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Amorphous Forms of (1S,2S,3R,5S)-3-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl] amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5,d]pyrimidine-3-yl]-5-(2- hydroxyethoxy)-1,2-cyclopentanediol

IP.com Disclosure Number: IPCOM000207885D
Publication Date: 2011-Jun-15
Document File: 3 page(s) / 117K

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The IP.com Prior Art Database

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Amorphous Forms of (1S,2S,3R,5S)-3-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclo- propyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5,d]pyrimidine-3-yl]-5-(2- hydroxyethoxy)-1,2-cyclopentanediol

(1S,2S,3R,5S)-3-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5-(propylthio)- 3H-1,2,3-triazolo[4,5,d]pyrimidine-3-yl]-5-(2-hydroxyethoxy)-1,2-cyclopentanediol, has the following chemical structure:

F

F

HN

N

N

N

S

N

N

O

HO

HO OH

Amorphous form of this compound can be obtained by using known techniques such as, but not limited to, spray dry, freeze dry, evaporation, lyophilization, precipitation, quenching and grinding.

Provided below are several examples, and an XRD figure of the obtained amorphous form.

Example 1: spray drying

500 mg of (1S,2S,3R,5S)-3-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5- (propylthio)-3H-1,2,3-triazolo[4,5,d]pyrimidine-3-yl]-5-(2-hydroxyethoxy)-1,2- cyclopentanediol was dissolved in 8 ml of methanol at RT and spray dried at following conditions: Tinl=80°C, Tout=50°C, Aspirator at 100% and Pump Flow at 20%.

Example 2: evaporation

300 mg of (1S,2S,3R,5S)-3-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5- (propylthio)-3H-1,2,3-triazolo[4,5,d]pyrimidine-3-yl]-5-(2-hydroxyethoxy)-1,2- cyclopentanediol was dissolved in 8 ml of methanol at RT and evaporated at reduced pressure.

1


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Example 3: quenching

50 mg of (1S,2S,3R,5S)-3-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5- (propylthio)-3H-1,2,3-triazolo[4,5,...