US 2019/0365718 A1Published application

Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase

AssigneeBoard of Regents, The University of Texas System

InventorsRichard T. LEWIS, Matthew HAMILTON, Philip JONES, Alessia PETROCCHI, Naphtali REYNA, Jason CROSS, Michele HAN, Michael SOTH, Timothy MCAFOOS, Martin TREMBLAY

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Abstract

Compounds of formula (VII), which are useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase, are provided. Also provided are pharmaceutical compositions, kits comprising said compounds, and methods and uses pertaining to said compounds.

Claims61

Dependent claims

A compound characterised by formula (VII),

or a pharmaceutically acceptable salt or prodrug thereof, wherein one but not both of the dashed bonds may optionally be a carbon-carbon double bond, and wherein:
W is selected from C, CH, and N;
a is 0 or 1;
b is 0, 1 or 2;
c is 0 or 1;
d is 0 or 1;
e is 0 or 1;
f is 0, 1 or 2;
A is selected from O, C(O), and S(O)2;
J is in each case independently selected from oxo, OH, CN, halogen, and C1-3-alkyl;
X1 is selected from C(R8)(R9), N(R10), O, and S;
X2 is selected from C(R11)(R12), N(R13), and O;
Y is selected from
C6-10-aryl, and
5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
wherein said aryl and heteroaryl are optionally substituted by one or more groups independently selected from R14;
R1 is selected from
H,
(G)n-(C1-6-alkyl),
(G)n-(C3-8-cycloalkyl),
N3,
(G)n-heterocycloalkyl, wherein said heterocycloalkyl is a 3- to 6-membered heterocycloalkyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
(G)n-(C5-8-cycloalkenyl),
(G)n-heterocycloalkenyl, wherein said heterocycloalkenyl is a 5- to 6-membered heterocycloalkenyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
(G)n-(C6-10-aryl), and
(G)n-heteroaryl, wherein said heteroaryl is a 5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
wherein G in each case is independently selected from C(R8)(R9), C(O), S(O)2, C(O)NR10, and S(O)2NR10;
and wherein n in each case is either 0 or 1, and
wherein said alkyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl are optionally substituted by one or more groups independently selected from R15;
R2, R3, R4, R6, R7, R8, R9, R11 and R12 are in each case independently selected from
H,
halogen,
CN,
OH,
(C0-4-alkyl)-SO2R17,
(C0-4-alkyl)-N(R18)2,
(C0-4-alkyl)-NHCOR19,
(C0-4-alkyl)-NHSO2R20,
(C0-4-alkyl)-CON(R21)2,
(C0-4-alkyl)-CO2R22,
(C0-4-alkyl)-SO2N(R23)2,
C1-6-alkyl,
O—(C1-6-alkyl),
C3-8-cycloalkyl,
3- to 6-membered heterocycloalkyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C5-8-cycloalkenyl,
5- to 6-membered heterocycloalkenyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C6-10-aryl, and
5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O, or
one or both geminal R3 and R4 pairs, taken together with the carbon atom to which they are attached, independently forms a 3- to 6-membered cycloalkyl group or a 3- to 6-membered heterocycloalkyl group which comprises 1, 2 or 3 ring heteroatoms selected from N, S and O,
wherein said alkyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl are optionally substituted by one or more groups independently selected from R16;
R5, R10 and R13 are in each case independently selected from
H,
C1-6-alkyl,
C3-8-cycloalkyl,
3- to 6-membered heterocycloalkyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C5-8-cycloalkenyl,
5- to 6-membered heterocycloalkenyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C6-10-aryl, and
5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
optionally wherein one of R3 and R5, together with one of R11 and R13 and the atoms intervening between them, may form a 5- or 6-membered cycloalkyl, cycloalkenyl or aryl group, or a 5- or 6-membered heterocycloalkyl, heterocycloalkenyl or heteroaryl group which comprises 1, 2, 3 or 4 ring heteroatoms selected from N, S and O;
wherein said alkyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl are optionally substituted by one or more groups independently selected from R24;
any two R14 substituents on adjacent ring atoms may, together with the ring atoms to which they are attached, independently form a 5- or 6-membered cyclic group optionally comprising 1, 2 or 3 ring heteroatoms selected from N, S and O, which cyclic group is optionally substituted by one or more groups independently selected from halogen, C1-4-alkyl and C1-4-haloalkyl, and
any remaining R14 is in each case independently selected from
halogen,
CN,
OH,
C1-6-alkyl,
O—(C1-6-alkyl),
O—(C1-6-haloalkyl),
O—(C1-6-alkyl-C3-6-cycloalkyl),
(C0-4-alkyl)-SO2R17,
(C0-4-alkyl)-N(R18)2,
(C0-4-alkyl)-NHCOR19,
(C0-4-alkyl)-NHSO2R20,
(C0-4-alkyl)-CON(R21)2,
(C0-4-alkyl)-CO2R22,
(C0-4-alkyl)-SO2N(R23)2, and
(C0-4-alkyl)-heteroaryl,
wherein said heteroaryl is a 5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O;
R15 is in each case independently selected from
halogen,
CN,
OH,
oxo,
NO2,
C1-6-alkyl,
C2-6-alkenyl,
C2-6-alkynyl,
(C0-4-alkyl)-O—(C1-6-alkyl),
(C0-4-alkyl)-SO2R17,
(C0-4-alkyl)-N(R18)2,
(C0-4-alkyl)-NHCOR19,
(C0-4-alkyl)-NHSO2R20,
(C0-4-alkyl)-CON(R21)2,
(C0-4-alkyl)-CO2R22,
(C0-4-alkyl)-SO2N(R23)2,
(C0-4-alkyl)-heteroaryl, wherein said heteroaryl is a 5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
(C0-4-alkyl)-heterocycloalkenyl, wherein said heterocycloalkenyl is a 5- to 10-membered heterocycloalkenyl comprising 1 or 2 ring heteroatoms selected from N and O,
(C0-4-alkyl)-heterocycloalkyl, wherein said heterocycloalkyl is a 4- to 6-membered heterocycloalkyl comprising 1 or 2 ring heteroatoms selected from N and O,
(C0-4-alkyl)-aryl, wherein said aryl is a 6- to 10-membered aryl,
(C0-4-alkyl)-cycloalkenyl, wherein said cycloalkenyl is a 5- to 8-membered cycloalkenyl, and
(C0-4-alkyl)-cycloalkyl, wherein said cycloalkyl is a 3- to 8-membered cycloalkyl,
wherein said alkyl, alkenyl, alkynyl, heteroaryl, heterocycloalkenyl, heterocycloalkyl, aryl, cycloalkenyl and cycloalkyl are optionally substituted by one or more groups independently selected from halogen, OH, O—(C1-4-alkyl), oxo, C(O)—(C1-4-alkyl), C(O)O—(C1-4-alkyl), and NH2;
R16 and R24 are in each case independently selected from
halogen,
CN,
OH,
C1-6-alkyl,
O—(C1-6-alkyl),
(C0-4-alkyl)-SO2R17,
(C0-4-alkyl)-N(R18)2,
(C0-4-alkyl)-NHCOR19,
(C0-4-alkyl)-NHSO2R20,
(C0-4-alkyl)-CON(R21)2,
(C0-4-alkyl)-CO2R22,
(C0-4-alkyl)-SO2N(R23)2,
(C0-4-alkyl)-heteroaryl, wherein said heteroaryl is a 5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
(C0-4-alkyl)-heterocycloalkenyl, wherein said heterocycloalkenyl is a 5- to 6-membered heterocycloalkenyl comprising 1 or 2 ring heteroatoms selected from N and O,
(C0-4-alkyl)-heterocycloalkyl, wherein said heterocycloalkyl is a 4- to 6-membered heterocycloalkyl comprising 1 or 2 ring heteroatoms selected from N and O,
(C0-4-alkyl)-aryl, wherein said aryl is a 6- to 10-membered aryl,
(C0-4-alkyl)-cycloalkenyl, wherein said cycloalkenyl is a 5- to 8-membered cycloalkenyl, and
(C0-4-alkyl)-cycloalkyl, wherein said cycloalkyl is a 3- to 8-membered cycloalkyl,
wherein said alkyl, heteroaryl, heterocycloalkenyl, heterocycloalkyl, aryl, cycloalkenyl and cycloalkyl are optionally substituted by one or more groups independently selected from halogen;
and
R17 to R23 are in each case independently selected from
H,
C1-6-alkyl,
C3-8-cycloalkyl,
3- to 6-membered heterocycloalkyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C5-8-cycloalkenyl,
5- to 6-membered heterocycloalkenyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C6-10-aryl, and
5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
wherein any pair of R18 groups attached to the same nitrogen atom, taken together with the intervening nitrogen atom, may form a 3- to 10-membered heterocycloalkyl or heterocycloalkenyl group comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
wherein any pair of R21 groups attached to the same nitrogen atom, taken together with the intervening nitrogen atom, may form a 3- to 10-membered heterocycloalkyl or heterocycloalkenyl group comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
wherein any pair of R23 groups attached to the same nitrogen atom, taken together with the intervening nitrogen atom, may form a 3- to 10-membered heterocycloalkyl or heterocycloalkenyl group comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
wherein each said alkyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl is optionally and independently substituted by one or more groups independently selected from halogen, OH, C1-6-alkyl and C1-6-haloalkyl.

