US5136030A
Expired / Lapsed
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Immunostimulating guanine derivatives, compositions and methods
Assignee: Scripps Research Institute
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Filing: 1991-04-29
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Granted: 1992-08-04
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Expires: 2011-04-29
Abstract
Abstract 7,8-Disubstituted quanosine nucleoside derivatives are found to be potent immune response enhancing agents in human and animal cells. 7-Substituents are hydrocarbyl radicals having a length greater than ethyl and less than about decyl. 8-Substituents are ═O, ═S, ═Se and ═NCN. Compositions and methods of use are also disclosed.
Inventors
- 👤 Robert Chen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 03:13
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/16; A; A61; A61K; A61K39/00; A61K39/39; A61K2039/555; A61K2039/55511; A61K2039/55561
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
138 words
A process of preparing a purine derivative comprising the steps of: (a) providing a purine starting material substituted at the 8-position by an --X--CH 2 CR═CH 2 radical wherein X is selected from the group consisting of S, O, and Se, and R is hydrogen, lower alkyl and benzyl, said purine starting material further including a blocking group bonded at the 9-position nitrogen atom; (b) heating said purine starting material to an elevated temperature of about 50° C. to about 200° C.; and (c) maintaining said elevated temperature for a period of time sufficient to form a rearranged purine product substituted (i) at the 8-position by the group ═X, wherein X in said product is the same as the X in the purine starting material, and (ii) at the 7-position by a group --CH 2 --CR═CH 2 .
Claim 2
Dependent Claim
138 words
A process of preparing a purine derivative comprising the steps of: (a) providing a purine starting material substituted at the 8-position by an --X--CH 2 CR═CH 2 radical wherein X is selected from the group consisting of S, O, and Se, and R is hydrogen, lower alkyl and benzyl, said purine starting material further including a blocking group bonded at the 9-position nitrogen atom; (b) heating said purine starting material to an elevated temperature of about 50° C. to about 200° C.; and (c) maintaining said elevated temperature for a period of time sufficient to form a rearranged purine product substituted (i) at the 8-position by the group ═X, wherein X in said product is the same as the X in the purine starting material, and (ii) at the 7-position by a group --CH 2 --CR═CH 2 .
Claim 3
Dependent Claim
15 words
The process of claim 1 including the further step of isolating said product purine molecule.
Claim 4
Dependent Claim
20 words
The process of claim 1 wherein said purine starting material is dissolved or dispersed in an inert liquid solvent medium.
Claim 5
Dependent Claim
36 words
The process of claim 3 wherein said inert liquid solvent medium includes a catalytic amount of PdCl 2 , and said purine starting material is heated to a temperature of about 50° to about 100° C.
Claim 6
Dependent Claim
23 words
The process of claim 2 wherein the 9-position nitrogen atom is bonded 9-1'-beta to a ribosyl or deoxyribosyl radical as said blocking group.
Claim 7
Dependent Claim
21 words
The process of claim 5 wherein said purine starting material is selected from the group consisting of adenosine, guanosine and inosine.
Claim 8
Dependent Claim
12 words
The process of claim 6 wherein said purine starting material is 8-(2-propenyl)oxyguanosine.
Claim 9
Dependent Claim
38 words
A process for forming 7-allyl-8-oxoguanosine that comprises the step of heating 8-(2-propenyl)oxyguanosine in an inert liquid solvent medium at a temperature of about 50° C. to about 200° C. for a period of time sufficient to form 7-allyl-8-oxoguanosine.
Claim 10
Dependent Claim
38 words
A process for forming 7-allyl-8-oxoguanosine that comprises the step of heating 8-(2-propenyl)oxyguanosine in an inert liquid solvent medium at a temperature of about 50° C. to about 200° C. for a period of time sufficient to form 7-allyl-8-oxoguanosine.
Claim 11
Dependent Claim
24 words
The process of claim 8 wherein said inert liquid solvent medium is selected from the group consisting of water, dimethylformamide, tetrahydrofuran and dimethyl sulfoxide.
Claim 12
Dependent Claim
28 words
The process of claim 8 wherein said inert liquid medium is water, said temperature is the reflux temperature of the medium, and said time period is three hours.
Claim 13
Dependent Claim
13 words
The process of claim 8 including the further step of isolating said 7-allyl-8-oxoguanosine.
References Cited (Backward Citations)
No citation records indexed.
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