Marion Laboratories

William Ebenezer Solomons

Ian William Mathison

Raymond Henry Jones

Aminoalkylindans of the formula ##STR1## wherein A represents an alkylene group having 2 to 5 carbons in a straight chain, R.sub.1 represents a lower alkyl having 1 to 3 carbons or is a lower alkoxy having 1 to 3 carbons, B represents --CH.sub.2 -- or ##STR2## and R.sub.2 represents phenyl or phenyl-lower alkyl and the phenyl group in such substituents is unsubstituted or is substituted with 1 to 3 lower alkoxy groups, and acid addition salts of the amines. The compounds have hypotensive activity.

Aminoalkylindans and use as hypotensive agents

Provided are compounds of the formula ##STR1## wherein R and R.sub.1 are the same or different lower alkyl groups and R.sub.3 is hydrogen or CHO--.

4,5-Dialkoxy-6 or 7-indanaldehydes

Provided are novel 5-alkoxy-2-alkyl-1,2,3,4-tetrahydroisoquinolines of the formula ##STR1## wherein A is CHO--, HOOC--CH.dbd.CH--, or HOOC--CH.sub.2 --CH.sub.2 --, R and R.sub.1 are the same or different lower alkyl groups, and acid addition salts and quaternary ammonium salts thereof.

5-Alkoxy-2-alkyl-1,2,3,4-tetrahydroisoquinolene-8-carboxaldehyde and

Provided are 5-alkoxy-2-alkyl-7,8-cyclopentano[ h]-1,2,3,4-tetrahydroisoquinoline-1'-ones of the formula ##SPC1## Wherein R and R.sub.1 are the same or different lower alkyl groups, acid addition salts and quaternary ammonium salts thereof, and pharmaceutical compositions containing one or more of the compounds useful as hypotensive agents, and processes of producing the compounds. Also provided are novel 5-alkoxy-2-alkyl-1,2,3,4-tetrahydroisoquinoline intermediates of the formula ##SPC2## Wherein A is CHO-, HOOC-CH=CH-, or HOOC-CH.sub.2 -CH.sub.2 -, R and R.sub.1 are the same or different lower alkyl groups, and acid addition salts and quaternary ammonium salts thereof.

7,8-Cyclopentano[H]-1,2,3,4-tetrahydroisoquinoline-1'-ones

Indane is reacted with an .alpha.,.alpha.-dichloromethyl lower alkyl ether, the reaction mixture is treated with water to produce a mixture of 4-formylindane and 5-formylindane, the aldehyde isomers are separated and the aldehydes are catalytically hydrogenated to produce 4-methylindane and 5-methylindane.

Preparation of 4 and 5-methylindanes

Provided are novel cyclopentano-1,2,3,4-tetrahydroisoquinolines of the formula ##SPC1## Wherein R and R.sub.1 are the same or different lower alkyl groups, R.sub.2 is hydrogen or a lower alkyl group, m is an integer from 1 to 2, n is an integer from 1 to 2 and m + n equals 3, and acid addition salts thereof, processes for making the compounds and pharmaceutical compositions containing one or more of the compounds useful as hypotensive agents. Also provided are intermediates of the formula ##SPC2## Wherein R and R.sub.1 are the same or different lower alkyl groups and R.sub.3 is hydrogen, CHO--, ##EQU1## wherein R.sub.2 is hydrogen or a lower alkyl group.

Cyclopentano (h) or (f) 1,2,3,4-tetrahydroisoquinolines

N-substituted cyclopentano[h]-1,2,3,4-tetrahydroisoquinolines of the formula ##SPC1## Wherein R and R.sub.1 represent hydroxy, lower alkoxy, lower akanoyloxy or aryl-lower alkanoyloxy groups, R.sub.3 represents hydrogen or a lower alkyl group and R.sub.4 represents a lower alkyl, arylcarbonyl, aryl-lower alkyl, benzhydryl-lower alkyl, lower alkanoyl, aryl-lower alkanoyl, benzhydryl-lower akanoyl or benzhydrylcarbonyl group, and acid addition salts and quaternary ammonium salts thereof, and pharmaceutical compositions containing the compounds useful for lowering blood pressure in animals.

N-substituted-5,6-dihydroxycyclopentano[h]-1,2,3,4-tetrahydroisoquinolin

N-substituted cyclopentano[f]-1,2,3,4-tetrahydroisoquinolines of the formula ##SPC1## Wherein R.sub.1 and R.sub.2 represent hydroxy, lower alkoxy, lower alkanoyloxy or aryl-lower alkanoyl groups, R.sub.3 represents hydrogen or a lower alkyl group and R.sub.4 represents a lower alkyl, arylcarbonyl, aryl-lower alkyl, benzhydryl-lower alkyl, lower alkanoyl, aryl-lower alkanoyl, benzhydryl-lower alkanoyl or benzhydrylcarbonyl group, and acid addition salts and quaternary ammonium salts thereof, and pharmaceutical compositions containing one or more of the compounds useful for lowering blood pressure in animals.

N-substituted-7,8-dihydroxycyclopentano[f]-1,2,3,4-te

2-Alkyl-7,8-cyclopentano[h]-1,2,3,4-tetrahydroisoquinolines of the formula ##SPC1## Wherein R is an aryl-lower alkyl amino group, an aryl-lower alkyl imino group, a diaryl-lower alkyl amino group or a diaryl-lower alkyl imino group, R.sub.1 is hydrogen or a lower alkyl group and R.sub.2 is a lower alkyl group, and acid addition salts and quaternary ammonium salts thereof, and the use of such compounds in pharmaceutical compositions to lower blood pressure in hypertensive animals.

1-Substituted

5 OR 1'-Hydroxy-2-alkyl-7,8-cyclopentano[h]-1,2,3,4-tetrahydroisoquinolines and esters of the formulas ##SPC1## Wherein R is a lower alkyl having 1 to 6 carbon atoms, R.sub.1 is hydrogen, a lower alkyl group, an alkanoyl, benzoyl or aralkanoyl group, R.sub.2 is a lower alkyl group and R.sub.3 is hydrogen, benzoyl, an alkanoyl group or an aralkanoyl group, and acid addition salts and quaternary ammonium salts thereof. The compounds are useful in pharmaceutical compositions for lowering blood pressure in animals. Wherein R is a lower alkyl having 1 to 6 carbon atoms, R.sub.1 is hydrogen, a lower alkyl group, an alkaoyl, benzoyl or aralkanoyl group, R.sub.2 is a lower alkyl group and R.sub.3 is hydrogen, benzoyl, an alkanoyl group or an aralkanoyl group, and acid addition salts and quaternary ammonium salts thereof. The compounds are useful in pharmaceutical compositions for lowering blood pressure in animals.

Growing community of inventors

Memphis, TN, United States of America

William Ebenezer Solomons