Fluoroalkyoxybenzylamino derivatives of nitrogen containing heterocycles

A compound of the formula

• 17
• wherein X1 is hydrogen, (C1-C10) alkoxy optionally substituted with from one to three fluorine atoms or (C1-C10) alkyl optionally substituted with from one to three fluorine atoms;
• X2 and X3 are independently selected from halo, hydrogen, nitro, (C1-C10) alkyl optionally substituted with from one to three fluorine atoms, (C1-C10) alkoxy optionally substituted with from one to three fluorine atoms, trifluoromethyl, hydroxy, phenyl, cyano, amino, (C1-C6)—
• 18
• Q is a group of the formula
• 19
• wherein R1 is a radical selected from furyl, thienyl, pyridyl, indolyl, biphenyl and phenyl optionally substituted with one or two substituents independently selected from halo, (C1-C10) alkyl optionally substituted with from one to three fluorine atoms, (C1-C10) alkoxy optionally substituted with from one to three fluorine atoms, carboxy, benzyloxycarbonyl and (C1-C3) alkoxy-carbonyl;
• R13 is selected from (C3-C4) branched alkyl, (C5-C6) branched alkenyl, (C5-C7) cycloalkyl, and the radicals named in the definition of R1;
• R2 is hydrogen or (C1-C6) alkyl;
• R3 is phenyl, biphenyl, naphthyl, pyridyl, benzhydryl, thienyl or furyl, and R3 may optionally be substituted with from one to three substituents independently selected from halo, (C1-C10) alkyl optionally substituted with from one to three fluorine atoms and (C1-C10) alkoxy optionally substituted with from one to three fluorine atoms;
• Y is (CH2)1 wherein 1 is an integer from one to three, or Y is a group of the formula
• 20
• Z is oxygen, sulfur, amino, (C1-C3)alkylamino or (CH2)n wherein n is zero, one or two;
• o is two or three;
• p is zero or one;
• R4 is furyl, thienyl, pyridyl, indolyl, biphenyl, or phenyl optionally substituted with one or two substituents independently selected from halo, (C1-C10) alkyl optionally substituted with from one to three fluorine atoms, (C1-C10) alkoxy optionally substituted with from one to three fluorine atoms, carboxy, (C1-C3) alkoxy-carbonyl and benzyloxycarbonyl;
• R5 is thienyl, biphenyl or phenyl optionally substituted with one or two substituents independently selected from halo, (C1-C10) alkyl optionally substituted with from one to three fluorine atoms and (C1-C10) alkoxy optionally substituted with from one to three fluorine atoms;
• each of the two dashed lines in formula I and the dashed line in formula II represent an optional double bond that may optionally exist when Q is a group of the formula II;
• X is (CH2)q wherein q is an integer from 1 to 6, and wherein any one of the carbon-carbon single bonds in said (CH2)q may optionally be replaced by a carbon-carbon double bond, and wherein any one of the carbon atoms of said (CH2)q may optionally be substituted with R8, and wherein any one of the carbon atoms of said (CH2)q may optionally be substituted with R9;
• m is an integer from 0 to 8, and any one of the carbon-carbon single bonds of (CH2)m may optionally be replaced by a carbon-carbon double bond or a carbon-carbon triple bond, and any one of the carbon atoms of said (CH2)m may optionally be substituted with R11;
• R6 is a radical selected from hydrogen, (C1-C6) straight or branched alkyl, (C3-C7) cycloalkyl wherein one of the carbon atoms may optionally be replaced by nitrogen, oxygen or sulfur;
• aryl selected from biphenyl, phenyl, indanyl and naphthyl;
• heteroaryl selected from thienyl, furyl, pyridyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl and quinolyl;
• phenyl (C2-C6) alkyl, benzhydryl and benzyl, wherein each of said aryl and heteroaryl groups and the phenyl moieties of said benzyl, phenyl (C2-C6) alkyl and benzhydryl may optionally be substituted with one or more substituents independently selected from halo, nitro, (C1-C10) alkyl optionally substituted with from one to three fluorine atoms, (C1-C10) alkoxy optionally substituted with from one to three fluorine atoms, amino, hydroxy-(C1-C6)alkyl, (C1-C6) alkoxy-(C1-C6) alkyl,
• 21
• wherein one of the phenyl moieties of said benzhydryl may optionally be replaced by naphthyl, thienyl, furyl or pyridyl;
• R7 is hydrogen, phenyl or (C1-C6)alkyl;
• or R6 and R7, together with the carbon to which they are attached, form a saturated carbocyclic ring having from 3 to 7 carbon atoms wherein one of said carbon atoms may optionally be replaced by oxygen, nitrogen or sulfur;
• R8 and R9 are each independently selected from hydrogen, hydroxy, halo, amino, oxo (═O), nitrile, hydroxy-(C1-C6)-alkyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkylamino, di-(C1-C6)alkylamino, (C1-C6)alkoxy,
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• and the radicals set forth in the definition of R6;
• R10 is
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• NHCH2R12, NHSO2R12 or one of the radicals set forth in any of the definitions of R6, R8 and R9;
• R11 is oximino (═NOH) or one of the radicals set forth in any of the definitions of R6, R8 and R9;
• and
• R12 is (C1-C6)alkyl, hydrogen, phenyl(C1-C6)alkyl or phenyl optionally substituted with (C1-C6)alkyl;
• with the proviso that (a) when m is 0, R11 is absent, (b) neither R8, R9, R10 nor R11 can form, together with the carbon to which it is attached, a ring with R7, (c) when Q is a group of the formula VIII, R8 and R9 cannot be attached to the same carbon atom, (d) when R8 and R9 are attached to the same carbon atom, then either each of R8 and R9 is independently selected from hydrogen, fluoro, (C1-C6) alkyl, hydroxy-(C1-C6)alkyl and (C1-C6)alkoxy-(C1-C6)alkyl, or R8 and R9, together with the carbon to which they are attached, form a (C3-C6) saturated carbocyclic ring that forms a spiro compound with the nitrogen-containing ring to which they are attached, (e) the nitrogen of formula I can not be double bonded to both Q and the substituted benzyl group to which it is attached, (f) when Q is a group of the formula VII and q is 2 and either R8 or R9 is 5-hydroxy-(C1-C6)alkyl or 5-(C1-C6)alkoxy-(C1-C6)alkyl, then the other of R8 and R9 is either 5-(C1-C6)alkyl or hydrogen;
• (g) when Q is a group of the formula VII and q is 2, then neither R8 nor R9 is 4-hydroxy-(C1-C6)alkyl or 4-(C1-C6)alkoxy-(C1-C6)alkyl, and (h) when neither X1, X2 nor X3 is a fluorinated alkoxy group, at least one of R1, R3, R4, R5, R6, R7 and R13 is an aryl group substituted with a fluorinated alkoxy group;
• or a pharmaceutically acceptable salt thereof.