Novel ethereally monosubstituted monosaccharides

Abstract

The invention provides a novel therapeutic composition comprising a pharmaceutically acceptable carrier containing a therapeutically effective amount of an ethereally monosubstituted monosaccharide having the general formula S--O--Y, wherein S is the residue of a monosaccharide selected from the group consisting of pentoses, hexoses and heptoses and Y 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 ##STR1## wherein R 1 is a divalent organic radical having a linear carbon chain length of about 1-7 carbon atoms and R 2 and R 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. The invention also provides certain novel ethereally monosubstituted monosaccharides, of which 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucose is an example. The novel monosaccharides show striking antiviral activity or other therapeutically valuable properties and are useful as an active ingredient in the above therapeutic composition. The invention further provides a method of therapeutically treating warm blooded animals with the aforementioned therapeutic composition and novel monosubstituted monosaccharides.

I claim: 
     
       1. A compound selected from the group consisting of 3-O-3'-(N',N'-dimethylamino-n-propyl)-glucose,   3-O-4'-(N-methyl piperidyl)-glucose,   3-O-2'-(N',N'-dimethylaminoethyl)-glucose,   3-O-3'-(2',N',N'-trimethylamino-n-propyl)-glucose,   α-N,N-dimethylaminoisopropyl-glucoside,   6-O-3'-(N',N'-dimethylamino-n-propyl)-galactose   3-O-2'-(N',N'-dimethylaminopropyl)-glucose,   6-O-2'-(N',N'-dimethylaminopropyl)-galactose, and therapeutically effective and acceptable organic acid and inorganic acid salts thereof.   
     
     
       2. A compound in accordance with claim 1 wherein the said compound is 3-O-3'-(N',N'-dimethylamino-n-propyl)-glucose. 
     
     
       3. A compound in accordance with claim 1 wherein the said compound is 3-O-4'-(N-methyl piperidyl)-glucose. 
     
     
       4. A compound in accordance with claim 1 wherein the said compound is 3-O-2'-(N',N'-dimethylaminoethyl)-glucose. 
     
     
       5. A compound in accordance with claim 1 wherein the said compound is 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-glucose. 
     
     
       6. A compound in accordance with claim 1 wherein the said compound is α-N,N-dimethylaminoisopropyl-glucoside. 
     
     
       7. A compound in accordance with claim 1 wherein the said compound is 6-O-3'-(N',N'-dimethylamino-n-propyl)-galactose. 
     
     
       8. A compound in accordance with claim 1 wherein the said compound is 3-O-2'-(N',N'-dimethylaminopropyl)-glucose. 
     
     
       9. A compound in accordance with claim 1 wherein the said compound is 6-O-2'-(N',N'-dimethylaminopropyl)-galactose. 
     
     
       10. A compound selected from the group consisting of 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucopyranose,   3-O-4'-(N-methyl piperidyl)-D-glucopyranose,   3-O-2'-(N',N'-dimethylaminoethyl)-D-glucopyranose,   3-O-3'-(2',N',N'-trimethylamino-n-propyl)-D-glucopyranose,   α-N,N-dimethylaminoisopropyl-D-glucoside,   6-O-3'-(N',N'-dimethylamino-n-propyl)-D-galactopyranose,   3-O-2'-(N',N'-dimethylaminopropyl)-D-glucopyranose,   6-O-2'-(N',N'-dimethylaminopropyl)-D-galactopyranose, and therapeutically effective and acceptable organic acid and inorganic acid salts thereof.   
     
     
       11. A compound in accordance with claim 10 wherein the said compound is 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucopyranose. 
     
     
       12. A compound in accordance with claim 10 wherein the said compound is 3-O-4'-(N-methylpiperidyl)-D-glucopyranose. 
     
     
       13. A compound in accordance with claim 10 wherein the said compound is 3-O-2'-(N',N'-dimethylaminoethyl) D-glucopyranose. 
     
     
       14. A compound in accordance with claim 10 wherein the said compound is 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-D-glucopyranose. 
     
