RU2015151204A - Композиции и способы - Google Patents
Композиции и способы Download PDFInfo
- Publication number
- RU2015151204A RU2015151204A RU2015151204A RU2015151204A RU2015151204A RU 2015151204 A RU2015151204 A RU 2015151204A RU 2015151204 A RU2015151204 A RU 2015151204A RU 2015151204 A RU2015151204 A RU 2015151204A RU 2015151204 A RU2015151204 A RU 2015151204A
- Authority
- RU
- Russia
- Prior art keywords
- compound according
- modified
- compound
- modified oligonucleotide
- mces
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims 10
- 238000000034 method Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 28
- 108091034117 Oligonucleotide Proteins 0.000 claims 15
- 230000001268 conjugating effect Effects 0.000 claims 10
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims 6
- 208000030159 metabolic disease Diseases 0.000 claims 6
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical group CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims 6
- 239000003937 drug carrier Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 229930024421 Adenine Natural products 0.000 claims 3
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 3
- 206010070901 Diabetic dyslipidaemia Diseases 0.000 claims 3
- 206010022489 Insulin Resistance Diseases 0.000 claims 3
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 208000021017 Weight Gain Diseases 0.000 claims 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 3
- 229960000643 adenine Drugs 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 208000016097 disease of metabolism Diseases 0.000 claims 3
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 3
- 239000002777 nucleoside Substances 0.000 claims 3
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 229940113082 thymine Drugs 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- 230000004584 weight gain Effects 0.000 claims 3
- 235000019786 weight gain Nutrition 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- LRSASMSXMSNRBT-UHFFFAOYSA-N 5-methylcytosine Chemical group CC1=CNC(=O)N=C1N LRSASMSXMSNRBT-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002829 nitrogen Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000004713 phosphodiesters Chemical class 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7088—Compounds having three or more nucleosides or nucleotides
- A61K31/7125—Nucleic acids or oligonucleotides having modified internucleoside linkage, i.e. other than 3'-5' phosphodiesters
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7088—Compounds having three or more nucleosides or nucleotides
- A61K31/7105—Natural ribonucleic acids, i.e. containing only riboses attached to adenine, guanine, cytosine or uracil and having 3'-5' phosphodiester links
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Claims (60)
1. Соединение, содержащее модифицированный олигонуклеотид и конъгирующую группу, причем модифицированный олигонуклеотид состоит из последовательности азотистых оснований SEQ ID NO: 81, 55 или 59, при этом конъгирующая группа содержит
и при этом конъгирующая группа связана с модифицированным олигонуклеотидом на 5'-конце модифицированного олигонуклеотида.
2. Соединение по п. 1, отличающееся тем, что модифицированный олигонуклеотид содержит по меньшей мере один модифицированный сахар.
3. Соединение по п. 2, отличающееся тем, что модифицированный сахар представляет собой бициклический сахар.
4. Соединение по п. 3, отличающееся тем, что бициклический сахар выбран из группы, состоящей из: 4'-(СН2)-O-2' (LNA); 4'-(СН2)2-O-2' (ENA) и 4'-СН(СН3)-O-2' (cEt).
5. Соединение по п. 3, отличающееся тем, что модифицированный сахар представляет собой 2'-O-метоксиэтиловый сахар.
6. Соединение по п. 1, отличающееся тем, что модифицированный олигонуклеотид содержит по меньшей мере одно модифицированное азотистое основание.
7. Соединение по п. 6, отличающееся тем, что модифицированное азотистое основание представляет собой 5-метилцитозин.
8. Соединение по п. 1, отличающееся тем, что соединение является одноцепочечным.
9. Соединение по п. 1, отличающееся тем, что соединение является двухцепочечным.
10. Соединение по п. 1, отличающееся тем, что модифицированный олигонуклеотид содержит по меньшей мере одну модифицированную межнуклеозидную связь.
11. Соединение по п. 10, отличающееся тем, что модифицированная межнуклеозидная связь представляет собой тиофосфатную межнуклеозидную связь.
12. Соединение по п. 10, отличающееся тем, что модифицированный олигонуклеотид содержит по меньшей мере одну фосфодиэфирную межнуклеозидную связь.
