IP Library Granted Patent US 12692263
Granted Patent B2
US 12692263 · App. 18/268,914 · Granted Jul 28, 2026

SOS1 inhibitors and uses thereof

Inventors: Kailiang Wang (Shanghai, CN); Zhilong Hu (Shanghai, CN); Fei Zhang (Shanghai, CN); Wei Huang (Shanghai, CN); Teng Feng (Shanghai, CN); Fei Xiao (Shanghai, CN); Wenge Zhong (Thousand Oaks, CA)
Assignee: QILU REGOR THERAPEUTICS INC.
C07D471/04A61P35/00C07D519/00
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Quick Facts
Patent No.
US 12692263
App. No.
18/268,914
Granted
Jul 28, 2026
Kind
B2
Abstract

The present disclosure provides a compound of Formula (I) a pharmaceutically acceptable salt or a stereoisomer and their use in, e.g. treating a condition, disease or disorder in which the inhibition of the interaction of SOS 1 and a RAS-family protein or RAC1 is of therapeutic benefit, specifically in treating oncological diseases. This disclosure also features compositions containing the same as well as methods of using and making the same.

Claims (180)

1 . A compound of formula I:

a pharmaceutically acceptable salt or a stereoisomer thereof, wherein:

ring A is 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl;

R 1 is hydrogen, halogen, C 1-6 alkyl, or C 3-6 cycloalkyl, wherein said C 1-6 alkyl or C 3-6 cycloalkyl represented by R 1 is optionally substituted by one to more groups selected from halogen and —OH;

V is N or CR 2 ; wherein

R 2 is hydrogen, halogen, —CN, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, —OR 2a , —NR 2a R 2b , —C(O)R 2a , —C(O)OR 2a , —C(O)NR 2a R 2b , —SO 2 R 2a , —SO 2 NR 2a R 2b , —P(O)R 2a R 2b , —NR 2a C(O)R 2b , —NR 2a C(O)OR 2b , —NR 2a SO 2 R 2b , —NR 2a SO 2 NR 2b R 2c , 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl; wherein said C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl represented by R 2 is optionally substituted by one or more R 2d , wherein

R 2a , R 2b , and R 2c are independently selected from the group consisting of hydrogen, C 1-6 alkyl, 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, and 5-10 membered heteroaryl; or R 2a and R 2b or R 2b and R 2c together with the N or P atom to which they are attached form 4-12 membered heterocyclyl or 5-10 membered heteroaryl; wherein said C 1-6 alkyl, carbocyclyl, heterocyclyl, aryl, or heteroaryl represented by R 2a , R 2b , or R 2c are optionally substituted with one or more R 2d ; wherein

R 2d , in each occurrence, is hydrogen, halogen, oxo, —CN, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, —OR 2e , —NR 2e R 2f , —C(O)R 2e , —C(O)OR 2e , —C(O)NR 2e R 2f , —SO 2 R 2e , —SO 2 NR 2e R 2f , —P(O)R 2e R 2f , —NR 2e C(O)R 2f , —NR 2e C(O)OR 2f , —NR 2e SO 2 R 2f , —NR 2e SO 2 NR 2f R 2g , 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl;

R 2e , R 2f , and R 2g are independently selected from the group consisting of hydrogen and C 1-6 alkyl;

X is N or CR 3 ;

R 3 is hydrogen, halogen, or C 1-3 alkyl;

R 4 is hydrogen or C 1-6 alkyl;

R 5 is hydrogen, C 1-6 alkyl, 3-6 membered monocyclic carbocyclyl, or 4-6 membered monocyclic heterocyclyl; wherein said C 1-6 alkyl, 3-6 membered monocyclic carbocyclyl, or 4-6 membered monocyclic heterocyclyl represented by R 5 is optionally substituted with one or more groups selected from halogen and —OH;

R 6 is hydrogen, —OH, halogen, —CN, oxo, C 1-6 alkyl, C 1-6 alkoxy, —SO 2 R 6a , —SO 2 NR 6a R 6b , —P(O)R 6a R 6b , —C(O)NR 6a R 6b , —NR 6a C(O)R 6a , —NR 6a C(O)NR 6a R 6b , —(CH 2 ) s NR 6a R 6b , —O(CH 2 ) t NR 6a R 6b , 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, 5-10 membered heteroaryl; wherein said C 1-6 alkyl, C 1-6 alkoxy, 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl represented by R 6 is optionally substituted by one to more R 6c ; wherein

