IP Library Granted Patent US 10,532,047
Granted Patent B2
US 10,532,047 · App. 16/414,716 · Granted Jan 14, 2020

Solid forms of ((S)-5-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile

Inventor: George P. Luke (Clinton, CT)
Assignee: FORMA Therapeutics, Inc.
A61K31/4709A61K9/0053A61K47/12A61K47/38
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Quick Facts
Patent No.
US 10,532,047
App. No.
16/414,716
Granted
Jan 14, 2020
Kind
B2
Abstract

The present disclosure reports solid forms of ((S)-5-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile.

Claims (188)

1. A solid form of Compound 1:

characterized by an X-ray Powder Diffraction (XRPD) having diffractions at angles (2 theta±0.2) of 6.3, 12.8, 13.8, 23.6, and 27.8.

2. The solid form of claim 1 characterized by an X-ray Powder Diffraction (XRPD) having diffractions at angles (2 theta±0.2) of 6.3, 12.8, 13.8, 23.6, and 27.8, corresponding to d-spacing (angstroms±0.2) of 14.0, 6.9, 6.4, 3.8, and 3.2, respectively.

3. The solid form of claim 1 characterized by an X-ray Powder Diffraction (XRPD) having diffractions at angles (2 theta±0.2) of 5.7, 6.3, 8.5, 10.6, 12.8, 13.8, 17.3, 22.0, 22.8, 23.6, and 27.8.

4. The solid form of claim 1 characterized by an X-ray Powder Diffraction (XRPD) having diffractions at angles (2 theta±0.2) of 5.7, 6.3, 8.5, 10.6, 12.8, 13.8, 17.3, 22.0, 22.8, 23.6, and 27.8 corresponding to d-spacing (angstroms±0.2) of 15.4, 14.0, 10.4, 8.4, 6.9, 6.4, 5.1, 4.0, 3.9, 3.8, and 3.2, respectively.

5. The solid form of claim 1 characterized by an X-ray Powder Diffraction (XRPD) having peaks at the same or substantially the same angles (2θ±0.2) and corresponding d-spacing (ű0.2) of:

d-spacing

2θ ± 0.2

Å ± 0.2

5.7

15.4

6.3

14.0

8.5

10.4

10.6

8.4

11.4

7.8

12.8

6.9

13.8

6.4

14.2

6.2

15.2

5.8

15.6

5.7

17.3

5.1

17.9

5.0

18.2

4.9

18.9

4.7

19.6

4.5

20.6

4.3

21.5

4.1

22.0

4.0

22.8

3.9

23.6

3.8

24.5

3.6

24.8

3.6

25.3

3.5

25.6

3.5

26.0

3.4

26.3

3.4

27.0

3.3

27.8

3.2

28.9

3.1

30.0

3.0

31.2

3.0

32.1

2.8

33.6

2.7

34.1

2.6

36.3

2.5

37.0

2.4

38.1

2.4

6. The solid form of claim 1 characterized by a differential scanning calorimetry (DSC) thermogram with an endothermic event observed at about 256.6° C.

7. The solid form of claim 2 characterized by a differential scanning calorimetry (DSC) thermogram with an endothermic event observed at about 256.6° C.

8. The solid form of claim 1 characterized by a dynamic vapor sorption (DVS) showing maximum water uptake of 0.25% w/w at 25° C./90% RH.

9. The solid form of claim 6 characterized by a dynamic vapor sorption (DVS) showing maximum water uptake of 0.25% w/w at 25° C./90% RH.

10. A solid form of ((S)-5-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile, characterized by a DSC endothermic event at about 256.6° C., wherein the DSC is obtained by heating at 10° C./min from about 20° C. to about 300° C. using dry nitrogen to purge the system and the following parameters:

Parameters

DSC

Pan Type

Aluminum pan, closed

Temperature

RT-250° C.

Ramp rate

10° C./min

Purge gas

N 2

11. The solid form of claim 10 characterized by an X-ray Powder Diffraction (XRPD) having diffractions at angles (2 theta±0.2) of 6.3, 12.8, 13.8, 23.6, and 27.8.

