	US 7,501,404 B2
	Substituted azetidinones
Thomas Bannister, Palm Beach Gardens, Fla. (US); Cassandra Celatka, Hull, Mass. (US); Nizal S. Chandrakumar, North Grafton, Mass. (US); Hongfeng Deng, Acton, Mass. (US); Zihong Guo, Southbury, Conn. (US); Lei Jin, Wellesley, Mass. (US); Tsvetelina Lazarova, Brookline, Mass. (US); Jian Lin, Walpole, Mass. (US); Scott T. Moe, Marlborough, Mass. (US); Pamela Nagafuji, Cambridge, Mass. (US); Manuel Navia, Lexington, Mass. (US); Amy Ripka, Winthrop, Mass. (US); Michael J. Rynkiewicz, Boston, Mass. (US); Kerry L. Spear, Concord, Mass. (US); James E. Stickler, Milton, Mass. (US); and Roger Xie, Southborough, Mass. (US)
Assigned to DAIMED, Cambridge, Mass. (US)
Filed on Apr. 04, 2006, as Appl. No. 11/398,438.
Claims priority of provisional application 60/668325, filed on Apr. 04, 2005.
Prior Publication US 2007/0105832 A1, May 10, 2007
Int. Cl. C07D 205/08 (2006.01); C07D 205/085 (2006.01); C07D 401/14 (2006.01); C07D 401/12 (2006.01); C07D 401/06 (2006.01); C07D 403/12 (2006.01); C07D 403/14 (2006.01); C07D 403/04 (2006.01); A61K 31/397 (2006.01); A61K 31/506 (2006.01); A61K 31/4427 (2006.01); A61K 31/41 (2006.01)

U.S. Cl. 514—210.02 [514/210.05; 540/200; 540/354; 540/355; 540/360; 540/362; 540/363; 540/364]

17 Claims

1. A compound according to the following structure:

wherein

A is a member selected from CR¹R², O and S

wherein

R¹is H,

R²is H,

B is a member independently selected from unsubstituted alkyl, —S—, and —O—;

m is an integer selected from 0 to 2;

C is a member selected from a bond and —O—;

D is a member selected from

X is a member selected from S and O;

Y is a member selected from a bond, C═O, and SO₂;

R_ais a member selected from NR⁷R⁸and substituted and unsubstituted heteroaryl

wherein

R⁷is a member selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; and

R⁸is a member selected from substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;

R_cis a member selected from H and substituted or unsubstituted alkyl;

R_dis a member selected from R¹⁶and (CR¹⁴R¹⁵)_pR¹⁶

wherein

p is 1;

R¹⁴is H;

R¹⁵is H; and

R¹⁶is a member selected from C(O)R¹⁸, OH, and

wherein

R¹⁸is a member from OR²¹, NR¹⁹R²⁰, and NR¹⁹SO₂R²⁰

wherein

R²¹is a member selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, and substituted or unsubstituted aryl;

R¹⁹is a member selected from H and substituted or unsubstituted alkyl; and

R²⁰is a member selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; and

R¹⁹and R²⁰can be optionally joined, together with the atoms to which they are attached, to form a 6 membered ring; and

R_dis H;

with the proviso for the compound, or salts thereof, that if:

Y is a member selected from C═O and SO₂;

ABC, in combination, form unsubstituted alkyl; and

D is substituted or unsubstituted guanidine;

then R_ccannot be a member selected from CH₃and CH₂CH₃; and R_dand R_d′ cannot be members selected from H and COOR^1a; and H and CONR¹⁹R²⁰;

wherein

R^1ais a member independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, and substituted or unsubstituted aryl;

R¹⁹is selected from H and substituted or unsubstituted alkyl; and

R²⁰is selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl.