US4435387A
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Poly-cation salts of bis (or tris) 4-O-polyhexose-thio-arylene sulfate derivatives
Assignee: Wyeth Holdings LLC
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Filing: 1982-10-25
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Granted: 1984-03-06
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Expires: 2002-10-25
Abstract
Abstract Poly-cation salts of bis (or tris) 4-O-polyhexose-thio-arylene sulfate derivatives, useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and end products.
Inventors
- 👤 Robert E. Schaub
- 👤 Janis Upeslacis
- 👤 Seymour Bernstein
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 17:56
CPC Classifications
C; C07; C07H; C07H11/00
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
106 words
A compound selected from those of the formula: ##STR5## wherein X is --SO 3 M and M is a nontoxic pharmaceutically acceptable cation salt, wherein the salt forming moiety is selected from the group consisting of alkali metal, alkaline earth metal, aluminum, ammonia, zinc and substituted ammonia selected from the group consisting of trialkylamine (C 1 -C 6 ), piperidine, pyrazine, alkanolamine (C 2 -C 6 ) and cycloalkylamine (C 3 -C 6 ); B is selected from the group consisting of --NHCO-- and --NHSO 2 --; n is an integer 2 or 3; and Z is an arylene selected from the group consisting of: ##STR6##
Claim 2
Dependent Claim
106 words
A compound selected from those of the formula: ##STR5## wherein X is --SO 3 M and M is a nontoxic pharmaceutically acceptable cation salt, wherein the salt forming moiety is selected from the group consisting of alkali metal, alkaline earth metal, aluminum, ammonia, zinc and substituted ammonia selected from the group consisting of trialkylamine (C 1 -C 6 ), piperidine, pyrazine, alkanolamine (C 2 -C 6 ) and cycloalkylamine (C 3 -C 6 ); B is selected from the group consisting of --NHCO-- and --NHSO 2 --; n is an integer 2 or 3; and Z is an arylene selected from the group consisting of: ##STR6##
Claim 3
Dependent Claim
25 words
The compound according to claim 1, heneicosatriethylammonium N,N',N"-tris[4-[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide, where the structure is: ##STR7## wherein A is N + H(C 2 H 5 ) 3 .
Claim 4
Dependent Claim
25 words
The compound according to claim 1, heneicosatriethylammonium N,N',N"-tris[4-[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benezenetrisulfonamide, where the structure is: ##STR8## wherein A is N + H(C 2 H 5 ) 3 .
Claim 5
Dependent Claim
25 words
The compound according to claim 1, heneicosatriethylammonium N,N',N"-tris[4-[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-β-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide, where the structure is: ##STR9## wherein A is N + H(C 2 H 5 ) 3 .
Claim 6
Dependent Claim
25 words
The compound according to claim 1, tetradecatriethylammonium N,N'-bis[4-[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glycopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,4-benzenedicarboxamide, where the structure is: ##STR10## wherein A is N + H(C 2 H 5 ) 3 .
Claim 7
Dependent Claim
13 words
The compound according to claim 1, heneicosasodium N,N',N"-tris[4-[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide, where the structure is: ##STR11##
Claim 8
Dependent Claim
13 words
The compound according to claim 1, heneicosasodium N,N',N"-tris[4-[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide, where the structure is: ##STR12##
Claim 9
Dependent Claim
13 words
the compound according to claim 1, heneicosasodium N,N',N"-tris[4-[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-β-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide, where the structure is: ##STR13##
Claim 10
Dependent Claim
13 words
The compound according to claim 1, tetradecasodium N,N'-bis[4-[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,4-benzenedicarboxamide, where the structure is: ##STR14##
Claim 11
Dependent Claim
55 words
A compound selected from those of the formula: ##STR15## wherein Y is selected from the group consisting of H and --COCH 3 ; B is selected from the group consisting of --NHCO-- and --NHSO 2 --; n is an integer 2 or 3; and Z is an arylene selected from the group consisting of: ##STR16##
Claim 12
Dependent Claim
55 words
A compound selected from those of the formula: ##STR15## wherein Y is selected from the group consisting of H and --COCH 3 ; B is selected from the group consisting of --NHCO-- and --NHSO 2 --; n is an integer 2 or 3; and Z is an arylene selected from the group consisting of: ##STR16##
Claim 13
Dependent Claim
18 words
The compound according to claim 10, N,N',N"-tris[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide, where the structure is: ##STR17## wherein Y is COCH 3 .
