US 10,851,065 B2Granted

Tetrasubstituted alkene compounds and their use

AssigneeEisai R&D Management Co., Ltd.

InventorsMark Bock, Ming-Hong Hao, Manav Korpal, Vijay Kumar Nyavanandi, Xiaoling Puyang, Susanta Samajdar, Peter Gerard Smith, John Wang, Guo Zhu Zheng, Ping Zhu

Life of this patent

Estimating the term…

Abstract

Disclosed herein are compounds, or pharmaceutically acceptable salts thereof, and methods of using the compounds for treating breast cancer by administration to a subject in need thereof a therapeutically effective amount of the compounds or pharmaceutically acceptable salts thereof. The breast cancer may be an ER-positive breast cancer and/or the subject in need of treatment may express a mutant ER-α protein.

Claims20

Dependent claims

A compound or pharmaceutically acceptable salt thereof, given by formula I:

wherein:
R1 is selected from the group consisting of cyclobutyl and —CH2CF3;
R2 is selected from the group consisting of H and F;
n is 0-1;
R3 is F when n=1;
m is 0-2;
R4 are the same or different and are independently selected from the group consisting of F, CF3, Cl, isopropyl, —OCH3, —OCHF2, —OCF3, ethyl and methyl;
p is 0-1;
R5 is F when p=1;
R6 and R7 are the same or different and are independently selected from the group consisting of methyl, ethyl, propyl, —CH2CH2OH and
wherein r is 1 or 2;
or, wherein R6 and R7 form a 4-6 membered heterocyclic ring with the N to which they are attached, wherein said heterocyclic ring optionally includes an oxygen atom, and wherein said heterocyclic ring is optionally substituted with F, or —CH2F;
R8 is selected from the group consisting of H and CH3;
or a pharmaceutically acceptable salt thereof.

11 more elements

A compound selected from the group consisting of (E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy) ethyl) amino)-N,N-dimethylbut-2-enamide;

