Antiviral agents and uses thereof
Inventors
Von Itzstein, Mark • El-Deeb, Ibrahim • Guillon, Patrice • Heilig, Larissa
Assignees
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Publication Number
US-12590092-B2
Publication Date
2026-03-31
Expiration Date
Abstract
The present invention relates to a compound of Formula (I), or a pharmaceutically acceptable salt thereof: and to pharmaceutical compositions comprising the compound. In Formula (I), R3 is selected from the group consisting of: wherein rings W, X, Y and Z may relate to various heterocyclic, heteroaryl, cycloalkyl, cycloalkenyl, and/or aryl rings. The present invention also relates to uses of the compounds in treating a disease, disorder or condition caused by viral infection.
Core Innovation
The invention provides compounds of formula (I), or pharmaceutically acceptable salts thereof, defined by selection rules for R1, R3, R4, and ring systems W, X, Y, and Z, together with defined options for R6, R7, and R8. The scaffold includes optionally substituted monocyclic or fused bicyclic heterocyclic or heteroaryl ring embodiments, and ring Z may be absent in some embodiments.
R1 is defined as COOH or a salt thereof, C(O)NR9R10, or C(O)OR11, and R4 is defined as sulfonamide, urea, or NHC(O)R17. R6, R7, and R8 are independently selected from H, OH, protected OH, O-R19, NR18R18′, and multiple carbonyl, thiocarbonyl, alkoxy, amido, and sulfonyl-type variants, with related R18/R18′ and R19 definitions.
The disclosed compounds are described as haemagglutinin-neuraminidase (HN) modulators, preferably inhibitors of influenza/parainfluenza HN functions, and are associated with pharmaceutical compositions and medical use coverage involving HN-contact modulation for treatment and prophylaxis. The document also describes chemical characterization and biological evaluation of hPIV-1/hPIV-3 HN inhibitors, including inhibition measurements against HN protein and viral growth endpoints, recombinant HN expression, complex formation with inhibitors, crystallisation or co-crystallization, X-ray diffraction data collection, and structure determination and refinement.
Claims Coverage
The independent claims cover compound structures of formula (I), or pharmaceutically acceptable salts thereof, with broad structural selection rules for R1, R3, R4, and R6-R8 and defined ring embodiments for W, X, Y, and Z. Across the claims, four inventive feature groupings are present, with additional narrowing in some claims to specific R4 and R6/R7/R8 subsets and a formula (III) embodiment.
Formula (I) compound with defined substituents and ring systems
A compound of formula (I), or a pharmaceutically acceptable salt thereof, with R1 selected from COOH or a salt thereof, C(O)NR9R10, or C(O)OR11; R3 defined by ring W, X, Y, and Z arrangements; R4 selected from sulfonamide, urea, or NHC(O)R17; and R6, R7, and R8 independently selected from H, OH, protected OH, O-R19, NR18R18′, and multiple carbonyl, thiocarbonyl, alkoxy, amido, and sulfonyl-type variants.
Formula (III) embodiment
A compound of formula (I), or a pharmaceutically acceptable salt thereof, that is a compound of formula (III), as defined by the substituent pattern of formula (III).
Restricted R4 NHC(O) substituent embodiments
A compound of formula (I), or a pharmaceutically acceptable salt thereof, in which R4 is selected from sulfonamide, urea, and NHC(O)R17, with further specific NHC(O)R17 embodiments including NHC(O)CH3, NHC(O)CH(CH3)2, NHC(O)CF3, and NHC(O)CH2CH3.
Restricted R6, R7, and R8 embodiments
A compound of formula (I) in which R6, R7, and R8 are each independently selected from OH and —OC(O)CH3.
The claims define antiviral compounds of formula (I) with broad, enumerated structural constraints on R1, R3, R4, and R6-R8 and on ring systems W/X/Y/Z. The claims also include narrower embodiments for specific NHC(O) substituents, restriction of R6/R7/R8 to OH or —OC(O)CH3, and an embodiment requiring formula (III).
Stated Advantages
The compounds are presented as hPIV-1/hPIV-3 HN inhibitors.
Provides haemagglutinin-neuraminidase (HN) modulators, preferably inhibitors of influenza/parainfluenza HN functions.
Documented Applications
Inhibition measurements against HN protein and viral growth endpoints for hPIV-1 and hPIV-3.
Recombinant HN expression, complex formation with inhibitors, crystallisation or co-crystallization, X-ray diffraction data collection, and structure determination and refinement.
Treatment of disease caused by viral infection, including viral respiratory infection.
Treatment and prophylaxis medical use via HN-contact modulation.
Haemagglutinin inhibition and neuraminidase inhibition assays, including in situ ELISA, in a biological evaluation context.
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