Inhibitors of fatty acid amide hydrolase

A method of treating an FAAH-mediated disorder comprising administering to a subject in need thereof a therapeutically effective amount of compound of formula I:

• or a pharmaceutically acceptable salt, solvate or prodrug thereof, or mixture thereof, wherein:
• is selected from a single bond and a double bond;
• when is a single bond, X1 is selected from CR4R5 and NR6, and X2 is selected from CR7R8 and NR9;
• when is a double bond, X1 is selected from CR4 and N, and X2 is selected from CR7 and N;
• X3 is selected from CR10R11 and NR12;
• provided that at least one of X1, X2 and X3 is selected from N, NR6, NR9, and N′2;
• m is 0 or 1;
• Z1 is selected from —OR13 and C1-6 alkyl;
• Z2 is selected from —OR14 and C1-6 alkyl;
• or alternatively, Z1 and Z2, together with the B to which they are bound, form an 5- to 8-membered ring having at least one O atom directly attached to B, wherein the ring is comprised of carbon atoms and optionally one or more additional heteroatoms independently selected from the group consisting of N, S, and O;
• n is 0, 1, 2 or 3;
• R1 and R2 each independently is selected from hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 perhaloalkyl, —CN and —OR15;
• or alternatively, R1 and R2, taken together with the carbon to which they are bound, form a carbonyl group;
• R3, at each occurrence, independently is selected from halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 perhaloalkyl, —OH, C1-6 alkoxy and —CN;
• R4, R5, R7, R8, R10, and R11 each independently is selected from hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 perhaloalkyl, —CN, —OR16, —NR17R18, —C(O)R19, C3-10, carbocyclyl, C6-10 aryl, C7-12 aralkyl, 3-10 membered heterocyclyl, and 5-10 membered heteroaryl;
• R6, R9, and R12 each independently is selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, —C(O)R20, —C(O)OR21, ═S(O)2R22, C3-10 carbocyclyl, C6-10 aryl, 3-10 membered heterocyclyl, 5-10 membered heteroaryl, and —(CR27R28)p—R23;
• R13 and R14, at each occurrence, each independently is selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl;
• R15 and R16, at each occurrence, each independently is selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 carbocyclyl, C6-10 aryl, C7-12 aralkyl, 3-10 membered heterocyclyl, and 5-10 membered heteroaryl;
• R17 and R18, at each occurrence, each independently is selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, —C(O)R24, —C(O)OR25, C3-10 carbocyclyl, C6-10 aryl, C7-12 aralkyl, 3-10 membered heterocyclyl, and 5-10 membered heteroaryl;
• R19, R20 and R21, at each occurrence, each independently is selected from C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 carbocyclyl, C6-10 aryl, C7-12 aralkyl, 3-10 membered heterocyclyl, and 5-10 membered heteroaryl;
• R22 is selected from C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 carbocyclyl, C6-10 aryl, 3-10 membered heterocyclyl, 5-10 membered heteroaryl, and —(CR29R30)qR26;
• R23, at each occurrence, independently is selected from C3-10 carbocyclyl, C6-10 aryl, 3-10 membered heterocyclyl, and 5-10 membered heteroaryl;
• R24 and R25, at each occurrence, each independently is selected from C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 carbocyclyl, C6-10 aryl, C7-12 aralkyl, 3-10 membered heterocyclyl, and 5-10 membered heteroaryl;
• R26, at each occurrence, independently is selected from C3-10 carbocyclyl, C6-10 aryl, 3-10 membered heterocyclyl, and 5-10 membered heteroaryl;
• R27, R28, R29 and R30, at each occurrence, each independently is selected from hydrogen and C1-6 alkyl;
• and
• p, and q, at each occurrence, each independently is selected from 1, 2, 3, 4, 5 and;
• wherein the FAAH-mediated disorder is a pain disorder, or an inflammatory disorder.