| US 7,491,718 B2 | ||
| Sulfonamides having antiangiogenic and anticancer activity | ||
| Kenneth M. Comess, Winnetka, Ill. (US); Scott A. Erickson, Zion, Ill. (US); Jack Henkin, Highland Park, Ill. (US); Douglas M. Kalvin, Buffalo Grove, Ill. (US); Megumi Kawai, Libertyville, Ill. (US); Ki H. Kim, Vista, Calif. (US); Nwe Y. BaMaung, Niles, Ill. (US); Chang Hoon Park, Libertyville, Ill. (US); George S. Sheppard, Wilmette, Ill. (US); Anil Vasudevan, Gurnee, Ill. (US); Jieyi Wang, Lake Bluff, Ill. (US); David M. Barnes, Lake Villa, Ill. (US); Steve D. Fidanze, Grayslake, Ill. (US); Lawrence Kolaczkowski, Gurnee, Ill. (US); Robert A. Mantei, Franklin, Wis. (US); David C. Park, Urbana, Ill. (US); William J. Sanders, Fox Lake, Ill. (US); Jason S. Tedrow, Evanston, Ill. (US); and Gary T. Wang, Libertyville, Ill. (US) | ||
| Assigned to Abbott Laboratories, Abbott Park, Ill. (US) | ||
| Filed on Oct. 08, 2003, as Appl. No. 10/681,784. | ||
| Claims priority of provisional application 60/416793, filed on Oct. 08, 2002. | ||
| Prior Publication US 2004/0167128 A1, Aug. 26, 2004 | ||
| Int. Cl. A61K 31/435 (2006.01); A61K 31/535 (2006.01); A61K 31/4965 (2006.01); A61K 31/415 (2006.01); A61K 31/40 (2006.01); A61K 31/425 (2006.01); C07D 265/30 (2006.01); C07D 241/04 (2006.01); C07D 279/12 (2006.01); C07D 277/02 (2006.01); C07D 263/02 (2006.01); C07C 255/03 (2006.01); A61K 31/42 (2006.01) | ||
| U.S. Cl. 514—227.8 | 3 Claims |
1. A compound of formula (III)
 R1 is selected from the group consisting of hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 alkoxy, RaRbN— and RaRbNalkoxy, wherein Ra and Rb are each independently selected from the group consisting of hydrogen and alkyl;
R2 is selected from the group consisting of alkoxy, alkoxyalkyl, C1-C10 alkyl, alkylsulfanyl, alkylsulfanylalkyl, alkylsulfonyl, alkylsulfonylalkyl, amino, aminoalkyl, cycloalkyl and (cycloalkyl)alkyl;
R3 is selected from the group consisting of hydrogen and alkyl;
R4 is selected from the group consisting of hydrogen, alkenyl, alkoxy, alkoxyalkyl, alkoxycarbonyl, alkyl, alkylcarbonyl, alkylsulfonyl,
alkylsulfanyl, alkylsulfanylalkyl, carboxy, cyano, cyanoalkyl, cycloalkyl, (cycloalkyl)alkyl, heteroaryl, heterocycle, heterocyclealkyl,
heterocyclealkenyl, hydroxy, hydroxyalkyl, nitro, phenyl, phenylsulfonyl, Rc4Rd4N—, Rc4Rd4Nalkyl, Rc4Rd4Nalkenyl, Rc4Rd4Nalkynyl, Rc4Rd4Nalkoxy, Rc4Rd4Nalkoxycarbonyl, Rc4Rd4Ncarbonyl, Rc4Rd4Ncycloalkyl, Rc4Rd4Nalkylcycloalkyl, Rc4Rd4N(cycloalkyl)alkyl, Rc4Rd4Nsulfinyl, Re4Rf4Nalkyl(Rc4)N—, Re4Rf4Nalkyl(Rc4)Ncarbonyl, Re4Rf4Nalkyl(Rc4)Ncarbonylalkenyl, Re4Rf4Nalkylcarbonyl(Rc4)N—, Re4Rf4Nalkoxycarbonyl(Rc4)N—, Rc4Rd4Nalkylsulfanyl, Rc4Rd4Nalkylsulfinyl, Rc4Rd4Nalkylsulfonyl, Rg4Rj4Nalkyl(Rc4)Ncarbonyl(Rc4)N—; wherein the phenyl group, the phenyl group of phenylsulfonyl, the heteroaryl, the heterocycle, the heterocycle of heterocyclealkyl,
