3-Substituted-4-aminoalkoxy-5,6-condensed ring-2-pyranones
AssigneeLipha, Lyonnaise Industrielle Pharmaceutique
InventorsPhilippe Briet, Jean-Jacques Berthelon, Jean-Claude Depin
Life of this patent
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Abstract
Novel 3-substituted-4-aminoalkoxy-5,6-condensed ring-2-pyranones are disclosed as having utility as pharmacologically active compounds, in particular vasodilatory, hypotensive, anti-ischemic and anti-tussive activity. The compounds may be 3-phenyl-4-morpholinoalkoxy-coumarins. Administration may be by the oral or parenteral route. Intermediates useful in the production of these compounds are also disclosed.
Claims6
A substituted pyranone represented by the formula:
- ##STR55## or a pharmaceutically acceptable acid addition salt thereof, wherein:
- n is 0 or 1;
- n.sub.1 is 0 or 1;
- R is lower alkyl, phenyl, phenyl substituted by at least one halogen atom or lower alkoxy group, or benzyl;
- R.sub.1 is hydrogen, a hydroxy or lower alkyl group, or a 3,4,5-trialkoxybenzoyloxy radical;
- R.sub.2 is a straight-chain or branched lower alkyl group;
- R.sub.3 is hydrogen or lower alkyl;
- or
- R.sub.1 and R.sub.2 are joined together to form with the adjacent nitrogen atom a saturated heterocyclic ring with n being 1 and n.sub.1 being 0, or
- R.sub.2 and R.sub.3 are joined together to form with the adjacent nitrogen atom a saturated heterocyclic ring optionally containing a further hetero atom;
- X is benzene, cyclohexene, cycloheptene, cyclooctaene, cyclododecaene, naphthalene, dihydronaphthalene, or indeno (2,1-6) pyrano;
- R.sub.4 is H, halogen, hydroxy, lower alkyl, lower alkoxy, morpholinoalkoxy or phenyl;
- R.sub.5 is H, a substituent selected from hydroxy, straight-chain or branched lower alkyl, lower alkoxy and morpholinoalkoxy groups;
- R.sub.6 is hydrogen or a lower alkyl group;
- R.sub.7 is hydrogen or a lower alkyl group;
- and
- R.sub.8 is hydrogen or a lower alkyl group.
A substituted pyranone represented by the formula:
- ##STR56## or a pharmaceutically acceptable acid addition salt thereof, wherein:
- n is 0 or 1;
- n.sub.1 is 0 or 1;
- R is lower alkyl, phenyl, phenyl substituted by at least one halogen atom or lower alkoxy group, or benzyl;
- R.sub.1 is H, OH, lower alkyl or 3,4,5-trialkoxybenzoyloxy;
- R.sub.2 and R.sub.3 together form morpholino;
- X represents a benzene, cyclohexene, cycloheptene, cyclooctaene, cyclododecaene, naphthalene, dihydronaphthalene, 2-phenylindene or diphenyl ring;
- R.sub.4 is H, halogen, OH, lower alkyl, lower alkoxy or phenyl;
- R.sub.5 is H, OH, lower alkyl or lower alkoxy;
- R.sub.6 is hydrogen or a lower alkyl group;
- R.sub.7 is hydrogen or a lower alkyl group;
- and
- R.sub.8 is hydrogen or a lower alkyl group.
A substituted pyranone represented by the formula:
- ##STR57## or a pharmaceutically acceptable acid addition salt thereof, wherein:
- n is 0 or 1;
- n.sub.1 is 0 or 1;
- R is phenyl;
- R.sub.1 is hydrogen, a hydroxy or lower alkyl group, or a 3,4,5-trialkoxybenzoyloxy radical;
- R.sub.2 and R.sub.3 are joined together to form with the adjacent nitrogen atom a morpholino ring;
- X represents a benzene, cyclohexene, cycloheptene, cyclooctaene, cyclododecaene, naphthalene, dihydronaphthalene, 2-phenylindene or diphenyl ring;
- R.sub.4 is H, OH, lower alkyl or lower akoxy;
- and
- R.sub.5 is H, OH, lower alkyl or lower alkoxy.
A substituted pyranone represented by the formula:
- ##STR58## or a pharmaceutically acceptable acid addition salt thereof, wherein:
- n is 0 or 1;
- n.sub.1 is 0 or 1;
- R is phenyl;
- R.sub.1 is hydrogen, a hydroxy or lower alkyl group;
- or a 3,4,5-trialkoxybenzoyloxy radical;
- R.sub.2 and R.sub.3 are joined together with the adjacent nitrogen to form morpholino or piperidino;
- X is cyclohexene, cycloheptene, cyclooctaene or cyclododecaene;
- R.sub.4 is H, halogen, OH, lower alkyl, lower alkoxy or phenyl;
- and
- R.sub.5 is H, OH, lower alkyl or lower alkoxy.
Dependencies are inferred from the claim text.