US4631272A
Expired / Lapsed
US
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N-acylated 1-alkylamino-1-deoxy-ketose derivatives, a process for their preparation and their use
Assignee: Bayer AG
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Filing: 1985-02-08
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Granted: 1986-12-23
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Expires: 2005-02-08
Abstract
Abstract Compounds of the formula ##STR1## in which R 1 represents hydrogen or an optionally substituted, straight-chain or branched alkyl or mono- or poly-unsaturated alkenyl radical with in each case up to 30 C atoms, X represents CH 2 , O, S or NR, wherein R denotes hydrogen or an alkyl group with up to 20 C atoms, and R 2 represents hydrogen or an optionally substituted, straight-chain or branched, saturated or mono- or poly-unsaturated hydrocarbon radical with up to 30 C atoms, or pharmaceutically acceptable salts thereof, stimulate the immune system and help fight infection.
Inventors
- 👤 Oswald Lockhoff
- 👤 Bernd-Wieland Kruger
- 👤 Peter Stadler
- 👤 Karl G. Metzger
- 👤 Hein-Peter Kroll
- 👤 Klaus Schaller
- 👤 Hans-Joachim Zeiler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 14:41
CPC Classifications
C; C07; C07H; C07H3/00; C07H13/00; C07H13/02; C07H13/04; A; A61; A61P; A61P31/00; A61P31/04; C07H13/06; C07H13/12; C07H15/00; C07H15/02; C07H15/12; C07H7/00; C07H7/02
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
95 words
A compound of the formulae Ia to Ic ##STR5## in which R 1 represents hydrogen or a straight-chain or branched alkyl or mono or poly-unsaturated alkenyl radical with in each case up to 30 carbon atoms and optionally substituted by phenyl, halogen, amino, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, OH, C 1 -C 6 -alkoxy, SH, C 1 -C 6 -alkyl--COO and C 1 -C 6 -alkyl--CO--NH, X represents CH 2 , O, S or NR, wherein R denotes hydrogen or an alkyl group with up to 20 carbon atoms, and
Claim 2
Dependent Claim
95 words
A compound of the formulae Ia to Ic ##STR5## in which R 1 represents hydrogen or a straight-chain or branched alkyl or mono or poly-unsaturated alkenyl radical with in each case up to 30 carbon atoms and optionally substituted by phenyl, halogen, amino, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, OH, C 1 -C 6 -alkoxy, SH, C 1 -C 6 -alkyl--COO and C 1 -C 6 -alkyl--CO--NH, X represents CH 2 , O, S or NR, wherein R denotes hydrogen or an alkyl group with up to 20 carbon atoms, and
Claim 3
Dependent Claim
63 words
R 2 represents hydrogen or a straight-chain or branched, saturated or mono- or poly-unsaturated hydrocarbon radical with up to 30 carbon atoms and optionally substituted by phenyl, halogen, amino, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, OH, C 1 -C 6 -alkoxy, SH, C 1 -C 6 -alkyl--COO and C 1 -C 6 -alkyl--CO--NH, or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
63 words
R 2 represents hydrogen or a straight-chain or branched, saturated or mono- or poly-unsaturated hydrocarbon radical with up to 30 carbon atoms and optionally substituted by phenyl, halogen, amino, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, OH, C 1 -C 6 -alkoxy, SH, C 1 -C 6 -alkyl--COO and C 1 -C 6 -alkyl--CO--NH, or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
75 words
A compound or salt according to claim 1, in which R 1 represents an optionally substituted straight-chain or branched alkyl radical with 7-21 carbon atoms or a mono- or di-unsaturated straight-chain or branched alkenyl radical with 7-21 carbon atoms and optionally substituted by phenyl, halogen, amino, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, OH, C 1 -C 6 -alkoxy, SH, C 1 -C 6 -alkyl--COO and C 1 -C 6 -alkyl --CO--NH.
Claim 6
Dependent Claim
16 words
A compound or salt according to claim 1, in which R 2 has 1-20 carbon atoms.
Claim 7
Dependent Claim
17 words
A compound according to claim 1, wherein the compound is 1-deoxy-1-(N-dodecyl-octadecanoylamido)-D-fructose or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
17 words
A compound according to claim 1, wherein the compound is 1-deoxy-1-(N-tetradecyl-octadecanoylamido)-D-fructose or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
17 words
A compound according to claim 1, wherein the compound is 1-deoxy-1-(N-octadecyl-dodecanoylamido)-D-fructose or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
17 words
A compound according to claim 1, wherein the compound is 1-deoxy-1-(N-octadecyl-octadecanoylamido)-D-fructose or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
17 words
A compound according to claim 1, wherein the compound is 1-deoxy-1-(N-dodecyl-dodecanoylamido)-D-tagatose or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
17 words
A compound according to claim 1, wherein the compound is 1-deoxy-1-(N-octadecyl-dodecanoylamido)-D-tagatose or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
17 words
A compound according to claim 1, wherein the compound is 1-deoxy-1-(N-octadecyl-octadecanoylamido)-D-tagatose or a pharmaceutically acceptable salt thereof,
Claim 14
Dependent Claim
22 words
An immunostimulating composition comprising an immunostimulating effective amount of a compound or salt according to claim 1 in admixture with a diluent.
Claim 15
Dependent Claim
15 words
A unit dose of a composition according to claim 1 in admixture with a diluent.
Claim 16
Dependent Claim
29 words
A method of stimulating the immune system of an animal which comprises administering to such animal an immunostimulating effective amount of a compound or salt according to claim 1.
Claim 17
Dependent Claim
30 words
The method according to claim 13, wherein such compound is selected from the group consisting of 1-deoxy-1-(N-dodecyl-octadecanoylamido)-D-fructose, 1-deoxy-1-(N-tetradecyl-octadecanoylamido)-D-fructose, 1-deoxy-1-(N-octadecyl-dodecanoylamido)-D-fructose, 1-deoxy-1-(N-octadecyl-octadecanoylamido)-D-fructose, 1-deoxy-1-(N-dodecyl-dodecanoylamido)-D-tagatose, 1-deoxy-1-(N-octadecyl-dodecanoylamido)-D-tagatose or 1-deoxy-1-(N-octadecyl-octadecanoylamido)-D-tagatose or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
141 words
Process for the preparation of the compounds according to claim 1, comprising (a) reacting a hexose with an amino compound of the formula R 1 --NH 2 , to give a glycosylamino of the formula II ##STR6## (b) rearranging the glycosylamine II into an N-alkylisated 1-amino-1-deoxyketose of the formula III ##STR7## by the procedure of an Amadori rearrangement, and (c) introducing the group --COX--R 2 into the compounds III with a reagent selected from the group consisting of R 2 --CH 2 --CO--Y, Y--CO--O--R 2 , R 2 --NCO, an aromatic halogenoformic acid ester plus a primary amine R 2 --NH 2 or secondary amine R 2 --NH-alkyl and R 2 --S--CO--Y, Y being selected from the group consisting of halogen, O--CO--R 2 and O--CO--O--R 2 , wherein R 1 , R 2 and X are as defined in claim 1.
References Cited (Backward Citations)
GB866734A
Cited
US3005750A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-12-22 | 1990-06-23 | 1990-12-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-12-22 | 1994-06-23 | 1994-12-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-12-22 | 1998-06-23 | 1998-12-23 | $7700.00 | Window Closed / Lapsed |