Back to results
US 2003/0069271 A1Published application
Quinolone compounds for use in treating viral infections
OwnerClarence Webster Andrews,III, George Andrew Freeman +1inventors
InventorsClarence Webster Andrews,III, George Andrew Freeman, Andrew Lee Hopkins
Life of this patent
Estimating the term…
Abstract
The present invention relates to quinolone compounds and their use in the treatment of viral infections.
Claims19
A compound of formula (Ia)
- 14
- wherein:
- R1 is hydrogen;
- R2 is oxygen or sulfur;
- R3 is trifluoromethyl;
- cyano;
- C1-8alkyl optionally substituted with C1-8alkyl or trifluoromethyl;
- or OR15, wherein R15 is C1-8alkyl optionally substituted with C1-8alkyl;
- R4 is
- OR11, wherein R11 is C2-8alkenyl optionally substituted with C1-8alkyl;
- C1-8alkyl optionally substituted with C1-8alkyl;
- C6-14arylalkyl;
- C3-6cycloalkyl;
- C3-6cycloalkylalkyl;
- heterocyclealkyl;
- heterocyclealkynyl;
- C3-6cycloalkylalkenyl;
- C6-14arylalkynyl;
- C3-6cycloalkylalkynyl;
- SR12, wherein R12 is C3-6Cycloalkyl;
- S(O)R12, wherein R12 is C3-6cycloalkyl;
- or
- NR13R14 wherein R13 and R14, which may be the same or different, are hydrogen or C1-8alkyl, optionally substituted with C1-8alkyl;
- R5 is hydrogen;
- nitro;
- halogen;
- C1-8alkyl, optionally substituted with C1-8alkyl or trifluoromethyl;
- R6 is hydrogen;
- halogen;
- C1-8alkyl;
- cyano;
- trifluoromethyl;
- or OR10 wherein R10 is C1-8alkyl or trifluoromethyl;
- R7 is hydrogen;
- C1-8alkyl;
- halogen;
- C6-14aryl;
- C1-8alkylaryl;
- C2-8alkynyl;
- heteroaryl;
- or OR9 wherein R9 is C1-8alkyl;
- R8 is hydrogen;
- halogen;
- cyano;
- nitro;
- or OR16, wherein R16 is hydrogen or C1-8alkyl optionally substituted with C1-8alkyl or trifluoromethyl;
- provided that R6 and R7 cannot both be hydrogen;
- and further provided that when R1 is H, R2 is O, R3 is C1-8alkyl, R4 is OR11 wherein R11 is C1-8alkyl, R5 is H, R6 is H or OR10 wherein R10 is C1-8alkyl, R7 is H, C1-8alkyl, or OR9 wherein R9 is C1-8alkyl, then R8 cannot be H or OR16 wherein R16 is H or C1-8alkyl;
- or a pharmaceutically acceptable derivative thereof.
46 more elements
A compound of formula (Ib) wherein:
- 15
- R1 is hydrogen;
- R2 is oxygen or sulfur;
- R3 is trifluoromethyl;
- cyano;
- C1-8alkyl optionally substituted with C1-8alkyl or trifluoromethyl;
- or OR15, wherein R15 is C1-8alkyl optionally substituted with C1-8alkyl;
- R4 is
- OR11, wherein R11 is C2-8alkenyl optionally substituted with C1-8alkyl;
- C1-8alkyl optionally substituted with C1-8alkyl;
- C6-14arylalkyl;
- C3-6cycloalkyl;
- C3-6cycloalkylalkyl;
- heterocyclealkyl;
- heterocyclealkynyl;
- C3-6cycloalkylalkenyl;
- C6-14arylalkynyl;
- C3-6cycloalkylalkynyl;
- SR12, wherein R12 is C3-6cycloalkyl;
- S(O)R12, wherein R12 is C3-6cycloalkyl;
- or
- NR13R14 wherein R13 and R14, which may be the same or different, are hydrogen or C1-8alkyl, optionally substituted with C1-8alkyl;
- R5 is hydrogen;
- nitro;
- halogen;
- C1-8alkyl, optionally substituted with C1-8alkyl or trifluoromethyl;
- R7 is hydrogen;
- C1-8alkyl;
- halogen;
- C6-14aryl;
- C1-8alkylaryl;
- C2-8alkynyl;
- heteroaryl;
- or OR9 wherein R9 is C1-8alkyl;
- R8 is hydrogen;
- halogen;
- cyano;
- nitro;
- or OR16, wherein R16 is hydrogen or C1-8alkyl optionally substituted with C1-8alkyl or trifluoromethyl;
- or a pharmaceutically acceptable derivative thereof.