     
       15. A compound in accordance with claim 10 wherein the said compound is α-N,N-dimethylaminoisopropyl-D-glucoside. 
     
     
       16. A compound in accordance with claim 10 wherein the said compound is 6-O-3'-(N',N'-dimethylamino-n-propyl)-D-galactopyranose. 
     
     
       17. A compound in accordance with claim 10 wherein the said compound is 3-O-2'-(N',N'-dimethylaminopropyl)-D-glucopyranose. 
     
     
       18. A compound in accordance with claim 10 wherein the said compound is 6-O-2'-(N',N'-dimethylaminopropyl)-D-galactopyranose. 
     
     
       19. A compound in accordance with claim 1 wherein the compound is in the form of a salt of the said organic and inorganic acids, the said acids being selected from the group consisting of HCl, HBr, H 2  SO 4 , HNO 3 , benzoic acid, p-aminobenzoic acid, p-acetamidobenzoic 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. 
     
     
       20. A compound in accordance with claim 10 wherein the compound is in the form of a salt of the said organic and inorganic acids, the said acids being selected from the group consisting of HCl, HBr, H 2  SO 4 , HNO 3 , benzoic acid, p-aminobenzoic acid, p-acetamidobenzoic 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. 
     
     
       21. A compound in accordance with claim 19 wherein the said compound is 3-O-3'-(N',N'-dimethylamino-n-propyl)-glucose. 
     
     
       22. A compound in accordance with claim 21 wherein the said acid is HCl. 
     
     
       23. A compound in accordance with claim 20 wherein the said compound is 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucopyranose. 
     
     
       24. A compound in accordance with claim 23 wherein the said acid is HCl. .Iadd. 25. An ethereally monosubstituted monosaccharide having the formula S-O-Y, and therapeutically effective and acceptable organic and inorganic acid salts thereof, wherein S is the residue of a monosaccharide selected from the group consisting of pentoses, hexoses and heptoses and Y is selected from the group consisting of N',N'-dimethylamino-n-propyl, N',N'-dimethylaminoisopropyl, N-methyl piperidyl, N',N'-dimethylaminoethyl, and 2',N',N'-trimethylamino-n-propyl. .Iaddend..Iadd. 26. A compound according to claim 25 wherein the monosaccharide is a hexose. .Iaddend..Iadd. 27. A compound according to claim 26 wherein said hexose is glucose. .Iaddend..Iadd. 28. A compound according to claim 27 wherein said glucose is ethereally monosubstituted at the 1-O- or 6-O-position. .Iaddend..Iadd. 29. A compound according to claim 28 wherein said glucose is D-glucopyranose. .Iaddend..Iadd. 30. A compound according to claim 26 wherein said hexose is galactose. .Iaddend..Iadd. 31. A compound according to claim 30 wherein said galactose is substituted at the 6-O-position. .Iaddend..Iadd. 32. A compound according to claim 31 wherein said galactose is D-galactopyranose. .Iaddend..Iadd. 33. An ethereally monosubstituted monosaccharide having the formula S-O-Y, and therapeutically effective and acceptable organic and inorganic acid salts thereof, wherein S is the residue of a monosaccharide selected from the group consisting of pentoses, hexoses and heptoses and Y is selected from the group consisting of N'-methylamino-n-propyl, N'-ethyl-N'-methylamino-n-propyl, N'-ethylamino-n-propyl, N',N'-dimethylamino-1,2-propenyl, N',N'-dimethylamino-sec.-butyl, dimethylaminobutyl, piperidyl, methylpiperidyl and methylpyrrolidyl. .Iaddend..Iadd. 34. A compound according to claim 33 wherein said monosaccharide is a hexose. .Iaddend..Iadd. 35. A compound according to claim 34 wherein said hexose is glucose. .Iaddend..Iadd. 36. A compound according to claim 35 wherein said glucose is ethereally monosubstituted at the 1-O- or 3-O-position. .Iaddend..Iadd. 37. A compound according to claim 34 wherein said hexose is galactose. .Iaddend..Iadd. 38. A compound according to claim 37 wherein said galactose is ethereally monosubstituted at the 6-O-position. .Iaddend.