	US 7,517,876 B2
	Anti-infective agents
Larry L. Klein, Lake Forest, Ill. (US); Peggy P. Huang, Lake Bluff, Ill. (US); John T. Randolph, Libertyville, Ill. (US); Douglas K. Hutchinson, Antioch, Ill. (US); Ming C. Yeung, Grayslake, Ill. (US); and Charles A. Flentge, Salem, Wis. (US)
Assigned to Abbott Laboratories, Abbott Park, Ill. (US)
Filed on Feb. 27, 2006, as Appl. No. 11/363,377.
Claims priority of provisional application 60/656767, filed on Feb. 25, 2005.
Prior Publication US 2006/0287300 A1, Dec. 21, 2006
Int. Cl. C07D 285/26 (2006.01); A61K 31/549 (2006.01)

U.S. Cl. 514—223.2 [544/12]

19 Claims

1. A compound, a stereoisomer of the compound, a tautomer of the compound, a pharmaceutically acceptable salt of the compound, stereoisomer, or tautomer, or a combination thereof, wherein:

the compound corresponds to formula (I):

A is phenyl;

R¹is selected fro the group consisting of —OR_A, —O-alkyl-C(O)Y, —NR_AR_B, —N(R_C)(—N(R_C)(R_A)), —N(R_B)L¹(O)Y, and —N(R_B)S(O)₂Z;

X at each occurrence, is independently selected from the group consisting of R_A, —OR_Aand —NR_AR_B;

L¹is selected from the group consisting of a bond or lower alkyl;

Y is selected from the group consisting of R_A, —OR_A, —NR_AR_B, —O-alkyl-OR_A, —O-alkyl-NR_AR_B, —N(R_C)-alkyl-NR_AR_B, —(CR³R⁴)—N(R_C)C(O)X; —(CR³R⁴)—NR_AR_B, and heterocycle;

Z is selected from the group consisting of R_A, —OR_A, —NR_AR_B, -alkyl-OR_A, -alkyl-NR_AR_B, -alkyl-N(R_C)C(O)X, -alkyl-O-alkyl-OR_A, -alkyl-O-alkyl-NR_AR_Band -alkyl-N(R_C)-alkyl-NR_AR_B;

R³and R⁴are independently selected from the group consisting of hydrogen, alkyl, alkenyl and arylalkyl wherein:

the aryl moiety of the arylalkyl is substituted with 0, 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of alkyl, alkenyl, alkynyl, formyl, halo, nitro, cyano, alkoxy, —OH, —OC(O)(alkyl), —SH, —S(alkyl), —S(O)alkyl, —S(O)₂(alkyl), —NH₂, —N(H)(alkyl), —N(alkyl)₂, —C(O)alkyl, —C(O)OH, —C(O)(—Oalkyl), —C(O)NH₂, —C(O)N(H)(alkyl), —C(O)N(alkyl)₂and haloalkyl;

R_Aat each occurrence is independently selected from the group consisting of hydrogen, alkyl, alkenyl, haloalkyl, haloalkenyl, R_aand -alkylR_a;

R_Bat each occurrence is independently selected from the group consisting of hydrogen, alkyl, haloalkyl, R_a, -alkylR_a, —OH, alkoxy, hydroxyalkyl, alkoxyalkyl, —OR_a, and —O-alkylR_a;

R_Cat each occurrence is independently selected from the group consisting of hydrogen and lower alkyl;

R_aat each occurrence is independently selected from the group consisting of cycloalkyl, cycloalkenyl, heterocycle, aryl and heteroaryl, wherein:

each such substituent is substituted with 0, 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of alkyl, alkenyl, alkynyl, formyl, halo, nitro, cyano, alkoxy, —OH, —O-alkyl-R_b, —OC(O)(alkyl), —SH, —S(alkyl), —S(O)alkyl, —S(O)₂(alkyl), —NH₂, —N(H)(alkyl), —N(alkyl)₂, —C(O)alkyl, —C(O)OH, —C(O)(—Oalkyl), —C(O)NH₂, —C(O)N(H)(alkyl), —C(O)N(alkyl)₂, haloalkyl, R_band -alkyl-R_b;