Claim 14
Dependent Claim
12 words
The compound according to claim 10, N,N',N"-tris[4-[[4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide, where the structure is: ##STR18##
Claim 15
Dependent Claim
18 words
The compound according to claim 10, N,N',N"-tris[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide, where the structure is: ##STR19## wherein Y is COCH 3 .
Claim 16
Dependent Claim
12 words
The compound according to claim 10, N,N',N"-tris[4-[[4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide, where the structure is: ##STR20##
Claim 17
Dependent Claim
18 words
The compound according to claim 10, N,N',N"-tris[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide, where the structure is: ##STR21## wherein Y is COCH 3 .
Claim 18
Dependent Claim
12 words
The compound according to claim 10, N,N',N"-tris[4-[[4-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide, where the structure is: ##STR22##
Claim 19
Dependent Claim
18 words
The compound according to claim 10, N,N'-bis[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,4-benzenedicarboxamide, where the structure is: ##STR23## wherein Y is COCH 3 .
Claim 20
Dependent Claim
12 words
The compound according to claim 10, N,N'-bis[4-[[4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,4-benzenedicarboxamide, where the structure is: ##STR24##
Claim 21
Independent Claim
135 words
A method of modulating the complement system in a body fluid which comprises subjecting said body fluid to the action of an effective complement modulating amount of a pharmaceutically acceptable compound selected from those of the formula: ##STR25## wherein X is --SO 3 M and M is a nontoxic pharmaceutically acceptable cation salt, wherein the salt forming moiety is selected from the group consisting of alkali metal, alkaline earth metal, aluminum, ammonia, zinc and substituted ammonia selected from the group consisting of trialkylamine (C 1 -C 6 ), piperidine, pyrazine, alkanolamine (C 2 -C 6 ) and cycloalkylamine (C 3 -C 6 ); B is selected from the group consisting of --NHCO-- and --NHSO 2 --; n is an integer 2 or 3; and Z is an arylene selected from the group consisting of: ##STR26##
Claim 22
Independent Claim
135 words
A method of modulating the complement system in a body fluid which comprises subjecting said body fluid to the action of an effective complement modulating amount of a pharmaceutically acceptable compound selected from those of the formula: ##STR25## wherein X is --SO 3 M and M is a nontoxic pharmaceutically acceptable cation salt, wherein the salt forming moiety is selected from the group consisting of alkali metal, alkaline earth metal, aluminum, ammonia, zinc and substituted ammonia selected from the group consisting of trialkylamine (C 1 -C 6 ), piperidine, pyrazine, alkanolamine (C 2 -C 6 ) and cycloalkylamine (C 3 -C 6 ); B is selected from the group consisting of --NHCO-- and --NHSO 2 --; n is an integer 2 or 3; and Z is an arylene selected from the group consisting of: ##STR26##
Claim 23
Dependent Claim
13 words
The method according to claim 19, wherein the body fluid is blood serum.
Claim 24
Dependent Claim
12 words
The method according to claim 19, wherein the compound is heneicosatriethylammonium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide.
Claim 25
Dependent Claim
12 words
The method according to claim 19, wherein the compound is heneicosatriethylammonium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide.
Claim 26
Dependent Claim
12 words
The method according to claim 19, wherein the compound is heneicosatriethylammonium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-β-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide.
Claim 27
Dependent Claim
12 words
The method according to claim 19, wherein the compound is tetradecatriethylammonium N,N'-bis[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,4-benzenedicarboxamide.
Claim 28
Dependent Claim
12 words
The method according to claim 19, wherein the compound is heneicosasodium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide.