13. Соединение по п. 1, отличающееся тем, что конъюгирующая группа содержит
где Q13 представляет собой Н или O(СН2)2-ОСН3;
А представляет собой модифицированный олигонуклеотид; и
Вх представляет собой фрагмент гетероциклического основания.
14. Композиция, содержащая соединение по любому из пп. 1-13 или его соль и по меньшей мере один фармацевтически приемлемый носитель или растворитель.
15. Пролекарство, содержащее соединение по любому из пп. 1-13.
16. Применение соединения по любому из пп. 1-13 или композиции по п. 14 в способе, включающем введение животному.
17. Применение по п. 16, отличающееся тем, что животное представляет собой человека.
18. Применение по п. 16, включающее совместное введение указанного соединения или композиции и второго агента.
19. Соединение, содержащее модифицированный олигонуклеотид и конъюгирующую группу, при этом конъюгирующая группа содержит
и при этом модифицированный олигонуклеотид имеет формулу Ges Ges Tes Tds mCds mCds mCds Gds Ads Gds Gds Tds Gds mCes mCes mCes Ae (SEQ ID NO: 81), где
A - аденин,
mC - 5'-метилцитозин,
G - гуанин,
T - тимин,
e - 2'-O-метоксиэтиловый модифицированный нуклеозид,
d - 2'-дезоксинуклеозид и
s - тиофосфатная межнуклеозидная связь.
20. Композиция, содержащая соединение по п. 19 или его соль и по меньшей мере один фармацевтически приемлемый носитель или растворитель.
21. Применение соединения по п. 19 или комозиции по п. 20 для лечения метаболических заболеваний, при этом метаболическое заболевание необязательно представляет собой метаболический синдром, сахарный диабет, инсулинорезистентность, диабетическую дислипидемию, гипертриглицеридемию, ожирение или рост массы тела.
22. Соединение, содержащее модифицированный олигонуклеотид и конъюгирующую группу, при этом конъюгирующая группа содержит
и при этом модифицированный олигонуклеотид имеет формулу Aes Aes Tes Ges Ges Tds Tds Tds Ads Tds Tds mCds mCds Ads Tds Ges Ges mCes mCes Ae (SEQ ID NO: 55), где
A - аденин,
mC - 5'-метилцитозин,
G - гуанин,
T - тимин,
e - 2'-O-метоксиэтиловый модифицированный нуклеозид,
d - 2'-дезоксинуклеозид, и
s - тиофосфатная межнуклеозидная связь.
23. Композиция, содержащая соединение по п. 22 или его соль и по меньшей мере один фармацевтически приемлемый носитель или растворитель.
24. Применение соединение по п. 22 или комозиции по п. 23 для лечения метаболических заболеваний, при этом метаболическое заболевание необязательно представляет собой метаболический синдром, сахарный диабет, инсулинорезистентность, диабетическую дислипидемию, гипертриглицеридемию, ожирение или рост массы тела.
25. Соединение, содержащее модифицированный олигонуклеотид и конъюгирующую группу, при этом конъюгирующая группа содержит
и при этом модифицированный олигонуклеотид имеет формулу Ges mCes Aes mCes Aes mCds Tds mCds Ads Gds mCds Ads Gds Gds Ads mCes mCes mCes mCes mCe (SEQ ID NO: 59), при этом
A - аденин,
mC - 5'-метилцитозин,
G - гуанин,
T - тимин,
е - 2'-O-метоксиэтиловый модифицированный нуклеозид,
d - 2'-дезоксинуклеозид, и
s - тиофосфатная межнуклеозидная связь.
26. Композиция, содержащая соединение по п. 25 или его соль и по меньшей мере один фармацевтически приемлемый носитель или растворитель.
27. Применение соединения по п. 25 или комозиции по п. 26 для лечения метаболических заболеваний, при этом метаболическое заболевание необязательно представляет собой метаболический синдром, сахарный диабет, инсулинорезистентность, диабетическую дислипидемию, гипертриглицеридемию, ожирение или рост массы тела.
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