Cyclized N-substituted-tetrahydropyridine compounds, useful in the treatment of cardiovascular disorders
AssigneeMerck & Co., Inc.
InventorsGeorge D. Hartman, Wasyl Halczenko
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Abstract
Novel cyclized N-substituted tetrahydropyridine compounds are disclosed. The compounds have the property of inhibiting calcium induced contraction of the smooth muscle and are adaptable to being employed in the chemotherapeutic treatment of cardiovascular diseases.
Claims12
A compound having the formula:
- ##STR14## wherein X and X' are independently hydrogen, halogen, lower alkyl, lower alkoxy, nitro or trifluoromethyl;
- R is lower alkyl;
- R' is lower alkyl;
- A is the chain --CH.dbd.CH--Y-- wherein Y is O, S, NH or NR" wherein R" is lower alkyl, and wherein the ends of said chain may be attached to the double bond in either orientation,
- n is 2 or 3;
- and pharmaceutically acceptable salts thereof.
A compound represented by the formula ##STR15## wherein X and X' are independently hydrogen, halogen, lower alkyl, lower alkoxy, nitro or trifluoromethyl;
- R is lower alkyl;
- R' is lower alkyl;
- A is the chain --CH.dbd.CH--O, --CH.dbd.CH--S--, --CH.dbd.CH--NH-- or --CH.dbd.CH--NR" wherein R" is lower alkyl and wherein the ends of said chain may be attached to the double bond in either orientation, and
- n is 2 or 3,
- and pharmaceutically acceptable salts thereof.
A compound which is dimethyl 4,9,10,10a-tetrahydro-7,10a.alpha.-dimethyl-9.beta.-phenyl-5H-thieno[2,3-a ]-quinolizine-8,10.beta.-dicarboxylate hemihydrate.
A compound having the formula ##STR16## wherein X and X' are independently hydrogen, halogen, lower alkyl, lower alkoxy, nitro or trifluoromethyl;
- R is lower alkyl;
- R' is lower alkyl;
- Y is O, S, NH or NR" wherein R" is lower alkyl, and
- n is 2 or 3,
- provided that ##STR17## is joined to --(CH.sub.2).sub.n -- through one of the carbon atoms;
- and pharmaceutically acceptable salts thereof.
A process for preparing a compound having a formula ##STR18## wherein X and X' are independently hydrogen, halogen, lower alkyl, lower alkoxy, nitro or trifluoromethyl;
- R is lower alkyl;
- R' is lower alkyl;
- A is the chain --CH.dbd.CH--Y-- wherein Y is O, S, NH or NR" wherein R" is lower alkyl, and wherein the ends of said chain may be attached to the double bond in either orientation, and
- n is 2 or 3;
- which comprises reacting a compound having the formula ##STR19## wherein X, X', R, R, Y and n are as above defined and wherein ##STR20## is attached to --(CH.sub.2).sub.n -- through one of the carbon atoms, with an acid catalyst in an inert solvent under an inert atmosphere.
A compound having the formula ##STR21## wherein X and X' are independently hydrogen, halogen, lower alkyl, lower alkoxy, nitro or trifluoromethyl;
- R is lower alkyl;
- R' is lower alkyl;
- and pharmaceutically acceptable salts thereof.
A cardiovascular pharmaceutical composition for use in the treatment of cardiovascular diseases caused by high cellular concentration of calcium consisting essentially of from 2-95 percent of a compound of claim 10 in admixture with a pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.