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US 11,286,228 B2Granted
Stilbene derivative and method for preparing same
AssigneeOzchela Inc.
InventorsMin-Kyung Lee, Jin-Kak Lee, Won-Seok Han
Life of this patent
Estimating the term…
Abstract
A stilbene derivative and a method of preparing the A stilbene derivative are disclosed. The stilbene derivative is provided 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. The method of preparing a stilbene derivative includes reacting a phenylacetonitrile derivative with a benzaldehyde derivative.
Claims18
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 of Chemical Formula 1 or a pharmaceutically acceptable salt thereof:
- in Chemical Formula 1,
- A is CRa,
- B is CRb,
- G is CRe or N,
- J is CRf or N,
- M is CRg or N,
- D and E are CRh,
- L is CRh or N,
- Rx is H, CH3, CN, NH2, F, Cl, Br or I,
- wherein when Rx is H, CH3, NH2, F, Cl, Br or I,
- Ra is hydrogen, NO2, CN, OH, a C1-C5 alkyl group, a C2-C10 alkenyl group, a C1-C2 alkoxy group, —COOR1 (R1 is hydrogen or a C1-C5 alkyl group) or —OCOR2 (R2 is a C1-C5 alkyl group),
- Rb is hydrogen, a C1-C20 alkyl group, a C2-C10 alkenyl group, a C1-C10 alkoxy group, —COOR1 (R1 is hydrogen or a C1-C5 alkyl group) or —OCOR2 (R2 is a C1-C5 alkyl group),
- Rc is NO2, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a C3-C10 alkoxy group, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR3R4 (R3 is hydrogen, a C1-C20 alkyl group or a C6-C12 aryl, R4 is hydrogen, a C1-C20 alkyl group or a C6-C12 aryl, and R3 and R4 are linked to form a heterocycle, further containing at least one hetero atom), —COOR5 (R5 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group), —NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group), or —COR10 (R10 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group),
- Rd is halogen, NO2, COOH, CN, a C2-C20 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR3R4 (R3 is hydrogen, a C1-C20 alkyl or a C6-C12 aryl, R4 is hydrogen, a C1-C20 alkyl or a C6-C12 aryl, and R3 and R4 are linked to form a heterocycle, further containing at least one hetero atom), —COOR5 (R5 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —OCOR6 (R6 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group), —NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group), or COR10 (R10 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group),
- Re is hydrogen, NH2, OH, CN, a C1-C20 alkyl group, a C2-C10 alkenyl group, a C1-C10 alkoxy, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group) or —NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group),
- Rf is hydrogen, NH2, OH, NO2, a C1-C4 alkyl group, a C2-C10 alkenyl group, a C1-C4 alkoxy group, a C6-C12 aryl, a C5-C12 heterocyclic group, —NHR11 (R11 is a C1-C2 alkyl group), —COOR12 (R12 is a C1-C2 alkyl group), —OCOR13 (R13 is a C1-C2 alkyl group), or —COR14 (R14 is a C1-C2 alkyl group),
- Rg is hydrogen, NH2, OH, halogen, NO2, COOH, CN, a C1-C20 alkyl group, a C2-C10 alkenyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR3R4 (R3 is hydrogen, a C1-C20 alkyl or a C6-C12 aryl, R4 is hydrogen, a C1-C20 alkyl or a C6-C12 aryl, and R3 and R4 are linked to form a heterocycle, further containing at least one hetero atom), —COOR5 (R5 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —OCOR6 (R6 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group), —NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group), or —COR10 (R10 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group), and
- Rh is hydrogen, NH2, OH, a C1-C5 alkyl group or a C2-C10 alkenyl group,
- wherein when Rx is CN,
- Ra is hydrogen,
- Rb is hydrogen, a C1-C20 alkyl group, a C2-C10 alkenyl group, a C1-C10 alkoxy group, —COOR1 (R1 is hydrogen or a C1-C5 alkyl group) or —OCOR2 (R2 is a C1-C5 alkyl group),
- Rc is OH, NO2, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a C2-C10 alkoxy group, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR3R4 (R3 is hydrogen, a C1-C20 alkyl group or a C6-C12 aryl, R4 is hydrogen, a C1-C20 alkyl group or a C6-C12 aryl, and R3 and R4 are linked to form a heterocycle, further containing at least one hetero atom), —COOR5 (R5 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —OCOR6 (R6 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group), —NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group), or —COR10 (R10 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group, or a C5-C12 heterocyclic group),
