RU2016132415A - Новые производные каннабигерола - Google Patents
Новые производные каннабигерола Download PDFInfo
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- RU2016132415A RU2016132415A RU2016132415A RU2016132415A RU2016132415A RU 2016132415 A RU2016132415 A RU 2016132415A RU 2016132415 A RU2016132415 A RU 2016132415A RU 2016132415 A RU2016132415 A RU 2016132415A RU 2016132415 A RU2016132415 A RU 2016132415A
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- Prior art keywords
- dimethyl
- dienyl
- octa
- benzoquinone
- pentyl
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- QXACEHWTBCFNSA-SFQUDFHCSA-N cannabigerol Chemical class CCCCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 QXACEHWTBCFNSA-SFQUDFHCSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 230000001404 mediated effect Effects 0.000 claims 5
- -1 (E) -3,7-dimethyl-octa-2,6-dienyl Chemical group 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- UAYZUEGWYMZXAR-UHFFFAOYSA-N CC(=CCC1=C(C(C(=C(C1=O)C(=O)OC)CCCCC)=O)O)CCC=C(C)C Chemical compound CC(=CCC1=C(C(C(=C(C1=O)C(=O)OC)CCCCC)=O)O)CCC=C(C)C UAYZUEGWYMZXAR-UHFFFAOYSA-N 0.000 claims 2
- ZBMDVOKFJICGSB-UHFFFAOYSA-N CC(=CCC1=C(C(C(=C(C1=O)NC)CCCCC)=O)O)CCC=C(C)C Chemical compound CC(=CCC1=C(C(C(=C(C1=O)NC)CCCCC)=O)O)CCC=C(C)C ZBMDVOKFJICGSB-UHFFFAOYSA-N 0.000 claims 2
- RDUVLSYGVHSQJL-UHFFFAOYSA-N CC(=CCC1=C(C(C(=C(C1=O)NCC(C)C)CCCCC)=O)O)CCC=C(C)C Chemical compound CC(=CCC1=C(C(C(=C(C1=O)NCC(C)C)CCCCC)=O)O)CCC=C(C)C RDUVLSYGVHSQJL-UHFFFAOYSA-N 0.000 claims 2
- FWRXHQONRMSHII-UHFFFAOYSA-N CC(=CCC1=C(C(C(=C(C1=O)NCC)CCCCC)=O)O)CCC=C(C)C Chemical compound CC(=CCC1=C(C(C(=C(C1=O)NCC)CCCCC)=O)O)CCC=C(C)C FWRXHQONRMSHII-UHFFFAOYSA-N 0.000 claims 2
- KOPQHVLVALHDSF-UHFFFAOYSA-N CC(=CCC1=C(C(C(=C(C1=O)NCC1=CC=CC=C1)CCCCC)=O)O)CCC=C(C)C Chemical compound CC(=CCC1=C(C(C(=C(C1=O)NCC1=CC=CC=C1)CCCCC)=O)O)CCC=C(C)C KOPQHVLVALHDSF-UHFFFAOYSA-N 0.000 claims 2
- IMTDOEUZJAJJQR-UHFFFAOYSA-N CC(=CCC1=C(C(C(=C(C1=O)NCCC(C)C)CCCCC)=O)O)CCC=C(C)C Chemical compound CC(=CCC1=C(C(C(=C(C1=O)NCCC(C)C)CCCCC)=O)O)CCC=C(C)C IMTDOEUZJAJJQR-UHFFFAOYSA-N 0.000 claims 2
- UGNZFPTYCFPJKZ-UHFFFAOYSA-N CC(=CCC1=C(C(C(=C(C1=O)NCCCC)CCCCC)=O)O)CCC=C(C)C Chemical compound CC(=CCC1=C(C(C(=C(C1=O)NCCCC)CCCCC)=O)O)CCC=C(C)C UGNZFPTYCFPJKZ-UHFFFAOYSA-N 0.000 claims 2
- XOBMKONDRBMRPA-UHFFFAOYSA-N CC(=CCC1=C(C(C(=C(C1=O)NCCCCC)CCCCC)=O)O)CCC=C(C)C Chemical compound CC(=CCC1=C(C(C(=C(C1=O)NCCCCC)CCCCC)=O)O)CCC=C(C)C XOBMKONDRBMRPA-UHFFFAOYSA-N 0.000 claims 2
- OYRODUCUPJBDIR-UHFFFAOYSA-N CC(=CCC=1C(C(=C(C(C1O)=O)CCCCC)NC(C)C)=O)CCC=C(C)C Chemical compound CC(=CCC=1C(C(=C(C(C1O)=O)CCCCC)NC(C)C)=O)CCC=C(C)C OYRODUCUPJBDIR-UHFFFAOYSA-N 0.000 claims 2
- 208000007882 Gastritis Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010033645 Pancreatitis Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010039710 Scleroderma Diseases 0.000 claims 2
- 206010072170 Skin wound Diseases 0.000 claims 2
- 125000006323 alkenyl amino group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000006319 alkynyl amino group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 239000000539 dimer Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 230000036560 skin regeneration Effects 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 230000029663 wound healing Effects 0.000 claims 2
- IBISNRABPRDDBD-UHFFFAOYSA-N CC(=CCC1=C(C(C(=C(C1=O)NCC(C)(C)C)CCCCC)=O)O)CCC=C(C)C Chemical compound CC(=CCC1=C(C(C(=C(C1=O)NCC(C)(C)C)CCCCC)=O)O)CCC=C(C)C IBISNRABPRDDBD-UHFFFAOYSA-N 0.000 claims 1
- PYDFBQBSWOSGJW-IENBMRAWSA-N CCCCCC(C1)C(C(C(CCCCC)C2)=CC(C/C=C(\C)/CCC=C(C)C)=C2O)=CC(C/C=C(\C)/CCC=C(C)C)=C1O Chemical compound CCCCCC(C1)C(C(C(CCCCC)C2)=CC(C/C=C(\C)/CCC=C(C)C)=C2O)=CC(C/C=C(\C)/CCC=C(C)C)=C1O PYDFBQBSWOSGJW-IENBMRAWSA-N 0.000 claims 1
- 230000004071 biological effect Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 claims 1
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Claims (57)
1. Соединения Формулы (I) или их производные,
