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US4468385A
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Poly-cation salts of 4-O-poly-hexaose-thio-alkylene sulfate derivatives and method of use
Assignee: Wyeth Holdings LLC
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Filing: 1983-08-29
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Granted: 1984-08-28
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Expires: 2003-08-29
Abstract
Abstract Poly-cation salts of 4-O-polyhexaose-thio-alkylene sulfate derivatives, useful as modulators of the complement system, the intermediates thereof and the process of making such intermediates and products.
Inventors
- 👤 Francis M. Callahan
- 👤 Thomas G. Miner
- 👤 Seymour Bernstein
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 13:50
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/14
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
85 words
A compound selected from those of the formula: ##STR6## 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 ); and R 1 is selected from the group consisting of ##STR7##
Claim 2
Dependent Claim
85 words
A compound selected from those of the formula: ##STR6## 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 ); and R 1 is selected from the group consisting of ##STR7##
Claim 3
Dependent Claim
20 words
The compound according to claim 1, 2,3-dihydroxy-4-mercaptobutyl 2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside heptasodium salt, having the structure: ##STR8## where X is --SO 3 Na.
Claim 4
Dependent Claim
29 words
The compound according to claim 1, 2,3-dihydroxy-4-mercaptobutyl 2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside heptatriethylammonium salt, having the structure: ##STR9## where X is --SO 3 - NH + (C 2 H 5 ) 3 .
Claim 5
Dependent Claim
20 words
The compound according to claim 1, 3-hydroxy-2-mercaptopropyl 2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside nonasodium salt, having the structure: ##STR10## where X is --SO 3Na .
Claim 6
Dependent Claim
29 words
The compound according to claim 1, 3-hydroxy-2-mercaptopropyl 2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside nonatriethylammonium salt, having the structure: ##STR11## where X is --SO 3 - NH + (C 2 H 5 ) 3 .
Claim 7
Dependent Claim
19 words
The compound according to claim 1, S-[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]-L-cysteine heptasodium salt, having the structure: ##STR12## where X is --SO 3 Na.
Claim 8
Dependent Claim
28 words
The compound according to claim 1, S-[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]-L-cysteine heptatriethylammonium salt, having the structure: ##STR13## where X is --SO 3 - NH + (C 2 H 5 ) 3 .
Claim 9
Dependent Claim
20 words
The compound according to claim 1, S-[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]-2-acetamido-4-mercaptobutyric acid heptasodium salt, having the structure: ##STR14## where X is --SO 3 Na.
Claim 10
Dependent Claim
29 words
The compound according to claim 1, S-[2,3,6-tri-O-sulfo-4-O-(2,3,4,6-tetra-O-sulfo-α-D-glucopyranosyl)-β-D-glucopyranosyl]-2-acetamido-4-mercaptobutyric acid heptatriethylammonium salt, having the structure: ##STR15## where X is --SO 3 - NH + (C 2 H 5 ) 3 .
Claim 11
Dependent Claim
33 words
A compound selected from those of the formula: ##STR16## wherein Y is selected from the group consisting of hydrogen and --COCH 3 and R 1 is selected from the group consisting of ##STR17##
Claim 12
Dependent Claim
33 words
A compound selected from those of the formula: ##STR16## wherein Y is selected from the group consisting of hydrogen and --COCH 3 and R 1 is selected from the group consisting of ##STR17##
Claim 13
Dependent Claim
18 words
The compound according to claim 10, 2,3-dihydroxy-4-mercaptobutyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside, having the structure: ##STR18## where Y is --COCH 3 .
Claim 14
Dependent Claim
12 words
The compound according to claim 10, 2,3-dihydroxy-4-mercaptobutyl 4-O-(α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside, having the structure: ##STR19##
Claim 15
Dependent Claim
18 words
The compound according to claim 10, 3-hydroxy-2-mercaptopropyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside having the structure: ##STR20## where Y is --COCH 3 .
Claim 16
Dependent Claim
12 words
The compound according to claim 10, 3-hydroxy-2-mercaptobutyl 4-O-(α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside having the structure: ##STR21##
Claim 17
Dependent Claim
20 words
The compound according to claim 10, S-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl]-L-N-tertiary-butyloxycabonyl tert. butyl ester, having the structure: ##STR22## where Y is --COCH 3 .
Claim 18
Dependent Claim
13 words
The compound according to claim 10, 4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyl-L-N-tertiarybutyloxycarbonylcysteine, tertiary-butyl ester, having the structure: ##STR23##
Claim 19
Dependent Claim
20 words
The compound according to claim 10, S-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl]-2-acetamido-4-mercaptobutyric acid, tertiary-butyl ester, having the structure: ##STR24## where Y is --COCH 3 .
Claim 20
Dependent Claim
14 words
The compound according to claim 10, S-[4-O-(α-D-glucopyranosyl)-β-D-glucopyranosyl]-2-acetamido-4-mercaptobutyric acid, tertiary-butyl ester, having the structure: ##STR25##
Claim 21
Independent Claim
110 words
A method of modulating the complement system in a warm-blooded animal which comprises administering to said animal an effective complement modulating amount of a pharmaceutically acceptable compound selected from those of the formula: ##STR26## 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 ); and R 1 is selected from the group consisting of ##STR27##
Claim 22
Independent Claim
110 words
A method of modulating the complement system in a warm-blooded animal which comprises administering to said animal an effective complement modulating amount of a pharmaceutically acceptable compound selected from those of the formula: ##STR26## 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 ); and R 1 is selected from the group consisting of ##STR27##
References Cited (Backward Citations)
US4404365A
Cited
US4399126A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-08-28 | 1988-02-27 | 1988-08-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-08-28 | 1992-02-27 | 1992-08-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-08-28 | 1996-02-27 | 1996-08-28 | $7700.00 | Window Closed / Lapsed |