US 12,404,248 B2Granted

IRE1 small molecule inhibitors

AssigneeCornell University

InventorsJoseph P. Vacca, Sarah Elizabeth Bettigole

Life of this patent

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Abstract

Provided herein are small molecule inhibitors for the targeting or IRE1 protein family members. Binding may be direct or indirect. Further provided herein are methods of using IRE1 small molecule inhibitors for use in treating or ameliorating cancer in a subject. Moreover, IRE1 small molecule inhibitors described herein are for the treatment of cancer, where the cancer is a solid or hematologic cancer.

Claims27

Dependent claims

A method to treat cancer, the method comprising administering to a subject in need thereof a compound, or a pharmaceutically acceptable salt or solvate thereof, of Formula (I), or a pharmaceutically acceptable salt, or solvate thereof, or a pharmaceutical composition thereof

wherein,
is C3-C10cycloalkyl;
each R1 is independently —OR6a, —SR6a, —S(═O)R7, —S(═O)2R7, or —N(R6b)2;
each R2 is independently halogen, —CN, -OR8a, —SR8a, —S(═O)R9, —S(═O)2R9, —S(═O)2N(R8b)2, —NR8aS(═O)2R9, —C(═O)R9, —OC(═O)R9, —CO2R8a, —OCO2R9, —N(R8b)2, —OC(═O)N(R8b)2, —NR8aC(═O)R9, —NR8aC(═O)OR9, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
Y5 is CR4,
Y1, Y2, Y3, and Y4 are each independently selected from N and CR5 with the proviso that no more than two of Y1, Y2, Y3, and Y4 are N;
each R6a is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C1-C4fluoroalkyl, -X-optionally substituted C1-C4alkyl, -X-optionally substituted C1-C4heteroalkyl, -X-optionally substituted C1-C4fluoroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C3-C4cycloalkylC1-C3alkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R6b is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C1-C4fluoroalkyl, -X-optionally substituted C1-C4alkyl, -X-optionally substituted C1-C4heteroalkyl, -X-optionally substituted C1-C4fluoroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C3-C4cycloalkylC1-C3alkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
or two R6b are taken together with the N atom to which they are attached to form an optionally substituted heterocycle;
X is —C(═O)—;
each R7 is independently optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R8a is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R8b is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
or two R8b are taken together with the N atom to which they are attached to form an optionally substituted heterocycle;
each R9 is independently optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, or optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
A2 is N or CRA;
RA is H, halogen, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted aryl, or —OR10;
RA1, RA2, RA3 and RA4 are each independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, or optionally substituted aryl;
R10 is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
is phenylene or a 6-membered heteroarylene ring comprising 1 or 2 nitrogen atoms in the ring;
B is
each R3 is independently halogen, —CN, -OR11, —SR11, —N(R11)2, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R11 is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
n is 0, 1, 2, 3, or 4;
p is 1, 2, or 3;
q is 0, 1, 2, or 3;
R4 and each R5 are each independently H, halogen, —CN, -OR12, —SR12, —N(R12)2, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
and
R12 is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl.

26 more elements

A method to treat cancer, the method comprising administering to a subject in need thereof a compound, or a pharmaceutically acceptable salt or solvate thereof, wherein the compound is:

