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US 8,569,287 B2Granted
Azepino[4,5-B]indoles and methods of use
AssigneeMedivation Technologies, Inc.
InventorsDavid T. Hung, Andrew Asher Protter, Rajendra Parasmal Jain, Sarvajit Chakravarty
Life of this patent
Estimating the term…
Abstract
This disclosure relates to new azepino[4,5-b]indole compounds that may be used to modulate a histamine receptor in an individual. Novel compounds are described, including new 1,2,3,4,5,6-tetrahydroazepino[4,5-b]indoles. Pharmaceutical compositions are also provided.
Claims30
A compound of formula (I):
- wherein:
- R1 is H, hydroxyl, nitro, cyano, halo, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C2-C8 alkynyl, perhaloalkyl, acyl, acyloxy, carbonylalkoxy, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkyl, C1-C8 perhaloalkoxy, alkoxy, aryloxy, carboxyl, thiol, thioalkyl, substituted or unsubstituted amino, acylamino, aminoacyl, aminocarbonylamino, aminocarbonyloxy, aminosulfonyl, sulfonylamino, sulfonyl, alkylsulfonylamino, or carbonylalkylenealkoxy;
- each R2a, R2b, R3a and R3b is independently H, hydroxyl, nitro, cyano, halo, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C2-C8 alkynyl, perhaloalkyl, acyl, acyloxy, carbonylalkoxy, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkyl, C1-C8 perhaloalkoxy, alkoxy, aryloxy, carboxyl, thiol, thioalkyl, substituted or unsubstituted amino, acylamino, aminoacyl, aminocarbonylamino, aminocarbonyloxy, aminosulfonyl, sulfonylamino, sulfonyl, alkylsulfonylamino, or carbonylalkylenealkoxy, or is taken together with the carbon to which it is attached and a geminal R2 or R3 to form a cycloalkyl moiety or a carbonyl moiety;
- each R10a, R10b, R11a and R11b is independently H, hydroxyl, nitro, cyano, halo, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C2-C8 alkynyl, perhaloalkyl, acyl, acyloxy, carbonylalkoxy, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkyl, C1-C8 perhaloalkoxy, alkoxy, aryloxy, carboxyl, thiol, thioalkyl, substituted amino, acylamino, aminoacyl, aminocarbonylamino, aminocarbonyloxy, aminosulfonyl, sulfonylamino, sulfonyl, alkylsulfonylamino, or carbonylalkylenealkoxy, or is taken together with the carbon to which it is attached and a geminal R10 or R11 to form a cycloalkyl moiety or a carbonyl moiety;
- each X7, X8, X9 and X10 is independently N or CR4;
- each R4 is independently H, hydroxyl, nitro, cyano, halo, C1-C8 perhaloalkyl, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C2-C8 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, C1-C8 perhaloalkoxy, C1-C8 alkoxy, aryloxy, carboxyl, carbonylalkoxy, thiol, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aralkyl, thioalkyl, substituted or unsubstituted amino, acylamino, aminoacyl, aminocarbonylamino, aminocarbonyloxy, aminosulfonyl, sulfonylamino, sulfonyl, carbonylalkylenealkoxy, alkylsulfonylamino or acyl;
- m is 1;
- q is 0;
- each R8c, R8d, R8e and R8f is independently H, hydroxyl, alkoxy, halo, C1-C8 perhaloalkyl, carboxy, carbonylalkoxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, or is taken together with the carbon to which it is attached and a geminal R8 to form a cycloalkyl moiety;
- and
- Q is a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl;
- provided that (i) at least one of X7, X8, X9 and X10 is N, or (ii) at least one of R8c, R8d, R8e and R8f is hydroxyl,
- or a salt thereof.
10 more elements
A compound of formula (I):
- wherein:
- R1 is CH3, —CH2CH2F, —CH2CF3, or —CH2CH2C(CH3)2OH;
- each R2a, R2b, R3a, R3b, R10a, R10b, R11a and R11b is H;
- each X7, X8, X9 and X10 is CR4;
- each R4 is independently H, CH3, CF3, Cl, F, or —NHCH3;
- m is 1;
- q is 0;
- each R8c, R8d, R8e and R8f is independently H, hydroxyl, unsubstituted C1-C4 alkyl or is taken together with the carbon to which it is attached and a geminal R8 to form a cycloalkyl moiety, provided that at least one of R8c, R8d, R8e and R8f is other than H;
- and
- Q is 3-pyridyl or 4-pyridyl, each of which can be substituted with one, two or three moieties selected from the group consisting of C1-C4 alkyl, halo, perhaloalkyl and perhaloalkoxy;
- or a salt thereof.
8 more elements
A compound of formula (I):
- wherein:
- R1 is CH3, —CH2CH2F, —CH2CF3, or —CH2CH2C(CH3)2OH;
- each R2a, R2b, R3a, R3b, R10a, R10b, R11a and R11b is H;
- X7, X8 and X10 are each CR4, wherein R4 is H;
- X9 is CR4 where R4 is CH3, Cl, or F;
- and
- m is 1;
- q is 0;
- each R8c, R8d, R8e and R8f is independently H, hydroxyl, unsubstituted C1-C4 alkyl or is taken together with the carbon to which it is attached and a geminal R8 to form a cycloalkyl moiety, provided that at least one of R8c, R8d, R8e and R8f is other than H;
- and
- Q is phenyl which can be substituted with one, two or three moieties selected from the group consisting of C1-C4 alkyl, halo, perhaloalkyl and perhaloalkoxy;
- or a salt thereof.
9 more elements
Dependencies are inferred from the claim text.