Atiprimod

Atiprimod

File:Atiprimod.svg
Systematic (IUPAC) name
3-(8,8-dipropyl-3-azaspiro[4.5]decan-3-yl)-N,N- diethylpropan-1-amine
Identifiers
CAS Number	123018-47-3
ATC code	none
PubChem	CID 129869
ChemSpider	114962
Chemical data
Formula	C22H44N2
Molar mass	336.598 g/mol[[]]

Atiprimod (INN, codenamed SK&F106615; also known as azaspirane, although this more properly refers to the class of chemicals to which atiprimod belongs) is a substance being studied in the treatment of certain multiple myelomas and other advanced cancers. Atiprimod may block the growth of tumors and the growth of blood vessels from surrounding tissue to the tumor. Atiprimod is a type of signal transduction inhibitor. It was first developed by SmithKline Beecham (now part of GlaxoSmithKline) as a potential treatment for rheumatoid arthritis.

January 7, 2008 Callisto Pharmaceuticals, Inc. announced that it has restructured its license agreement with Genzyme Corporation for Atiprimod. In August 2002, Callisto’s wholly owned subsidiary, Synergy, acquired from AnorMED Inc. worldwide exclusive rights to develop, manufacture and commercialize Atiprimod. AnorMED was acquired by Genzyme in November 2006.

The restructured agreement eliminates all milestone payments and reduces royalties owed to Genzyme to single digits. In return for the reduced future payments to Genzyme, Callisto is paying an upfront fee in 2008

Synergy Pharmaceuticals, Inc. (a wholly-owned subsidiary of Callisto) entered into a license agreement with AnorMED Inc. to license Atiprimod from AnorMED. Atiprimod is a macrophage-targeting oral cytokine inhibitor which is being developed by AnorMED as a potential treatment for rheumatoid arthritis and other autoimmune diseases. Phase I trials have been successfully completed and Phase II multicenter trials have been approved by the FDA. The compound was discovered in a joint research and development program with SmithKline and French (now SmithKline Beecham, SB) but following acceptance of the Phase II protocol by the FDA, SB decided not to proceed with further development of atiprimod as a result of an internal restructuring program. All rights to atiprimod and other azaspiranes developed in this program have reverted to AnorMED. The compound was originally disclosed in European patent, EP-00310321, entitled 'Preparation of N-aminoalkyl-2-azaspiro[4.5]decanes and analogs as immunosuppressants', while a cost-effective, efficacious pilot plant synthesis has also been described.

Synthesis

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Dagger, R. E.; Grady, C. W.; 1999, U.S. Patent 5,952,365.

Further reading

• Full text at PMC: 1895034

External links

• Atiprimod entry in the public domain NCI Dictionary of Cancer Terms

 This article incorporates public domain material from the U.S. National Cancer Institute document "Dictionary of Cancer Terms".