Amprenavir
KVX-478, 141W94, VX-478,
DrugSyn.org
US5585397
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate
(3S)-tetrahydro-3-furyl N-[(1S,2R)-3-(4-amino-N-isobutylbenzenesulphonamido)-1-benzyl-2-hydroxypropyl] carbamate
CAS NO. 161814-49-9, [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
| 161814-49-9 | |
| Weight | 505.224656557 |
|---|---|
| Chemical Formula | C25H35N3O6S |
| Amprenavir is a protease inhibitor used to treat HIV infection. |
Production of amprenavir was discontinued by the manufacturer December 31, 2004; a prodrug version (fosamprenavir) is available.
| Amprenavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Amprenavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs. |
| Country | Patent Number | Approved | Expires (estimated) |
|---|---|---|---|
| United States | 5585397 | 1993-12-17 | 2013-12-17 |
| United States | 6730679 | 1997-11-11 | 2017-11-11 |
PATENT
Example 11Synthesis of Amprenavir (1)To a solution of carbamate
nitro derivative 15 (0.05 g, 0.09 mmol) in 2 mL of EtOAc was added SnCl2.2H2O
(0.1 g, 0.5 mmol) at 70° C. The reaction mixture was heated for 1 h
until starting material disappeared and the solution cooled to room
temperature. It was then poured into saturated aq. NaHCO3 solution and extracted with EtOAc. The organic extract was dried over anhyd. Na2SO4 and
concentrated under reduced pressure. It was purified over
chromatography using petroleum ether:EtOAc (3:2) to give amprenavir 1
(0.04 g, 90%).IR: (CHCl3, cm−1): υmax 757, 1090, 1149, 1316, 1504, 1597, 1633, 1705, 2960, 3371; 1H NMR (200 MHz, CDC3):
δ 0.86 (d, J=5.7 Hz, 3H), 0.90 (d, J=6.6 Hz, 3H), 1.78-2.21 (m, 3H),
235-3.11 (m, 6H), 3.58-4.11 (m, 7H), 4.25 (s, 2H), 5.01 (br s, 1H), 5.07
(br s, 1H), 6.65 (d, J=8.4 Hz, 2H), 7.20-7.28 (m, 5H), 7.51 (d, J=8.4
Hz, 2H); 13C NMR (50 MHz, CDC3):
δ 19.9, 20.2, 27.3, 32.8, 35.4, 35.7, 53.8, 55.0, 58.6, 66.8, 72.6,
73.2, 75.3, 114.0, 125.9, 126.5, 1280.4, 129.5, 137.7, 150.9, 155.9;
Anal. Calcd for C25H35N3O6S: C, 59.39; H, 6.98; N, 8.31; S, 6.34. Found: C, 59.36; H, 6.81; N, 8.25; S, 6.29%.
Process for synthesis of syn azido epoxide and its use as intermediate for the synthesis of amprenavir & saquinavir
US 20150011782 A1
US 20150011782 A1
| Publication number | US20150011782 A1 |
| Publication type | Application |
| Application number | US 14/371,466 |
| PCT number | PCT/IN2013/000021 |
| Publication date | Jan 8, 2015 |
| Filing date | Jan 10, 2013 |
| Priority date | Jan 10, 2012 |
| Also published as | WO2013105118A1, WO2013105118A8 |
| Inventors | Sunita Khanderao Gadakh, Reddy Santhosh Rekula, Arumugam Sudalai |
| Original Assignee | Council Of Scientific & Industrial Research |
