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Claims for Patent: 6,525,060

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Claims for Patent: 6,525,060

Title: Triazolo(4,5-d)pyrimidine compounds
Abstract:Triazolo[4,5-d]pyrimidine compounds, their use as medicaments, compositions containing them and processes for their preparation. The compounds of the invention have the formula (I) as follows: ##STR1## wherein R, X and R.sup.1 through R.sup.3 are as defined in the specification.
Inventor(s): Hardern; David (Sutton Bonington, GB), Ingall; Anthony (Loughborough, GB), Springthorpe; Brian (Loughborough, GB), Willis; Paul (West Bridgford, GB), Guile; Simon (Loughborough, GB)
Assignee: Astrazeneca UK Limited (London, GB)
Application Number:09/508,195
Patent Claims: 1. A compound of formula (I) ##STR15##

wherein: R.sup.1 is C.sub.3-5 alkyl optionally substituted by one or more halogen atoms; R.sup.2 is a phenyl group, optionally substituted by one or more fluorine atoms; R.sup.3 and R.sup.4 are both hydroxy; R is XOH, where X is CH.sub.2, OCH.sub.2 CH.sub.2 or a bond;

or a pharmaceutically acceptable salt or solvate thereof, or a solvate of such a salt provided that: when X is CH.sub.2 or a bond, R.sup.1 is not propyl; when X is CH.sub.2 and R.sup.1 is CH.sub.2 CH.sub.2 CF.sub.3, butyl or pentyl, the phenyl group at R.sup.2 must be substituted by fluorine; when X is OCH.sub.2 CH.sub.2 and R.sup.1 is propyl, the phenyl group at R.sup.2 must be substituted by fluorine.

2. A compound according to claim 1 in which R.sup.1 is 3,3,3,-trifluoropropyl, butyl or propyl.

3. A compound according to claim 1 in which R.sup.2 is phenyl or 4-fluorophenyl or 3,4-difluorophenyl.

4. A compound according to claim 1 in which R is CH.sub.2 OH or OCH.sub.2 CH.sub.2 OH.

5. A compound according to claim 1 which is: [1R-[1.alpha.,2.alpha.,3.beta.(1R*,2S*),5.beta.]]-3-[7-[[2-(4-Fluorophenyl) cyclopropyl]amino]-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazolo[4,5-d] pyrimidin-3-yl]-5-(hydroxymethyl)-cyclopentane-1,2-diol; [1R-[1.alpha.,2.alpha.,3.beta.(1R*,2S*),5.beta.]]-3-[7-[[2-(3,4-Difluorophe nyl)cyclopropyl]amino]-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazolo[4, 5-d]pyrimidin-3-yl]-5-(hydroxymethyl)-cyclopentane-1,2-diol; [1S-(1.alpha.,2.alpha.,3.beta.(1S*,2R*),5.beta.]]-3-[7-[[2-(3,4-Difluorophe nyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-y l]-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol; 1R-[1.alpha.,2.alpha.,3.beta.(1R*,2S*),5.beta.]]-3-[5-(Butylthio)-7-[[2-(3, 4-difluorophenyl)cyclopropyl]amino]-3H-1,2,3-triazolo [4,5-d]pyrimidin-3-yl]-5-(hydroxymethyl)-cyclopentane-1,2-diol; [1S-[1.alpha.,2.beta.,3.beta.,4.alpha.(1S*,2R*)]]-4-[5-(Butylthio)-7-[[2-(4 -flurophenyl)cyclopropyl]amino]-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-cyc lopentane-1,2,3-triol; [1S-(1.alpha.,2.alpha.,3.beta.(1S*,2R*),5.beta.]-3-[7-[[2-(3,4-Difluorophen yl)cyclopropyl]amino]-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazolo[4,5 -d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol; [1S-[1.alpha.,2.alpha.,3.beta.,5.beta.(1S*,2R*)]]-3-(2-Hydroxyethoxy)-5-[7- (2-phenylcyclopropyl)amino]-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazo lo[4,5-d]pyrimidin-3-yl]-cyclopentane-1,2-diol [1S-[1.alpha.,2.beta.,3.beta.,4.alpha.(1S*,2R*)]]-4-[5-(Butylthio)-7-[[2-( 3,4-difluorophenyl)cyclopropyl]amino]-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-y l]cyclopentane-1,2,3-triol; [1S-[1.alpha.,2.alpha.,3.beta.(1S*,2R*),5.beta.]]-3-[5-(Butylthio)-7-[(2-ph enylcyclopropyl)amino]-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxe thoxy)-cyclopentane-1,2-diol;

