US 11,744,246 B2
Preparation of mammalian oocyte for fertilization via a soluble human PH20 hyaluronidase polypeptide
Matthias Weiss, Stein (CH); Laura Quaranta, Stein (CH); and Farhan Bou Hamdan, Stein (CH)
Assigned to SYNGENTA PARTICIPATIONS AG, Basel (CH)
Filed by SYNGENTA PARTICIPATIONS AG, Basel (CH)
Filed on Aug. 5, 2021, as Appl. No. 17/394,946.
Application 17/394,946 is a continuation of application No. 16/646,505, abandoned, previously published as PCT/EP2018/074515, filed on Sep. 11, 2018.
Claims priority of application No. 17190894 (EP), filed on Sep. 13, 2017.
Prior Publication US 2022/0015364 A1, Jan. 20, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 215/38 (2006.01); A01N 43/42 (2006.01)
CPC A01N 43/42 (2013.01) [C07D 215/38 (2013.01)] 18 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
wherein
X is O or S;
R1 is hydrogen, halogen, methyl or cyano;
R2 and R3 are each independently selected from hydrogen, halogen, methoxy and methyl;
R4 is hydrogen, C1-C4 alkyl, C1-C2 haloakyl, C2-C4 alkenyl or C3-C6 cycloalkyl, wherein the alkyl, alkenyl and cycloalkyl may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkylthio;
R5 is hydrogen, cyano or C1-C4 alkyl;
R6 is C1-C5 alkyl, C3-C7 cycloalkyl, C3-C5 alkenyl, C3-C6 cycloalkenyl, C3-C5 alkynyl, a C5-C10 saturated or partially unsaturated bicyclic carbocycle, aryl, aryl(C1-C4)alkyl, a saturated or partially unsaturated heterocycle or heteroaryl, wherein the alkyl, cycloalkyl, alkenyl, cycloalkenyl, carbocycle, alkynyl, may be optionally substituted with one or more substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 haloalkoxy, C1-C3 haloalkylthio, C3-C5 cycloalkyl or phenyl, and wherein the aryl, heterocycle or heteroaryl may be optionally substituted with one or more substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 haloalkoxy, C1-C3 haloalkylthio or C3-C5 cycloalkyl; and
R11 is hydrogen, methyl or halogen; or a salt, enantiomer or N-oxide thereof.