Patent CA-1340047-C (CA)
Title: 7-substituted derivatives of 3,5-dihydroxyhept-6-ynoic acid, a process for the preparation thereof, the use thereof as pharmaceuticals, and intermediates
Inventor: KESSELER KURT
IPC: C07D239/26
Filed: 1989-09-22
Granted: 1998-09-15
Abstract: 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   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   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.