N-(4-(2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)ethyl)phenyl)-2-chlorobenzenesulfonamide;
N-(6-((E)-2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)vinyl)pyridazin-3-yl)-2-chlorobenzenesulfonamide;
N-(4-((E)-2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)vinyl)-2-fluorophenyl)-2-chlorobenzenesulfonamide;
N-(4-((E)-2-(2-(((1r,4r)-4-aminocyclohexyl)amino)-4-propylpyrimidin-5-yl)vinyl) phenyl)-2-chlorobenzenesulfonamide;
N-(4-((E)-2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)vinyl)-3-methylphenyl)-2-chlorobenzenesulfonamide;
N-(4-(2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)ethyl)-3-methylphenyl)-2-chlorobenzenesulfonamide;
N-(6-(2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)ethyl)pyridazin-3-yl)-2-chlorobenzenesulfonamide;
N-(4-(2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)ethyl)-2-fluorophenyl)-2-chlorobenzenesulfonamide;
N-(5-((E)-2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methoxypyridin-2-yl)-2-chlorobenzenesulfonamide;
N-(5-(2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)ethyl)-6-methoxypyridin-2-yl)-2-chlorobenzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-hydroxycyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methoxypyridin-2-yl)benzenesulfonamide;
2-chloro-N-(5-(2-(2-(((1r,4r)-4-hydroxycyclohexyl)amino)pyrimidin-5-yl)ethyl)-6-methoxypyridin-2-yl)benzenesulfonamide;
N-(5-(2-(6-(((1r,4r)-4-aminocyclohexyl)amino)pyridin-3-yl)ethyl)-6-methoxypyridin-2-yl)-2-chlorobenzenesulfonamide;
N-(4-((E)-2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)vinyl)-3-methoxyphenyl)-2-chlorobenzenesulfonamide;
N-(4-(2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)ethyl)-3-methoxyphenyl)-2-chlorobenzenesulfonamide;
N-(6-(2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)ethyl)-5-ethylpyridin-3-yl)-2-chlorobenzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methoxypyridin-2-yl)benzenesulfonamide;
N-(6-(2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)ethyl)-5-methoxypyridin-3-yl)-2-chlorobenzenesulfonamide;
2-chloro-N-(5-(2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)ethyl)-6-methoxypyridin-2-yl)benzenesulfonamide;
2-chloro-N-(5-(2-(2-(((1r,4r)-4-hydroxycyclohexyl)amino)pyrimidin-5-yl)ethyl)-6-methylpyridin-2-yl)benzenesulfonamide;
2-chloro-N-(5-(2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)ethyl)-6-methylpyridin-2-yl)benzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-3-fluoro-6-methylpyridin-2-yl)benzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methylpyridin-2-yl)benzenesulfonamide;
2-chloro-N-(5-(2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)ethyl)-3-fluoro-6-methylpyridin-2-yl)benzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-3-fluoro-6-methylpyridin-2-yl)benzenesulfonamide;
2-chloro-N-(4-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-3-methylphenyl)benzenesulfonamide;
2-chloro-N-(4-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-3-fluoro-5-methylphenyl)benzenesulfonamide;
2-chloro-N-(4-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-2-fluoro-5-methylphenyl)benzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-ethylpyridin-2-yl)benzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(diethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methylpyridin-2-yl)benzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methylpyridin-2-yl)-4-fluorobenzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methoxypyridin-2-yl)-4-fluorobenzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methylpyridin-2-yl)-3-fluorobenzenesulfonamide;
2-chloro-N-(4-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl) phenyl)benzenesulfonamide;
2-chloro-N-(4-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-2-fluorophenyl)benzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl) pyridin-2-yl)benzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl) pyrazin-2-yl)benzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methylpyridin-2-yl)-3,4-difluorobenzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methoxypyridin-2-yl)-3-fluorobenzenesulfonamide;
2-chloro-N-(5-(2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)pyrimidin-2-yl)benzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methoxypyridin-2-yl)-3,4-difluorobenzenesulfonamide;
4-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-ethylpyridin-2-yl) pyridine-3-sulfonamide;
4-chloro-N-(5-(2-(2-(((1r, 4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-4-methoxypyrimidin-2-yl) pyridine-3-sulfonamide;
2-chloro-N-(6-methyl-5-(2-(2-(((1r,4r)-4-(methylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl) pyridin-2-yl)benzenesulfonamide;
N-(5-(2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-ethylpyridin-2-yl)-2-chlorobenzenesulfonamide;
N-(5-((E)-2-(2-(((1r,4r)-4-aminocyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methylpyridin-2-yl)-2-chlorobenzenesulfonamide;
2-chloro-N-(6-ethyl-5-((E)-2-(2-(((1r,4r)-4-(methylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl) pyridin-2-yl)benzenesulfonamide;
2-chloro-N-(6-methoxy-5-((E)-2-(2-(((1r,4r)-4-(methylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)pyridin-2-yl)benzenesulfonamide;
(E)-N-(5-(2-(2-((4-aminobicyclo[2.2.2]octan-1-yl)amino)pyrimidin-5-yl)vinyl)-6-methylpyridin-2-yl)-2-chlorobenzenesulfonamide;
2-chloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-3-fluoro-6-methoxypyridin-2-yl)benzenesulfonamide;
or
2,3-dichloro-N-(5-((E)-2-(2-(((1r,4r)-4-(dimethylamino)cyclohexyl)amino)pyrimidin-5-yl)vinyl)-6-methoxypyridin-2-yl)benzenesulfonamide.