(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-phenyl but-1-en-1-yl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-(3-fluoro-5-(trifluoromethyl) phenyl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(4-fluoro-1H-indazol-5-yl)-2-phenyl but-1-en-1-yl) phenoxy) ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(3,5-difluorophenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(3,4-difluorophenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(3-chloro-5-fluorophenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy) ethyl) amino)-N-methyl-N-(prop-2-yn-1-yl)but-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl) amino)-N-(but-3-yn-1-yl)-N-methylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl) amino)-1-(azetidin-1-yl)but-2-en-1-one;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl) amino)-1-(pyrrolidin-1-yl)but-2-en-1-one;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl) amino)-1-(piperidin-1-yl)but-2-en-1-one;
(E)-4-((2-(4-((E)-2-cyclobutyl-1-(1H-indazol-5-yl)-2-phenylvinyl)phenoxy) ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-cyclobutyl-1-(3-fluoro-1H-indazol-5-yl)-2-phenylvinyl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide 2,2,2-trifluoro acetate;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl) amino)-1-morpholinobut-2-en-1-one;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl) amino)-N-ethyl-N-methylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl) amino)-N-methyl-N-propylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl)amino)-N-(2-hydroxyethyl)-N-methylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl) amino)-N,N,3-trimethylbut-2-enamide;
(Z)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl) amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-cyclobutyl-1-(1H-indazol-5-yl)-2-phenylvinyl)phenoxy)ethyl)amino)-1-morpholinobut-2-en-1-one;
(E)-4-((2-(4-((E)-2-cyclobutyl-1-(4-fluoro-1H-indazol-5-yl)-2-phenylvinyl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-((5-((Z)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)pyridin-2-yl) oxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-(o-tolyl)but-1-en-1-yl)phenoxy) ethyl)amino)-N-(2-hydroxyethyl)-N-methylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N-(2-hydroxyethyl)-N-methylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-(4-isopropyl phenyl)but-1-en-1-yl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-4-chloro-1-(1H-indazol-5-yl)-2-phenyl but-1-en-1-yl)phenoxy) ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-(4-isopropyl phenyl)but-1-en-1-yl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2-(difluoromethoxy)phenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-(2-(trifluoro-methoxy)phenyl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-(2-isopropyl phenyl)but-1-en-1-yl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2-ethylphenyl)-1-(1H-indazol-5-yl) but-1-en-1-yl)phenoxy) ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-(o-tolyl)but-1-en-1-yl)phenoxy)ethyl) amino)-N,N-dimethylbut-2-enamide;
(E)-4-((24(5-((Z)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)pyrimidin-2-yl) oxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-1-(azetidin-1-yl)-4(2-(4-((E)-2-cyclobutyl-1-(1H-indazol-5-yl)-2-phenylvinyl) phenoxy)ethyl)amino)but-2-en-1-one;
(E)-1-(azetidin-1-yl)-4-((2-(4-((E)-2-cyclobutyl-1-(3-fluoro-1H-indazol-5-yl)-2-phenylvinyl)phenoxy)ethyl)amino)but-2-en-1-one;
(E)-4-((2-(4-((E)-2-cyclobutyl-1-(1H-indazol-5-yl)-2-phenylvinyl) phenoxy) ethyl)amino)-N-(2-hydroxyethyl)-N-methylbut-2-enamide;
(E)-1-(azetidin-1-yl)-4-((2-(4-((E)-2-cyclobutyl-1-(1H-indazol-5-yl)-2-(o-tolyl) vinyl)phenoxy)ethyl)amino)but-2-en-1-one;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-(2-fluorophenyl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-(3-fluoro phenyl)but-1-en-1-yl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-(3-fluorophenyl)but-1-en-1-yl) phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2-chloro-4-fluorophenyl)-2-cyclobutyl-1-(3-fluoro-1H-indazol-5-yl)vinyl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(2-fluoro-4-((Z)-1-(3-fluoro-1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2,6-difluorophenyl)-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-(pyridin-3-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-(pyridin-4-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N, N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylprop-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-cyclopropyl-1-(1H-indazol-5-yl)-2-phenylvinyl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(4-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-((5-((Z)-2-(2-chloro-4-fluorophenyl)-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)pyridin-2-yl)oxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-((5-((Z)-2-(2-chloro-4-fluorophenyl)-4,4,4-trifluoro-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)pyridin-2-yl)oxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-N,N-dimethyl-4-((2-((5-((Z)-4,4,4-trifluoro-1-(3-fluoro-1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)pyridin-2-yl)oxy)ethyl)amino)but-2-enamide;
(E)-N,N-dimethyl-4-((2-(4-((E)-4,4,4-trifluoro-1-(3-fluoro-1H-indazol-5-yl)-2-(3-fluoropyridin-4-yl)but-1-en-1-yl)phenoxy)ethyl)amino)but-2-enamide;
(E)-N,N-dimethyl-4-((2-((5-((Z)-4,4,4-trifluoro-1-(3-fluoro-1H-indazol-5-yl)-2-(3-fluoropyridin-4-yl)but-1-en-1-yl)pyridin-2-yl)oxy)ethyl)amino)but-2-enamide;
(E)-N,N-dimethyl-4-((2-(4-((E)-2-phenyl-1-(1H-pyrazolo[4,3-b]pyridin-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)but-2-enamide;
(E)-4-((2-(3-fluoro-4-((Z)-1-(3-fluoro-1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2,4-difluorophenyl)-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3,6-difluoro-1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-(pyridin-2-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-((5-((Z)-1-(3-fluoro-1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)pyridin-2-yl)oxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-N,N-dimethyl-4-((2-(4-((E)-4,4,4-trifluoro-1-(3-fluoro-1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl)amino)but-2-enamide;
(E)-4-((2-((5-((Z)-2-cyclobutyl-1-(3-fluoro-1H-indazol-5-yl)-2-phenylvinyl)pyridin-2-yl)oxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2-chlorophenyl)-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-(pyridin-4-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N-(2-hydroxyethyl)-N-methylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(7-fluoro-1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-phenylpent-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3,7-difluoro-1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2,5-difluorophenyl)-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-2-(3-fluoropyridin-4-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(3-fluoro-1H-indazol-5-yl)-3-methyl-2-phenylbut-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-5-((2-(4-((E)-4-fluoro-1-(3-fluoro-1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylpent-2-enamide;
(E)-5-((2-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylpent-2-enamide;
(E)-4-((2-(4-((E)-2-(2-chl oro-4-fluorophenyl)-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N,2-trimethylbut-2-enamide;
(E)-4-((2-(4-((E)-2-(2-chloro-4-fluorophenyl)-4,4,4-trifluoro-1-(3-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-(phenyl-d5)but-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)ethyl)amino)-N,N-dimethylpent-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)propyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((1-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)propan-2-yl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-((6-((Z)-1-(3-fluoro-1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)pyridin-3-yl)oxy)ethyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((3-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)propyl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((3-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)butan-2-yl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((1-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)-2-methylpropan-2-yl)amino)-N,N-dimethylbut-2-enamide;
(E)-4-((2-(4-((E)-1-(1H-indazol-5-yl)-2-phenylbut-1-en-1-yl)phenoxy)-2-methylpropyl)amino)-N,N-dimethylbut-2-enamide;
and (E)-4-((2-(4-((E)-2-cyclobutyl-1-(3-fluoro-1H-indazol-5-yl)-2-phenylvinyl)phenoxy)ethyl)amino)-N-(2-hydroxyethyl)-N-methylbut-2-enamide;
or a pharmaceutically acceptable salt thereof.

