US 2025/0100996 A1Published application

Heterocycloalkyl and heteroaryl compounds and pharmaceutical compositions that modulate ikzf2

AssigneePlexium, Inc.

InventorsPengyu YANG, Simon BAILEY

Life of this patent

Estimating the term…

Abstract

Disclosed are compounds I-A and I-B and salts thereof that bind to and modulate cereblon activity. In some embodiments, the binding and modulation of cereblon results in the degradation of IKAROS family zinc finger proteins (e.g., IKZF2).

Claims44

Dependent claims

A compound of formula I-A:

or a pharmaceutically acceptable salt, solvate, stereoisomer, or tautomer thereof, wherein:
m is zero, one, two, or three;
n is zero, one, or two;
q is one, two, or three;
s is one;
L1 is CH2 or a covalent bond;
Q is selected from —C(O)NR5R6 or a 4- to 10-member heterocyclic group having one or more heteroatoms independently selected from NR20, O, S, and SO2, where R20 is —[C(O)]wR7, S(O)2R7, or a covalent bond linking said heterocyclic group to ring A, wherein said heterocyclic group is independently unsubstituted or substituted with C(O)R7, or with one to five R8, and where w is 0 or 1;
T is CH2, CH(R2), C(R2)2, or N, provided that when T is N, L1 is attached to T;
X is hydrogen, deuterium, or fluoro;
Y is a covalent bond, —O—, or —NR—;
Z and Z1 are each independently CR1 or N;
ring A is phenyl or a 4- to 7-membered nitrogen containing heterocyclyl, wherein ring A is independently unsubstituted or substituted with one to five R8;
R is hydrogen or C1-C4 alkyl;
each R1 is independently hydrogen, halo, cyano, hydroxy, —N(R9)2, C1-C4 alkyl independently unsubstituted or substituted with from one to three R10, or C1-C6 alkoxy independently unsubstituted or substituted with from one to three R10;
or
when Z1 is CR1, then two adjacent R1 together with the carbon atoms to which they are attached form a C3-C7 cycloalkyl, a C6-C10 aryl, a 4- to 7-membered heterocycloalkenyl, or a 5- to 6-membered heteroaryl, wherein each of said cycloalkyl, heterocycloalkenyl, aryl, and heteroaryl are independently substituted with one to three R11;
each R2 is independently selected from halo, cyano, hydroxy, —N(R9)2, C1-C4 alkyl independently unsubstituted or substituted with from one to three R10, and C1-C4 alkoxy independently unsubstituted or substituted with from one to three R10;
R3 is selected from the group consisting of hydrogen, amino, halo, cyano, hydroxy, C1-C6 alkyl, and C1-C6 haloalkyl;
R4 is hydrogen or —CH2—OR12;
R5 and R6, together with the nitrogen to which they are attached, form a 4- to 7-membered heterocyclyl, wherein said heterocyclyl is independently unsubstituted or substituted with one to five R8;
R7 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C3-C7 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, 4- to 7-membered heterocyclyl, C6-C10 aryl, 5- to 10-membered heteroaryl, or —N(R8)2;
wherein said alkyl, alkoxy, cycloalkyl, alkenyl, alkynyl, heterocyclyl, aryl, or heteroaryl is further independently unsubstituted or substituted with one to five R8;
each R8 is independently halo, cyano, hydroxy, —SH, —NH2, —NO2, —SF5, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C10 cycloalkyl, heterocyclyl, aryl, or heteroaryl;
each R9 is independently H or C1-C4 alkyl independently unsubstituted or substituted with from 1 to 3 substituents selected from halo, cyano, hydroxy, and C1-C4 alkoxy, or two R9 together with the nitrogen atom to which they are attached form a 3- to 7-membered heterocycloalkyl or 5- to 6-membered heteroaryl;
each R10 is independently —N(R9)2, halo, cyano, hydroxy, or C1-C4 alkoxy;
each R11 is independently —N(R9)2, halo, cyano, hydroxy, or oxo;
R12 is —C(O)—R13 or —P(O)(OR14)2;
R13 is C1-C4 alkyl or C1-C4 alkoxy;
and
each R14 is independently H or C1-C4 alkyl.

27 more elements

A compound of formula I-B:

or a pharmaceutically acceptable salt, solvate, stereoisomer, and/or tautomer thereof,
wherein:
m40, n40 and p40 are independently zero, one, two, or three;
q40 is one, two or three;
r40 is zero, one, or two;
s40 is zero when r40 is not zero and is one when r40 is zero;
t40 is zero or one;
X40 is hydrogen, deuterium, or fluoro;
Y40 is oxygen or NR40 where R40 is hydrogen or C1-C4 alkyl;
Z40 and Z41 are each independently CR41 or N;
each R41 is independently selected from hydrogen, amino, (C1-C4 alkyl)amino unsubstituted or substituted with from one to three R45 substituents, di-(C1-C4 alkyl)amino unsubstituted or substituted with from one to three R45 substituents on each alkyl group, cyano, halo, hydroxyl, C1-C4 alkyl unsubstituted or substituted with from one to three R45 substituents, and C1-C4 alkoxy unsubstituted or substituted with from one to three R45 substituents;
or
when Z41 is CR41, then two adjacent R41 together with the carbon atoms to which they are attached form a C3-C7 cycloalkyl, a C6-C10 aryl, a 4- to 7-membered heterocycloalkenyl having from one to three heteroatoms selected from oxygen, nitrogen, or sulfur, or a 5- to 6-membered heteroaryl having 1 to 3 heteroatoms selected from oxygen, nitrogen, or sulfur wherein each of said cycloalkyl, heterocycloalkenyl, aryl, and heteroaryl are independently substituted with one to three R46 groups;
each R42 is independently selected from cyano, halo, hydroxyl, amino, C1-C4 alkylamino unsubstituted or substituted with from one to three R45 substituents, di-(C1-C4 alkyl)amino unsubstituted or substituted with from one to three R45 substituents on each alkyl group, C1-C4 alkyl unsubstituted or substituted with from one to three R45 substituents, and C1-C4 alkoxy unsubstituted or substituted with from one to three R45 substituents;
R43 is C5-C10 heteroaryl having from 1 to 3 heteroatoms selected from O, N, and/or S and unsubstituted or substituted with 1 to 3 R47 substituents;
R44 is selected from hydrogen and —CH2—OR48 where R48 is C(O)—R49 or —P(O)(OR50)2, where R49 is C1-C4 alkyl or C1-C4 alkoxy, and where each of R50 is independently H or C1-C4 alkyl;
each R45 is independently amino, (C1-C4 alkyl)amino, di-(C1-C4 alkyl)amino, cyano, halo, hydroxyl, or C1-C4 alkoxy;
each R46 is independently selected from amino, (C1-C4 alkyl)amino, di-(C1-C4 alkyl)amino, cyano, halo, hydroxyl, and oxo;
each R47 is independently selected from amino, C1-C4 alkyl unsubstituted or substituted with 1 to 3 halo, C1-C4 alkoxy, (C1-C4 alkyl)amino, di-(C1-C4 alkyl)amino, cyano, halo, hydroxyl, nitro, C5-C6 heteroaryl having from 1 to 3 heteroatoms selected from O, NR40, and/or S, C3-C7 cycloalkyl, and —C(O)CH3;
and
R51 is hydroxyl, cyano, halo, or C1-C4 alkyl unsubstituted or substituted with 1 to 3 halo.

