Actarit

Crystalline SolidActarit is an orally administered disease-modifying antirheumatic drug launched in Japan. Although its structure resembles that of non-steroidal anti-inflammatory drugs, it has no effect on experimental acute inflammation and has no analgesic or antipyretic effects. Its preventative and therapeutic effects on adjuvant arthritis are mediated via modulation of production and serum level of interleukin-2 which enhances production of suppressor T-cells to the immune system, th

Actarit is an anilide and a member of acetamides.

p-Aminophenylacetic acid (1.02 mmol) (manufactured by Wako Pure Chemical Industries) was dissolved indichloromethane-methanol-water (1:3:1, 50 ml), and acetic anhydride (2.12 mmol) was added thereto under ice-cooling, followed by stirring overnight while gradually returning to room temperature. The solvent was evaporated under reducedpressure to give the titled compound (196.4 mg, yield 99percent). The structure was identified by 1H-NMR1H-NMR (500 MHz, CD3OD) d (ppm) = 2.11 (3H, s, Ac), 3.55 (2H, s, Ph-CH2-), 7.21-7.49 (4H, m, Aromatic H)To a stirred solution of 2-(4-aminophenyl) acetic acid (2.0 g, 13.23 mmol) and TEA (3.66 mL, 26.5 mmol) in DCM (20 mL) at RT was added acetic anhydride (1.25 1 mL, 13.23 mmol) drop wise and the reaction mixture was stirred for 16 hours at RT. The reaction mixture was acidified, diluted with DCM (30 mL) and the organic layer was washed with water (10 mL) and brine (10 mL), dried over sodium sulphate, concentrated to obtain the title compound(1.2 g, 46 percent).To a stirred solution of 4-aminophenylacetic acid (31.5 g, 0.209 mol) in acetonitrile (550 ml) was added acetic anhydride (57 ml), sodium carbonate (66.5 g, 0.627 mol) and water (55 ml). The reaction was allowed to stir at room temperature for 3 hours. Reaction mixture was then poured onto a solution of conc. HCI (130 ml) and water (1200 ml). Reaction mixture was then extracted with EtOAc (2 x 750 ml). Combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure to reveal a tan solid. Purification by column chromatography [Si02 : 100percent DCM to 10percent MeOH/DCM] afforded a light tan solid (16. 5g, 41 percent).According to a reported procedure [49], 4-aminophenylaceticacid (4, 2.0 g) was added to acetic acid (20 mL) under microwave irradiation (150 °C) for 1 h. Thereaction mixture was poured into ethyl acetate then washed with water and then allowed to dry toyield the compound 8 (Scheme 9; 2.252 g; 100percent) as a white-grey solid. m.p. 166–168 °C [57]. 1H-NMR(300 MHz, DMSO-d6): δ = 9.92 (s, 1H), 7.51 (d, 3J = 8.6 Hz, 2H), 7.16 (d, 3J = 8.6 Hz, 2H), 3.49 (s, 1H), 2.03 (s, 3H). 13C-NMR (75 MHz, DMSO-d6): δ = 172.79 (Cq), 172.02 (Cq), 168.13 (Cq), 137.83 (Cq), 129.52(CH), 118.87 (CH), 40.11 (CH2), 23.87 (CH3). IR: 3348 (w), 1709 (s), 1638 (m), 1601 (s), 1542 (s), 1538 (s), 1221 (m), 1195 (m), 968 (w), 806 (w), 723 (w). 1H-NMR (400 MHz, CD3OD): δ 7.48 (d, J = 8.8 Hz, 2H), 7.21 (d, J = 8.8 Hz, 2H), 3.55 (s, 2H), 2.10 (s, 3H); HRMS (FAB+): [M + H]+ calcd. for C10H12O3N, 194.0817; found, 194.0770.mixing p-aminophenylacetic acid, N, N-dimethylacetamide and ammonium chloride, heating to 168 ° C, refluxing for 2 h, and then cooling to room temperature, Add ice water to 4 , insulation crystallization 50min, filtration, washing with ice water filter cake, adjust the temperature to 65 , vacuum drying 4.5h to be acetamidophenylacetic acid, of which p-aminophenylacetic acid, N, N-bis The weight ratio (g / ml) ratio of methylacetamide is 3:15, the weight ratio of p-aminophenylacetic acid and ammonium chloride is 3: 1.5, and the weight ratio of p-aminophenylacetic acid to ice water during crystallization is For 3: 8.

Chronic rheumatoid arthritis

Molecular Weight:193.20
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:193.07389321
Monoisotopic Mass:193.07389321
Topological Polar Surface Area:66.4
Heavy Atom Count:14
Complexity:219
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes