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N-(2-(4-(4-fluorobenzylcarbamoyl) -5-hydroxy-1-methyl-6-oxo-1, 6-dihydropyrimidin-2-yl)propan-2-yl) -5-methyl-1,3,4-oxadiazole-2- carboxamide potassium salt

IP.com Disclosure Number: IPCOM000202169D
Publication Date: 2010-Dec-07
Document File: 2 page(s) / 75K

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The IP.com Prior Art Database

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  N-(2-(4-(4-fluorobenzylcarbamoyl) -5-hydroxy-1-methyl-6- oxo-1, 6-dihydropyrimidin-2-yl)propan-2-yl) -5-methyl-1,3,4- oxadiazole-2- carboxamide potassium salt

   N-(2-(4-(4-fluorobenzylcarbamoyl) -5-hydroxy-1-methyl-6-oxo-1, 6-dihydropyrimidin- 2-yl)propan-2-yl) -5-methyl-1,3,4-oxadiazole-2- carboxamide potassium salt (referred as "RLT") of the following formula;

O

OK

F

N

N

N

H

N

O

H

N

O

N

O

is an antiretroviral drug used to treat HIV infection. The purity of commercial RLT is reported herein.

The following impurities can be found in the tablets:
Starting material

O

OH

F

N

H2N

H

N

N

O

RLT Des-Fluoro

O

OH

N

N

N

H

N

O

H

N

O

N

O

The presence of RLT Des-Fluoro can be from starting material or process related.

Chromatographic purity of Isentress tablet:
One tablet of Isentress, containing about 400 mg of RLT was dissolved with aid of sonication in 100 mL of Diluent, centrifuged at 4000 rpm for 5 min and supernatant injected into HPLC system.

The HPLC conditions are:
Column: YMC-UltraHT Pro C18, 2.0μm, 100×3.0mm or equivalent Eluent A: 0.1% v/v HCLO4 (70%) in water
Eluent B: Acetonitrile (HPLC grade)

Time (min) % Eluent A % Eluent B 0 75 25

Gradient:

15 45 55


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                    21 45 55 Re-equilibration time: 7 min
Injection volume: 5 ~L
Flow Rate: 0.6 mL/min
Detector: UV 245 nm
Column temperature: 40 °C
Autosampler temperature: 10 °C
Diluent: Mixture Water / Acetonitrile (3:1 v/v)

The obtained results represented in the table below:

Impurity profile (% area)

                          RLT des-Fluro-RLT
RR...