R 6a and R 6b are independently hydrogen or C 1-6 alkyl, or R 6a and R 6b together with the N or P atom to which they are attached form 4-7 membered heterocyclyl;

s is an integral from 0 to 3;

t is an integral from 2 to 4;

R 6c , in each occurrence, is hydrogen, —OH, halogen, —CN, oxo, C 1-6 alkyl, C 1-6 alkoxy, C 3-6 cycloalkyl, —NR 6a R 6b , —SO 2 R 6a , —SO 2 NR 6a R 6b , —C(O)NR 6a R 6b , —P(O)R 6a R 6b , —NR 6a C(O)R 6a , —NR 6a C(O)NR 6a R 6b , —(CH 2 ) s NR 6a R 6b , or

—O(CH 2 ) t NR 6a R 6b ; wherein said C 1-6 alkyl or C 3-6 cycloalkyl represented by R 6c is optionally substituted with one to more groups selected from halogen, —OH and —NR 6a R 6b ;

R 7 and R 8 are independently hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 2-6 alkoxy, 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl; wherein said C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 2-6 alkoxy, 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl represented by R 7 or R 8 is optionally substituted by one or more R 7a ; or

R 7 and R 8 together with the N atom to which they are attached form 4-12 membered heterocyclyl or 5-10 membered heteroaryl; wherein said 4-12 membered heterocyclyl or 5-10 membered heteroaryl is optionally substituted with one or more R 7 b;

R 7a is hydrogen, halogen, —CN, C 1-6 alkyl, —OR 7c , —NR 7c R 7d , —C(O)R 7c , —C(O)OR 7c , —C(O)NR 7c R 7d , —SO 2 R 7c , —P(O)R 7c R 7d , —SO 2 NR 7c R 7d , —NR 7c C(O)R 7d , —NR 7c C(O)OR 7d , —NR 7c SO 2 R 7d , —NR 7c SO 2 NR 7d R 7e , 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl, wherein said C 1-6 alkyl, 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl represented by R 7 ª is optionally substituted by one or more R 7f ;

R 7b is hydrogen, halogen, —CN, oxo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, —OR 7c , —NR 7c R 7d , —C(O)R 7c , —C(O)OR 7c , —C(O)NR 7c R 7d , —SO 2 R 7c , —P(O)R 7c R 7d , —SO 2 NR 7c R 7d , —NR 7c C(O)R 7d , —NR 7c C(O)OR 7d , —NR 7c SO 2 R 7d , —NR 7c SO 2 NR 7d R 7e , 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl, wherein C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, 3-12 membered carbocyclyl, 3-12 membered heterocyclyl, or 5-10 membered heteroaryl represented by R 7b is optionally substituted by one or more R 7f ;

R 7c , R 7d , and R 7e are independently selected from the group consisting of hydrogen, C 1-6 alkyl, 3-12 membered carbocyclyl, 4-12 membered heterocyclyl, 6-10 membered aryl, and 5-10 membered heteroaryl; or R 7c and R 7d together with the N or P atom to which they are attached form 4-12 membered heterocyclyl or 5-10 membered heteroaryl; wherein said C 1-6 alkyl, carbocyclyl, heterocyclyl, aryl, or heteroaryl represented by R 7c , R 7d , or R 7e is optionally substituted with one or more R 7f ;

R 7f , in each occurrence, is hydrogen, halogen, —CN, or —OH; and

n is 0, 1, 2, or 3;

wherein said heterocyclyl comprises 1-4 heteroatoms selected from O, N, and S; and said heteroaryl comprises 1-4 heteroatoms selected from O, N, and S.

2 . The compound of claim 1 or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein the compound is represented by Formula II:

3 . The compound of claim 2 , or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein

ring A is 3-10 membered carbocyclyl, 4-10 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl;

R 1 is hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl;

R 2 is hydrogen, halogen, —CN, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, —OR 2a , —NR 2a R 2b , —C(O)R 2a , —C(O)OR 2a , —C(O)NR 2a R 2b , —NR 2a C(O)R 2b , —NR 2a C(O)OR 2b , 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl; wherein said C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl represented by R 2 is optionally substituted by one to three R 2d ; wherein

R 2a and R 2b are independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, or C 1-6 hydroxyalkyl; or R 2a and R 2b together with the N atom to which they are attached form 4-12 membered heterocyclyl or 5-10 membered heteroaryl;

R 2d , in each occurrence, is hydrogen, halogen, oxo, —CN, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, —OR 2e , —NR 2e R 2f , —SO 2 R 2e , —P(O)R 2e R 2f , COOR 2e , CONR 2e R 2f , 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl;

