US 11,667,615 B2
Certain (2S)-N-[(1S)-1-cyano-2-phenylethyl]-1,4-oxazepane-2-carboxamides as dipeptidyl peptidase 1 inhibitors
Hans Roland Lönn, Cheshire (GB); Stephen Connolly, Cheshire (GB); Steven Swallow, Cheshire (GB); Staffan Po Karlsson, Mölndal (SE); Carl-Johan Aurell, Mölndal (SE); John Fritiof Pontén, Cheshire (GB); Kevin James Doyle, Essex (GB); Amanda Jane Van De Poël, Essex (GB); Graham Peter Jones, Essex (GB); David Wyn Watson, Essex (GB); Jaqueline Anne Macritchie, Essex (GB); and Nicholas John Palmer, Cheshire (GB)
Assigned to AstraZeneca AB, Södertälje (SE)
Filed by AstraZeneca AB, Södertälje (SE)
Filed on Feb. 8, 2021, as Appl. No. 17/170,641.
Application 17/170,641 is a continuation of application No. 16/855,522, filed on Apr. 22, 2020, granted, now 11,117,874.
Application 16/855,522 is a continuation of application No. 16/358,091, filed on Mar. 19, 2019, granted, now 10,669,245, issued on Jun. 2, 2020.
Application 16/358,091 is a continuation of application No. 15/708,634, filed on Sep. 19, 2017, granted, now 10,287,258, issued on May 14, 2019.
Application 15/708,634 is a continuation of application No. 15/346,411, filed on Nov. 8, 2016, granted, now 9,815,805, issued on Nov. 14, 2017.
Application 15/346,411 is a continuation of application No. 14/601,371, filed on Jan. 21, 2015, granted, now 9,522,894, issued on Dec. 20, 2016.
Claims priority of provisional application 61/931,090, filed on Jan. 24, 2014.
Prior Publication US 2021/0238152 A1, Aug. 5, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 267/10 (2006.01); C07D 409/10 (2006.01); C07D 413/10 (2006.01); C07D 413/12 (2006.01); C07D 413/14 (2006.01); C07D 417/12 (2006.01); A61P 11/00 (2006.01); A61K 31/553 (2006.01); A61K 45/06 (2006.01)
CPC C07D 267/10 (2013.01) [A61K 31/553 (2013.01); A61K 45/06 (2013.01); C07D 413/12 (2013.01); C07D 413/14 (2013.01); C07D 417/12 (2013.01)] 15 Claims
 
1. A method for treating alpha-1 antitrypsin deficiency in a patient in need thereof, comprising, administering to the patient, an effective amount of a compound of formula (I)

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein,
R1 is

OG Complex Work Unit Chemistry
R2 is selected from hydrogen, F, Cl, Br, OSO2C1-3alkyl, or C1-3alkyl;
R3 is selected from hydrogen, F, Cl, Br, CN, CF3, SO2C1-3alkyl, CONH2 or SO2NR4R5, wherein R4 and R5 together with the nitrogen atom to which they are attached form an azetidine, pyrrolidine or piperidine ring; or
R1 is selected from

OG Complex Work Unit Chemistry
X is selected from O, S or CF2;
Y is selected from O or S;
Q is selected from CH or N;
R6 is selected from C1-3alkyl, wherein said C1-3alkyl is optionally substituted by 1, 2 or 3 F and optionally by one substituent selected from OH, OC1-3alkyl, N(C1-3alkyl)2, cyclopropyl, or tetrahydropyran; and
R7 is selected from hydrogen, F, Cl or CH3.