Hoffmann-la Roche Inc.

Kenneth E Fahrenholtz

Richard W Kierstead

Robert W Guthrie

Jefferson Wright Tilley

John E Heveran

An improved immunoassay for detecting cannabinoids is described. This immunoassay is characterized by utilizing, as reagents, antibody, .sup.125 I-radiolabeled antigen, an unlabeled antigen and an anion exchange resin for separation of labeled and unlabeled antigen. The iodinated tetrahydrocannabinol moiety is stabilized by the addition of small quantities of antioxidants such as butylated hydroxy toluene.

Radioimmunoassay for cannabinoids

There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof. There are also disclosed processes and intermediates utilized to produce the end products. The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.

1,4-Disubstituted piperazine compounds

There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n-- wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n-- wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof. There are also disclosed processes and intermediates utilized to produce the end products. The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.

Adrenergic blocking agents

There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n -wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n -- wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof. There are also disclosed processes and intermediates utilized to produce the end products. The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.

Intermediates for preparing adrenergic blocking agents

There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n -- wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n -- wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof. There are also disclosed processes and intermediates utilized to produce the end products. The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.

Sulfonamide intermediates for adrenergic blocking agents

There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n -- wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n -- wherein n is 2 to 20, ##EQU1## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof. There are also disclosed processes and intermediates utilized to produce the end products. The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.

There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n -- wherein n is 2 to 20, ##STR2## and ##STR3## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR4## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n -- wherein n is 2 to 20, ##STR5## and ##STR6## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof. There are also disclosed processes and intermediates utilized to produce the end products. The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.

There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR2## R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof. There are also disclosed processes and intermediate utilized to produce the end products. The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.

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Bloomfield, NJ, United States of America

Kenneth E Fahrenholtz