Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1990-08-16
1993-03-09
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514419, 514529, 514557, 514613, 514616, 514859, 549341, 458303, 458340, 560125, 562498, 562507, 564152, 564191, 564457, 564461, A61K 3116, C07C21118
Patent
active
051927985
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention includes novel lipophilic polyamines which are useful for treating hypercholesterolemia and intermediates thereto. Background of the Invention
Cholesterol is probably the sole precursor of bile acids. During normal digestion, bile acids are secreted into the intestines. A major portion of the bile acid is absorbed from the intestinal tract and returned to the liver via the enterohepatic circulation system. Only very small amounts of bile acids are found in normal serum. Polymeric anion exchange resins are known to combine with the bile acids in the intestine to form an insoluble complex which is excreted in the feces. This results in partial removal of bile acids from the enterohepatic circulation by preventing their reabsorption. The increased fecal loss of bile acids leads to an increased oxidation of cholesterol to bile acids, a decrease in beta lipoprotein or low density lipoprotein plasma levels and a decrease in plasma cholesterol levels. Although excretion of bile acids produces an increase in hepatic synthesis of cholesterol, plasma cholesterol falls. These anion exchange resins are not systemically absorbed or digested although large quantities, up to 54 grams of the formulated resin per day for cholestyramine resin powder, are needed. These resins are not water soluble but are typically administered as an aqueous suspension.
Colestipol-niacin therapy has recently been shown to significantly increase the regression of atherosclerosis in drug-treated subjects. D. H. Blankenhorn et al., JAMA, 1987, 257:3233-3240. Others have found cholestyramine reduces the incidence of coronary heart disease in treated patients. Lipid Research Clinics Program, JAMA. 1984 251:351-364. With the positive effects of resins on coronary heart disease, one must balance the sometimes poor patient compliance. Therefore the medical community has recognized the need for new effective drugs of this type. S. M. Grundy, "Drugs Affecting Lipid Metabolism"; R. Paoletti Ed., Springer Verlag: Berlin 1987, pp. 34-41. Information Disclosure
Some of the amino substituted hydrocarbons used to practice this invention are claimed in International Patent Application PCT/US86/02116 which has an International Publication Date of Apr. 23, 1987. The International Application teaches these compounds are useful to treat phospholipid mediated conditions and diabetes.
The following are references to polyamine compounds similar to the compounds described herein, but not for the use of our invention.
CA 88:106267Z (German Patent, DE 2624528) discloses 1,2-Ethanedicimine, N-[2-(dimethylamino)ethyl]-N',N'-bis[2-[[2-(dimethylamino)ethyl]methylamin o]ethyl]-N-methyl-, useful as polyurethane foam materials.
CA 105:197229X (Japanese Patent, J61146265) discloses Ethanaminium, N,N-bis(2-amino-ethyl)-N-(carboxymethyl)-2-(dodecylamino)chloride, useful as an antimicrobial agent.
CA 74:99664g (German Patent, DE 2039214 and U.S. Pat. No. 3,734,953) disclose Isophthalamic acid, N,N',N"-(nitrilotriethylene)tris[5-nitro-, trimethyl ester, useful as a radiopaque agent.
CA87:22564k (U.S. Pat. No. 4.003.934) discloses 1,2-Ethanediamine, N,N-bis(2-aminoethyl)-N'[2-(3,3-dimethylbicyclo[2.2.1]hept-2-yl)-1 [2-(3,3-dimethylbicyclo[2.2.1]hept-2-yl)ethyl]propyl]tetrahydrochloride, useful as an antimicrobial agent.
CA67:21731n (U.S. Pat. No. 3,291,808) discloses N-(dialkylaminoalkyl)-1,4-naphthalenediamines having useful antiparasitic properties.
CA107:40601f (U.S. Pat. No. 4.631 337) discloses hydrolyticallystable dense star polyamines, which are useful as calibration standards, high efficiency proton scavengers and in making size selective membranes.
CA54:26191g (U.S. Pat. No. 2.874.174) discloses alkyl amides of N,N,N-tris(aminoalkyl)amines which are useful as binding agents for asphalt pavements.
SUMMARY OF THE INVENTION
A compound of the formula I .dbd.0,C(0)OR.sub.11, --C(0)NH.sub.2, --CH.dbd.CH.sub.2, or ethylene ketal; --C(0)OR.sub.11, C(0)NH.sub.2, --CH.dbd.CH.sub.2, or ethylene ketal; --C(0)OR.sub.11,C(0)NH.sub.2, --CH.dbd.C
REFERENCES:
patent: 2874174 (1959-02-01), Huber
patent: 3291808 (1966-12-01), Elslager
patent: 3734953 (1973-05-01), Bernstein
patent: 4003934 (1977-01-01), Grier
patent: 4631337 (1986-12-01), Tomalia
Aiken James W.
Spilman Charles H.
Thomas Edward W.
Gammill Martha A.
Raymond Richard L.
The Upjohn Company
Wootton Thomas A.
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