Uniroyal Inc.

Uniroyal Chemical Company, Inc.

Uniroyal Chemical Ltd/uniroyal Chemical Ltee

Uniroyal Chemical Ltd./ltee

Arthur D Brewer

Robert W Neidermyer

William S McIntire

Robert A Davis

John A Minatelli

Mark A Dekeyser

Allyn R Bell

Arthur M P Doweyko

Stephen E Cantor

Howard L Plant

William A Harrison

Gaik-Lean Chee

John A Lacadie

James B Pierce

Andrew A Znotins

Alexsei Yurievich Aksinenko

Duncan D Lennox

Allan K Tsai

John W Harris

Vladimir Borisovich Sokolov

Substituted oxadiazines useful as pesticides

Certain pyridine and quinoline derivatives' which inhibit replication of the retroviruses HIV-1, HIV-2 and human cytomegalovirus (HCMV) are provided. Pharmaceutical compositions useful in methods of treating or inhibiting certain retrovirus infections are described.

Antiretroviral compounds and compositions

N-(2-Fluorophenyl)-1,2,3,4-tetrahydro-6-hydroxy-2,4-dioxo-5-pyrimidinecarbo xamide, useful for regressing or inhibiting the growth of leukemia and tumors in mammals. The compound has the formula: ##STR1## wherein R.sub.1 and R.sub.2 are selected from hydrogen or a cyclic or acyclic group which forms pyrimidine nucleosides or pseudo nucleosides, and the pharmacologically acceptable acid addition salts thereof.

Barbituric acid derivative and treatment of leukemia and tumors therewith

Method for reducing uric acid levels in mammals, comprising administering compounds having the formula: ##STR1## wherein A is selected from the group consisting of ##STR2## and --CH.sub.2 --; X is oxygen or sulfur; R.sub.6 is hydrogen, an alkoxy group having from one to four carbon atoms, or alkylthio, amino, dialkylamino, or NHR.sub.7 wherein R.sub.7 is alkyl, aryl or arylamino, the alkyl moieties of which have from 1 to 12 carbon atoms;

Method for reducing serum uric acid levels

A process is provided for the purification to highly purified states of 5-pyrimidinecarboxamides which are essentially insoluble in both organic and inorganic solvents. The 5-pyrimidinecarboxamide to be purified is contacted with an organic base having a pKa value in excess of 6.95 to form an adduct. The adduct is purified through recrystallization and the desired 5-pyrimidinecarboxamide is regenerated from the adduct in highly purified form with acid. Additionally, an adduct resulting from the combination of a 5-pyrimidinecarboxamide with such an organic base is provided, which adduct is capable of being purified using recrystallization techniques, where the 5-pyrimidinecarboxamide is not itself capable of being so purified due to its relative insolubility in organic and inorganic solvents.

Purification of 5-pyrimidinecarboxamides

Novel 5-pyrimidinecarboxamides useful for regressing or inhibiting the growth of leukemia and tumors. The compounds have the formula: ##STR1## wherein R.sub.1 is hydrogen or an alkoxy group having from one to four carbon atoms;

5-pyrimidinecarboxyamides and treatment of leukemia therewith

Novel 5-pyrimidinecarboxamides useful for regressing or inhibiting the growth of leukemia and tumors in mammals. The compounds have the formula: ##STR1## wherein: R is hydrogen, 2- or 3-halo, 4-fluoro, 2-methyl, 2- or 4-alkoxy, or 2- or 4-trifluoromethyl, and R.sub.1 is hydrogen; or

5-Pyrimidinecarboxamides and treatment of leukemia and tumors therewith

Disclosed is a method for synthesizing dihydro-1,4-dithiins by the reaction of an acyloin or a halocarbonyl compound with an organic thiosulfate.

Method of synthesizing dihydro-1,4-dithiins

A method of making certain 2,3-dihydro-1,4-dithiins of the following formula by the action of alpha-hydroxyketones (acyloins) of 1,2-dithiols: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen or alkyl having 1 to 6 carbon atoms or are joined together to form a ring with 3 or 4 methylene groups, and R.sup.3 and R.sup.4 are hydrogen or the same or different alkyl groups having 1 to 10 carbon atoms, which alkyl groups may be substituted with lower alkoxy groups.

Method of making certain 2,3-dihydro-1,4-dithiins

Regulation of the growth of plant life, including herbicidal, defoliant or desiccant effects, may be accomplished with certain 2,3-dihydro-1,4-dithiin 1,1,4,4-tetroxides of the formula ##STR1## wherein the R's have various values such as hydrogen, alkyl, etc. Certain of the compounds, such as 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide, are new chemicals, and are useful as pre- and post-emergent herbicides, and in harvest aid procedures, such as defoliation/desiccation of various crops, including cotton and potatoes.

Substituted dithiin tetroxide plant growth regulants

This method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide is based on the use of an oxathiolane, namely, 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide, which may be formed by condensing 2-mercaptoethanol with acetoacetanilide under acidic conditions in a solvent medium (aromatic hydrocarbon, chlorinated hydrocarbon or alkyl ester of an aliphatic acid). The said oxathiolane, with or without purification, is reacted with hydrogen peroxide in water or in a water-organic solvent mixture under basic conditions in the presence of a catalytic amount of a metal compound such as sodium tungstate to form 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide 3-oxide. The said oxathiolane oxide, while dissolved in a chlorinated hydrocarbon or an alkyl ester of an aliphatic carboxylic acid, or while suspended in an aromatic hydrocarbon, is subjected to a ring expansion reaction by heating under acidic conditions in the presence of a catalytic quantity of a quaternary ammonium salt to form 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide with evolution of water. The product is a known bactericide and fungicide.

Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide

Fungi, bacteria and viruses are controlled, especially on plants, by application of chemicals of the formula: ##STR1## such as 2,3-dihydro-5-phenyl-1,4-dithiin 1,1,4,4-tetroxide, 2-ethyl-5,6-dihydro-3-methyl-1,4-dithiin 1,1,4,4-tetroxide and 2,3-dihydro-5-methyl-2-phenyl-1,4-dithiin 1,1,4,4-tetroxide.

2,3-Dihydro-1,4-dithiin 1,1,4,4-tetroxide antimicrobials

Regulation of the growth of plant life, including herbicidal, defoliant or desiccant effects, may be accomplished with certain 2,3-dihydro-1,4-dithiin 1,1,4,4-tetroxides of the formula ##STR1## wherein the R's have various values such as hydrogen, alkyl, etc. Certain of the compounds, such as 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide, are new chemicals, and are useful as pre-and post-emergent herbicides, and in harvest aid procedures, such as defoliation/desiccation of various crops, including cotton and potatoes.

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Puslinch, Canada

Arthur D Brewer