the heterocycle of heterocyclealkenyl may be optionally substituted with 1, 2 or 3 substituents selected from the group consisting
of alkoxy, alkyl, cyano and nitro; and wherein Rc4, Rd4, Re4, Rf4, Rg4 and Rj4 are each independently selected from the group consisting of hydrogen, alkoxyalkyl, alkyl, alkylcarbonyl, aminoalkyl, cycloalkyl,
(cycloalkyl)alkyl, heterocycle and phenyl, or each individual pair of Rc4 and Rd4, or Re4 and Rf4, or Rg4 and Rj4 taken together with the nitrogen atom they are each attached form a heterocycle;
R5 is selected from the group consisting of alkyl, amino, aminoalkyl, aryl, arylalkenyl, arylalkyl, heteroaryl, heteroarylalkenyl,
heteroarylalkyl, heterocycle, heterocyclealkyl and heterocyclealkenyl, wherein aryl, the aryl group of arylalkenyl, the aryl
group of arylalkyl, the heteroaryl, the heteroaryl of heteroarylalkenyl, the heteroaryl of heteroarylalkyl, and the heterocycle
of R5 may be optionally substituted with 1, 2 or 3 substituents independently selected from the group consisting of alkenyl, alkoxy,
alkoxycarbonyl, alkyl, alkylcarbonyl, alkylsulfonyl, aminoalkyl, phenyl, phenylsulfonyl, carboxy, cyano, cyanoalkyl, heteroaryl,
heterocycle, heterocyclealkyl, heterocyclealkenyl, hydroxy, nitro, Rc5Rd5N—, Rc5Rd5Nalkyl, Rc5Rd5Nalkenyl, Rc5Rd5Nalkynyl, Rc5Rd5Nalkoxy, Rc5Rd5Nalkoxycarbonyl, Rc5Rd5Ncarbonyl, Rc5Rd5Ncycloalkyl, Rc5Rd5Nalkylcycloalkyl, Rc5Rd5Ncycloalkylalkyl, Rc5Rd5Nsulfinyl, Re5Rf5Nalkyl(Rc5)N—, Re5Rf5Nalkyl(Rc5)Ncarbonyl, Re5Rf5Nalkyl(Re5)Ncarbonylalkenyl, Re5Rf5Nalkylcarbonyl(Rc5)N—, Re5Rf5Nalkoxycarbonyl(Rc5)N—, Rc5Rd5Nalkylsulfanyl, Rc5Rd5Nalkylsulfinyl, Rc5Rd5Nalkylsulfonyl, Rg5Rj5Nalkyl(Re5)Ncarbonyl(Rc5)N—; wherein the phenyl group, the phenyl group of phenylsulfonyl, the heteroaryl, the heterocycle, the heterocycle of heterocyclealkyl,
the heterocycle of heterocyclealkenyl may be optionally substituted with 1, 2 or 3 substituents selected from the group consisting
of alkoxy, alkyl, cyano, and nitro; and wherein Rc5, Rd5, Re5, Rf5, Rg5 and Rj5 are each independently selected from the group consisting of hydrogen, alkoxyalkyl, alkyl, alkylcarbonyl, aminoalkyl, cycloalkyl,
(cycloalkyl)alkyl, heterocycle and phenyl; and
R6 is selected from the group consisting of hydrogen, alkyl, alkylsulfanylalkyl, aryl, and arylalkyl.
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