Bicyclic compounds
Inventors
Vendeville, Sandrine • Raboisson, Pierre Jean-Marie Bernard • McGowan, David
Assignees
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Publication Number
US-11952374-B2
Publication Date
2024-04-09
Expiration Date
Abstract
Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating diseases and/or conditions with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.
Core Innovation
The invention relates to a compound of Formula (I), or a pharmaceutically acceptable salt thereof, where n is 1 and Z1 is —C(=O)—. The core scaffold defines R4, R5, R6 and R7 each as hydrogen, and R1 is selected from the group consisting of R2 and R3, where R2 and R3 are independently selected from hydrogen and an unsubstituted C1-4 alkyl.
R8 is selected from the group consisting of an optionally substituted monocyclic heteroaryl and —NR14A R14B. R14A is defined as a monocyclic C3-6 cycloalkyl optionally substituted with one or two halogens, a monocyclic C3-6 cycloalkyl(C1-4 alkyl) optionally substituted with one or two halogens, an optionally substituted 4-6 member monocyclic heterocyclyl, or an optionally substituted monocyclic 4- to 6-membered heterocyclyl(C1-4 alkyl), and R14B is selected from an optionally substituted aryl and an optionally substituted aryl(C1-4 alkyl).
R9 is selected as a substituted phenyl, a substituted monocyclic heteroaryl, or a substituted fused-bicyclic heteroaryl, wherein the substituted aromatic/heteroaromatic group is substituted with one or more substituents selected from halogen, an unsubstituted C1-4 alkyl, an unsubstituted C1-4 haloalkyl, an unsubstituted C1-4 alkoxy, an optionally substituted monocyclic heteroaryl, an optionally substituted monocyclic heterocyclyl, amino, a mono-substituted amine, a di-substituted amine and —C(=O)NHR15. R15 is hydrogen, an unsubstituted C1-6 alkyl, an optionally substituted C2-6 alkenyl, an optionally substituted C1-6 alkynyl, or an optionally substituted C3-6 monocyclic cycloalkyl.
Claims Coverage
The provided material identifies one independent claim for a compound of Formula (I) or a pharmaceutically acceptable salt thereof with n = 1 and Z1 = —C(=O)—. The claim presents five merged inventive feature groupings covering the fixed core scaffold, R1 and R2/R3 selection, R8 as —NR14A R14B or optionally substituted monocyclic heteroaryl, R9 as a substituted aryl/heteroaryl framework, and the defined R14A, R14B, and R15 substituent classes.
Formula (I) compound with fixed core constraints
A compound of Formula (I), or a pharmaceutically acceptable salt thereof, having n = 1 and Z1 = —C(=O)—, with R4, R5, R6 and R7 each hydrogen.
R1 selection from R2 and R3
R1 is selected from the group consisting of R2 and R3, where R2 and R3 are independently selected from hydrogen and an unsubstituted C1-4 alkyl.
R8 as optionally substituted monocyclic heteroaryl or —NR14A R14B
R8 is selected from the group consisting of an optionally substituted monocyclic heteroaryl and —NR14A R14B.
R9 as substituted phenyl, monocyclic heteroaryl, or fused-bicyclic heteroaryl
R9 is a substituted phenyl, a substituted monocyclic heteroaryl, or a substituted fused-bicyclic heteroaryl, substituted with one or more substituents selected from halogen, an unsubstituted C1-4 alkyl, an unsubstituted C1-4 haloalkyl, an unsubstituted C1-4 alkoxy, an optionally substituted monocyclic heteroaryl, an optionally substituted monocyclic heterocyclyl, amino, a mono-substituted amine, a di-substituted amine, and —C(=O)NHR15.
Defined R14A, R14B, and R15 substituent classes
R14A is a monocyclic C3-6 cycloalkyl optionally substituted with one or two halogens, a monocyclic C3-6 cycloalkyl(C1-4 alkyl) optionally substituted with one or two halogens, an optionally substituted 4-6 member monocyclic heterocyclyl, or an optionally substituted monocyclic 4- to 6-membered heterocyclyl(C1-4 alkyl). R14B is selected from an optionally substituted aryl and an optionally substituted aryl(C1-4 alkyl). R15 is hydrogen, an unsubstituted C1-6 alkyl, an optionally substituted C2-6 alkenyl, an optionally substituted C1-6 alkynyl, or an optionally substituted C3-6 monocyclic cycloalkyl.
Independent claim centers on a Formula (I) compound family with n = 1 and Z1 = —C(=O)—, together with constrained selections for R1, R8, R9, R14A, R14B, and R15.
Stated Advantages
Provides hepatitis B treatment based on the method claim and HBV antiviral evaluation context (therapeutic window based on EC50/CC50 classification is reported).
Documented Applications
HBV antiviral evaluation using HepG2.117 cells with HBV DNA quantification by qPCR and cell viability measurement, including potency/cytotoxicity classification and therapeutic window assessment for multiple Formula (I) compounds.
Treatment application stated as a method for treating hepatitis B by administering an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt, to a subject in need.
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