US 7,524,956 B2
Hemisynthetic method and new compounds
Carmen Cuevas, Madrid (Spain); Marta Perez, Madrid (Spain); Andres Francesch, Madrid (Spain); Carolina Fernandez, Madrid (Spain); Jose Luis Chicharro, Madrid (Spain); Pilar Gallego, Madrid (Spain); Maria Zarzuelo, Madrid (Spain); Fernando de Calle, Madrid (Spain); and Ignacio Manzanares, Madrid (Spain)
Assigned to Pharma Mar, S.A., Madrid (Spain)
Filed on Jul. 09, 2007, as Appl. No. 11/774,890.
Application 11/774890 is a continuation of application No. 09/979404, granted, now 7,241,892, previously published as PCT/GB00/01852, filed on May 15, 2000.
Claims priority of application No. 9911345.8 (GB), filed on May 14, 1999; application No. 99818178.6 (GB), filed on Aug. 02, 1999; application No. 9923632.5 (GB), filed on Oct. 06, 1999; and application No. 0001063.7 (GB), filed on Jan. 17, 2000.
Prior Publication US 2008/0045713 A1, Feb. 21, 2008
Int. Cl. C07D 471/22 (2006.01); C07D 487/22 (2006.01); A61K 31/496 (2006.01)
U.S. Cl. 544—338  [544/342] 6 Claims
 
1. The compound of formula

OG Complex Work Unit Drawing
where R1 is:
(i) an unsubstituted aminomethylene group; or
(ii) an aminomethylene group, wherein the amino portion of the aminomethylene group is protected with a protecting group selected from alkyl, alkenyl, alkylsilylalkoxyalkyl, alkoxyalkyl, cyanoalkyl, alkoxyarylalkyl, cycloalkyl, nitroaryl, arylalkyl, and hydroxyarylalkyl; or
(iii) an N-acylated aminomethylene group, wherein the acyl portion of the N-acylated aminomethylene group is aroyl, arylaroyl, haloaroyl, nitroaroyl, or an acyl group of the formula —CO—Ra where Ra is selected from alkyl, alkoxy, alkenyl, arylalkyl, arylalkenyl, aminoacid, and heterocyclyl, each of which is optionally substituted with halo, cyano, nitro, carboxyalkyl, alkoxy, aryl, aryloxy, heterocyclyl, heterocyclyloxy, alkyl, amino or substituted amino; and
R18 is an OH group protected in the form of an alkyl ether, an alkoxyalkyl ether, an aryloxyalkyl ether, an alkoxyalkoxyalkyl ether, an alkylsilylalkoxyalkyl ether, an alkylthioalkyl ether, an arylthioalkyl ether, an azidoalkyl ether, a cyanoalkyl ether, a chloroalkyl ether, a heterocyclic ether, a cycloalkylalky ether, an alkenyl ether, a cycloalkyl ether, an alkylarylalkyl ether, an alkoxyarylalkyl ether, a nitroarylalkyl ether, a haloarylalkyl ether, an alkylaminocarbonylarylalkyl ether, an alkylsulfinylarylalkyl ether, or an alkylsilyl ether.