IP Library Granted Patent US 9,920,045
Granted Patent B2
US 9,920,045 · App. 15/344,372 · Granted Mar 20, 2018

Solid state forms of a PDE10 inhibitor

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Quick Facts
Patent No.
US 9,920,045
App. No.
15/344,372
Granted
Mar 20, 2018
Kind
B2
Abstract

The invention relates to a novel variable hydrate crystalline form of 1-(5-(4-chloro-3,5-dimethoxyphenyl)furan-2-yl)-2-ethoxy-2-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethanone, methods for the preparation thereof, pharmaceutical compositions thereof and their use in the inhibition of PDE10.

Claims (21)

1. A crystalline hydrate of Compound (I)

having a primitive monoclinic lattice Bravais type.

2. The crystalline hydrate of Compound (I) according to claim 1 wherein the primitive monoclinic lattice comprises vectors wherein a is about 8.655 Å, α is about 90°, b is about 17.893 Å, β is about 102.67°, c is about 16.315 Å, and γ is about 90°.

3. The crystalline hydrate of Compound (I) according to claim 1 having a space group of P2 1 /c.

4. A crystalline hydrate of Compound (I)

having an X-ray powder diffraction pattern comprising peaks at 9.9, 12.2, and 14.9 degrees 2θ (±0.2 degrees 2θ) when measured using CuKα radiation.

5. The crystalline hydrate of Compound (I) according to claim 4 having an X-ray powder diffraction pattern further comprising peaks at 10.4, 19.5, 20.1, 22.5, 22.9, and 25.8 degrees 2θ (±0.2 degrees 2θ) when measured using CuKα radiation.

6. The crystalline hydrate of Compound (I) according to claim 4 having an X-ray powder diffraction pattern substantially the same as that shown in FIG. 24 .

7. The crystalline hydrate of Compound (I) according to claim 4 having a DSC thermogram substantially the same as that shown in FIG. 5 .

8. The crystalline hydrate of Compound (I) according to claim 4 having a TGA curve substantially the same as that shown in FIG. 6 .

9. The crystalline hydrate of Compound (I) according to claim 4 having a dynamic vapor sorption isotherm substantially the same as that shown in FIG. 7 .

10. A crystalline hydrate of Compound (I)

having an X-ray powder diffraction pattern substantially the same as shifted Form F in FIG. 1 .

11. The crystalline hydrate of Compound (I) according to claim 10 having a dynamic vapor sorption isotherm substantially the same as that shown in FIG. 9 .

12. The crystalline hydrate of Compound (I) according to claim 10 having a DSC thermogram substantially the same as that shown in FIG. 10 .

13. The crystalline hydrate of Compound (I) according to claim 10 having a TGA curve substantially the same as that shown in FIG. 11 .

14. A pharmaceutical composition comprising a crystalline hydrate according to any one of claim 1 , 4 , or 10 , and at least one pharmaceutically acceptable carrier or diluent.

15. A method for inhibiting PDE10 in a warm-blooded animal, comprising administering to the animal an effective amount of a pharmaceutical composition according to claim 14 .

16. A method for treating a neurological disorder in a warm-blooded animal having said neurological disorder, comprising administering to the animal an effective amount of pharmaceutical composition according to claim 14 , wherein the neurological disorder is selected from the group consisting of psychotic disorders, anxiety disorders, Parkinson's disease, Huntington's disease, Alzheimer's disease, encephalitis, phobias, epilepsy, aphasia, Bell's palsy, cerebral palsy, sleep disorders, pain, Tourette's syndrome, schizophrenia, delusional disorders, bipolar disorders, post-traumatic stress disorders, drug-induced psychosis, panic disorders, obsessive-compulsive disorders, attention-deficit disorders, disruptive behavior disorders, autism, depression, dementia, epilepsy, insomnias and multiple sclerosis.

17. The method of claim 16 wherein the neurological disorder is schizophrenia.

18. The method of claim 16 wherein the neurological disorder is Huntington's disease.

Assignments (8)
RELEASE OF SECURITY INTEREST Recorded Nov 25, 2025
From: WILMINGTON SAVINGS FUND SOCIETY, FSB
To: OMEROS CORPORATION
Reel/Frame 073705/0970 →
CORRECTIVE ASSIGNMENT TO CORRECT THE CORRECT THE BOX TITLED"THIS DOCUMENT SERVES AS AN OATH/DECLARATION (37 CFR 1.63)" WAS ERRONEOUSLY CHECKED AND THIS BOX SHOULD NOT HAVE BEEN CHECKED, PREVIOUSLY RECORDED AT REEL: 67607 FRAME: 108. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST. Recorded Dec 11, 2024
From: OMEROS CORPORATION
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS COLLATERAL AGENT
Reel/Frame 069715/0719 →
SECURITY INTEREST Recorded Jun 3, 2024
From: OMEROS CORPORATION
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS COLLATERAL AGENT
Reel/Frame 067607/0108 →
RELEASE OF SECURITY INTEREST Recorded Nov 15, 2018
From: CRG SERVICING LLC
To: OMEROS CORPORATION
Reel/Frame 047573/0577 →
SECURITY INTEREST Recorded Jul 3, 2018
From: OMEROS CORPORATION
To: CRG SERVICING LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 046491/0017 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 14, 2017
From: AMRI SSCI, LLC
To: OMEROS CORPORATION
Reel/Frame 041250/0793 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 14, 2017
From: ALBERT, EKATERINA; NELSON, JENNIFER LEIGH; SEADEEK, CHRISTOPHER SCOTT
To: AMRI SSCI, LLC
Reel/Frame 041250/0871 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 14, 2017
From: REINEKE, KARL; JONAS, MARCO; IYER, SUBA; SUN, XUFENG; CUTSHALL, NEIL S.; GAGE, JENNIFER LYNN; LITTLE, THOMAS L.; LUKE, WAYNE DOUGLAS; BROT, ELISABETH C. A.; MCDERMOTT, MICHAEL JAMES
To: OMEROS CORPORATION
Reel/Frame 041250/0839 →