Ketone ligands for modulating the expression of exogenous genes via an ecdysone receptor complex

A compound of formula I:

• wherein Q1 is selected from the group consisting of O and S;
• R1 is selected from the group consisting of 2-methyl-3,4-methylenedioxyphenyl, 2-ethyl-3,4-methylenedioxyphenyl, 2-methyl-3,4-ethylenedioxyphenyl, 2-ethyl-3,4-ethylenedioxyphenyl, and 2-methyl-3,4-oxydimethylenephenyl;
• R2 and R3 are independently:
• (a) cyano, aminocarbonyl, carboxy, (C1-C6)alkyl, (C3-C6)cycloalkyl, halo(C1-C6)alkyl, (C3-C6)halocycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)haloalkenyl, (C2-C6)alkynyl, (C1-C6)alkylsulfonyl, (C1-C6)alkoxy(C1-C6)alkyl, (C1-C6)alkylthio(C1-C6)alkyl, (C1-C6)alkylsulfinyl(C1-C6)alkyl, (C1-C6)alkylsulfonyl(C1-C6)alkyl, (C1-C6)alkylamino(C1-C6)alkyl, di(C1-C6)alkylamino(C1-C6)alkyl, (C1-C6)alkylcarbonyl, (C1-C6)alkylcarbonyl(C1-C6)alkyl, (C1-C6)alkylaminocarbonyl, di(C1-C6)alkylaminocarbonyl, (C1-C6)alkylaminocarbonyl(C1-C6)alkyl, di(C1-C6)alkylaminocarbonyl(C1-C6)alkyl, (C1-C6)alkylcarbonylamino(C1-C6)alkyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkoxycarbonyl(C1-C6)alkyl, cyano(C1-C6)alkyl, hydroxy(C1-C6)alkyl, or carboxy(C1-C6)alkyl;
• or
• (b) unsubstituted or substituted phenyl, phenyl(C1-C6)alkyl, benzoyl, naphthyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, furanyl, thiophenyl, benzothiophenyl, benzofuranyl, isoxazolyl, or imidazolyl, heterocyclylcarbonyl, wherein the substituents are independently selected from the group consisting of cyano, nitro, halo, aminocarbonyl, aminothiocarbonyl, carboxy, formyl, hydroxy, amino, carbamoyl, (C1-C3)alkyl, (C1-C3)haloalkyl, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C1-C3)alkythio, (C1-C3)haloalkylthio, (C1-C3)alkylsulfonyl, (C1-C3)alkylamino, di(C1-C3)alkylamino, (C1-C2)alkoxy(C1-C2)alkyl, (C1-C2)alkylthio(C1-C2)alkyl, (C1-C2)alkylsulfonyl(C1-C2)alkyl, (C1-C2)alkylamino(C1-C2)alkyl, di(C1-C2)alkylamino(C1-C2)alkyl, (C1-C3)alkylcarbonyl, (C1-C3)alkoxycarbonyl, (C1-C3)alkylaminocarbonyl, di(C1-C3)alkylaminocarbonyl, and cyano(C1-C3)alkyl;
• or
• R2 and R3 may be joined together with the carbon to which they are attached to form an unsubstituted or substituted, partially unsaturated or saturated 3-, 4-, 5-, 6-, 7- or 8-membered carbocyclic or heterocyclic ring wherein the heterocyclic ring contains from one to three heteroatoms selected from O, N, or S;
• and the substituents are independently selected from the group consisting of cyano, nitro, halo, aminocarbonyl, aminothiocarbonyl, carboxy, formyl, hydroxy, amino, carbamoyl, (C1-C3)alkyl, (C1-C3)haloalkyl, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C1-C3)alkythio, (C1-C3)haloalkylthio, (C1-C3)alkylsulfonyl, (C1-C3)alkylamino, di(C1-C3)alkylamino, (C1-C2)alkoxy(C1-C2)alkyl, (C1-C2)alkylthio(C1-C2)alkyl, (C1-C2)alkylsulfonyl(C1-C2)alkyl, (C1-C2)alkylamino(C1-C2)alkyl, di(C1-C2)alkylamino(C1-C2)alkyl, (C1-C3)alkylcarbonyl, (C1-C4)alkoxycarbonyl, (C1-C4)alkoxycarbonyl(C1-C4)alkyl, (C1-C4)alkoxycarbonylcarbonyl, (C1-C3)alkylaminocarbonyl, di(C1-C3)alkylaminocarbonyl, cyano(C1-C3)alkyl, oxo, methoxyimino, and spiro-(C1-C4)alkadioxy;
