US 11,834,467 B2Granted

Substituted indazoles as hematopoietic progenitor kinase 1 (HPK1) inhibitors

Assignee1ST Biotherapeutics, Inc.

InventorsJinhwa Lee, Suyeon Jo, Keonseung Lim, A Yeong Park, Gadhe Changdev Gorakshnath, Hwajung Nam, Yeonguk Jeon, Yejin Hwang, Jae Eun Kim, Misoon Kim, Seung Mook Lim

Life of this patent

Estimating the term…

Abstract

The present disclosure provides a compound of Formula (I) or pharmaceutically acceptable salts thereof, a composition comprising the compound, methods of using the compound for the treatment of various disorders associated with HPK1, and methods of preparing these compounds.

Claims24

Dependent claims

A compound of Formula (I):

or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof,
wherein:
R1 is alkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
wherein the alkyl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR6C(O)R9, NR6C(O)NR10R11, NR6C(O)OR9, NR6NR10R11, NR6OR9, NR6S(O)2R9, NR6S(O)2NR10R11, OR9, OC(O)R9, OC(O)NR10R11, ═O, P(O)R12R13, SR9, S(O)R9, S(O)(NH)R10, S(O)2R9, S(O)2NR10R11, cycloalkyl, heterocyclyl, aryl, and heteroaryl;
and
wherein the cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected R7 substituents;
each R7 is independently halo, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR6C(O)R9, NR6C(O)NR10R11, NR6C(O)OR9, NR6NR10R11, NR6OR9, NR6S(O)2R9, NR6S(O)2NR10R11, OR9, OC(O)R9, OC(O)NR10R11, ═O, P(O)R12R13, SR9, S(O)R9, S(O)(NH)R10, S(O)2R9, S(O)2NR10R11, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
L is a bond, —NR6—, —O—, or —S—;
X is O or S;
Het is:
Ra is H, D, halo, CN, CH2F, CHF2, CF3, NR10R11, or OR9;
Rb is H, D, halo, CN, CH2F, CHF2, CF3, NR10R11, or OR9;
Rc is H, D, halo, CN, CH2F, CHF2, CF3, NR10R11, or OR9;
R2 is H, D, halo, CN, NO2, CD3, CD2OH, CH2OCH[Si(CH3)3]CH3, CH2OCH2CH2Si(CH3)3, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR6C(O)R9, NR6C(O)NR10R11, NR6C(O)OR9, NR6NR10R11, NR6OR9, NR6S(O)2R9, NR6S(O)2NR10R11, OR9, OC(O)R9, OC(O)NR10R11, P(O)R12R13, SR9, S(O)R9, S(O)(NH)R10, S(O)2R9, S(O)2NR10R11, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
wherein the C1-6 alkyl, C2-6 alkenyl, or C2-6 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, NO2, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
and
wherein the cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, NO2, alkyl, haloalkyl, hydroxyalkyl, alkenyl, alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
R3 is H, D, halo, CN, NO2, CD3, CH2OH, CD2OH, C1-6 alkyl, haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR6C(O)R9, NR6C(O)NR10R11, NR6C(O)OR9, NR6NR10R11, NR6OR9, NR6S(O)2R9, NR6S(O)2NR10R11, OR9, OC(O)R9, OC(O)NR10R11, P(O)R12R13, SR9, S(O)R9, S(O)(NH)R10, S(O)2R9, S(O)2NR10R11, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
R5 is H, D, halo, CN, CD3, CH2OH, CD2OH, C1-6 alkyl, haloalkyl, C2-6 alkenyl, C2-6 alkynyl, OH, or cycloalkyl;
M is a bond, —NR6—, —O—, or —S—;
each R6 is independently H or C1-6 alkyl;
R4 is H, D, halo, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, OH, P(O)R12R13, S(O)(NH)R10, S(O)2R9, S(O)2NR10R11, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
wherein the C1-6 alkyl, C2-6 alkenyl, or C2-6 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halo, CN, NO2, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, NR10S(O)2R9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
and
wherein the cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, NO2, CD3, alkyl, haloalkyl, hydroxyalkyl, alkenyl, alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, NR10S(O)2R9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
each R10 is independently H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
each R11 is independently H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
or
each R10 and R11, taken together with the nitrogen atom to which they are attached, independently form a 4- to 12-membered heterocyclyl, wherein the 4- to 12-membered heterocyclyl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, NO2, alkyl, haloalkyl, hydroxyalkyl, alkenyl, alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
each R12 is independently C1-6 alkyl, OC1-6 alkyl, C3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl;
each R13 is independently C1-6 alkyl, OC1-6 alkyl, C3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl;
or
each R12 and R13, taken together with the phosphorus atom to which they are attached, independently form a 4- to 8-membered heterocyclyl, wherein the 4- to 8-membered heterocyclyl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, NO2, alkyl, haloalkyl, hydroxyalkyl, alkenyl, alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
and
each R9 is independently H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl.