- Rd is hydrogen, halogen, NO2, COOH, CN, a C2-C20 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR3R4 (R3 is hydrogen, a C1-C20 alkyl group or a C6-C12 aryl, R4 is hydrogen, a C1-C20 alkyl group or a C6-C12 aryl, and R3 and R4 are linked to form a heterocycle, further containing at least one hetero atom), —COOR5 (R5 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —OCOR6 (R6 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group), —NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group), or COR10 (R10 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group),
- Re is hydrogen, CN, a C2-C20 alkyl group, a C2-C10 alkenyl group, a C1-C10 alkoxy, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group) or —NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group),
- Rf is hydrogen, NH2, OH, NO2, a C1-C4 alkyl group, a C2-C10 alkenyl group, a C1-C4 alkoxy group, a C6-C12 aryl, a C5-C12 heterocyclic group, —NHR11 (R11 is a C1-C2 alkyl group), —COOR12 (R12 is a C1-C2 alkyl group), —OCOR13 (R13 is a C1-C2 alkyl group), or —COR14 (R14 is a C1-C2 alkyl group),
- Rg is hydrogen, NH2, OH, halogen, NO2, COOH, CN, a C1-C20 alkyl group, a C2-C10 alkenyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR3R4 (R3 is hydrogen, a C1-C20 alkyl or a C6-C12 aryl, R4 is hydrogen, a C1-C20 alkyl or a C6-C12 aryl, and R3 and R4 are linked to form a heterocycle, further containing at least one hetero atom), —COORS (R5 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —OCOR6 (R6 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group), -NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group), or —COR10 (R10 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group), and
- Rh is hydrogen, NH2, OH, a C1-C5 alkyl group or a C2-C10 alkenyl group, wherein when Rx is CN,
- Ra is hydrogen,
- Rb is hydrogen, a C1-C20 alkyl group, a C2-C10 alkenyl group, a C1-C10 alkoxy group, —COOR1 (R1 is hydrogen or a C1-C5 alkyl group) or —OCOR2 (R2 is a C1-C5 alkyl group),
- Rc is OH, NO2, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a C2-C10 alkoxy group, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR3R4 (R3 is hydrogen, a C1-C20 alkyl group or a C6-C12 aryl, R4 is hydrogen, a C1-C20 alkyl group or a C6-C12 aryl, and R3 and R4 are linked to form a heterocycle, further containing at least one hetero atom), —COORS (R5 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —OCOR6 (R6 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group), -NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group), or -COR10 (R10 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group, or a C5-C12 heterocyclic group),
- Rd is hydrogen, halogen, NO2, COOH, CN, a C2-C20 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR3R4 (R3 is hydrogen, a C1-C20 alkyl group or a C6-C12 aryl, R4 is hydrogen, a C1-C20 alkyl group or a C6-C12 aryl, and R3 and R4 are linked to form a heterocycle, further containing at least one hetero atom), —COOR5 (R5 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —OCOR6 (R6 is a C1-C20 alkyl group, a C6-C12 aryl or a C3-C10 cycloalkyl group), —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group), -NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group), or COR10 (R10 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group),
- Re is hydrogen, CN, a C2-C20 alkyl group, a C2-C10 alkenyl group, a C1-C10 alkoxy, a C6-C12 aryl, a C5-C12 heterocyclic group, —NR7CYR8 (Y is O or S, R7 is hydrogen or a C1-C5 alkyl group, and R8 is a C1-C20 alkyl group, a C6-C12 aryl, a C3-C10 cycloalkyl group or a C5-C12 heterocyclic group) or —NHS(O)2R9 (R9 is a C6-C12 aryl or a C5-C12 heterocyclic group),
- Rf and Rg are each hydrogen, and
- Rh is hydrogen, a C1-C5 alkyl group or a C2-C10 alkenyl group,
- wherein a hetero atom of the heterocyclic group is at least one selected from the group consisting of nitrogen, oxygen and sulfur,
- wherein the alkyl group may be substituted with at least one substituent selected from the group consisting of OH, amine, a C6-C12 aryl, a C5-C10 heterocyclic group and a C3-C10 cycloalkyl group,
- wherein the alkoxy group may be substituted with at least one substituent selected from the group consisting of halogen, a C6-C12 aryl, a C3-C10 cycloalkyl group, amine and an aminocarbonyl group,
- wherein the heterocyclic group may be substituted with at least one substituent selected from the group consisting of an alkyl group, an amine-substituted alkyl group, amine, an amide group and a carboxyl group,
- wherein the aryl may be substituted with at least one substituent selected from the group consisting of halogen, an alkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an ester group, a nitro group and an amine group,
- wherein A, B, D, E, G, J, L and M may be linked with an adjacent group to form a fused ring, and
- wherein Rd is not NO2 when Rb is CH3.
39 more elements
Dependencies are inferred from the claim text.