US4062950A
Expired / Lapsed
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Amino sugar derivatives
Assignee: Bayer AG
•
Filing: 1976-02-02
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Granted: 1977-12-13
•
Expires: 1996-02-02
Abstract
Abstract New amino sugars which are glucopyranosyl and oligoglucosidyl derivatives of 4,6-bisdesoxy-4-(4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-en-1-ylamino)-α-D-glucopyranose inhibit glycoside hydrolases of the digestive tract. The compounds, of which O-{4,6-bisdesoxy-4-[1S-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-en-1-ylamino]-α-D-glucopyranosyl}-(1→4)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranose is a representative embodiment, demonstrate both saccharase and amylase inhibiting properties.
Inventors
- 👤 Werner Frommer
- 👤 Bodo Junge
- 👤 Uwe Keup
- 👤 Lutz Muller
- 👤 Walter Puls
- 👤 Delf Schmidt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 02:29
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/207; C12; C12P; C12P19/00; C12P19/26; C12P19/28; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/827
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
9 words
The compound 0-{4,6-bisdesoxy-4-[1S-(1,4,6/5)-4,5,6-thihydroxy-3-hydroxymethylcyclohex-2-en-1-ylamino]-α-D-glucopyranosyl}-(1→4)-D-glucopyranose of the conformational structural formula: ##STR12##
Claim 2
Dependent Claim
9 words
The compound 0-{4,6-bisdesoxy-4-[1S-(1,4,6/5)-4,5,6-thihydroxy-3-hydroxymethylcyclohex-2-en-1-ylamino]-α-D-glucopyranosyl}-(1→4)-D-glucopyranose of the conformational structural formula: ##STR12##
Claim 3
Dependent Claim
31 words
The method of inhibiting glucoside hydrolases in the digestive tract of humans and animals which comprises administering thereto at least an effective inhibitory amount of a compound according to claim 1.
Claim 4
Dependent Claim
33 words
A pharmaceutical composition for effecting inhibition of glucoside hydrolases in humans and animals comprising an effective inhibitory amount of a compound according to claim 1 in combination with an inert, compatible pharmaceutical carrier.
Claim 5
Dependent Claim
33 words
A foodstuff composition for effecting inhibition of glucoside hydrolases in humans and animals comprising an effective inhibitory amount of a compound according to claim 1 in combination with an inert, compatible foodstuff carrier.
Claim 6
Dependent Claim
9 words
The compound 0-{4,6-bisdesoxy-4[1S-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethycyclohex-2-en-1-ylamino]-α-D-glucopyranosyl}-(1→4)-0-α-D-glucopyranosyl-(1→4)-D-glucopyranose of the conformational structural formula: ##STR13##
Claim 7
Dependent Claim
9 words
The compound 0-{4,6-bisdesoxy-4[1S-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethycyclohex-2-en-1-ylamino]-α-D-glucopyranosyl}-(1→4)-0-α-D-glucopyranosyl-(1→4)-D-glucopyranose of the conformational structural formula: ##STR13##
Claim 8
Dependent Claim
31 words
The method of inhibiting glucoside hydrolases in the digestive tract of humans and animals which comprises administering thereto at least an effective inhibitory amount of a compound according to claim 5.
Claim 9
Dependent Claim
33 words
A pharmaceutical composition for effecting inhibition of glucoside hydrolases in humans and animals comprising an effective inhibitory amount of a compound according to claim 5 in combination with an inert, compatible pharmaceutical carrier.
Claim 10
Dependent Claim
33 words
A foodstuff composition for effecting inhibition of glucoside hydrolases in humans and animals comprising an effective inhibitory amount of a compound according to claim 5 in combination with an inert, compatible foodstuff carrier.
Claim 11
Dependent Claim
11 words
The compound 0-{4,6-bisdesoxy-4-[1 S-(1,4 6/5)-4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-en-1-ylamino]-α-D-glucopyranosyl}-(1→4)-0-α-D-glucopyranosyl-(1→4)-0-.alpha.-D-glucopyranosyl-(1→4)-D-glycopyranose of the conformational structural formula: ##STR14##
Claim 12
Dependent Claim
11 words
The compound 0-{4,6-bisdesoxy-4-[1 S-(1,4 6/5)-4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-en-1-ylamino]-α-D-glucopyranosyl}-(1→4)-0-α-D-glucopyranosyl-(1→4)-0-.alpha.-D-glucopyranosyl-(1→4)-D-glycopyranose of the conformational structural formula: ##STR14##
Claim 13
Dependent Claim
31 words
The method of inhibiting glucoside hydrolases in the digestive tract of humans and animals which comprises adminstering thereto at least an effective inhibitory amount of a compound according to claim 9.
Claim 14
Dependent Claim
34 words
A pharmaceutical composition for effecting inhibition of glucoside hydrolases in humans and animals comprising an effective inhibitory amount of a compound according to claim 9 in combination with an inert, compatible pharmaceutical or carrier.
