US 9,809,582 B2
Aminoester derivatives
Elisabetta Armani, Parma (IT); Gabriele Amari, Parma (IT); Wesley Blackaby, Saffron Walden (GB); Herve Van De Poel, Saffron Walden (GB); Charles Baker-Glenn, Saffron Walden (GB); and Naimisha Trivedi, Saffron Walden (GB)
Assigned to CHIESI FARMACEUTICI S.p.A., Parma (IT)
Filed by CHIESI FARMACEUTICI S.p.A., Parma (IT)
Filed on May 6, 2016, as Appl. No. 15/148,225.
Claims priority of application No. 15166703 (EP), filed on May 7, 2015.
Prior Publication US 2016/0326147 A1, Nov. 10, 2016
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/4545 (2006.01); C07D 409/12 (2006.01); C07D 409/14 (2006.01); C07D 471/08 (2006.01); A61K 31/439 (2006.01); A61K 31/4436 (2006.01); A61K 31/4439 (2006.01); C07D 453/02 (2006.01)
CPC C07D 409/12 (2013.01) [A61K 31/439 (2013.01); A61K 31/4436 (2013.01); A61K 31/4439 (2013.01); A61K 31/4545 (2013.01); C07D 409/14 (2013.01); C07D 453/02 (2013.01); C07D 471/08 (2013.01)] 17 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Drawing
wherein:
each R1 is hydrogen halogen, (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4) haloalkyl, hydroxy, —SO2NR6R7, —CN, —NR8SO2R9, —NR6R7, —CONR6R7, or —NR8COR9, wherein said (C1-C4) alkyl is optionally substituted by one or more groups selected from the group consisting of (C3-C7) cycloalkyl, hydroxyl, and —NR6R7 and wherein said (C1-C4) alkoxy is optionally substituted by one or more halogens or (C3-C7) cycloalkyl groups, wherein
R6 is hydrogen or (C1-C6) alkyl;
R7 is hydrogen or (C1-C6) alkyl;
R8 is hydrogen or (C1-C6) alkyl;
R9 is hydrogen or (C1-C6) alkyl;
n is an integer of 1 to 3;
each R2 is hydrogen halogen, (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4)haloalkyl, hydroxy, —SO2NR10R11, —CN, or —NR12SO2R13, wherein said (C1-C4) alkyl and said (C1-C4) alkoxy are optionally substituted by one or more (C3-C7) cycloalkyl groups, wherein
R10 is hydrogen or (C1-C6) alkyl;
R11 is hydrogen or (C1-C6) alkyl;
R12 is hydrogen or (C1-C6) alkyl;
R13 is hydrogen or (C1-C6) alkyl;
m is an integer of 1 to 3;
R3 and R4 are different or the same and are independently:
H;
(C3-C7) cycloalkylcarbonyl;
(C1-C6) alkyl, optionally substituted by one or more substituents selected from the group consisting of (C1-C4 alkoxy), (C3-C7) cycloalkyl, and (C5-C7) cycloalkenyl;
(C1-C6) haloalkyl;
(C3-C7) cycloalkyl;
(C5-C7) cycloalkenyl;
(C2-C6) alkenyl; or
(C2-C6) alkynyl;
each R5, whenever present, is independently CN, NO2, CF3, or a halogen atom;
k is 0 or an integer of 1 to 3;
L1 is a bond
W1 is a heteroarylene group;
W2 is aryl or heteroaryl;
L2 is a group —(CH2)q— wherein q is an integer of 1 to 4;
L3 is a bond or a group —(CH2)s— wherein s is 1 or 2;
X is:

OG Complex Work Unit Drawing
wherein
R20 is H, OH, or (C1-C4) alkyl optionally substituted by one or more hydroxyl group;
R21 is hydrogen or (C1-C6) alkyl optionally substituted by hydroxyl;
i is 1 or 2;
i′ is 1 or 2;
i″ is an integer of 1 to 4;
A is:
a group (CH2)s—NR16R17 wherein s is an integer of 1 to 4 and R16 and R17 are independently hydrogen or (C1-C4) alkyl; or
a saturated monocyclic, bicyclic, or tricyclic heterocyclic ring system containing one N heteroatom or NR18 wherein R18 is (C1-C4) alkyl or benzyl;
an N-oxide on the pyridine ring, a deuterated derivative, or a pharmaceutically acceptable salt thereof.