Favipiravir

• Molecular FormulaC5H4FN3O2
• Average mass157.103 Da

SYNTHESIS AT https://newdrugapprovals.org/2015/08/18/filgotinib/

259793-96-9 [RN]

2-Pyrazinecarboxamide, 6-fluoro-3,4-dihydro-3-oxo-

 

6-Fluoro-3-hydroxypyrazine-2-carboxamide

6-Fluoro-3-oxo-3,4-dihydro-2-pyrazinecarboxamide

 

8916

Avigan

ファビピラビル
Favipiravir

SYN

https://link.springer.com/article/10.1007/s11696-018-0654-9

Electronic supplementary material

 

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1315 kb)

Ref

https://pdfs.semanticscholar.org/be8e/cb882b99204983d2f60077c7ab8b53f4d62c.pdf

Drug Discoveries & Therapeutics. 2014; 8(3):117-120.

 mp = 178-180°C. 1 H-NMR (600 MHz, DMSO): δ 12.34 (brs, 1H, OH), 8.31 (d, 1H, pyrazine H, J = 8.0 Hz), 7.44 (s, 1H, CONH2), 5.92 (s, 1H, CONH2). 13C-NMR (75 MHz, DMSO): δ 168.66, 159.69, 153.98, 150.76, 135.68. HRMS (ESI): m/z [M + H]+ calcd for C5H5FN3O2 + : 158.0366; found: 158.0360.

PAPER

Chemical Papers (2017), 71(11), 2153-2158.

https://link.springer.com/article/10.1007%2Fs11696-017-0208-6

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 514 kb)

Take a tour

Kerkennah Islands

Kerkennah Islands seen from space
Kerkennah Islands
Geography
Coordinates	34°42′N 11°11′ECoordinates: 34°42′N 11°11′E
Area	160 km2 (62 sq mi)
Administration
Tunisia

Kerkennah Islands (Tunisian Arabic: قرقنة‎ qarqna) are a group of islands lying off the east coast of Tunisia in the Gulf of Gabès, at 34°42′N 11°11′E. The Islands are low-lying, being no more than 13 metres (43 feet) above sea level. The main islands are Chergui and Gharbi. The archipelago has an area of 160 square kilometres (62 sq mi) and a population of 15,501 (2014).^[2]

Kerkennah's main town, Remla (on Chergui), has a population of 2,000. The population of the islands significantly decreased during the 1980s due to drought. The islands were unable to provide suitable irrigation systems and, with clean water rapidly running out, many islanders were forced to leave for mainland Tunisia, the nearest town being Sfax.

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NIDUFEXOR

NIDUFEXOR

LMB763

4-[[benzyl-(8-chloro-1-methyl-4H-chromeno[4,3-c]pyrazole-3-carbonyl)amino]methyl]benzoic acid

Nidufexor is a farnesoid X receptor (FXR) agonist.

Molecular Weight	487.93
Formula	C₂₇H₂₂ClN₃O₄
CAS No.	1773489-72-7

PHASE 2 Treatment of Liver and Biliary Tract Disorders,
Agents for Diabetic Nephropathy, NOVARTIS

Nidufexor

1773489-72-7, LMB-763, UNII-CJ1PL0TE6J, CJ1PL0TE6J, BCP28929, EX-A1854

Nidufexor pound LMB-763 pound(c)

ZINC584641402

4-((N-benzyl-8-chloro-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)methyl)benzoic acid

HY-109096

CS-0039398

https://pubs.acs.org/doi/pdf/10.1021/acs.jmedchem.9b01621

1 (7.6 g, 89% yield) as a white solid. Melting point: 232.6 °C.

1 H NMR (400 MHz, DMSO): δ 12.93 (s, 1H), 7.96−7.85 (m, 2H), 7.71 (dd, J = 7.1, 2.5 Hz, 1H), 7.42−7.20 (m, 8H), 7.06 (dd, J = 8.7, 1.9 Hz, 1H), 5.45 (d, J = 3.9 Hz, 2H), 5.25 (d, J = 9.2 Hz, 2H), 4.58 (d, J = 12.1 Hz, 2H), 4.12 (d, J = 16.6 Hz, 3H).

13C NMR (101 MHz, DMSO-d6): δ 167.07, 162.21, 151.98, 142.65, 139.18, 132.20, 132.67, 129.70, 129.50, 129.50, 128.53, 128.53, 127.43, 127.43, 127.43, 127.43, 127.43, 125.53, 122.24, 119.0, 117.09, 116.64, 64.51, 50.68, 48.24. LC-MS m/z: 488.2/490.2 (M +H)+ ; chlorine pattern; method 3; RT = 1.41 min.

Elemental Analysis calcd for C27H22ClN3O4: C 66.46, H 4.54, N 8.61; found: C 66.43, H 4.56, N 8.62.

TRIS Salt Formation. Methanol (400 mL) was added to a mixture of 1 (4.0 g, 8.2 mmol) and 2-amino-2-hydroxymethylpropane-1,3-diol (TRIS, 1.0 g, 8.2 mmol). The mixture was heated to 70 °C for 0.5 h. After cooling to room temperature, the solvent was removed in vacuum. The residue was sonicated in dichloromethane (10 mL) and concentrated again. The resulting white solid was dried under vacuum overnight. The crude material was crystallized by slurring the solid residue in a 4:1 mixture of acetonitrile and methanol (5 mL). The mixture was stirred at room temperature for 24 h to give 4-((N-benzyl-8-chloro-1-methyl-1,4-dihydrochromeno- [4,3-c]pyrazole-3-carboxamido)methyl)benzoic acid TRIS salt as a white salt (3.7 g, 73% yield). Melting point: 195.6 °C. 1 H NMR (400 MHz, DMSO): δ 7.92−7.80 (m, 2H), 7.78−7.64 (m, 1H), 7.41− 7.19 (m, 8H), 7.13−7.00 (m, 1H), 5.44 (s, 2H), 5.25−5.14 (m, 2H), 4.61−4.48 (m, 2H), 4.18−4.03 (m, 3H), 3.39 (s, 7H). TRIS OH masked by water peak. LC-MS m/z: 488.0/490.0 (M+H)+ ; chlorine pattern, method 3. RT = 1.58 min. Elemental Analysis calc for C31H33ClN4O7: C 61.00, H 5.36, N 9.15; found: C 60.84, H 5.34, N 9.13.

https://pubs.acs.org/doi/suppl/10.1021/acs.jmedchem.9b01621/suppl_file/jm9b01621_si_001.pdf

Patent

WO 2015069666

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2015069666&tab=PCTDESCRIPTION

///////NIDUFEXOR, LMB 763, Phase II, PHASE 2, Liver and Biliary Tract Disorders,  Diabetic Nephropathy, NOVARTIS

CN1C(C2=CC(Cl)=CC=C2OC3)=C3C(C(N(CC4=CC=CC=C4)CC5=CC=C(C(O)=O)C=C5)=O)=N1