US 12,071,427 B2
Cereblon binding compounds, compositions thereof, and methods of treatment therewith
Matthew D. Alexander, San Diego, CA (US); Matthew D. Correa, San Diego, CA (US); Deepak Dalvie, Carlsbad, CA (US); Virginia Heather Sharron Grant, San Diego, CA (US); Joshua Hansen, La Jolla, CA (US); Roy L. Harris, III, San Diego, CA (US); Evan J. Horn, San Diego, CA (US); Dehua Huang, San Diego, CA (US); Christopher Mayne, Boulder, CO (US); Stephen Norris, San Diego, CA (US); Veronique Plantevin-Krenitsky, San Francisco, CA (US); John J. Sapienza, Chula Vista, CA (US); Lida Tehrani, San Diego, CA (US); and Brandon W. Whitefield, San Diego, CA (US)
Assigned to Celgene Corporation, Summit, NJ (US)
Filed by Celgene Corporation, Summit, NJ (US)
Filed on Mar. 16, 2023, as Appl. No. 18/122,496.
Application 18/122,496 is a continuation of application No. 17/356,370, filed on Jun. 23, 2021, granted, now 11,634,407.
Claims priority of provisional application 63/043,555, filed on Jun. 24, 2020.
Prior Publication US 2023/0242509 A1, Aug. 3, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/14 (2006.01); A61P 35/00 (2006.01)
CPC C07D 401/14 (2013.01) [A61P 35/00 (2018.01)] 15 Claims
 
1. A compound of formula I

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, tautomer, isotopolog, or stereoisomer thereof, wherein
RN is H;
n is 0-4;
each R1 is independently selected from halogen, CN, and C1-3 alkyl;
a is 1 or 2;
R2 and R3 are each independently selected from H, and C1-3 alkyl, or R2 and R3 and the carbon to which they are attached form a substituted or unsubstituted C3-6 cycloalkyl;
m is 0-8;
each R4 is independently substituted or unsubstituted C1-3 alkyl, or two R4 groups, together with the same carbon atom or adjacent carbon atoms to which they are attached, form a substituted or unsubstituted C3-6 cycloalkyl, or two R4 groups together with the non-adjacent carbon atoms to which they are attached form a substituted or unsubstituted 4-7-membered heterocyclyl;
X is N or CRX;
RX is hydrogen, halogen, —O(C1-6 alkyl) or —(C1-9 alkyl);
L is substituted or unsubstituted —O(C1-6 alkyl)-, —(C1-6 alkyl)O—, —O(C1-6 alkyl)O—, or —(C1-9 alkyl) -;
V is

OG Complex Work Unit Chemistry
wherein
B is N, CH, or CRB,
each RB is independently selected from halogen, and substituted or unsubstituted C1-6 alkyl;
RC is halogen, CF3 or SF5;
R5 and R6 are C1-3 alkyl, or R5 and R6, together with the carbon atom to which they are attached, form a substituted or unsubstituted C3-6 cycloalkyl or a 3-6 membered heterocyclyl; and
b is 0-2.