N-2 substituted purines
First Claim
1. A method for the preparation of a compound of Formula I:
- ##STR7## wherein G is CH or N;
X is NH2 or OH;
Y is RQ or NHRQ, wherein said R is a hydrocarbyl group having from 2 to about 20 carbon atoms; and
Q is H, NH2, polyalkylamino, hydrazines, hydroxylamines, semicarbazides, thiosemicarbazides, hydrazones, hydrazides, imidazoles, imidazole amides, alkylimidazoles, tetrazole, triazole, pyrrolidine, piperidine, piperazine, morpholine, thiols, aldehydes, ketones, alcohols, alkoxy groups, or halogens or alkoxy groups; and
Z is H, ribose or deoxyribose;
comprising;
providing a compound of Formula I wherein Y is halogen; and
contacting said compound with a compound of Formula RQ or NHRQ, wherein R is a hydrocarbyl group having from 2 to about 20 carbon atoms; and
Q is H, NH2, polyalkylamino, a hydrazine, a hydroxylamine, a semicarbazide, a thiosemicarbazide, a hydrazone, a hydrazide, an imidazole, an imidazole amide, an alkylimidazole, a tetrazole, a triazole, a pyrrolidine, a piperidine, a piperazine, a morpholine, a thiol, an aldehyde, a ketone, an alcohol, or an alkoxy group;
under conditions of time, temperature and pressure sufficient to form said compound of Formula I.
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Accused Products
Abstract
This invention presents novel purine-based compounds for inclusion into oligonucleotides. The compounds of the invention, when incorporated into oligonucleotides are especially useful as "antisense" agents--agents that are capable of specific hybridization with a nucleotide sequence of an RNA. Oligonucleotides are used for a variety of therapeutic and diagnostic purposes, such as treating diseases, regulating gene expression in experimental systems, assaying for RNA and for RNA products through the employment of antisense interactions with such RNA, diagnosing diseases, modulating the production of proteins, and cleaving RNA in site specific fashions. The compounds of the invention include novel heterocyclic bases, nucleosides, and nucleotides. When incorporated into oligonucleotides, the compounds of the invention can be useful for modulating the activity of RNA.
72 Citations
22 Claims
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1. A method for the preparation of a compound of Formula I:
- ##STR7## wherein G is CH or N;
X is NH2 or OH; Y is RQ or NHRQ, wherein said R is a hydrocarbyl group having from 2 to about 20 carbon atoms; and
Q is H, NH2, polyalkylamino, hydrazines, hydroxylamines, semicarbazides, thiosemicarbazides, hydrazones, hydrazides, imidazoles, imidazole amides, alkylimidazoles, tetrazole, triazole, pyrrolidine, piperidine, piperazine, morpholine, thiols, aldehydes, ketones, alcohols, alkoxy groups, or halogens or alkoxy groups; andZ is H, ribose or deoxyribose;
comprising;providing a compound of Formula I wherein Y is halogen; and contacting said compound with a compound of Formula RQ or NHRQ, wherein R is a hydrocarbyl group having from 2 to about 20 carbon atoms; and
Q is H, NH2, polyalkylamino, a hydrazine, a hydroxylamine, a semicarbazide, a thiosemicarbazide, a hydrazone, a hydrazide, an imidazole, an imidazole amide, an alkylimidazole, a tetrazole, a triazole, a pyrrolidine, a piperidine, a piperazine, a morpholine, a thiol, an aldehyde, a ketone, an alcohol, or an alkoxy group;under conditions of time, temperature and pressure sufficient to form said compound of Formula I. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 20, 21, 22)
- ##STR7## wherein G is CH or N;
-
13. The method of claim 54 wherein Q is alkane having from 5 to 20 carbon atoms.
Specification