R 2e and R 2f are independently selected from the group consisting of hydrogen and C 1-6 alkyl;

R 5 is hydrogen, C 1-4 alkyl, 3-5 membered monocyclic carbocyclyl, or 4-5 membered monocyclic heterocyclyl;

R 6 is hydrogen, —OH, halogen, —CN, oxo, C 1-6 alkyl, —(CH 2 ) s NR 6a R 6b , 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, 6-10 membered aryl, 5-10 membered heteroaryl; wherein said C 1-6 alkyl, 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl represented by R 6 is optionally substituted by one to more R 6c ; wherein

R 6a and R 6b are independently hydrogen or C 1-4 alkyl;

s is an integral from 0 to 2;

R 6c , in each occurrence, is hydrogen, —OH, halogen, —CN, oxo, C 1-6 alkyl, —NR 6a R 6b , or —(CH 2 )NR 6a R 6b ; wherein said C 1-6 alkyl represented by R 6c is optionally substituted with one to more groups selected from halogen and —OH;

R 7 and R 8 are independently hydrogen, C 1-4 alkyl, C 3-4 alkenyl, C 3-4 alkynyl, C 2-4 alkoxy, 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl; wherein said C 1-4 alkyl, C 3-4 alkenyl, C 3-4 alkynyl, C 2-4 alkoxy, 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl represented by R 7 or R 8 is optionally substituted by one or more R 7a ; or

R 7 and R 8 together with the N atom to which they are attached form 4-12 membered heterocyclyl or 5-10 membered heteroaryl; wherein said 4-12 membered heterocyclyl or 5-10 membered heteroaryl is optionally substituted with one to three R 7b ;

R 7a is hydrogen, halogen, —CN, C 1-6 alkyl, —OR 7c , or —NR 7c R 7d ,

R 7b is hydrogen, halogen, —CN, oxo, C 1-6 alkyl, C 1-6 alkoxy, —OR 7c , —NR 7c R 7d , —C(O)R 7c , —C(O)OR 7c , —SO 2 R 7c , or 5-10 membered heteroaryl, wherein C 1-6 alkyl, C 1-6 alkoxy, or 5-10 membered heteroaryl represented by R 7b is optionally substituted by one or more R 7f ;

R 7c and R 7d are independently selected from the group consisting of hydrogen, C 1-4 alkyl, 3-6 membered monocyclic carbocyclyl, 4-8 membered heterocyclyl, 6-10 membered aryl, and 5-10 membered heteroaryl; or R 7c and R 7d together with the N atom to which they are attached form 4-8 membered heterocyclyl or 5-10 membered heteroaryl; wherein said C 1-4 alkyl, 3-6 membered monocyclic carbocyclyl, 4-8 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl represented by R 7c or R 7d is optionally substituted with one to three R 7f ; and

R 7f , in each occurrence, is hydrogen, halogen, —CN, or —OH.

4 . The compound of claim 3 or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein

R 2 is hydrogen, halogen, —CN, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl; wherein said C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl represented by R 2 is optionally substituted by one to three R 2d ; wherein

R 2d , in each occurrence, is hydrogen, halogen, oxo, —CN, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, —OR 2e , —NR 2e R 2f , —SO 2 R 2e , —P(O)R 2e R 2f , COOR 2e , CONR 2e R 2f , 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl; and

R 2e and R 2f are independently selected from the group consisting of hydrogen and C 1-6 alkyl.

5 . The compound of claim 4 or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein

R 7 and R 8 are independently hydrogen, C 1-4 alkyl, C 3-4 alkenyl, C 3-4 alkynyl; wherein said C 1-4 alkyl, C 3-4 alkenyl, C 3-4 alkynyl represented by R 7 or R 8 is optionally substituted by one or more R 7a ; or

R 7 and R 8 together with the N atom to which they are attached form 4-12 membered heterocyclyl or 5 membered heteroaryl, each of which is optionally substituted with one to three R 7b ;

R 7a is hydrogen, halogen, —CN, C 1-6 alkyl, —OR 7c , or —NR 7c R 7d ;

R 7b is hydrogen, halogen, —CN, oxo, —OH, C 1-6 alkyl, C 1-6 alkoxy, —NR 7c R 7d , —C(O)R 7c , —C(O)OR 7c , —SO 2 R 7c , or 5-10 membered heteroaryl, wherein C 1-6 alkyl, C 1-6 alkoxy, or 5-10 membered heteroaryl represented by R 7b is optionally substituted by one or more R 7f ;

