	US 7,514,410 B2
	Hepatitis C therapies
Yarlagadda S. Babu, Birmingham, Ala. (US); Pooran Chand, Birmingham, Ala. (US); Minwan Wu, Vestavia Hills, Ala. (US); Pravin L. Kotian, Hoover, Ala. (US); V. Satish Kumar, Birmingham, Ala. (US); Tsu-Hsing Lin, Vestavia Hills, Ala. (US); Yahya El-Kattan, Vestavia Hills, Ala. (US); and Ajit K. Ghosh, Birmingham, Ala. (US)
Assigned to BioCryst Pharmaceuticals, Inc., Birmingham, Ala. (US)
Filed on Mar. 23, 2006, as Appl. No. 11/388,060.
Claims priority of provisional application 60/665832, filed on Mar. 29, 2005.
Claims priority of provisional application 60/692572, filed on Jun. 22, 2005.
Prior Publication US 2006/0234963 A1, Oct. 19, 2006
Int. Cl. A01N 43/04 (2006.01)

U.S. Cl. 514—23 [536/29.2]

42 Claims

1. A compound of the formula:

wherein:

R is NR_eR_f, NR_aNR_bR_c, alkyl, alkenyl, alkynyl, aryl, (CH₂)_nNR_aR_b, (CH₂)_nOR_a, C(═NR_a)NR_bR_c, (CH₂)_n—CH(NHR_a)CO₂R_b, (CH₂)_n—S-alkyl, (CH₂)_n—S-aryl, Cl, F, Br, I, CN, COOR_a, CONR_aR_b, NHC(═NR_a)NHR_b, NR_aOR_b, NR_aNO, NHCONHR_a, NR_aN═NR_b, NR_aN═CHR_b, NR_aC(O)NR_bR_c, NR_aC(S)NR_bR_c, NR_aC(O)OR_b, CH═N—OR_a, NR_aC(═NH)NR_bR_c, NR_aC(O)NR_bNR_cR_d, O—C(O)R_a, OC(O)—OR_a, ONH—C(O)O-alkyl, ONHC(O)O-aryl, ONR_aR_b, SNR_aR_b, S—ONR_aR_b, or SO₂NR_aR_b;

n is 0, 1, 2, 3, 4, or 5;

R¹is H, NR_aR_b, Cl, F, OR_a, SR_a, NHCOR_a, NHSO₂R_a, NHCONHR_a, CN, alkyl, aryl, ONR_aR_b, or NR_aC(O)OR_b;

R²is H and R³is OH; or R²is OH and R³is H;

R⁴is OH, alkyl-O—, alkylC(═O)O, alkyl-S—, or alkylC(═O)—S—;

R⁵is OH, alkyl-O—, alkylC(═O)O, alkyl-S—, or alkylC(═O)—S—

R_a, R_b, R_c, and R_dare independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, acyl, SO₂-alkyl and NO; or R_aand R_btogether with the nitrogen to which they are attached form a pyrrolidino, piperidino, piperazino, azetidino, morpholino, pyrrolino, or thiomorpholino ring; or R_band R_ctogether with the nitrogen to which they are attached form a pyrrolidino, piperidino, piperazino, azetidino, morpholino, pyrrolino, or thiomorpholino ring;

R_eis alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, acyl, SO₂-alkyl or NO; and R_fis H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, acyl, SO₂-alkyl and NO; or R_eand R_ftogether with the nitrogen to which they are attached form a pyrrolidino, piperidino, piperazino, azetidino, morpholino, pyrrolino, or thiomorpholino ring; which ring is optionally substituted with one or more halo, hydroxyl, alkyl, alkenyl, or alkynyl;

wherein any alkyl, cycloalkyl, alkenyl, alkynyl, or acyl is optionally substituted with 1 to 3 substituents selected from the group consisting of alkoxy, acyl, acylamino, acyloxy, oxyacyl, amino, substituted amino, aminoacyl, aryl, aryloxy, cyano, halogen, hydroxyl, nitro, N₃, carboxyl, carboxyl esters, thiol, thioalkyl, thioaryl, thioheteroaryl, thiocycloalkyl, thioheterocyclic, cycloalkyl, heteroaryl, and heterocyclic;

and wherein any aryl, heteroaryl, or heterocycle is optionally substituted with 1 to 3 substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, acyl, acylamino, acyloxy, oxyacyl, amino, substituted amino, aminoacyl, aryl, aryloxy, cyano, halogen, hydroxyl, nitro, N₃, carboxyl, carboxyl esters, thiol, thioalkyl, thioaryl, thioheteroaryl, thiocycloalkyl, thioheterocyclic, cycloalkyl, heteroaryl, and heterocyclic;

or a pharmaceutically acceptable salt or prodrug thereof.