135 more elements

A compound selected from the group consisting of Compounds 1 to 363:

Compound 1
4-chloro-N-(1-((1R,3r,5S,6r)-3-
hydroxybicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 2
4-chloro-N-(1-((1R,3r,5S,6r)-3-(quinolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 3
4-chloro-N-(1-((1R,3s,5S,6r)-3-
hydroxybicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 4
4-chloro-N-(1-((1R,3s,5S,6r)-3-(quinolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 5
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 6
4-chloro-N-(1-((1R,3s,5S,6r)-3-(6-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 7
2-(4-chlorophenyl)-N-((1R,3s,5S,6r)-3-((6-
fluoroquinolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)acetamide
Compound 8
(1R,5S)-N-(4-chlorophenyl)-3-(quinolin-4-
yloxy)bicyclo[3.1.0]hexane-6-carboxamide
Compound 9
4-chloro-N-(((1R,3s,5S,6r)-3-((6-fluoroquinolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)methyl)benzamide
Compound 10
1-(4-chlorophenyl)-3-((1R,3s,5S,6r)-3-((6-
fluoroquinolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-yl)urea
Compound 11
2-(4-chlorophenyl)-5-(3-(quinolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)-1,3,4-oxadiazole
Compound 12
4-((6-(2-(4-chlorophenoxy)ethyl)bicyclo[3.1.0]hexan-3-
yl)oxy)-6-fluoro-2-(trifluoromethyl)quinoline
Compound 13
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 14
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-
fluorophenoxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 15
4-chloro-N-(1-((1R,3s,5S,6r)-3-((2-methylpyridin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 16
(1R,5S)-N-(4-chlorobenzyl)-3-(quinolin-4-
yloxy)bicyclo[3.1.0]hexane-6-carboxamide
Compound 17
(1R,5S)-N-(4-chlorobenzyl)-3-((6-fluoro-2-
(trifluoromethyl)quinolin-4-
yl)oxy)bicyclo[3.1.0]hexane-6-carboxamide
Compound 18
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-fluoropyridin-3-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 19
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 20
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-fluoro-2-
methylquinolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 21
4-chloro-N-(1-((1R,3s,5S,6r)-3-((7-chloroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 22
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-fluoro-2-
(trifluoromethyl)quinolin-4-yl)oxy)bicyclo[3.1.0]hexan-
6-yl)propyl)benzamide
Compound 23
4-chloro-N-(((1R,3s,5S,6s)-3-((6-fluoroquinolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)methyl)benzamide
Compound 24
4-chloro-N-(((1R,3s,5S,6s)-3-((6-fluoro-2-
(trifluoromethyl)quinolin-4-yl)oxy)bicyclo[3.1.0]hexan-
6-yl)methyl)benzamide
Compound 25
4-chloro-N-(3-((6-fluoro-2-(trifluoromethyl)quinolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)benzamide
Compound 26
4-chloro-N-(3-(quinolin-4-yloxy)bicyclo[3.1.0]hexan-6-
yl)benzamide
Compound 27
1-(4-bromophenyl)-N-(3-(quinolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)methanesulfonamide
Compound 28
4-chloro-N-(3-(quinolin-4-yloxy)bicyclo[3.1.0]hexan-6-
yl)benzenesulfonamide
Compound 29
1-(4-chlorophenyl)-3-((1R,3r,5S,6r)-3-((6-
fluoroquinolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-yl)urea
Compound 30
2-(4-chlorophenyl)-N-((1R,5S)-3-(quinolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)acetamide
Compound 31
2-(4-chlorophenyl)-N-((1R,3r,5S)-3-((6-fluoroquinolin-
4-yl)oxy)bicyclo[3.1.0]hexan-6-yl)acetamide
Compound 32
4-chloro-N-(((1R,3r,5S,6r)-3-((6-fluoroquinolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)methyl)benzamide
Compound 33
4-chloro-N-(((1R,3r,5S,6r)-3-((4-chloroquinolin-6-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)methyl)benzamide
Compound 34
4-chloro-N-(1-((1R,3s,5S,6r)-3-(7-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 35
4-chloro-N-(1-((1R,3s,5S,6r)-3-((7-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 36
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 37
4-chloro-N-(1-((1R,3s,5S,6r)-3-((5-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 38
N-(1-((1R,3s,5S,6r)-3-((1,5-naphthyridin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)-4-
chlorobenzamide
Compound 39
4-chloro-N-(1-((1R,3s,5S,6r)-3-((3-fluoropyridin-2-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 40
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-methylpyridin-2-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 41
4-chloro-N-(1-((1R,3s,5S,6r)-3-((3-methylpyridin-2-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 42
4-chloro-N-(1-((1R,3s,5S,6r)-3-(2,5-
difluorophenoxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 43
4-chloro-N-(1-((1R,3s,5S,6r)-3-(quinolin-8-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 44
4-chloro-N-(1-((1R,3s,5S,6r)-3-(2,6-
difluorophenoxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 45
N-(1-((1R,3s,5S,6r)-3-(2-(2-amino-2-
oxoethyl)phenoxy)bicyclo[3.1.0]hexan-6-yl)propyl)-4-
chlorobenzamide
Compound 46
4-chloro-N-(1-((1R,3s,5S,6r)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 47
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-oxocinnolin-1(4H)-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 48
4-chloro-N-(1-((1R,3s,5S,6r)-3-(2-
((dimethylamino)methyl)phenoxy)bicyclo[3.1.0]hexan-
6-yl)propyl)benzamide
Compound 49
4-chloro-N-(1-((1R,3s,5S,6r)-3-(quinolin-3-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 50
4-chloro-N-(1-((1R,3s,5S,6r)-3-((1-methyl-2-oxo-1,2-
dihydroquinolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 51
N-(1-((1R,3s,5S,6r)-3-(1H-pyrazolo[4,3-c]pyridin-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 52
4-chloro-N-(1-((1R,3s,5S,6r)-3-((5-fluoro-2-
methylpyrimidin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 53
4-chloro-N-(1-((1R,3s,5S,6r)-3-(7-chloro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 54
4-chloro-N-(1-((1R,3s,5S,6r)-3-((5-fluoropyrimidin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 55
N-(1-((1R,3s,5S,6r)-3-((1,6-naphthyridin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)-4-
chlorobenzamide
Compound 56
4-chloro-N-(1-((1R,3s,5S,6r)-3-((7-fluoroquinolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 57
4-chloro-N-(1-((1R,3s,5S,6r)-3-((4-chloroquinolin-7-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 58
4-chloro-N-(1-((1R,3s,5S,6r)-3-((5-fluoropyridin-3-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 59
4-chloro-N-(1-((1R,3s,5S,6r)-3-(quinazolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 60
4-chloro-N-(1-((1R,3s,5S,6r)-3-((2-chloropyridin-3-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 61
2-(4-chlorophenyl)-N-((1R,3s,5S,6r)-3-((6-
fluoroquinazolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)acetamide
Compound 62
2-(4-chlorophenyl)-N-((1R,3s,5S,6r)-3-(6-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)acetamide
Compound 63
4-chloro-N-(1-((1R,3s,5S,6r)-3-(6-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 64
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 65
4-chloro-N-(((1R,3s,5S,6r)-3-(6-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)methyl)benzamide
Compound 66
4-cyano-N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 67
4-cyano-N-(1-((1R,3s,5S,6r)-3-(6-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 68
N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)-2-
methoxypyrimidine-5-carboxamide
Compound 69
2,2-difluoro-N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-
4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzo[d][1,3]dioxole-5-carboxamide
Compound 70
4-chloro-N-(1-((1R,3s,5S,6r)-3-((7-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 71
4-chloro-N-(1-((1R,3s,5S,6r)-3-((3-methylpyridin-2-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 72
4-chloro-N-(1-((1R,3s,5S,6r)-3-(phthalazin-1-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 73
4-chloro-N-(1-((1R,3s,5S,6r)-3-
morpholinobicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 74
N-(1-((1R,3s,5S,6r)-3-(6-fluoro-4-oxoquinazolin-3(4H)-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-6-
methoxynicotinamide
Compound 75
5-chloro-N-(1-((1R,3s,5S,6r)-3-(6-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)picolinamide
Compound 76
5-cyano-N-(1-((1R,3s,5S,6r)-3-(6-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)picolinamide
Compound 77
