C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 498/04 (2006.01) A61K 31/415 (2006.01) A61K 31/47 (2006.01) A61K 31/535 (2006.01) C07D 471/04 (2006.01) C07D 487/04 (2006.01)
Patent
CA 2049490
Abstract Compounds of the formula I Image (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 Image (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.
Armah Ben
Bruckner Reinhard
Paal Michael
Stenzel Wolfgang
Armah Ben
Beiersdorf Gesellschaft Mit Beschrankter Haftung
Beiersdorf Aktiengesellschaft
Beiersdorf-Lilly Gmbh
Bruckner Reinhard
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