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Details for Patent: 9,221,823

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Details for Patent: 9,221,823

Title:Crystal form of pyrrolidylthiocarbapenem derivative
Abstract: Novel crystals of a pyrrolidylthiocarbapenem derivative having excellent stability is provided. According to the present invention, a crystal of (+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3[[(3S,5S)-5-(sulfa- moylaminomethyl)pyrrolidin-3-yl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carb- oxylic acid having a diffraction pattern in powder X-ray diffraction having main peaks at diffraction angles (2.theta.) of about 6.62, 13.04, 15.44, 16.58, 17.64, 20.88, 23.26, 25.02 and 25.52 (degrees) are provided.
Inventor(s): Saitoh; Izumi (Amagasaki, JP), Takahira; Masayuki (Amagasaki, JP), Kawakita; Toshio (Amagasaki, JP), Yoshioka; Yasuyuki (Amagasaki, JP)
Assignee: SHIONOGI & CO., LTD. (Osaka-Shi, Osaka, JP)
Filing Date:Feb 21, 2014
Application Number:14/187,010
Claims:1. A crystal of a dihydrate of (+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3[[(3S,5S)-5-(sulfa- moylaminomethyl)pyrrolidin-3-yl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carb- oxylic acid having a powder X-ray diffraction pattern comprising peaks at diffraction angles (2.theta.) of about 6.62, 13.04, 15.44, 16.58, 17.64, 20.88, 23.26, 25.02 and 25.52 (degrees), wherein the powder X-ray diffraction pattern is obtainable using Cu K.alpha. ray, 1.54 Angstroms (monochromater), tube voltage 40 kV, and tube current 40 mA.

2. A method for producing a crystal according to claim 1, comprising the steps of: (A) dissolving (+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3[[(3S,5S)-5-(sulfa- moylaminomethyl)pyrrolidin-3-yl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carb- oxylic acid or a hydrate thereof in water; (B) depositing crystals from the aqueous solution obtained in step (A); (C) determining the powder X-ray diffraction pattern of the crystals deposited in step (B); and (D) selecting a crystal having a powder X-ray diffraction pattern comprising peaks at diffraction angles (2 .theta.)of about 6.62, 13.04, 15.44, 16.58, 17.64, 20.88, 23.26, 25.02 and 25.52 (degrees), wherein the powder X-ray diffraction pattern is obtainable using Cu K.alpha. ray, 1.54 Angstroms (monochromator), tube voltage 40 kV, and tube current 40 mA.

3. A method for producing a crystal of a dihydrate of (+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3[[(3S,5S)-5-(sulfa- moylaminomethyl)pyrrolidin-3-yl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carb- oxylic acid, said crystal having a powder X-ray diffraction pattern comprising peaks at diffraction angles (2.theta.) of about 6.62, 13.04, 15.44, 16.58, 17.64, 20.88, 23.26, 25.02 and 25.52 (degrees), wherein the powder X-ray diffraction pattern is obtainable using Cu K.alpha. ray, 1.54 Angstroms (monochromator), tube voltage 40 kV, and tube current 40 mA, said method comprising the steps of: (A) dissolving (+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3[[(3S,5S)-5-(sulfa- moylaminomethyl)pyrrolidin-3-yl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carb- oxylic acid or a hydrate thereof in water; (B) placing a seed crystal produced according to claim 2 or recited in claim 1 in the aqueous solution obtained in step (A); (C) depositing crystals from the seeded aqueous solution obtained in step (B); and (D) isolating the crystals formed in step (C).
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