18 more elements

A compound, or a pharmaceutically acceptable salt, solvate, stereoisomer, or tautomer thereof,

wherein the compound is selected from:
#
Structure
Nomenclature
1-A
3-(1-oxo-5-(((1S,2S)-2-(3- (tetrahydro-2H-pyran-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
2-A
3-(1-oxo-5-(((1R,2R)-2-(3- (tetrahydro-2H-pyran-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
3-A
3-(1-oxo-5-(((1R,2S)-2-(3- (tetrahydro-2H-pyran-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
4-A
3-(1-oxo-5-(((1S,2R)-2-(3- (tetrahydro-2H-pyran-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
5-A
3-(5-(((1S,2S)-2-(3-(4,4- dimethylpiperidin-1-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
6-A
3-(5-(((1S,2S)-2-(3-(4,4- difluoropiperidin-1-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxo-isoindolin-2-yl)- piperidine-2,6-dione
7-A
3-(5-(((1S,2S)-2-(3-morpho- linoazetidin-1-yl)cyclohex- yl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
8-A
3-(5-(((1S,2S)-2-(3-(3,6- dihydro-2H-pyran-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
9-A
3-(5-(((1S,2S)-2-(3-(1,1- dioxidotetrahydro-2H-thio- pyran-4-yl)-azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
10-A
3-(1-oxo-5-(((1S,2S)-2-(3- (piperidin-4-yl)azetidin-1- yl)cyclohexyl)oxy)isoin- dolin-2-yl)piperidine-2,6- dione
11-A
3-(5-(((1S,2S)-2-(3-(1-meth- ylpiperidin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
12-A
3-(5-(((1S,2S)-2-(3-(1-acet- ylpiperidin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
13-A
3-(5-(((1S,2S)-2-(3-hydroxy- 3-(tetrahydro-2H-pyran-4- yl)azetidin-1-yl)cyclohex- yl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
14-A
3-(1-oxo-5-(((1S,2S)-2-(3- (tetrahydrofuran-3-yl)azeti- din-1-yl)cyclohexyl)oxy)- isoindolin-2-yl)piperidine- 2,6-dione
15-A
3-(5-(((1S,2S)-2-(3-(oxetan- 3-yl)azetidin-1-yl)cyclohex- yl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
16-A
3-(1-oxo-5-(((1S,2S)-2-(3- (piperidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoin- dolin-2-yl)piperidine-2,6- dione
17-A
3-(5-(((1S,2S)-2-(3-(1-meth- ylpiperidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
18-A
3-(5-(((1S,2S)-2-(3-(1-acet- ylpiperidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
19-A
3-(1-oxo-5-(((1S,2S)-2-(3- (piperidin-3-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)-piperidine-2,6-dione
20-A
3-(5-(((1S,2S)-2-(3-(1-meth- ylpiperidin-3-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
21-A
3-(5-(((1S,2S)-2-(3-(1-acet- ylpiperidin-3-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
22-A
3-(1-oxo-5-((2-(3-(piperi- dine-1-carbonyl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
23-A
3-(1-oxo-5-((2-(3-(piperi- dine-1-carbonyl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
24-A
3-(5-{[(1S,2S)-2-13-(1-benz- oylpiperidin-4-yl)azetidin-1- yl]cyclohexyl]oxy}-1-oxo- 2,3-dihydro-1H-isoindol-2- yl)piperidine-2,6-dione
25-A
3-(5-{[(1S,2S)-2-{3-[1-(1- methylcyclobutanecarbon- yl)piperidin-4-yl]azetidin-1- yl}cyclohexyl]oxy}-1-oxo- 2,3-dihydro-1H-isoindol-2- yl)piperidine-2,6-dione
26-A
tert-butyl 4-{1-[(1S,2S)-2- {[2-(2,6-dioxopiperidin-3- yl)-1-oxo-2,3-dihydro-1H- isoindol-5-yl]oxy}cyclohex- yl]azetidin-3-yl}piperidine- 1-carboxylate
27-A
1-(4-(1-((1S,2S)-2-((2-(2,6- dioxopiperidin-3-yl)-1-oxo- isoindolin-5-yl)oxy)cyclo- hexyl)azetidin-3-yl)piperi- dine-1-carbonyl)cyclopro- pane-1-carbonitrile
28-A
3-(5-(((1S,2S)-2-(3-(1-(3- methylbicyclo[1.1.1]pentane- 1-carbonyl)piperidin-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
29-A
3-(5-(((1S,2S)-2-(3-(1-(3- methyloxetane-3-carbonyl)- piperidin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
30-A
1-(4-(1-((1S,2S)-2-((2-(2,6- dioxopiperidin-3-yl)-1-oxo- isoindolin-5-yl)oxy)cyclohex- yl)azetidin-3-yl)piperidine-1- carbonyl)cyclobutane-1- carbonitrile
31-A
3-(5-(((1S,2S)-2-(3-(1-(1- methylcyclopropane-1- carbonyl)piperidin-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
32-A
3-(5-(((1S,2S)-2-(3-(1- (3,3-difluorocyclobutane- 1-carbonyl)piperidin-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
33-A
3-(5-(((1S,2S)-2-(3-(1-(1- methylcyclopentane-1- carbonyl)piperidin-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
34-A
3-(5-(((1S,2S)-2-(3-(1-(2- cyclopropylacetyl)piperidin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
35-A
3-(5-(((1S,2S)-2-(3-(1-(2- methylcyclopropane-1- carbonyl)piperidin-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
36-A
3-(5-(((1S,2S)-2-(1′-(1-meth- ylcyclobutane-1-carbonyl)- [4,4′-bipiperidin]-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
38-A
3-(1-oxo-5-(((1R,2S)-2-(4- (pyrrolidine-1-carbonyl)- piperidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
39-A
3-(5-(((1R,2S)-2-(3-(morph- oline-4-carbonyl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
40-A
4-((4-(2-(2,6-dioxopiperidin- 3-yl)-1-oxoisoindolin-5-yl)- 4-hydroxypiperidin-1-yl)- methyl)-N,N-dimethylpiperi- dine-1-carboxamide
41-A
1-(4-((4-(2-(2,6-dioxopiperi- din-3-yl)-1-oxoisoindolin-5- yl)-4-hydroxypiperidin-1-yl)- methyl)phenyl)-N,N-dimeth- ylpiperidine-4-carboxamide
42-A
3-(5-(((1S,2S)-2-(3-(1-(1- fluorocyclopropane-1- carbonyl)piperidin-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
43-A
3-(5-(((1S,2S)-2-(3-(1-((1- methylcyclobutyl)sulfonyl)- piperidin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
