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Last Updated: March 28, 2024

Claims for Patent: RE46276


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Summary for Patent: RE46276
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: ##STR00001## wherein R, X and R.sup.1 through R.sup.3 are as defined in the specification.
Inventor(s): Hardem; David (Sutton Bonington, GB), Ingall; Anthony (Minehead, GB), Springthorpe; Brian (Stanford on Soar, GB), Willis; Paul (Geneva, CH), Guile; Simon (Hathern, GB)
Assignee: AstraZeneca UK Limited (London, GB)
Application Number:14/976,977
Patent Litigation and PTAB cases: See patent lawsuits and PTAB cases for patent RE46276
Patent Claims: 1. A compound of formula (I) ##STR00015## 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.2CH.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.2CH.sub.2CF.sub.3, butyl or pentyl, the phenyl group at R.sup.2 must be substituted by fluorine; when X is OCH.sub.2CH.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.2OH or OCH.sub.2CH.sub.2OH.

5. A compound according to claim 1 which is: [1R-[1.alpha.,2.alpha.,3.beta.(1R*,2S*),5.beta.]]-3-[7-[[2-(4-Fluoropheny- l)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-Difluorop- henyl)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.]].]..Iadd.[1S-[1.alpha- .,2.alpha.,3.beta.(1S*,2R*),5.beta.]].Iaddend.-3-[7-[[2-(3,4-Difluoropheny- l)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl- ]-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].]..Iadd.7-[[2-(4-fluorophenyl)cyclopr- opyl]amino].Iaddend.-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-cyclopentane-- 1,2,3-triol; [1S-(1.alpha.,2.alpha.,3.beta.(1S*,2R*),5.beta.]-3-[7-[[2-(3,4-Difluoroph- enyl)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-tri- azolo[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- -yl]cyclopentane-1,2,3-triol; [1S-[1.alpha.,2.alpha.,3.beta.(1S*,2R*),5.beta.]]-3-[5-(Butylthio)-7-[(2-- phenylcyclopropyl)amino]-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydr- oxethoxy)-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.]. .Iadd.adjuvant .Iaddend.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): ##STR00016## 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.2CH.sub.2OR' where R' is C.sub.1-6 alkyl or benzyl, and L is a leaving group, with a compound of formula (III): ##STR00017## 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-Fluoro- phenyl)cyclopropyl]amino]-5-(propylsulphonyl)-3H-1,2,3-triazolo[4,5-d]pyri- midin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-methanol; .[.[[3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]].]..Iadd.[3aR-[- 3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]].Iaddend.-6-[7-[[2-(4-Fluo- rophenyl)cyclopropyl]amino]-5-[(3,3,3-trifluoropropy)lthio]-3H-1,2,3-.[.tr- iazolo[4,5-d]pyrimidin-3-yl).]..Iadd.triazolo[4,5-d]pyrimidin-3-yl].Iadden- d.-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-(3,4-Diflu- orophenyl)cyclopropyl]amino]-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-tria- zolo[4,5-d]pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxo- le-4-methanol; [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-cyclope- nta-1,3-dioxol-4-ol; [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-cyclo- penta-1,3-dioxol-4-ol]oxy]acetic acid, methyl ester; .Iadd.or.Iaddend. [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-[[6-[7-Bromo-5-(propylthio)- -3H-1,2,3-triazolo[4,5-d]-pyrimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclo- penta-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-Di- fluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]-py- rimidin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ac- etic acid, methyl ester; [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]pyrimi- din-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethan- ol; [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-cyclo- penta-1,3-dioxole-4-methanol; .Iadd.or.Iaddend. [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-dioxole-4-methanol.[.;.]..Iadd...Iaddend.

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-cyclopent- a-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-cyclopent- a-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-cyclopent- a-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]pyrimi- din-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- -Fluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]py- rimdin-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol; .Iadd.or.Iaddend. [3aR-[3a.alpha.,4.alpha.,6.alpha.,6a.alpha.(1S*,2R*)]]-6-[[7-[(4-Fluoroph- enyl)cyclopropyl]amino]-5-(propylsulphonyl)-3H-1,2,3-triazolo[4,5-d]pyrimi- din-3-yl]-tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol.[.;.]..Iad- d...Iaddend.

12. The compounds: [3aR-[3a.alpha.,4.alpha.,6.alpha.,6a.alpha.(1S*,2R*)]]-6-[7-[[(4-Fluoroph- enyl)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-Difluorop- henyl)cyclopropyl]amino]-5-(propylsulphonyl)-3H-1,2,3-triazolo[4,5-d]pyrim- idin-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]-- pyrimidin-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]py- rimidin-3-yl]-2-cyclopenten-1-yl]oxy]-acetic acid, ethyl ester; .Iadd.or.Iaddend. [1S-(cis)] 2-[[4-[7-Amino-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazolo[4,5-d]py- rimidin-3-yl]-2-cyclopenten-1-yl]oxy]-1-ethanol.[.;.]..Iadd...Iaddend.