32 more elements

A compound selected from the group consisting of:

(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(methyl(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)amino)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-((2H-tetrazol-2-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-(1-(2H-tetrazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-((1H-imidazol-1-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-((1H-pyrrol-1-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-((1H-pyrazol-1-yl)methyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((2-methyl-1H-imidazol-1-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-7-(cyclopropyl(methoxy)methyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((2-methyl-1H-pyrrol-1-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((4-methyl-1H-imidazol-1-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((4-methyl-1H-pyrazol-1-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-((R)-1-(1H-tetrazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-((S)-1-(1H-tetrazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-(1-(2H-1,2,3-triazol-2-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-(1-(1H-1,2,4-triazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(hydroxy(tetrahydro-2H-pyran-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-(1-(1H-pyrazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(4-methyl-1H-imidazol-1-yl)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-7-(1-((1-cyanocyclopropyl)amino)ethyl)-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(9H-fluoren-9-yl)methyl(5-chloro-6-fluoro-4-(2-((1S,2S)-2-fluorocyclopropane-1-carboxamido)imidazo[1,2-a]pyrazin-6-yl)-1H-indazol-7-yl)carbamate;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(4-methyl-1H-pyrazol-1-yl)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(7-(1-(1H-imidazol-1-yl)ethyl)-5-chloro-6-fluoro-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(2-methyl-1H-imidazol-1-yl)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((E)-3-(triethylsilyl)prop-1-en-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(3-(trimethylsilyl)prop-2-yn-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide-1 formic acid;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-hydroxy-3-(trimethylsilyl)prop-2-yn-1-yl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide-1 formic acid;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((methylthio)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(methylthio)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((methylsulfinyl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-((methylsulfonyl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(methylsulfonyl)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide;
and
(1S,2S)—N-(6-(5-chloro-6-fluoro-7-(1-(methylsulfinyl)ethyl)-1H-indazol-4-yl)imidazo[1,2-a]pyrazin-2-yl)-2-fluorocyclopropane-1-carboxamide,
or a pharmaceutically acceptable salt or tautomer thereof.

31 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/485,653Filed 27 Sep 2021 · us provisional application
Priority: 28 Sep 2020
Published: US 2022/0098219 A131 Mar 2022
Granted: 5 Dec 2023
Term ends: Not estimatedThe source records don’t support an estimate.

Classification16 codes

C07F 7/0812
Comprising at least one atom selected from the elements N, O, halogen, S, Se or Te: comprising a heterocyclic ring
A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents
A61P 35/00
Antineoplastic agents
A61P 37/00
Drugs for immunological or allergic disorders

Family

Application63/084,059Us provisional application · filed 28 Sep 2020
US 2022/0098219 A1Pre-grant publication · published 31 Mar 2022
US 11,834,467 B2This patent

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

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Abstract

A compound of Formula (I):

