US 7,465,798 B2
Methods and compositions for selectin inhibition
Neelu Kaila, Lexington, Mass. (US); Silvano L. Debernardo, Verona, N.J. (US); Kristin M. Jantz, Arlington, Mass. (US); Raymond T. Camphausen, Wayland, Mass. (US); Patricia W. Bedard, Mansfield, Mass. (US); and Adrian Huang, Lexington, Mass. (US)
Assigned to Wyeth, Madison, N.J. (US)
Filed on Nov. 09, 2004, as Appl. No. 10/984,522.
Claims priority of provisional application 60/518939, filed on Nov. 10, 2003.
Claims priority of provisional application 60/542986, filed on Feb. 09, 2004.
Prior Publication US 2005/0101569 A1, May 12, 2005
Int. Cl. C07D 221/06 (2006.01)
U.S. Cl. 546—101 35 Claims
 
1. A compound having the Formula III:

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof,
wherein:
bond a and bond b are each a single bond;
k is 1;
Q1, Q2, Q3 and Q are each CHR2;
L is CO2H or an ester thereof;
Y is O, (CR3R4)por NR5;
n′ is 0 or 1;
p is 1 to 3;
X is OH, OR3, OC1-6 alkyl, OC(═O)-aryl, OC(═O)C1-6 alkyl OC(═O)OC1-6 alkyl, or NR3R3;
each R1, R3, R3, and R4 is independently selected from the group consisting of hydrogen, C1-6 alkyl, C1-6 perhaloalkyl OC1-6 alkyl, OC1-6 perhaloalkyl, halogen, thioalkyl, CN, OH, SH, (CH2)nOSO3H, (CH2)nSO3H, (CH2)nCO2R6, OSO3R6, SO3R6, PO3R6R7;
each R12 is independently selected from the group consisting of hydrogen, C1-6 alkyl, C1-6 perhaloalkyl, OC1-6 alkyl, OC1-6 perhaloalkyl, thioalkyl, OH, (CH2)1OSO3H, (CH2)1SO3H, (CH2)1CO2R6,(CH2)1SO2NR8R9, (CH2)1C(═O)NR8R9, NR8R9, alkenyl, alkynyl, or NHCOR8, wherein any of said alkyl, Oalkyl, alkenyl or alkynyl can optionally be substituted with up to three substituents selected from the group consisting of halogen, C1-6 alkyl, OC1-6 alkyl and CN;
each n is an independently selected integer from 0 to 6;
each 1 is an independently selected integer from 1 to 6; and
Z is aryl, arylalkyl, heteroaryl or heterocyclo, wherein each of said aryl, arylalkyl, heteroaryl and heterocyclo is optionally substituted.