Claim 15
Dependent Claim
33 words
A foodstuff composition for effecting inhibition of glucoside hydrolases in humans and animals comprising an effective inhibitory amount of a compound according to claim 9 in combination with an inert, compatible foodstuff carrier.
Claim 16
Dependent Claim
10 words
The compound 0{4,6-bisdesoxy-4-[1 S-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-4-0-α-D-glycopyranosyl-(1→4)-cyclohex-2-en-1-ylamino]-α-D-glycopyranosyl}-(1→4)-0-α-D-glucopyranosyl-(1→4)-D-glucopyranose of the conformational structural formula: ##STR15##
Claim 17
Dependent Claim
10 words
The compound 0{4,6-bisdesoxy-4-[1 S-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-4-0-α-D-glycopyranosyl-(1→4)-cyclohex-2-en-1-ylamino]-α-D-glycopyranosyl}-(1→4)-0-α-D-glucopyranosyl-(1→4)-D-glucopyranose of the conformational structural formula: ##STR15##
Claim 18
Dependent Claim
31 words
The method of inhibiting glucoside hydrolases in the digestive tract of humans and animals which comprises administering thereto at least an effective inhibitory amount of a compound according to claim 13.
Claim 19
Dependent Claim
33 words
A pharmaceutical composition for effecting inhibition of glucoside hydrolases in humans and animals comprising an effective inhibitory amount of a compound according to claim 13 in combination with an inert, compatible pharmaceutical carrier.
Claim 20
Dependent Claim
33 words
A foodstuff composition for effecting inhibition of glucoside hydrolases in humans and animals comprising an effective inhibitory amount of a compound according to claim 13 in combination with an inert, compatible foodstuff carrier.
Claim 21
Dependent Claim
82 words
An amino sugar produced by microorganisms of the family Actinoplanaceae consisting of a 4,6- bisdesoxy-4-(4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-en-1- ylamino)-α-D-glucopyranose of the formula: ##STR16## glycosidically linked with n glucose units, where n is 4, 5, 6, 7 or 8, which units are present as either one or two α-1:4 oligosaccharide chains or as one glucose unit and one α-1:4 oligosaccharide chain, said amino sugar yielding upon total acid hydrolysis the compound ##STR17## and glucose in a molar ratio of 1:n wherein n is as defined above.
Claim 22
Dependent Claim
82 words
An amino sugar produced by microorganisms of the family Actinoplanaceae consisting of a 4,6- bisdesoxy-4-(4,5,6-trihydroxy-3-hydroxymethylcyclohex-2-en-1- ylamino)-α-D-glucopyranose of the formula: ##STR16## glycosidically linked with n glucose units, where n is 4, 5, 6, 7 or 8, which units are present as either one or two α-1:4 oligosaccharide chains or as one glucose unit and one α-1:4 oligosaccharide chain, said amino sugar yielding upon total acid hydrolysis the compound ##STR17## and glucose in a molar ratio of 1:n wherein n is as defined above.
Claim 23
Dependent Claim
11 words
An amino sugar according to claim 17 wherein n is 4.
Claim 24
Dependent Claim
12 words
An amino sugar according to claim 18 which has the formula: ##STR18##
Claim 25
Dependent Claim
11 words
An amino sugar according to claim 17 wherein n is 5.
Claim 26
Dependent Claim
12 words
An amino sugar according to claim 20 which has the formula: ##STR19##
Claim 27
Dependent Claim
11 words
An amino sugar according to claim 17 wherein n is 6.
Claim 28
Dependent Claim
12 words
An amino sugar according to claim 22 which has the formula: ##STR20##
Claim 29
Dependent Claim
11 words
An amino sugar according to claim 17 wherein n is 7.
Claim 30
Dependent Claim
12 words
An amino sugar according to claim 24 which has the formula: ##STR21##
Claim 31
Dependent Claim
11 words
An amino sugar according to claim 17 wherein n is 8.
Claim 32
Dependent Claim
11 words
An amino sugar according to claim 26 which has the formula:
Claim 33
Dependent Claim
32 words
The method of inhibiting glucoside hydrolases in the digestive tract of humans and animals which comprises administering thereto at least an effective inhibitory amount of an amino sugar according to claim 17.
Claim 34
Dependent Claim
33 words
A pharmaceutical composition for effecting inhibition of glucoside hydrolases in humans and animals comprising an effective inhibitory amount of amino sugar according to claim 17 in combination with an inert, compatible pharmaceutical carrier.
Claim 35
Dependent Claim
34 words
A foodstuff composition for effecting inhibition of glucoside hydrolases in humans and animals comprising an effective inhibitory amount of amino sugar according to claim 17 in combination with an inert, compatible foodstuff carrier. --
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) | 1980-12-12 | 1981-06-13 | 1981-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-12 | 1985-06-13 | 1985-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-12 | 1989-06-13 | 1989-12-13 | $7700.00 | Window Closed / Lapsed |