or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof,
wherein:
R1 is alkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
wherein the alkyl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR6C(O)R9, NR6C(O)NR10R11, NR6C(O)OR9, NR6NR10R11, NR6OR9, NR6S(O)2R9, NR6S(O)2NR10R11, OR9, OC(O)R9, OC(O)NR10R11, ═O, P(O)R12R13, SR9, S(O)R9, S(O)(NH)R10, S(O)2R9, S(O)2NR10R11, cycloalkyl, heterocyclyl, aryl, and heteroaryl;
and
wherein the cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected R7 substituents;
each R7 is independently halo, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR6C(O)R9, NR6C(O)NR10R11, NR6C(O)OR9, NR6NR10R11, NR6OR9, NR6S(O)2R9, NR6S(O)2NR10R11, OR9, OC(O)R9, OC(O)NR10R11, ═O, P(O)R12R13, SR9, S(O)R9, S(O)(NH)R10, S(O)2R9, S(O)2NR10R11, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
L is a bond, —NR6—, —O—, or —S—;
X is O or S;
Het is:
Ra is H, D, halo, CN, CH2F, CHF2, CF3, NR10R11, or OR9;
Rb is H, D, halo, CN, CH2F, CHF2, CF3, NR10R11, or OR9;
Rc is H, D, halo, CN, CH2F, CHF2, CF3, NR10R11, or OR9;
R2 is H, D, halo, CN, NO2, CD3, CD2OH, CH2OCH[Si(CH3)3]CH3, CH2OCH2CH2Si(CH3)3, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR6C(O)R9, NR6C(O)NR10R11, NR6C(O)OR9, NR6NR10R11, NR6OR9, NR6S(O)2R9, NR6S(O)2NR10R11, OR9, OC(O)R9, OC(O)NR10R11, P(O)R12R13, SR9, S(O)R9, S(O)(NH)R10, S(O)2R9, S(O)2NR10R11, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
wherein the C1-6 alkyl, C2-6 alkenyl, or C2-6 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, NO2, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
and
wherein the cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, NO2, alkyl, haloalkyl, hydroxyalkyl, alkenyl, alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
R3 is H, D, halo, CN, NO2, CD3, CH2OH, CD2OH, C1-6 alkyl, haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR6C(O)R9, NR6C(O)NR10R11, NR6C(O)OR9, NR6NR10R11, NR6OR9, NR6S(O)2R9, NR6S(O)2NR10R11, OR9, OC(O)R9, OC(O)NR10R11, P(O)R12R13, SR9, S(O)R9, S(O)(NH)R10, S(O)2R9, S(O)2NR10R11, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
R5 is H, D, halo, CN, CD3, CH2OH, CD2OH, C1-6 alkyl, haloalkyl, C2-6 alkenyl, C2-6 alkynyl, OH, or cycloalkyl;
M is a bond, —NR6—, —O—, or —S—;
each R6 is independently H or C1-6 alkyl;
R4 is H, D, halo, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, OH, P(O)R12R13, S(O)(NH)R10, S(O)2R9, S(O)2NR10R11, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
wherein the C1-6 alkyl, C2-6 alkenyl, or C2-6 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halo, CN, NO2, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, NR10S(O)2R9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
and
wherein the cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, NO2, CD3, alkyl, haloalkyl, hydroxyalkyl, alkenyl, alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, NR10S(O)2R9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
each R10 is independently H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
each R11 is independently H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
or
each R10 and R11, taken together with the nitrogen atom to which they are attached, independently form a 4- to 12-membered heterocyclyl, wherein the 4- to 12-membered heterocyclyl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, NO2, alkyl, haloalkyl, hydroxyalkyl, alkenyl, alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
each R12 is independently C1-6 alkyl, OC1-6 alkyl, C3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl;
each R13 is independently C1-6 alkyl, OC1-6 alkyl, C3-8 cycloalkyl, heterocyclyl, aryl, or heteroaryl;
or
each R12 and R13, taken together with the phosphorus atom to which they are attached, independently form a 4- to 8-membered heterocyclyl, wherein the 4- to 8-membered heterocyclyl is optionally substituted with one or more substituents independently selected from the group consisting of halo, CN, NO2, alkyl, haloalkyl, hydroxyalkyl, alkenyl, alkynyl, C(O)R9, C(O)NR10R11, C(O)OR9, NR10R11, NR10C(O)R9, NR10C(O)NR10R11, NR10C(O)OR9, OR9, OC(O)R9, OC(O)NR10R11, and OC(O)OR9;
and
each R9 is independently H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl.

32 more elements

Facts

Application

17/485,653Filed 27 Sep 2021 · us provisional application

Priority

28 Sep 2020

Published

US 2022/0098219 A131 Mar 2022

Granted

5 Dec 2023

Term ends

Not estimatedThe source records don’t support an estimate.

Classification16 codes

C07F 7/0812
Comprising at least one atom selected from the elements N, O, halogen, S, Se or Te: comprising a heterocyclic ring
A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents
A61P 35/00
Antineoplastic agents
A61P 37/00
Drugs for immunological or allergic disorders