Common name: Imatinib; STI 571; STI-571; CGP54148B; CGP-57148B; Gleevec; Glivec; Imatinib Methansulfonate
Trademarks: Celonib; Enliven; Gleevec; Glivec; Imatib; Mesylonib; Mitinab; Plivatinib; Shantinib
Molecular Formula: C29H31N7O
CAS Registry Number: 152459-95-5; 220127-57-1 (mesilate)
CAS Name: 4-[(4-methylpiperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide
Molecular Weight: 493.603
SMILES:CN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC1
InChI Key: KTUFNOKKBVMGRW-UHFFFAOYSA-N
InChI: InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
Activity: Tyrosine Kinase Inhibitor; Protein Kinase Inhibitor; BCR-Abl Kinase Inhibitor; Gastrointestinal Stromal Tumours Therapy; Oncolytic Drugs; Chronic Myelogenous Leukemia Therapy; GIST Therapy; CML Therapy; Antineoplastic Agents
Status: Launched 2001
Originator: Novartis
Imatinib synthesis: WO2006071130A2
Imatinib synthesis: EP0564409 (example 21) also see WO2004074502A2
Imatinib synthesis: WO2003066613A1 (Route 1)
Imatinib synthesis: WO2003066613A1 (Route 2)
Orange book says for Imatinib
US6958335 Approved (2002-06-19) Expires (2022-06-19)
US5521184 (1995-01-04) (2015-01-04)
References:
1. Szczepek, W.; et. al. Process for preparation of imatinib base. WO2006071130A2
2. Zimmermann, J. Dr.; Pyrimidin derivatives and process for their preparation. EP0564409 A1
3. Kankan, R. N.; et. al. A process of preparing imatinib. WO2004074502A2
4. Loiseleur, O.; et. al. N-phenyl-2-pyrimidine-amine derivatives. WO2003066613A1
5. Moen, M. D.; et. al. Imatinib: a review of its use in chronic myeloid leukaemia. Drugs 2007, 67(2), 299-320. (activity)
6. Savage, D. G.; et. al. Imatinib Mesylate-A New Oral Targeted Therapy. N Engl J Med 2002, 346, 683-693. (activity)
7. Essat, M.; et. al. Imatinib as adjuvant therapy for gastrointestinal stromal tumors: a systematic review. Int. J. Cancer 2011, 128, 2202–2214. (activity)
