Other

Rohm and Haas Company

Warren-teed Laboratories, Inc.

Michael C Seidel

Wayne O Johnson

Harlow L Warner

Stanley A Greenfield

Evan H Crook

W David Weir

Martha H Wolfersberger

William C Von Meyer

James L Rainey

Treatment of carcinoma in a human is disclosed, including administering a therapeutically effective amount of a fatty acid having four carbons with two conjugated double bonds formed by reacting an ester of a fatty acid with a tosyl chloride or a mesyl chloride, the fatty acid having four carbon atoms such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogens, and a double bond is positioned between carbon three and four. The tosylate or mesylate of the ester of the fatty acid having the chain of four carbon atoms such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogens, and a double bond is positioned between carbon three and four is reacted with diazabicyclo-undecene. The method includes administering to a human a highly purified fatty acid in accordance with the present invention.

Suppression of carcinoma using high purity conjugated fatty acid

A method for providing a purified conjugated fatty acid is disclosed. The purified conjugated fatty acid is formed by separating by liquid chromatography a conjugated fatty acid formed by a novel synthesis of reacting an ester of a fatty acid having a four carbon chain such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogen atoms, and a double bond is positioned between carbon three and carbon four, with a tosyl chloride or a mesyl chloride to form a tosylate or mesylate of said ester, and reacting the tosylate or mesylate of said ester with diazabicyclo-undecene. Reacting an ester of a fatty acid having a four carbon chain such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogen atoms, a double bond is positioned between carbon three and carbon four, with a tosyl chloride or a mesyl chloride to form a tosylate or mesylate of said ester, and reacting the tosylate or mesylate of said ester with diazabicyclo-undecene forms a conjugated fatty acid having a purity greater than 50%, and separating by liquid chromatography forms a conjugated fatty acid having a purity greater than 90%. In one aspect, the liquid chromatography uses a strong acid macroreticular ion exchange resin. In one aspect, the liquid chromatography includes silver ion liquid chromatography.

Liquid chromatography of high purity conjugated fatty acid

A synthesis process is disclosed for producing a conjugated fatty acid at specified temperature in high yield, including providing an ester of a fatty acid having somewhere in its carbon chain a chain of four carbon atoms such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogen atoms, and a double bond is positioned between carbon three and carbon four and reacting with a chloride selected from the group consisting of toluenesulfonyl chloride, methanesulfonyl chloride, benzenesulfonyl chloride, alkylsulfonyl chloride, and arylsulfonyl chloride at a temperature in the range of 10&deg; C.-100&deg; C., preferably 20&deg; C.-50&deg; C. The synthesis process provides a conjugated fatty acid formed from the ester reacted with diazabicycloundecene. In one aspect, the ester is formed in a pyridine solvent. In one aspect, a mesylate is formed with mesyl chloride in acetonitrile and triethyl amine. In one aspect, the reaction with diazabicyclo-undecene is conducted in a polar, non-hydroxylic solvent of acetonitrile to form a preferred isomer at the specified temperature in high yield.

Synthesis of conjugated fatty acid

A method for the treatment of carcinoma in a human is disclosed, including administering to a human a therapeutically effective amount of 9-cis, 11-trans octadecadienoic acid formed by reacting an ester of ricinoleic acid with a tosyl chloride or a mesyl chloride to form a tosylate or mesylate of an ester of ricinoleic acid, and reacting the tosylate or mesylate of an ester of ricinoleic acid with diazabicyclo-undecene. The method includes administering to a human a purified conjugated linoleic acid (CLA) produced by a novel synthesis process for producing 9-cis, 11-trans octadecadienoic acid at room temperature in high yield including providing a tosylate or mesylate of a methyl ester of ricinoleic acid and providing a purified 9-cis, 11-trans octadecadienoic acid formed when the tosylate or mesylate reacts with diazabicyclo-undecene.

Suppression of carcinoma using high purity conjugated linoleic acid (CLA)

A synthesis process for producing 11-cis, 13-trans eicosadienoic acid at room temperature in high yield is disclosed, including providing a tosylate or mesylate of a methyl lesquerolate and 11-cis, 13-trans eicosadienoic acid formed when the tosylate or mesylate reacts with diazabicyclo-undecene. In one aspect, the tosylate of the methyl lesquerolate is formed with tosyl chloride in a pyridine solvent. In one aspect, the mesylate of the methyl lesquerolate is formed with mesyl chloride in acetonitrile and triethyl amine. In one aspect, the tosylate or mesylate is reacted with diazabicyclo-undecene in a polar, non-hydroxylic solvent of acetonitrile to form the preferred isomer of 11-cis, 13-trans eicosadienoic acid at room temperature in high yield.

