EP0184473A1
Expired / Lapsed
EP
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Regioselective synthesis of 9-substituted purine acyclonucleoside derivatives
Assignee: Merck and Co Inc
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Filing: 1985-10-21
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Granted: —
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Expires: 2005-10-21
Abstract
Abstract A process for preparing 9-substituted guanine- containing acyclonucleosides comprising selective alkylation at the 9-position of the purine by utilizing a blocking group at the 6-position.
Inventors
- 👤 Malcolm Maccoss
- 👤 Richard L. Tolman
- 👤 Arthur F. Wagner
- 👤 John Hannah
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 14:08
CPC Classifications
C; C07; C07D; C07D473/00; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C07F9/65616; C07F9/6564; C07F9/6571; C07F9/6574; C07F9/65742
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
31 words
A process for preparing 9-substituted guanine-related acyclonucleosides comprising alkylation of a pro-guanine derivative having a blocking group at the 6-position of the purine and optionally at the 2-position of the purine.
Claim 2
Dependent Claim
31 words
A process for preparing 9-substituted guanine-related acyclonucleosides comprising alkylation of a pro-guanine derivative having a blocking group at the 6-position of the purine and optionally at the 2-position of the purine.
Claim 3
Dependent Claim
13 words
A process according to Claim 1, wherein the blocking group is thereafter removed.
Claim 4
Dependent Claim
14 words
A process according to Claim 2, wherein the blocking group is removed by hydrogenolysis.
Claim 5
Dependent Claim
16 words
A process according to Claim 2, wherein the blocking group is removed by treatment with acid.
Claim 6
Dependent Claim
16 words
A process according to Claim 2, wherein the blocking group is removed by treatment with base.
Claim 7
Dependent Claim
22 words
A process according to Claim 2, wherein the blocking group is removed by nucleophilic displacement, followed by hydrolysis or 8-elimination using base.
Claim 8
Dependent Claim
74 words
A process according to Claim 1, wherein the blocking group is selected from 6-benzyloxy, substituted 6-benzyloxy, 6-phenoxy, substituted 6-phenoxy, 6-(2-phenylethoxy), substituted 6-(2-phenylethoxy), arylsulfonyloxy, substituted arylsulfonyloxy, 6-(aryl-siloxy), 6-alkyl-siloxy), and 6-β cyanoethoxy, wherein the aforementioned aryl groups are selected from phenyl naphthyl, substituted phenyl and substituted naphthyl and the substituents on the aforementioned substituted 6-benzyloxy, 6-phenoxy, 6-(2-phenylethoxy), arylsulfonyloxy, phenyl and naphthyl groups are selected from C l to C 6 alkyl, halo, nitro, phenyl and trifluoromethyl.
Claim 9
Dependent Claim
87 words
A process for preparing cyclic phosphates of 2,6-substituted purines comprising alkylating a purine having a blocking group at the 6-position with a compound of the formula: wherein R 1 is alkyl of 1 to 18 carbons, haloalkyl of 1 to 18 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, wherein halo means fluorine, chlorine, bromine or iodine and the substituents on the phenyl group or the phenyl moiety of the benzyl group are selected from alkyl, nitro and halogen; and X is a suitable leaving group.
Claim 10
Dependent Claim
87 words
A process for preparing cyclic phosphates of 2,6-substituted purines comprising alkylating a purine having a blocking group at the 6-position with a compound of the formula: wherein R 1 is alkyl of 1 to 18 carbons, haloalkyl of 1 to 18 carbon atoms, benzyl, substituted benzyl, phenyl or substituted phenyl, wherein halo means fluorine, chlorine, bromine or iodine and the substituents on the phenyl group or the phenyl moiety of the benzyl group are selected from alkyl, nitro and halogen; and X is a suitable leaving group.
Claim 11
Dependent Claim
17 words
A process according to Claim 8, wherein X is halide or tosyloxy and R 1 is O-chlorophenyl.
Claim 12
Dependent Claim
20 words
A process according to Claim 8, wherein the pro-guanine derivative is selected from 2-amino-6-benzyloxypurine, 2-amino-f6-(o-nitrophenoxy)purine, 2-chloro-6-benzyloxypurine, 2-amino-6-chloropurine and 2, 6-dichloropurine.
Claim 13
Dependent Claim
22 words
A process according to Claim 1, wherein the pro-guanine derivative is selected from 2-amino-6-benzyloxypurine, 2-chloro-6-benzyloxypurine, 2-amino-6-(o-nitrophenoxy)purine, 2-amino-6-β-cyanoethoxy -purine, 2-amino-6-chloropurine and 2, 6-dichloropurine.
Claim 14
Dependent Claim
59 words
A process for preparing a compound of the formula wherein R 2 is benzyloxy or o-nitrophenoxy; and R is amino or chloro; comprising alkylating a compound of the formula: wherein R 2 and R 3 are as defined above with a compound o the formula: wherein R 1 is as defined above and X is a suitable leaving group.
Claim 15
Dependent Claim
59 words
A process for preparing a compound of the formula wherein R 2 is benzyloxy or o-nitrophenoxy; and R is amino or chloro; comprising alkylating a compound of the formula: wherein R 2 and R 3 are as defined above with a compound o the formula: wherein R 1 is as defined above and X is a suitable leaving group.
Claim 16
Dependent Claim
12 words
A process according to Claim 12, wherein X is halide or tosyloxy.
Claim 17
Dependent Claim
10 words
A process according to Claim 13, wherein X is chloride.
References Cited (Backward Citations)
EP0074306A2
Cited
FR2541681A1
Cited
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