or pharmaceutically acceptable salts or solvates thereof, or solvates of such salts.

6. A pharmaceutical composition comprising a compound according to claim 1 in combination with a pharmaceutically acceptable diluent, adjuvent and/or carrier.

7. A method of treatment of post-myocardial infarction which comprises administering to a patient suffering therefrom a therapeutically effective amount of a compound according to claim 1.

8. A process for the preparation of a compound of formula (I) which comprises reacting a compound of formula (II): ##STR16##

where R, R.sup.1, R.sup.3 and R.sup.4 are as defined in claim 1, or are protected derivatives thereof, or R.sup.3 and R.sup.4 together form a bond in the 5-membered ring, or R is CH.sub.2 CH.sub.2 OR' where R' is C.sub.1-6 alkyl or benzyl, and L is a leaving group, with a compound of formula (III): ##STR17##

where R.sup.2 is defined in claim 1 or is a protected derivative thereof, in the presence of a base in an inert solvent at ambient or elevated temperature, and optionally thereafter and in any order: converting one or more functional groups into further functional groups; removing any protecting groups; forming a pharmaceutically acceptable salt or solvate, or a solvate of such a salt.

9. The compounds: [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]]-6-[7-[[2-(4-Fluoroph enyl)cyclopropyl]amino]-5-(propylsulphonyl)-3H-1,2,3-triazolo[4,5-d]pyrimid in-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-methanol; [[3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]]-6-[7-[[2-(4-Fluorop henyl)cyclopropyl]amino]-5-[(3,3,3-trifluoropropy)lthio]-3H-1,2,3-triazolo[ 4,5-d]pyrimidin-3-yl)-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-m ethanol; [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]-6-[7-[[2-(3,4-Difluor ophenyl)cyclopropyl]amino]-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazol o[4,5-d]pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4 -methanol; [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-6-[7-Amino-5-(propylthio)-3H- 1,2,3-triazolo[4,5-d]-pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta -1,3-dioxol-4-ol; [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-[[6-[7-Amino-5-(propylthio)-3 H-1,2,3-triazolo[4,5-d]-pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopen ta-1,3-dioxol-4-ol]oxy]acetic acid, methyl ester; [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-[[6-[7-Bromo-5-(propylthio)-3 H-1,2,3-triazolo[4,5-d]-pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopen ta-1,3-dioxol-4-ol]oxy]acetic acid, methyl ester.

10. The compounds: [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]]-[[6-[7-[[2-(3,4-Difl uorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]-pyrim idin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]acetic acid, methyl ester; [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]]-6-[[7-[2-(3,4-Difluo rophenyl)cyclopropyl]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin -3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol; [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-6-[7-Amino-5-(propylthio)-3H- 1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta- 1,3-dioxole-4-methanol; [3aR-(3a.alpha.,4.alpha.,6a.alpha.)]-6-[7-Amino-5-(propylsulfonyl)-3H-1,2,3 -triazolo[4,5-d]pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-d ioxole-4-methanol;