44-A
3-(5-(((1S,2R)-3,3-difluoro- 2-(3-(1-(1-methylcyclo- butane-1-carbonyl)piperidin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
45-A
3-(5-(((1S,2R)-3,3-difluoro- 2-(3-(1-(1-methylcyclopro- pane-1-carbonyl)piperidin-4- yl)azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
46-A
3-(5-(((1S.2R)-3,3-difluoro- 2-(3-(1-(1-methylcyclopen- tane-1-carbonyl)piperidin-4- yl)azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
47-A
3-(5-(((1S,2R)-2-(3-(1-(3,3- difluorocyclobutane-1- carbonyl)piperidin-4-yl)- azetidin-1-yl)-3,3-difluoro- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
48-A
3-(5-(((1S,2R)-2-(3-(1-(2- cyclopropylacetyl)piperi- din-4-yl)azetidin-1-yl)-3,3- difluorocyclohexyl)oxy)- 1-oxoisoindolin-2-yl)- piperidine-2,6-dione
49-A
3-(5-(((1S,2R)-3,3-difluoro- 2-(3-(1-(2-methylcyclopro- pane-1-carbonyl)piperidin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
50-A
1-(4-(1-((1R,6S)-6-((2-(2,6- dioxopiperidin-3-yl)-1- oxoisoindolin-5-yl)oxy)- 2,2-difluorocyclohexyl)azeti- din-3-yl)piperidine-1-carbon- yl)cyclobutane-1-carbonitrile
51-A
3-(5-(((1S,2R)-3,3-difluoro- 2-(3-(1-(3-methyloxetane- 3-carbonyl)piperidin-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
52-A
3-(5-(((1S,2R)-3,3-difluoro- 2-(3-(1-(3-methylbicyclo- [1.1.1]pentane-1-carbonyl)- piperidin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
53-A
1-(4-(1-((1R,6S)-6-((2-(2,6- dioxopiperidin-3-yl)-1-oxo- isoindolin-5-yl)oxy)-2,2- difluorocyclohexyl)azetidin- 3-yl)piperidine-1-carbonyl)- cyclopropane-1-carbonitrile
54-A
3-(5-(((1S.2R)-3,3-difluoro- 2-(3-(1-((1-methylcyclobut- yl)sulfonyl)piperidin-4-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
55-A
3-(5-(((1S,2S)-2-(3-(3- fluorotetrahydro-2H-pyran- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
56-A
3-(5-(((1S,2S)-2-(3-(1-cyclo- butylpiperidin-4-yl)-azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
57-A
3-(5-(((1S,2S)-2-(3-(1- (cyclobutylsulfonyl)piperi- din-4-yl)azetidin-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
58-A
3-(5-(((1S,2S)-2-(3-(2,3- dihydrobenzo[b][1,4]dioxin- 6-yl)azetidin-1-yl)cyclohex- yl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
1-B
3-(1-oxo-5-((2-(3-(2- (trifluoromethyl)-pyridin-4- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
2-B
3-(1-oxo-5-((2-(3-(pyrazin- 2-yl)azetidin-1-yl)cyclohex- yl)oxy)isoindolin-2-yl)- piperidine-2,6-dione
3-B
3-(1-oxo-5-(((1S,2S)-2-(3- (2-(trifluoromethyl)pyridin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)isoindolin-2-yl)piperi- dine-2,6-dione
4-B
3-(1-oxo-5-(((1R,2R)-2-(3- (2-(trifluoromethyl)pyridin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)isoindolin-2-yl)piperi- dine-2,6-dione
5-B
3-(1-oxo-5-(((1R,2S)-2-(3- (2-(trifluoromethyl)pyridin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)isoindolin-2-yl)piperi- dine-2,6-dione
6-B
3-(5-((2-(3-(5-fluoropyrimi- din-2-yl)azetidin-1-yl)cyclo- hexyl)-oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
7-B
3-(5-(((1R,2S)-2-(3-(5- fluoropyrimidin-2-yl)azeti- din-1-yl)cyclohexyl)oxy)-1- oxoisoindolin-2-yl)piperi- dine-2,6-dione
8-B
3-(5-(((1S,2S)-2-(3-(5- fluoropyrimidin-2-yl)azeti- din-1-yl)cyclohexyl)oxy)-1- oxoisoindolin-2-yl)piperi- dine-2,6-dione
9-B
3-(5-(((1R,2R)-2-(3-(5- fluoropyrimidin-2-yl)azeti- din-1-yl)cyclohexyl)oxy)-1- oxoisoindolin-2-yl)piperi- dine-2,6-dione
10-B
3-(5-(((1S,2R)-2-(3-(5-fluoro- pyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
11-B
3-(5-((2-(3-(2-methoxypyri- din-4-yl)azetidin-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
12-B
3-(5-(((1R,2S)-2-(3-(2-meth- oxypyridin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
13-B
3-(5-(((1S,2S)-2-(3-(2-meth- oxypyridin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
14-B
3-(5-(((1R,2R)-2-(3-(2-meth- oxypyridin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
15-B
3-(5-(((1S,2R)-2-(3-(2-meth- oxypyridin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
16-B
3-(5-((2-(3-(6-methoxypyri- din-3-yl)azetidin-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
17-B
3-(5-(((1R,2S)-2-(3-(6-meth- oxypyridin-3-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
18-B
3-(5-(((1S,2S)-2-(3-(6-meth- oxypyridin-3-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
19-B
3-(5-(((1R,2R)-2-(3-(6-meth- oxypyridin-3-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
20-B
3-(5-(((1S,2R)-2-(3-(6-meth- oxypyridin-3-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
21-B
3-(1-oxo-5-((2-(3-(quinox- alin-2-yl)azetidin-1-yl)cyclo- hexyl)oxy)isoindolin-2-yl)- piperidine-2,6-dione
22-B
3-(1-oxo-5-(((1S,2R)-2-(3- (quinoxalin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
23-B
3-(1-oxo-5-(((1R,2R)-2-(3- (quinoxalin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
24-B
3-(1-oxo-5-(((1S,2S)-2-(3- (quinoxalin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
25-B
3-(1-oxo-5-(((1R,2S)-2-(3- (quinoxalin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
26-B
3-(5-((2-(3-(5-chloropyrimi- din-2-yl)azetidin-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
27-B
3-(5-(((1R,2S)-2-(3-(5-chloro- pyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
28-B
3-(5-(((1S,2S)-2-(3-(5-chloro- pyrimidin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
29-B
