Novel substituted azabenzoxazoles

A compound represented by Formula I:

• or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, wherein:
• Y is N;
• A is N, or CH;
• X is O or S;
• Z is selected from the group consisting of phenyl, benzothiazolyl, indolyl, pyridyl, pyrazolopyridinyl, benzodioxolyl, and pyrrolopyridinyl all optionally substituted with 1 to 3 groups of R2, R3 or R4;
• R represents hydrogen, or -C1-6alkyl;
• R1 represents hydrogen, -C5-10 heterocyclyl, —N(R2)2, CN, —(CH2)nhalo, CF3, —O(CH2)nR, —O(CH2)nC5-10 heterocyclyl, -C1-6alkyl, —OCF3, —O(CH2)nF, —(O(CH2)s)phalo, —(O(CH2)s)pOR, —C(O)OR, or hetero-spirocycle said alkyl, and heterocyclyl optionally substituted with 1 to 3 groups of Ra, with the proviso that R1, R2, R3 and R4 are not hydrogen at the same time, or when R1 is hydrogen, Z is not phenyl;
• R2, R3 and R4 independently represent hydrogen, —(CH2)nhalo, —C1-6alkyl, —CF3, —(CH2)nOR, (CH2)nC5-10 heterocyclyl, —N(R)2, said alkyl, and heterocyclyl optionally substituted with 1 to 3 groups of Ra;
• Ra represents —CN, NO2, halo, CF3, -C1-6alkyl, -C1-6alkenyl, -C1-6alkynyl, —(CH2)nhalo, —OR, —NRR1, —C(═NR1)NR2R3, —N(═NR1)NR2R3, —NR1COR2, —NR1CO2R2, —NR1SO2R4, —NR1CONR2R3, —SR4, —SOR4, —SO2R4, —SO2NR1R2, —COR1, —CO2R1, —CONR1R2, —C(═NR1)R2, or —C(═NOR1)R2;
• n represents 0-6;
• s represents 2-4;
• and
• p represents 1-3.

A compound which is:

