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US 10,519,113 B2Granted
Kinase inhibitor compounds, compositions, and methods of treating cancer
AssigneeIcahn School of Medicine at Mount Sinai
InventorsArvin C. Dar, Ross L. Cagan, Alex P. Scopton, Masahiro Sonoshita
Life of this patent
Estimating the term…
Abstract
The present invention relates to a compound having the structure of formula (I) or a stereoisomer, pharmaceutically acceptable salt, oxide, or solvate thereof, where X, Y, Z, R, R1, R2, R3, R4, R5, and R6 are as described herein. The present invention also relates to compositions containing the compound having the structure of formula (I), and a method of treating cancer in a subject.
Claims17
A compound of formula (I) having the following structure:
- or a stereoisomer, pharmaceutically acceptable salt, oxide, or solvate thereof, wherein
- R is selected from the group consisting of C1-6 alkyl, C1-6 alkoxy, —N(C1-6 alkyl)2, C3-6 cycloalkyl, aryl, heteroaryl, and heterocyclyl, wherein C1-6 alkyl, C3-6 cycloalkyl, aryl, heteroaryl, and heterocyclyl can be optionally substituted n times with R13;
- R1 is H;
- R2 is H;
- or R1 and R2 combine with the phenyl ring to which they are attached to form
- (a naphthyl group);
- R3 is H or halogen;
- R4 is H, halogen, or C1-C6 alkyl;
- R5 is H, halogen, or C1-C6 alkyl;
- R6 is C1-C6 alkyl;
- X is optional and, if present, is NH;
- Y is
- Z is C(R12) or N;
- R7 is H or Me;
- R8 is H or Me;
- or R7 and R8 are taken together with the carbon atom to which they are attached to form
- R9 is H, C1-6 alkyl, C3-6 cycloalkyl, allyl, —CN, or
- R10 is H, C1-6 alkyl, or C3-6 cycloalkyl;
- R11 is H, C1-6 alkyl, or C3-6 cycloalkyl;
- R12 is H, halogen, or C1-C6 alkyl;
- R13 is selected independently at each occurrence thereof from the group consisting of H, halogen, C1-C6 alkyl, CH2F, CHF2, CClF2, CBrF2, CIF2, CF3, C2F5, C3F7, C4F9, OCF3 and heterocyclyl;
- and
- n is 1 to 5;
- with the proviso that when
- i) R1 is H, R2 is H, R3 is H, R4 is H, R5 is H, R6 is CH3, Z is CH, X is NH, and Y is
- R cannot be
- ii) R1 is H, R2 is H, R3 is H, R4 is H, R5 is H, R6 is CH3, Z is CH, X is absent, and Y is
- R cannot be
- iii) R1 is H, R2 is H, R3 is H, R4 is H, R5 is H, R6 is CH3, Z is CH, Y is
- and n is 2, R cannot be
- iv) R1 is H, R2 is H, R3 is F, R4 is H, R5 is H, R6 is CH3, Z is CH, X is NH, Y is
- and n is 2, R cannot be
- v) R1 is H, R2 is H, R3 is H, R4 is H, R5 is H, R6 is CH3, Z is CH, X is absent, and Y is
- R cannot be
- and
- vi) R1 is H, R2 is H, R3 is H, R4 is H, R5 is H, R6 is CH3, Z is CH, X is NH, and Y is
- R cannot be
34 more elements
A method of treating cancer in a subject, said method comprising:
- administering to a subject a compound of formula (I) having the following structure:
- or a stereoisomer, pharmaceutically acceptable salt, oxide, or solvate thereof, wherein
- R is selected from the group consisting of C1-6 alkyl, C1-6 alkoxy, —N(C1-6alkyl)2, C3-6 cycloalkyl, aryl, heteroaryl, and heterocyclyl, wherein C1-6 alkyl, C3-6 cycloalkyl, aryl, heteroaryl, and heterocyclyl can be optionally substituted n times with R13;
- R1 is H;
- R2 is H;
- or R1 and R2 combine with the phenyl ring to which they are attached to form
- (a naphthyl group);
- R3 is H or halogen;
- R4 is H, halogen, or C1-C6 alkyl;
- R5 is H, halogen, or C1-C6 alkyl;
- R6 is C1-C6 alkyl;
- X is optional and, if present, is NH;
- Y is
- Z is C(R12) or N;
- R7 is H or Me;
- R8 is H or Me;
- or R7 and R8 are taken together with the carbon atom to which they are attached to form
- R9 is H, C1-6 alkyl, C3-6 cycloalkyl, allyl, —CN, or
- R10 is H, C1-6 alkyl, or C3-6 cycloalkyl;
- R11 is H, C1-6 alkyl, or C3-6 cycloalkyl;
- R12 is H, halogen, or C1-C6 alkyl;
- R13 is selected independently at each occurrence thereof from the group consisting of H, halogen, C1-C6 alkyl, CH2F, CHF2, CClF2, CBrF2, CIF2, CF3, C2F5, C3F7, C4F9, OCF3 and heterocyclyl;
- and
- n is 1 to 5;
- with the proviso that when
- i) R1 is H, R2 is H, R3 is H, R4 is H, R5 is H, R6 is CH3, Z is CH, X is NH, and Y is
- R cannot be
- ii) R1 is H, R2 is H, R3 is H, R4 is H, R5 is H, R6 is CH3, Z is CH, X is absent, and Y is
- R cannot be
- iii) R1 is H, R2 is H, R3 is H, R4 is H, R5 is H, R6 is CH3, Z is CH, Y is
- and n is 2, R cannot be
- iv) R1 is H, R2 is H, R3 is F, R4 is H, R5 is H, R6 is CH3, Z is CH, X is NH, Y is
- and n is 2, R cannot be
- v) R1 is H, R2 is H, R3 is H, R4 is H, R5 is H, R6 is CH3, Z is CH, X is absent, and Y is
- R cannot be
- and
- vi) R1 is H, R2 is H, R3 is H, R4 is H, R5 is H, R6 is CH3, Z is CH, X is NH, and Y is
- R cannot be
35 more elements
Dependencies are inferred from the claim text.