Patent ID: 6844346
Filing Date: 2005-01-18
Classification: C07H

Abstract:
1. A chromogenic sialidase substrate compound, having a formula selected from the group consisting of General Structure I; General Structure II, General Structure IIIa; General Structure IIIb; General Structure IVa; General Structure IVb; and of the General Structures, wherein the General Structures are defined as follows: wherein, R 1 ═H, R 6 , OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , NHC(O)R 6 , NHC(O)OR 6 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein R 2 ═H, R 6 , OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , NHC(O)R 6 , NHC(O)OR 6 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein R 4 ═H, R 6 , OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , NHC(O)R 6 , NHC(O)OR 6 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein R 5 ═H, R 6 , OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , NHC(O)R 6 , NHC(O)OR 6 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ,) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein, R 3 ═NO 2 , CHO, (CR 8 ═CR 8 ) k CN or (CR 8 ═CR 8 ) k NO 2 , where k is an integer from 1 to 3, or wherein, R 6 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 7 ═R 6 , OR 6 , or N(R 6 ) 2 ; wherein R 8 ═H or (CH 2 ) n CH 3 ; where n is an integer from 0 to 3; alternatively, for General Structure I, R 1 ═H, R 6 , OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein, R 2 or R 4 ═H, R 6 , OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein, R 3 ═H, R 6 , OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein, R 5 ═H, OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein, R 2 or R 4 ═NO 2 , CHO, (CR 8 ═CR 8 ) k CN or (CR 8 ═CR 8 ) k NO 2 , where k is an integer from 1 to 3, or wherein, R 6 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 7 ═R 6 , OR 6 , or N(R 6 ) 2 ; wherein R 8 ═H or (CH 2 ) n CH 3 ; where n is an integer from 0 to 3; alternatively, for General Structure I, R wherein, R 1 ═H, OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein, R 2 ═H, OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein, R 3 ═H, OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein R 4 ═H, OR 6 , OC(O)R 7 , NO 2 , NH 2 , N(R 6 ) 2 , Cl, Br, I, F, CHO, CO 2 R 6 , C(O)N(R 6 ) 2 , C(N—OH)NH 2 , OPO 3 R 6 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 6 , OSO 3 R 6 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 6 , or CN, where j is an integer from 0 to 3; wherein, R 5 ═H or (CH 2 ) k CH 3 , where k is an integer from 0 to 4; wherein, R 6 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 7 ═R 6 , OR 6 , or N(R 6 ) 2 ; wherein, R 1 ═H, OR 3 , OC(O)R 4 , NO 2 , NH 2 , N(R 3 ) 2 , Cl, Br, I, F, CHO, CO 2 R 3 , C(O)N(R 3 ) 2 , C(N—OH)NH 2 , OPO 3 R 3 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 3 , OSO 3 R 3 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 3 , or CN, where j is an integer from 0 to 3; wherein, R 2 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein R 3 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 4 ═R 3 ,OR 3 , or N(R 3 ) 2 ; wherein, R 1 ═H, OR 3 , OC(O)R 4 , NO 2 , NH 2 , N(R 3 ) 2 , Cl, Br, I, F, CHO, CO 2 R 3 , C(O)N(R 3 ) 2 , C(N—OH)NH 2 , OPO 3 R 3 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 3 , OSO 3 R 3 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 3 , or CN, where j is an integer from 0 to 3; wherein, R 2 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 3 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 4 ═R 3 , OR 3 , or N(R 3 ) 2 ; wherein, R 1 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 2 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 3 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 4 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 5 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 6 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 7 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein R 8 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 9 ═R 8 , OR 8 , or N(R 8 ) 2 ; and wherein, R 1 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 2 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 3 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 4 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 5 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 6 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein, R 7 ═H, OR 8 , OC(O)R 9 , NO 2 , NH 2 , N(R 8 ) 2 , Cl, Br, I, F, CHO, CO 2 R 8 , C(O)N(R 8 ) 2 , C(N—OH)NH 2 , OPO 3 R 8 , OPO 2 (CH 2 ) j CH 3 , CH 2 PO 3 R 8 , OSO 3 R 8 , OSO 2 (CH 2 ) j CH 3 , CH 2 SO 3 R 8 , or CN, where j is an integer from 0 to 3; wherein R 8 ═H, C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 ) m CH 3 , or (CH 2 ) m CH 3 , where m is an integer from 0 to 3; wherein, R 9 ═R 8 , OR 8 , or N(R 8 ) 2 ,