5-chloro-N-(1-((1R,5S)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)picolinamide
Compound 78
N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)-6-
methoxynicotinamide
Compound 79
2-(4-chlorophenyl)-N-((1R,3s,5S,6r)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)acetamide
Compound 80
N-(1-((1R,3s,5S,6r)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)-4-
cyanobenzamide
Compound 81
N-(1-((1R,3s,5S,6r)-3-(1H-1,2,4-triazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 82
N-(1-((1R,3s,5S,6r)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)-5-
cyanopicolinamide
Compound 83
5-cyano-N-(1-((1R,3s,5S,6r)-3-(4-oxocinnolin-1(4H)-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)picolinamide
Compound 84
ethyl 3-(4-chlorobenzamido)-3-((1R,3s,5S,6r)-3-
(cinnolin-4-yloxy)bicyclo[3.1.0]hexan-6-yl)propanoate
Compound 85
2-(4-chlorophenyl)-N-((1R,3s,5S,6r)-3-(4-oxocinnolin-
1(4H)-yl)bicyclo[3.1.0]hexan-6-yl)acetamide
Compound 86
2-(4-chlorophenyl)-N-((1R,3s,5S,6r)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)-N-methylacetamide
Compound 87
4-cyano-N-(2-((1R,5S)-3-(4-oxocinnolin-1(4H)-
yl)bicyclo[3.1.0]hexan-6-yl)propan-2-yl)benzamide
Compound 88
N-(2-((1R,5S)-3-(cinnolin-4-yloxy)bicyclo[3.1.0]hexan-
6-yl)propan-2-yl)-4-cyanobenzamide
Compound 89
N-(1-((1R,3s,5S,6r)-3-(1H-benzo[d]imidazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 90
N-(1-((1R,3s,5S,6r)-3-azidobicyclo[3.1.0]hexan-6-
yl)propyl)-4-chlorobenzamide
Compound 91
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-cyclopropyl-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 92
4-chloro-N-(1-((1R,3s,5S,6r)-3-((4-chloro-2-
methylpyridin-3-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 93
4-chloro-N-(1-((1R,3s,5S,6r)-3-((3-fluoro-2-
methylpyridin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 94
1-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-1H-
1,2,3-triazole-4-carboxylic acid
Compound 95
1-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-1H-
1,2,3-triazole-4-carboxamide
Compound 96
4-chloro-N-(1-((1R,3s,5S,6r)-3-((tetrahydro-2H-pyran-
4-yl)methoxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 97
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-(2-hydroxypropan-2-
yl)-1H-1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 98
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-(pyrrolidine-1-
carbonyl)-1H-1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 99
N-(1-((1R,3s,5S,6r)-3-(1H-benzo[d][1,2,3]triazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 100
N-(1-((1R,3s,5S,6r)-3-(2H-benzo[d][1,2,3]triazol-2-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 101
4-chloro-N-(1-((1R,3s,5S,6r)-3-((tetrahydro-2H-pyran-
4-yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 102
4-cyano-N-(1-((1R,3s,5S,6r)-3-((7-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 103
4-chloro-N-((S)-1-((1R,3R,5S,6r)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 104
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 105
4-cyano-N-(1-((1R,3r,5S,6r)-3-
hydroxybicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 106
4-cyano-N-(1-((1R,3s,5S,6r)-3-
hydroxybicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 107
4-cyano-N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 108
4-cyano-N-(1-((1R,3s,5S,6r)-3-(6-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 109
2-(4-Chlorophenyl)-N-(3-(6-fluoroquinolin-4-yl)-3-
azabicyclo[3.1.0]hexan-6-yl)acetamide
Compound 110
N-(3-(6-fluoroquinolin-4-yl)-3-azabicyclo[3.1.0]hexan-
6-yl)-3-hydroxy-2-phenylpropanamide
Compound 111
2-(4-bromophenyl)-N-(3-(6-fluoroquinolin-4-yl)-3-
azabicyclo[3.1.0]hexan-6-yl)-2-hydroxyacetamide
Compound 112
2-(5-chloro-3-fluoropyridin-2-yl)-N-(3-(6-
fluoroquinolin-4-yl)-3-azabicyclo[3.1.0]hexan-6-
yl)acetamide
Compound 113
N-(1-((1R,5S,6R)-bicyclo[3.1.0]hex-2-en-6-yl)propyl)-
4-chlorobenzamide
Compound 114
4-chloro-N-(1-((1R,3s,5S,6r)-3-(2,3-dioxoindolin-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 115
N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)ethyl)-6-
methoxynicotinamide
Compound 116
4-chloro-N-(1-((1R,3s,5S,6r)-3-
(phenylsulfonamido)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 117
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)picolinamide
Compound 118
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)quinoline-2-carboxamide
Compound 119
4-chloro-N-(1-((1R,3s,5S,6r)-3-(3,3-difluoro-2-
oxoindolin-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 120
4-cyano-N-(1-((1R,3s,5S,6r)-3-(7-fluoro-4-
oxoquinazolin-3(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 121
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-fluoro-2-oxoindolin-
1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 122
4-chloro-N-(1-((1R,3s,5S,6r)-3-(3,3-dimethyl-2,5-
dioxopyrrolidin-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 123
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-4-
yl)amino)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 124
N-(1-((1R,3s,5S,6r)-3-((7-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)ethyl)-6-
methoxynicotinamide
Compound 125
4-chloro-N-(1-((1R,3s,5S,6r)-3-(6-fluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 126
4-chloro-N-(1-((1R,3r,5S,6r)-3-((6-fluoroquinolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 127
4-chloro-N-(1-((1R,3r,5S,6r)-3-((4-chloroquinolin-6-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 128
N-(1-((1R,3s,5S,6r)-3-hydroxybicyclo[3.1.0]hexan-6-
yl)ethyl)-6-methoxynicotinamide
Compound 129
4-cyano-N-(1-((1R,3s,5S,6r)-3-(4-cyclopropyl-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 130
4-cyano-N-((R)-1-((1R,3S,5S,6r)-3-((6-
fluoroquinazolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 131
4-cyano-N-((S)-1-((1R,3R,5S,6r)-3-((6-
fluoroquinazolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 132
4-cyano-N-((R)-1-((1R,3S,5S,6r)-3-((7-
fluoroquinazolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 133
4-cyano-N-((S)-1-((1R,3R,5S,6r)-3-((7-
fluoroquinazolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 134
Ethyl 3-(4-chlorobenzamido)-3-((1R,3s,5S,6r)-3-((6-
fluoroquinazolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanoate
Compound 135
N-(1-((1R,3s,5S,6r)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)ethyl)-4-
cyanobenzamide
Compound 136
4-cyano-N-(1-((1R,3s,5S,6r)-3-(4-oxocinnolin-1(4H)-
yl)bicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 137
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-fluoroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)-3-
hydroxypropyl)benzamide
Compound 138
4-chloro-N-(1-((1R,3r,5S,6r)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 139
4-chloro-N-(1-((1R,3s,5S,6r)-3-(cinnolin-4-
yloxy)bicyclo[3.1.0]hexan-6-yl)-3-
hydroxypropyl)benzamide
Compound 140
4-chloro-N-(3-hydroxy-1-((1R,3s,5S,6r)-3-(4-
oxocinnolin-1(4H)-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 141
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(4-(2-
hydroxypropan-2-yl)-1H-1,2,3-triazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 142
4-chloro-N-((S)-1-((1R,3R,5S,6r)-3-(4-(2-
hydroxypropan-2-yl)-1H-1,2,3-triazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 143
N-((1R,3s,5S,6r)-6-(1-(4-
cyanobenzamido)ethyl)bicyclo[3.1.0]hexan-3-
yl)picolinamide
Compound 144
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-5-
fluoropicolinamide
Compound 145
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)nicotinamide
Compound 146
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-(hydroxymethyl)-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 147
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-(prop-1-en-2-yl)-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 148
3-(4-chlorobenzamido)-3-((1R,3s,5S,6r)-3-((6-
fluoroquinazolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanoic acid
Compound 149
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)pyrimidine-4-carboxamide
Compound 150
6-chloro-N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)pyrazine-2-carboxamide
Compound 151
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)pyridazine-3-carboxamide
Compound 152
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)pyrazine-2-carboxamide
Compound 153
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-cyclopropyl-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 154
