CD151 inhibitors
Inventors
Feutrill, John Thomas • Garnier, Jean-Marc • FRAUMAN, Albert George
Assignees
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Publication Number
US-12215112-B2
Publication Date
2025-02-04
Expiration Date
Abstract
The present invention relates to compounds of formula (I) that have the ability to inhibit CD151.
Core Innovation
The disclosure provides compounds of Formula (I), including pyrazolo[1,5-a]pyrimidine-2-carboxamide compounds and related substituted heteroaromatic scaffolds with multiple variable substituents selected through the R-group definitions. The compounds include pharmaceutically acceptable salts, and the examples retain the core scaffold while varying aryl, heteroaryl, and amide side-chain substituents.
The disclosed compounds include a pyrazolo[1,5-a]pyrimidine-2-carboxamide core with a 7-(1H-pyrazol-4-yl) motif and variable substitution on the carboxamide nitrogen side chain. Example compounds and analogs are reported with substitutions such as hydroxy, methoxy, halogen, cyano, difluoromethoxy, dimethylamino, methylsulfonyl, piperazinyl phenyl, benzyl(methyl)amino, isoindolinyl, and pyrazolyl groups, while maintaining the same core scaffold.
The disclosure also describes substituted pyrazolo[1,5-a]pyrimidine carboxamide and acid derivatives. In the broader Formula (I) definitions, R7 and R8 can independently vary or, together with the attached nitrogen atom, form an optionally substituted C2-C12 heterocyclic group.
Claims Coverage
The independent claim covers Formula (I) compounds with broad, independently selectable substituent sets at R1-R8 and includes pharmaceutically acceptable salts. The claim family centers on the core scaffold and the option for R7 and R8 to form an optionally substituted C2-C12 heterocyclic group with the attached nitrogen atom, with dependent claims refining substituent selections and heterocycle definitions.
Formula (I) compound with variable R1-R8 substituents
A compound of Formula (I) wherein R1, R2, and R3 are each independently selected from H and C1-C12 alkyl; R4 is selected from H and C1-C12 alkyl; R5 is selected from H, optionally substituted C6-C18 aryl, optionally substituted C1-C18 heteroaryl, optionally substituted C6-C18 arylC1-C12 alkyl, and optionally substituted C1-C18 heteroarylC1-C12 alkyl; R6 is selected from H, C1-C12 alkyl, C3-C6 cycloalkyl, and C1-C5 heterocycloalkyl; and R7 and R8 are selected from H and C1-C12 alkyl or, when taken together with the nitrogen atom to which they are attached, form an optionally substituted C2-C12 heterocyclic group; or a pharmaceutically acceptable salt thereof.
7-(1H-pyrazol-4-yl) pyrazolo[1,5-a]pyrimidine-2-carboxamide scaffold
A compound of Formula (I) in which the structure includes the pyrazolo[1,5-a]pyrimidine-2-carboxamide scaffold with a 7-(1H-pyrazol-4-yl) motif, with substituents defined by R1 through R8 under the claim constraints.
Optionally substituted C2-C12 heterocyclic group from R7 and R8
R7 and R8, when taken together with the nitrogen atom to which they are attached, form an optionally substituted C2-C12 heterocyclic group.
Pharmaceutically acceptable salts of the Formula (I) compound
The compound includes a pharmaceutically acceptable salt thereof.
C2-C12 heterocycle defined by an explicit structural formula with expanded substituent set
A compound according to the dependent refinements in which the C2-C12 heterocyclic group is defined by a specified structural formula and each RD substituent is independently selected from a listed set of groups including H, halogen, OH, NO2, CN, SH, NH2, CF3, OCF3, optionally substituted C1-C12 alkyl and haloalkyl, and various optionally substituted aryl, heteroaryl, alkyloxy, heteroalkyloxy, cycloalkyl/cycloalkenyl, heterocycloalkyl/heterocycloalkenyl, amino, SR9, SO3H, SO2NR9R10, COR9, COOH, COOR9, CONR9R10, NR9COR10, NR9SO2R10, NR9CONR9R10, and acyl.
Overall, the claims cover Formula (I) compounds with defined substitution ranges at R1-R8, including the option for R7 and R8 to jointly form an optionally substituted C2-C12 heterocyclic group with the attached nitrogen atom, and include pharmaceutically acceptable salts. Dependent claims further narrow the scope by fixing particular substituent choices and defining the heterocyclic portion through an explicit structural-form definition with a specified substituent list.
Stated Advantages
Not explicitly described in patent.
Documented Applications
PC3 prostate cancer cell invasion/proliferation measurements using xCELLigence RTCA/CIM plates with Matrigel, with compound-specific IC50 values reported for listed example compounds.
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