Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-05-01
1997-02-25
Fan, Jane
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D21186
Patent
active
056060661
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/EP93/01720 filed Jul. 3, 1993 now WO94/01405
BACKGROUND OF THE INVENTION
The present application relates to light-activable 1-(2-nitrobenzyl) substituted 1,4-dihydropyridines, important intermediates for releasing highly effective 1,4-dihydropyridines, as well as a process for preparing the same. It is already known that 1-benzyl-substituted 1,4-dihydropyridines are used as chemotherapeutics (EP 330 470-A). See also DT 1,963,188-Q (17.12.69).
SUMMARY OF THE INVENTION
The present application relates to light-activable 1-(2nitrobenzyl) substituted 1,4-dihydropyridines, important intermediates for releasing highly effective 1,4-dihydropyridines, as well as a process for preparing the same. The compounds may be used for observing biological, physiological and pharmacological activities. For example, the invention provides an approach for the synthesis of Ca-agonistic and Ca-antagonistic 1,4-dihydropyrimidines for monitoring calcium channel activity.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 shows the changes in force of muscle contraction after flash-activation of Ca-antagonist.
FIG. 2 shows the changes in force of muscle contraction after flash-activation of Ca-agonist.
DETAILED DESCRIPTION OF THE INVENTION
The invention is related to light-activable 1-(2-nitrobenzyl) substituted 1,4-dihydropyridines of the general formula (I) ##STR1## in which R1 represents hydrogen, cyano, formyl, hydrooxymethyl, methyl or aminoethoxymethyl; R2 represents cyano, nitro or a radical of the formula --CO--O--A, in which A represents a straight-chain or branched alkyl or alkenyl radical with 1 to 10 carbon atoms, which are optionally substituted by methylthio, methoxy, ethoxy, hydroxy or a benzyl-N(CH.sub.3)--CH.sub.2 --CH.sub.2 -radical, or R1 and R2 together represent a lactone-ring of the formula (2) ##STR2## R3 represents an aryl radical with 6 to 10 carbon atoms or a 5 to 7 membered unsaturated heterocyclic ring with up to 2 heteroatoms of the group S, N or O, both of which are optionally substituted by 1 to 3 identical or different substituents selected from halogen, nitro, trifluoromethyl, cyano, difluoromethoxy, a straight-chain or branched alkyl, alkoxy or alkylthio (each with 1 to 8 carbon atoms), benzyl, benzylthio, benzyloxy or phenoxy, or R3 represents a radical of the formula (3) ##STR3## in which B represents O or S; R4 represents a straight-chain or branched alkyl or alkenyl radical with 1 to 10 carbon atoms, which are optionally substituted by methylthio, methoxy, ethoxy, hydroxy or a benzyl-N(CH.sub.3)--CH.sub.2 --CH.sub.2 -radical; and R5 represents hydrogen, F--, Cl-- Br--, hydroxy, carboxy-, a straight chain or branched alkyl, alkoxy- or alkoxycarbonyl radical, each with 1 to 8 carbon atoms, and salts thereof.
Compounds of the general formula (I) can be obtained as racemic mixtures or in the form of pure enantiomers.
Compounds of the general formula (I) are preferred, in which R1 represents hydrogen, cyano, hydrooxymethyl, methyl or aminoethoxymethyl; R2 represents cyano, nitro or a radical of the formula --CO--O--A, in which A represents a straight-chain or branched alkyl or alkenyl radical with 1 to 5 carbon atoms, which are optionally substituted by methoxy, ethoxy, hydroxy or a benzyl-N(CH.sub.3)--CH.sub.2 --CH.sub.2 -radical, or R1 and R2 together represent a lactone-ring of the formula (2) ##STR4## R3 represents phenyl, naphthyl, o-pridyl, m-pyridyl, p-pyridyl or thienyl which are optionally substituted by 1 to 2 identical or different substituents selected from fluorine, chlorine, bromine, nitro, trifluoromethyl, a straight-chain or branched alkyl, alkoxy or alkylthio (each with 1 to 6 carbon atoms), benzyl, benzylthio, benzyloxy or R3 represents a radical of the formula (3) ##STR5## in which B represents O or S; R4 represents a straight-chain or branched alkyl or alkenyl radical with 1 to 5 carbon atoms, which are optionally substituted by methoxy, ethoxy, hydroxy or a benzyl-N(CH.sub.3)--CH.sub.2 --CH.sub.2 -radical; and R5 represents hydrogen, F--, Cl-- Br--, hydroxy
Bechem Martin
Goldmann Siegfried
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