IP Library Granted Patent US 11,673,872
Granted Patent B2
US 11,673,872 · App. 17/946,112 · Granted Jun 13, 2023

Certain (2S)-N-[(1S)-1-cyano-2-phenylethyl]-1,4-oxazepane-2-carboxamides as dipeptidyl peptidase 1 inhibitors

Inventors: 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); Nicholas John Palmer (Cheshire, GB)
Assignee: AstraZeneca AB
C07D267/10A61K31/553A61K45/06C07D413/12C07D413/14C07D417/12
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Quick Facts
Patent No.
US 11,673,872
App. No.
17/946,112
Granted
Jun 13, 2023
Kind
B2
Abstract

The present disclosure relates to certain (2S)—N-[(1S)-1-cyano-2-phenylethyl]-1,4-oxazepane-2-carboxamide compounds (including pharmaceutically acceptable salts thereof), that inhibit dipeptidyl peptidase 1 (DPP1) activity, to their utility in treating and/or preventing clinical conditions including respiratory diseases, such as asthma and chronic obstructive pulmonary disease (COPD), to their use in therapy, to pharmaceutical compositions containing them and to processes for preparing such compounds.

Claims (15)

1. Crystal form C of (2S)—N-{(1S)-1-cyano-2-[4-(3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl)phenyl]ethyl}-1,4-oxazepane-2-carboxamide:

having X-ray powder diffraction peaks (° 2Θ) at 9.0±0.1, 14.0±0.1, 16.0±0.1, 16.4±0.1 and 21.0±0.1.

2. The crystal form C of (2S)—N-{(1S)-1-cyano-2-[4-(3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl)phenyl]ethyl}-1,4-oxazepane-2-carboxamide of claim 1 , having X-ray powder diffraction peaks (° 2Θ) at 7.8±0.1, 14.4±0.1, 17.9±0.1, 18.9±0.1 and 19.6±0.1.

3. A pharmaceutical composition comprising the crystal form C of (2S)—N-{(1S)-1-cyano-2-[4-(3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl)phenyl]ethyl}-1,4-oxazepane-2-carboxamide of claim 1 , and a pharmaceutically acceptable adjuvant, diluent or carrier.

4. A pharmaceutical composition comprising the crystal form C of (2S)—N-{(1S)-1-cyano-2-[4-(3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl)phenyl]ethyl}-1,4-oxazepane-2-carboxamide of claim 2 , and a pharmaceutically acceptable adjuvant, diluent or carrier.

5. A method for treating an obstructive disease of the airway, comprising orally administering to a patient in need thereof, the pharmaceutical composition of claim 3 .

6. A method for treating an obstructive disease of the airway, comprising orally administering to a patient in need thereof, the pharmaceutical composition of claim 4 .

7. The method of claim 5 , wherein the obstructive disease of the airway is bronchiectasis.

8. The method of claim 5 , wherein the obstructive disease of the airway is cystic fibrosis.

9. The method of claim 5 , wherein the obstructive disease of the airway is asthma.

10. The method of claim 5 , wherein the obstructive disease of the airway is chronic obstructive pulmonary disease (COPD).

11. The method of claim 6 , wherein the obstructive disease of the airway is bronchiectasis.

12. The method of claim 6 , wherein the obstructive disease of the airway is cystic fibrosis.

13. The method of claim 6 , wherein the obstructive disease of the airway is asthma.

14. The method of claim 6 , wherein the obstructive disease of the airway is chronic obstructive pulmonary disease (COPD).

Assignments (7)
PATENT SECURITY AGREEMENT Recorded Oct 20, 2022
From: INSMED INCORPORATED
To: BIOPHARMA CREDIT PLC
Reel/Frame 061735/0875 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Oct 19, 2022
From: INSMED INCORPORATED
To: ORBIMED ROYALTY & CREDIT OPPORTUNITIES IV, LP
Reel/Frame 061727/0039 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2022
From: CONNOLLY, STEPHEN; SWALLOW, STEVEN
To: ASTRAZENECA UK LIMITED
Reel/Frame 061379/0027 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2022
From: DOYLE, KEVIN; VAN DE POËL, AMANDA; JONES, GRAHAM; WATSON, DAVID; MACRITCHIE, JACQUELINE; PALMER, NICHOLAS
To: BIOFOCUS DPI LTD
Reel/Frame 061378/0992 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2022
From: LÖNN, HANS ROLAND; PONTÉN, JOHN FRITIOF; AURELL, CARL-JOHAN; PO KARLSSON, STAFFAN
To: ASTRAZENECA AB
Reel/Frame 061379/0067 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2022
From: ASTRAZENECA UK LIMITED
To: ASTRAZENECA AB
Reel/Frame 061379/0055 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2022
From: BIOFOCUS DPI LTD
To: ASTRAZENECA AB
Reel/Frame 061379/0011 →
Continuity (8)
Continuation 17170641 · Feb 8, 2021
Continuation 16855522 · Apr 22, 2020
Continuation 16358091 · Mar 19, 2019
Continuation 15708634 · Sep 19, 2017
Continuation 15346411 · Nov 8, 2016
Continuation 14601371 · Jan 21, 2015
Provisional Application 61931090 · Jan 24, 2014
Related Publication 20230115170A1 · Apr 13, 2023
Cited By (3)
US 12,201,638 US 12,479,837 US 12,679,815