Beloranib，CKD-732, -Drug Synthesis Database

【结构式】

【药物名称】Beloranib，CKD-732

【化学名称】3-[4-[2-(Dimethylamino)ethoxy]phenyl]-2(E)-propenoic acid (3R,4S,5S,6R)-4-[2(R)-methyl-3(R)-(3-methyl-2-butenyl)oxiran-2-yl]-5-methoxy-1-oxaspiro[2.5]oct-6-yl ester
　　　　　　6-O-[3-[4-[2-(Dimethylamino)ethoxy]phenyl]-2(E)-propenoyl]fumagillol

【CA登记号】251111-30-5

【分子式】C₂₉H₄₁NO₆

【分子量】499.65322

【开发单位】Chong Kun Dang Pharm. (Originator)

【药理作用】ONCOLYTIC DRUGS, Angiogenesis Inhibitors

合成路线1 合成路线2

合成路线1

4-(2-Dimethylaminoethoxy)cinnamic acid (I) was converted to acid chloride (II) upon treatment with thionyl chloride in refluxing benzene. This was then coupled with the sodium alkoxide of fumagillol (III) in THF to furnish the title compound.

参考文献中间体

【1】 Chun, H.S.; Choi, N.S.; Lee, S.J.; Han, C.K.; Hong, C.I.; Hong, R.K.; Kim, J.W.; Moon, S.K.; Ahn, S.K. (Chong Kun Dang Corp.); Fumagillol derivs. and processes for preparing the same. US 6063812; WO 9959986 .
【1】 Kim, J.W., Ahn, S.K., Hong, R.K. et al. (Chong Kun Dang Holdings Corp.) Fumagillol derivatives and processes for preparing the same. CA 2331873, EP 1077964, JP 2002515497, US 6063812, WO 1999059986.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	48095	(E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]-2-propenoic acid	C₁₃H₁₇NO₃	详情	详情
(I)	13712	(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]octan-6-ol	C₁₆H₂₆O₄	详情	详情
(II)	48096	(E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]-2-propenoyl chloride	C₁₃H₁₆ClNO₂	详情	详情
(II)	48096	(E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]-2-propenoyl chloride	C₁₃H₁₆ClNO₂	详情	详情
(III)	13712	(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]octan-6-ol	C₁₆H₂₆O₄	详情	详情
(III)	48095	(E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]-2-propenoic acid	C₁₃H₁₇NO₃	详情	详情

合成路线2

Beloranib hemioxalate can be prepared by condensation of the sodium alkoxide of fumagillol (I) with 4-(2-dimethylaminoethoxy)cinnamic acid chloride (II) in THF.
Acide chloride (II) is obtained by treatment of 4-(2-dimethyl-aminoethoxy)cinnamic acid (III) with thionyl chloride in refluxing benzene .

参考文献中间体

【1】 Chun, H.S.; Choi, N.S.; Lee, S.J.; Han, C.K.; Hong, C.I.; Hong, R.K.; Kim, J.W.; Moon, S.K.; Ahn, S.K. (Chong Kun Dang Corp.); Fumagillol derivs. and processes for preparing the same. US 6063812; WO 9959986 .
【1】 Kim, J.W., Ahn, S.K., Hong, R.K. et al. (Chong Kun Dang Holdings Corp.) Fumagillol derivatives and processes for preparing the same. CA 2331873, EP 1077964, JP 2002515497, US 6063812, WO 1999059986.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	48095	(E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]-2-propenoic acid	C₁₃H₁₇NO₃	详情	详情
(I)	13712	(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]octan-6-ol	C₁₆H₂₆O₄	详情	详情
(II)	48096	(E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]-2-propenoyl chloride	C₁₃H₁₆ClNO₂	详情	详情
(II)	48096	(E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]-2-propenoyl chloride	C₁₃H₁₆ClNO₂	详情	详情
(III)	13712	(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]octan-6-ol	C₁₆H₂₆O₄	详情	详情
(III)	48095	(E)-3-[4-[2-(dimethylamino)ethoxy]phenyl]-2-propenoic acid	C₁₃H₁₇NO₃	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)