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-(2-hydroxypropan-2-
yl)-1H-1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 155
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-(hydroxymethyl)-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 156
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)piperazine-1-carboxamide
Compound 157
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)morpholine-4-carboxamide
Compound 158
3-chloro-N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-4-
(trifluoromethyl)picolinamide
Compound 159
4-chloro-N-(1-((1R,3s,5S,6r)-3-
(methylsulfonamido)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 160
4-chloro-N-(1-((1R,3s,5S,6r)-3-((1-
methylcyclopropane)-1-
sulfonamido)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 161
4-chloro-N-(1-((1R,3s,5S,6r)-3-(1,3-dioxoisoindolin-2-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 162
4-chloro-N-(1-((1R,3s,5S,6r)-3-(6-fluoro-1H-indazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 163
4-chloro-N-(1-((1R,3s,5S,6r)-3-(6-fluoro-2H-indazol-2-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 164
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-5-
methoxypicolinamide
Compound 165
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-ethyl-1H-1,2,3-
triazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 166
4-chloro-N-(1-((1R,3s,5S,6r)-3-
(cyano(phenyl)methyl)bicyclo[3.1.0]hexan-6-yl)
propyl)benzamide
Compound 167
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-ethyl-1H-1,2,3-
triazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 168
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-cyclopropyl-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-yl)-2-
hydroxyethyl)benzamide
Compound 169
Methyl 2-(4-chlorobenzamido)-2-((1R,3s,5S,6r)-3-(4-
cyclopropyl-1H-1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-
6-yl)acetate
Compound 170
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-5-
fluoronicotinamide
Compound 171
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-3,5-
difluoropicolinamide
Compound 172
4-chloro-N-(1-((1R,3s,5S,6r)-3-(3-cyclopropyl-4H-
1,2,4-triazol-4-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 173
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-cyclopropyl-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-yl)-2-
methoxyethyl)benzamide
Compound 174
N-(1-((1R,3s,5S,6r)-3-(1H-pyrazolo[3,4-c]pyridin-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 175
4-chloro-N-(1-((1R,3s,5S,6r)-3-(1-oxoisoindolin-2-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 176
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5,6-dichloro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 177
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-1H-
pyrazole-4-carboxamide
Compound 178
N-(1-((1R,3s,5S,6r)-3-(6-bromo-1H-
benzo[d][1,2,3]triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)-4-chlorobenzamide
Compound 179
N-(1-((1R,3s,5S,6r)-3-(5-bromo-2H-
benzo[d][1,2,3]triazol-2-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)-4-chlorobenzamide
Compound 180
4-chloro-N-(1-((1R,3s,5S,6r)-3-(2-oxo-2,3-dihydro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 181
4-chloro-N-(1-((1R,3s,5S,6r)-3-(3-methyl-2-oxo-2,3-
dihydro-1H-benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-
6-yl)propyl)benzamide
Compound 182
N-(1-((1R,3s,5S,6r)-3-(4H-imidazo[4,5-b]pyridin-4-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 183
N-(1-((1R,3s,5S,6r)-3-(1H-imidazo[4,5-b]pyridin-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 184
N-(1-((1R,3s,5S,6r)-3-(3H-imidazo[4,5-b]pyridin-3-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 185
4-chloro-N-(1-((1R,3s,5S,6r)-3-(2-oxooxazolidin-3-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 186
4-chloro-N-(1-((1R,3r,5S,6r)-3-(4-cyclopropyl-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 187
4-chloro-N-(1-((1R,3r,5S,6r)-3-(4-(hydroxymethyl)-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 188
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-3-
fluoropicolinamide
Compound 189
4-chloro-N-(1-((1R,3s,5S,6r)-3-(3-methyl-3-(pyridin-2-
yl)ureido)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 190
Ethyl 2-(((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)amino)-2-phenylacetate
Compound 191
4-chloro-N-(1-((1R,3r,5S,6r)-3-(5-cyclopropyl-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 192
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-fluoro-2-oxo-2,3-
dihydro-1H-benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-
6-yl)propyl)benzamide
Compound 193
4-chloro-N-(1-((1R,3s,5S,6r)-3-((6-fluoro-1H-
benzo[d]imidazol-2-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 194
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-fluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 195
4-chloro-N-(1-((1R,3s,5S,6r)-3-(7-fluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 196
N-(1-((1R,3s,5S,6r)-3-(1H-imidazo[4,5-c]pyridin-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 197
N-(1-((1R,3s,5S,6r)-3-(3H-imidazo[4,5-c]pyridin-3-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 198
N-(1-((1R,3s,5S,6r)-3-(5H-imidazo[4,5-c]pyridin-5-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 199
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-fluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 200
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-phenyl-1H-imidazol-
1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 201
4-chloro-N-(1-((1R,3s,5S,6r)-3-(2-methyl-1H-imidazol-
1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 202
methyl (S/R)-2-((1R,3S,5S,6S)-6-((R/S)-1-(4-
chlorobenzamido)propyl)bicyclo [3.1.0]hexan-3-yl)-2-
phenylacetate
Compound 203
methyl (S/R)-2-((1R,3R,5S,6S)-6-((S/R)-1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-2-
phenylacetate
Compound 204
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-phenyl-2H-1,2,3-
triazol-2-yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 205
4-chloro-N-(1-((1R,3s,5S,6r)-3-(7-fluoro-2H-indazol-2-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 206
4-chloro-N-(1-((1R,3s,5S,6r)-3-(7-fluoro-1H-indazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 207
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-fluoro-2H-indazol-2-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 208
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-fluoro-1H-indazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 209
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-fluoro-2H-indazol-2-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 210
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-fluoro-1H-indazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 211
N-(1-((1R,3s,5S,6r)-3-(2H-pyrazolo[3,4-b]pyridin-2-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 212
N-(1-((1R,3s,5S,6r)-3-(1H-pyrazolo[3,4-b]pyridin-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 213
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4,6-difluoro-2H-
benzo[d][1,2,3]triazol-2-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 214
4-chloro-N-(1-((1R,3r,5S,6r)-3-(4-(methoxymethyl)-
1H-1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 215
4-chloro-N-(1-((1R,3r,5S,6r)-3-(4-((2-
methoxyethoxy)methyl)-1H-1,2,3-triazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 216
4-chloro-N-(1-((1R,3r,5S,6r)-3-(4-(ethoxymethyl)-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 217
2-(((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)amino)-2-phenylacetic acid
Compound 218
3-chloro-N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)picolinamide
Compound 219
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-4-
(trifluoromethyl)nicotinamide
Compound 220
N-((1R,3r,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-3-
fluoropicolinamide
Compound 221
N-((1R,3r,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-5-
fluoropicolinamide
Compound 222
3-chloro-N-((1R,3r,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-4-
(trifluoromethyl)picolinamide
Compound 223
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-2-
methylnicotinamide
Compound 224
4-chloro-N-(1-((1R,3s,5S,6r)-3-((2-(methylamino)-2-
oxo-1-phenylethyl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 225
