US 7,320,972 B2
4-Biarylyl-1-phenylazetidin-2-ones
Eduardo Martinez, New York, N.Y. (US); John J. Talley, Somerville, Mass. (US); Stephen Antonelli, Lynn, Mass. (US); Timothy C. Barden, Salem, Mass. (US); Regina Lundrigan-Soucy, Charlestown, Mass. (US); Wayne C. Schairer, Westboro, Mass. (US); Jing-Jing Yang, Boxborough, Mass. (US); Daniel P. Zimmer, Somerville, Mass. (US); Brian Cali, Arlington, Mass. (US); Mark G. Currie, Sterling, Mass. (US); and Peter S. Yorgey, Cambridge, Mass. (US)
Assigned to Microbia, Inc., Cambridge, Mass. (US)
Filed on Nov. 10, 2004, as Appl. No. 10/986,570.
Claims priority of provisional application 60/614005, filed on Sep. 28, 2004.
Claims priority of provisional application 60/592529, filed on Jul. 30, 2004.
Claims priority of provisional application 60/549577, filed on Mar. 03, 2004.
Claims priority of provisional application 60/518698, filed on Nov. 10, 2003.
Prior Publication US 2005/0209165 A1, Sep. 22, 2005
Int. Cl. C07D 205/08 (2006.01); A61K 31/397 (2006.01); A61K 31/7052 (2006.01); A61P 3/06 (2006.01); A61P 9/10 (2006.01)
U.S. Cl. 514—210.02  [540/200] 71 Claims
 
1. A compound of formula:

OG Complex Work Unit Drawing
wherein

OG Complex Work Unit Drawing
represents an aryl or heteroaryl residue;
Ar represents an aryl residue;
R1 represents one, two, three, four or five residues chosen independently from H, halogen, —OH, loweralkyl, OCF2H, OCF3, CF2H, CH2F, —O-loweralkyl, methylenedioxy, ethylenedioxy, hydroxyloweralkyl, —CN, CF3, nitro, —SH, —S-loweralkyl, amino, alkylamino, dialkylamino, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfonyl, arylsulfonyl, acyl, carboxy, alkoxycarbonyl, carboxyalkyl, carboxamido, alkylsulfoxide, acylamino, amidino, phenyl, benzyl, phenoxy, benzyloxy, —PO3H2, —SO3H, and —B(OH)2,
R2 represents one, two, three, four or five residues chosen independently from H, halogen, —OH, loweralkyl, OCF2H, OCF3, CF2H, CH2F, —O-loweralkyl, methylenedioxy, ethylenedioxy, hydroxyloweralkyl, —CN, CF3, nitro, —SH, —S-loweralkyl, amino, alkylamino, dialkylamino, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfonyl, arylsulfonyl, acyl, carboxy, alkoxycarbonyl, carboxyalkyl, carboxamido, alkylsulfoxide, acylamino, amidino, —PO3H2, —SO3H, and —B(OH)2,;
R4 represents one, two, three or four residues chosen independently from H, halogen, —OH, loweralkyl, —O-loweralkyl, hydroxyloweralkyl, —CN, CF3, nitro, —SH, —S-loweralkyl, amino, alkylamino, dialkylamino, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfonyl, arylsulfonyl, acyl, carboxy, alkoxycarbonyl, carboxyalkyl, carboxamido, alkylsulfoxide, acylamino, amidino, —PO3H2, —SO3H, and —B(OH)2,
R5g represents one, two, three, four or five residues on Ar chosen independently from halogen, —OH, loweralkyl, —O-loweralkyl, methylenedioxy, ethylenedioxy, hydroxyloweralkyl, —CN, CF3, nitro, —SH, —S-loweralkyl, amino, alkylamino, dialkylamino, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfonyl, arylsulfonyl, acyl, carboxy, alkoxycarbonyl, carboxyalkyl, carboxamido, alkylsulfoxide, acylamino, amidino, —PO3H2, —SO3H, and —B(OH)2;
U is (C2-C6)-alkylene in which one or more individual —CH2— may be replaced by a radical chosen from —S—, —S(O)—, —SO2—, —O—, —C(═O)—, —CHOH—, —NH—, CHF, CF2, —CH(O-loweralkyl)-, —CH(O-loweracyl)-, —CH(OSO3H)—, —CH(OPO3H2)—, —CH(OB(OH)2)—, or —NOH—;
with the provisos that
R5g cannot be —CN; 2,5-dimethoxy; 2,6-dimethoxy or halogen when neither of R4 and R5g includes an —OH, amino, loweralkyl, O-loweralkyl, alkoxycarbonyl, —B(OH)2, —PO3H2 or —SO3H group;
R5g cannot be 2-hydroxy when

OG Complex Work Unit Drawing
represents a 2,5-thienyl residue;
adjacent —CH2— residues in U cannot be replaced by —S—, —S(O)—, —SO2— or —O—; and
—S—, —S(O)—, —SO2—, —O— and —NH— residues in U cannot be separated only by a single carbon.