Therapeutic composition and method of therapeutically treating warm blooded animals therewith

Claim 2

A novel therapeutic composition comprising a pharmaceutically acceptable carrier containing a therapeutically effective amount of at least one substance selected from the group consisting of an etheral monosubstitution of a monosaccharide derivative having the formula S--O--Y, and therapeutically effective and pharmaceutically acceptable organic acid and inorganic acid salts thereof, wherein S is the residue of a monosaccharide selected from the group consisting of pentoses, hexoses and heptoses which has been derivatized with at least one substance selected from the group consisting of (a) at least one aliphatic alcohol containing 1-18 carbon atoms to produce an acetal group at the site of at least one available hydroxyl group, (b) at least one aldehyde containing 1-18 carbon atoms to produce at least one acetal group at the site of at least one available hydroxyl group, (c) at least one ketone containing 1-18 carbon atoms to produce at least one ketal group at the site of at least one available hydroxyl group, and (d) at least one organic acid residue containing 1-18 carbon atoms to produce an ester group at the site of at least one available hydroxyl group, and Y is selected from the group consisting of cyclic monovalent nitrogen containing organic radicals and monovalent organic radicals having the formula ##STR6##wherein R 1 is a divalent organic radical having a linear crbon 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 having a linear carbon chain length of about 1-7 carbon atoms.

Claim 3

A novel therapeutic composition in accordance with claim 1 wherein Y is ##STR7##R 1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R 2 and R 3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms.

Claim 4

A novel therapeutic composition in accordance with 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).

Claim 5

A novel therapeutic composition in accordance with claim 1 wherein Y is -(N',N'-dimethylamino-n-propyl).

Claim 6

A novel therapeutic compostion in accordance with claim 1 wherein the said ethereal monosubstitution of the monosaccharide derivative has a formula selected from the group consisting of: ##STR8##wherein X and Z 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 as set out in claim 1, and one of the OH groups, X or Z in said formula is replaced by --O--Y.

Claim 7

A novel therapeutic composition in accordance with claim 5 wherein Y is ##STR9##R 1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R 2 and R 3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms.

Claim 8

A novel therapeutic composition in accordance with claim 5 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'-triemthylamino-n-propyl).

Claim 9

A novel therapeutic composition in accordance with claim 5 wherein Y is -(N',N'-dimethylamino-n-propyl).

Claim 10

A novel therapeutic composition in accordance with claim 5 wherein the monosaccharide is a hexose.

Claim 11

A novel therapeutic composition in accordance with claim 9 wherein Y is ##STR10##R 1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R 2 and R 3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms.

Claim 12

A novel therapeutic composition in accordance with claim 9 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'-triemthylamino-n-propyl).

Claim 13

A novel therapeutic composition in accordance with claim 9 wherein Y is -(N',N'-dimethylamino-n-propyl).

Claim 14

A novel therapeutic composition in accordance with claim 5 wherein the monosaccharide is selected from the group consisting of glucose and galactose.

Claim 15

A novel therapeutic composition in accordance with claim 13 wherein the glucose is monosubstituted in the 1-O- or 3-O- position and the galactose is monosubstituted in the 6-O- position.

Claim 16

A novel therapeutic composition in accordance with claim 14 wherein Y is ##STR11##R 1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R 2 and R 3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms.

Claim 17

A novel therapeutic composition in accordance with claim 14 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).

Claim 18

A novel therapeutic composition in accordance with claim 14 wherein Y is -(N',N'-dimethylamino-n-propyl).

Claim 19

A novel therapeutic composition in accordance with claim 13 wherein the 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-glucofuranose, 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, -N',N'dimethylamino-iso-propyl-2,3:5, 6-di-O-isopropylidene-D-glucofuranoside, and therapeutically effective and pharmaceutically accepatable organic and inorganic acid salts thereof.

Claim 20

A novel therapeutic composition in accordance with claim 13 wherein the ethereal monosubstitution of the monosaccharide derivative is 3-O-3'-(N',N'-dimethylamino-N-propyl)-1, 2-O-isopropylidene-D-glucofuranose.

Claim 23

The method of claim 20 wherein Y is ##STR13##R 1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R 2 and R 3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms.

Claim 24

The method of claim 20 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).

Claim 25

The method of claim 20 wherein Y is -(N',N'-dimethylamino-n-propyl).

Claim 26

The method of claim 20 wherein the said ethereal monosubstitution of the monosaccharide derivative has a formula selected from the group consisting of: ##STR14##wherein X and Z 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 or Z in said formula is replaced by --O--Y.

Claim 27

The method of claim 24 wherein Y is ##STR15##R 1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R 2 and R are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms.

Claim 28

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).

Claim 29

The method of claim 24 wherein Y is -(N',N'-dimethylamino-n-propyl).

Claim 30

The method of claim 24 wherein the monosaccharide is a hexose.

Claim 31

The method of claim 28 wherein Y is ##STR16##R 1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms, and R 2 and R 3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms.

Claim 32

The method of claim 28 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).

Claim 33

The method of claim 28 wherein Y is -(N',N'-dimethylamino-n-propyl).

Claim 34

The method of claim 24 wherein the monosaccharide is selected from the group consisting of glucose and galactose.