37 more elements
A compound of formula (Ic) wherein:
- 16
- R1 is hydrogen;
- R2 is oxygen or sulfur;
- R3 is trifluoromethyl;
- cyano;
- C1-8alkyl optionally substituted with C1-8alkyl or trifluoromethyl;
- or OR15, wherein R15 is C1-8alkyl optionally substituted with C1-8alkyl;
- R4 is
- OR11, wherein R11 is C2-8alkenyl optionally substituted with C1-8alkyl;
- C1-8alkyl optionally substituted with C1-8alkyl;
- C6-14arylalkyl;
- C3-6cycloalkyl;
- C3-6cycloalkylalkyl;
- heterocyclealkyl;
- heterocyclealkynyl;
- C3-6cycloalkylalkenyl;
- C6-14arylalkynyl;
- C3-6cycloalkylalkynyl;
- SR12, wherein R12 is C3-6cycloalkyl;
- S(O)R12, wherein R12 is C3-6cycloalkyl;
- or
- NR13R14 wherein R13 and R14, which may be the same or different, are hydrogen or C1-8alkyl, optionally substituted with C1-8alkyl;
- R5 is hydrogen;
- nitro;
- halogen;
- C1-8alkyl, optionally substituted with C1-8alkyl or trifluoromethyl;
- R6 is hydrogen;
- halogen;
- C1-8alkyl;
- cyano;
- trifluoromethyl;
- or OR10 wherein R10 is C1-8alkyl or trifluoromethyl;
- R8 is hydrogen;
- halogen;
- cyano;
- nitro;
- or OR16, wherein R16 is hydrogen or C1-8alkyl optionally substituted with C1-8alkyl or trifluoromethyl;
- or a pharmaceutically acceptable derivative thereof.
35 more elements
A compound selected from the group consisting of
- 6-Chloro-4-(cyclohexyloxy)-3-propyl-2(1H)-quinolinone;
- 6-Chloro-4-(cyclobutylmethoxy)-3-propyl-2(1H)-quinolinone;
- 6-Chloro-4-(cyclopropylmethoxy)-3-propyl-2(1H)-quinolinone;
- 6-Chloro-4-(cyclopentyloxy)-3-propyl-2(1H)-quinolinone;
- 6-Chloro-4-(cyclohexylmethoxy)-3-propyl-2(1H)-quinolinone;
- 6-Chloro-4-(1,3-dioxolan-2-ylmethoxy)-3-propyl-2(1H)-quinolinone;
- 4-Benzyloxy-6-chloro-3-propyl-2(1H)-quinolinone;
- 6-Chloro-4-(cyclobutyloxy)-3-propyl-2(1H)-quinolinone;
- 6-Chloro-4-(cyclohexyloxy)-3-isopropyl-2(1H)-quinolinone;
- 4-Cyclopentyloxy-6-methyl-3-propyl-2(1H)-quinolinone;
- 4-Cyclopentyloxy-6-methoxy-3-propyl-2(1H)-quinolinone;
- 4-(Cyclopentyloxy)-3-propyl-6-trifluoromethoxy-2(1H)-quinolinone;
- 4-Cyclopentyloxy-2-oxo-3-propyl-1,2-dihydro-6-quinolinecarbonitrile
- 6-Bromo-4-(cyclopentyloxy)-3-propyl-2(1H)-quinolinone;
- 4-Cyclopentyloxy-3-propyl-2(1H)-quinolinone;
- 6-Chloro-4-cyclobutylmethoxy-3-isopropyl-2(1H)-quinolinone;
- 6-Chloro-4-(cyclopentyloxy)-3-ethyl-2(1H)-quinolinone;
- 3-(sec-Butyl)-6-chloro-4-(cyclopentyloxy)-2(1H)-quinolinone;
- 6-Chloro-4-(cyclopentyloxy)-3-isobutyl-2(1H)-quinolinone;
- 6-Chloro-4-(cyclohexyloxy)-3-propyl-2(1H)-quinolinethione;
- 6-Chloro-4-(cyclobutylmethoxy)-3-propyl-2(1H)-quinolinethione;
