Heteroaromatic compounds having activity against RSV
Inventors
Lançois, David Francis Alain • GUILLEMONT, Jérome Émile Georges • Raboisson, Pierre Jean-Marie Bernard • RIGAUX, Peter • Michaut, Antoine Benjamin • QUATREVAUX, Sabrina Dany France • CHAO, Sovy • Roymans, Dirk André Emmy
Assignees
Janssen Pharmaceutica NV • Janssen Cilag SAS • Novalix SAS • Janssen Sciences Ireland ULC
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Publication Number
US-11708369-B2
Publication Date
2023-07-25
Expiration Date
Abstract
The invention concerns compounds of formula (I) having antiviral activity, in particular, having an inhibitory activity on the replication of the respiratory syncytial virus (RSV). The invention further concerns pharmaceutical compositions comprising these compounds and the compounds for use in the treatment of respiratory syncytial virus infection.
Core Innovation
The invention relates to heteroaromatic antiviral compounds of formula (I), or a pharmaceutically acceptable acid addition salt or stereochemically isomeric form thereof. The compounds are defined by selected values for A, X1-X4, Y1-Y2, and R1-R14, including optional substitution patterns on phenyl and heteroaryl groups and defined choices for heteroaryl1 as thienyl, pyridinyl, or pyrimidinyl. The substituent scope is further specified through allowed sub-formulas for A and constrained definitions for substituents across the molecule.
The document also describes stereochemically defined cyclopropane- and carboxylate/carboxylic acid and carboxamide derivatives of a heteroaryl scaffold, including interconversions among named intermediates and corresponding acid and amide forms. It tracks specific intermediate identities and later intermediates through transformations to selected final compound examples, while maintaining stereochemical descriptors such as trans and cis. The synthesis description differentiates related acid versus carboxamide products via explicit carboxylic acid and carboxamide naming of the intermediates and final examples.
The invention further includes specific stereochemically defined compounds within the family and connects the compound family to therapeutic use by claiming treatment of respiratory syncytial virus infection. The disclosed work also includes pharmaceutical formulation examples, analytical characterization, and antiviral assay data for selected compounds.
Claims Coverage
The independent claims cover a structurally defined compound genus of formula (I) with explicit substituent constraints and allowance for pharmaceutically acceptable acid addition salts and stereochemically isomeric forms, together with therapeutic use directed to treating respiratory syncytial virus infection and pharmaceutical compositions containing the compound. Across the claim set, the inventive features center on the formula-level structural definition and the therapeutically effective administration/formulation for RSV treatment.
Formula (I) heteroaromatic compound genus
A compound of formula (I), or a pharmaceutically acceptable acid addition salt or stereochemically isomeric form thereof, with defined sub-formulas for A, constrained substituent options for phenyl and heteroaryl groups, and specified choices for Y1, Y2, R3, R5, and R6.
Therapeutic treatment of RSV by administration
A method for treating a respiratory syncytial virus infection by administering a therapeutically effective amount of the compound of formula (I), or a pharmaceutically acceptable acid addition salt or stereochemically isomeric form thereof, to a subject.
Pharmaceutical composition for RSV treatment
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of formula (I), optionally as a pharmaceutically acceptable acid addition salt or stereochemically isomeric form.
Overall, the claim coverage centers on a structurally defined formula (I) compound class with explicit substituent rules and includes use in pharmaceutical compositions and methods for treating respiratory syncytial virus infection by administering therapeutically effective amounts.
Stated Advantages
Not explicitly described in patent.
Documented Applications
Treating a respiratory syncytial virus infection by administering a therapeutically effective amount of the compound.
Antiviral activity evaluation, including in vitro antiviral activity described in terms of virus yield reduction and in vivo antiviral activity described in an in vivo cotton rat model.
Pharmaceutical formulation examples, including tablets, suspension, injectable, and ointment.
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