(1H-azol-1-ylmethyl)substituted quinoline derivatives

Claim 2

A compound of the formula: ##STR37## a pharmaceutically acceptable acid addition salt thereof or a stereochemically isomeric form thereof, wherein: --X 1 =X 2 -- represents a bivalent radical of formula --CH═CH-- (x), --CH═N-- (y), or --N═CH-- (z); R represents hydrogen or C 1-6 alkyl; Y represents hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, Ar 1 , Ar 2 --C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl; and Z represents a radical of the formula: ##STR38## wherein: R 1 and R 4 each independently represent hydrogen, C 1-6 alkyl or Ar 2 C 1-6 alkyl; R 2 and R 5 each independently represent hydrogen, C 1-6 alkyl or Ar 2 ; and R 3 and R 6 each independently represent hydrogen or C 1-6 alkyl, and wherein in the foregoing: Ar 1 represents phenyl, substituted phenyl, naphthalenyl, pyridinyl, imidazolyl, triazolyl, thienyl, furanyl or thiazolyl, and Ar 2 represents phenyl or substituted phenyl, wherein said substituted phenyl in Ar 1 or Ar 2 represents phenyl substituted with 1, 2 or 3 substituents each independently selected from the group consisting of halo, hydroxy, trifluoromethyl, C 1-6 alkyl, C 1-6 alkyloxy, cyano, amino, mono- and di(C 1-6 alkyl)amino, nitro, carboxyl, formyl and C 1-6 alkyloxycarbonyl, provided that: when (1) --X 1 ═X 2 --represents a bivalent radical of formula --CH═CH--, (2) R represents hydrogen, and (3) R 1 , R 2 , R 3 , R 4 , R 5 and R 6 all represent hydrogen, then Y is other than hydrogen, C 1-10 alkyl, Ar 1 or Ar 2 C 1-6 alkyl.

Claim 3

A compound according to claim 1 wherein R is hydrogen or C 1-4 alkyl; Y is hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl, phenyl, substituted phenyl, pyridinyl, imidazolyl or thienyl and R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently are hydrogen or C 1-4 alkyl.

Claim 4

A compound according to claim 2 wherein --X 1 ═X 2 -- is a radical of formula (x) or (y); and Y is hydrogen, C 1-4 alkyl, cyclopropyl, cyclopentyl, cyclohexyl, imidazolyl, pyridinyl, thienyl or phenyl optionally substituted with one or two substituents each independently selected from halo, C 1-4 alkyl, C 1-4 alkyloxy and trifluoromethyl.

Claim 5

A compound according to claim 3 wherein: Z is a radical of formula (a-1) wherein R 1 and R 2 are hydrogen, R 3 is hydrogen or C 1-4 alkyl and Y is hydrogen, C 1-4 alkyl or phenyl optionally substituted with one or two halo atoms; or Z is a radical of formula (a-2) wherein R 4 , R 5 and R 6 all are hydrogen, and Y is hydrogen, C 1-4 alkyl, cyclopropyl or phenyl optionally substituted with one or two halo atoms.

Claim 6

A compound according to claim 1 wherein Z is a radical of formula (a-1); R is hydrogen; --X 1 ═X 2 -- is a radical of formula (x) or (y); Y is isopropyl, phenyl or halophenyl; R 1 and R 2 are both hydrogen; and R 3 is methyl.

Claim 7

A compound according to claim 1 wherein Z is a radical of formula (a-2); R is hydrogen; --X 1 ═X 2 -- is a radical of formula (x) or (y); Y is cyclopropyl, phenyl or halophenyl; and R 4 , R 5 and R 6 are all hydrogen.

Claim 8

A compound according to claim 1 wherein the compound is 6-[(4-fluorophenyl) (1H-imidazol-1-yl)methyl]-2(1H)-quinolinone, a pharmaceutically acceptable acid addition salts or a possible stereoisomeric form thereof.

Claim 9

A compound according to claim 1 wherein the compound is 6-[(3-chlorophenyl) (1H-imidazol-1-yl)methyl]-3,4-dihydro-2(1H)-quinolinone, a pharmaceutically acceptable acid addition salt or a possible stereoisomer thereof.

Claim 10

A compound according to claim 1 wherein the compound is 3,4-dihydro-6-[(1H-imidazol-1-yl)phenylmethyl]-2(1H)-quinolinone, a pharmaceutically acceptable acid addition salt or a possible stereoisomer thereof.