11. The compounds: [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-6-[7-Amino-5-(butylthio)-3H-1 ,2,3-triazolo[4,5-d]pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1 ,3-dioxole-4-methanol; [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-6-[7-Amino-5-(butylthio)-3H-1 ,2,3-triazolo[4,5-d]pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1 ,3-dioxole-4-methanol, acetate; [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-6-[7-Bromo-5-(butylthio)-3H-1 ,2,3-triazolo[4,5-d]pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1 ,3-dioxole-4-methanol, acetate; [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]]-6-[5-(Butylthio)-7-[ [2-(3,4-difluorophenyl)cyclopropyl]amino]-3H-1,2,3-triazolo[4,5-d]pyrimidin -3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-methanol, acetate; [3aR-[3a.alpha.,4.alpha.,6.alpha.,6a.alpha.(1S*,2R*)]]-6-[7-[[(4-Fluorophen yl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimdin-3-yl] -tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol; [3aR-[3a.alpha.,4.alpha.,6.alpha.,6a.alpha.(1S*,2R*)]]-6-[[7-[(4-Fluorophen yl)cyclopropyl]amino]-5-(propylsulphonyl)-3H-1,2,3-triazolo[4,5-d]pyrimidin -3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol;

12. The compounds: [3aR-[3a.alpha.,4.alpha.,6.alpha.,6a.alpha.(1S*,2R*)]]-6-[7-[[(4-Fluorophen yl)cyclopropyl]amino]-5-(butylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl] -tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol; [1S-(1.alpha.,2.alpha.,3.beta.(1S*,2R*),5.beta.)]-3-[7-[[2-(3,4-Difluorophe nyl)cyclopropyl]amino]-5-(propylsulphonyl)-3H-1,2,3-triazolo[4,5-d]pyrimidi n-3-yl)-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol; (1S-cis) 2-[[4-[7-Chloro-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazolo[4,5-d]-p yrimidin-3-yl]-2-cyclopenten-1-yl]oxy]-acetic acid, ethyl ester; [1S-(cis)] 2-[[4-[7-Amino-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazolo[4,5-d]pyr imidin-3-yl]-2-cyclopenten-1-yl]oxy]-acetic acid, ethyl ester; [1S-(cis)] 2-[[4-[7-Amino-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazolo[4,5-d]pyr imidin-3-yl]-2-cyclopenten-1-yl]oxy]-1-ethanol;

13. The compounds: [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-2-[6-[7-Amino-5-[(3,3,3-trifl uoropropyl)thio]-3H-1,2,3-triazolo[4,5-d]-pyrimidin-3-yl]-tetrahydro-2,2-di methyl-4H-cyclopenta-1,3-dioxol-4-yloxy]ethanol; [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-2-[6-[7-Bromo-5-[(3,3,3-trifl uoropropyl)thio]-3H-1,2,3-triazolo[4,5-d]-pyrimidin-3-yl]-tetrahydro-2,2-di methyl-4H-cyclopenta-1,3-dioxol-4-yloxy]ethanol; [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]-2-[6-(7-Phenylcyclopr opyl)amino]-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazolo[4,5-d]pyrimid in-3-yl]-tetrahydro-2,2-dimethyl-4H-1,3-dioxol-4-yloxy]ethanol; [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]-6-[[7-[(3,4-Difluorop henyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3 -yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol; [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]]-6-[[7-[(3,4-Difluoro phenyl)cyclopropyl]amino]-5-(propylsulfonyl)-3H-1,2,3-triazolo[4,5-d]pyrimi din-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol; [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]]-6-[5-(Butylthio)-7-[ [2-(3,4-difluorophenyl)cyclopropyl]amino]-3H-1,2,3-triazolo[4,5-d]pyrimidin -3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol; [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]]-2-[6-[[5-(Butylthio) -7-chloro-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4 H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol; [3aR-[3a.alpha.,4.alpha.,6a.alpha.(1R*,2S*),6a.alpha.]]-2-[6-[[5-(Butylthio )-7-[2-phenylcyclopropyl]amino-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-tetr ahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol;

14. A method of treatment of stroke which comprises administering to a person suffering therefrom a therapeutically effective amount of the compound according to claim 1.
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