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US 2017/0253581 A1Published application
SUBSTITUTED HETEROCYCLES AS c-MYC TARGETING AGENTS
AssigneeNorthwestern University
InventorsGary E. Schiltz, Rama K. Mishra, Huiying Han, Sarki A. Abdulkadir
Life of this patent
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Abstract
Disclosed are substituted heterocycles compounds including substituted pyrazoles, substituted pyrimidines, and substitute triazoles. The substituted heterocycles disclosed herein are shown to be useful in inhibiting c-MYC and may be utilized as therapeutics for treating cancer and cell proliferative disorders.
Claims19
A compound having a formula I:
- wherein
- R1 is hydrogen or R1 is an aryl group, a benzyl group, a heteroaryl group, cycloalkyl, or cycloheteroalkyl, optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- n is 0, 1, or 2;
- p is 0 or 1;
- X is O or NH, or R1(CH2)n(X)p— is N-piperazinyl optionally N-substituted with alkyl;
- m is 0 or 1;
- R2 is hydrogen or halo, or R2 is an aryl group, a benzyl group, a heteroaryl group, cycloalkyl, or cycloheteroalkyl, optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- R3 is hydrogen, alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, benzyl, hydroxyl, halo, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- R4 is hydrogen, amino, alkyl, or R4 is aryl or benzyl optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl (e.g., phenyl), hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, alkoxycarbonyl, aryloxy, and alkylaryloxy;
- R5 is alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxyl, or halo;
- R6 is hydrogen, amino, alkyl, or R6 is aryl or benzyl optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, alkoxycarbonyl, aryloxy, and alkylaryloxy, or R6 and R5 together form a ring structure having a formula
- R7 is hydrogen or alkyl;
- with the proviso that at least one of R4 and R6 is hydrogen;
- with the proviso that if R5 is hydrogen, then p is 1 and m is 1;
- and
- with the proviso that if R1(CH2)n(X)p— is hydrogen, hydroxyl, or alkyl, and R5 is hydroxyl, then m is 1, or at least one of R2 and R3 is not hydrogen.
13 more elements
A compound having a formula II:
- wherein
- Y is C or N;
- R1 is hydrogen or an aryl group, a benzyl group, a heteroaryl group, cycloalkyl, or cycloheteroalkyl, optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- n is 0, 1, or 2;
- p is 0 or 1;
- X is O or NH, or R1(CH2)n(X)p— is N-piperazinyl optionally N-substituted with alkyl;
- m is 0 or 1;
- R2 is hydrogen or halo, or R2 is an aryl group, a benzyl group, a heteroaryl group, cycloalkyl, or cycloheteroalkyl, optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- R3 is hydrogen, alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, benzyl, hydroxyl, halo, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- R4 is hydrogen, amino, alkyl, aryl, or benzyl optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, alkoxycarbonyl, aryloxy, and alkylaryloxy;
- R5 is alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxyl, and halo;
- R6 is hydrogen, amino, alkyl, aryl, or benzyl optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, alkoxycarbonyl, aryloxy, and alkylaryloxy.
9 more elements
A compound having a formula III:
- wherein:
- R1 is hydrogen or an aryl group, a benzyl group, a heteroaryl group, cycloalkyl, or cycloheteroalkyl, optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- n is 0, 1, or 2;
- p is 0 or 1;
- X is O or NH, or R1(CH2)n(X)p— is N-piperazinyl optionally N-substituted with alkyl;
- m is 0 or 1;
- R2 is hydrogen or halo, or R2 is an aryl group, a benzyl group, a heteroaryl group, cycloalkyl, or cycloheteroalkyl, optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- R4 is hydrogen, amino, alkyl, aryl, or benzyl optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, alkoxycarbonyl, aryloxy, and alkylaryloxy;
- R5 is alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxyl, and halo.
6 more elements
A compound having a formula IV:
- wherein:
- R1 is hydrogen or an aryl group, a benzyl group, a heteroaryl group, cycloalkyl, or cycloheteroalkyl, optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- n is 0, 1, or 2;
- p is 0 or 1;
- X is O or NH, or R1(CH2)n(X)p— is N-piperazinyl optionally N-substituted with alkyl;
- Y is C or N;
- Z is C or N;
- m is 0 or 1;
- R2 is hydrogen or halo, or R2 is an aryl group, a benzyl group, a heteroaryl group, cycloalkyl, or cycloheteroalkyl, optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- R4 is hydrogen, amino, alkyl, aryl, or benzyl optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, alkoxycarbonyl, aryloxy, and alkylaryloxy;
- R5 is alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxyl, and halo.
8 more elements
A compound having a formula V:
- wherein:
- R1 is hydrogen or an aryl group, a benzyl group, a heteroaryl group, cycloalkyl, or cycloheteroalkyl, optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, aryl, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl;
- n is 0, 1, or 2;
- p is 0 or 1;
- X is O or NH, or R1(CH2)n(X)p— is N-piperazinyl optionally N-substituted with alkyl;
- m is 0 or 1;
- R2 is hydrogen or halo, or R2 is an aryl group, a benzyl group, a heteroaryl group, cycloalkyl, or cycloheteroalkyl, optionally substituted at one or more ring positions with one or more of alkyl, alkoxy, haloalkyl, haloalkoxy, hydroxyl, halo, cyano, amido, hydrazonyl, carbonyl, carboxyl, and alkoxycarbonyl.
4 more elements
Dependencies are inferred from the claim text.