Patent HU-9903443-A3 (HU)
Title: Aralkyl and aralkylidene heterocyclic lactams and imides
Filed: 1997-09-08
Abstract: Aralkyl and aralkylidene heterocyclic lactam and imide derivatives of formula (I), and their salts, are new: R1 = G1-G7; a = 0-8; R13 = 1-4C alkyl or a 1-4C methylene bridge from one of the C atoms of the piperazine or piperidine ring of G1 or G2 to the same or another ring C or ring N of the piperazine or piperidine ring of G1 or G2, having a bonding site, or to a ring C of R6 having a bonding site; E = O, S, SO or SO2; X = H, Cl, F, Br, I, CN, 1-6C alkyl, OH, CF3, 1-6C alkoxy, SOt(1-6C alkyl) (where t = 0-2), COOR10 or CONR11R12; Y = optionally substituted 1-4C heteroalkyl bridge that, together with the atoms to which it is attached, forms a 5-7 membered heterocycle containing 2-4 heteroatoms selected from 1,3-oxazolidin-4-on-5-yl, 1,3-oxazolidin-2,4-dion-5-yl, 4,5-dihydro-1,2-oxazolidin-3-on-4-yl, 1,3-thiazolidin-4-on-5-yl, 1,3-thiazolidin-2,4-dion-5-yl, 1,3-pyrazolidin-4-on-5-yl, 1,3-imidazolidin-2,4-dion-5-yl, 1,2-pyrazolidin-3-on-4-yl, 1,2-thiazolidin-1,1,3-trion-4-yl, 1,2-thiazolidin-3-on-4-yl, tetrahydro-1,2-oxazin-3-on-4-yl, tetrahydro-1,3-oxazin-4-on-5-yl, tetrahydro-1,3-oxazin-2,4-dion-5-yl, morpholin-3-on-2-yl, morpholin-3,5-dion-2-yl, 2,3-dihydro-1,4-oxazin-3-on-2-yl, tetrahydro-1,3-thiazin-4-on-5-yl, tetrahydro-1,3-thiazin-2,4-dion-5-yl, tetrahydro-1,2-thiazin-3-on-4-yl, thiomorpholin-3-on-2-yl, thiomorpholin-3,5-dion-2-yl, 2,3-dihydro-1,4-thiazin-3-on-2-yl, hexahydro-1,2-diazin-3-on-4-yl, 4, 5-dihydro-2H-pyridazin-3-on-4-yl, hexahydro-1,3-diazin-4-on-5-yl, hexahydro-1,3-diazin-2,4-dion-5-yl, piperazin-2-on-3-yl, piperazin-2,6-dion-3-yl, tetrahydro-1,3,4-thiadiazin-5-on-6-yl, 5,6-dihydro-1,3,4-thiadiazin-5-on-6-yl, 1,3,4-oxadiazin-5-on-6-yl, 5,6-dihydro-1,2,4-oxadiazin-5-on-6-yl, tetrahydro-1,2,4-oxadiazin-5-on-6-yl, 1,2,4-triazin-5-on-6-yl, tetrahydro-1,2,4-oxadiazin-5-on-6-yl, 5,6-dihydro-1,2,4-oxadiazin-5-on-6-yl, l,2,4-oxadiazin-3,5-dion-6-yl, 1,2,4-triazin-6-on-5-yl, hexahydro-1,2-oxazepin-3-on-2-yl, hexahydro-1,3-oxazepin-4-on-5-yl, hexahydro-1,4-oxazepin-3-on-2-yl, hexahydro-1,4-oxazepin-3,5-dion-2-yl, hexahydro-1,4-oxazepin-3,5-dion-6-yl, 2,3,5,6-tetrahydro-1,4-oxazepin-5,7-dion-6-yl, hexahydro-1,4-oxazepin-5-on-6-yl, hexahydro-1,3-oxazepin-2,4-dion-5-yl, hexahydro-1,2-thiazepin-3-on-4-yl, hexahydro-1,4-thiazepin-3-on-2-yl, 2,3,4,5-tetrahydro-1,4 -thiazepin-3-on-2-yl, hexahydro-1,4-thiazepin-3,5-dion-2-yl, hexahydro-1,4-thiazepin-3,5-dion-6-yl, 