49 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/411,842Filed 12 Jan 2024 · continuation
Priority: 3 Dec 2018
Published: US 2024/0287004 A129 Aug 2024
Granted: 2 Sep 2025
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 239/42
One oxygen, sulfur or nitrogen atom: one nitrogen atom
A61P 35/00
Antineoplastic agents
C07D 213/76
Nitrogen atoms: to which a second hetero atom is attached
C07D 239/69
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon…

Family

Application62/774,789Us provisional application · filed 3 Dec 2018
PCT/US2019/063920Parent of this continuation · filed 2 Dec 2019
US 2024/0287004 A1Pre-grant publication · published 29 Aug 2024
Application17/296,771Parent of this continuation
US 11,945,784 B2Parent of this continuation
US 2022/0024878 A1Published application
US 12,404,248 B2This patent

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

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Abstract

wherein,
is C3-C10cycloalkyl;
each R1 is independently —OR6a, —SR6a, —S(═O)R7, —S(═O)2R7, or —N(R6b)2;
each R2 is independently halogen, —CN, -OR8a, —SR8a, —S(═O)R9, —S(═O)2R9, —S(═O)2N(R8b)2, —NR8aS(═O)2R9, —C(═O)R9, —OC(═O)R9, —CO2R8a, —OCO2R9, —N(R8b)2, —OC(═O)N(R8b)2, —NR8aC(═O)R9, —NR8aC(═O)OR9, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
Y5 is CR4,
Y1, Y2, Y3, and Y4 are each independently selected from N and CR5 with the proviso that no more than two of Y1, Y2, Y3, and Y4 are N;
each R6a is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C1-C4fluoroalkyl, -X-optionally substituted C1-C4alkyl, -X-optionally substituted C1-C4heteroalkyl, -X-optionally substituted C1-C4fluoroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C3-C4cycloalkylC1-C3alkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R6b is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C1-C4fluoroalkyl, -X-optionally substituted C1-C4alkyl, -X-optionally substituted C1-C4heteroalkyl, -X-optionally substituted C1-C4fluoroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C3-C4cycloalkylC1-C3alkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
or two R6b are taken together with the N atom to which they are attached to form an optionally substituted heterocycle;
X is —C(═O)—;
each R7 is independently optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R8a is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R8b is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
or two R8b are taken together with the N atom to which they are attached to form an optionally substituted heterocycle;
each R9 is independently optionally substituted C1-C4alkyl, optionally substituted C1-C4heteroalkyl, or optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
A2 is N or CRA;
RA is H, halogen, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted aryl, or —OR10;
RA1, RA2, RA3 and RA4 are each independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, or optionally substituted aryl;
R10 is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
is phenylene or a 6-membered heteroarylene ring comprising 1 or 2 nitrogen atoms in the ring;
B is
each R3 is independently halogen, —CN, -OR11, —SR11, —N(R11)2, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
each R11 is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
n is 0, 1, 2, 3, or 4;
p is 1, 2, or 3;
q is 0, 1, 2, or 3;
R4 and each R5 are each independently H, halogen, —CN, -OR12, —SR12, —N(R12)2, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl;
and
R12 is independently H, optionally substituted C1-C4alkyl, optionally substituted C1-C4fluoroalkyl, optionally substituted C1-C4heteroalkyl, optionally substituted C3-C6cycloalkyl, optionally substituted C2-C10heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl.

26 more elements

Facts

Application

18/411,842Filed 12 Jan 2024 · continuation

Priority

3 Dec 2018

Published

US 2024/0287004 A129 Aug 2024

Granted

2 Sep 2025

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 239/42
One oxygen, sulfur or nitrogen atom: one nitrogen atom
A61P 35/00
Antineoplastic agents
C07D 213/76
Nitrogen atoms: to which a second hetero atom is attached
C07D 239/69
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon…

Family

Application62/774,789Us provisional application · filed 3 Dec 2018

PCT/US2019/063920Parent of this continuation · filed 2 Dec 2019

US 2024/0287004 A1Pre-grant publication · published 29 Aug 2024

Application17/296,771Parent of this continuation

US 11,945,784 B2Parent of this continuation

US 2022/0024878 A1Published application

US 12,404,248 B2This patent

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