Patent CA-2049490-A1 (CA)
Title: Pyrrolobenzimidazoles, imidazobenzoxazinones and imidazoquinolones, process for their preparation and their use and preparations containing the compounds
Inventor: PAAL MICHAEL
IPC: A61K31/415
Filed: 1991-08-19
Abstract: Abstract Compounds of the formula I                                               (I) in which X can have the meaning Xa, Xn1, Xb or Xc, and in which in the case a), in which X has the meaning Xa, Xa denotes the methylene group -CH2-, and R1 has the meaning R1a and R1a is hydrogen, C16-alkyl, C2-6-alkenyl or C3-7-cycloalkyl and R2 has the meaning R2a and R2a  denotes  hydrogen,  C1-6-alkyl,  C2-6-alkenyl  or  C1-6-hydroxyalkyl, where R1a and R2a can be identical or dif-ferent, or R1a and R2a, together with the carbon atom included by them, denote C3-7-spiroalkyl, R3 denotes hydrogen or C1-6-alkyl, R4 has the meaning R4a and R4a denotes the cyanamido group, the 4-difluoromethoxy-3-pyridyl group or a C1-2-nitroalkyl group and Z denotes oxygen or sulphur, and in which in the case a1), in which X has the meaning Xa1, Xa1 together with R1, which in this  case has the meaning R1a1, denotes the group -CH= and R2 has the meaning R2a1 and R2a1 is hydrogen or C1-6-alkyl, R3 is hydrogen or C1-6-alkyl, R4 has the meaning R4a1 and R4a1 denotes the cyanamido group, the 4-difluoromethoxy-3-pyridyl group, a C1-2-nitroalkyl group, hydrogen, the hydroxyl group, a mercapto, C1-6-alkylmercapto, an amino, pyridylcarbonylamino,C1-6-alkylcarbonylamino,a C1-6-alkyl, C3-7-cycloalkyl, C2-6-alkenyl, C3-7-cycloalkenyl, C2-6-alkynyl or C1-6-haloalkyl group or a phenyl ring of the general formula II                                 (II) in which R5, R6 and R7 can be identical or different and in each case can be hydrogen, a C1-6-alkanesulphonyloxy, trifluoromethanesulphonyloxy,  C1-6-alkanesulphonylamino, trifluoromethanesulphonylamino,   N-C1-6-alkyl-C1-6-alkyl-sulphonylamino,    N-C1-6-alkyltrifluoromethanesulphonyl-amino, C1-6-alkylsulphenylmethyl, C1-6-alkylsulphinylmethyl or  C1-6-alkylsulphonylmethyl  group,  a  carbonyl  group substituted by a hydroxyl, C1-6-alkoxy, amino, C1-6-alkyl-amino or  C2-12-alalkylamino  group,  a  sulphonyl  group substituted by an amino, C1-6-alkylamino, C2-12-dialkylamino or cyclic imino group, in which a methylene group in the 4-position can be replaced by a sulphur or oxygen atoms a C1-6-alkylcarbonylamino,  aminocarbonylamlno  or  C1-6-alkylaminocarbonylamino  group,   a  C1-6-alkylmercapto, C1-6-alkylsulphinyl or C1-6-alkylsulphonyl group, a nitro, halogen,  amino,  hydroxyl,  C1-6-alkyl,  C1-6-alkoxy,  C1-6-alkenyloxy,  C1-6-alkynyloxy,  cyano-C1-6-alkoxy,  carboxy-C1-6-alkoxy, C1-6-alkoxycarbonyl-C1-6-alkoxy, C2-C12-dialkyl-amino, 1-imidazolyl, trifluoromethyl or cyano group, rr R4a1 denotes a naphthyl radical or R4a1 represents a saturated or unsaturated heterocyclic five-membered ring having 1-4 heteroatoms or a saturated or unsaturated heterocyclic six-membered ring having 1-5 heteroatoms, in which the heteroatoms can be identical or different and denote oxygen, sulphur or nitrogen and if desired can carry an oxygen atom on one or more nitrogen atoms, and the five-membered or six-membered ring  can optionally be substituted by one or more C1-6-alkyl, C1-6-alkoxy,   C1-6-alkylmercapto, hydroxyl,  nitro,  amino, halogen or cyano groups or can be condensed with a phenyl ring to give a bicyclic compound and Z denotes oxygen or sulphur, and in which in the case b), in which X has the meaning Xb, Xb denotes oxygen and R1 has the meaning R1b and R2 the meaning R2b and R1b and R2b, which can be identical or different, in each case stand for hydrogen or C1-6-alkyl, R3 denotes hydrogen or C1-6-alkyl, R4 has the meaning R4b and R4b  is  the  cyanamido  group,  the  4-difluoromethoxy-3-pyridyl group or a C1-2-nitroalkyl group and Z denotes oxygen or sulphur, and in which in the case c), in which X has the meaning Xc, Xo denotes a bond and R1 has the meaning R1c and R1c is hydrogen, C1-6-alkyl, C2-6-alkenyl or C3-7-cycloalkyl and R2 has the meaning R2c and R2a  denotes  hydrogen,  C1-6-alkyl, C2-6-alkenyl  or  C1-6-hydroxyalkyl, in which R1c and R2c can be identical or different, or R1c and R2c, together with the carbon atom included by them, denote C3-7-spiroalkyl, R3 denotes hydrogen or C1-6-alkyl, R4 has the meaning R4c and R4c  is  the  cyanamido  group,  the  4-difluoromethoxy-3-pyridyl group or a C1-2-nitroalkyl group and Z denotes oxygen or sulphur, and their salts and acid addition salts, tautomers and optical isomers are PDE-III and PDE-IV inhibitors.