Process for preparing temozolomide

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

07612202

ABSTRACT:
The present invention provides a process for preparing highly pure Temozolomide base which includes recovery from the purification mother liquors by using an anionic exchange resin. By treating Temozolomide hydrochloride with a mixture of an organic acid, a water miscible organic solvent, and water, Temozolomide free base is obtained in an acidic medium. Due to the high sensitivity of Temozolomide to basic pH values the recovery-including process is especially advantageous because it enables obtaining high yields of highly pure Temozolomide base in acidic conditions.The process for producing Temozolomide base includes hydrolysis of the starting material 8-cyano-3-methyl-[3H]-imidazo[5,1-d]-tetrazin-4-one in acidic medium to obtain highly pure Temozolomide hydrochloride in high yield.

REFERENCES:
patent: 5260291 (1993-11-01), Lunt et al.
patent: 6844434 (2005-01-01), Kuo
patent: 2002/0095036 (2002-07-01), Kuo et al.
patent: 2005/0187206 (2005-08-01), Adin et al.
patent: WO 2005/063757 (2005-07-01), None
LanXess Engineering Chemistry, Lewatit Resin, Lewatit Mono Plus MP 64,Production Information, pp. 1-4, 2007.
Remco Engineering Ion Exchange Chemistry and Operation, 1-11, 2008.
Wang et al., J. Org. Chem. 62(21), 7288-7294, 1997.
Wang et al. “Alternative Syntheses of the Antitumour Drug Temozolomide Avoiding the Use of Methyl Isocyanate”, Journal of the Chemical Society, Chemical Communication, p. 1687-1688, 1994.
Clark et al. “Antitumor Imidazotetrazines. 32. Synthesis of Novel Imidazotetrazinones and Related Bicyclic Heterocycles to Probe the Mode of Action of the Antitumor Drug Temozolomide”, Journal of Medicinal Chemistry, 38(9): 1493-1504, 1995.
Stevens et al. “Antitumor Imidazotetrazines. 1. Synthesis and Chemistry of 8-Carbamoyl-3-(2-Chloroethyl)Imidazo[5,1-D]-1,2,3,5-Tetrazin-4(3H)-One, A Novel Broad-Spectrum Antitumor Agent”, Journal of Medicinal Chemistry, 27(2): 196-201, 1984.
Baig et al. “Antitumour Imidazotetrazines. Part 12. Reactions of Mitozolomide and Its 3-Alkyl Congeners With Oxygen, Nitrogen, Halogen, and Carbon Nucleophiles”, J. Chem. Soc. Perkin Trans., I: 675-670, 1987.
Newlands et al. “Temozolomide: A Review of Its Discovery, Chemical Properties, Pre-Clinical Development and Clinical Trials”, Cancer Treatment Reviews, 23: 35-61, 1997.
Brown et al. “Antitumor Imidazotetrazines. 40. Radiosyntheses of [4-11C-Carbonyl]- and [3-N-11C-Methyl]-8-Carbamoyl-3-Methylimidazo[5,1-D]-1,2,3,5-Tetrazin-4(3H)-One (Temozolomide) for Positron Emission Tomography (PET) Studies”, Journal of Medicinal Chemistry, 45(25): 5448-5457, 2002.
Wang et al., “Preparation and Thermostability of Polymorphs of Temozolomide,”Chinese Journal of Pharmaceuticals, vol. 34(4), pp. 178-180 (2003). abstract.
Wanner et al., “A new synthesis of temozolomide,”J. Chem. Soc. Perkins Trans I,pp. 1877-1880 (2002).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for preparing temozolomide does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for preparing temozolomide, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing temozolomide will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4084290

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.