Abbott Laboratories Corporation

Harold Elmer Zaugg

Cheuk M Lee

Nicholas Plotnikoff

David L Arendsen

Bruce W Horrom

Raymond John Michaels

Frederick Nelson Minard

The present invention provides 2,8-disubstituted-10-hydroxy-5,5-dimethyl-tetrahydro-and hexahydro-5H-[1]-benzopyrano[4,3-c]pyridines represented by Formulae I-III: ##STR1## wherein: R is selected from the group consisting of C.sub.4 -C.sub.20 straight or branched chain alkyl, C.sub.8 14 C.sub.20 straight or branched chain arylalkyl; n is an integer from 1-4 inclusive; and X is OH, NR.sub.1 R.sub.2, R.sub.1 and R.sub.2 being the same or different members of the group consisting of hydrogen and loweralkyl, and ##STR2## wherein Y is CH.sub.2, S, O or NR.sub.1 ; and the pharmaceutically acceptable salts thereof. The compounds are useful as antihypertensive agents.

2,8-Disubstituted-10-hydroxy-5,5-dimethyl-tetrahydro-and

A compound of the formula ##STR1## wherein R.sub.1 is H or loweralkyl; R.sub.2 is H, loweralkyl, phenyl or substituted phenyl; R is C.sub.3 -C.sub.20 alkyl, phenyl alkyl or substituted phenyl alkyl; R.sub.3 is H or ##STR2## where X is a straight or branched chain alkylene group of 3 to 4 carbon atoms, and R.sub.4 and R.sub.5 are the same or different members of the group consisting of H or loweralkyl; or R.sub.4 and R.sub.5 taken together form a 6- or 6- member heterocyclic ring and containing no more than one additional heterocyclic atom, with or without .alpha.-loweralkyl substituents, and the acid addition salts thereof. The compounds of this invention are useful as analgesics, tranquilizers, sedative-hypnotics and anti-glaucoma agents.

(8-Substituted-10-hydroxy-5,5-dimethyl-1,2

A compound of the formula ##STR1## wherein n is 1 or 2; R is C.sub.3 -C.sub.20 alkyl or arylalkyl; R.sub.1 is OH, loweralkoxy or NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 each are H, lower-alkyl or aryl. The compounds of this invention are useful as tranquilizers, analgesics, and sedative-hypnotics.

2,8-Disubtituted-10-hydroxy-5,5-dimethyl-1,2,3,4-tetrahydro-5H-[1]be

A compound of the formula ##STR1## wherein n is 1 or 2; R is C.sub.3 -C.sub.20 alkyl, phenyl alkyl or substituted phenyl alkyl; R.sub.1 is NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 each are H, loweralkyl or phenyl or substituted phenyl. The compounds of this invention are useful as tranquilizers, analgesics, and sedative-hypnotics.

2,8-Disubstituted-10-hydroxy-5,5-dimethyl-1,2,3,4-tetrahydro-5H

This invention provides compounds of the structure ##STR1## where R.sub.1 is C.sub.3 -C.sub.20 alkyl or arylalkyl; R.sub.2 is hydrogen, loweralkanoyl, loweralkylsulfonyl, loweralkoxycarbonyl, carbamoyl or ##STR2## wherein X is an alkylene group having from 2 to 4 carbon atoms; and R.sub.3 and R.sub.4 are the same or different members of the group consisting of hydrogen or loweralkyl, or R.sub.3 and R.sub.4 taken together form a 5-, 6-, or 7-member heterocyclic ring; and the pharmaceutically acceptable acid addition salts thereof. The compounds of this invention are useful as analgesics, tranquilizers and sedative-hypnotics.

10-Amino-5H-[1]benzopyrano[4,3-c]pyridines

A compound represented by the formula ##STR1## wherein R is H, loweralkyl, hydroxyloweralkyl or ##STR2## where R.sub.2 is an alkyl group of 1 to 15 carbon atoms; and R.sub.1 is H or ##STR3## where R.sub.2 is an alkyl group of 1 to 15 carbon atoms. These compounds are useful as antischizophrenics.

Dibenzo�b,e!�1,4!diazepines

A compound of the formula ##STR1## wherein R is a C.sub.6 -C.sub.20 alkyl, arylalkyl or cycloalkyl alkyl; R' is phenyl or substituted phenyl; and X is H, halogen,

2-(.alpha.-Amidobenzyl)-5-alkylresorcinols

A method of preventing and/or controlling convulsions in mammalian patients comprising administering to a patient in need of such treatment a therapeutically effective amount of 3-(3-methyl-2-octyl)-1-[4-(1-homopiperidine) butyryloxy]-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo [b,d]pyran hydrochloride.

3-(3-Methyl-2-octyl)-1-[4-(1-ho

A compound of the formula ##STR1## wherein n = 2 or 3; R.sub.1 is a C.sub.3 -C.sub.20 alkyl or arylalkyl; R.sub.2 is loweralkyl or phenyl; and R.sub.3 is H or replaces the hydrogens in (CH.sub.2).sub.n with CH.sub.3 ; and m is 1, 2 or 4. These compounds exhibit central nervous system activity and are useful as antidepressants.

6A-Azacannabinoids

Covers 2-substituted-5-alkyl resorcinols represented by the formula ##STR1## wherein R.sub.1 is hydrogen or lower-alkanoyl; R.sub.2 is a straight or branched chain alkyl of 1 to 20 carbon atoms; and X is nitrogen or C-methyl. The compounds of this invention are useful as tranquilizers, analgesics, sedative-hypnotics and anticonvulsants.

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Lake Forest, IL, United States of America

Harold Elmer Zaugg