3-(5-(((1R,2R)-2-(3-(5-chloro- pyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
30-B
3-(5-(((1S,2R)-2-(3-(5-chloro- pyrimidin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
31-B
3-(1-oxo-5-((2-(3-(pyridin-4- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
32-B
3-(1-oxo-5-(((1R,2S)-2-(3- (pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
33-B
3-(1-oxo-5-(((1S,2S)-2-(3- (pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
34-B
3-(1-oxo-5-(((1R,2R)-2-(3- (pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
35-B
3-(1-oxo-5-(((1S,2R)-2-(3- (pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
36-B
3-(1-oxo-5-((2-(3-(pyridin-3- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
37-B
3-(1-oxo-5-(((1R,2S)-2-(3- (pyridin-3-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
38-B
3-(1-oxo-5-(((1S,2S)-2-(3- (pyridin-3-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
39-B
3-(1-oxo-5-(((1R,2R)-2-(3- (pyridin-3-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
40-B
3-(1-oxo-5-(((1S,2R)-2-(3- (pyridin-3-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
41-B
3-(1-oxo-5-(((1S,2R)-2-(3- (2-(trifluoromethyl)pyridin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)isoindolin-2-yl)piperi- dine-2,6-dione
42-B
3-(1-oxo-5-(((1R,2S)-2-(3- (pyrazin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
43-B
3-(1-oxo-5-(((1S,2S)-2-(3- (pyrazin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
44-B
3-(1-oxo-5-(((1R,2R)-2-(3- (pyrazin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
45-B
3-(1-oxo-5-(((1S,2R)-2-(3- (pyrazin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
46-B
3-(1-oxo-5-((2-(3-(pyrimidin- 2-yl)azetidin-1-yl)cyclohex- yl)oxy)-isoindolin-2-yl)- piperidine-2,6-dione
47-B
3-(1-oxo-5-(((1R,2S)-2-(3- (pyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
48-B
3-(1-oxo-5-(((1S,2S)-2-(3- (pyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
49-B
3-(1-oxo-5-(((1R,2R)-2-(3- (pyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
50-B
3-(1-oxo-5-(((1S,2R)-2-(3- (pyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
51-B
3-(1-oxo-5-((2-(3-(pyridin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
52-B
3-(1-oxo-5-(((1R,2S)-2-(3- (pyridin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
53-B
3-(1-oxo-5-(((1S,2S)-2-(3- (pyridin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
54-B
3-(1-oxo-5-(((1R,2R)-2-(3- (pyridin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
55-B
3-(1-oxo-5-(((1S,2R)-2-(3- (pyridin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
56-B
3-(5-((2-(3-(2-methylpyridin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
57-B
3-(5-(((1R,2S)-2-(3-(2-meth- ylpyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
58-B
3-(5-(((1S,2S)-2-(3-(2-meth- ylpyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
59-B
3-(5-(((1R,2R)-2-(3-(2-meth- ylpyridin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
60-B
3-(5-(((1S,2R)-2-(3-(2-meth- ylpyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
61-B
3-(5-((2-(3-(1H-indol-3-yl)- azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
62-B
3-(5-(((1R,2S)-2-(3-(1H- indol-3-yl)azetidin-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
63-B
3-(5-(((1S,2S)-2-(3-(1H- indol-3-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
64-B
3-(5-(((1R,2R)-2-(3-(1H- indol-3-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
65-B
3-(5-(((1S,2R)-2-(3-(1H- indol-3-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
66-B
3-(1-oxo-5-((2-(3-(quinolin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)isoindolin-2-yl)piperi- dine-2,6-dione
67-B
3-(1-oxo-5-(((1S,2R)-2-(3- (quinolin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
68-B
3-(1-oxo-5-(((1R,2R)-2-(3- (quinolin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
69-B
3-(1-oxo-5-(((1R,2S)-2-(3- (quinolin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
70-B
3-(1-oxo-5-(((1S,2S)-2-(3- (quinolin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
71-B
3-(5-((2-(3-(1H-indazol-4- yl)azetidin-1-yl)cyclohexyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
72-B
3-(5-(((1S,2R)-2-(3-(1H- indazol-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
73-B
3-(5-(((1S,2S)-2-(3-(1H- indazol-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
74-B
3-(5-(((1R,2S)-2-(3-(1H- indazol-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
75-B
3-(5-(((1R,2R)-2-(3-(1H- indazol-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
76-B
3-(5-((2-(3-(2-methoxypyr- imidin-5-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
77-B
3-(5-(((1R,2S)-2-(3-(2-meth- oxypyrimidin-5-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
78-B
3-(5-(((1S,2S)-2-(3-(2-meth- oxypyrimidin-5-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
79-B
3-(5-(((1S,2R)-2-(3-(2-meth- oxypyrimidin-5-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
80-B
3-(5-(((1R,2R)-2-(3-(2-meth- oxypyrimidin-5-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
81-B
3-(5-(((1S,2S)-2-(3-(1H-pyr- azol-1-yl)azetidin-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
82-B
3-(5-(((1R,2R)-2-(3-(1H-pyr- azol-1-yl)azetidin-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
83-B
3-(5-(((1S,2R)-2-(3-(1H-pyr- azol-1-yl)azetidin-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