R_bat each occurrence is independently selected from the group consisting of cycloalkyl, cycloalkenyl, heterocycle, aryl and heteroaryl, wherein:

each such substituent is substituted with 0, 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of alkyl, alkenyl, alkynyl, formyl, halo, nitro, cyano, alkoxy, —OH, —OC(O)(alkyl), —SH, —S(alkyl), —S(O)alkyl, —S(O)₂(alkyl), —NH₂, —N(H)(alkyl), —N(alkyl)₂, —C(O)alkyl, —C(O)OH, —C(O)(—Oalkyl), —C(O)NH₂, —C(O)N(H)(alkyl), —C(O)N(alkyl)₂and haloalkyl;

R²is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, R_a, -alkyl-R_a, -alkenyl-R_a, -alkynyl-R_a, haloalkyl, hydroxyalkyl, formylalkyl, cyanoalkyl, -alkyl-OR_A, and -alkyl-NR_AR_B;

R⁵, R⁶, R⁷, and R⁸are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cyano, formyl, halo, nitro, —OR_A, —OC(O)R_A, —OC(O)OR_A, —OC(O)NR_AR_B, —OS(O)₂R_A, —SR_A, —S(O)R_A, —S(O)₂R_A, —S(O)₂(OR_A), —S(O)₂NR_AR_B, —NR_AR_B, —N(R_C)C(O)R_A, —N(R_C)C(O)NR_AR_B, —N(R_C)C(O)OR_A, —N(R_C)S(O)₂R_A, —N(R_C)S(O)₂NR_AR_B, —N(R_C)S(O)₂N(R_C)C(O)OR_A, —C(O)R_A, —C(O)OR_A, —C(O)NR_AR_B, haloalkyl, cyanoalkyl, -alkylOR_A, -alkyl-OC(O)R_A, -alkyl-OC(O)OR_A, -alkyl-OC(O)NR_AR_B, -alkyl-OS(O)₂R_A, -alkyl-SR_A, -alkyl-S(O)R_A, -alkyl-S(O)₂R_A, -alkyl-S(O)₂(OR_A), -alkyl-S(O)₂NR_AR_B, -alkyl-NR_AR_B, -alkyl-N(R_C)C(O)R_A, -alkyl-N(R_C)C(O)NR_AR_B, -alkyl-N(R_C)C(O)OR_A, -alkyl-N(R_C)S(O)₂R_A, -alkyl-N(R_C)S(O)₂NR_AR_B, -alkyl-N(R_C)S(O)₂N(R_C)C(O)OR_A, -alkyl-C(O)R_A, -alkyl-C(O)(OR_A) and -alkyl-C(O)NR_AR_B;

R⁹is selected from the group consisting of —OR_A, —SR_A, —NR_AR_B, —N(R_C)C(O)R_A, —N(R_C)C(O)OR_A, —N(R_C)S(O)₂R_A, and —N(R_C)S(O)₂NR_AR_B;

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

R¹⁰at each occurrence is independently selected from the group consisting of alkyl, alkenyl, alkynyl, cyano, formyl, nitro, halo, R_a, —OR_A, —OC(O)X, —OS(O)₂R_A, —O-alkyl-G¹, —SR_A, —S(O)R_A, —S(O)₂X, —NR_AR_B, —N(R_B)C(O)X, —N(R_B)C(O)(-alkyl-G¹), —N(R_B)S(O)₂X, —N(R_B)S(O)₂(-alkyl-G¹), —C(O)X, —C(O)N(R_B)(-alkyl-G¹), haloalkyl, cyanoalkyl, nitroalkyl, -alkyl-R_a, —N(-alkyl-C(O)X)(S(O)₂X,) and -alkyl-G¹;

G¹at each occurence is independently selected from the group consisting of —OR_A, —NR_AR_B, —N(R_C)(—NR_AR_B), —N(R_C)S(O)₂X, —N(R_C)C(O)X, —C(O)X, —OC(O)X, and —S(O)₂X; and

R¹¹is selected from the group consisting of hydrogen, alkyl, alkenyl and arylalkyl, wherein:

the aryl moiety of the arylalkyl is substituted with 0, 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of

alkyl, alkenyl, alkynyl, formyl, halo, nitro, cyano, haloalkyl, —OH, alkoxy, —OC(O)(alkyl), —NH₂, —N(H)(alkyl), —N(alkyl)₂, —C(O)OH, —C(O)(—Oalkyl), —C(O)alkyl, —C(O)NH₂, —C(O)N(H)(alkyl), and —C(O)N(alkyl)₂.