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A series of amine carboxyboranes including their amides and esters were synthesized and shown to have potent hypolipidemic activity in rodents at 20 mg/kg/day. Ethylamine carboxyborane, di-n-propylamine-carboxyborane, trimethylamine-carbomethoxyborane, n-butylamine carbomethoxyborane, methylamine-N-ethyl carbamoylborane and trimethylamine-N-n-octyl carbamoylborane were the most potent derivatives demonstrating hypocholesterolemic and hypotriglycemic activities in rats orally at 20 mg/kg/day. These derivatives lowered tissue lipids, e.g. cholesterol, in the rat liver, small intestine and aorta. The fecal lipids were elevated. Furthermore, the agents lowered cholesterol and triglycerides in the serum VLDL and LDL fractions but caused elevations in the HDL fraction after 14 days. The agents inhibited hepatic enzymatic activities of rate limiting steps involved in lipid metabolism, e.g. ATP dependent citrate lyase, sn-glycerol-3-phosphate acyltransferase and phosphatidylate phosphohydrolase.

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The cyanoborane adduct of diethyl ((dimethylamino)methyl)phosphonate, (Et0)2P(0)CH2NMe2-BH2CN (1), was N-alkylated with Et3OBF4 to give the nitrilium salt (Et0)2P(0)CH2NMe2-BH2CNEtBF4 (2). Hydrolysis of 2 with water gave the corresponding carboxyborane (Et0)2P(0)CH2NMe2-BH2C02H (3), and with alkali gave the carbamoyl derivative (Et0)2P(0)-CH2NMe2-BH2CONHEt (4). Reaction of the carbamoyl compound 4 with Et3OBF4 followed by base treatment resulted in the formation of an imino ether, (Et0)2P(0)CH2NMe2-BH2C(0Et)=NR ( 5), which on hydrolysis yielded the ester (Et0)2P(0)-CH2NMe2-BH2C02Et (6). Compound 6 could be obtained in higher yields by an exchange reaction between the (aminomethyl)phosphonate and 0(CH2CH2)2NCH3-BH2C02Et. The borane adduct (Et0)2P(0)CH2NMe2'BH3 (7) was formed directly by reaction of the (aminomethyl)phosphonate and BHyTHF. These compounds were characterized by spectroscopic methods and elemental analysis.