84-B
3-(5-(((1R,2S)-2-(3-(1H-pyr- azol-1-yl)azetidin-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
85-B
3-(1-oxo-5-(((1S,2S)-2-(3- (pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
86-B
3-(1-oxo-5-(((1S,2R)-2-(3- (pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
87-B
3-(1-oxo-5-(((1S,2S)-2-(3- (quinolin-7-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
88-B
3-(1-oxo-5-(((1S,2R)-2-(3- (quinolin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
89-B
3-(1-oxo-5-(((1S,2S)-2-(3- (quinolin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
90-B
3-(1-oxo-5-(((1S,2S)-2-(3- (quinolin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
91-B
3-(1-oxo-5-(((1R,2S)-2-(3- (quinolin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
92-B
3-(5-(((1S,2S)-2-(3-(5-chloro- pyrimidin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
93-B
3-(5-(((1S,2S)-2-(3-(5-chloro- pyrimidin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
94-B
3-(5-(((1R,2S)-2-(3-(5-chloro- pyrimidin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
95-B
3-(5-(((1S,2S)-2-(3-(3-chloro- pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
96-B
3-(5-(((1R,2S)-2-(3-(3-chloro- pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
97-B
3-(5-(((1S,2R)-2-(3-(5-chloro- pyridin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
98-B
3-(5-(((1S,2R)-2-(3-(5-chloro- pyridin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
99-B
3-(5-(((1S,2S)-2-(3-(5-chloro- pyridin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
100-B
3-(5-(((1S,2S)-2-(3-(5-chloro- pyridin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
101-B
3-(5-(((1R,2S)-2-(3-(5-chloro- pyridin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
102-B
3-(5-(((1S,2S)-2-(3-(3-fluoro- pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
103-B
3-(5-(((1S,2S)-2-(3-(3-fluoro- pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
104-B
3-(5-(((1R,2S)-2-(3-(3-fluoro- pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
105-B
3-(5-(((1R,2S)-2-(3-(5-chloro- pyridin-3-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
106-B
3-(5-(((1R,2R)-2-(3-(5-bromo- pyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
107-B
3-(5-(((1S,2S)-2-(3-(5-bromo- pyrimidin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
108-B
3-(5-(((1S,2S)-2-(3-(5-bromo- pyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
109-B
3-(5-(((1R,2R)-2-(3-(5-chloro- pyrimidin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
110-B
3-(5-(((1S,2S)-2-(3-(5-chloro- pyrimidin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
111-B
3-(5-(((1S,2S)-2-(3-(5-chloro- pyrimidin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
112-B
3-(5-(((1S,2S)-2-(3-(3-meth- ylpyridin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
113-B
3-(5-(((1S,2S)-2-(3-(1H-pyr- rolo[2,3-b]pyridin-4-yl)azet- idin-1-yl)cyclohexyl)oxy)-1- oxoisoindolin-2-yl)piperidine- 2,6-dione
114-B
3-(5-(((1S,2R)-2-(3-(5-chloro- pyridin-3-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
115-B
3-(5-(((1S,2R)-2-(3-(5-chloro- pyridin-3-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
116-B
3-(5-(((1S,2S)-2-(3-(5-chloro- pyridin-3-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
117-B
3-(5-(((1S,2S)-2-(3-(5-chloro- pyridin-3-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
118-B
3-(1-oxo-5-(((1R,2S)-2-(3-(5- (trifluoromethyl)pyrimidin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
119-B
3-(1-oxo-5-(((1R.2S)-2-(3-(5- (trifluoromethyl)pyrimidin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
120-B
3-(1-oxo-5-(((1S,2S)-2-(3-(5- (trifluoromethyl)pyrimidin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperidine- 2,6-dione
121-B
3-(1-oxo-5-(((1S,2R)-2-(3-(5- (trifluoromethyl)pyrimidin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
122-B
3-(1-oxo-5-(((1S,2R)-2-(3-(5- (trifluoromethyl)pyrimidin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
123-B
3-(1-oxo-5-(((1S,2S)-2-(3-(5- (trifluoromethyl)pyrimidin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
124-B
3-(1-oxo-5-(((1R,2R)-2-(3- (6-(trifluoromethyl)pyridin-3- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
125-B
3-(1-oxo-5-(((1R,2R)-2-(3-(6- (trifluoromethyl)pyridin-3- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
126-B
3-(1-oxo-5-(((1S,2S)-2-(3-(6- (trifluoromethyl)pyridin-3- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
127-B
3-(1-oxo-5-(((1S,2S)-2-(3-(6- (trifluoromethyl)pyridin-3- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
128-B
3-(1-oxo-5-(((1R,2R)-2-(3-(5- (trifluoromethyl)pyridin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
129-B
3-(1-oxo-5-(((1R.2R)-2-(3-(5- (trifluoromethyl)pyridin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
130-B
3-(1-oxo-5-(((1S,2S)-2-(3-(5- (trifluoromethyl)pyridin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
131-B
3-(1-oxo-5-(((1S,2S)-2-(3-(5- (trifluoromethyl)pyridin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
132-B
3-(5-(((1R,2R)-2-(3-(5-cyclo- propylpyrimidin-2-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine-2,6- dione
133-B
3-(5-(((1R,2R)-2-(3-(5-cyclo- propylpyrimidin-2-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine-2,6- dione
134-B
