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CRYSATLLINE FORMS OF 7-METHYL-4, 6, 6a, 7, 8, 9-HEXAHYDROINDOLO [4, 3-FG] QUINOLINE-9-CARBOXYLIC ACID

IP.com Disclosure Number: IPCOM000210683D
Publication Date: 2011-Sep-08

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CRYSATLLINE FORMS OF 7-METHYL-4, 6, 6a, 7, 8, 9-HEXAHYDRO- INDOLO [4, 3-FG] QUINOLINE-9-CARBOXYLIC ACID

7-Methyl- 4,6,6a,7,8,9- hexahydro- indolo [4,3-fg] quinoline- 9-carboxylic acid referred to as 'Compound I', of the following formula:

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,

is a precursor for (6aR)- 4,6,6a,7,8,9,10,10a- octahydroindolo [4,3-fg] quinoline.

Described hereinafter, are crystalline forms of Compound I.

1


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Figure 1: an X-ray powder diffraction pattern of crystalline form 1 of Compound I.

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Figure 2: an X-ray powder diffraction pattern of crystalline form 2 of Compound I.

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Figure 3: an X-ray powder diffraction pattern of crystalline form 3 of Compound I.

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Figure 4: an X-ray powder diffraction pattern of crystalline form 4 of Compound I.

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Figure 5: an X-ray powder diffraction pattern of crystalline form 5 of Compound I.

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Figure 6: an X-ray powder diffraction pattern of crystalline form 6 of Compound I.

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Figure 7: an X-ray powder diffraction pattern of crystalline form 7 of Compound I.

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Examples:

XRD:

XRPD peaks referred to throughout and in the examples below, were obtained using an ARL X-ray powder diffractometer model X`TRA-030, equipped with Cu irradiation source =1.54056 , Peltier detector, round standard aluminium sample holder with round zero background quartz plate was used. Scanning parameters: Range: 2-40 deg. two-theta , continuous Scan, Rate: 3 deg./min. The accuracy of peak positions was defined as ± 0.2 degrees due to experimental differences like instrumentations, sample preparations etc…

Example 1: Preparation of crystalline form 1 of Compound I

For the crystallization of 7-Methyl- 4,6,6a,7,8,9- hexahydro- indolo [4,3-fg] quinoline- 9-carboxylic acid aqueous solution of 7-Methyl- 4,6,6a,7,8,9- hexahydro- indolo [4,3-fg] quinoline- 9-carboxylic acid sodium salt was used.

It may contain iso-7-Methyl- 4,6,6a,7,8,9- hexahydro- indolo [4,3-fg] quinoline- 9- carboxylic acid sodium salt (isoLANa).

The concentration of isoLANa was set to ca. 1.5 - 2.0 g/l by diluting the solution wi...