83 more elements

A compound given by formula III:

wherein:
R1 is selected from the group consisting of —CH2CF3, —CH2CH3, and cyclobutyl;
R2 is selected from the group consisting of H, halogen, hydroxy, C1-C3 alkyl, C3-C4 cycloalkyl and C4 heterocyclic ring;
when n is not 0, R3 are the same or different, and are independently selected from the group consisting of H, halogen, C1-C6 alkyl and C1-C3 alkoxy optionally substituted with at least one halogen;
n is 0-3;
when m is not zero, R4 are the same or different and are independently selected from the group consisting of H, halogen, C1-C6 alkyl, and ORii, wherein R11 is selected from the group consisting of C3-C6 cycloalkyl, C1-C6 alkyl, aryl, heteroaryl and a 4-6 membered heterocyclic ring;
m is 0-5;
when p is not 0, R5 are the same or different and are independently selected from the group consisting of H, halogen, C1-C4 alkyl, C alkoxy, C3-C4 cycloalkyl, C3-C6 cycloalkoxy and C4 heterocycle;
p is 0-3;
q is 1-2;
R8 and R10 are the same or different and are independently selected from the group consisting of halogen, H and C1-C3 alkyl;
R9 is selected from the group consisting of H, C1-C6 alkyl and C3-C6 cycloalkyl;
Y is selected from the group consisting of —S(O)2R6, —S(O)2NR6R7, —C(O)NR6R7, —C(O)R6, —C(O)OR6, —CN;
or wherein Y and R10 both represent —CF3;
R6 and R7 are the same or different and are independently selected from the group consisting of H, C1-C6 alkyl, C3-C6 cycloalkyl, aryl, heteroaryl and a 4-6 membered heterocyclic ring wherein said alkyl is saturated or unsaturated or wherein R6 and R7 form a 4-6 membered heterocyclic ring with the N to which they are attached, optionally also containing an O atom;
R12 is selected from the group consisting of H, C3-C4 cycloalkyl and C1-C6 alkyl;
and
wherein any carbon containing moiety of R1-R12 may be optionally substituted with one or more halogen atoms, fluoromethane, difluoromethane or trifluoromethane, or —OH;
or a pharmaceutically acceptable salt thereof.

16 more elements

Dependencies are inferred from the claim text.

Facts

Application: 15/713,107Filed 22 Sep 2017 · continuation
Priority: 29 May 2015
Published: US 2018/0127378 A110 May 2018
Granted: 1 Dec 2020
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

A61P 15/00
Drugs for genital or sexual disorders
C07D 231/56
Condensed with carbocyclic rings or ring systems: benzopyrazoles; Hydrogenated benzopyrazoles
A61P 35/00
Antineoplastic agents
C07D 401/06
Containing two hetero rings: linked by a carbon chain containing only aliphatic carbon atoms

Family

Application62/168,529Us provisional application · filed 29 May 2015
Application62/168,581Us provisional application · filed 29 May 2015
Application62/269,745Us provisional application · filed 18 Dec 2015
Application15/167,373Parent of this continuation · filed 27 May 2016
US 2018/0127378 A1Pre-grant publication · published 10 May 2018
US 9,796,683 B2Parent of this continuation
US 2016/0347717 A1Published application
US 10,851,065 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

Facts

Application

15/713,107Filed 22 Sep 2017 · continuation

Priority

29 May 2015

Published

US 2018/0127378 A110 May 2018

Granted

1 Dec 2020

Term ends

Not estimatedThe source records don’t support an estimate.

Classification10 codes

A61P 15/00
Drugs for genital or sexual disorders
C07D 231/56
Condensed with carbocyclic rings or ring systems: benzopyrazoles; Hydrogenated benzopyrazoles
A61P 35/00
Antineoplastic agents
C07D 401/06
Containing two hetero rings: linked by a carbon chain containing only aliphatic carbon atoms

Family

Application62/168,529Us provisional application · filed 29 May 2015

Application62/168,581Us provisional application · filed 29 May 2015

Application62/269,745Us provisional application · filed 18 Dec 2015

Application15/167,373Parent of this continuation · filed 27 May 2016

US 2018/0127378 A1Pre-grant publication · published 10 May 2018

US 9,796,683 B2Parent of this continuation

US 2016/0347717 A1Published application

US 10,851,065 B2This patent

From the US filing history. Foreign family members aren’t listed.