R 7c and R 7d are independently selected from the group consisting of hydrogen, C 1-4 alkyl, 3-6 membered monocyclic carbocyclyl, 4-8 membered heterocyclyl, 6-10 membered aryl, and 5-10 membered heteroaryl; or R 7c and R 7d together with the N atom to which they are attached form 4-8 membered heterocyclyl or 5-10 membered heteroaryl; wherein said C 1-4 alkyl, 3-6 membered monocyclic carbocyclyl, 4-8 membered heterocyclyl, 6-10 membered aryl, or 5-10 membered heteroaryl represented by R 7c or R 7d is optionally substituted with one to three R 7f ; and

R 7f , in each occurrence, is hydrogen, halogen, —CN, or −OH.

6 . The compound of claim 5 or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein

i) ring A is 3-6 membered monocyclic cycloalkyl, 4-6 membered monocyclic heterocyclyl, phenyl, or 5-10 membered heteroaryl;

R 6 is hydrogen, —OH, halogen, —CN, C 1-6 alkyl, or —(CH 2 ) s NR 6a R 6b ; wherein said C 1-6 alkyl represented by R 6 is optionally substituted with one to more groups selected from halogen and —OH;

R 6a and R 6b are independently hydrogen or C 1-4 alkyl; and

s is 0, or 1; or

ii) ring A is cyclopropyl, phenyl, thiophene, or indole.

7 . The compound of claim 1 or a pharmaceutically acceptable salt or stereoisomer thereof, wherein the compound is represented by Formula (III-A) or (III-B):

8 . The compound of claim 7 or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein R 6 is hydrogen, halogen, C 1-4 alkyl, or —(CH 2 )NR 6a R 6b ; wherein said C 1-4 alkyl represented by R 6 is optionally substituted with one to more groups selected from halogen and —OH; and R 6a and R 6b are independently hydrogen or C 1-4 alkyl.

9 . The compound of claim 8 or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein R 5 is hydrogen, methyl, or ethyl.

10 . The compound of claim 9 or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein

i) R 2 is hydrogen, halogen, —CN, C 1-4 alkyl, C 2-4 alkenyl, 3-6 membered monocyclic cycloalkyl, 5-6 membered monocyclic heterocyclyl, phenyl, or 5-10 membered heteroaryl; wherein said C 1-4 alkyl, 3-6 membered monocyclic cycloalkyl, 5-6 membered monocyclic heterocyclyl, phenyl, or 5-10 membered heteroaryl represented by R 2 is optionally substituted by one to three R 2d ;

R 2d , in each occurrence, is hydrogen, halogen, oxo, —CN, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, —OR 2e , —NR 2e R 2f , —SO 2 R 2e , —P(O)R 2e R 2f , COOR 2e , CONR 2e R 2f , 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, phenyl, or 5-10 membered heteroaryl; and

R 2e and R 2f are independently selected from the group consisting of hydrogen and C 1-6 alkyl;

ii) R 2 is phenyl or 5-10 membered heteroaryl; wherein said phenyl or 5-10 membered heteroaryl is optionally substituted by one to three R 2d ;

R 2d , in each occurrence, is hydrogen, halogen, —CN, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, —OR 2e , —NR 2e R 2f , —SO 2 R 2e , —P(O)R 2e R 2f , COOR 2e , CONR 2e R 2f , 3-6 membered monocyclic carbocyclyl, 3-6 membered monocyclic heterocyclyl, phenyl, or 5-10 membered heteroaryl; and

R 2e and R 2f are independently selected from the group consisting of hydrogen and C 1-6 alkyl;

iii) R 2 is phenyl, pyridyl, pyrimidyl, imidazolyl, pyrazolyl, imidazo[1,2-a]pyrimidine, imidazo[1,2-a]pyridine, or triazolo[4,3-a]pyridine, each of which is optionally substituted by one to three R 2d ; wherein R 2d is selected from the group consisting of hydrogen, halogen, —CN, —CH 3 , —CF 3 , —NH 2 , —S(O) 2 Me, —OCH 3 , COOH, CONH 2 , COOMe, —P(O)(CH 3 ) 2 , —CH 2 CH 2 OH, and —CH 2 CHF 2 ; or

iv) R 2 is phenyl or pyridyl, each of which is optionally substituted by one to three R 2d ; wherein R 2d is selected from the group consisting of hydrogen, halogen, —CN, —CH 3 , —CF 3 , —NH 2 , —S(O) 2 Me, —OCH 3 , COOH, CONH 2 , COOMe, —P(O)(CH 3 ) 2 , —CH 2 CH 2 OH, and —CH 2 CHF 2 .