3-(5-(((1S,2S)-2-(3-(5-cyclo- propylpyrimidin-2-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine-2,6- dione
135-B
3-(5-(((1S,2S)-2-(3-(5-cyclo- propylpyrimidin-2-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine-2,6- dione
136-B
3-(1-oxo-5-(((1S,2R)-2-(3- (pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
137-B
Rac-3-(5-(((trans)-2-(3-(5- bromopyrimidin-2-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine-2,6- dione
138-B
Rac-3-(5-(((cis)-2-(3-(5- bromopyrimidin-2-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine-2,6- dione
139-B
Rac-3-(5-(((cis)-2-(3-(5- chloropyrimidin-4-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine-2,6- dione
140-B
Rac-3-(5-(((trans)-2-(3-(5- chloropyrimidin-4-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine-2,6- dione
141-B
3-(1-oxo-5-((2-(3-(6-(trifluoro- methyl)pyridin-3-yl)azetidin- 1-yl)cyclopentyl)oxy)iso- indolin-2-yl)piperidine-2,6- dione
142-B
3-(1-oxo-5-((2-(3-(pyridazin- 3-yl)azetidin-1-yl)cyclohex- yl)oxy)isoindolin-2-yl)piperi- dine-2,6-dione
143-B
3-(1-oxo-5-((2-(3-(pyridazin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)isoindolin-2-yl)piperi- dine-2,6-dione
144-B
Rac-1-(5-(((cis)-2-(3-(5-meth- yloxazol-2-yl)azetidin-1-yl)- cyclopentyl)oxy)-1-oxoiso- indolin-2-yl)-3-azabicyclo [3.1.1]heptane-2,4-dione
145-B
Rac-1-(5-(((trans)-2-(3-(5- methyloxazol-2-yl)azetidin-1- yl)cyclopentyl)oxy)-1-oxoiso- indolin-2-yl)-3-azabicyclo [3.1.1]heptane-2,4-dione
146-B
Rac-3-(1-oxo-5-(((cis)-2-(3- (quinolin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
147-B
3-(1-oxo-5-((2-(3-(5-(trifluoro- methyl)pyridin-2-yl)azetidin- 1-yl)cyclopentyl)oxy)iso- indolin-2-yl)piperidine-2,6- dione
148-B
1-(1-oxo-5-((2-(3-(pyridin-4- yl)azetidin-1-yl)cyclopentyl)- oxy)isoindolin-2-yl)-3-aza- bicyclo[3.1.1]heptane-2,4- dione
149-B
Rac-1-(5-(((cis)-2-(3-(5-meth- yloxazol-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)-3-azabicyclo [3.1.1]heptane-2,4-dione
150-B
Rac-1-(5-(((trans)-2-(3-(5- methyloxazol-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)-3-azabicyclo [3.1.1]heptane-2,4-dione
151-B
Rac-3-(5-(((trans)-2-(3-(5- methyloxazol-2-yl)azetidin-1- yl)cyclopentyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
152-B
Rac-3-(1-oxo-5-(((trans)-2-(3- (quinolin-2-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
153-B
Rac-3-(5-(((cis)-2-(3-(3-fluoro- pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
154-B
3-(1-oxo-5-((2-(3-(5-(trifluoro- methyl)pyridin-3-yl)azetidin- 1-yl)cyclopentyl)oxy)iso- indolin-2-yl)piperidine-2,6- dione
155-B
Rac-3-(5-(((cis)-2-(3-(5- chloropyridin-3-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
156-B
Rac-1-(5-(((cis)-2-(3-(5- chloropyrimidin-2-yl)azetidin- 1-yl)cyclopentyl)oxy)-1-oxo- isoindolin-2-yl)-3-azabicyclo [3.1.1]heptane-2,4-dione
157-B
Rac-1-(5-(((trans)-2-(3-(5- chloropyrimidin-2-yl)azetidin- 1-yl)cyclopentyl)oxy)-1-oxo- isoindolin-2-yl)-3-azabicyclo [3.1.1]heptane-2,4-dione
158-B
3-(5-((2-(3-(5-fluoropyrimi- din-2-yl)azetidin-1-yl)cyclo- pentyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
159-B
Rac-1-(1-oxo-5-(((cis)-2-(3- (pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)isoindolin- 2-yl)-3-azabicyclo[3.1.1] heptane-2,4-dione
160-B
Rac-1-(1-oxo-5-(((trans)-2- (3-(pyridin-4-yl)azetidin-1- yl)cyclohexyl)oxy)isoindolin- 2-yl)-3-azabicyclo[3.1.1] heptane-2,4-dione
161-B
Rac-3-(5-(((cis)-2-(3-(5- methyloxazol-2-yl)azetidin-1- yl)cyclopentyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
162-B
Rac-3-(5-(((cis)-2-(3-(3- chloropyridin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
163-B
Rac-3-(5-(((trans)-2-(3-(5- chloropyridin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
164-B
Rac-3-(5-(((cis)-2-(3-(5- chloropyridin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
165-B
Rac-3-(5-(((cis)-2-(3-(4- chloropyridin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
166-B
Rac-3-(5-(((trans)-2-(3-(4- chloropyridin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
167-B
Rac-3-(5-(((trans)-2-(3-(3- fluoropyridin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
168-B
Rac-3-(5-(((trans)-2-(3-(5- chloropyridin-3-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
169-B
3-(1-oxo-5-((2-(3-(quinolin- 7-yl)azetidin-1-yl)cyclopent- yl)oxy)isoindolin-2-yl)piper- idine-2,6-dione
170-B
3-(5-((2-(3-(2-methoxypyridin- 4-yl)azetidin-1-yl)cyclopent- yl)oxy)-1-oxoisoindolin-2- yl)piperidine-2,6-dione
171-B
Rac-1-(5-(((cis)-2-(3-(5-chloro- pyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)-3-azabicyclo [3.1.1]heptane-2,4-dione
172-B
Rac-1-(5-(((trans)-2-(3-(5- chloropyrimidin-2-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)-3-azabicyclo [3.1.1]heptane-2,4-dione
173-B
Rac-3-(5-(((trans)-2-(3-(3- chloropyridin-4-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
174-B
Rac-3-(5-(((cis)-2-(3-(5-meth- yloxazol-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
175-B
Rac-3-(5-(((trans)-2-(3-(5- methyloxazol-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
176-B
3-(5-(((1S,2S)-2-(3-(1H- imidazol-1-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
177-B
3-(5-((2-(3-(5-cyclopropyl- pyrimidin-2-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
178-B
3-(1-oxo-5-((2-(3-(5-(trifluoro- methyl)pyridin-3-yl)azetidin- 1-yl)cyclohexyl)oxy)isoin- dolin-2-yl)piperidine-2,6- dione
179-B
