Isolation and Characterization of an Impurity Obtained During the Synthesis of the Antibiotic Drug Sparfloxacin

Nirmala MUNIGELA; Moses BABU J.; Anjaneyulu YERRAMILLI; Peddy VISHWESHWAR; Ganesh YADDANAPUDI SESHA SIVA YADDANAPUDI SESHA SIVA; Narayana Murthy VALAVALA

doi:10.3797/scipharm.0812-12

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Article

5 February 2009

Isolation and Characterization of an Impurity Obtained During the Synthesis of the Antibiotic Drug Sparfloxacin

and

Department of Analytical Research, Discovery Research, Dr. Reddy’s Laboratories, Miyapur, Hyderabad 500 049, India

Process R&D, Custom pharmaceutical synthesis-II, Dr. Reddy’s Laboratories Ltd., Jeedimetla, Hyderabad, India

Jawaharlal Nehru Technological University, Kukatpally, Hyderabad-500072, India

Author to whom correspondence should be addressed.

Sci. Pharm.2009, 77(1), 67-78;https://doi.org/10.3797/scipharm.0812-12

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Abstract

During the synthesis of Sparfloxacin, a fluoroquinolone antibiotic drug, an unknown impurity (SF5-IMP) was identified in the fifth stage of the synthetic process. The impurity has been isolated from the mother liquor of intermediate SF5. The mother liquor was concentrated to dryness added dichloromethane and stirred for 1 h and filtered to generate SF5-IMP and the molecular structure was elucidated as 7-amino-1-cyclopropyl-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline- 3-carboxylic acid by ¹⁹F NMR and single crystal X-ray diffraction studies. The structural features of SF5-IMP and SF5 have been discussed here.

Keywords:

Sparfloxacin; ¹H NMR; ¹⁹F NMR; Single crystal X-ray diffraction

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