7-substituted derivatives of 3,5-dihydroxyhept-6-ynoic acid,...

Details 7-substituted derivatives of 3,5-dihydroxyhept-6-ynoic acid,... 7-substituted derivatives of 3,5-dihydroxyhept-6-ynoic acid,...

C - Chemistry, Metallurgy

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167/179, 260/251

C07C 59/56 (2006.01) A61K 31/44 (2006.01) C07C 33/48 (2006.01) C07C 45/30 (2006.01) C07C 47/24 (2006.01) C07D 207/333 (2006.01) C07D 207/337 (2006.01) C07D 213/48 (2006.01) C07D 213/55 (2006.01) C07D 237/08 (2006.01) C07D 239/26 (2006.01) C07D 309/30 (2006.01) C07D 405/06 (2006.01)

Patent

CA 1340047

7-Substituted derivatives of 3,5-dihydroxyhept-6-ynoic acid, a process for the preparation thereof, the use thereof as pharmaceuticals, and intermediates 7-Substituted 3,5-dihydroxyhept-6-ynoic acids and the derivatives thereof of the formula I (see fig. I) as well as the corresponding lactones of the formula II (see fig. II) in which R denotes a) a radical of the formula a (see fig. III) in which R1 and R2 are, independently of one another, a straight-chain or branched alkyl or alkenyl radical having up to 6 carbon atoms, a saturated or up to doubly unsaturated cyclic hydrocarbon radical having 3-6 carbon atoms or phenyl radical which is optionally substituted by 1-3 identical or different radicals selected from the group comprising straight-chain or branched alkyl having up to 4 carbon atoms, halogen, alkoxy having up to 4 carbon atoms and hydroxyl, and X=Y-Z is a group of the formula CR3=CR4-CR5, N=CR4-CR5, N=N-CR5, N=CR4-N, in which R3, R4, R5 are, independently of one another, hydrogen, a straight-chain or branched alkyl or alkenyl radical having up to 6 carbon atoms, a saturated or up to doubly unsaturated cycllc hydrocarbon radical having 3-6 carbon atoms or a phenyl radical which is optionally substituted by 1-3 identical or different radicals selected from the group comprising straight-chain or branched alkyl having up to 4 carbon atoms, halogen, alkoxy having up to 4 carbon atoms and hydroxyl, b) a radical of the formula b Image in which R6 and R7 are, independently of one another, a straight-chain or branched alkyl or alkenyl radical having up to 6 carbon atoms, a saturated or up to doubly unsaturated cyclic hydrocarbon radical having 3-6 carbon atoms, a phenyl radical which is optionally substituted by 1-3 identical or different radicals selected from the group comprising straight-chain or branched alkyl having up to 4 carbon atoms, halogen and alkoxy having up to 4 carbon atoms, and U-V-W is a group of the formula C-NR9-CR8, C-O-CR8, C-S-CR8, C-NR9-N , C-O-N (= C-N-O ), C-S-N ( = C-N-S ), N-CR10=CR8 , N-N=CR8 or N-CR10=N, in which R8 is hydrogen, a straight-chain or branched alkyl or alkenyl radical having up to 6 carbon atoms, a saturated or up to doubly unsaturated eyclic hydrocarbon radical having 3-6 carbon atoms or a phenyl radical which is optionally substituted by 1-3 identical or different radicals selected from the group comprising straight-chain or branched alkyl having up to 4 carbon atoms, halogen, alkoxy having 1-4 carbon atoms and hydroxyl, and R9, R10 are, independently of one another, a straight-chain or branched alkyl or alkenyl radical having up to 6 carbon atoms, a saturated or up to doubly unsaturated cyclic hydrocarbon radical having 3-6 carbon atoms or a phenyl radical which is optionally substituted by 1-3 identical or different radicals selected from the group comprising straight-chain or branched alkyl having up to 4 carbon atoms, halogen and alkoxy having up to 4 carbon atoms, or e) a radical of the formula c Image in which A-B is a group of the formula CH-CH or C=C, and R11, R12, R13 are, independently of one another, a straight-chain or branched alkyl or alkenyl radical having up to 20 carbon atoms, a saturated or up to doubly unsaturated cyclic hydrocarbon radical having 3-6 carbon atoms or a phenyl radical which is optionally substituted by 1-3 radicals selected from the group comprising straight-chain or branched alkyl having up to 4 carbon atoms, halogen, alkoxy having up to 4 carbon atoms and hydroxyl, and R~ denotes hydrogen, a straight-chain or branched alkyl radical having up to 6 carbon atoms, alkali metal or ammonium, a process for the preparation of these compounds, the use thereof as pharmaceuticals and pharmaceutical products are described. In addition, new intermediates for the preparation of the compounds of the formula I or formula II are described.

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