2,3,6,7-tetrahydro-1,4-thiazepin-5-on-6-yl, 6,7-dihydro-1,4-thiazepin-5-on-6-yl, hexahydro-1,3-thiazepin-2,4-dion-5-yl, hexahydro-1,2-diazepin-3-on-4-yl, hexahydro-1,3-diazepin-2,4-dion-5-yl, hexahydro-1,4-diazepin-2-on-3-yl, hexahydro-1,4-diazepin-5-on-6-yl, hexahydro-1,4-diazepin-5,7-dion-6-yl, hexahydro-1,3,5-thiadiazepin-3-on-7-yl, 4,5,6,7-tetrahydro-1,3,5-thiadiazepin-6-on-7-yl, 2,3,5,6-tetrahydro-1,2,4-triazepin-3,5-dion-7-yl; where the substituents on any of the C atoms capable of supporting an additional bond, of the heteroalkyl bridge, are Cl, F, 1-6C alkyl, 1-6C alkoxy, CF3 or CN; where the substituents on any of the N atoms capable of supporting an additional bond, of the heteroalkyl bridge, are 1-6C alkyl or CF3; R2 = H, 1-4C alkyl, Ph or naphthyl (Ph or naphthyl being optionally substituted by F, Cl, Br, I, 1-6C alkyl, 1-6C alkoxy, CF3, CN or SOk(1-6C alkyl); k = 0-2; R3 = (CH2)mB; m = 0-3; B = H; or is Ph, naphthyl or a 5-6 membered heteroaryl group containing 1-4 heteroatoms in the ring (all optionally substituted by F, Cl, Br, I, 1-6C alkyl, 1-6C alkoxy, (1-6C alkoxy)-(1-6C alkyl), CF3, OCF3, CN, OH, COOH or SOn(1-6C alkyl); n = 0-2; R6 = H, 1-6C alkyl optionally substituted by 1-6C alkoxy or 1-3 F atoms, or (1-4C alkyl)aryl where the aryl moiety = Ph, naphthyl or heteroaryl-(CH2)q, where the heteroaryl moiety is selected from pyridyl, pyrimidyl, benzoxazolyl, benzothiazolyl, benzisoxazolyl and benzisothiazolyl; and where the aryl and heteroaryl moieties may be substituted by one or more of F, Cl, Br, I, 1-6C alkyl, 1-6C alkoxy, CF3, CN and SOg(1-6C alkyl); g = 0-2; q = 0-4; R7 = H, 1-6C alkyl, (1-4C alkyl)aryl where the aryl moiety is Ph, naphthyl or heteroaryl-(CH2)r, where the heteroaryl moiety is selected from pyridyl, pyrimidyl, benzoxazolyl, benzothiazolyl, benzisoxazolyl and benzisothiazolyl; and where the aryl and heteroaryl moieties may be substituted by F, Cl, Br, I, 1-6C alkyl, 1-6C alkoxy, CF3, C(=O)(1-6C alkyl), CN or SOj(1-6C alkyl); r = 0-4; j = 0-2; or R6+R7 = a 2-4C chain; R8 = H or 1-3C alkyl; R9 = H or 1-6C alkyl; or NR6R9 = 5-7 membered heteroalkyl ring containing 0-4 heteroatoms selected from N, S and O; p = 1-3; R10, R11, R12 = as for R2; or NR11R12 = a 5-7 membered heteroalkyl ring containing 0-4 heteroatoms selected from N, S and O; and the dashed lines = optional bonds; provided that when the dashed line in G2 gives a double bond, R8 is absent. Also claimed are compounds of formula (V).