Adenosine derivatives having pharmaceutical activity as antihypertensives

Claim 2

An adenosine derivative having the formula (I): wherein R is a lower alkyl group; R′ is hydrogen or a lower alkyl group, X is cycloalkyl group, an alkyl group having at least one hydroxy group, an alkyl group having at least one phenyl group, a bicycloalkyl group, a naphthylalkyl group, an acenaphthylenylalkyl group or a group of the formula (II) or (III); Z is hydrogen, a hydroxy group or a lower alkoxy group, Q is hydrogen or a hydroxy group, A is -CH₂, -O-, -S- or represents a direct bond; Y is -(CH₂) n - or represents a direct bond; n is an integer of 1 to 3; and the broken line represents an optional bond, and pharmaceutically acceptable salts thereof.

Claim 3

An adenosine derivative as claimed in claim 1, wherein R represents a straight or branched lower alkyl group having from 1 to 6 carbon atoms.

Claim 4

An adenosine derivative as claimed in claim 1 or claim 2, wherein R represents a straight or branched lower alkyl group having from 1 to 3 carbon atoms.

Claim 5

An adenosine derivative as claimed in any one of claims 1 to 3, wherein R represents a methyl, ethyl, propyl or isopropyl group.

Claim 6

An adenosine derivative as claimed in any one of claims 1 to 4, wherein R′ represents a straight or branched chain alkyl group having from 1 to 6 carbon atoms.

Claim 7

An adenosine derivative as claimed in claim 5, wherein R′ represents a straight or branched chain alkyl group having from 1 to 3 carbon atoms.

Claim 8

An adenosine derivative as claimed in claim 6, wherein R′ represents a methyl, ethyl, propyl or isopropyl group.

Claim 9

An adenosine derivative as claimed in any one of the preceding claims, wherein X represents a cycloalkyl group having from 3 to 8 carbon atoms.

Claim 10

An adenosine derivative as claimed in claim 8, wherein X represents a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclohexyl group.

Claim 11

An adenosine derivative as claimed in any one of the preceding claims, wherein the alkyl groups or moities in the moiety X have from 1 to 4 carbon atoms.

Claim 12

An adenosine derivative as claimed in claim 10, wherein the alkyl groups or moities in the moiety X are methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, sec -butyl or tert -butyl groups.

Claim 13

An adenosine derivative as claimed in any one of the preceding claims, wherein Z represents a straight or branched alkoxy group having from 1 to 3 carbon atoms.

Claim 14

N⁶-cyclopentyl-2′-O-methyladenosine; N⁶-cyclohexyl-2′-O-methyladenosine; N⁶-(2,3-dihydroxypropyl)-2′-O-methyladenosine; N⁶-benzyl-2′-O-methyladenosine; N⁶-(2,2-diphenylethyl)-2′-O-methyladenosine; N⁶-(exo-dicyclo[2,2,1]heptyl)-2′-O-methyladenosine; N⁶-(endo-dicyclo[2,2,1]heptyl)-2′-O-methyladenosine; N⁶-(1-naphthyl)methyl-2′-O-methyladenosine; N⁶-(1-acenaphthylenyl)methyl-2′-O-methyladenosine; N⁶-(1,2-dihydro-1-acenaphthylenyl)methyl-2′-O-methyladeno­sine; N⁶-(2,3-dihydro-1H-indene-1-yl)-2′-O-methyladenosine; N⁶-(2,3-dihydro-1H-indene-2-yl)-2′-O-methyladenosine; N⁶-(2,3-dihydro-1H-indene-1-yl)methyl-2′-O-methyladenosine; N⁶-(3H-indene-1-yl)methyl-2′-O-methyladenosine; N⁶-(5-methoxy-2,3-dihydro-1H-indene-1-yl)-2′-O-methyl­adenosine; N⁶-(1-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(2-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(3,4-dihydro-1-naphthyl)methyl-2′-O-methyladenosine; N⁶-(5-hydroxy-1-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(1-hydroxy-1-tetrahydronaphthyl)methyl-2′-O-methyl­adenosine; N⁶-(5-methoxy-1-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(6-methoxy-1-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(7-methoxy-1-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(4-chromanyl)-2′-O-methyladenosine; N⁶-(4-thiochromanyl)-2′-O-methyladenosine; N⁶-(9-fluorenyl)-2′-O-methyladenosine; N⁶-(9-fluorenyl)methyl-2′-O-methyladenosine; N⁶-(9-hydroxy-9-fluorenyl)methyl-2′-O-methyladenosine; N⁶-(9-xanthenyl)methyl-2′-O-methyladenosine and N⁶-cyclohexyl-2,2′-O-dimethyladenosine;

Claim 15

N⁶-cyclopentyl-2′-O-methyladenosine; N⁶-cyclohexyl-2′-O-methyladenosine; N⁶-(2,3-dihydroxypropyl)-2′-O-methyladenosine; N⁶-benzyl-2′-O-methyladenosine; N⁶-(2,2-diphenylethyl)-2′-O-methyladenosine; N⁶-(exo-dicyclo[2,2,1]heptyl)-2′-O-methyladenosine; N⁶-(endo-dicyclo[2,2,1]heptyl)-2′-O-methyladenosine; N⁶-(1-naphthyl)methyl-2′-O-methyladenosine; N⁶-(1-acenaphthylenyl)methyl-2′-O-methyladenosine; N⁶-(1,2-dihydro-1-acenaphthylenyl)methyl-2′-O-methyladeno­sine; N⁶-(2,3-dihydro-1H-indene-1-yl)-2′-O-methyladenosine; N⁶-(2,3-dihydro-1H-indene-2-yl)-2′-O-methyladenosine; N⁶-(2,3-dihydro-1H-indene-1-yl)methyl-2′-O-methyladenosine; N⁶-(3H-indene-1-yl)methyl-2′-O-methyladenosine; N⁶-(5-methoxy-2,3-dihydro-1H-indene-1-yl)-2′-O-methyl­adenosine; N⁶-(1-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(2-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(3,4-dihydro-1-naphthyl)methyl-2′-O-methyladenosine; N⁶-(5-hydroxy-1-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(1-hydroxy-1-tetrahydronaphthyl)methyl-2′-O-methyl­adenosine; N⁶-(5-methoxy-1-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(6-methoxy-1-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(7-methoxy-1-tetrahydronaphthyl)-2′-O-methyladenosine; N⁶-(4-chromanyl)-2′-O-methyladenosine; N⁶-(4-thiochromanyl)-2′-O-methyladenosine; N⁶-(9-fluorenyl)-2′-O-methyladenosine; N⁶-(9-fluorenyl)methyl-2′-O-methyladenosine; N⁶-(9-hydroxy-9-fluorenyl)methyl-2′-O-methyladenosine; N⁶-(9-xanthenyl)methyl-2′-O-methyladenosine and N⁶-cyclohexyl-2,2′-O-dimethyladenosine;

Claim 16

A pharmaceutical composition comprising as an active ingredient an effective amount of at least one adenosine derivative of the formula (I) or a salt thereof as claimed in any one of claims 1 to 13.

Claim 17

A pharmaceutical composition as claimed in claim 14 which is an antihypertensive agent.

Claim 18

The use of adenosine derivatives of the formula (I) as defined in any one of claims 1 to 14, and pharmaceutically acceptable salts thereof, for the manufacture of antihypertensive agents.

Claim 19

Process for the production of adenosine derivatives having the formula I given in claim 1 wherein the substituents have the meanings given in claim 1 by substantially conventional methods such as those hereinbefore described.