Patent ID: 6667161
Filing Date: 2003-12-23
Classification: C07H,C12Q

Abstract:
A method of measuring sialidase activity in a sample comprising the step of contacting said sample with a chromogenic sialidase substrate compound or a chromogenic sialidase substrate composition comprising a formula of General Structure I and salts of General Structure I, wherein General Structure I is defined as follows: wherein, for General Structure I, R1, R2, R4, and R5 can each, independently, be selected from the group consisting of H, R11, OC(O)R11, NO2, NHC(O)R11, Cl, Br, I, F, CHO, C(O)R11, C(Nâ€”OH)NH2, OPO3R10, OPO2(CH2jCH3, CH2PO3R10, OSO3R10, OSO2(CH2)jCH3, CH2SO3R10, and CN, where j is an integer from 0 to 3; wherein R3=CHO, (CR12&boxH;CR12)kCN or (CR12&boxH;CR12)kNO2, where k is an integer from 1 to 3, or wherein, wherein, R6, R7, and R8 can each, independently, be selected from the group consisting of H, N3, R11, NO2, NHC(&boxH;NH)N(R10)2, NHC(O)R11, C(O)R11, Cl, Br, I, F, SR10, and (CH2)xC(&boxH;NH)N(R10)2 where x is an integer from 0 to 3; wherein R9 is: 1) OR10 and R10 is C(CH3)3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)(CH2)mCH3 where m is an integer from 0 to 3, or (CH2)mCH3, where m is an integer from 0 to 3, or 2) R9 is selected from the group consisting of C(CH3)3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)(CH2)mCH3 where m is an integer from 0 to 3, CH2CH3, (CH2)2CH3, (CH2)3CH3, N(R10)2, NO2, NHC(&boxH;NH)N(R10)2, NHC(O)R11, C(O)R11, Cl, Br, I, F, SR10, and (CH2)xC(&boxH;NH)N(R10)2 where x is an integer from 0 to 3; wherein R10=H, C(CH3)3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)(CH2)mCH3 where m is an integer from 0 to 3; or (CH2)mCH3, where m is an integer from 0 to 3; wherein R11=R10, OR10, or N(R10)2; wherein, R12=H or (CH2)n; where n is an integer from 0 to 3;or, also for General Structure I, wherein, R3 can be selected from the group consisting of H, R11, OC(O)R11, NHC(O)R11, Cl, Br, l, F, CHO, C(O)R11, C(Nâ€”OH)NH2, OPO3R10, OPO2(CH2)jCH3, CH2PO3R10, OSO3R10, OSO2(CH2)jCH3, CH2SO3R10, or CN, where j is an integer from 0 to 3; R1 and R5 can each, independently, be selected from the group consisting of H, R11, OC(O)R11, NO2, NHC(O)R11, Cl, Br, I, F, CHO, C(O)R11, C(Nâ€”OH)NH2, OPO3R10, OPO2(CH2)jCH3, CH2PO3R10, OSO3R10, OSO2(CH2)jCH3, CH2SO3R10, or CN, where j is an integer from 0 to 3; wherein R2 or R4=H, R11, OC(O)R11, NO2, NHC(O)R11, Cl, Br, I, F, CHO C(O)R11, C(Nâ€”OH)NH2, OPO3R10, OPO2(CH2)jCH3, CH2PO3R10, OSO3R10, OSO2(CH2)jCH3, CH2SO3R10, CN, where j is an integer from 0 to 3, (CR12&boxH;CR12)kCN, and (CR12&boxH;CR12)NO2, where k is an integer from 1 to 3 or wherein, R6, R7, and R8 can each, independently, be selected from the group consisting of H, N3, R11, NO2, NHC(&boxH;NH)N(R10)2, NHC(O)R11, C(O)R11, Cl, Br, I, F, SR10, and (CH2)xC(&boxH;NH)N(R10)2 where x is an integer from 0 to 3; wherein R9 is: 1) OR10 and R10 is C(CH3)3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)(CH2)mCH3 where m is an integer from 0 to 3, or (CH2)m,CH3, where m is an integer from 0 to 3 or, 2) R9 is selected from the group consisting of C(CH3)3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)(CH2)mCH3 where m is an integer from 0 to 3, CH2CH3, (CH2)2CH3, (CH2)3CH3, N(R102, NO2, NHC(&boxH;N)N(R10)2, NHC(O)R11, C(O)R11, Cl, Br, I, F, SR10, and (CH2)xC(&boxH;NH)N(R10)2 where x is an integer from 0 to 3; wherein R10=H, C(CH3)3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)(CH2)mCH3 where m is an integer from 0 to 3, or (CH2)mCH3, where m is an integer from 0 to 3; wherein R11=R10, OR10, or N(R10)2; wherein, R12=H or (CH2)n; where n is an integer from 0 to 3;or, also for General Structure I, wherein, R1 or R5=H, R11, OC(O)R11, NO2, NH(C(O)R11, Cl, Br, L, F, CHO, C(O)R11, C(Nâ€”OH)NH2, OPO3R10, OPO2(CH2)jCH3, CH2PO3R10, OSO3R10, OSO2(CH2)jCH3, CH2SO3R10, CN, where j is an integer from 0 to 3, (CR12&boxH;CR12)kCN and (CR12&boxH;CR12)kNO2, where k is an integer from 1 to 3; wherein, R2 and R4 can each, independently be selected from the group consisting of H, R11, OC(O)R11, NO2, NHC(O)R11, Cl, Br, I, F, CHO, C(O)R11, C(Nâ€”OH)NH2, OPO3R10, OPO2(CH2)jCH3, CH2PO3R10, OSO3R10, OSO2(CH2)jCH3, CH2SO3R10, and CN, where j is an integer from 0 to 3; wherein R3 can be selected from the group consisting of H, R11, OC(O)R11, NHC(O)R11, Cl, Br, I, F, CHO, C(O)R11, C(Nâ€”OH)NH2, OPO3R10, OPO2(CH2)jCH3, CH2PO3R10, OSO3R10, OSO(CH2)jCH3, CH2SO3R10, and CN, where j is an integer from 0 to 3; wherein, R6, R7, and R8 can each, independently, be selected from the group consisting of H, N3, R11, NO2, NHC(&boxH;NH)N(R10)2, NHC(O)R11, C(O)R11, Cl, Br, I, F, SR10, and (CH2)xC(&boxH;NH)N(R10)2 where x is an integer from 0 to 3; wherein R9 is: 1) OR10 and R10 is C(CH3)3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)(CH2)mCH3 where m is an integer from 0 to 3, or (CH2)mCH3, where m is an integer from 0 to 3, or 2) R9 is selected from the group consisting of C(CH3)3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)(CH2)mCH3 where m is an integer from 0 to 3, CH2CH3, (CH2)2CH3, (CH2)3CH3, N(R10)2, NO2, NHC(&boxH;NH)N(R10), NHC(O)R11, C(O)R11, Cl, Br, I, F, SR10, and (CH2)xC(&boxH;NH)N(R10)2 where x is an integer from 0 to 3; wherein R10=H, C(CH3)3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)(CH2)mCH3 where m is an integer from 0 to 3, or (CH2)mCH3, where m is an integer from 0 to 3; wherein R11=R10, OR10, or N(R10)2; and wherein, R12=H or (CH2)n; where n is an integer from 0 to 3.