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

IP.com Disclosure Number: IPCOM000211475D
Publication Date: 2011-Oct-06
Document File: 7 page(s) / 133K

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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:

, 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.


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Figure 1: an X-ray powder diffraction pattern of crystalline form 8 of Compound I.


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Figure 2: an X-ray powder diffraction pattern of crystalline form 9 of Compound I.

Pos. [°2Th.] Height [cts] d-spacing


[A]

7.21 276.82 12.26 1.2


8.40 920.56 10.52 4.1


9.17 981.71 9.65 4.3


11.40 963.99 7.77 4.3


11.73 1593.14 7.54 7.0


12.04 4020.53 7.35 17.8


12.30 3499.41 7.20 15.5


12.78 3440.92 6.93 15.2


14.21 164.22 6.23 0.7


15.18 529.54 5.84 2.3


15.53 967.35 5.70 4.3


17.05 22639.57 5.20 100.0


18.70 2820.51 4.75 12.5


19.26 4427.30 4.61 19.6


20.02 2679.54 4.43 11.8


20.83 3126.58 4.26 13.8


22.65 10998.87 3.93 48.6


23.01 22628.52 3.87 100.0


23.63 3841.69 3.77 17.0


24.29 2062.92 3.66 9.1

Rel. Int. [%]


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24.79 1427.34 3.59 6.3


26.04 2539.69 3.42 11.2


27.57 4506.11 3.24 19.9


28.48 1100.27 3.13 4.9


29.52 1861.09 3.03 8.2


30.28 807.38 2.95 3.6


30.61 777.88 2.92 3.4


31.39 420.80 2.85 1.9


33.32 785.20 2.69 3.5


34.25 599.14 2.62 2.7


35.85 258.93 2.51 1.1


36.70 249.84 2.45 1.1


37.49 311.42 2.40 1.4


39.22 898.74 2.30 4.0


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Figure 3: an X-ray powder diffraction pattern of crystalline form 10 of Compound I.


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Examples XRD

    XRPD peaks referred to throughout and in the examples 1 and 3. were obtained using an ARL X-ray powder diffractometer model X`TRA-030. equipped with Cu irradiation source =1.54056 Ǻ. 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 is defined as +/- 0.2 degrees due to experimental differences like instrumentations. sample preparations etc.

Example 1: Preparation of crystalline form 8 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 a...