• and
• R4 is unsubstituted or substituted phenyl or pyridyl, wherein the substituents are independently selected from the group consisting of cyano, nitro, halo, aminocarbonyl, aminothiocarbonyl, carboxy, formnyl, hydroxy, amino, carbamoyl, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C3-C6)alkadienyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C3-C6)cycloalkoxy, (C1-C6)haloalkoxy, (C3-C6)cyclohaloalkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C1-C6)alkythio, (C3-C6)cycloalkylthio, (C1-C6)haloalkylthio, (C3-C6)halocycloalkythio, (C2-C6)alkenylthio, (C2-C6)alkynylthio, (C1-C6)alkylsulfinyl, (C3-C6)cycloalkysulfinyl, (C1-C6)haloalkylsulfinyl, (C3-C6)halocycloalkylsulfinyl, (C2-C6)alkenylsulfinyl, (C3-C6)cycloalkenylsulfinyl, (C2-C6)alkynylsulfinyl, (C1-C6)alkylsulfonyl, (C3-C6)cycloalkysulfonyl, (C1-C6)haloalkylsulfonyl, (C3-C6)halocycloalkylsulfonyl, (C1-C6)alkylsulfinyl, (C3-C6)cycloalkysulfinyl, (C1-C6)haloalkylsulfinyl, (C3-C6)halocycloalkylsulfinyl, (C1-C6)alkylamino, (C3-C6)cycloalkylamino, di(C1-C6)alkylamino, di(C3-C6)(cycloalkyl)amino, (C1-C6)alkoxy(C1-C6)alkyl, (C3-C6)cycloalkoxyalkyl, (C1-C6)alkoxy(C3-C6)cycloalkyl, (C1-C6)alkylthio(C1-C6)alkyl, (C1-C6)alkylsulfinyl(C1-C6)alkyl, (C1-C6)alkylsulfonyl(C1-C6)alkyl, (C1-C6)alkylamino(C1-C6)alkyl, di(C1-C6)alkylamino(C1-C6)alkyl, (C1-C6)alkylcarbonyl, (C3-C6)cycloalkylcarbonyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylaminocarbonyl, (C3-C6)cycloalkylaminocarbonyl, di(C1-C6)alkylaminocarbonyl, di(C3-C6)(cycloalkyl)aminocarbonyl, cyano(C1-C6)alkyl, and tri(C1-C6)alkylsilyl;
• wherein in said substituted phenyl or pyridyl, two adjacent substituted positions may be joined together with the atoms to which they are attached to form an unsubstituted or substituted, unsaturated, partially unsaturated, or saturated 4-, 5-, 6- or 7-membered carbocyclic or heterocyclic ring wherein the heterocyclic ring contains from one to three heteroatoms selected from N, O, or S;
• and the substituents are independently selected from the group consisting of cyano, nitro, halo, aminocarbonyl, aminothiocarbonyl, carboxy, fonnuyl, hydroxy, amino, carbamoyl, (C1-C3)alkyl, (C1-C3)haloalkyl, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C1-C3)alkythio, (C1-C3)haloalkylthio, (C1-C3)alkylsulfonyl, (C1-C3)alkylamino, di(C1-C3)alkylamino, (C1-C2)alkoxy(C1-C2)alkyl, (C1-C2)alkylthio(C1-C2)alkyl, (C1-C2)alkylsulfonyl(C1-C2)alkyl, (C1-C2)alkylamino(C1-C2)alkyl, di(C1-C2)alkylamino(C1-C2)alkyl, (C1-C3)alkylcarbonyl, (C1-C3)alkoxycarbonyl, (C1-C3)alkylaminocarbonyl, di(C1-C3)alkylaminocarbonyl, cyano(C1-C3)alkyl, oxo, and methoxyimino.