US 9,174,979 B2 · Phenanthroindolizidine compound and NFκB inhibitor containing same as active ingredient

Abstract

A novel compound having an excellent NFκB inhibitory effect is provided and specifically disclosed is a compound represented by the following formula (1) or a salt thereof: wherein, R1 represents a hydrogen atom, a lower alkyl group, a lower alkyloxy group, or a halogen atom; R2 represents a hydroxyl group, or a lower alkyloxy group; R3 represents a hydrogen atom, a lower alkyl group, or a halogen atom; R4 represents a hydrogen atom or a lower alkyloxy group; R5 represents a hydrogen atom, a lower alkyloxy group, a halogen atom, a hydroxyl group, or a methylenedioxy group formed together with R6 or an isopropylidenedioxy group formed together with R6; R6 represents a hydrogen atom, a lower alkyloxy group, or a methylenedioxy group formed together with R5 or an isopropylidenedioxy group formed together with R5; R7 represents a hydrogen atom or a lower alkyl group; and R8 represents a hydrogen atom, a hydroxyl group, an amino group, or a lower alkylcarbonyloxy group (excluding the case where R1, R3, R4 and R7 are hydrogen atoms, R2 and R8 are hydroxyl groups, and R5 and R6 are methoxy groups).

A compound represented by formula (1) or a salt thereof:

wherein
R1 represents a hydrogen atom, a lower alkyl group, a lower alkyloxy group, or a halogen atom;
R2 represents a hydroxyl group, or a lower alkyloxy group;
R3 represents a hydrogen atom, a lower alkyl group, or a halogen atom;
R4 represents a hydrogen atom or a lower alkyloxy group;
R5 represents a hydrogen atom, a lower alkyloxy group, a halogen atom, a hydroxyl group, or a methylenedioxy group formed together with R6, or an isopropylidenedioxy group formed together with R6;
R6 represents a hydrogen atom, a lower alkyloxy group, or a methylenedioxy group formed together with R5, or an isopropylidenedioxy group formed together with R5;
R7 represents a hydrogen atom or a lower alkyl group;
and
R8 represents a hydrogen atom, a hydroxyl group, or an amino group;
provided that the following cases are excluded:
(A) the case where R1, R3, R4, and R7 are hydrogen atoms, R2 and R8 are hydroxyl groups, and R5 and R6 are methoxy groups;
(B) the case where R1, R3, R4, and R7 are hydrogen atoms, R2, R5, and R6 are methoxy groups, and R8 is a hydroxyl group;
(C) the case where R1, R3, R4, R7, and R8 are hydrogen atoms and R2, R5, and R6 are methoxy groups;
(D) the case where R1, R3, R4, and R7 are hydrogen atoms, R2, R5, and R8 are hydroxyl groups, and R6 is a methoxy group;
(E) the case where R1, R3, R4, and R7 are hydrogen atoms, R2 and R6 are methoxy groups, and R5 and R8 are hydroxyl groups;
(F) the case where R1, R3, R4, R7, and R8 are hydrogen atoms, R2 and R6 are methoxy groups, and R5 is a hydroxyl group;
(G) the case where R1, R2, R5, and R6 are methoxy groups and R3, R4, R7, and R8 are hydrogen atoms;
(H) the case where R1, R2, R4, and R5 are methoxy groups and R3, R6, R7, and R8 are hydrogen atoms;
(I) the case where R1, R2, R5, and R6 are methoxy groups, R3, R4, and R7 are hydrogen atoms, and R8 is a hydroxyl group;
(J) the case where R1 and R2 are methoxy groups, R3, R4, R6, R7, and R8 are hydrogen atoms, and R5 is a hydroxyl group;
(K) the case where R1, R2, and R5 are methoxy groups, and R3, R4, R6, R7, and R8 are hydrogen atoms;
(L) the case where R1, R2, and R5 are methoxy groups, R3, R4, R6, and R7 are hydrogen atoms, and R8 is a hydroxyl group;
(M) the case where R1, R2, and R5 are methoxy groups, R3, R4, R6, and R8 are hydrogen atoms, and R7 is a methyl group;
(N) the case where R1, R2, and R5 are methoxy groups, R3, R4, and R6 are hydrogen atoms, R7 is a methyl group, and R8 is a hydroxyl group;
(O) the case where R1, R2, and R6 are methoxy groups, R3, R4, R7, and R8 are hydrogen atoms, and R5 is a hydroxyl group;
(P) the case where R1, R2, and R4 are methoxy groups, R3, R6, R7, and R8 are hydrogen atoms, and R5 is a hydroxyl group;
(Q) the case where R1, R5, and R6 are methoxy groups, R2 and R8 are hydroxyl groups, and R3, R4, and R7 are hydrogen atoms;
(R) the case where R1 is an isopropyloxy group, R2 and R5 are methoxy groups, and R3, R4, R6, R7 and R8 are hydrogen atoms;
(S) the case where R1 and R5 are methoxy groups, R2 is an isopropyloxy group, and R3, R4, R6, R7 and R8 are hydrogen atoms;
(T) the case where R1 and R2 are methoxy groups, R3, R4, R6, R7, and R8 are hydrogen atoms, and R5 is an isopropyloxy group;
(U) the case where R1 and R5 are methoxy groups, R2 is a hydroxyl group, and R3, R4, R6, R7, and R8 are hydrogen atoms;
(V) the case where R1 and R2 are methoxy groups, and R3, R4, R5, R6, R7, and R8 are hydrogen atoms;
(AE) the case where R1, R3, R4, and R8 are hydrogen atoms, R2, R5, and R6 are methoxy groups, and R7 is a methyl group;
(AH) the case where R1, R2, R4, and R5 are methoxy;
R3, R6, and R7 are hydrogen atoms;
and R8 is a hydroxyl group;
and
(AI) the case where R1, R5, and R6 are methoxy, R2 is a hydroxyl, and R3, R4, R7, and R8 are hydrogen.

36 more elements

Phenanthroindolizidine compound and NFκB inhibitor containing same as active ingredient

Life of this patent

Phenanthroindolizidine compound and NFκB inhibitor containing same as active ingredient

Life of this patent

Abstract

Claims24