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1. (WO2018162610) NOVEL PHOSPHORYLATION REAGENTS AND USES THEREOF

Pub. No.:    WO/2018/162610    International Application No.:    PCT/EP2018/055694
Publication Date: Fri Sep 14 01:59:59 CEST 2018 International Filing Date: Fri Mar 09 00:59:59 CET 2018
IPC: C07F 9/24
C07H 21/00
Applicants: ETH ZURICH
Inventors: HALL, Jonathan
PRADERE, Ugo
Title: NOVEL PHOSPHORYLATION REAGENTS AND USES THEREOF
Abstract:
The present invention relates to compounds of formula (I) wherein R1, R2, R3, R4, R5, R6, R7, and R8 are independently of each other hydrogen, halogen, nitro, cyano, C1-C6alkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, each independently of each other optionally substituted with cyano, nitro, halogen; or independently thereof R1 and R5 represent together a bond or form together -CH2-; or independently thereof R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, R7 and R8 form together independently of each other a bivalent residue –R12R13–, wherein each of said bivalent residue –R12R13– independently at each occurrence is C3-C5alkylene, C3-C5alkenylene or C3-C5alkdienylene, each independently optionally substituted with halogen, nitro, cyano, C1-C2alkyl C1-C2alkoxy, C1-C2haloalkyl; or independently thereof wherein each of said bivalent residue –R12R13– independently at each occurrence together with the vicinal C atoms to which they are attached independently of each other form a heterocyclic ring or a hetero-aromatic ring, each independently optionally substituted with halogen, nitro, cyano, C1-C2alkyl C1-C2alkoxy, C1-C2haloalkyl; Rz is H, C1-C6alkyl optionally substituted with halogen, C1-C3alkoxy, or Rz is phenyl optionally substituted with halogen, C1-C3alkyl, C1-C3alkoxy, wherein preferably Rz is H; R9 is C1-C9alkyl optionally substituted with cyano, nitro, halogen, -NHC(O)C1-C3alkyl, - NHC(O)C1-C3haloalkyl, C1-C3alkylsulfonyl; aryl, C1-C6alkylenearyl, C1-C6alkylenediaryl independently of each other optionally substituted with cyano, nitro, halogen, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, -NHC(O)C1-C3alkyl, NHC(O)C1-C3haloalkyl, C1- C3alkylsulfonyl; R10 and R11 are independently of each other C1-C9alkyl optionally substituted with cyano, nitro, halogen, C2-C6alkenyl, C3-C6cycloalkyl, C1-C3alkoxy, phenyl optionally substituted with cyano, nitro, halogen, C1-C3 alkyl, C1-C3alkoxy; or together with the nitrogen atom to which they are attached form a heterocyclic ring, wherein preferably said heterocyclic ring is selected from pyrollidinyl, piperidinyl, morpholinyl, piperazinyl and homopiperazine, wherein said heterocyclic ring is optionally substituted with C1-C3 alkyl; and the use of the compounds in a method of converting terminal hydroxyl groups of oligonucleotides into phosphate monoesters.