, в которых как R1, так и R2 представляют остатки насыщенных жирных кислот, и соединений, в которых R1 и R2 имеют одинаковые значения и являются производными олеиновой кислоты, линолевой кислоты или альфа-линоленовой кислоты.
9. Соединения по любому из пп. 1-6 для получения препаратов для ухода за кожей или волосами или лечения кожных болезней.
10. Соединения по любому из пп. 1-6 для получения продуктов питания, пищевых добавок или кормовых добавок.
11. Производные 1,3-пропандиола, содержащие две жирные кислоты, из которых одна жирная кислота является гамма-линоленовой кислотой или дигомо-гамма-линоленовой кислотой, а другая гамма-линоленовой кислотой, дигомо-гамма-линоленовой кислотой, стеаридоновой кислотой, эйкозапентаеновой кислотой, докозагексаеновой кислотой, сопряженной линолевой кислотой или колумбиновой кислотой, предназначенные для использования в терапии.
12. Производные 1,3-пропандиола, содержащие две жирные кислоты, из которых одна жирная кислота является арахидоновой кислотой, а другая - арахидоновой кислотой, гамма-линоленовой кислотой, докозагексаеновой кислотой, дигомо-гамма-линоленовой кислотой или эйкозапентаеновой кислотой, предназначенные для использования в терапии.
13. Производные 1,3-пропандиола, содержащие две жирные кислоты, из которых одна жирная кислота является эйкозапентаеновой кислотой, а другая - эйкозапентаеновой кислотой или докозагексаеновой кислотой, предназначенные для использования в терапии.
14. Производные 1,3-пропандиола, содержащие в одном положении жирную кислоту, выбранную из гамма-линоленовой кислоты, дигомо-гамма-линоленовой кислоты, арахидоновой кислоты, стеаридоновой кислоты, сопряженной линолевой кислоты, эйкозапентаеновой кислоты или докозагексаеновой кислоты, а в другом положении средство, выбранное из указанных ниже, химическая структура которого позволяет ему связываться с 1,3-пропандиолом через доступную карбоксильную, спиртовую или аминогруппу: (a) триптофан; (b) фенилаланин; (c)аргинин; (d) карнитин или производные карнитина; (e) любая другая аминокислота или ее производные или аминолевулиновая кислота или ее производные; (f) аденилсукцинат или его производные; (g) аспирин, салициловая кислота, индометацин, ибупрофен или любое нестероидное противовоспалительное лекарственное средство; (h) любой антибиотик, в частности тетрациклин, клиндамицин, миноциклин, хлортетрациклин и эритромицин; (i) любое противомалярийное или антипротозойное средство, в частности хлорохин, мепакрин, хинакрин и мефлохин; (j) любое противогрибковое лекарственное средство, в частности метронидазол и противогрибковые имидазолы, нитроимидазолы и амфотерицин; (k) любой противовоспалительный стероид, в частности гидрокортизон и бетаметазон, беклометазон и будезонид; (l) любой гонадальный стероид, в частности оэстрогены, прогестогены и андрогены; (m) любой надпочечниковый стероид, в частности дегидроэпиандростерон; (n) любой ретиноид, в частности третиноин и изотретиноин; (о) любое противораковое средство; (p) любое антипсихотическое средство; (q) любой антидепрессант; (r) любой транквилизатор; (s) любое иммуносупрессивное средство, в частности циклоспорин и такролимус; (t) любой ингибитор протонного насоса или антагонист Н2; (u) любое мочегонное средство; (v) любой антагонист кальция; (w) любой ингибитор ангиотензинпревращающего фермента или антагонист ангиотензина; (x) любой бета-блокатор; (y) любое противоэпилептическое лекарственное средство, в частности фенитоин, карбамазепин, валпроат, этосуксимид, вигабатрин или ламотригин; (z) любое гиполипидемическсе средство, в частности фибраты и статины; (аа) любые пероральные гипогликемические или инсулин-сенсибилизирующие средства; (bb) любой бифосфонат; (ее) любое контрастное средство, применяемое в радиологии, в том числе соединения диатризоата, иодипамид, иогликаматы, иопаноаты, иофендилат, иоталамат, иоксаглат, метризамид и их производные; (dd) любой пептид или белок, в том числе инсулин, кальцитонин или эритропоетин; (ее) любой витамин; (ff) любой антиоксидант; (gg) любой порфирин, хлорин или лекарственное средство на основе бактериохлорина, в частности их тетракис(гидроксифенильные) производные.
15. Производные 1,3-пропандиола по п. 14, содержащие в одном положении жирную кислоту, выбранную из гамма-линоленовой кислоты, дигомо-гамма-линоленовой кислоты, арахидоновой кислоты, стеаридоновой кислоты, сопряженной линолевой кислоты, эйкозапентаеновой кислоты или докозагексаеновой кислоты, а в другом положении - витамин или антиоксидант, химическая структура которого позволяет ему связаться с 1,3-пропандиолом через доступную карбоксильную, спиртовую или аминогруппу, для использования в пищевых добавках, продуктах питания или питательных веществах.
Приоритет по пунктам и признакам:
01.05.1995 по пп. 1 и 2, где R1 и R2 группы, производные от жирной кислоты с двумя или более цис- или транс двойными связями, биологически активный остаток, связанный с 1,3-пропандиолом;
п. 3, где жирная кислота является незаменимой жирной кислотой ряда n-6 или n-3;
п. 4, за исключением сопряженной линолевой кислоты;
п. 14, где производные 1,3-пропандиола, содержащие в одном положении жирную кислоту, выбранную из гамма-линоленовой кислоты, дигомо-гамма-линоленовой кислоты, арахидоновой кислоты, стеаридоновой кислоты, сопряженной линолевой кислоты, эйкозапентаеновой кислоты или докозагексаеновой кислоты, а в другом положении лекарственное средство (а), (с), аминокислоты (е), (g), (h), метронидазол (j), (k), (о), (р), (q) и витамины группы (В) (ее);
п. 15, где производные 1,3-пропандиола, содержащие в одном положении жирную кислоту, выбранную из гамма-линоленовой кислоты, дигомо-гамма-линоленовой кислоты, арахидоновой кислоты, стеаридоновой кислоты, сопряженной линолевой кислоты, эйкозапентаеновой кислоты или докозагексаеновой кислоты, а в другом положении витамин группы В;
21.08.1995 по п. 3, за исключением сопряженной линолевой кислоты;
п. 9 - для ухода за кожей;
пп. 10, 12 и 13;
15.03.1996 по пп. 1 и 2, за исключением признака "отличный от остатка ниацина";
п. 8, за исключением признаков, исключающих ряд соединений;
п. 14, где производные 1,3-пропандиола, содержащие в одном положении жирную кислоту, выбранную из гамма-линоленовой кислоты, дигомо-гамма-линоленовой кислоты, арахидоновой кислоты, стеаридоновой кислоты, сопряженной линолевой кислоты, эйкозапентаеновой кислоты или докозагексаеновой кислоты, а в другом - положении - лекарственное средство (b), производные карнитина (d), хлорохин, мепакрин (i), (v), (cc), пептиды (dd), (ее), (ff);
п. 15, за исключением сопряженной линолевой кислоты.
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