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Publication Number
US-11325940-B2
Publication Date
2022-05-10
Expiration Date
Abstract
Chemical entities that are novel compounds, pharmaceutical compositions and methods of treatment of cancer are described.
Core Innovation
The invention provides stereochemically defined steroid-like chemical entities having a cyclopenta[a]phenanthrene framework and a 2-oxo-2H-pyran or 2-oxo-2H-pyranone moiety, including 14-hydroxy group and 10,13-dimethyl substitution with defined stereochemistry across the hexadecahydro cyclopenta[a]phenanthrene scaffold. The disclosed embodiments include Formula I, Ia–Il, Ik, and Ii, with variable N-substituted side chains and pharmaceutically acceptable salts.
The chemical entities include morpholine-4-carboxamide, piperazine-1-carboxamide, pyrrolidine carboxamide, urea derivatives, acetamide derivatives, methanesulfonamide, carbamate variants, and related piperazinyl or pyrrolidine substitutions. The description presents these as purified chemical compounds with characterized data for select compounds, including LRMS and 1H NMR chemical shift values.
The disclosure further includes pharmaceutical compositions comprising at least one Formula I chemical entity together with a carrier, packaged compositions including the pharmaceutical composition and instructions, and methods of treating cancer by administering a therapeutically effective amount of at least one Formula I chemical entity to a subject in need. The compounds are also described for use in treating cancers across many tissue types, including lung cancer, and for ameliorating symptoms or slowing progression of lung cancer.
Claims Coverage
The consolidated claim coverage includes multiple independent claim concepts: compound claims directed to defined groups of stereochemically specified steroid-like compounds and their pharmaceutically acceptable salts, plus claims to pharmaceutical composition, packaged composition, and therapeutic administration. The inventive features focus on the steroid-like cyclopenta[a]phenanthrene core with a fused 2-oxo-2H-pyran / 2-oxo-2H-pyranone moiety, 14-hydroxy and 10,13-dimethyl substitution, and defined N-linked functionalization.
Stereochemically defined steroid-like cyclopenta[a]phenanthrene core with fused 2-oxo-2H-pyran moiety
A compound selected from specified group members that contain a cyclopenta[a]phenanthrene steroid-like core bearing stereochemically defined substituents and a 17-(2-oxo-2H-pyran-5-yl) substituent or related 2-oxo-2H-pyranone embodiments, with the specified hexadecahydro scaffold.
N-substituted side-chain functionalized as carboxamide, urea, acetamide, carbamate, or methanesulfonamide
The N-linked side-chain is specified with morpholine-4-carboxamide, piperazine-1-carboxamide, pyrrolidine carboxamide, urea derivatives, acetamide derivatives, methanesulfonamide, and carbamate variants, including related piperazinyl or pyrrolidine substitutions.
14-hydroxy and 10,13-dimethyl substituted steroid-like compound group
A compound selected from a group consisting of stereochemically defined steroid-like molecules having the specified cyclopenta[a]phenanthrene scaffold with 14-hydroxy and 10,13-dimethyl substitution, and the named stereochemical configurations, or a pharmaceutically acceptable salt thereof.
Pharmaceutically acceptable salts
The selected compounds are also covered as pharmaceutically acceptable salts.
Pharmaceutical composition
A pharmaceutical composition comprising the compound and a carrier.
Packaged pharmaceutical composition with instructions
A packaged composition comprising the pharmaceutical composition and instructions.
Method of treating cancer by administration
A method for treating cancer comprising administering a therapeutically effective amount of at least one compound, or a pharmaceutically acceptable salt thereof, to a subject in need.
Method for ameliorating symptoms or slowing progression of lung cancer
A method for ameliorating symptoms or slowing progression of lung cancer by administering a therapeutically effective amount of the compound or its pharmaceutically acceptable salt to a subject in need.
The independent claim coverage is anchored by defined groups of stereochemically specified steroid-like compounds that incorporate a fused 2-oxo-2H-pyran / 2-oxo-2H-pyranone motif, 14-hydroxy and 10,13-dimethyl substitution, and N-linked carboxamide, urea, acetamide, carbamate, methanesulfonamide, and related piperazinyl or pyrrolidine variants, with coverage extending to pharmaceutically acceptable salts, pharmaceutical compositions, packaged compositions, and cancer-treatment methods, including lung cancer.
Stated Advantages
Ameliorating symptoms or slowing progression of lung cancer.
Treating cancers across many tissue types, including lung cancer.
Documented Applications
A method for ameliorating symptoms or slowing progression of lung cancer by administering a therapeutically effective amount of the compound or its pharmaceutically acceptable salt to a subject in need.
Use for treating cancers across many tissue types, including lung cancer.
Pharmaceutical compositions comprising the compound and a carrier.
Packaged compositions comprising the pharmaceutical composition and instructions.
Methods of treating cancer by administering a therapeutically effective amount of at least one compound, or a pharmaceutically acceptable salt thereof, to a subject in need.
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