US4369178A
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Glucosamine peptide derivatives, their production and use
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1980-02-21
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Granted: 1983-01-18
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Expires: 2000-02-21
Abstract
Abstract Novel glucosamine-peptide derivatives of the formula: ##STR1## wherein m is 0 or 1; n is 0 or an integer of 1 to 9; R is lower alkyl which may be substituted with hydroxyl, or aryl; R 1 is hydrogen or acyl having an acyclic hydrocarbon group, the terminal of which may be substituted with a cyclic hydrocarbon group directly, via a carbonyl group or via an oxygen atom; provided that when R 1 is hydrogen m is 1; R 2 is hydrogen or lower alkyl which may form a ring by connecting its terminal with the α-nitrogen atom when n is 0, or hydrogen when n is an integer of 1 to 9; R 3 is hydrogen or lower alkyl; R 4 and R 5 are each hydrogen or lower alkyl which may be substituted with hydroxyl or benzyloxyl; R 6 is hydrogen or lower alkyl; R 7 is alkyl which may be substituted with lower alkoxyl or aralkyl; R 8 and R 9 are each hydrogen, lower alkyl or aralkyl; and (D) and (L) each indicate configurations if their respective carbon atoms are asymmetric; or an acid addition salt thereof, have immunostimulatory activity.
Inventors
- 👤 Yuichi Yamamura
- 👤 Ichiro Azuma
- 👤 Shigeru Kobayashi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 21:38
CPC Classifications
C; C07; C07K; C07K9/00; C07K9/001; C07K9/005; A; A61; A61P; A61P35/00; A61P37/00; A61P37/02; A61P37/04
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
180 words
A compound of the formula: ##STR11## wherein A is a C 2-10 acylic hydrocarbon group, the terminal of which is substituted with an unsaturated 6-membered cyclic hydrocarbon group; m is 0 or 1; n is 0 or an integer of 1 to 9; R is C 1-4 alkyl which may be substituted with hydroxyl, or phenyl; R 2 is hydrogen or C 1-4 alkyl which may form a ring by connecting its terminal with the α-nitrogen atom, when n is 0, or hydrogen when n is an integer of 1 to 9; R 3 is hydrogen or C 1-4 alkyl; R 4 and R 5 are each hydrogen or C 1-4 alkyl which may be substituted with hydroxyl or benzyloxyl; R 6 is hydrogen or C 1-4 alkyl; R 7 is C 1-18 alkyl which may be substituted with C 1-3 alkoxyl; R 8 and R 9 are each hydrogen, C 1-4 alkyl or C 1-2 alkyl substituted with phenyl; and (D) and (L) each indicate configuration if their respective carbon atoms are asymmetric; or an acid addition salt thereof.
Claim 2
Dependent Claim
180 words
A compound of the formula: ##STR11## wherein A is a C 2-10 acylic hydrocarbon group, the terminal of which is substituted with an unsaturated 6-membered cyclic hydrocarbon group; m is 0 or 1; n is 0 or an integer of 1 to 9; R is C 1-4 alkyl which may be substituted with hydroxyl, or phenyl; R 2 is hydrogen or C 1-4 alkyl which may form a ring by connecting its terminal with the α-nitrogen atom, when n is 0, or hydrogen when n is an integer of 1 to 9; R 3 is hydrogen or C 1-4 alkyl; R 4 and R 5 are each hydrogen or C 1-4 alkyl which may be substituted with hydroxyl or benzyloxyl; R 6 is hydrogen or C 1-4 alkyl; R 7 is C 1-18 alkyl which may be substituted with C 1-3 alkoxyl; R 8 and R 9 are each hydrogen, C 1-4 alkyl or C 1-2 alkyl substituted with phenyl; and (D) and (L) each indicate configuration if their respective carbon atoms are asymmetric; or an acid addition salt thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1, wherein m is 0.
Claim 4
Dependent Claim
14 words
A compound according to claim 1, wherein m is 1 and n is 0.
Claim 5
Dependent Claim
13 words
A compound according to claim 1, wherein R 7 is C 1-4 alkyl.
Claim 6
Dependent Claim
44 words
A compound of the formula: ##STR12## wherein l is an integer of 0 to 7; R* is C 1-4 alkyl; R 5* is C 1-4 alkyl which may be substituted with hydroxyl; R 7* is C 1-4 alkyl; or an acid addition salt thereof.
