TIPIFARNIB, типифарниб , تيبيفارنيب , 替匹法尼 ,

TIPIFARNIB
R-115777, NSC-702818
Categories

• Antineoplastic Agents
• P-glycoprotein/ABCB1 Inhibitors
• Quinolines

UNIIMAT637500A
CAS number 192185-72-1 +form
192185-68-5 (racemate)
192185-69-6 (racemic; fumarate)
192185-70-9 (racemic; diHCl)
(+)-(R)-6-[1-Amino-1-(4-chlorophenyl)-1-(1-methylimidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2(1H)-one

2(1H)-Quinolinone, 6-[(R)-amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-

Weight Average: 489.396
Chemical Formula C₂₇H₂₂Cl₂N₄O

типифарниб [Russian] [INN]

تيبيفارنيب [Arabic] [INN]

替匹法尼 [Chinese] [INN]

(R)-(+)-R115777

(R)-6-(Amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone

(R)-6-(amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methylquinolin-2(1H)-one

2 (1H))-Quinolinone,6-(amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl)-4-(3-chlorophenyl)-1-methyl-, 2(1H )-quinolinone

 

Title: Tipifarnib

CAS Registry Number: 192185-72-1; 192185-68-5 (unspecified stereo)

CAS Name: 6-[(R)-Amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone

Manufacturers' Codes: R-115777

Trademarks: Zarnestra (Janssen)

Molecular Formula: C27H22Cl2N4O

Molecular Weight: 489.40

Percent Composition: C 66.26%, H 4.53%, Cl 14.49%, N 11.45%, O 3.27%

Literature References: Farnesyl transferase inhibitor. Prepn: M. G. Venet et al., WO 9721701; eidem, US 6037350 (1997, 2000 both to Janssen). Review of syntheses: P. R. Angibaud et al., Eur. J. Org. Chem. 2004, 479-486. Inhibition of farnesyl protein transferase and antitumor effects in vivo: D. W. End et al., Cancer Res. 61, 131 (2001). Clinical pharmacology and pharmacokinetics: J. Zujewski et al., J. Clin. Oncol. 18, 927 (2000). Accelerator mass spec determn in biological samples: R. C. Garner et al., Drug Metab. Dispos. 30, 823 (2002). Clinical evaluation in hematologic malignancies: J. Cortes et al., Blood 101, 1692 (2003). Review of clinical experience: P. Norman, Curr. Opin. Invest. Drugs 3, 313-319 (2002).

Properties: Crystals from 2-propanol, mp 234°. [a]D20 +22.86° (c = 0.98 in methanol).

Melting point: mp 234°

Optical Rotation: [a]D20 +22.86° (c = 0.98 in methanol)

Therap-Cat: Antineoplastic.

Keywords: Antineoplastic; Farnesyl Transferase Inhibitors.

NMR SIMULATION

PREDICTED VALUES

1H NMR: δ 3.42 (3H, s), 3.63 (3H, s), 6.57 (1H, s), 6.67 (1H, d, J = 1.7 Hz), 7.27 (1H, dd, J = 8.3, 1.5 Hz), 7.36-7.59 (8H, 7.46 (ddd, J = 8.3, 1.5, 0.5 Hz), 7.41 (ddd, J = 8.1, 8.1, 0.5 Hz), 7.39 (ddd, J = 8.1, 1.6, 1.5 Hz), 7.49 (ddd, J = 8.1, 1.7, 1.5 Hz), 7.55 (ddd, J = 8.3, 1.6, 0.5 Hz), 7.58 (d, J = 1.7 Hz)), 7.66 (1H, dd, J = 8.3, 0.5 Hz), 7.71 (1H, dd, J = 1.5, 0.5 Hz), 7.84 (1H, ddd, J = 1.7, 1.6, 0.5 Hz).

13C NMR PREDICT

COSY PREDICT

HSQC PREDICT

See SYNTHESIS

 https://newdrugapprovals.org/2018/06/21/tipifarnib-%D1%82%D0%B8%D0%BF%D0%B8%D1%84%D0%B0%D1%80%D0%BD%D0%B8%D0%B1-%D8%AA%D9%8A%D8%A8%D9%8A%D9%81%D8%A7%D8%B1%D9%86%D9%8A%D8%A8-%E6%9B%BF%E5%8C%B9%E6%B3%95%E5%B0%BC/