13. The compounds: [3aR-(3a.alpha.,4.alpha.,6.alpha.,6a.alpha.)]-2-[6-[7-Amino-5-[(3,3,3-tri- fluoropropyl)thio]-3H-1,2,3-triazolo[4,5-d]-pyrimidin-3-yl]-tetrahydro-2,2- -dimethyl-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-tri- fluoropropyl)thio]-3H-1,2,3-triazolo[4,5-d]-pyrimidin-3-yl]-tetrahydro-2,2- -dimethyl-4H-cyclopenta-1,3-dioxol-4-yloxy]ethanol; [3aR-[3a.alpha.,4.alpha.,6.alpha.(1R*,2S*),6a.alpha.]-2-[6-(7-Phenylcyclo- propyl)amino]-5-[(3,3,3-trifluoropropyl)thio]-3H-1,2,3-triazolo[4,5-d]pyri- midin-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-Difluor- ophenyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidi- n-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-Difluo- rophenyl)cyclopropyl]amino]-5-(propylsulfonyl)-3H-1,2,3-triazolo[4,5-d]pyr- imidin-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]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.]]-2-[6-[[5-(Butylthi- o)-7-chloro-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-tetrahydro-2,2-dimethy- l-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol; .Iadd.or.Iaddend. [3aR-[3a.alpha.,4.alpha.,6a.alpha.(1R*,2S*),6a.alpha.]]-2-[6-[[5-(Butylth- io)-7-[2-phenylcyclopropyl]amino-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-t- etrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol.[.;.]..I- add...Iaddend.

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.

.Iadd.15. A compound chosen from: [1R-[1.alpha.,2.alpha.,3.beta.(1R*,2S*),5.beta.]]-3-[7-[[2-(4-Fluoropheny- l)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-Difluorop- henyl)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-Difluorop- henyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-- 3-yl]-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-y- l]-5-(hydroxymethyl)-cyclopentane-1,2-diol; [1S-[1.alpha.,2.beta.,3.beta.,4.alpha.(1S*,2R*)]]-4-[5-(Butylthio)-7-[[2-- (4-fluorophenyl)cyclopropyl]amino]-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]- -cyclopentane-1,2,3-triol; and pharmaceutically acceptable salts and solvates thereof, and solvates of such salts..Iaddend.

.Iadd.16. A compound chosen from: [1R-[1.alpha.,2.alpha.,3.beta.(1R*,2S*),5.beta.]]-3-[7-[[2-(4-Fluoropheny- l)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-Difluorop- henyl)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-Difluorop- henyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-- 3-yl]-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; and [1S-[1.alpha.,2.beta.,3.beta.,4.alpha.(1S*,2R*)]]-4-[5-(Butylthio)-7-[[2-- (4-fluorophenyl)cyclopropyl]amino]-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]- -cyclopentane-1,2,3-triol..Iaddend.

.Iadd.17. A compound chosen from: [1R-[1.alpha.,2.alpha.,3.beta.(1R*,2S*),5.beta.]]-3-[7-[[2-(3,4-Difluorop- henyl)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-Difluorop- henyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-- 3-yl]-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol; and pharmaceutically acceptable salts and solvates thereof, and solvates of such salts..Iaddend.

.Iadd.18. A compound chosen from: [1R-[1.alpha.,2.alpha.,3.beta.(1R*,2S*)5,.beta.]]-3-[7-[[2-(3,4-Difluorop- henyl)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; and [1S-[1.alpha.,2.alpha.,3.beta.(1S*,2R*),5.beta.]]-3-[7-[[2-(3,4-Difluorop- henyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-- 3-yl]-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol..Iaddend.

.Iadd.19. An oral pharmaceutical composition comprising [1S-[1.alpha.,2.alpha.,3.beta.(1S*,2R*),5.beta.]]-3-[7-[[2-(3,4-Difluorop- henyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-- 3-yl]-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol in combination with a pharmaceutically acceptable diluent, adjuvant, and/or carrier suitable for oral administration, wherein said oral pharmaceutical composition is in the form of a tablet, pill, capsule, liquid, powder, or granule..Iaddend.

.Iadd.20. The oral pharmaceutical composition according to claim 19, wherein said oral pharmaceutical composition is in the form of a tablet..Iaddend.

.Iadd.21. The oral pharmaceutical composition according to claim 19, wherein said liquid is a syrup or suspension..Iaddend.

.Iadd.22. A method of treatment of post-myocardial infarction which comprises orally administering to a patient suffering therefrom a therapeutically effective amount of [1S-[1.alpha.,2.alpha.,3.beta.(1S*,2R*),5.beta.]]-3-[7-[[2-(3,4-Difluorop- henyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-- 3-yl]-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol..Iaddend.

.Iadd.23. A method of treatment of stroke which comprises orally administering to a person suffering therefrom a therapeutically effective amount of [1S-[1.alpha.,2.alpha.,3.beta.(1S*,2R*),5.beta.]]-3-[7-[[2-(3,4- -Difluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]- pyrimidin-3-yl]-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol..Iaddend.

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