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(a) Hawkey, C.; Kahan, A.; Steinbrück, K.; Alegre, C.; Baumelou, E.; Begaud, B.; Dequeker, J.; Isomaki, H.; Littlejohn, G.; Mau, J.; Papazoglou, S. Brit. J. Rheumatol. 1998, 37, 937-945.
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Luger, P.; Daneck, K.; Engel, W.; Trummlitz, G.; Wagner, K. Eur. J. Pharm. Sci. 1996, 4, 175-187.
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66249140467
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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.
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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.
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11
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66249129938
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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
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(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.
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12
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66249140836
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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
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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.
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13
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31744434741
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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.
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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.
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14
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66249120918
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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
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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.
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15
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0015188042
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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.
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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.
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17
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0015621734
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Lombardino, J. G.; Wiseman, E. H.; Chianini, J. J. Med. Chem. 1973, 16, 493-496.
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J. Med. Chem
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Lombardino, J.G.1
Wiseman, E.H.2
Chianini, J.3
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18
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66249135876
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Reference 9
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Reference 9.
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19
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35048814909
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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.
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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.
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20
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11144347667
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Manaka, A.; Ishii, T.; Takahashi, K.; Sato, M. Tetrahedron Lett. 2005, 46, 419-422.
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Tetrahedron Lett
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Manaka, A.1
Ishii, T.2
Takahashi, K.3
Sato, M.4
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21
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66249106252
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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.
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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.
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22
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24744456662
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Masuda, N.; Yamamoto, O.; Fujii, M.; Ohgami, T.; Moritomo, A.; Kontani, T.; Kageyama, S.; Ohta, M. Synth. Commun. 2005, 35, 2305-2316.
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Synth. Commun
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Masuda, N.1
Yamamoto, O.2
Fujii, M.3
Ohgami, T.4
Moritomo, A.5
Kontani, T.6
Kageyama, S.7
Ohta, M.8
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23
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66249122284
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European Pharmacopoeia (Ph. Eur.) Suppl. 6.3, 2009; 2373.
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European Pharmacopoeia (Ph. Eur.) Suppl. 6.3, 2009; 2373.
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24
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79952830029
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Process for the purification of meloxicam
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Eur. Pat. EP 1645559, 350700
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Vigano, E.; Landonio, E. Process for the purification of meloxicam. Eur. Pat. EP 1645559, 2006. Chem. Abstr. 2006, 144, 350700.
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Chem. Abstr
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Vigano, E.1
Landonio, E.2
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25
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66249118244
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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.
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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.
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26
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66249145623
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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
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(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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27
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66249090424
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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
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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.
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28
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66249118920
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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.
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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.
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