Claim 11

A composition comprising an inert carrier and, if desired, other additives, and as active ingredient an effective amount of a compound of the formula: ##STR39## a pharmaceutically acceptable acid addition salt thereof or a stereochemically isomeric form thereof, wherein: --X 1 ═X 2 -- represents a bivalent radical of formula --CH═CH-- (x), --CH═N-- (y), or --N═CH-- (z); R represents hydrogen or C 1-6 alkyl; Y represents hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, Ar 1 , Ar 2 --C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl; and Z represents a radical of the formula: ##STR40## wherein: R 1 and R 4 each independently represent hydrogen, C 1-6 alkyl or Ar 2 C 1-6 alkyl; R 2 and R 5 each independently represent hydrogen, C 1-6 alkyl or Ar 2 ; and R 3 and R 5 independently represent hydrogen or C 1-6 alkyl, and wherein in the foregoing: Ar 1 represents phenyl, substituted phenyl, naphthalenyl, pyridinyl, imidazolyl, triazolyl, thienyl, furanyl or thiazolyl, and Ar 2 represents phenyl or substituted phenyl, wherein said substituted phenyl in Ar 1 or Ar 2 represents phenyl substituted with 1, 2 or 3 substituents each independently selected from the group consisting of halo, hydroxy, trifluoromethyl, C 1-6 alkyl, C 1-6 alkyloxy, cyano, amino, mono- and di(C 1-6 alkyl)amino, nitro, carboxyl, formyl and C 1-6 alkyloxycarbonyl, provided that: when (1) --X 1 ═X 2 -- represents a bivalent radical of formula --CH═CH--, (2) R represents hydrogen, and (3) R 1 , R 2 , R 3 R 4 , R 5 and R 6 all represent hydrogen, then Y is other than hydrogen, C 1-10 alkyl, Ar 1 or Ar 2 C 1-6 alkyl.

Claim 12

A composition comprising an inert carrier and, if desired, other additives, and as active ingredient an effective amount of a compound of the formula: ##STR39## a pharmaceutically acceptable acid addition salt thereof or a stereochemically isomeric form thereof, wherein: --X 1 ═X 2 -- represents a bivalent radical of formula --CH═CH-- (x), --CH═N-- (y), or --N═CH-- (z); R represents hydrogen or C 1-6 alkyl; Y represents hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, Ar 1 , Ar 2 --C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl; and Z represents a radical of the formula: ##STR40## wherein: R 1 and R 4 each independently represent hydrogen, C 1-6 alkyl or Ar 2 C 1-6 alkyl; R 2 and R 5 each independently represent hydrogen, C 1-6 alkyl or Ar 2 ; and R 3 and R 5 independently represent hydrogen or C 1-6 alkyl, and wherein in the foregoing: Ar 1 represents phenyl, substituted phenyl, naphthalenyl, pyridinyl, imidazolyl, triazolyl, thienyl, furanyl or thiazolyl, and Ar 2 represents phenyl or substituted phenyl, wherein said substituted phenyl in Ar 1 or Ar 2 represents phenyl substituted with 1, 2 or 3 substituents each independently selected from the group consisting of halo, hydroxy, trifluoromethyl, C 1-6 alkyl, C 1-6 alkyloxy, cyano, amino, mono- and di(C 1-6 alkyl)amino, nitro, carboxyl, formyl and C 1-6 alkyloxycarbonyl, provided that: when (1) --X 1 ═X 2 -- represents a bivalent radical of formula --CH═CH--, (2) R represents hydrogen, and (3) R 1 , R 2 , R 3 R 4 , R 5 and R 6 all represent hydrogen, then Y is other than hydrogen, C 1-10 alkyl, Ar 1 or Ar 2 C 1-6 alkyl.

Claim 13

A composition according to claim 10 wherein R is hydrogen or C 1-4 alkyl; Y is hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl, phenyl, substituted phenyl, pyridinyl, imidazolyl or thienyl and R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently are hydrogen or C 1-4 alkyl.

Claim 14

A composition according to claim 11 wherein --X 1 ═X 2 -- is a radical of formula (x) or (y); and Y is hydrogen, C 1-4 alkyl, cyclopropyl, cyclopentyl, cyclohexyl, imidazolyl, pyridinyl, thienyl or phenyl optionally substituted with one or two substituents each independently selected from halo, C 1-4 alkyl, C 1-4 alkyloxy and trifluoromethyl.

Claim 15

A composition according to claim 12 wherein: Z is a radical of formula (a-1) wherein R 1 and R 2 are hydrogen, R 3 is hydrogen or C 1-4 alkyl and Y is hydrogen, C 1-4 alkyl or phenyl optionally substituted with one or two halo atoms; or Z is a radical of formula (a-2) wherein R 4 , R 5 and R 6 all are hydrogen, and Y is hydrogen, C 1-4 alkyl, cyclopropyl or phenyl optionally substituted with one or two halo atoms.

Claim 16

A composition according to claim 10 wherein Z is a radical of formula (a-1); R is hydrogen; --X 1 ═X 2 -- is a radical of formula (x) or (y); Y is isopropyl, phenyl or halophenyl; R 1 and R 2 are both hydrogen; and R 3 is methyl.

Claim 17

A composition according to claim 10 wherein Z is a radical of formula (a-2); R is hydrogen; --X 1 ═X 2 -- is a radical of formula (x) or (y); Y is cyclopropyl, phenyl or halophenyl; and R 4 , R 5 and R 6 are all hydrogen.

Claim 18

A composition according to claim 10 wherein the compound is 6-[(4-fluorophenyl) (1H-imidazol-1-yl)methyl]-2(1H)-quinolinone, a pharmaceutically acceptable acid addition salts or a possible stereoisomeric form thereof.

Claim 19

A composition according to claim 10 wherein the compound is 6-[(3-chlorophenyl) (1H-imidazol-1-yl)methyl]-3,4-dihydro-2(1H)-quinolinone, a pharmaceutically acceptable acid addition salt or a possible stereoisomer thereof.

Claim 20

A composition according to claim 10 wherein the compound is 3,4-dihydro-6-[(1H-imidazol-1-yl)phenylmethyl]-2(1H)-quinolinone, a pharmaceutically acceptable acid addition salt or a possible stereoisomer thereof.