6-Substituted purine nucleotides

Claim 2

A COMPOUND SELECTED FROM THE GROUP CONSISTING OF A COMPOUND OF THE STRUCTURE:

Claim 3

The compound of claim 1 in which X is N, Y is C-NH-OR2, and R is OH.

Claim 4

The compound of claim 2 in wHich R2 is H.

Claim 5

The compound of claim 2 in which R2 is CH3.

Claim 6

The compound of claim 2 in which R2 is C2H5.

Claim 7

6-Hydroxylamino-9- Beta -D-ribofuranosylpurine 3'',5''-cyclic phosphate.

Claim 8

6-Hydroxylamino-9- Beta -D-ribofuranosylpurine 3'',5''-cyclic phosphate.

Claim 9

6-Methoxyamino-9- Beta -D-ribofuranosylpurine 3'',5''-cyclic phosphate.

Claim 10

6-Methoxyamino-9- Beta -D-ribofuranosylpurine 3'',5''-cyclic phosphate.

Claim 11

6-Ethoxyamino-9- Beta -D-ribofuranosylpurine 3'',5''-cyclic phosphate.

Claim 12

6-Ethoxyamino-9- Beta -D-ribofuranosylpurine 3'',5''-cyclic phosphate.

Claim 13

A process of synthesizing 6-substituted purine nucleotides comprising alkylating the N1 oxide function of adenosine 3'',5''-cyclic phosphate 1-N-oxide with a compound selected from the group consisting of C1 to C8 alkyl or C7 to C10 aralkyl to provide the corresponding O-alkylated adenosine 3'',5''-cyclic phosphate 1-N-oxide, subjecting said O-alkylated adenosine 3'',5''-cyclic phosphate 1-N-oxide to base catalyzed rearrangement at pH greater than 7 to afford N6-alkoxy adenosine 3'',5''-cyclic phosphate, and reacting said N6 -alkoxy compound with hydrogen sulfide causing it to undergo nucleophillic displacement to yeild the corresponding 6-thione substituted compound.

Claim 14

A process of synthesizing 6-substituted purine nucleotides comprising alkylating the N1 oxide function of adenosine 3'',5''-cyclic phosphate 1-N-oxide with a compound selected from the group consisting of C1 to C8 alkyl or C7 to C10 aralkyl to provide the corresponding O-alkylated adenosine 3'',5''-cyclic phosphate 1-N-oxide, subjecting said O-alkylated adenosine 3'',5''-cyclic phosphate 1-N-oxide to base catalyzed rearrangement at pH greater than 7 to afford N6-alkoxy adenosine 3'',5''-cyclic phosphate, and reacting said N6 -alkoxy compound with hydrogen sulfide causing it to undergo nucleophillic displacement to yeild the corresponding 6-thione substituted compound.

Claim 15

A process of synthesizing 6-substituted purine nucleotides comprising subjecting adenosine 3'',5''-cyclic phosphate-1-N-oxide to base catalyzed rearrangement at pH greater than 7 to afford 6-hydroxylamino-9- Beta -D-ribofuranoxylpurine 3'',5''-cyclic phosphate, and thereafter causing said 6-hydroxylamino derivative to undergo nucleophillic displacement by reacting itt with hydrogen sulfide to yield the corresponding 6-thione substituted compound.

Claim 16

A process of synthesizing 6-substituted purine nucleotides comprising subjecting adenosine 3'',5''-cyclic phosphate-1-N-oxide to base catalyzed rearrangement at pH greater than 7 to afford 6-hydroxylamino-9- Beta -D-ribofuranoxylpurine 3'',5''-cyclic phosphate, and thereafter causing said 6-hydroxylamino derivative to undergo nucleophillic displacement by reacting itt with hydrogen sulfide to yield the corresponding 6-thione substituted compound.

Claim 17

The process of claim 9 in which said 6-thione substituted compound is thereafter alkylated to afford 6-alkylthio-9- Beta -D-ribofuranosylpurine 3'',5''-cyclic phosphate, wherein the alkyl group is from C1 to C6.

Claim 18

The process of claim 9 in which said base catalyzed rearrangement is carried out in a refluxing solution having a pH of between about 7.0 and 9.0.

Claim 19

The process of claim 10 in which said base catalyzed rearrangement is carried out in a solution having a pH of at least 10.

Claim 20

The process of claim 9 in which said nucleophillic displacement is carried out in a closed container in the presence of an aqueous solution of pyridine containing a molar excess of hydrogen sulfide with respect to said pyridine.

Claim 21

A process of synthesizing 6-substituted purine nucleotides comprising alkylating adenosine 3'',5''-cyclic phosphate 1-N-oxide with a compound selected from the group consisting of C1 to C8 alkyl or C7 to C10 aralkyl to provide the corresponding O-alkylated adenosine 3'',5''-cyclic phosphate 1-N-oxide, subjecting said O-alkylated adenosine 3'',5''-cyclic phosphate 1-N-oxide to a refluxing solution having a pH of between about 7.0 and 9.0 at a temperature between 0* and 100*C to cause base catalyzed rearrangement and to afford N6-alkoxy adenosine 3'',5''-cyclic phosphate, and reacting said N6-alkoxy compound in a closed container in the presence of an aqueous solution of pyridine containing a molar excess of hydrogen sulfide with respect to said pyridine to cause said N6 -alkoxy compound to undergo nucleophillic displacement to yield the corresponding 6-thione substituted compound.

Claim 22

A process of synthesizing 6-substituted purine nucleotides comprising alkylating adenosine 3'',5''-cyclic phosphate 1-N-oxide with a compound selected from the group consisting of C1 to C8 alkyl or C7 to C10 aralkyl to provide the corresponding O-alkylated adenosine 3'',5''-cyclic phosphate 1-N-oxide, subjecting said O-alkylated adenosine 3'',5''-cyclic phosphate 1-N-oxide to a refluxing solution having a pH of between about 7.0 and 9.0 at a temperature between 0* and 100*C to cause base catalyzed rearrangement and to afford N6-alkoxy adenosine 3'',5''-cyclic phosphate, and reacting said N6-alkoxy compound in a closed container in the presence of an aqueous solution of pyridine containing a molar excess of hydrogen sulfide with respect to said pyridine to cause said N6 -alkoxy compound to undergo nucleophillic displacement to yield the corresponding 6-thione substituted compound.