US3939146A
Expired / Lapsed
US
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Novel ethereal monosubstitutions of monosaccharide derivatives
Assignee: Alseres Pharmaceuticals Inc
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Filing: 1973-12-14
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Granted: 1976-02-17
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Expires: 1993-12-14
Abstract
Abstract The invention provides a novel therapeutic composition comprising a pharmaceutically acceptable carrier containing a therapeutically effective amount of an ethereal monosubstitution of a monosaccharide derivative having the general formula S--O--Y, wherein S is the residue of the monosaccharide derivative selected from the group consisting of pentoses, hexoses and heptoses as single or polysubstituted acetals, ketals or esters 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 ##EQU1## 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 ethereal monosubstitutions of monosaccharide derivatives, of which 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylidene-D-glucofuranose is an example. The novel monosaccharide derivatives show striking antiviral activity or other therapeutically valuable properties and are useful as active ingredients 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 monosaccharide derivatives.
Inventors
- 👤 Paul Gordon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 09:49
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
35 words
A compound selected from the group consisting of 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylideneglucofuranose, 3-O-4'-(N'-methylpiperidyl)-1,2-O-isopropylidenglucosefuranose, 3-O-2'-(N',N'-dimethylaminoethyl)-1,2-O-isopropylideneglucofuranose, 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-1,2-O-isopropylideneglucofuranose 3-O-2'-(N',N'-dimethylaminopropy)-1,2-O-isopropylideneglucosefuranose, 6-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylidenegalactopyranose, 6-O-2'-(N',N'-dimethylaminopropyl)-1,2-O-isopropylidenegalactopyranose, 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2:5,6-di-O-isopropylideneglucofuranose, 3-O-4'-(N'-methylpiperidyl)-1,2:5,6-di-O-isopropyleneglucofuranose, 3-O-2'-(N',N'-dimethylaminoethyl)-1,2:5,6-di-O-isopropyleneglucofuranose, 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-1,2:5,6-di-O-isopropyleneglucofuranose, 3-O-2'-(N',N'-dimethylaminopropyl)-1,2:5,6-di-O-isopropyleneglucofuranose, 6-O-3'-(N',N'-dimethylamino-n-propyl)-1,2:3,4-di-O-isopropylidenegalactopyranose, 6-O-2'-(N',N'-dimethylaminopropyl)-1,2:3,4-di-O-isopropylidenegalactopyranose, α -N',N'-dimethylamino-iso-propyl-2,3:5,6-di-O-isopropylideneglucofuranoside and therapeutically effective and acceptable organic and inorganic acid salts thereof.
Claim 2
Dependent Claim
35 words
A compound selected from the group consisting of 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylideneglucofuranose, 3-O-4'-(N'-methylpiperidyl)-1,2-O-isopropylidenglucosefuranose, 3-O-2'-(N',N'-dimethylaminoethyl)-1,2-O-isopropylideneglucofuranose, 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-1,2-O-isopropylideneglucofuranose 3-O-2'-(N',N'-dimethylaminopropy)-1,2-O-isopropylideneglucosefuranose, 6-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylidenegalactopyranose, 6-O-2'-(N',N'-dimethylaminopropyl)-1,2-O-isopropylidenegalactopyranose, 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2:5,6-di-O-isopropylideneglucofuranose, 3-O-4'-(N'-methylpiperidyl)-1,2:5,6-di-O-isopropyleneglucofuranose, 3-O-2'-(N',N'-dimethylaminoethyl)-1,2:5,6-di-O-isopropyleneglucofuranose, 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-1,2:5,6-di-O-isopropyleneglucofuranose, 3-O-2'-(N',N'-dimethylaminopropyl)-1,2:5,6-di-O-isopropyleneglucofuranose, 6-O-3'-(N',N'-dimethylamino-n-propyl)-1,2:3,4-di-O-isopropylidenegalactopyranose, 6-O-2'-(N',N'-dimethylaminopropyl)-1,2:3,4-di-O-isopropylidenegalactopyranose, α -N',N'-dimethylamino-iso-propyl-2,3:5,6-di-O-isopropylideneglucofuranoside and therapeutically effective and acceptable organic and inorganic acid salts thereof.
Claim 3
Dependent Claim
35 words
A compound 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)-1,2O-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-glucofuranoside, and therapeutically effective and acceptable organic and inorganic acid salts thereof.
Claim 4
Dependent Claim
35 words
A compound 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)-1,2O-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-glucofuranoside, and therapeutically effective and acceptable organic and inorganic acid salts thereof.
Claim 5
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylidene-D-glucofuranose
Claim 6
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 3-O-4'-(N'-methylpiperidyl)-1,2-O-isopropylidene-D-glucofuranose.
Claim 7
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 3-O-2'-(N',N'-dimethylaminoethyl)-1,2-O-isopropylidene-D-glucofuranose.
Claim 8
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-1,2-O-isopropylidene-D-gulcofuranose.
Claim 9
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 3-O-2'-(N',N'-dimethylaminopropyl)-1,2-O-isopropylidene-D-glucofuranose.
Claim 10
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 6-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylidene-D-galactopyranose.
Claim 11
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 6-O-2'-(N',N'-dimethylaminopropyl)-1,2-O-isopropylidene-D-galactopyranose.
Claim 12
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2:5,6-di-O-isopropylidene-D-glucofuranose.
Claim 13
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 3-O-4'-(N'-methylpiperidyl)-1,2:5,6-di-O-isopropylidene-D-gulcofuranose.
Claim 14
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 3-O-2'-(N',N'-dimethylaminoethyl)-1,2:5,6-di-O-isopropylidene-D-glucofuranose.
Claim 15
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 3-O-3'-(2',N',N'-trimethylamino-n-propyl)-1,2:5,6-di-O-isopropylidene-D-glucofuranose.
Claim 16
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 3-O-2'-(N',N'-dimethylaminopropyl)-1,2:5,6-di-O-isopropylidene-D-glucofuranose.
Claim 17
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 6-O-3'-(N',N'-dimethylamino-n-propyl)-1,2:3,4-di-O-isopropylidene-D-galactopyranose.
Claim 18
Dependent Claim
12 words
A compound in accordance with claim 2 wherein the compound is 6-O-2'-(N',N'-dimethylaminopropyl)-1,2:3,4-di-O-iospropylidene-D-galactopyranose.
Claim 19
Dependent Claim
13 words
A compound in accordance with claim 2 wherein the compound is α -N',N'-dimethylamino-iso-propyl-2,3:5,6-O-isopropylidene-D-glucofuranoside.
Claim 20
Dependent Claim
71 words
A compound in accordance with claim 1 wherein the compound 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 21
Dependent Claim
13 words
A compound in accordance with claim 18 wherein the said compound is 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylideneglucofuranose.
Claim 22
Dependent Claim
13 words
A compound in accordance with claim 19 wherein the said acid is HCl.
Claim 23
Dependent Claim
71 words
A compound in accordance with claim 2 wherein the compound 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 24
Dependent Claim
13 words
A compound in accordance with claim 21 wherein the said compound is 3-O-3'-(N',N'-dimethylamino-n-propyl)-1,2-O-isopropylidene-D-glucofuranose.
Claim 25
Dependent Claim
13 words
A compound in accordance with claim 22 wherein the said acid is HCl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-02-16 | 1979-08-18 | 1980-02-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-02-16 | 1983-08-18 | 1984-02-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-02-16 | 1987-08-18 | 1988-02-17 | $7700.00 | Window Closed / Lapsed |