12. The solid form of claim 10 characterized by a dynamic vapor sorption (DVS) showing maximum water uptake of 0.25% w/w at 25° C./90% RH.

13. The solid form of claim 11 characterized by a dynamic vapor sorption (DVS) showing maximum water uptake of 0.25% w/w at 25° C./90% RH.

14. A solid form of olutasidenib, characterized by at least one of the following characteristics:

(i) an X-ray Powder Diffraction (XRPD) having diffractions at angles (2 theta±0.2) of 6.3, 12.8, 13.8, 23.6, and 27.8;

(ii) a differential scanning calorimetry (DSC) thermogram with an endothermic event observed at about 256.6° C.; and

(iii) a dynamic vapor sorption (DVS) showing maximum water uptake of 0.25% w/w at 25° C./90% RH.

15. The solid form of claim 14 , characterized by an X-ray Powder Diffraction (XRPD) having diffractions at angles (2 theta±0.2) of 6.3, 12.8, 13.8, 23.6, and 27.8, corresponding to d-spacing (angstroms±0.2) of 14.0, 6.9, 6.4, 3.8, and 3.2, respectively.

16. The solid form of claim 15 , characterized by an X-ray Powder Diffraction (XRPD) having diffractions at angles (2 theta±0.2) of 5.7, 6.3, 8.5, 10.6, 12.8, 13.8, 17.3, 22.0, 22.8, 23.6, and 27.8.

17. The solid form of claim 16 , characterized by an X-ray Powder Diffraction (XRPD) having diffractions at angles (2 theta±0.2) of 5.7, 6.3, 8.5, 10.6, 12.8, 13.8, 17.3, 22.0, 22.8, 23.6, and 27.8 corresponding to d-spacing (angstroms±0.2) of 15.4, 14.0, 10.4, 8.4, 6.9, 6.4, 5.1, 4.0, 3.9, 3.8, and 3.2, respectively.

18. The solid form of claim 17 , characterized by an X-ray Powder Diffraction (XRPD) having peaks at the same or substantially the same angles (2θ±0.2) and corresponding d-spacing (ű0.2) of:

d-spacing

2θ ± 0.2

Å ± 0.2

5.7

15.4

6.3

14.0

8.5

10.4

10.6

8.4

11.4

7.8

12.8

6.9

13.8

6.4

14.2

6.2

15.2

5.8

15.6

5.7

17.3

5.1

17.9

5.0

18.2

4.9

18.9

4.7

19.6

4.5

20.6

4.3

21.5

4.1

22.0

4.0

22.8

3.9

23.6

3.8

24.5

3.6

24.8

3.6

25.3

3.5

25.6

3.5

26.0

3.4

26.3

3.4

27.0

3.3

27.8

3.2

28.9

3.1

30.0

3.0

31.2

3.0

32.1

2.8

33.6

2.7

34.1

2.6

36.3

2.5

37.0

2.4

38.1

2.4.

19. The solid form of claim 18 , characterized by a differential scanning calorimetry (DSC) thermogram with an endothermic event observed at about 256.6° C.

20. The solid form of claim 19 , characterized by a dynamic vapor sorption (DVS) showing maximum water uptake of 0.25% w/w at 25° C./90% RH.

Assignments (2)
SECURITY INTEREST Recorded May 8, 2026
From: RIGEL PHARMACEUTICALS, INC.
To: MIDCAP FUNDING IV TRUST
Reel/Frame 075576/0880 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 4, 2019
From: LUKE, GEORGE P.; SHETH, PRATIK
To: FORMA THERAPEUTICS, INC.
Reel/Frame 049366/0942 →
Continuity (4)
Provisional Application 62692591 · Jun 29, 2018
Provisional Application 62672462 · May 16, 2018
Provisional Application 62672461 · May 16, 2018
Related Publication 20190350920A1 · Nov 21, 2019