US 11,672,782 B2
Carboxamide derivatives
Kamlesh Jagdis Bala, Horsham (GB); Andrew Brearley, Oxfordshire (GB); James Dale, New Market (GB); Anne-Marie Edwards, Surrey (GB); Mahbub Ahmed, Horsham (GB); David Porter, Horsham (GB); Robert Alexander Pulz, Basel (CH); Lisa Ann Rooney, Surrey (GB); David Andrew Sandham, Horsham (GB); Duncan Shaw, Sharon, MA (US); Nichola Smith, Horsham (GB); Jessica Louise Taylor, Surrey (GB); Roger John Taylor, Southwater (GB); Thomas Josef Troxler, Wahlen b. Laufen (CH); and Joe Wrigglesworth, Nottingham (GB)
Assigned to NOVARTIS AG, Basel (CH)
Filed by Novartis AG, Basel (CH)
Filed on Nov. 4, 2020, as Appl. No. 17/89,064.
Application 17/089,064 is a continuation of application No. 16/874,595, filed on May 14, 2020, abandoned.
Application 16/874,595 is a continuation of application No. 16/230,033, filed on Dec. 21, 2018, abandoned.
Application 16/230,033 is a continuation of application No. 15/184,730, filed on Jun. 16, 2016, granted, now 10,195,181.
Application 15/184,730 is a continuation of application No. 14/711,684, filed on May 13, 2015, granted, now 9,403,810.
Claims priority of application No. 14168303 (EP), filed on May 14, 2014.
Prior Publication US 2021/0052554 A1, Feb. 25, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/422 (2006.01); A61K 31/4155 (2006.01); C07D 413/12 (2006.01); C07D 413/14 (2006.01)
CPC A61K 31/422 (2013.01) [A61K 31/4155 (2013.01); C07D 413/12 (2013.01); C07D 413/14 (2013.01)] 15 Claims
 
1. A method of treating a disorder or disease in a subject, wherein the subject has the disorder or disease, wherein the disease or disorder is selected from Pulmonary Hypertension, Fibrosis, Rheumatoid Arthritis, and Fracture healing, the method comprising administering to the subject a therapeutically effective amount of a compound of formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein
R1 is (C3-C6)alkyl or (C3-C6)cycloalkyl;
R2 is methyl;
R3 is selected from (C6-C10)branched alkyl, (C6-C10)branched alkenyl, (C5-C8)cycloalkenyl, (C5-C8)cycloalkyl, or Het; wherein the (C5-C8)cycloalkenyl or (C5-C8)cycloalkyl is unsubstituted or is substituted by one, two, three or four substituents R4; and wherein Het is substituted by one, two, three or four substituents R4;
each R4 is independently selected from halo, (C1-C4)alkyl, halo(C1-C4)alkyl, (C1-C4)alkoxy, or halo(C1-C4)alkoxy; or
two R4 groups, when attached to the same carbon atom, may be taken together with the carbon atom to which they are attached to form a cyclopentyl, tetrahydrofuran or dioxolane ring; wherein Het is a 5 or 6 membered fully saturated or partially saturated heterocyclic ring comprising a) 1 oxygen atom in the 2- or 3-position, or b) 2 oxygen atoms in the 2- and 5-, or 2- and 6-positions, wherein the numbering is relative to the point of attachment; and
(C5-C8)cycloalkyl may be a monocyclic ring or a bridged ring system containing 5, 6, 7 or 8 carbon atoms.