- 3-(sec-Butyl)-6-chloro-4-(cyclopentyloxy)-2(1H)-quinolinethione;
- 6-Chloro-4-(cyclohexylsulfanyl)-3-propyl-2(1H)-quinolinone;
- 6-Chloro-4-(cyclohexylsulfinyl)-3-propyl-2(1H)-quinolinone;
- 4-Cyclopentyloxy-6-fluoro-3-propyl-2(1H)-quinolinone;
- 4-Cyclobutylmethoxy-6-fluoro-3-propyl-2(1H)-quinolinone;
- 3-sec-Butyl-4-(cyclobutyhmethoxy)-6-fluoro-2(1H)-quinolinone;
- 4-(Cyclobutylmethoxy)-6-fluoro-3-isopropyl-2(1H)-quinolinone;
- 4-Cyclopentyloxy-6-fluoro-3-propyl-2(1H)-quinolinethione;
- 4-(Cyclobutylmethoxy)-6-fluoro-3-propyl-2(1H)-quinolinethione;
- 4-(Cyclobutylmethoxy)-6-fluoro-3-isopropyl-2(1H)-quinolinethione;
- 6-Chloro-4-(isobutylamino)-3-propyl-2(1H)-quinolinone;
- 6- Chloro-4-(cyclobutylmethoxy)-3-ethoxy-2(1H)-quinolinone;
- 4-(Cyclobutylmethoxy)-3-ethoxy-6-fluoro-2(1H)-quinolinone;
- 6-Chloro-4-[(2-cyclopropylethynyl)oxy]-3-propyl-2(1H)-quinolinone;
- 4-[(2-Cyclopropylethynyl)oxy]-6-fluoro-3-(isopropyl)-2(1H)-quinolinone;
- 4-[(2-Cyclopropylethynyl)oxy]-6-fluoro-3-propyl-2(1H)-quinolinone;
- 6-Fluoro-3-isopropyl-4-[(3-methyl-1-pentynyl)oxy]-2(-quinolinone;
- 4-(Cyclobutylmethoxy)-3-ethyl-6-fluoro-2(1H)-quinolinone;
- 4-Cyclobutylmethoxy-3-isopropyl[1,6]naphthyridin-2(1H)-one;
- 3-sec-Butyl-4-cyclobutyhmethoxy[1,6]naphthyridin-2(1H)-one;
- 6-Fluoro-3-isopropyl-4-[(3-methyl-2-butenyl)oxy]-2(1H)-quinolinone;
- 6-Fluoro-3-isopropyl-4-[(2-methyl-2-propenyl)oxy]-2(1H)-quinolinone;
- 4-(Cyclobutylmethoxy)-6-fluoro-5-nitro-3-propyl-2(1H)-quinolinone;
- 4-[(2-Cyclopropylethynyl)oxy]-3-ethyl-6-fluoro-2(1H)-quinolinone;
- 6-Chloro-4-[(2-Cyclopropylethynyl)oxy]-3-isopropyl-2(1H)-quinolinone;
- 4-[(2-Cyclopropylethynyl)oxy]-6-fluoro-3-isobutyl-2(1H)-quinolinone;
- 4- {[(E)-2-Cyclopropylethenyl]oxy}-6-fluoro-3-isopropyl-3,4-dihydro-2(1H)-quinolinone;
- 4-Cyclobutylmethoxy-6-fluoro-3-methyl-2(1H)-quinolinone;
- and pharmaceutically acceptable derivatives thereof.
47 more elements
A compound selected from the group consisting of
- 6-Chloro-4-[(2-cyclopropylethynyl)oxy]-3-propyl-2(1H)-quinolinone (example 35);
- 4-[(2-Cyclopropylethynyl)oxy]-6-fluoro-3-propyl-2(1H)-quinolinone (example 37);
- 4-[(2-Cyclopropylethynyl)oxy]-3-ethyl-6-fluoro-2(1H)-quinolinone (example 45);
- 6-Chloro-4-[(2-Cyclopropylethynyl)oxy]-3-isopropyl-2(1H)-quinolinone (example 46);
- 4-[(2-Cyclopropylethynyl)oxy]-6-fluoro-3-isobutyl-2(1H)-quinolinone (example 47);
- 4-[(2-Cyclopropylethynyl)oxy]-6-fluoro-3-isopropyl-2(1H)-quinolinone (example 36);
- and pharmaceutically acceptable derivatives thereof.
4 more elements
Dependencies are inferred from the claim text.