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Process for the preparation of 2-((1-benzylpiperidin-4-yl)methyl-5,6-dimethoxy-2,3- dihydroinden-1-one hydrochloride

IP.com Disclosure Number: IPCOM000204399D
Publication Date: 2011-Feb-23
Document File: 7 page(s) / 129K

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The IP.com Prior Art Database

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Process for the preparation of 2-((1-benzylpiperidin-4-yl)methyl-5,6-dimethoxy-2,3- dihydroinden-1-one hydrochloride

2-isonicotinoyl-5,6-dimethoxy-2,3-dihydroinden-1-one of the following structure:

and 5,6-dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydroinden-1-one hydrochloride of the following structure:

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are intermediates in the synthesis of 2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3- dihydroinden-1-one hydrochloride (referred to herein as DNP HCl) of the following structure:

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DNP HCl is an acetylcholinesterase inhibitor used in the treatment of Alzheimer's disease. Described herein below are crystalline forms of INMH and INMH salts.

Crystalline 2-isonicotinoyl-5,6-dimethoxy-2,3-dihydroinden-1-one form I

    The crystalline form can be characterized by data selected from: X-ray powder diffraction having peaks at 6.6, 7.6, 9.5, 13.1, 13.7, 15.2, 16.9, 20.9, 24.0 and 26.0 degrees two theta ± 0.2 degrees two theta; an X-ray powder diffraction pattern as substantially depicted in Figure 1; and combination thereof.

1


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Figure 1: PXRD of crystalline 2-isonicotinoyl-5,6-dimethoxy-2,3-dihydroinden-1-one form I

Intensity (counts)

10000

8000

6000

4000

2000

0

5 10 15 20 25 30 35

2Theta (°)

Crystalline 2-isonicotinoyl-5,6-dimethoxy-2,3-dihydroinden-1-one form II

The crystalline form can be characterized by data selected from: X-ray powder diffraction having peaks at 7.9, 11.0, 12.7, 15.7, 16.5, 18.0, 20.4, 22.0, 23.7 and 25.0 degrees two theta ± 0.2 degrees two theta; an X-ray powder diffraction pattern as substantially depicted in Figure 2; and combination thereof.

Figure 2: PXRD of crystalline 2-isonicotinoyl-5,6-dimethoxy-2,3-dihydroinden-1-one form II

Intensity (counts)

60000

40000

20000

0

5 10 15 20 25 30 35

2Theta (°)

2


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Crystalline 2-isonicotinoyl-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride

    The crystalline form can be characterized by data selected from: X-ray powder diffraction having peaks at 11.8, 14.7, 16.0, 16.7, 18.3, 21.6, 23.5, 24.1, 26...

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