11 . The compound of claim 10 or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein

i) R 7 and R 8 together with the N atom to which they are attached form 5-10 membered heterocyclyl or 5 membered heteroaryl, each of which is optionally substituted with one to three groups selected from halogen, —CN, oxo, —OH, C 1-6 alkyl, C 1-6 alkoxy, —C(O)R 7c , —C(O)OR 7c , and pyridinyl optionally substituted with CN;

R 7c is independently selected from the group consisting of hydrogen, C 1-4 alkyl optionally substituted with —CN or —OH; or

ii) R 7 and R 8 are independently hydrogen or C 1-4 alkyl.

12 . The compound of claim 11 , or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein R 2 is selected from the group consisting of

wherein R 2d is selected from the group consisting of hydrogen, halogen, —CN, —CH 3 , —CF 3 , —NH 2 , —S(O) 2 Me, —OCH 3 , COOH, CONH 2 , COOMe, —P(O)(CH 3 ) 2 , —CH 2 CH 2 OH, and —CH 2 CHF 2 .

13 . The compound of claim 12 or a pharmaceutically acceptable salt or a stereoisomer thereof, wherein R 7 and R 8 together with the atom to which they are attached form a heterocyclyl selected from the group consisting of

each of which is optionally substituted with one to three groups selected from —F, —CN, oxo, —OH, methyl, isopropyl, methoxy, —C(O)R 7c , —C(O)OR 7c , and pyridinyl optionally substituted with CN.

14 . A compound selected from the group consisting of

ID

Structure

Example 1

Example 2

Example 3

Example 4

Example 5

Example 6

Example 7

Example 8

Example 9

Example 10

Example 11

Example 12

Example 13

Example 14

Example 15

Example 16

Example 17

Example 18

Example 19

Example 20

Example 21

Example 22

Example 23

Example 24

Example 25

Example 26

Example 27

Example 28

Example 29

Example 30

Example 31

Example 32

Example 33

Example 34

Example 35

Example 36

Example 37

Example 38

Example 39

Example 40

Example 41

Example 42

Example 43

Example 44

Example 45

Example 46

Example 47

Example 48

Example 49

Example 50

Example 51

Example 52

Example 53

Example 54

Example 55

Example 56

Example 57

Example 58

Example 59

Example 60

Example 61

Example 62

Example 63

Example 64

Example 65

Example 66

Example 67

Example 68

Example 69

Example 70

Example 71

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Example 73

Example 74

Example 75

Example 76

Example 77

Example 78

Example 79

Example 80

Example 81

Example 82

Example 83

Example 84

Example 85

Example 86

Example 87

or a pharmaceutically acceptable salt or a stereoisomer thereof.

15 . A pharmaceutical composition comprising the compound of claim 1 , or a pharmaceutically acceptable salt or a stereoisomer thereof, and a pharmaceutically acceptable carrier or excipient.

16 . A method of treating a subject with a disease and/or a condition wherein the inhibition of the interaction of SOS1 and a RAS-family protein or RAC1 is of therapeutic benefit comprising administering to the subject a therapeutically effective amount of the compound of claim 1 or a pharmaceutically acceptable salt or a stereoisomer thereof.

17 . A method of treating a subject with cancer comprising administering to the subject a therapeutically effective amount of the compound of claim 1 or a pharmaceutically acceptable salt or a stereoisomer thereof; wherein the cancer selected from the group consisting of pancreatic cancer, lung cancer, colorectal cancer, cholangiocarcinoma, multiple myeloma, melanoma, uterine cancer, endometrial cancer, thyroid cancer, acute myeloid leukaemia, bladder cancer, urothelial cancer, gastric cancer, cervical cancer, head and neck squamous cell carcinoma, diffuse large B cell lymphoma, oesophageal cancer, chronic lymphocytic leukemia, hepatocellular cancer, breast cancer, ovarian cancer, prostate cancer, glioblastoma, renal cancer and sarcoma.

18 . The method of claim 17 , wherein the compound or a pharmaceutically acceptable salt or a stereoisomer thereof is administered in combination with a therapeutically effective amount of at least one other pharmacologically active substance.

19 . The method of claim 18 , wherein the at least one other pharmacologically active substance is an inhibitor of MEK and/or of mutants thereof.

20 . A compound, a pharmaceutically acceptable salt, or a stereoisomer thereof, wherein the compound is