N-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-4-
(trifluoromethyl)picolinamide
Compound 226
4-chloro-N-(1-((1R,3s,5S,6r)-3-(pyridin-2-
ylamino)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 227
4-chloro-N-(1-((1R,3s,5S,6r)-3-((5-fluoropyridin-2-
yl)amino)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 228
2-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-2-
phenylacetic acid
Compound 229
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-fluoro-1H-indol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 230
4-chloro-N-((R/S)-1-((1R,3S,5S,6S)-3-((S/R)-2-
(methylamino)-2-oxo-1-phenylethyl)bicyclo[3.1.0]hexan-
6-yl)propyl)benzamide
Compound 231
4-chloro-N-((R/S)-1-((1R,3S,5S,6S)-3-((R/S)-2-
(methylamino)-2-oxo-1-phenylethyl)bicyclo[3.1.0]hexan-
6-yl)propyl)benzamide
Compound 232
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-(1,3-dioxoisoindolin-
2-yl)-1H-1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 233
3-(1-((1R,3s,5S,6r)-6-(1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-1H-
1,2,3-triazol-4-yl)azetidine-1-carboxylate
Compound 234
4-chloro-N-(1-((1R,3s,5S,6r)-3-(6-cyano-3H-
imidazo[4,5-b]pyridin-3-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 235
4-chloro-N-(1-((1R,3s,5S,6r)-3-(6-cyano-1H-
imidazo[4,5-b]pyridin-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 236
4-chloro-N-(1-((1R,3s,5S,6r)-3-((5-fluoro-3-
nitropyridin-2-yl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 237
N-(1-((1R,3s,5S,6r)-3-(4-(azetidin-3-yl)-1H-1,2,3-
triazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-
chlorobenzamide
Compound 238
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-(dimethylamino)-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 239
N-(1-((1R,3s,5S,6r)-3-(4-amino-1H-1,2,3-triazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 240
4-chloro-N-(1-((1R,3s,5S,6r)-3-(6-fluoro-3H-
imidazo[4,5-b]pyridin-3-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 241
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 242
4-cyano-N-(1-((1R,3s,5S,6r)-3-(4-(methoxymethyl)-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 243
4-chloro-N-(1-((1R,3s,5S,6r)-3-((3,5-difluoro-2-
nitrophenyl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 244
4-chloro-N-(1-((1R,3s,5S,6r)-3-((2,3-difluoro-6-
nitrophenyl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 245
4-chloro-N-(1-((1R,3s,5S,6r)-3-(6,7-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 246
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 247
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(6-fluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 248
4-chloro-N-((S)-1-((1R,3S,5S,6r)-3-(6-fluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 249
(1R,5S,6s)-N-(4-chlorobenzyl)-3-(6-fluoroquinazolin-4-
yl)-3-azabicyclo[3.1.0]hexane-6-carboxamide
Compound 250
(1R,5S,6s)-N-(4-chlorophenyl)-3-(6-fluoroquinazolin-4-
yl)-3-azabicyclo[3.1.0]hexane-6-carboxamide
Compound 251
(1R,5S,6r)-N-(4-chlorobenzyl)-3-(6-fluoroquinazolin-4-
yl)-3-azabicyclo[3.1.0]hexane-6-carboxamide
Compound 252
(1R,5S,6r)-N-(4-chlorophenyl)-3-(6-fluoroquinazolin-4-
yl)-3-azabicyclo[3.1.0]hexane-6-carboxamide
Compound 253
4-chloro-N-(1-((1R,3s,5S,6r)-3-((7-chloroquinazolin-4-
yl)oxy)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 254
4-chloro-N-(1-((1R,5R,6S)-3-(5-
(trifluoromethyl)pyridin-3-yl)bicyclo[3.1.0]hex-2-en-6-
yl)propyl)benzamide
Compound 255
4-chloro-N-(1-((1R,5R,6S)-3-(7-fluoroquinazolin-4-
yl)bicyclo[3.1.0]hex-2-en-6-yl)propyl)benzamide
Compound 256
N-(1-((1R,3s,5S,6r)-3-(4-acetamido-1H-1,2,3-triazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 257
N-(1-((1R,3s,5S,6r)-3-(4-(1-acetylazetidin-3-yl)-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-
chlorobenzamide
Compound 258
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-cyclopropyl-1H-
1,2,4-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 259
4-chloro-N-(1-((1R,3s,5S,6r)-3-(3-cyclopropyl-1H-
1,2,4-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 260
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 261
4-chloro-N-(1-((1R,3s,5S,6r)-3-(4-cyclopropyl-1H-
imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 262
4-chloro-N-(1-((1R,3S,5S,6r)-3-(4-(propen-2-yl)-1H-
1,2,3-triazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 263
4-chloro-N-(1-((1R,3s,5S,6r)-3-(pyrazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 264
4-chloro-N-(1-((1R,3s,5S,6r)-3-((2,4-difluoro-6-
nitrophenyl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 265
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 266
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(6-fluoroquinolin-
4-yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 267
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5,7-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 268
4-cyano-N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 269
4-chloro-N-(1-((1R,3s,5S,6r)-3-((4-cyano-2-
nitrophenyl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 270
4-chloro-N-(1-((1R,3s,5S,6r)-3-((4-chloro-2-
nitrophenyl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 271
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-cyano-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 272
4-chloro-N-(1-((1R,3s,5S,6r)-3-(5-chloro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 273
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(6-chloro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 274
4-cyano-N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)ethyl)benzamide
Compound 275
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(6-fluoro-2-methyl-
1H-benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 276
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(6-fluoro-2-
(trifluoromethyl)-1H-benzo[d]imidazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 277
4-cyano-N-((R)-1-((1R,3S,5S,6r)-3-(6-fluoroquinolin-4-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 278
4-cyano-N-((R)-1-((1R,3S,5S,6r)-3-(6-fluoroquinolin-4-
yl)bicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 279
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(6-
fluoroquinazolin-4-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 280
4-chloro-N-(((1R,5S,6s)-3-(6-fluoroquinazolin-4-yl)-3-
azabicyclo[3.1.0]hexan-6-yl)methyl)benzamide
Compound 281
N-(4-chlorophenyl)-2-((1R,3s,5S,6r)-3-(5,6-difluoro-
1H-benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propanamide
Compound 282
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(6-cyano-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 283
N-((1R)-1-((1R,5S,6r)-3-azidobicyclo[3.1.0]hexan-6-
yl)propyl)-4-cyanobenzamide
Compound 284
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-((5-chloro-2-
nitrophenyl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 285
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(6-fluoroquinolin-
4-yl)bicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 286
4-chloro-N-((R)-1-((1R,3R,5S,6r)-3-(6-fluoroquinolin-
4-yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 287
4-chloro-N-(2-((1R,3s,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propan-
2-yl)benzamide
Compound 288
4-cyano-N-((R)-1-((1R,3S,5S,6r)-3-(6-cyano-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 289
N-((R)-1-((1R,3S,5S,6r)-3-(6-chloro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)-4-cyanobenzamide
Compound 290
diethyl 2-((1R,3S,5S,6r)-6-((R)-1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)malonate
Compound 291
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(1,3-
dihydroxypropan-2-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 292
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(1-cyclopropyl-1H-
pyrazol-4-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 293
4-cyano-N-((R)-1-((1R,3S,5S,6r)-3-(6-cyano-2-methyl-
1H-benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 294
N-((R)-1-((1R,3S,5S,6r)-3-(6-chloro-2-methyl-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)-4-cyanobenzamide
Compound 295
4-cyano-N-((1R)-1-((1R,3S,5S,6r)-3-(4-
(tetrahydrofuran-3-yl)-1H-1,2,3-triazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)benzamide
Compound 296
4-cyano-N-((R)-1-((1R,3R,5S,6r)-3-
hydroxybicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 297
