Aralkyl-1,4-dihydropyridines, a method for their preparation and

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

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

REFERENCES:
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.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Aralkyl-1,4-dihydropyridines, a method for their preparation and does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Aralkyl-1,4-dihydropyridines, a method for their preparation and, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Aralkyl-1,4-dihydropyridines, a method for their preparation and will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-43738

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.