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Details for Patent: 3,867,394

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Details for Patent: 3,867,394

Title: Imidazolinyl phenyl carbonyl compounds, acid addition salts and related compounds
Abstract:This invention is concerned with tetrahydropyrimidinyl phenyl carbonyl acid addition salts, imidazolinyl phenyl carbonyl acid addition salts, dihydroimidazoisoindolols, tetrahydropyrimidoisoindolols, and tetrahydropyrimidoisoindolol acid addition salts which are all pharmacologically efficacious as anti-depressants. The tetrahydropyrimidinyl phenyl carbonyl acid addition salts, the tetrahydropyrimidoisoindolols and the tetrahydropyrimidoisoindolol acid addition salts are also efficacious as diuretics while the imidazolinyl phenyl carbonyl acid addition salts and the dihydroimidazoisoindolols are efficacious as anorexiants. This invention is also concerned with several processes for the preparation of these compounds.
Inventor(s): Sulkowski; Theodore S. (Wayne, PA)
Assignee: American Home Products Corporation (New York, NY)
Filing Date:Sep 06, 1973
Application Number:05/394,706
Claims:1. A process for the production of a compound having the formula: ##SPC7##

wherein R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, phenyl, phen(lower)alkyl, monohalophenyl, dihalophenyl, mono(lower)alkylphenyl), di(lower) alkylphenyl, trifluoromethylphenyl, mono(lower)alkoxyphenyl, di(lower)alkoxyphenyl, thienyl, pyridyl, furyl and tetrahydro-2-naphthyl; R.sub.2 is selected from the group consisting of hydrogen, halogen, amino, lower alkylamino, lower alkyl and lower alkoxy; and R.sub.3 is hydrogen when R.sub.2 and R.sub.3 are dissimilar and when R.sub.2 and R.sub.3 are the same they are both selected from the group consisting of hydrogen, halogen, lower alkyl and lower alkoxy, which comprises contacting a compound of the formula: ##SPC8##

wherein R.sub.1, R.sub.2 and R.sub.3 are defined as above, with a mineral acid, to form the mineral acid addition salt of a phthalimidine of the formula: ##SPC9##

wherein R.sub.1, R.sub.2 and R.sub.3 are defined as above, reacting said phthalimidine acid addition salt with a sulfonyl halide selected from the group consisting of those having the formula:

R.sub.4 SO.sub.2 X

wherein R.sub.4 is selected from the group consisting of lower alkyl, phenyl, monohalophenyl, dihalophenyl, mono(lower) alkylphenyl, di(lower)alkylphenyl, trifluoromethylphenyl, mono(lower)alkoxyphenyl and di(lower)alkoxyphenyl and X is halogen, in pyridine at a temperature that is in the range from about 80.degree.C. to about 115.degree.C. for a period from about 2 hours to about 10 hours, to form a compound of the formula: ##SPC10##

wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are defined as above, and hydrolyzing said sulfonylimidazoisoindolone by treatment with from about 80 to about 100 percent sulfuric acid, to form a sulfate of the formula: ##SPC11##

wherein R.sub.1, R.sub.2 and R.sub.3 are defined as above, and then

2. A process as described in claim 1 wherein the mineral acid is hydrochloric acid; the sulfonylation reaction is conducted with a sulfonyl chloride in pyridine at the reflux temperature of the reaction mixture for about two hours; the hydrolysis and rearrangement is conducted with 90 percent sulfuric acid; and the base is sodium bicarbonate.
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