US 12,139,459 B2
Enhancer of fertilization function of sperm
Takaaki Abe, Miyagi (JP); Nobuo Yaegashi, Miyagi (JP); Masahito Tachibana, Miyagi (JP); and Kenichiro Hayashi, Okayama (JP)
Assigned to TOHOKU UNIVERSITY, Miyagi (JP); and KAKE EDUCATIONAL INSTITUTION, Okayama (JP)
Appl. No. 15/734,579
Filed by TOHOKU UNIVERSITY, Miyagi (JP); and KAKE EDUCATIONAL INSTITUTION, Okayama (JP)
PCT Filed Jun. 4, 2019, PCT No. PCT/JP2019/022082
§ 371(c)(1), (2) Date Apr. 28, 2021,
PCT Pub. No. WO2019/235455, PCT Pub. Date Dec. 12, 2019.
Claims priority of application No. 2018-107827 (JP), filed on Jun. 5, 2018.
Prior Publication US 2022/0106270 A1, Apr. 7, 2022
Int. Cl. C07D 209/12 (2006.01); C07D 209/18 (2006.01); C07D 209/20 (2006.01); C07D 401/06 (2006.01); C12N 5/073 (2010.01); C12N 5/075 (2010.01); C12N 5/076 (2010.01)
CPC C07D 209/12 (2013.01) [C07D 209/18 (2013.01); C07D 209/20 (2013.01); C07D 401/06 (2013.01); C12N 5/0604 (2013.01); C12N 5/0609 (2013.01); C12N 5/061 (2013.01); C12N 2500/30 (2013.01); C12N 2501/999 (2013.01)] 6 Claims
 
1. A method for increasing fertilization rate of a mammal sperm with a mammal ovum, comprising step (a) of transferring at least one collected mammal sperm into a physiological aqueous solution containing one or more compounds selected from the group consisting of compounds of the following formula (I0), formula (II), and formula (III), and physiologically acceptable salts thereof when R3 is OH:

OG Complex Work Unit Chemistry
[wherein R1 is a benzoylmethyl group whose benzene ring is unsubstituted or a benzoylmethyl group whose benzene ring is substituted by an alkyl group having 1 to 7 carbon atoms, an alkoxyl group having 1 to 7 carbon atoms, fluorine, and/or chlorine; an unsubstituted or fluorine-substituted linear or branched alkyl group having 4 to 6 carbon atoms; or phenyl group-or cyclopentyl group-substituted methylene or ethylene; wherein the phenyl group is optionally further substituted by one or more phenyl groups, Z1, Z2, Z3 and Z4 are the same or different and each is a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, a C2 to C6 alkenyl group, a C2 to C6 alkynyl group, an organic oxy group represented by OR8, R8 is a C1 to C7 alkyl group, a C2 to C6 alkenyl group or a C2 to C6 alkynyl group, Z5 is a hydrogen atom or a C1 to C6 alkyl group, R3 is any group selected from OH, OR4, NHR4, and NR4R5, and R4 and R5 are the same or different and each is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms],

OG Complex Work Unit Chemistry
[wherein R6 is hydrogen or a methyl group, X is an alkylene group having 4 to 6 carbon atoms or an ether group having 4 carbon atoms, R3 is any group selected from OH, OR4, NHR4, and NR4R5, and R4 and R5 are the same or different and each is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms], and

OG Complex Work Unit Chemistry
[wherein A is indole or naphthalene, and when A is indole, positions 3 and 5 of the indole are substituted by an acetic acid group and R7O, respectively, and when A is naphthalene, positions 1 and 7 of the naphthalene are substituted by an acetic acid group and R7O, respectively, R7 is an alkyl group having 1 to 5 carbon atoms or a benzyl group, wherein the benzene ring of the benzyl group is optionally substituted by one or more alkyl groups having 1 to 3 carbon atoms or alkoxyl groups having 1 to 3 carbon atoms, R3 is any group selected from OH, OR4, NHR4, and NR4R5, and R4 and R5 are the same or different and each is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms].