Antiviral agents
AssigneeBiota Scientific Management Pty Ltd.
InventorsKeith Watson, Guy Krippner, Pauline Stanislawski, Darryl McConnell
Life of this patent
Estimating the term…
Abstract
This invention relates to compounds of formula I their salts, and pharmaceutically acceptable derivatives thereof, pharmaceutical compositions comprising these compounds and their use in the treatment of picornavirus infections in mammals, as well as novel intermediates useful in the preparation of the compounds of formula I.
Claims29
A composition comprising a compound of formula II:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4alkyl, C1-4 alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A composition comprising a compound of formula III:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4 alkyl, C1-4 alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A composition comprising a compound of formula V:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4alkyl, C1-4 alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A composition comprising a compound of formula VI:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4alkyl, C1-4alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A method for the treatment of a picornavirus infection in a respiratory tract of a mammal, comprising administering to the mammal an effective amount of a composition comprising a compound of formula II:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4 alkyl)amino, cyano, formyl, —CH═NO—C1-4 alkyl, C1-4 alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A method for the treatment of a picornavirus infection in a respiratory tract of a mammal, comprising administering to the mammal an effective amount of a composition comprising a compound of formula III:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4alkyl, C1-4alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A method for the treatment of a picornavirus infection in a respiratory tract of a mammal, comprising administering to the mammal an effective amount of a composition comprising a compound of formula V:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4alkyl, C1-4alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A method for the treatment of a picornavirus infection in a respiratory tract of a mammal, comprising administering to the mammal an effective amount of a composition comprising a compound of formula VI:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4alkyl, C1-4alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A method of prophylaxis of a picornavirus infection in a respiratory tract of a mammal, comprising administering to the mammal an effective amount of a composition comprising a compound of formula II:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4alkyl, C1-4alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A method of prophylaxis of a picornavirus infection in a respiratory tract of a mammal, comprising administering to the mammal an effective amount of a composition comprising a compound of formula III:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4alkyl, C1-4alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A method of prophylaxis of a picornavirus infection in a respiratory tract of a mammal, comprising administering to the mammal an effective amount of a composition comprising a compound of formula V:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4alkyl, C1-4alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
A method of prophylaxis of a picornavirus infection in a respiratory tract of a mammal, comprising administering to the mammal an effective amount of a composition comprising a compound of formula VI:
- wherein:
- R1 is hydrogen, C1-4alkyl, halo, hydroxyl, mercapto, trifluoromethyl, amino, mono or di(C1-4alkyl)amino, cyano, formyl, —CH═NO—C1-4alkyl, C1-4alkoxy, C1-4haloalkoxy, aryloxy, C1-4alkylthio, or aryl;
- Y is O, S, NH or NMe;
- Z is CH or N;
- Alk is C1-6alkylene;
- and
- R11 is OR10 or SR10, where R10 is C1-4alkyl;
- or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.