Rac-4-(1-((cis)-2-((2-(2,6- dioxopiperidin-3-yl)-1-oxo- isoindolin-5-yl)oxy)cyclohex- yl)azetidin-3-yl)picolinonitrile
180-B
Rac-4-(1-((trans)-2-((2-(2,6- dioxopiperidin-3-yl)-1-oxo- isoindolin-5-yl)oxy)cyclo- hexyl)azetidin-3-yl)picolino- nitrile
181-B
3-(5-((2-(3-(1H-indol-3-yl)- azetidin-1-yl)cyclopentyl)- oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
182-B
Rac-3-(1-oxo-5-(((cis)-2-(3- (5-(trifluoromethyl)pyridin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
183-B
Rac-3-(1-oxo-5-(((cis)-2-(3- (6-(trifluoromethyl)pyridin- 3-yl)azetidin-1-yl)cyclohex- yl)oxy)isoindolin-2-yl)piperi- dine-2,6-dione
184-B
Rac-3-(5-(((cis)-2-(3-(5-meth- ylpyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
185-B
Rac-3-(5-(((cis)-2-(3-(4-meth- ylpyrimidin-2-yl)azetidin-1- yl)cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
186-B
Rac-3-(1-oxo-5-(((cis)-2-(3- (5-(trifluoromethyl)pyrimi- din-2-yl)azetidin-1-yl)cyclo- hexyl)oxy)isoindolin-2-yl)- piperidine-2,6-dione
187-B
Rac-3-(1-oxo-5-(((trans)-2-(3- (5-(trifluoromethyl)pyrimidin- 2-yl)azetidin-1-yl)cyclohex- yl)oxy)isoindolin-2-yl)piperi- dine-2,6-dione
188-B
Rac-3-(5-(((trans)-2-(3-(4- methylpyrimidin-2-yl)azeti- din-1-yl)cyclohexyl)oxy)-1- oxoisoindolin-2-yl)piperidine- 2,6-dione
189-B
Rac-3-(5-(((trans)-2-(3-(5- methylpyrimidin-2-yl)azetidin- 1-yl)cyclohexyl)oxy)-1-oxo- isoindolin-2-yl)piperidine-2,6- dione
190-B
3-(5-((2-(3-(2-methylpyrimi- din-4-yl)azetidin-1-yl)cyclo- hexyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
191-B
Rac-3-(1-oxo-5-(((trans)-2-(3- (6-(trifluoromethyl)pyridin-3- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
192-B
Rac-3-(1-oxo-5-(((trans)-2-(3- (5-(trifluoromethyl)pyridin-2- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
193-B
3-(1-oxo-5-((2-(3-(quinolin-7- yl)azetidin-1-yl)cyclohexyl)- oxy)isoindolin-2-yl)piperi- dine-2,6-dione
194-B
3-(1-oxo-5-(((1R,2S)-2-(3- (quinolin-4-yl)azetidin-1-yl)- cyclopentyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
195-B
Rac-3-(1-oxo-5-(((trans)-2- (3-(quinolin-4-yl)azetidin-1- yl)cyclopentyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
196-B
Rac-3-(1-oxo-5-(((cis)-2-(3- (pyrimidin-5-yl)azetidin-1- yl)cyclopentyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
197-B
Rac-3-(1-oxo-5-(((trans)-2-(3- (pyrimidin-5-yl)azetidin-1- yl)cyclopentyl)oxy)isoindolin- 2-yl)piperidine-2,6-dione
198-B
3-(5-((2-(3-(3-methylpyridin- 4-yl)azetidin-1-yl)cyclohex- yl)oxy)-1-oxoisoindolin-2-yl)- piperidine-2,6-dione
199-B
3-(5-((2-(3-(1H-pyrrolo[2,3- b]pyridin-4-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
200-B
3-(5-((2-(3-(5-chloropyrimi- din-2-yl)azetidin-1-yl)cyclo- pentyl)oxy)-1-oxoisoindolin- 2-yl)piperidine-2,6-dione
201-B
Rac-3-(5-(((cis)-2-(3-(6-meth- oxypyridin-3-yl)azetidin-1- yl)cyclopentyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
202-B
Rac-3-(5-(((trans)-2-(3-(6- methoxypyridin-3-yl)azetidin- 1-yl)cyclopentyl)oxy)-1-oxo- isoindolin-2-yl)piperidine- 2,6-dione
203-B
3-(1-oxo-5-((2-(3-(quinoxalin- 2-yl)azetidin-1-yl)cyclopent- yl)oxy)isoindolin-2-yl)piperi- dine-2,6-dione
204-B
3-(5-(((1S,2S)-2-(3-(1H- indazol-5-yl)azetidin-1-yl)- cyclohexyl)oxy)-1-oxoiso- indolin-2-yl)piperidine-2,6- dione
205-B
Rac-3-(1-oxo-5-(((cis)-2-(3- (pyridin-4-yl)azetidin-1-yl)- cyclopentyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
206-B
Rac-3-(1-oxo-5-(((trans)-2-(3- (pyridin-4-yl)azetidin-1-yl)- cyclopentyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
207-B
Rac-3-(1-oxo-5-(((cis)-2-(3- (pyridin-3-yl)azetidin-1-yl)- cyclopentyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
208-B
Rac-3-(1-oxo-5-(((trans)-2-(3- (pyridin-3-yl)azetidin-1-yl)- cyclopentyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
209-B
Rac-3-(1-oxo-5-(((cis)-2-(3- (pyridin-2-yl)azetidin-1-yl)- cyclopentyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
210-B
Rac-3-(1-oxo-5-(((trans)-2-(3- (pyridin-2-yl)azetidin-1-yl)- cyclopentyl)oxy)isoindolin-2- yl)piperidine-2,6-dione
211-B
3-(5-((2-(3-(2H-indazol-4-yl)- azetidin-1-yl)cyclohexyl)oxy)- 1-oxoisoindolin-2-yl)piperi- dine-2,6-dione
212-B
3-(1-oxo-5-((2-(3-(pyrimidin- 5-yl)azetidin-1-yl)cyclohex- yl)-oxy)isoindolin-2-yl)piperi- dine-2,6-dione
or wherein the compound is selected from:
Structure
or wherein the compound is selected from:
#
Structure
1-A
12-A
14-A
22-A
Second Eluting Isomer
24-A
25-A
26-A
27-A
28-A
29-A
30-A
31-A
32-A
33-A
34-A
35-A
41-A
42-A
55-A
56-A
57-A
58-A
1-B
2-B
6-B
11-B
16-B
21-B
26-B
31-B
36-B
46-B
56-B
61-B
66-B
71-B
76-B
81-B
87-B
89-B
Diastereomer 1
90-B
Diastereomer 2
91-B
Diastereomer 3
92-B
Diastereomer 1
93-B
Diastereomer 2
95-B
Diastereomer 1
98-B
Diastereomer 2
99-B
Diastereomer 3
100-B
Diastereomer 4
102-B
Diastereomer 1
103-B
Diastereomer 2
108-B
Diastereomer 3
111-B
Diastereomer 3
112-B
Diastereomer 1
116-B
Diastereomer 4
117-B
Diastereomer 5
120-B
Diastereomer 3
123-B
Diastereomer 6
125-B
Diastereomer 2
126-B
Diastereomer 3
127-B
Diastereomer 4
129-B
Diastereomer 2
130-B
Diastereomer 3
131-B
Diastereomer 4
134-B
Diastereomer 3
135-B
Diastereomer 4
136-B
Diastereomer 3
137-B
139-B
142-B
146-B
152-B
153-B
155-B
161-B
162-B
163-B
165-B
169-B
170-B
173-B
174-B
177-B
179-B
182-B
183-B
184-B
185-B
186-B
188-B
190-B
193-B
194-B
198-B
199-B
201-B
204-B
205-B
209-B
211-B

