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Volumn 13, Issue 3, 2009, Pages 567-572

Manufacture of high-purity meloxicam via its novel potassium salt monohydrate

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EID: 66249088667     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900031h     Document Type: Article
Times cited : (35)

References (30)
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    • Coppi, L.; Sanmarti, M. B.; Montserrat, C. C. Crystalline forms of meloxicam. U.S. Pat. Appl. 2003/109701, 2003. Chem. Abstr. 2003, 139, 26613.
    • Coppi, L.; Sanmarti, M. B.; Montserrat, C. C. Crystalline forms of meloxicam. U.S. Pat. Appl. 2003/109701, 2003. Chem. Abstr. 2003, 139, 26613.
  • 11
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    • The basic patent of meloxicam is: Trummlitz, G, Engel, W, Seeger, E, Engelhardt, G. 4-Hydroxy-2H-1,2-benzothiazin-3-carboxamid- 1,1-dioxides. Ger. Pat. DE 2756113, 1979. Chem. Abstr. 1979, 91, 91656
    • (a) The basic patent of meloxicam is: Trummlitz, G.; Engel, W.; Seeger, E.; Engelhardt, G. 4-Hydroxy-2H-1,2-benzothiazin-3-carboxamid- 1,1-dioxides. Ger. Pat. DE 2756113, 1979. Chem. Abstr. 1979, 91, 91656.
  • 12
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    • The U.S. equivalent of the basic patent is: Trummlitz, G, Engel, W, Seeger, E, Engelhardt, G. U.S. Patent 4,233,299, 1980
    • The U.S. equivalent of the basic patent is: Trummlitz, G.; Engel, W.; Seeger, E.; Engelhardt, G. U.S. Patent 4,233,299, 1980.
  • 13
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    • The following paper applies the same starting materials (3, 4), but the amidation step is performed in the presence of BF3 catalyst and molecular sieves: Zia-ur-Rehman, M.; Choudary, J. A.; Ahmad, S. Bull. Korean Chem. Soc. 2005, 26, 1771-1775. Chem. Abstr 2006, 145, 83282.
    • The following paper applies the same starting materials (3, 4), but the amidation step is performed in the presence of BF3 catalyst and molecular sieves: Zia-ur-Rehman, M.; Choudary, J. A.; Ahmad, S. Bull. Korean Chem. Soc. 2005, 26, 1771-1775. Chem. Abstr 2006, 145, 83282.
  • 14
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    • A less common synthetic procedure, i.e. transamination of corresponding carboxamides with 5-methyl-1,3-thiazol-2-amine is also mentioned in the literature: see ref 8a example 10
    • A less common synthetic procedure, i.e. transamination of corresponding carboxamides with 5-methyl-1,3-thiazol-2-amine is also mentioned in the literature: see ref 8a example 10.
  • 15
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    • For the synthesis of starting materials 3a and 3b, see: (a) Lombardino, J. G.; Wiseman, E. H.; McLamore, W. M. J. Med. Chem. 1971, 14, 1171-1175.
    • For the synthesis of starting materials 3a and 3b, see: (a) Lombardino, J. G.; Wiseman, E. H.; McLamore, W. M. J. Med. Chem. 1971, 14, 1171-1175.
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    • Reference 9
    • Reference 9.
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    • For analogous thiazole N-alkylation leading to N-[3-alkyl-1,3-thiazol- 2(3H)-ylidene]-carboxamide derivatives with Z configuration, see: (a) Ohta, H.; Ishizaka, T.; Tatsuzuki, M.; Yoshinaga, M.; Iida, I.; Tomishima, Y.; Toda, Y.; Saito, S. Bioorg. Med. Chem. Lett. 2007, 17, 6299-6304.
    • For analogous thiazole N-alkylation leading to N-[3-alkyl-1,3-thiazol- 2(3H)-ylidene]-carboxamide derivatives with Z configuration, see: (a) Ohta, H.; Ishizaka, T.; Tatsuzuki, M.; Yoshinaga, M.; Iida, I.; Tomishima, Y.; Toda, Y.; Saito, S. Bioorg. Med. Chem. Lett. 2007, 17, 6299-6304.
