Sharps Associates

Sisa Incorporated

Sisa Pharmaceutical Laboratories, Inc.

The John C. Sheehan Institute for Research, Inc.

Sheehan Institute for Research, Inc.

Haldean Cloyce Dalzell

Raj Kumar Razdan

Martin Winn

Joyce Ruth Krei

Harry George Pars

James E Quick

Patricia Herlihy

Barbara Z Terris

The present invention involves 7-carboethoxymorphinan-6-one compounds of the formula: ##STR1## These compounds are useful as analgesic and/or narcotic antagonists.

7-Carboethoxy-morphinan-6-one compounds

Disclosed are 4,5.alpha.-epoxy-3-hydroxy or methoxy-7-(1-hydroxyalkyl or 1-oxoalkyl)morphinan-6-one compounds characterized by the structural formulae: ##STR1## In the foregoing formulae R is methyl, cyclopropylmethyl, cyclobutylmethyl, propargyl, allyl, dimethylallyl, cis-chloroallyl or furfuryl; R.sub.1 is H or methyl; R.sub.2 is straight or branched chain alkyl of from 1 to 10 carbon atoms, aryl, substituted aryl or arylalkyl, in which the alkyl group contains from 1 to 6 carbon atoms, and R.sub.3 is a straight chain alkyl of 1 to 4 carbon atoms.

4,5.alpha.-Epoxy-3-hydroxy or methoxy-7-(1-hydroxy-alkyl or

Tetrahydrodibenzopyrans having the structure ##STR1## in which R.sub.1 is hydrogen or acetyl and R.sub.2 is alkyl having from 1 to 4 carbon atoms are effective anti-glaucoma agents, free from all but a very small amount of CNS activity, when applied topically.

Anti-glaucoma composition and method

Tetrahydrodibenzopyrans having the structure ##STR1## in which R, R.sub.1, and R.sub.2 are alkyl having from 1 to 4 carbon atoms and ophthalmologically acceptable acid addition salts thereof are effective anti-glaucoma agents, free from all but a very small amount of CNS activity, when applied topically.

Composition and method for treating glaucoma

(-)-6A,10A-Trans-1-hydroxy-3-n-pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro dibenzo[b,d]pyran and related pyrans are prepared by a one-step process from (+)-p-mentha-2,8-dien-1-ol and substituted resorcinols. The pyrans produced by the process of this invention have useful pharmacological properties.

Process for the preparation of

Benzopyrans of the formula ##STR1## wherein n represents 0 or 1, R is an alkyl group having 1 to 20 carbon atoms, an aryl-lower alkyl group or a cycloalkyl-lower alkyl group, R.sub.1 is hydrogen or ##STR2## wherein R.sub.4 is lower alkyl, phenyl, cycloalkyl-lower alkyl or aryl-lower alkyl, R.sub.2 is a lower alkyl and R.sub.3 is hydrogen or one or two lower alkyl groups, pharmaceutical compositions containing the compounds, and uses of the compounds as tranquilizers and analgesics.

Oxo C-ring benzopyrans

3-Formyl-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol, ethers and esters thereof having the formula ##STR1## wherein R is hydrogen, lower alkyl or lower alkanoyl and R.sub.6 is formyl or 1,3-dithiolan-2-yl but is 1,3-dithiolan-2-yl only when R is hydrogen, and derivatives thereof of the formula ##STR2## wherein R.sub.1 is hydrogen or lower alkanoyl, R.sub.2 is alkyl, aryl-lower alkyl or cycloalkyl-lower alkyl, A represents ##STR3## when R.sub.1 is hydrogen and R.sub.3 is lower alkyl, and A is ##STR4## when R.sub.1 is lower alkanoyl and R.sub.4 is the same lower alkanoyl represented by R.sub.1, processes of making such compounds and intermediates useful in such processes, pharmaceutical compositions containing the compounds and the use of the compounds as tranquilizing and antidepressant agents.

Benzopyrans having an unsaturated side chain

(-)-6A,10A-TRANS -1-Hydroxy-3-n-pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrodibenzo[b,d]pyr an and related pyrans are prepared by a one-step process from (+)-p-mentha-2,8-dien-1-ol and substituted resorcinols. The pyrans produced by the process of this invention have useful pharmacological properties.

1,2,3,4-Tetrahydrocyclopenta[c][1]benzopyrans of the formulae ##STR1## wherein R is a lower alkyl group having 1 to 5 carbons, R.sub.1 is hydrogen or a lower alkyl group having 1 to 5 carbons, R.sub.2 is a lower alkyl group and R.sub.3 is an alkyl group having 1 to 20 carbon atoms, a phenyl-lower alkyl group or a cycloalkyl-lower alkyl group. The compounds have anti-hypertensive, antidepressant, analgesic, anticonvulsant, anti-anxiety, sedative-hypnotic and tranquilizing activity in animals.

Alkyl substituted-4-oxo-cyclopenta benzopyrans

1,2,3,4-Tetrahydrocyclopenta[c] [1]benzopyrans of the formulae ##SPC1## Wherein R is a lower alkyl group having 1 to 5 carbons, R.sub.1 is hydrogen or a lower alkyl group having 1 to 5 carbons, R.sub.2 is a lower alkyl group and R.sub.3 is an alkyl group having 1 to 20 carbon atoms, a phenyl-lower alkyl group or a cycloalkyl-lower alkyl group. The compounds have anti-hypertensive, antidepressant, analgesic, anticonvulsant, anti-anxiety and tranquilizing activity in animals.

Pharmaceutical compositions containing alryl substituted cyclopenta

1,2-Dihydro-4H-thieno-[2,3-c][1]benzopyrans of the formulae ##SPC1## Wherein R is a lower alkyl group having 1 to 5 carbons, R.sub.1 is hydrogen or a lower alkyl group having 1 to 5 carbons, R.sub.2 is a lower alkyl group and R.sub.3 is an alkyl group having 1 to 20 carbon atoms, a phenyl-lower alkyl group or a cycloalkyl-lower alkyl group. The compounds have analgesic, antihypertensive, antidepressant, anticonvulsant, antianxiety, sedative-hypnotic and/or tranquilization activity.

Growing community of inventors

Weston, MA, United States of America

Haldean Cloyce Dalzell