US 6,982,336 B2
1,2-dioxetane derivatives, luminescent reagents, luminescence methods and measuring methods
Masakatsu Matsumoto, Machida (Japan); Nobuko Watanabe, Kamakura (Japan); and Masashi Yamada, Yokohama (Japan)
Assigned to Tosoh Corporation, Shinnanyo (Japan)
Filed on Mar. 07, 2002, as Appl. No. 10/91,447.
Claims priority of application No. 2001-065347 (JP), filed on Mar. 08, 2001.
Prior Publication US 2002/0132365 A1, Sep. 19, 2002
Int. Cl. G01N 21/76 (2006.01); C07D 261/08 (2006.01); C07D 275/02 (2006.01); C07D 417/14 (2006.01); C07F 7/18 (2006.01)
U.S. Cl. 548—247 10 Claims
 
1. A 1,2-dioxetane derivative of the formula (I):
OG Complex Work Unit Drawing
wherein each of R1 and R2 which are independent of each other, is a hydrogen atom, an alkyl group or an aryl group, or R1 and R2 may together form a cyclic or polycyclic organic ring group spiro-bonded to the dioxetane ring, R3 is an alkyl group or an aryl group, or R3 and R1 or R2 may together form a condensed ring containing the dioxetane ring and a hetero atom, and Ar is a group of the formula (A):
OG Complex Work Unit Drawing
wherein R4 is a hydroxyl group, an alkoxyl group, an aralkyloxy group, a group of —OSi(R5R6R7) (wherein each of R5, R6 and R7 which are independent of one another, is an alkyl group or an aryl group), a phosphate group or a group of —S(C═O)R8 (wherein R8 is an alkyl group or an aryl group), each of R9 and R10 which are independent of each other, is a hydrogen atom, an alkyl group, an aryl group or a halogen atom, X is a halogen atom, and V is an oxygen atom or a sulfur atom, or wherein Ar is a group of the formula (B):
OG Complex Work Unit Drawing
wherein R4 is the same as R4 in the above formula (A), each of R11 and R12 which are independent of each other, is a hydrogen atom, an alkyl group, an aryl group or a halogen atom, Y is a halogen atom, and W is an oxygen atom or a sulfur atom.