Claim 29
Dependent Claim
12 words
The method according to claim 19, wherein the compound is heneicosasodium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide.
Claim 30
Dependent Claim
12 words
The method according to claim 19, wherein the compound is heneicosasodium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-β-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide.
Claim 31
Dependent Claim
12 words
The method according to claim 19, wherein the compound is tetradecasodium N,N'-bis[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,4-benzenedicarboxamide.
Claim 32
Independent Claim
132 words
A method of modulating the complement system in a warm-blooded animal which comprises administering to said warm-blooded animal an effective complement modulating amount of a pharmaceutically acceptable compound selected from those of the formula: ##STR27## wherein X is --SO 3 M and M is a nontoxic pharmaceutically acceptable cation salt, wherein the salt forming moiety is selected from the group consisting of alkali metal, alkaline earth metal, aluminum, ammonia, zinc and substituted ammonia selected from the group consisting of trialkylamine (C 1 -C 6 ), piperidine, pyrazine, alkanolamine (C 2 -C 6 ) and cycloalkylamine (C 3 -C 6 ); B is selected from the group consisting of --NHCO-- and --NHSO 2 --; n is an integer 2 or 3; and Z is an arylene selected from the group consisting of: ##STR28##
Claim 33
Independent Claim
132 words
A method of modulating the complement system in a warm-blooded animal which comprises administering to said warm-blooded animal an effective complement modulating amount of a pharmaceutically acceptable compound selected from those of the formula: ##STR27## wherein X is --SO 3 M and M is a nontoxic pharmaceutically acceptable cation salt, wherein the salt forming moiety is selected from the group consisting of alkali metal, alkaline earth metal, aluminum, ammonia, zinc and substituted ammonia selected from the group consisting of trialkylamine (C 1 -C 6 ), piperidine, pyrazine, alkanolamine (C 2 -C 6 ) and cycloalkylamine (C 3 -C 6 ); B is selected from the group consisting of --NHCO-- and --NHSO 2 --; n is an integer 2 or 3; and Z is an arylene selected from the group consisting of: ##STR28##
Claim 34
Dependent Claim
12 words
The method according to claim 29, wherein the compound is heneicosatriethylammonium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide.
Claim 35
Dependent Claim
12 words
The method according to claim 29, wherein the compound is heneicosatriethylammonium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide.
Claim 36
Dependent Claim
12 words
The method according to claim 29, wherein the compound is heneicosatriethylammonium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-β-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide.
Claim 37
Dependent Claim
12 words
The method according to claim 29, wherein the compound is tetradecatriethylammonium N,N'-bis[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,4-benzenedicarboxamide.
Claim 38
Dependent Claim
12 words
The method according to claim 29, wherein the compound is heneicosasodium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide.
Claim 39
Dependent Claim
12 words
The method according to claim 29, wherein the compound is heneicosasodium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide.
Claim 40
Dependent Claim
12 words
The method according to claim 29, wherein the compound is heneicosasodium N,N',N"-tris[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-β-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetrisulfonamide.
Claim 41
Dependent Claim
12 words
The method according to claim 29, wherein the compound is tetradecasodium N,N'-bis[4[[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]thio]phenyl]-1,4-benzenedicarboxamide.
Claim 42
Dependent Claim
12 words
The method according to claim 29, wherein the compound is administered internally.
Claim 43
Dependent Claim
12 words
The method according to claim 29, wherein the compound is administered topically.
Claim 44
Dependent Claim
16 words
The method according to claim 29, wherein the compound is administered periodontally in the oral cavity.
Claim 45
Dependent Claim
12 words
The method according to claim 29, wherein the compound is administered intra-articularly.
Claim 46
Dependent Claim
12 words
The method according to claim 29, wherein the compound is administered parenterally.
References Cited (Backward Citations)
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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) | 1987-03-06 | 1987-09-05 | 1988-03-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-06 | 1991-09-05 | 1992-03-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-06 | 1995-09-05 | 1996-03-06 | $7700.00 | Window Closed / Lapsed |