Deazapurine derivatives; a new class of CRF1 specific ligands

A method of treating a stress disorder, comprising administering to a patient suffering from at least one stress disorder an effective amount of a compound of the formula:

• or a pharmaceutically acceptable salt thereof wherein:
• Ar is phenyl, 2-, 3-, or 4-pyridyl, 2- or 3-thienyl, 4- or 5-pyrimidyl, each of which is mono-, di-, or trisubstituted with halogen, hydroxy, lower alkyl, or lower alkoxy, with the proviso that at least one of the ortho positions of the Ar substituent is substituted;
• X is CH or nitrogen;
• R1 is lower alkyl;
• R2 is hydrogen, halogen, lower alkyl, lower alkoxy, or thioalkoxy;
• or
• R1 and R2 taken together represent —(CH2)n—A—(CH2)m—,
• where n is 2, 3 or 4, A is methylene, oxygen, sulfur or NR6,
• where R6 is lower alkyl, and
• m is 0, 1 or 2;
• R3 and R4 are the same or different and represent hydrogen or lower alkyl;
• phenyl, 2-, 3-, or 4-pyridyl, 2-, or 3-thienyl, or 2-, 4-, or 5-pyrimidyl, each of which is mono- or disubstituted with halogen, hydroxy, lower alkyl, or lower alkoxy;
• phenyl lower alkyl, 2-, 3-, or 4-pyridyl lower alkyl, 2- or 3-thienyl lower alkyl, or 2-, 4-, or 5-pyrimidyl lower alkyl;
• cycloalkyl having 3-8 carbon atoms or cycloalkyl lower alkyl where the cycloalkyl portion has 3-8 carbon atoms;
• 2-hydroxyethyl or 3-hydroxypropyl optionally mono or disubstituted with lower alkyl with the proviso that not both R3 and R4 are hydrogen;
• or
• R3 and R4 taken together represent —(CH2)n—A—(CH2)m—
• where n is 2, or 3,
• A is methylene, 1,2 phenylene, oxygen, sulfur or NR6,
• wherein R6 is lower alkyl, phenyl, 2-, 3-, or 4-pyridyl, 2-or 3-thienyl or 2-, 4-, or 5-pyrimidyl, phenyl lower alkyl, 2-, 3-, or 4-pyridyl lower alkyl, 2- or 3-thienyl lower alkyl, or 2-, 4-, or 5-pyrimidyl lower alkyl, and
• m is 1, 2 or 3;
• R5 is hydrogen, halogen, lower alkyl, lower alkoxy, or thioalkoxy.