671 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/577,672Filed 8 Jul 2022
Priority: 9 Jul 2021
Published: 27 Mar 2025
Term ends: Not estimatedThe source records don’t support an estimate.

Classification20 codes

A61P 35/00
Antineoplastic agents
C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
A61K 31/454
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
A61K 31/4545
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine

Family

Application63/220,319Us provisional application · filed 9 Jul 2021
Application63/220,321Us provisional application · filed 9 Jul 2021
Application63/314,994Us provisional application · filed 28 Feb 2022
Application63/317,930Us provisional application · filed 8 Mar 2022
US 2025/0100996 A1This patent

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

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Abstract

A compound of formula I-A:

or a pharmaceutically acceptable salt, solvate, stereoisomer, or tautomer thereof, wherein:
m is zero, one, two, or three;
n is zero, one, or two;
q is one, two, or three;
s is one;
L1 is CH2 or a covalent bond;
Q is selected from —C(O)NR5R6 or a 4- to 10-member heterocyclic group having one or more heteroatoms independently selected from NR20, O, S, and SO2, where R20 is —[C(O)]wR7, S(O)2R7, or a covalent bond linking said heterocyclic group to ring A, wherein said heterocyclic group is independently unsubstituted or substituted with C(O)R7, or with one to five R8, and where w is 0 or 1;
T is CH2, CH(R2), C(R2)2, or N, provided that when T is N, L1 is attached to T;
X is hydrogen, deuterium, or fluoro;
Y is a covalent bond, —O—, or —NR—;
Z and Z1 are each independently CR1 or N;
ring A is phenyl or a 4- to 7-membered nitrogen containing heterocyclyl, wherein ring A is independently unsubstituted or substituted with one to five R8;
R is hydrogen or C1-C4 alkyl;
each R1 is independently hydrogen, halo, cyano, hydroxy, —N(R9)2, C1-C4 alkyl independently unsubstituted or substituted with from one to three R10, or C1-C6 alkoxy independently unsubstituted or substituted with from one to three R10;
or
when Z1 is CR1, then two adjacent R1 together with the carbon atoms to which they are attached form a C3-C7 cycloalkyl, a C6-C10 aryl, a 4- to 7-membered heterocycloalkenyl, or a 5- to 6-membered heteroaryl, wherein each of said cycloalkyl, heterocycloalkenyl, aryl, and heteroaryl are independently substituted with one to three R11;
each R2 is independently selected from halo, cyano, hydroxy, —N(R9)2, C1-C4 alkyl independently unsubstituted or substituted with from one to three R10, and C1-C4 alkoxy independently unsubstituted or substituted with from one to three R10;
R3 is selected from the group consisting of hydrogen, amino, halo, cyano, hydroxy, C1-C6 alkyl, and C1-C6 haloalkyl;
R4 is hydrogen or —CH2—OR12;
R5 and R6, together with the nitrogen to which they are attached, form a 4- to 7-membered heterocyclyl, wherein said heterocyclyl is independently unsubstituted or substituted with one to five R8;
R7 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C3-C7 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, 4- to 7-membered heterocyclyl, C6-C10 aryl, 5- to 10-membered heteroaryl, or —N(R8)2;
wherein said alkyl, alkoxy, cycloalkyl, alkenyl, alkynyl, heterocyclyl, aryl, or heteroaryl is further independently unsubstituted or substituted with one to five R8;
each R8 is independently halo, cyano, hydroxy, —SH, —NH2, —NO2, —SF5, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C10 cycloalkyl, heterocyclyl, aryl, or heteroaryl;
each R9 is independently H or C1-C4 alkyl independently unsubstituted or substituted with from 1 to 3 substituents selected from halo, cyano, hydroxy, and C1-C4 alkoxy, or two R9 together with the nitrogen atom to which they are attached form a 3- to 7-membered heterocycloalkyl or 5- to 6-membered heteroaryl;
each R10 is independently —N(R9)2, halo, cyano, hydroxy, or C1-C4 alkoxy;
each R11 is independently —N(R9)2, halo, cyano, hydroxy, or oxo;
R12 is —C(O)—R13 or —P(O)(OR14)2;
R13 is C1-C4 alkyl or C1-C4 alkoxy;
and
each R14 is independently H or C1-C4 alkyl.

27 more elements

Facts

Application

18/577,672Filed 8 Jul 2022

Priority

9 Jul 2021

Published

27 Mar 2025

Term ends

Not estimatedThe source records don’t support an estimate.

Classification20 codes

A61P 35/00
Antineoplastic agents
C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
A61K 31/454
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
A61K 31/4545
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine

Family

Application63/220,319Us provisional application · filed 9 Jul 2021

Application63/220,321Us provisional application · filed 9 Jul 2021

Application63/314,994Us provisional application · filed 28 Feb 2022

Application63/317,930Us provisional application · filed 8 Mar 2022

US 2025/0100996 A1This patent

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