Claim 35

The method of claim 32 wherein the glucose is monosubstituted in the 1-O- or 3-O-position and the galactose is monosubstituted in the 6-O- position.

Claim 36

The method of claim 33 wherein Y is ##STR17##R 1 is a hydrocarbon radical having a linear carbon chain length of 1-3 carbon atoms and R 2 and R 3 are selected from the group consisting of hydrogen and hydrocarbon radicals having a linear carbon chain length of 1-3 carbon atoms.

Claim 37

The method of claim 33 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).

Claim 38

The method of claim 33 wherein Y is -(N',N'-dimethylamino-n-propyl).

Claim 39

The method of claim 32 wherein the 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-glucofuranose, 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, α-N',N'-dimethylamino-iso-propyl-2, 3:5, 6-di-O-isopropylidene-D-glucofurnaoside, and organic and inorganic acid salts thereof.

Claim 40

The method of claim 32 wherein the etereal monosubstitution of the monosaccharide derivative is 3-O-3'-(N',N'-dimethylamino-n-propyl)-1, 2-O-isopropylidene-D-glucofuranose.

Claim 41

In a method of growing tissue culture cells in a tissue culture medium in the absence of a viral infection wherein the tissue culture cells tend to die after being grown in the tissue culture medium over an extended period of time, the improvement which comprises increasing the life span of the tissue culture cells by growing them in a tissue culture medium which contains an effective amount of at least one substance selected from the group consisting of an ethereal monosubstitution of a monosaccharide derivative having the formula S--O--Y, and therapeutically effective and pharmaceutically acceptable organic acid and inorganic acid salts thereof, wherein S is the residue of a monosaccharide selected from the group consisting of pentoses, hexoses and heptoses which has been derivatized with at least one substance selected from the group consisting of (a) at least one aliphatic alcohol containing 1-18 carbon atoms to produce an acetal group at the site of at least one available hydroxyl group (b) at least one aldehyde containing 1-18 carbon atoms to produce at least one acetal group at the site of at least one available hydroxyl group (c) at least one ketone containing 1-18 carbon atoms to produce at least one ketal group at the site of at least one available hydroxyl group, and (d) at least one organic acid residue containing 1-18 carbon atoms to produce an ester group at the site of at least one available hydroxyl group, and Y is selected from the group consisting of cyclic monovalent nitrogen containing organic radicals and monovalent organic radicals having the formula ##STR18##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 having a linear carbon chain length of about 1-7 carbon atoms.

Claim 42

In a method of growing tissue culture cells in a tissue culture medium in the absence of a viral infection wherein the tissue culture cells tend to die after being grown in the tissue culture medium over an extended period of time, the improvement which comprises increasing the life span of the tissue culture cells by growing them in a tissue culture medium which contains an effective amount of at least one substance selected from the group consisting of an ethereal monosubstitution of a monosaccharide derivative having the formula S--O--Y, and therapeutically effective and pharmaceutically acceptable organic acid and inorganic acid salts thereof, wherein S is the residue of a monosaccharide selected from the group consisting of pentoses, hexoses and heptoses which has been derivatized with at least one substance selected from the group consisting of (a) at least one aliphatic alcohol containing 1-18 carbon atoms to produce an acetal group at the site of at least one available hydroxyl group (b) at least one aldehyde containing 1-18 carbon atoms to produce at least one acetal group at the site of at least one available hydroxyl group (c) at least one ketone containing 1-18 carbon atoms to produce at least one ketal group at the site of at least one available hydroxyl group, and (d) at least one organic acid residue containing 1-18 carbon atoms to produce an ester group at the site of at least one available hydroxyl group, and Y is selected from the group consisting of cyclic monovalent nitrogen containing organic radicals and monovalent organic radicals having the formula ##STR18##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 having a linear carbon chain length of about 1-7 carbon atoms.

Claim 43

The method of claim 39 wherein the ethereal monosubstitution of the monosaccharide derivative is 3-O-3'-(N',N'-dimethylamino-n-propyl)-1, 2-O-isopropylidene-D-glucofuranose.

Claim 44

The method of claim 39 wherein the tissue culture cells being grown in the tissue culture medium are human embryo cells.

Claim 45

The method of claim 41 wherein the ethereal monosubstitution of the monosaccharide derivative is 3-O-3'-(N',N'-dimethylamino-n-propyl)-1, 2-O-isopropylidene-D-glucofuranose.

Claim 48

The method of claim 43 wherein the ethereal monosubstitution of the monosaccharide derivative is 3-O-3'-(N',N'-dimethylamino-n-propyl)-1, 2-O-isopropylidene-D-glucofuranose.

Claim 49

A novel therapeutic composition in accordance with 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 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.

Claim 50

The novel therapeutic composition in accordance with claim 45 wherein the said acid is HCl.

Claim 51

The novel therapeutic composition in accordance with claim 19 wherein the said 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucose is in the form of a salt of an acid 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.

Claim 52

The novel therapeutic composition in accordance with claim 47 wherein the said acid is HCl.

Claim 53

The method of claim 20 wherein the said substance is in the form of a salt of an acid 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.

Claim 54

The method of claim 49 wherein the said acid is HCl.

Claim 55

The method of claim 38 wherein the said 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucose is in the form of a salt of an acid 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.

Claim 56

The method of claim 51 wherein the said acid is HCl.