4-cyano-N-((R)-1-((1R,3S,5S,6r)-3-
hydroxybicyclo[3.1.0]hexan-6-yl)ethyl)benzamide
Compound 298
(R)-N-(4-chlorophenyl)-2-((1R,3S,5S,6r)-3-(5,6-
difluoro-1H-benzo[d]imidazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propanamide
Compound 299
(S)-N-(4-chlorophenyl)-2-((1R,3R,5S,6r)-3-(5,6-
difluoro-1H-benzo[d]imidazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propanamide
Compound 300
dimethyl 1-((1R,3S,5S,6r)-6-((R)-1-(4-
cyanobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-1H-
1,2,3-triazole-4,5-dicarboxylate
Compound 301
4-chloro-N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)methyl)benzamide
Compound 302
4-cyano-N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)methyl)benzamide
Compound 303
4-chloro-N-((R)-1-((1R,3R,5S,6r)-3-(5-
cyclopropylpyridin-3-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 304
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(4-iodo-1H-
pyrazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 305
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(4-vinyl-1H-
pyrazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 306
N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)-4-fluorobenzamide
Compound 307
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)-3-fluorobenzamide
Compound 308
N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)-2-methylisonicotinamide
Compound 309
N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)-2-methylthiazole-4-carboxamide
Compound 310
3-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 311
N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)-6-methylnicotinamide
Compound 312
N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)-3-fluorobenzamide
Compound 313
3-cyano-N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 314
N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-benzo[d]imidazol-
1-yl)bicyclo[3.1.0]hexan-6-yl)methyl)-4-
fluorobenzamide
Compound 315
4-chloro-N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)methyl)-3-fluorobenzamide
Compound 316
3-chloro-N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)methyl)benzamide
Compound 317
N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-benzo[d]imidazol-
1-yl)bicyclo[3.1.0]hexan-6-yl)methyl)-6-
methylnicotinamide
Compound 318
N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-benzo[d]imidazol-
1-yl)bicyclo[3.1.0]hexan-6-yl)methyl)-6-
methoxynicotinamide
Compound 319
N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-benzo[d]imidazol-
1-yl)bicyclo[3.1.0]hexan-6-yl)methyl)-1-methyl-1H-
pyrazole-4-carboxamide
Compound 320
N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-benzo[d]imidazol-
1-yl)bicyclo[3.1.0]hexan-6-yl)methyl)-3-
fluorobenzamide
Compound 321
3-cyano-N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)methyl)benzamide
Compound 322
N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-benzo[d]imidazol-
1-yl)bicyclo[3.1.0]hexan-6-yl)methyl)-4-
methylbenzamide
Compound 323
N-(((1R,3s,5S,6r)-3-(5,6-difluoro-1H-benzo[d]imidazol-
1-yl)bicyclo[3.1.0]hexan-6-yl)methyl)-3-
methylbenzamide
Compound 324
N-((R)-1-((1R,3S,5S,6r)-3-(1H-pyrazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 325
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(4-cyano-1H-
pyrazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 326
methyl 1-((1R,3S,5S,6r)-6-((R)-1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-1H-
pyrazole-4-carboxylate
Compound 327
N-((1R,3S,5S,6r)-6-((R)-1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-3-
fluoropicolinamide
Compound 328
1-((1R,3S,5S,6r)-6-((R)-1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-1H-
pyrazole-4-carboxylic acid
Compound 329
N-((R)-1-((1R,3S,5S,6r)-3-(4-bromo-1H-pyrazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)-4-chlorobenzamide
Compound 330
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(4-methyl-1H-
pyrazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 331
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-((2-
cyanophenyl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 332
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(4-
(trifluoromethyl)-1H-pyrazol-1-yl)bicyclo[3.1.0]hexan-
6-yl)propyl)benzamide
Compound 333
N-((1R,3S,5S,6r)-6-((R)-1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)picolinamide
Compound 334
N-((1R,3S,5S,6r)-6-((R)-1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-yl)-5-
fluoronicotinamide
Compound 335
N-((1R,3S,5S,6r)-6-((R)-1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)nicotinamide
Compound 336
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-((6-
fluoroquinazolin-4-yl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 337
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-((6-
ethynylquinazolin-4-yl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 338
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-((6-
methylquinazolin-4-yl)amino)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 339
N-(4-chlorophenyl)-2-((1R,3s,5S,6r)-3-((6-
fluoroquinazolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanamide
Compound 340
N-(4-chlorophenyl)-2-((1R,3s,5S,6r)-3-((6-
fluorocinnolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanamide
Compound 341
4-chloro-2-(((1R,3S,5S,6r)-6-((R)-1-(4-
chlorobenzamido)ethyl)bicyclo[3.1.0]hexan-3-
yl)oxy)benzoic acid
Compound 342
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(5-cyclopropyl-1H-
pyrazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 343
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(3-cyclopropyl-1H-
pyrazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 344
1-(4-chlorophenyl)-3-((R)-1-((1R,3S,5S,6r)-3-(5,6-
difluoro-1H-benzo[d]imidazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)urea
Compound 345
N-(4-chloro-3-fluorophenyl)-2-((1R,3s,5S,6r)-3-(5,6-
difluoro-1H-benzo[d]imidazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propanamide
Compound 346
2-(((1R,3S,5S,6r)-6-((R)-1-(4-
chlorobenzamido)propyl)bicyclo[3.1.0]hexan-3-
yl)amino)benzoic acid
Compound 347
N-(4-chlorophenyl)-2-((1R,3s,5S,6r)-3-((6-
fluoroquinolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanamide
Compound 348
4-chloro-N-((R)-1-((1R,3S,5S,6r)-3-(4-cyclopropyl-1H-
pyrazol-1-yl)bicyclo[3.1.0]hexan-6-
yl)propyl)benzamide
Compound 349
1-(4-chloro-3-fluorophenyl)-3-((R)-1-((1R,3S,5S,6r)-3-
(5,6-difluoro-1H-benzo[d]imidazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propyl)urea
Compound 350
(R)-N-(4-chlorophenyl)-2-((1R,3S,5S,6r)-3-((6-
fluoroquinazolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanamide
Compound 351
(S)-N-(4-chlorophenyl)-2-((1R,3R,5S,6r)-3-((6-
fluoroquinazolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanamide
Compound 352
N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)-
1-(trifluoromethyl)cyclopropane-1-carboxamide
Compound 353
1-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)-
3-(oxetan-3-yl)urea
Compound 354
N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)-
3,3-difluoroazetidine-1-carboxamide
Compound 355
N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)-
4,4-difluoropiperidine-1-carboxamide
Compound 356
N-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-1H-
benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)morpholine-
4-carboxamide
Compound 357
1-cyclopropyl-3-((R)-1-((1R,3S,5S,6r)-3-(5,6-difluoro-
1H-benzo[d]imidazol-1-yl)bicyclo[3.1.0]hexan-6-yl)propyl)urea
Compound 358
(R)-N-(4-chlorophenyl)-2-((1R,3s,5S,6r)-3-((6-
fluorocinnolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanamide
Compound 359
(S)-N-(4-chlorophenyl)-2-((1R,3s,5S,6r)-3-((6-
fluorocinnolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanamide
Compound 360
(R)-N-(4-chloro-3-fluorophenyl)-2-((1R,3s,5S,6r)-3-
(5,6-difluoro-1H-benzo[d]imidazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propanamide
Compound 361
(S)-N-(4-chloro-3-fluorophenyl)-2-((1R,3s,5S,6r)-3-
(5,6-difluoro-1H-benzo[d]imidazol-1-
yl)bicyclo[3.1.0]hexan-6-yl)propanamide
Compound 362
(R)-N-(4-chlorophenyl)-2-((1R,3s,5S,6r)-3-((6-
fluoroquinolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanamide
Compound 363
(S)-N-(4-chlorophenyl)-2-((1R,3s,5S,6r)-3-((6-
fluoroquinolin-4-yl)oxy)bicyclo[3.1.0]hexan-6-
yl)propanamide
and the pharmaceutically acceptable salts and prodrugs thereof.

