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Title: Method of enhancing learning and/or memory in warm blooded animals
Claims: I claim: 1. A method of enhancing learning or memory in a warm blooded animal which consists essentially of administering thereto a therapeutically effective amount to enhance the ability of the animal to learn tasks or to enhance the ability of the animal to memorize information of a substance selected from the group consisting of I. ethereally monosubstituted monosaccharides having the formula S.sub.1 --O--Y and therapeutically effective and pharmaceutically acceptable organic acid and inorganic acid salts thereof, and Ii. ethereal monosubstitutions of monosaccharide derivatives having the formula S.sub.2 --O--Y and therapeutically effective and pharmaceutically acceptable organic acid and inorganic acid salts thereof, Wherein: 1. S.sub.1 is the residue of a non-derivatized monosaccharide selected from the group consisting of pentoses, hexoses and heptoses, 2. S.sub.2 is the residue of a monosaccharide selected from the group consisting of pentoses, hexoses and heptoses which has been derivatized with a substance selected from the group consisting of (a) an aliphatic alcohol containing 1-18 carbon atoms to produce an acetal group at the site of an available hydroxyl residue, (b) an aldehyde containing 1-18 carbon atoms to produce an acetal group at the site of an available hydroxyl residue, (c) a ketone containing 1-18 carbon atoms to produce a ketal group at the site of an available hydroxyl residue, and (d) an organic acid residue containing 1-18 carbon atoms to produce an ester group at the site of an available hydroxyl residue, and 3. Y in each instance is selected from the group consisting of cyclic monovalent nitrogen containing organic radicals and residua and monovalent organic radicals and residua having the general formula ##EQU6## wherein R.sub.1 is a divalent organic radical having a linear carbon chain length of about 1-7 carbon atoms and R.sub.2 and R.sub.3 are selected from the group consisting of --H,--OH,--SH, halogen and monovalent organic radicals and residua having a linear carbon chain length of about 1-7 carbon atoms, and subjecting the said warm blooded animal to an environment wherein it is required to learn tasks or memorize information. 2. The method of claim 1 wherein Y is ##EQU7## R.sub.1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms. 3. The method of claim 1 wherein Y is selected from the group consisting of -(n-propylamino), -(N',N'-dimethylamino-n-propyl), -(N',N'-dimethylaminoisopropyl), -(N-methyl piperidyl), -(N',N'-dimethylaminoethyl), -(N',N'-diethylaminoethyl), and -(2',N',N'-trimethylamino-n-propyl). 4. The method of claim 1 wherein Y is -(N',N'-dimethylamino-n-propyl). 5. The method of claim 1 wherein the said ethereally monosubstituted monosaccharide S.sub.1 --O--Y has the formula ##SPC3## wherein X.sub.1 and Z.sub.1 are selected from the group consisting of H, OH and hydroxyalkyl groups containing up to 2 carbon atoms, Y represents the same organic radicals and residua as set out in claim 1, and one of the OH groups, X.sub.1 or Z.sub.1 in said formula is replaced by --O--Y. 6. The method of claim 5 wherein Y is ##EQU8## R.sub.1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms. 7. The method of claim 5 wherein the said monosaccharide is a hexose. 8. The method of claim 7 wherein Y is ##EQU9## R.sub.1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms. 9. The method of claim 7 wherein Y is selected from the group consisting of -(n-propylamino), -(N',N'-dimethylamino-n-propyl), -(N',N'-dimethylaminoisopropyl), -(N-methyl piperidyl), -(N',N'-dimethylaminoethyl), -(N',N'-diethylaminoethyl), and -(2',N',N'-trimethylamino-n-propyl). 10. The method of claim 9 wherein Y is -(N',N'-dimethylamino-n-propyl). 11. The method of claim 5 wherein the said monosaccharide is selected from the group consisting of glucose and galactose. 12. The method of claim 11 wherein the glucose is monosubstituted in the 1-O- or 3-O- position and the galactose is monosubstituted in the 6-O-position. 13. The method of claim 12 wherein Y is ##EQU10## R.sub.1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms and R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms. 14. The method of claim 12 wherein Y is selected from the group consisting of -(n-propylamino), -(N',N'-dimethylamino-n-propyl), -(N',N'-dimethylaminoisopropyl), -(N-methyl piperidyl), (N',N'-dimethylaminoethyl), -(N',N'-diethylaminoethyl), and -(2',N',N'-trimethylamino-n-propyl). 15. The method of claim 12 wherein Y is -(N',N'-dimethylamino-n-propyl). 16. The method of claim 11 wherein the monosubstituted monosaccharide is selected from the group consisting of 3-O-3'-(n-propylamino)-D-glucose, 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucose, 3-O-4'-(N-methyl piperidyl)-D-glucose, 3-O-2'-(N',N'-dimethylaminoethyl)-D-glucose, 3-O-2'-(N',N'-diethylaminoethyl)-D-glucose, 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-D-glucose, .alpha.-N',N'-dimethylaminoisopropyl-D-glucoside, 6-O-3'-(N',N'-dimethylamino-n-propyl)-D-galactose, 3-O-2'-(N',N'-dimethylaminopropyl)-D-glucose, 6-O-2'-(N',N'-dimethylaminopropyl)-D-galactose, and therapeutically effective and pharmaceutically acceptable organic and inorganic acid salts thereof. 