Mono-, di- and tri-adamantylcarbonyl- digalactopyranosyl- glucopyranosyl- fructofuranose sulfate salts
AssigneeAmerican Cyanamid Company
InventorsVijay G. Nair, Seymour Bernstein
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Abstract
Mono-, di- and tri-adamantylcarbonyl- digalactopyranosyl- glucopyranosyl- fructofuranose sulfate salts, useful as complement inhibitors and the process of making such compounds.
Claims21
A compound selected from those of the formula:
- ##STR3## wherein R is 1-adamantylcarbonyl;
- R' is selected from the group consisting of --SO.sub.3 A and 1-adamantylcarbonyl;
- and A is a pharmaceutically acceptable salt cation, wherein the salt forming moiety is selected from the group consisting of alkali metal, alkaline earth metal, ammonia and substituted ammonia selected from the group consisting of trialkylamine (C.sub.1 -C.sub.6), piperidine, pyrazine, alkanolamine (C.sub.2 -C.sub.6) and cycloalkylamine (C.sub.3 -C.sub.6).
The compound according to claim 1, 6-O-(1-adamantylcarbonyl)-.beta.-D-fructofuranosyl-O-.alpha.-D-galactopyra nosyl(1.fwdarw.6)-O-.alpha.-D-galactopyranosyl(1.fwdarw.6)-.alpha.-D-glucop yranoside, tridecakis(H-sulfate), tridecasalt with trimethylamine.
The compound according to claim 1, 6-O-(1-adamantylcarbonyl)-.beta.-D-fructofuranosyl-O-.alpha.-D-galactopyra nosyl(1.fwdarw.6)-O-.alpha.-D-galactopyranosyl(1.fwdarw.6)-.alpha.-D-glucop yranoside, tridecakis(H-sulfate), tridecasodium salt.
The compound according to claim 1, 6,6"'-di-1-adamantanecarboxylate-O-.alpha.-D-galactopyranosyl(1.fwdarw.6)- O-.alpha.-D-galactopyranosyl(1.fwdarw.6)-O-.alpha.-D-glucopyranosyl-.beta.- D-fructofuranose, dodecakis(H-sulfate), dodecasalt with trimethylamine.
The compound according to claim 1, 6,6"'-di-1-adamantanecarboxylate-O-.alpha.-D-galactopyranosyl(1.fwdarw.6)- O-.alpha.-D-galactopyranosyl(1.fwdarw.6)-O-.alpha.-D-glucopyranosyl-.beta.- D-fructofuranose, dodecakis(H-sulfate), dodecasodium salt.
The compound according to claim 1, 1,6-bis-O-(1-adamantylcarbonyl)-.beta.-D-fructofuranosyl-6-O-1-adamantylca rbonyl-O-.alpha.-galactopyranosyl(1.fwdarw.6)-O-.alpha.-D-galactopyranosyl( 1.fwdarw.6)-.alpha.-D-glucopyranoside, undecakis(H-sulfate), undecasalt with trimethylamine.
A process for the preparation of a compound of the formula:
- ##STR4## wherein R is 1-adamantylcarbonyl;
- R' is selected from the group consisting of --SO.sub.3 A and 1-adamantylcarbonyl;
- and A is a pharmaceutically acceptable salt cation, wherein the salt forming moiety is selected from the group consisting of alkali metal, alkaline earth metal, ammonia and substituted ammonia selected from the group consisting of trialkylamine (C.sub.1 -C.sub.6), piperidine, pyrazine, alkanolamine (C.sub.2 -C.sub.6) and cycloalkylamine (C.sub.3 -C.sub.6), which comprises treating anhydrous stachyose with trityl chloride in pyridine in the presence of anhydrous calcium sulfate under refrigeration for 2 days, then acetylating at room temperature with acetic anhydride for 24 hours to give mono-, di- or tritrityl peracetyl stachyose;
- treating with 70% acetic acid at 65.degree.-70.degree. C. for 3 hours, hydrolysing all trityl groups to --OH;
- treating with 1-adamantane carboxylic acid chloride in pyridine under refrigeration, reacting with methanol saturated with ammonia;
- treating with a trialkylamine-sulfur trioxide complex (C.sub.1 -C.sub.6) and treating with an alkali metal or alkaline earth metal cation-containing compound or ammonia or substituted ammonia selected from the group consisting of piperidine, pyrazine, alkanolamine (C.sub.2 -C.sub.6) and cycloalkylamine (C.sub.3 -C.sub.6).
Dependencies are inferred from the claim text.