Quinoline and quinazoline derivatives having affinity for 5HT1-type receptors

A process for the preparation of a compound of formula (I) or a pharmaceutically acceptable salt thereof,

• wherein:
• n, p, and q are each 0, such that R2, W, and R5 are absent;
• m is 1;
• Y and Z are each —CH2—;
• R1 is halogen, cyano, C1-6alkyl, C1-6alkoxy, haloC1-6alkoxy or haloC1-6alkyl;
• X is N or CH;
• and
• R3 and R4 are independently hydrogen, C1-6alkyl, C1-6alkylsulfonyl, a group having the formula (IIa):
• wherein A is oxygen or sulfur, D is —(CH2)t—, —(CH2)tO— or —O(CH2)t—, wherein t is 0, 1, 2, 3 or 4;
• and E is C1-6alkyl;
• C3-7cycloalkyl, optionally substituted by one or more substituents independently selected from halogen, hydroxy, oxo, C1-6alkyl, cyano, CF3, OCF3, C1-6alkoxy and C1-6alkanoyl;
• or aryl, optionally substituted by one or more substituents independently selected from halogen, C1-6alkyl, CF3, cyano, hydroxy, C1-6alkanoyl, and C1-6alkoxy;
• or a group having the formula (IIb)
• wherein A is oxygen or sulfur, D is —(CH2)t—, —(CH2)tO— or —O(CH2)t—, wherein t is 0, 1, 2, 3 or 4;
• and E is C1-6alkyl;
• C3-7cycloalkyl, optionally substituted by one or more substituents independently selected from halogen, hydroxy, oxo, C1-6alkyl, cyano, CF3, OCF3, C1-6alkoxy and C1-6alkanoyl;
• or aryl optionally substituted by one or more substituents independently selected from halogen, C1-6alkyl, CF3, cyano, hydroxy, C1-6alkanoyl, and C1-6alkoxy;
• or R3 and R4, together with the nitrogen atom to which R3 and R4 are attached, combine to form a 3-7 membered monocyclic heterocyclic group or a 8-11 membered bicyclic heterocyclic group, wherein each group is optionally substituted by one or more substituents selected from halogen, oxo, C1-6alkyl, cyano, CF3,
• C1-6alkoxy, C1-6alkanoyl, aryl and arylC1-6alkyl, wherein the aryl and arylC1-6alkyl are further optionally substituted by one or more halogen, oxo, C1-6alkyl, cyano, CF3,
• C1-6alkoxy and C1-6alkanoyl;
• which process comprises reacting a compound of formula (VII):
• wherein R1, m, X, R2 and n are as defined for formula (I), with a compound of formula (VIII):
• wherein W, p, Y, Z, R5, q, R3 and R4 are as defined for formula (I), and L is selected from the group consisting of chloro, bromo, iodo, tosylate, brosylate, nosylate, mesylate, fluorosulfonate, triflate, nonaflate, and tresylate;
• in the presence of a base, and thereafter optionally:
• removing any protecting groups and/or
• forming a pharmaceutically acceptable salt.