US 12,404,241 B2
Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewith
Massimo Ammirante, San Diego, CA (US); Sogole Bahmanyar, Rancho Santa Fe, CA (US); Matthew D. Correa, San Diego, CA (US); Virginia Heather Sharron Grant, San Diego, CA (US); Joshua Hansen, San Diego, CA (US); Evan J. Horn, San Diego, CA (US); Timothy S. Kercher, Longmont, CA (US); Christopher Mayne, San Diego, CA (US); Mark A. Nagy, San Diego, CA (US); Rama Krishna Narla, San Diego, CA (US); Surendra Nayak, San Diego, CA (US); Stephen Norris, San Diego, CA (US); Patrick Papa, San Diego, CA (US); Veronique Plantevin-Krenitsky, San Francisco, CA (US); John J. Sapienza, San Diego, CA (US); Brandon W. Whitefield, San Diego, CA (US); and Shuichan Xu, San Diego, CA (US)
Assigned to Celgene Corporation, Summit, NJ (US)
Filed by Celgene Corporation, Summit, NJ (US)
Filed on Nov. 28, 2023, as Appl. No. 18/521,663.
Application 17/403,742 is a division of application No. 16/719,171, filed on Dec. 18, 2019, granted, now 11,149,007, issued on Oct. 19, 2021.
Application 18/521,663 is a continuation of application No. 17/403,742, filed on Aug. 16, 2021, granted, now 11,873,283.
Claims priority of provisional application 62/879,900, filed on Jul. 29, 2019.
Claims priority of provisional application 62/782,298, filed on Dec. 19, 2018.
Prior Publication US 2024/0368083 A1, Nov. 7, 2024
Int. Cl. C07D 211/94 (2006.01); C07D 233/30 (2006.01)
CPC C07D 211/94 (2013.01) [C07D 233/30 (2013.01)] 16 Claims
 
1. A process of preparing a compound of formula (I)

OG Complex Work Unit Chemistry
wherein the process comprises contacting a compound of formula (i)

OG Complex Work Unit Chemistry
with a compound of formula (b)

OG Complex Work Unit Chemistry
wherein Hal2 is Br or Cl, in the presence of a base, in a solvent, under conditions suitable to provide a compound of formula (I); wherein
RN is H;
each R1 is independently selected from halogen, CN, and C1-3 alkyl;
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;
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;
L is —O(C1-6 alkyl)- or (C1-9 alkyl)-;
n is 0-4;
m is 0-8;
V is

OG Complex Work Unit Chemistry
wherein
A is N, CH, or CRA;
B is N, CH, or CRB,
each RA is independently selected from halogen, substituted or unsubstituted C1-6 alkyl, and substituted or unsubstituted C3-6 cycloalkyl;
each RB is independently selected from halogen, or substituted and unsubstituted C1-6 alkyl;
RC is halogen or CF3;
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;
a is 0-3; and
b is 0-2.