	US 11,926,642 B2
	Compounds and methods for the treatment of COVID-19
Robert Steven Kania, Del Mar, CA (US); Padmavani Bezawada, Vernon Hills, IL (US); Emma Louise Hawking, Deal (GB); Rohit Jaini, Chicago, IL (US); Samir Kulkarni, East Lyme, CT (US); Matthew Nathan O'Brien Laramy, Evanston, IL (US); Jonathan Richard Lillis, Ramsgate (GB); Suman Luthra, Westford, MA (US); Dafydd Rhys Owen, Concord, MA (US); Klimentina Dimitrova Pencheva, Ramsgate (GB); Anil Mahadeo Rane, Mystic, CT (US); Matthew Forrest Sammons, Quincy, MA (US); Bradley Paul Sullivan, Gurnee, IL (US); Andrew John Thiel, Gurnee, IL (US); Martyn David Ticehurst, Wingham (GB); Jamison Bryce Tuttle, Marblehead, MA (US); and Robert Louis Hoffman, San Diego, CA (US)
Assigned to Pfizer inc., New York, NY (US)
Filed by Pfizer Inc., New York, NY (US)
Filed on Jul. 1, 2021, as Appl. No. 17/365,213.
Application 17/365,213 is a continuation of application No. 17/221,676, filed on Apr. 2, 2021, abandoned.
Claims priority of provisional application 63/163,635, filed on Mar. 19, 2021.
Claims priority of provisional application 63/114,289, filed on Nov. 16, 2020.
Claims priority of provisional application 63/073,145, filed on Sep. 1, 2020.
Claims priority of provisional application 63/065,658, filed on Aug. 14, 2020.
Claims priority of provisional application 63/061,628, filed on Aug. 5, 2020.
Claims priority of provisional application 63/038,454, filed on Jun. 12, 2020.
Claims priority of provisional application 63/005,407, filed on Apr. 5, 2020.
Prior Publication US 2022/0017548 A1, Jan. 20, 2022
Int. Cl. C07F 9/572 (2006.01); A61P 31/14 (2006.01)

CPC C07F 9/5728 (2013.01) [A61P 31/14 (2018.01); C07B 2200/13 (2013.01)]

19 Claims

1. Crystalline (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl dihydrogen phosphate hydrate having one or more characteristics selected from the group consisting of a powder X-ray diffraction pattern, a ¹³C solid state NMR spectrum and a Raman spectrum;

wherein the powder X-ray diffraction pattern characteristic is selected from

a) a powder X-ray diffraction pattern comprising peaks at 4.1±0.2 and 7.2±0.2 degrees 2-Theta;

b) a powder X-ray diffraction pattern comprising peaks at 4.1±0.2, 7.2±0.2 and 10.4±0.2 degrees 2-Theta; and

c) a powder X-ray diffraction pattern comprising peaks at 4.1±0.2, 7.2±0.2, 10.4±0.2 and 14.5±0.2 degrees 2-Theta;

wherein the ¹³C solid state NMR spectrum characteristic is selected from

a) ¹³C solid state NMR spectrum comprising peaks at 21.7, 153.8 and 172.2 ppm; each peak±0.2 ppm;

b) a ¹³C solid state NMR spectrum comprising peaks at 21.7, 153.8, 172.2 and 118.6 ppm; each peak±0.2 ppm; and

c) a ¹³C solid state NMR spectrum comprising peaks at 21.7, 153.8, 172.2, 118.6 and 57.8 ppm; each peak±0.2 ppm; and

wherein the Raman spectrum characteristic is selected from

a) a Raman spectrum comprising Raman peaks at 1271, 1421 and 1217 cm⁻¹, each peak±2 cm⁻¹,

b) a Raman spectrum comprising Raman peaks at 1271, 1421, 1217 and 1640 cm⁻¹; each peak±2 cm⁻¹and

c) a Raman spectrum comprising Raman peaks at 1271, 1421, 1217, 1640 and 3074 cm⁻¹; each peak±2 cm⁻¹.