- 5-aminothiazole non-steroidal anti-inflammatory compound as well as preparation method and application thereof
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The invention discloses a 5-aminothiazole non-steroidal anti-inflammatory compound. The compound which is efficient, low in toxicity and small in side effect is prepared from an ester intermediate containing a thiazine ring and a 5-aminothiazole derivative through a transesterification reaction. The preparation method of the compound is simple, the compound has the active groups of the existing non-steroidal anti-inflammatory medicine; meanwhile, the special change of the nitrogen atom position is also designed; compared with the existing non-steroidal anti-inflammatory medicines, the compoundhas better anti-inflammatory and analgesic effects, particularly has good curative effects on arthritis, osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, soft tissue inflammation and thelike, has small toxic and side effects on human bodies, and has a very wide market prospect.
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Paragraph 0106; 0146-0147; 0150
(2020/09/20)
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- Preparation method of tenoxicam
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The invention discloses a preparation method of tenoxicam and belongs to the technical field of medicine preparation. The preparation method comprises the following steps: using 3-chlorosulfonyl-2-thiophenecarboxylate, namely TNXK-0 as a raw material to synthesize 3-((N-(methoxycarbonyl) methyl) sulfonyl)-2-thiophenecarboxylate, namely TNXK-1; using the TNXK-1 as a raw material to synthesize 4-hydroxy-2H-thieno (2,3e)-1,2-thiazine-3-methyl formate-1,1-dioxide, namely TNXK-2; using the TNXK-2 as a raw material to synthesize 4-hydroxy-2-methyl-2H-thieno (2,3e)-1,2-thiazine-3-methyl formate-1,1-dioxide, namely TNXK-3; using the TNXK-3 and 2-aminopyridine as raw materials to synthesize the tenoxicam. The preparation method of the tenoxicam, disclosed by the invention, has the advantages of simple process, high yield and low cost; the purity of an obtained product is high.
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Paragraph 0051-0055; 0065; 0069; 0075; 0079; 0085; 0089
(2017/10/26)
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- Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity
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Meloxicam (5), an NSAID in the enol-carboxamide class, was developed on the basis of its antiinflammatory activity and relative safety in animal models. In subsequent screening in microsomal assays using human COX-1 and COX-2, we discovered that it possessed a selectivity profile for COX-2 superior to piroxicam and other marketed NSAIDs. We therefore embarked on a study of enol-carboxamide type compounds to determine if COX-2 selectivity and potency could be dramatically improved by structural modification. Substitution at the 6- and 7-positions of the 4-oxo-1,2-benzothiazine-3- carboxamide, alteration of the N-methyl substituent, and amide modification were all examined. In addition we explored several related systems including the isomeric 3-oxo-1,2-benzothiazine-4-carboxamides, thienothiazines, indolothiazines, benzothienothiazines, naphthothiazines, and 1,3- and 1,4- dioxoisoquinolines. While a few examples were found with greater potency in the COX-2 assay, no compound tested had a better COX-2/COX-1 selectivity profile than that of 5.
- Lazer, Edward S.,Miao, Clara K.,Cywin, Charles L.,Sorcek, Ronald,Wong, Hin-Chor,Meng, Zhaoxing,Potocki, Ian,Hoermann, MaryAnn,Snow, Roger J.,Tschantz, Matt A.,Kelly, Terence A.,McNeil, Daniel W.,Coutts, Simon J.,Churchill, Laurie,Graham, Anne G.,David, Eva,Grob, Peter M.,Engel, Wolfhard,Meier, Hans,Trummlitz, Günter
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p. 980 - 989
(2007/10/03)
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- Analogues and Derivatives of Tenoxicam. 1. Synthesis and Antiinflammatory Activity of Analogues with Different Residues on the Ring Nitrogen and the Amide Nitrogen
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The synthesis of tenoxicam, 4-hydroxy-2-methyl-N-2-pyridyl-2H-thieno-1,2-thiazine-3-carboxamide 1,1-dioxide (1e), and of the analogues with various residues on the ring nitrogen and the amide nitrogen is described.This new class of "oxicams" has pronounced antiinflammatory and analgesic properties.The very specific structure-activity relationship of isomeric and isosteric groups at the amide nitrogen has been evaluated.The substituent in position 2 also has a great influence on the pharmacological properties.Tenoxicam is presently underrgoing clinical trials.
- Binder, Dieter,Hromatka, Otto,Geissler, Franz,Schmied, Karl,Noe, Christian R.,et al.
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p. 678 - 682
(2007/10/02)
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- Thienothiazines
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The present invention relates to compounds of the formula STR1 wherein A together with the two carbon atoms to which it is attached forms the group STR2 AND THE BROKEN LINE REPRESENTS THE DOUBLE BOND IN GROUP (A); R1 represents a lower alkyl group; R2 represents the residue of an aromatic heterocyclic ring containing from 1 to 4 hetero atoms, which may be substituted by one or two lower alkyl groups, or a phenyl group which may be substituted by halogen, hydroxy, lower alkyl, trifluoromethyl or lower alkoxy and R3 and R4 each represent a hydrogen atom or a lower alkyl group. Also provided are methods for their preparation. The thienothiazine derivatives provided by this invention have anti-flammatory, analgesic and antirheumatic activity.
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