1,321 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/478,076Filed 16 Jan 2018
Priority: 17 Jan 2017
Published: 5 Dec 2019
Term ends: Not estimatedThe source records don’t support an estimate.

Classification87 codes

A61K 31/015
Hydrocarbons: carbocyclic
A61K 31/4192
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: 1,2,3-Triazoles
A61K 31/166
Having aromatic rings, e.g. colchicine, atenolol, progabide: having the carbon of a carboxamide group directly attached to the aromatic ring, e.g.…
A61K 31/18
Amides, e.g. hydroxamic acids: sulfonamides

Family

Application62/447,368Us provisional application · filed 17 Jan 2017
Application62/458,777Us provisional application · filed 14 Feb 2017
Application62/528,366Us provisional application · filed 3 Jul 2017
US 11,173,145 B2Related patent
US 2019/0365718 A1This patent

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

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Abstract

A compound characterised by formula (VII),

or a pharmaceutically acceptable salt or prodrug thereof, wherein one but not both of the dashed bonds may optionally be a carbon-carbon double bond, and wherein:
W is selected from C, CH, and N;
a is 0 or 1;
b is 0, 1 or 2;
c is 0 or 1;
d is 0 or 1;
e is 0 or 1;
f is 0, 1 or 2;
A is selected from O, C(O), and S(O)2;
J is in each case independently selected from oxo, OH, CN, halogen, and C1-3-alkyl;
X1 is selected from C(R8)(R9), N(R10), O, and S;
X2 is selected from C(R11)(R12), N(R13), and O;
Y is selected from
C6-10-aryl, and
5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
wherein said aryl and heteroaryl are optionally substituted by one or more groups independently selected from R14;
R1 is selected from
H,
(G)n-(C1-6-alkyl),
(G)n-(C3-8-cycloalkyl),
N3,
(G)n-heterocycloalkyl, wherein said heterocycloalkyl is a 3- to 6-membered heterocycloalkyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
(G)n-(C5-8-cycloalkenyl),
(G)n-heterocycloalkenyl, wherein said heterocycloalkenyl is a 5- to 6-membered heterocycloalkenyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
(G)n-(C6-10-aryl), and
(G)n-heteroaryl, wherein said heteroaryl is a 5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
wherein G in each case is independently selected from C(R8)(R9), C(O), S(O)2, C(O)NR10, and S(O)2NR10;
and wherein n in each case is either 0 or 1, and
wherein said alkyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl are optionally substituted by one or more groups independently selected from R15;
R2, R3, R4, R6, R7, R8, R9, R11 and R12 are in each case independently selected from
H,
halogen,
CN,
OH,
(C0-4-alkyl)-SO2R17,
(C0-4-alkyl)-N(R18)2,
(C0-4-alkyl)-NHCOR19,
(C0-4-alkyl)-NHSO2R20,
(C0-4-alkyl)-CON(R21)2,
(C0-4-alkyl)-CO2R22,
(C0-4-alkyl)-SO2N(R23)2,
C1-6-alkyl,
O—(C1-6-alkyl),
C3-8-cycloalkyl,
3- to 6-membered heterocycloalkyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C5-8-cycloalkenyl,
5- to 6-membered heterocycloalkenyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C6-10-aryl, and
5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O, or
one or both geminal R3 and R4 pairs, taken together with the carbon atom to which they are attached, independently forms a 3- to 6-membered cycloalkyl group or a 3- to 6-membered heterocycloalkyl group which comprises 1, 2 or 3 ring heteroatoms selected from N, S and O,
wherein said alkyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl are optionally substituted by one or more groups independently selected from R16;
R5, R10 and R13 are in each case independently selected from
H,
C1-6-alkyl,
C3-8-cycloalkyl,
3- to 6-membered heterocycloalkyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C5-8-cycloalkenyl,
5- to 6-membered heterocycloalkenyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C6-10-aryl, and
5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
optionally wherein one of R3 and R5, together with one of R11 and R13 and the atoms intervening between them, may form a 5- or 6-membered cycloalkyl, cycloalkenyl or aryl group, or a 5- or 6-membered heterocycloalkyl, heterocycloalkenyl or heteroaryl group which comprises 1, 2, 3 or 4 ring heteroatoms selected from N, S and O;
wherein said alkyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl are optionally substituted by one or more groups independently selected from R24;
any two R14 substituents on adjacent ring atoms may, together with the ring atoms to which they are attached, independently form a 5- or 6-membered cyclic group optionally comprising 1, 2 or 3 ring heteroatoms selected from N, S and O, which cyclic group is optionally substituted by one or more groups independently selected from halogen, C1-4-alkyl and C1-4-haloalkyl, and
any remaining R14 is in each case independently selected from
halogen,
CN,
OH,
C1-6-alkyl,
O—(C1-6-alkyl),
O—(C1-6-haloalkyl),
O—(C1-6-alkyl-C3-6-cycloalkyl),
