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US 11,148,998 B2Granted
Dimethyl-nonatetraenyl-trimethyl-cyclohexyl compounds and uses thereof
AssigneeThe Regents of the University of Michigan
InventorsJames Varani, Hollis Showalter, Andy White, Kent J. Johnson
Life of this patent
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Abstract
This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a dimethyl-nonatetraenyl-trimethyl-cyclohexyl structure useful as therapeutics for the treatment of subjects suffering from disorders characterized by abnormal proliferation and/or abnormal differentiation of cells, in particular of cells of which the growth and differentiation is sensitive to the actions of retinoids.
Claims16
A compound having Formula I:
- or a pharmacologically acceptable salt, or a hydrate, or a solvate, or prodrug, thereof;
- wherein
- R1 is CH3, CF3, C2-10 alkyl, C3-10 alkenyl, C3-10 alkynyl, all of which may be straight chain or branched, or CF3, which can be optionally substituted with up to three groups chosen independently from C1-10 alkyl, C3-10 cycloalkyl, C2-10 alkenyl C3-10 cycloalkenyl, C2-10 alkynyl, wherein all aliphatics may be straight chain or branched, halogen, hydroxy, cyano, oxo, CF3, OR4, or OR3;
- and independently;
- R2 is CH2(CO)R3, C1-10 alkyl, C3-10 alkenyl, C3-10 alkynyl, all of which may be straight chain or branched, or CF3, which can be optionally substituted with up to three groups chosen independently from C1-10 alkyl, C3-10 cycloalkyl, C2-10 alkenyl C3-10 cycloalkenyl, C2-10 alkynyl, wherein all aliphatics may be straight chain or branched, halogen, hydroxy, cyano, oxo, CF3, OR4, or OR3;
- or R1 and R2, along with the nitrogen both are bonded to form an optionally substituted ring having from 4-7 atoms, wherein the optionally substituted ring having from 4-7 atoms is selected from the group consisting of:
- R3 is C2-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, all of which may be straight chain or branched, phenyl, monocyclic or bicyclic 5-10 membered heteroaryl containing up to four heteroatoms chosen from N, O and S, C3-7 cycloalkyl, 4-7 membered heterocycloalkyl, optionally substituted with up to three groups chosen independently from C1-10 alkyl, C3-10 cycloalkyl, C2-10 alkenyl C3-10 cycloalkenyl, C2-10 alkynyl, C3-10 branched alkyl, C3-10 branched alkenyl, C4-10 branched alkynyl, C2-5 spiroalkyl, halogen, hydroxy, carboxy, cyano, oxo, or CF3;
- R4 is selected from the group consisting of:
5 more elements
A compound selected from the group consisting of:
- or a pharmaceutically acceptable salt, or solvate, or hydrate or prodrug thereof.
Dependencies are inferred from the claim text.