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    • For papers discussing the simultaneous formation of products alkylated at the carboxamide nitrogen and the thiazole nitrogen atoms, see: (a) Hadida Ruah, S. S.; Grootenhuis, P. D. J.; Miller, M. T.; Hamilton, M. Preparation of mainly N-thiazolyl carboxamides as modulators of ATP-binding cassette transporters. PCT Pat. Appl. WO 2005/075435, 2005. Chem. Abstr. 2005, 143, 229835; example 28, (E)-(Z) isomerism not discussed.
    • For papers discussing the simultaneous formation of products alkylated at the carboxamide nitrogen and the thiazole nitrogen atoms, see: (a) Hadida Ruah, S. S.; Grootenhuis, P. D. J.; Miller, M. T.; Hamilton, M. Preparation of mainly N-thiazolyl carboxamides as modulators of ATP-binding cassette transporters. PCT Pat. Appl. WO 2005/075435, 2005. Chem. Abstr. 2005, 143, 229835; example 28, (E)-(Z) isomerism not discussed.
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    • European Pharmacopoeia (Ph. Eur.) Suppl. 6.3, 2009; 2373.
    • European Pharmacopoeia (Ph. Eur.) Suppl. 6.3, 2009; 2373.
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    • Process for the purification of meloxicam
    • Eur. Pat. EP 1645559, 350700
    • Vigano, E.; Landonio, E. Process for the purification of meloxicam. Eur. Pat. EP 1645559, 2006. Chem. Abstr. 2006, 144, 350700.
    • (2006) Chem. Abstr , vol.144
    • Vigano, E.1    Landonio, E.2
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    • Venkataraman, S.; Kumar, M. K.; Purandhar, K.; Reddy, B. K.; Reddy, L A.; Kondaiah, G. C.; Sreenath, K. Process for the preparation of crystalline form of meloxicam. U.S. Patent Appl. 2006/025408, 2006. Chem. Abstr. 2006, 144, 177433.
    • Venkataraman, S.; Kumar, M. K.; Purandhar, K.; Reddy, B. K.; Reddy, L A.; Kondaiah, G. C.; Sreenath, K. Process for the preparation of crystalline form of meloxicam. U.S. Patent Appl. 2006/025408, 2006. Chem. Abstr. 2006, 144, 177433.
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    • Trummlitz, G, Sieger, P, Werthmann, U, Soyka, R, Luger, P. Novel modification of 2H-1,2-benzothiazine-3-carboxamide-4-hydroxy- 2-methyl-N-(5-methyl-2-thiazolyl)-1,1-dioxide (meloxicam) in form of a crystalline acetic acid solvate and use as drug. Ger. Pat. Appl. DE 10245882, 2004. Chem. Abstr. 2004, 140, 390403
    • (a) Trummlitz, G.; Sieger, P.; Werthmann, U.; Soyka, R.; Luger, P. Novel modification of 2H-1,2-benzothiazine-3-carboxamide-4-hydroxy- 2-methyl-N-(5-methyl-2-thiazolyl)-1,1-dioxide (meloxicam) in form of a crystalline acetic acid solvate and use as drug. Ger. Pat. Appl. DE 10245882, 2004. Chem. Abstr. 2004, 140, 390403.
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    • The PCT equivalent of this German patent application is: Trummlitz, G, Sieger, P, Werthmann, U, Soyka, R, Luger, P. PCT Pat. Appl. WO 2004/031183, 2004
    • The PCT equivalent of this German patent application is: Trummlitz, G.; Sieger, P.; Werthmann, U.; Soyka, R.; Luger, P. PCT Pat. Appl. WO 2004/031183, 2004.
  • 28
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    • Mezei, T.; Simig, Gy.; Molna'r, E.; Luka'cs, Gy.; Porcs-Makkay, M.; Volk, B.; Hoffmanne' Fekete, V.; Nagy, K. Mesterha'zy, N.; Krasznai, Gy.; Vereczkeyne' Dona'th, Gy.; Körtve'lyessy, Gy.; Pe'csi, E' . Process for preparation of high-purity meloxicam and meloxicam potassium salt. PCT Pat. Appl. WO 2006/064298, 2006. Chem. Abstr. 2006, 145, 83359.
    • Mezei, T.; Simig, Gy.; Molna'r, E.; Luka'cs, Gy.; Porcs-Makkay, M.; Volk, B.; Hoffmanne' Fekete, V.; Nagy, K. Mesterha'zy, N.; Krasznai, Gy.; Vereczkeyne' Dona'th, Gy.; Körtve'lyessy, Gy.; Pe'csi, E' . Process for preparation of high-purity meloxicam and meloxicam potassium salt. PCT Pat. Appl. WO 2006/064298, 2006. Chem. Abstr. 2006, 145, 83359.


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