где R представляет собой атом углерода группы, представленной: арильной, линейной или разветвленной алкенильной, линейной или разветвленной алкинильной или линейной или разветвленной алкоксикарбонильной группами; или где R представляет собой атом азота группы, представленной: линейной или разветвленной алкиламино, ариламино, линейной или разветвленной алкениламино или линейной или разветвленной алкиниламино группами; или, в качестве альтернативы, R представляет собой связь между 2 молекулами Формулы (I), образующими димер.
2. Соединение по п. 1, выбранное из:
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-метоксикарбонил-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-этиламино-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-пентиламино-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-изобутиламино[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-бутиламино[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-метиламино-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-изопропиламино-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-бензиламино[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-(2,2-диметил-пропиламино)-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-(3-метил-бутиламино)-[1,4]бензохинон,
3,3'-бис((Е)-3,7-диметил-окта-2,6-диенил)-4,4'-дигидрокси-6,6,-дипентил-1,1'-би(циклогекса-3,6-диен)-2,2',5,5'-тетраон.
3. Композиция для лечения заболевания, опосредованного PPRAg, содержащая эффективное количество соединения Формулы (I) или его производного, и, необязательно, по меньшей мере дополнительное активное соединение, обладающее дополнительным или синергетическим биологическим действием и/или по меньшей мере фармацевтически инертный ингредиент, такой как наполнитель и/или носитель, при этом указанное соединение Формулы (I) представляет собой
где R представляет собой атом углерода группы, представленной: арильной, линейной или разветвленной алкенильной, линейной или разветвленной алкинильной или линейной или разветвленной алкоксикарбонильной группами; или где R представляет собой атом азота группы, представленной: линейной или разветвленной алкиламино, ариламино, линейной или разветвленной алкениламино или линейной или разветвленной алкиниламино группами; или, в качестве альтернативы, R представляет собой связь между 2 молекулами Формулы (I), образующими димер.
4. Композиция по п. 3, отличающаяся тем, что указанное соединение Формулы (I) выбрано из:
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-метоксикарбонил-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-этиламино-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-пентиламино-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-изобутиламино[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-бутиламино[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-метиламино-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-изопропиламино-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-бензиламино[1,4]бензохинон,
6-(3)7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-(2,2-диметил-пропиламино)-[1,4]бензохинон,
6-(3,7-диметил-окта-2,6-диенил)-5-гидрокси-3-пентил-2-(3-метил-бутиламино)-[1,4]бензохинон,
3,3'-бис ((Е)-3,7-диметил-окта-2,6-диенил)-4,4'-дигидрокси-6,6'-дипентил-1,1'-би(циклогекса-3,6-диен)-2,2',5,5'-тетраон.
5. Применение соединения по любому из п. 1 или 2 в качестве лекарственного средства для лечения заболевания, опосредованного PPRAg.
6. Применение по п. 5, отличающееся тем, что указанное опосредованное PPRAg заболевание выбрано из: атеросклероза, воспалительных заболеваний кишечника, ревматоидного артрита, фиброза печени, нефропатии, псориаза, заживления ран кожи, регенерации кожи, панкреатита, гастрита, нейродегенеративных расстройств,
нейровоспалительных расстройств, склеродермии, рака, гипертонии, ожирения или диабета II типа.
7. Применение композиции по любому из п. 3 или 4 в качестве лекарственного средства для лечения заболевания, опосредованного PPRAg.
8. Применение по п. 7, отличающееся тем, что указанное опосредованное PPRAg заболевание выбрано из: атеросклероза, воспалительных заболеваний кишечника, ревматоидного артрита, фиброза печени, нефропатии, псориаза, заживления ран кожи, регенерации кожи, панкреатита, гастрита, нейродегенеративных расстройств, нейровоспалительных расстройств, склеродермии, рака, гипертонии, ожирения или диабета II типа.
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