17. The method of claim 11 wherein the monosubstituted monosaccharide is 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucose, or a therapeutically effective and pharmaceutically acceptable organic acid or inorganic acid salt thereof. 18. The method of claim 1 wherein the said ethereal monosubstitution of the monosaccharide derivative S.sub.2 --O--Y has a formula selected from the group consisting of: ##EQU11## ##SPC4## wherein X.sub.2 and Z.sub.2 are selected from the group consisting of H, OH, and monovalent hydroxyalkyl, alkoxyl and alkoxyalkyl radicals containing up to 3 carbon atoms, W is selected from the group consisting of H and monovalent alkyl, alkenyl, cyclic alkane, cyclic aromatic, and acyl radicals containing 1-18 carbon atoms, Y represents the same organic radicals and residua as set out in claim 1, and one of the OH groups, X.sub.2 or Z.sub.2 in said formulae is replaced by --O--Y. 19. The method of claim 18 wherein the said monosaccharide is a hexose. 20. The method of claim 19 wherein Y is ##EQU12## R.sub.1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms. 21. The method of claim 19 wherein Y is selected from the group consisting of -(n-propylamino), -(N',N'-dimethylamino-n-propyl), -(N',N'-dimethylamino isopropyl), -(N-methyl piperidyl), -(N',N'-dimethylaminoethyl), -(N',N'-diethylaminoethyl), and -(2',N',N'-trimethylamino-n-propyl). 22. The method of claim 19 wherein Y is -(N',N'-dimethylamino-n-propyl). 23. The method of claim 18 wherein the said monosaccharide is selected from the group consisting of glucose and galactose. 24. The method of claim 23 wherein the glucose is monosubstituted in the 1-O- or 3-O-position and the galactose is monosubstituted in the 6-O- position. 25. The method of claim 24 wherein Y is ##EQU13## R.sub.1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms and R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms. 26. The method of claim 24 wherein Y is selected from the group consisting of -(n-propylamino), -(N',N'-dimethylamino-n-propyl), -(N',N'-dimethylaminoisopropyl), -(N-methyl piperidyl), -(N',N'-dimethylaminoethyl), -(N,N'-diethylaminoethyl), and -(2',N',N'-trimethylamino-n-propyl). 27. The method of claim 24 wherein Y is -(N',N'-dimethylamino-n-propyl). 28. The method of claim 23 wherein the said ethereal monosubstitution of the monosaccharide derivative is 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylidene-D-glucofuranose , or a therapeutically effective and pharmaceutically acceptable organic acid or inorganic acid salt thereof. 29. The method of claim 1 wherein the said substance is in the form of a salt of an acid selected from the group consisting of HCl, HBr, H.sub.2 SO.sub.4, HNO.sub.3, benzoic acid, p-aminobenzoic acid, p-acetamidobenzoi acid, p-hydroxybenzoic acid, alkane sulfonic acids, p-toluene sulfonic acid, lower alkyl monocarboxylic acids, oxalic acid, tartaric acid, lactic acid, pyruvic acid, malic acid, succinic acid, gluconic acid and glucuronic acid. 30. The method of claim 29 wherein the said substance is 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucose. 31. The method of claim 30 wherein the said acid is HCl. 32. The method of claim 29 wherein the said substance is 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylidene-D-glucofuranose 33. The method of claim 32 wherein the said acid is HCl. 34. The method of claim 23 wherein the said ethereal monosubstitution of the monosaccharide derivative is selected from the group consisting of 3-O-3'-(N',N'-dimethylamino-n-propyl)-1, 2-O-isopropylidene-D-glucofuranose, 3-O-4(N'-methylpiperidyl)-1,2-O-isopropylidene-D-glucofuranose, 3-O-2'-(N',N'-dimethylaminoethyl)-1,2-O-isopropylidene-D-glucofuranose, 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-1, 2-O-isopropylidene-D-glucofuranose, 3-O-2'-(N',N'-dimethylaminopropyl)-1, 2-O-isopropylidene-D-glucofuranose, 6-O-3'-(N',N'-dimethylamino-n-propyl)-1, 2-O-isopropylidene-D-galactopyranose, 6-O-2'-(N',N'-dimethylaminopropyl)-1, 2-O-isopropylidene-D-galactopyranose, 3-O-3'-(N',N'-dimethylamino-n-propyl)-1, 2:5,6-di-O-isopropylidene-D-glucofuranose, 3-O-4'-(N'-methylpiperidyl)-1,2:5, 6-di-O-isopropylidene-D-glucofuranose, 3-O-2'-(N',N'-dimethylaminoethyl)-1,2:5, 6-di-O-isopropylidene-D-glucofuranose, 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-1,2:5,6-di-O-isopropylidene-D-glu cofuranose, 3-O-2'-(N',N'-dimethylaminopropyl)-1 2:5, 6-di-O-isopropylidene-D-glucofuranose, 6-O-3'-(N',N'-dimethylamino-n-propyl)-1 2:3,4-di-O-isopropylidene-D-galactopyranose, 6-O-2'-(N',N'-dimethylaminopropyl)-1, 2:3, 4-di-O-isopropylidene-D-galactopyranose, .alpha.-N',N'-dimethylaminoisopropyl-2, 3:5, 6-di-O-isopropylidene-D-glucofuranoside, and therapeutically effective and pharmaceutically acceptable organic and inorganic acid salts thereof. Other info: Inventors: Gordon, Paul (Chicago, IL, US) Application Number: 465339 Filing Date: 1974-04-29 Publication_date: 1976-06-22 Assignee: Strategic Medical Research Corporation (Chicago, IL) Primary Class(es): 514/25 536/17.4, 536/17.6, 536/17.9, 536/55, 544/251 Other Classes: US Patent Ref:
Other Refs: Primary Examiner: Gotts, Lewis Assistant Examiner: Owens, Cary Attorney: Van Landingham, Jr.; L. S. |
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