US 7,550,484 B2
Chemokine receptor binding heterocyclic compounds with enhanced efficacy
Gary J. Bridger, Bellingham, Wash. (US); Ernest J. McEachern, White Rock (Canada); Renato Skerlj, Vancouver (Canada); Dominique Schols, Herent (Belgium); Ian Baird, West Abbotsford (Canada); Al Kaller, Vancouver (Canada); Curtis Harwig, Vancouver (Canada); Yongbao Zhu, Coquitlam (Canada); Gang Chen, Langley (Canada); Krystyna Skupinska, New Westminister (Canada); and Markus Metz, Delta (Canada)
Assigned to Genzyme Corporation, Cambridge, Mass. (US)
Filed on Apr. 22, 2004, as Appl. No. 10/831,098.
Claims priority of provisional application 60/505230, filed on Sep. 22, 2003.
Claims priority of provisional application 60/464858, filed on Apr. 22, 2003.
Prior Publication US 2005/0059702 A1, Mar. 17, 2005
Int. Cl. A61K 31/445 (2006.01); C07D 401/04 (2006.01)
U.S. Cl. 514—318  [514/235.5; 544/124; 546/193; 546/194] 11 Claims
 
1. A compound of the formula

OG Complex Work Unit Drawing
or the pharmaceutically acceptable salts thereof;
wherein each of rings A and B is independently a pyridinyl optionally substituted with one or more substituents selected from the group consisting of alkyl (C1-10), alkenyl (C2-10), and alkynyl (C2-10);
ring C is an unsubstituted piperidine or is piperidine substituted only at position 4 with OH, OMe, CN, OBz, ═NOEt, or ═NOBz;
wherein Y is phenyl, benzimidazole or imidazole; or
is selected from the group consisting of,
—(CH2)m NH2,
—(CH2)m NHCH3,
—(CH2)m NH(CH2)mNH2,
—(CH2)m NH(CH2)mNH(CH2)mNH2,
—(CH2)m OH,
—(CH2)m CO(CH2)mOH,
—(CH2)m CO(CH2)mNH2,
—(CH2)m CO(CH2)mNH(CH2)mNH2,
—(CH2)m NHCO(CH2)mNH2,
—(CH2)m NH (CH2)mCO2H,
—(CH2)m NH (CH2)mSO2H,
—(CH2)m NHCO(CH2)mNH(CH2)mNH2,
—(CH2)m NHCO(CH2)mNH(CH2)mNH(CH2)mNH(CH2)mNH2,
—(CH2)m NH(CH2)mOH,
—(CH2)m CH═NOH,
—(CH2)m CONH(CH2)mOH,
—(CH2)m N[(CH2)mCO2H]2,
—(CH2)m NHCOZ and
—(CH2)m NH—(CH2)mZ,
wherein each m is independently 0-4; and Z is an optionally substituted aromatic or heteroaromatic moiety containing 5-12 ring members;
L is (CR32)1 where each R3 is H or alkyl wherein a single bond in alkyl may be replaced with a double or triple bond and wherein 1 is 1-6.