Synthesis of conjugated eicosadienoic acid

A method for providing a purified conjugated linoleic acid (CLA) is disclosed. The purified conjugated linoleic acid (CLA) is formed by separating by liquid chromatography a 9-cis, 11-trans octadecadienoic acid formed by a novel synthesis of reacting an ester of ricinoleic acid with a tosyl chloride or a mesyl chloride to form a tosylate or mesylate of an ester of ricinoleic acid, and reacting the tosylate or mesylate of an ester of ricinoleic acid with diazabicyclo-undecene. Reacting an ester of ricinoleic acid with a tosyl chloride or a mesyl chloride to form a tosylate or mesylate of an ester of ricinoleic acid, and reacting the tosylate or mesylate of an ester of ricinoleic acid with diazabicyclo-undecene forms a 9-cis, 11-trans octadecadienoic acid having a purity greater than 50%, and separating by liquid chromatography forms a 9-cis, 11-trans octadecadienoic acid having a purity greater than 90%. In one aspect, the liquid chromatography uses a strong acid macroreticular ion exchange resin. In one aspect, the liquid chromatography includes silver ion liquid chromatography.

Silver ion chromatography of high purity conjugated linoleic acid (CLA)

A synthesis process for producing 9-cis, 11-trans octadecadienoic acid at room temperature in high yield is disclosed, including providing a tosylate or mesylate of a methyl ester of ricinoleic acid and 9-cis, 11-trans octadecadienoic acid formed when the tosylate or mesylate reacts with diazabicyclo-undecene. In one aspect, the tosylate of the methyl ester of ricinoleic acid is formed with tosyl chloride in a pyridine solvent. In one aspect, the mesylate of the methyl ester of ricinoleic acid is formed with mesyl chloride in acetonitrile and triethyl amine. In one aspect, the tosylate or mesylate is reacted with diazabicyclo-undecene in a polar, non-hydoxylic solvent of acetonitrile to form the preferred isomer of 9-cis, 11-trans octadecadienoic acid at room temperature in high yield.

Synthesis of conjugated linoleic acid (CLA)

Substituted 1,2,4-4H-triazoles of the formula ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen atoms and R.sup.3 is alkyl, alkenyl, alkynyl, cycloalkyl benzyl or phenyl. These compounds are fungicides and are particularly useful for the control of cereal rust.

4-alkyl-1,2,4-4H-triazole derivatives

Phosphoramidates and salts and salt complexes useful as anthelmintics are disclosed. The products are prepared by treating an aminobenzene with an appropriately substituted isothiocyanatoate.

Method and composition for treating helminths containing

Macroreticular resins have shown biological activity for gallstone removal and lowering serum cholesterol by selective adsorption of cholesterol from the bile.

Dissolution of gallstones

Substituted 1,2,4-4H-triazoles of the formula ##STR1## wherein A is a variety of groups including alkyl, --C(O)R.sup.4, --CH(OH)CCl.sub.3 and substituted benzyl and phenyl and R.sup.8 is alkyl. These compounds are fungicides and are particularly useful for the control of cereal rusts.

1,2,4-4H-triazole derivatives

Novel compounds belonging to the class of 3-carboxy (or the physiologically acceptable salts thereof), 3-carbalkoxy, and 3-carbamoyl-1-alkyl-4,6-disubstituted pyrid-2-ones. These compounds possess biological activity and in particular are gametocides and plant growth regulators. Novel 3-cyano-1-alkyl-4,6-disubstituted pyrid-2-ones are also disclosed as intermediates.

1-Alkylpyrid-2-ones

1-Alkylpyrid-2-one

This invention relates to novel isothiazolopyridinones of the formula: ##SPC1## Wherein Y is hydrogen, (C.sub.1 --C.sub.12)alkyl, aralkyl of up to 11 carbon atoms, (C.sub.1 -C.sub.4)alkylcarbonyl, (C.sub.6 -C.sub.10)arylcarbonyl, aralkyl-carbonyl of up to 11 carbon atoms, (C.sub.2 -C.sub.3)hydroxyalkyl, a group of the formula: ##EQU1## wherein R.sup.4 is hydrogen, (C.sub.1 -C.sub.4)alkyl or phenyl and R.sup.5 and R.sup.6 are individually (C.sub.1 -C.sub.4)alkyl or taken together with the nitrogen atom to which they are attached, form a 5 or 6 membered azacyclic ring, which can include as additional hetero atoms, O, S or N or any combination of these wherein the total number of hetero atoms does not exceed 3; or a carbamoyl group of the formula: ##EQU2## wherein R.sup.7 is (C.sub.1 -C.sub.18)alkyl, (C.sub.6 -C.sub.10)aryl or aralkyl of up to 11 carbon atoms; R.sup.1 and R.sup.3 are individually hydrogen, (C.sub.1 -C.sub.4)alkyl, phenyl or benzyl; and R.sup.2 is hydrogen or (C.sub.1 -C.sub.4)alkyl; provided that at least one of R.sup.1, R.sup.2 and R.sup.3 is other than hydrogen; to agricultural compositions containing them, to processes for preparing them and to their utilization in controlling phytopathogenic fungi.

Growing community of inventors

Chalfont, PA, United States of America

Michael C Seidel