(C0-4-alkyl)-SO2R17,
(C0-4-alkyl)-N(R18)2,
(C0-4-alkyl)-NHCOR19,
(C0-4-alkyl)-NHSO2R20,
(C0-4-alkyl)-CON(R21)2,
(C0-4-alkyl)-CO2R22,
(C0-4-alkyl)-SO2N(R23)2, and
(C0-4-alkyl)-heteroaryl,
wherein said heteroaryl is a 5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O;
R15 is in each case independently selected from
halogen,
CN,
OH,
oxo,
NO2,
C1-6-alkyl,
C2-6-alkenyl,
C2-6-alkynyl,
(C0-4-alkyl)-O—(C1-6-alkyl),
(C0-4-alkyl)-SO2R17,
(C0-4-alkyl)-N(R18)2,
(C0-4-alkyl)-NHCOR19,
(C0-4-alkyl)-NHSO2R20,
(C0-4-alkyl)-CON(R21)2,
(C0-4-alkyl)-CO2R22,
(C0-4-alkyl)-SO2N(R23)2,
(C0-4-alkyl)-heteroaryl, wherein said heteroaryl is a 5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
(C0-4-alkyl)-heterocycloalkenyl, wherein said heterocycloalkenyl is a 5- to 10-membered heterocycloalkenyl comprising 1 or 2 ring heteroatoms selected from N and O,
(C0-4-alkyl)-heterocycloalkyl, wherein said heterocycloalkyl is a 4- to 6-membered heterocycloalkyl comprising 1 or 2 ring heteroatoms selected from N and O,
(C0-4-alkyl)-aryl, wherein said aryl is a 6- to 10-membered aryl,
(C0-4-alkyl)-cycloalkenyl, wherein said cycloalkenyl is a 5- to 8-membered cycloalkenyl, and
(C0-4-alkyl)-cycloalkyl, wherein said cycloalkyl is a 3- to 8-membered cycloalkyl,
wherein said alkyl, alkenyl, alkynyl, heteroaryl, heterocycloalkenyl, heterocycloalkyl, aryl, cycloalkenyl and cycloalkyl are optionally substituted by one or more groups independently selected from halogen, OH, O—(C1-4-alkyl), oxo, C(O)—(C1-4-alkyl), C(O)O—(C1-4-alkyl), and NH2;
R16 and R24 are in each case independently selected from
halogen,
CN,
OH,
C1-6-alkyl,
O—(C1-6-alkyl),
(C0-4-alkyl)-SO2R17,
(C0-4-alkyl)-N(R18)2,
(C0-4-alkyl)-NHCOR19,
(C0-4-alkyl)-NHSO2R20,
(C0-4-alkyl)-CON(R21)2,
(C0-4-alkyl)-CO2R22,
(C0-4-alkyl)-SO2N(R23)2,
(C0-4-alkyl)-heteroaryl, wherein said heteroaryl is a 5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
(C0-4-alkyl)-heterocycloalkenyl, wherein said heterocycloalkenyl is a 5- to 6-membered heterocycloalkenyl comprising 1 or 2 ring heteroatoms selected from N and O,
(C0-4-alkyl)-heterocycloalkyl, wherein said heterocycloalkyl is a 4- to 6-membered heterocycloalkyl comprising 1 or 2 ring heteroatoms selected from N and O,
(C0-4-alkyl)-aryl, wherein said aryl is a 6- to 10-membered aryl,
(C0-4-alkyl)-cycloalkenyl, wherein said cycloalkenyl is a 5- to 8-membered cycloalkenyl, and
(C0-4-alkyl)-cycloalkyl, wherein said cycloalkyl is a 3- to 8-membered cycloalkyl,
wherein said alkyl, heteroaryl, heterocycloalkenyl, heterocycloalkyl, aryl, cycloalkenyl and cycloalkyl are optionally substituted by one or more groups independently selected from halogen;
and
R17 to R23 are in each case independently selected from
H,
C1-6-alkyl,
C3-8-cycloalkyl,
3- to 6-membered heterocycloalkyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C5-8-cycloalkenyl,
5- to 6-membered heterocycloalkenyl comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
C6-10-aryl, and
5- to 10-membered heteroaryl comprising 1, 2, 3 or 4 ring heteroatoms selected from N, S and O,
wherein any pair of R18 groups attached to the same nitrogen atom, taken together with the intervening nitrogen atom, may form a 3- to 10-membered heterocycloalkyl or heterocycloalkenyl group comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
wherein any pair of R21 groups attached to the same nitrogen atom, taken together with the intervening nitrogen atom, may form a 3- to 10-membered heterocycloalkyl or heterocycloalkenyl group comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
wherein any pair of R23 groups attached to the same nitrogen atom, taken together with the intervening nitrogen atom, may form a 3- to 10-membered heterocycloalkyl or heterocycloalkenyl group comprising 1, 2 or 3 ring heteroatoms selected from N, S and O,
wherein each said alkyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl is optionally and independently substituted by one or more groups independently selected from halogen, OH, C1-6-alkyl and C1-6-haloalkyl.

135 more elements

Facts

Application

16/478,076Filed 16 Jan 2018

Priority

17 Jan 2017

Published

5 Dec 2019

Term ends

Not estimatedThe source records don’t support an estimate.

Classification87 codes

A61K 31/015
Hydrocarbons: carbocyclic
A61K 31/4192
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: 1,2,3-Triazoles
A61K 31/166
Having aromatic rings, e.g. colchicine, atenolol, progabide: having the carbon of a carboxamide group directly attached to the aromatic ring, e.g.…
A61K 31/18
Amides, e.g. hydroxamic acids: sulfonamides

Family

Application62/447,368Us provisional application · filed 17 Jan 2017

Application62/458,777Us provisional application · filed 14 Feb 2017

Application62/528,366Us provisional application · filed 3 Jul 2017

US 11,173,145 B2Related patent

US 2019/0365718 A1This patent

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