• 2-(4-methoxyphenyl)-N-(3-methoxypropyl)[1,3]oxazolo[5,4-b]pyridin-5-amine,
• 2-(4-methoxyphenyl)-5-(1,3-oxazol-2-ylmethoxy)[1,3]oxazolo[5,4-b]pyridine,
• 5-(2-azaspiro[4,4]non-2-yl)-2-(4-methoxyphenyl)[1,3]oxazolo[5,4-b]pyridine,
• 5-[2-(2-methoxyethoxy)ethoxy]-2-(4-methoxyphenyl)[1,3]oxazolo[5,4-b]pyridine,
• N-butyl-2-(4-methoxyphenyl)[1,3]oxazolo[5,4-b]pyridin-5-amine,
• 2-(4-methoxyphenyl)-N,N-dimethyl[1,3]oxazolo[5,4-b]pyridin-5-amine,
• 2-(4-methoxyphenyl)-5-morpholin-4-yl[1,3]oxazolo[5,4-b]pyridine,
• N-(2-methoxyethyl)-2-(4-methoxyphenyl)[1,3]oxazolo,
• 2-(4-methoxyphenyl)-5-(2-methylmorpholin-4-yl)[1,3]oxazolo[5,4-b]pyridine,
• N,N-dimethyl-2-[4-(methylamino)phenyl][1,3]oxazolo[5,4-b]pyridin-5-amine,
• N-methyl-4-(5-morpholin-4-yl[1,3]oxazolo[5,4-b]pyridin-2-yl)aniline,
• N-(2-methoxyethyl)-2-[4-(methylamino)phenyl][1,3]oxazolo[5,4-b]pyridin-5-amine,
• N-methyl-4-[5-(2-methylmorpholin-4-yl)[1,3]oxazolo[5,4-b]pyridin-2-yl]aniline,
• N-methyl-2-[4-(methylamino)phenyl]-N-(2-pyrrolidin-1-ylethyl)[1,3]oxazolo[5,4-b]pyridin-5-amine,
• 2-[4-(methylamino)phenyl]-N-(1-methylethyl)[1,3]oxazolo[5,4-b]pyridin-5-amine,
• N-methyl-4-(5-pyrrolidin-1-yl[1,3]oxazolo[5,4-b]pyridin-2-yl)aniline,
• N-ethyl-2-[4-(methylamino)phenyl][1,3]oxazolo[5,4-b]pyridin-5-amine,
• 4-(5-fluoro[1,3]oxazolo[5,4-b]pyridin-2-yl)-N-methylaniline,
• 5-fluoro-2-(2-methyl-1,3-benzothiazol-6-yl)[1,3]oxazolo[5,4-b]pyridine,
• 5-fluoro-2-(1-methyl-1H-indol-5-yl)[1,3]oxazolo[5,4-b]pyridine,
• 2-(1,3-benzothiazol-6-yl)-5-fluoro[1,3]oxazolo[5,4-b]pyridine,
• 2-(2,3-dimethyl-1H-indol-5-yl)-5-fluoro[1,3]oxazolo[5,4-b]pyridine,
• 5-fluoro-2-(6-fluoro-5-methylpyridin-3-yl)[1,3]oxazolo[5,4-b]pyridine,
• 5-fluoro-2-[1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl][1,3]oxazolo[5,4-b]pyridine,
• 2-(4-ethoxyphenyl)-5-fluoro[1,3]oxazolo[5,4-b]pyridine,
• 2-(1,3-benzodioxol-5-yl)-5-fluoro[1,3]oxazolo[5,4-b]pyridine,
• 4-(5-fluoro[1,3]oxazolo[5,4-b]pyridin-2-yl)-N,N-dimethylaniline,
• 5-fluoro-2-(4-piperidin-1-ylphenyl)[1,3]oxazolo[5,4-b]pyridine,
• 2-(4-methoxyphenyl)-N-(1-methylethyl)[1,3]oxazolo[5,4-b]pyridin-5-amine,
• 2-(4-methoxyphenyl)-5-pyrrolidin-1-yl[1,3]oxazolo[5,4-b]pyridine,
• 5-fluoro-2-[4-(1H-1,2,4-triazol-1-yl)phenyl][1,3]oxazolo[5,4-b]pyridine,
• 5-fluoro-2-(1H-indol-5-yl)[1,3]oxazolo[5,4-b]pyridine,
• 5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)[1,3]oxazolo[5,4-b]pyridine,
• [5-(5-Fluoro-oxazolo[5,4-b]pyridin-2-yl)-pyridin-2-yl]-methyl-amine,
• [5-(5-Fluoro-oxazolo[5,4-b]pyridin-2-yl)-pyridin-2-yl]-dimethyl-amine,
• 5-Fluoro-2-(6-[1,2,4]triazol-1-yl-pyridin-3-yl)-oxazolo[5,4-b]pyridine,
• 5-Fluoro-2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-oxazolo[5,4-b]pyridine,
• 5-chloro-2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-oxazolo[5,4-b]pyridine,
• 5-Fluoro-2-[6-(3-methyl-3H-imidazol-4-yl)-pyridin-3-yl] -oxazolo[5,4-b]pyridine,
• [5-(5-Fluoro-oxazolo[5,4-b]pyridin-2-yl)-3-methyl-pyridin-2-yl]-methyl-amine,
• 5-Fluoro-2-(1-methyl-1H-indazol-5-yl)-oxazolo[5,4-b]pyridine,
• 5-Fluoro-2-(1H-indol-6-yl)-oxazolo[5,4-b]pyridine,
• 5-Fluoro-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-oxazolo[5,4-b]pyridine,
• 2-(1,2-Dimethyl-1H-benzoimidazol-5-yl)-5-fluoro-oxazolo[5,4-b]pyridine,
• 5-Fluoro-2-(1-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)-oxazolo[5,4-b]pyridine,
• 2-(3-Bromo-imidazo[1,2-a]pyridin-7-yl)-5-fluoro-oxazolo[5,4-b]pyridine,
• 5-Fluoro-2-(3-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-oxazolo[5,4-b]pyridine,
• 5-Fluoro-2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-thiazolo[5,4-b]pyridine,
• 5-Fluoro-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)-thiazolo[5,4-b]pyridine,
• [4-(6-Fluoro-oxazolo[4,5-c]pyridin-2-yl)-phenyl]-dimethyl-amine,
• or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof.

A method for measuring amyloid deposits in a patient comprising the steps of administering a detectable quantity of a compound of formula I:

• or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, wherein:
• X is O or S;
• A and Y independently are N, or CH;
• Z is selected from the group consisting of phenyl, benzothiazolyl, indolyl, pyridyl, pyrazolopyridinyl, benzodioxolyl, and pyrrolopyridinyl all optionally substituted with 1 to 3 groups of R2, R3 or R4;
• R represents hydrogen, or -C1-6alkyl;
• R1 represents hydrogen, -C5-10 heterocyclyl, —N(R2)2, CN, —(CH2)nhalo, CF3, —O(CH2)nR, —O(CH2)nC5-10heterocyclyl, -C1-6alkyl, —OCF3, —O(CH2)nF, —(O(CH2)s)phalo, —(O(CH2)s)pOR, —C(O)OR, or hetero-spirocycle said alkyl, and heterocyclyl optionally substituted with 1 to 3 groups of Ra,
• R2, R3 and R4 independently represent hydrogen, —(CH2)nhalo, -C1-6alkyl, —CF3, —(CH2)nOR, (CH2)nC5-10 heterocyclyl, —N(R)2, said alkyl, and heterocyclyl optionally substituted with 1 to 3 groups of Ra;
• Ra represents —CN, NO2, halo, CF3, -C1-6alkyl, -C1-6alkenyl, -C1-6alkynyl, —(CH2)nhalo, —OR, —NRR1, —C(═NR1)NR2R3, —N(═NR1)NR2R3, —NR1COR2, —NR1CO2R2, —NR1SO2R4, —NR1CONR2R3, —SR4, —SOR4, —SO2R4, —SO2NR1R2, —COR1, —CO2R1, —CONR1R2, —C(═NR1)R2, or —C(═NOR1)R2;
• n represents 0-6;
• s represents 2-4;
• and
• p represents 1-3
• and detecting the binding of the compound to amyloid deposits in the patient.