Claim 7
Dependent Claim
44 words
A compound of the formula: ##STR12## wherein l is an integer of 0 to 7; R* is C 1-4 alkyl; R 5* is C 1-4 alkyl which may be substituted with hydroxyl; R 7* is C 1-4 alkyl; or an acid addition salt thereof.
Claim 8
Dependent Claim
15 words
A compound according to claim 1, wherein R 8 and R 9 are each hydrogen.
Claim 9
Dependent Claim
11 words
A compound according to claim 1, said compound being methyl 2-[2-acetamido-2-deoxy-6-O-{10-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanyl}-D-glucopyranos-3-O-yl]-D-propionyl-L-valyl-D-isoglutaminate.
Claim 10
Dependent Claim
11 words
A compound according to claim 1, said compound being methyl 2-[2-acetamido-2-deoxy-6-O-{10-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoyl}-D-glucopyranos-3-O-yl]-D-propionyl-L-seryl-D-isoglutaminate.
Claim 11
Dependent Claim
11 words
A compound according to claim 1, said compound being methyl 2-[2-acetamido-2-deoxy-6-O-{10-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoyl}glycyl-D-glucopyranos-3-O-yl]-D-propionyl-L-valyl-D-isoglutaminate.
Claim 12
Independent Claim
201 words
A method for stimulating the immunological functions of a warmblooded animal which comprises administering to said animal an effective amount of a compound of the formula: ##STR13## wherein A is a C 2-10 acylic hydrocarbon group, the terminal of which is substituted with an unsaturated 6-membered cyclic hydrocarbon group; m is 0 or 1; n is 0 or an integer of 1 to 9; R is C 1-4 alkyl which may be substituted with hydroxyl, or phenyl; R 2 is hydrogen or C 1-4 alkyl which may form a ring by connecting its terminal with the α-nitrogen atom, when n is 0, or hydrogen when n is an integer of 1 to 9; R 3 is hydrogen or C 1-4 alkyl; R 4 and R 5 are each hydrogen or C 1-4 alkyl which may be substituted with hydroxyl or benzyloxyl; R 6 is hydrogen or C 1-4 alkyl; R 7 is C 1-18 alkyl which may be substituted with C 1-3 alkoxyl; R 8 and R 9 are each hydrogen, C 1-4 alkyl or C 1-2 alkyl substituted with phenyl; and (D) and (L) each indicate configurations if their respective carbon atoms are asymmetric; or an acid addition salt thereof.
Claim 13
Independent Claim
201 words
A method for stimulating the immunological functions of a warmblooded animal which comprises administering to said animal an effective amount of a compound of the formula: ##STR13## wherein A is a C 2-10 acylic hydrocarbon group, the terminal of which is substituted with an unsaturated 6-membered cyclic hydrocarbon group; m is 0 or 1; n is 0 or an integer of 1 to 9; R is C 1-4 alkyl which may be substituted with hydroxyl, or phenyl; R 2 is hydrogen or C 1-4 alkyl which may form a ring by connecting its terminal with the α-nitrogen atom, when n is 0, or hydrogen when n is an integer of 1 to 9; R 3 is hydrogen or C 1-4 alkyl; R 4 and R 5 are each hydrogen or C 1-4 alkyl which may be substituted with hydroxyl or benzyloxyl; R 6 is hydrogen or C 1-4 alkyl; R 7 is C 1-18 alkyl which may be substituted with C 1-3 alkoxyl; R 8 and R 9 are each hydrogen, C 1-4 alkyl or C 1-2 alkyl substituted with phenyl; and (D) and (L) each indicate configurations if their respective carbon atoms are asymmetric; or an acid addition salt thereof.
Claim 14
Dependent Claim
12 words
A compound defined as in claim 1, but wherein A-CO is 10-(2,3-dimethoxy-5-methyl-1,4-benzoquinn-6-yl)decanoyl.
References Cited (Backward Citations)
US4101536A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1986-01-17 | 1986-07-19 | 1987-01-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-01-17 | 1990-07-19 | 1991-01-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-01-17 | 1994-07-19 | 1995-01-18 | $7700.00 | Window Closed / Lapsed |