(WO/2005/003144) PROCESS FOR PREPARING NON-HYGROSCOPIC AZITHROMYCIN DIHYDRATE
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| Latest bibliographic data on file with the International Bureau
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| Pub. No.: | WO/2005/003144 | International Application No.: | PCT/IN2004/000187 | |||
| Publication Date: | 13.01.2005 | International Filing Date: | 28.06.2004 | |||
| Chapter 2 Demand Filed: 27.01.2005 | ||||||
| IPC: | C07H 17/00 (2006.01), C07H 17/08 (2006.01) | |||||
| Applicants: | JUBILANT ORGANOSYS LIMITED [IN/IN]; 1-A, Sector 16A, Institutional Area, Noida 201 301, Uttar Pradesh (IN) (All Except US). BHADRAVATHI, Ravikumar [IN/IN]; (IN) (US Only). KULKARNI, Ashok, Kumar [IN/IN]; (IN) (US Only). | |||||
| Inventors: | BHADRAVATHI, Ravikumar; (IN). KULKARNI, Ashok, Kumar; (IN). | |||||
| Agent: | SUBRAMANIAM, Hariharan et al.; Subramaniam, Nataraj & Associates, E-556, Greater Kailash-II, New Delhi 110 048 (IN) . | |||||
| Priority Data: |
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| Title: | PROCESS FOR PREPARING NON-HYGROSCOPIC AZITHROMYCIN DIHYDRATE | |||||
| Abstract: | A direct, single step process for preparing a semi-synthetic antibiotic azithromycin dihydrate (non-hygroscopic) is provided, by in situ reductive N-methylation of azaerythromycin A and subsequent crystallization from a mixture of acetone and water, preferably together with a catalytical quantity of a base such as liquor ammonia, which comprises: a) reacting azaerythromycin A with formic acid and formaldehyde in an organic solvent medium, to form a reaction mass comprising N-methylated azaerythromycin A (i.e. azithromycin); b) adding aqueous alkali solution to the reaction mass to form an aqueous phase and an organic phase; c) (i) when the organic solvent medium is acetone, separating the aqueous phase from the acetone organic phase, and removing the aqueous phase; or (ii) when the organic solvent medium is a solvent other than acetone, separating the aqueous phase from the organic phase and removing the aqueous phase, optionally washing the separated organic phase with aqueous alkali solution, completely distilling off the solvent from the organic phase to leave a residue, and adding acetone to dissolve the residue and form an acetone organic phase; d) adding water, and optionally a base, to the acetone organic phase to form a mixture, and allowing crystals to form in the mixture; e) recovering the crystals from the mixture and optionally washing the crystals; f) drying the crystals to obtain non-hygroscopic azithromycin dihydrate, and the yield of the non-hygroscopic azithromycin dihydrate of a pharmaceutically acceptable quality is obtained in yields up to 78-82% w/w. | |||||
| Designated States: |
AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. African Regional Intellectual Property Org. (ARIPO) (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW) Eurasian Patent Organization (EAPO) (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM) European Patent Office (EPO) (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR) African Intellectual Property Organization (OAPI) (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). |
| Publication Language: | English (EN) |
| Filing Language: | English (EN) |
