IP Library › Granted Patent US 8,399,468
Granted Patent B2
US 8,399,468 · App. 12/715,660 · Granted Mar 19, 2013

Octahydro-pyrrolo[3,4-B]pyrrole derivatives

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Quick Facts
Patent No.
US 8,399,468
App. No.
12/715,660
Granted
Mar 19, 2013
Kind
B2
Abstract

Octahydro-pyrrolo[3,4-b]pyrrole derivatives are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Octahydro-pyrrolo[3,4-b]pyrrole compounds, methods for using such compounds, compositions for making them, and processes for preparing such compounds are disclosed herein.

Claims (14)

1. Crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one L-tartrate monohydrate Form A demonstrating at least one characteristic peak in the powder X-ray diffraction pattern at values of two theta of 3.90±0.2, 16.72±0.2, 16.99±0.2, 17.17±0.2, 18.12±0.2, 19.72±0.2, 19.98±0.2, 20.25±0.2, 23.96±0.2, 27.65±0.2, and 28.93±0.2.

2. Crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one L-tartrate monohydrate Form B demonstrating at least one characteristic peak in the powder X-ray diffraction pattern at values of two theta of 4.39±0.2, 10.45±0.2, 11.92±0.2, 12.52±0.2, 13.45±0.2, 16.71±0.2, 16.92±0.2, 17.62±0.2, 7.90±0.2, 19.10±0.2, 20.46±0.2, and 20.63±0.2.

3. Crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one hydrochloride trihemihydrate demonstrating at least one characteristic peak in the powder X-ray diffraction pattern at values of two theta of 4.03±0.2, 13.92±0.2, 15.55±0.2, 15.61±0.2, 15.93±0.2, 16.15±0.2, 24.37±0.2, 24.66±0.2, 25.12±0.2, 25.68±0.2, and 27.90±0.2.

4. Crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one L-tartrate anhydrate demonstrating at least one characteristic peak in the powder X-ray diffraction pattern at values of two theta of 4.34±0.2, 8.69±0.2, 13.04±0.2, 15.82±0.2, 1 7.11±0.2, 18.35±0.2, 18.93±0.2, 20.74±0.2, 22.40±0.2, 23.04±0.2, and 26.45±0.2.

5. Crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one hydrochloride anhydrate demonstrating at least one characteristic peak in the powder X-ray diffraction pattern at values of two theta of 6.27±0.2, 12.59±0.2, 15.15±0.2, 16.71±0.2, 18.49±0.2, 18.95±0.2, 20.31±0.2, 20.97±0.2, 22.44±0.2, 23.82±0.2, 24.03±0.2, 24.67±0.2, 31.90±0.2, and 32.75±0.2.

6. Substantially pure crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one L-tartrate monohydrate Form A.

7. Substantially pure crystalline 2-{4′-[(3aR,6aR)-5-methylhexylhydropyrrolo[3,4-b]pyrrol-1(2)-yl]-1,1′-biphenyl-4-yl}pyridazin 3(2H)-one L-tartrate monohydrate Form B.

8. Substantially pure crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one hydrochloride trihemihydrate.

9. Substantially pure crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-L-tartrate anhydrate.

10. Substantially pure crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1-biphenyl-4-yl}pyridazin-3(2H)-one hydrochloride anhydrate.

11. Crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one L-tartrate monohydrate Form A having the unit cell parameters wherein a is 7.6 Å, b is 7.4 Å, c is 22.7 Å and β is 94.1°.

12. Crystalline 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2)-one L-tartrate monohydrate Form B having the unit cell parameters wherein a is 7.6 Å, b is 8.7 Å, c is 40.3 Å.

13. Crystalline 2-{4-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one hydrochloride trihemihydrate having the unit cell parameters wherein a is 7.3 Å, b is 7.4 Å, c is 22.2 Å and α, β, γ are each respectively 86.3°, 81.0°, and 77.3°.

14. A process for preparing 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1′-biphenyl-4-yl}pyridazin-3(2H)-one comprising recrystallizing 2-{4′-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1-biphenyl-4-yl}pyridazin-3(2H)-one L-tartrate salt in water and dimethyl acetamide or ethanol.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2013
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 030231/0808 →