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US 11,401,231 B2Granted
Stilbene derivative and method for preparing same
AssigneeOzchela Inc.
InventorsMin-Kyung Lee, Jin-Kak Lee, Won-Seok Han
Life of this patent
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Abstract
This invention relates to a stilbene derivative and a method of preparing the same, and more particularly to a novel stilbene derivative for inhibiting the function of cyclophilin, which is effective at the prevention of cyclophilin-related diseases or at the treatment of symptoms of such diseases, and to a method of preparing the same.
Claims5
A compound represented by Chemical Formula 1 below or a pharmaceutically acceptable salt thereof:
- in Chemical Formula 1,
- A is CRa,
- B is CRb,
- G is CRe,
- J is CRf,
- M is CRg,
- D, E, and L are CRh,
- Rx is H,
- Ra is hydrogen, or a C1-C5 alkyl group,
- Rb is hydrogen,
- Rc is —CH2C(CH3)3,
- Rd is COOH or —COOR5 (R5 is a C1-C10 alkyl group or a C3-C10 cycloalkyl group, wherein the C1-C10 alkyl group may be substituted with at least one substituent selected from the group consisting of amine, a C6-C12 aryl, a C5-C10 heterocyclic group including nitrogen as a hetero atom, and a C3-C10 cycloalkyl group),
- Re is hydrogen, NH2, OH, or a C1-C10 alkyl group,
- Rf is hydrogen, NH2, OH, or a C1-C4 alkyl group,
- Rg is hydrogen, NH2, OH, a C1-C10 alkyl group, or —COORz (Rz is a C1-C10 alkyl group), and
- Rh is hydrogen, NH2, OH, or a C1-C5 alkyl group.
13 more elements
A compound represented by Chemical Formula 1 below or the pharmaceutically acceptable salt thereof:
- wherein the compound is at least one selected from the group consisting of Compounds 64-77, 124, 134-140, 142, and 149-155 below:
- A = CRa, B = CRb, G = CRe, D = E = L = M = CH
- Compound
- Rx
- Ra
- Rb
- Rc
- Rd
- Re
- Rf
- 64
- H
- H
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- H
- H
- 65
- H
- H
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- CH3
- H
- 66
- H
- H
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- CH2CH3
- H
- 67
- H
- CH3
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- H
- H
- 68
- H
- CH2CH3
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- H
- H
- 69
- H
- H
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- H
- CH3
- 70
- H
- H
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- CH3
- CH3
- 71
- H
- H
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- H
- H
- 72
- H
- H
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- H
- H
- 73
- H
- H
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- H
- H
- 74
- H
- H
- H
- CH2C(CH3)3
- H
- H
- 75
- H
- H
- H
- CH2C(CH3)3
- H
- H
- 76
- H
- H
- H
- CH2C(CH3)3
- COOCH2Ph
- H
- H
- 77
- H
- H
- H
- CH2C(CH3)3
- H
- H
- 124
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- H
- 134
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- H
- 135
- H
- H
- H
- CH2C(CH3)3
- COOH
- OH
- H
- 136
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- CH
- 137
- H
- H
- H
- CH2C(CH3)3
- COOH
- NH2
- H
- 138
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- NH2
- 139
- H
- H
- H
- CH2C(CH3)3
- COOH
- CH3
- H
- 140
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- CH3
- A = CRa, B = CRb, G = CRe, D = E = M = CH
- Fused ring
- Rx
- Ra
- Rb
- Rc
- Rd
- Re
- formation of J and L
- 142
- H
- H
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- H
- A = CRa, B = CRb, G = CRe, J = CRf, M = CRg, D = E = L = CH
- . . .
- Rx
- Ra
- Rb
- Rc
- Rd
- Re
- Rf
- Rg
- 149
- H
- H
- H
- CH2C(CH3)3
- COO(CH2)3CH3
- H
- H
- COO(CH2)3CH3
- 150
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- H
- OH
- 151
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- H
- NH2
- 152
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- H
- CH3
- A = CRa, B = CRb, G = CRe, J = CRf, L = CRh, D = E = L = CH
- . . .
- Rx
- Ra
- Rb
- Rc
- Rd
- Re
- Rf
- Rh
- 153
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- H
- OH
- 154
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- H
- NH2
- 155
- H
- H
- H
- CH2C(CH3)3
- COOH
- H
- H
- CH3.
279 more elements
A method of inhibiting activities of cyclophilin in a subject, the method comprising:
- administering, to a subject in need of such inhibition, an effective amount of a composition comprising a compound represented by Chemical Formula 1 below or a pharmaceutically acceptable salt thereof:
- in Chemical Formula 1,
- A is CRa,
- B is CRb,
- G is CRe,
- J is CRf,
- M is CRg,
- D, E, and L are CRh,
- Rx is H,
- Ra is hydrogen, or a C1-C5 alkyl group,
- Rb is hydrogen,
- Rc is a —CH2C(CH3)3,
- Rd is COOH, or —COOR5 (R5 is a C1-C10 alkyl group or a C3-C10 cycloalkyl group, wherein the C1-C10 alkyl group may be substituted with at least one substituent selected from the group consisting of amine, a C6-C12 aryl, a C5-C10 heterocyclic group including nitrogen as a hetero atom, and a C3-C10 cycloalkyl group),
- Re is hydrogen, NH2, OH, or a C1-C10 alkyl group,
- Rf is hydrogen, NH2, OH, or a C1-C4 alkyl group,
- Rg is hydrogen, NH2, OH, a C1-C10 alkyl group, or —COORz (Rz is a C1-C20 alkyl group), and
- Rh is hydrogen, NH2, OH, or a C1-C5 alkyl group.
14 more elements
Dependencies are inferred from the claim text.