Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1989-06-22
1991-12-24
Springer, David B.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514 79, 514 89, 5142222, 514252, 514259, 514269, 514307, 514311, 514332, 514338, 514340, 514342, 514343, 514344, 514352, 514335, 544 3, 544238, 544244, 544284, 544333, 544405, 546 22, 546147, 546148, 546152, 546263, 546269, 546271, 546272, 546273, 546274, 546275, 546276, 546280, 546281, 546286, 546310, 546318, 546321, 546322, 546 24, 546261, C07D21190, C07D40106, A61K 31455
Patent
active
050753240
DESCRIPTION:
BRIEF SUMMARY
Object of the present invention are 2-alkyl-substituted-1,4-dihydropyridines, a method for their preparation and pharmaceutical compositions containing them.
The compounds of the invention have the following general formula I ##STR2## wherein:
X is a --CO.sub.2 R.sub.1, cyano, nitro, --COCH.sub.3 group;
R and R.sub.1, that can be the same or different, are a primary, secondary or tertiary, saturated or unsaturated, linear or branched C.sub.1 -C.sub.6 alkyl group that can be substituted or not by one or more hydroxy, C.sub.1 -C.sub.7 -monoalkylamino, di-C.sub.1 -C.sub.7 -alkylamino, benzylamino, C.sub.1 -C.sub.6 -alkoxy, phenoxy groups optionally substituted by one or more C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo-C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.6 -alkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkylthio, NHCOR.sub.5, SO.sub.2 R.sub.6, C.sub.1 -C.sub.4 -alkylamino , di(C.sub.1 -C.sub.4)alkylamino, hydroxy;
R.sub.2 is hydrogen;
R.sub.3 is hydrogen or a hydroxy, --OCOR.sub.5, OSO.sub.2 R.sub.6, azide, amino, --NHPO(OR.sub.7).sub.2, --NHCOR.sub.5 group, a C.sub.1 -C.sub.4 -alkoxy group or a fluorine, chlorine, bromine or iodine atom, a SH group, a SCOR.sub.6 or a C.sub.1 -C.sub.6 -alkylthio, phenylthio or benzylthio group;
R.sub.4 is an optionally substituted aromatic or an optionally substituted 5- or 6-membered heteroaromatic group, containing one or more heteroatoms selected in the group of N,S,O, wherein the substituent is selected from one or more hydroxy, C.sub.1 -C.sub.7 -monoalkylamino, di-C.sub.1 -C.sub.7 -alkylamino, benzylamino, C.sub.1 -C.sub.6 -alkoxy, phenoxy groups optionally substituted by one or more C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo-C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.6 -alkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.6 alkylthio, NHCOR.sub.5, SO.sub.2 R.sub.6, C.sub.1 -C.sub.4 -alkylamino, di(C.sub.1 -C.sub.4)alkylamino, hydroxy;
Y is one or more substituents, that can be the same or different, selected in the group of C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, halo-C.sub.1 -C.sub.6 -alkyl, halo-C.sub.1 -C.sub.6 -alkoxy, NHCOR.sub.5 or NHSO.sub.2 R.sub.6 ;
R.sub.5 is hydrogen or a C.sub.1 -C.sub.4 -alkyl, trihalomethyl, C.sub.1 -C.sub.4 -alkoxy or phenyl group, optionally substituted by one or more nitro, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, amino groups;
R.sub.6 is hydrogen or a C.sub.1 -C.sub.4 -alkyl, trihalomethyl, phenyl or p-methylphenyl group;
R.sub.7 is a C.sub.1 -C.sub.4 -alkyl group or a phenyl group.
Included in the scope of the present invention are pharmaceutically acceptable salts, optical antipodes, i.e. the single enantiomers, their mixtures, the single enantiomers, their mixtures, the single diastereoisomers of formula I and their mixtures.
Pharmaceutically acceptable salts of compounds of formula I are those with pharmaceutically acceptable acids and bases.
Derivatives of 1,4-dihydropyridin-3,5-dicarboxylic acids, having in position 2 a (2-phenyl-2-hydroxy)-ethyl chain are claimed in Japanese Patent Application No. 8564692 Derivatives of 1,4-dihydropyridin-3,5-dicarboxylic acids, substituted in 2 position with a 3-oxo-1-propenyl chain are claimed in German Patent Application No. 2935772. In both cases there are evident structural differences between the cited compounds and the compounds of the present invention.
Alkyl, alkoxy, alkylthio, acyloxy and acylamino groups according to the invention may have both linear or branched chain; an unsaturated alkyl group of R or R.sub.1 may be both a cis- or trans-C.sub.2 -C.sub.6 -alkenyl residue or a C.sub.2 -C.sub.6 -alkynyl residue, preferably propargyl.
According to the present invention, a halo-C.sub.1 -C.sub.6 -alkyl group is preferably trichloromethyl or trifluoromethyl; a halo-C.sub.1 -C.sub.6 -alkoxy group is preferably difluoromethoxy; a C.sub.1 -C.sub.6 -alkyl group is preferably methyl, ethyl, isopropyl or tertbutyl; a
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patent: 4338322 (1982-07-01), Sato
patent: 4492703 (1985-01-01), Goldmann et al.
patent: 4892881 (1990-01-01), Alker et al.
Burger, A., Medical Chemistry, 2nd ed., Interscience, N.Y. (1960), pp. 565-571, 579-581 and 600-601.
Frigerio Marco
Gandolfi Carmelo A.
Germini Mauro
Tofanetti Odoardo
Tognella Sergio
Boehringer Biochemia Robin S.p.A.
Miltenberger Lenora
Springer David B.
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