- Tenoxicam preparation method
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The invention relates to a tenoxicam preparation method. Tenoxicam is prepared by taking 3-chlorosulfonylthiophene-2-dimethyl carbonate as an initial raw material, reacting 3-chlorosulfonylthiophene-2-dimethyl carbonate with 2-amino-N-pyridyl acetamide, performing cyclization in an alkaline condition, and performing methylation with dimethyl carbonate. The preparation route is shown as in the description. The preparation method has advantages that the raw materials are low in price and are available and the production cost is saved. In the meantime, final aminolysis is not required in the preparation method, the reaction is complete, and the yield is no less than 85%. The raw materials and product are not carbonized or decomposed, the side reaction is reduced, and the product is easy to be purified, so that the purity of the product can reach 99.98%. The preparation method is suitable for industrial production.
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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 0056-0060; 0066; 0070; 0076; 0080; 0086; 0090
(2017/10/26)
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- Synthesis method of tenoxicam
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The invention relates to a synthesis method of tenoxicam. The synthesis method takes 3-[[N-(methoxycarbonyl)methyl]sulfonyl]-2-thiophenecarboxylate as a starting raw material and comprises the following steps: carrying out cyclization on the starting raw material to obtain a 4-hydroxy-2H-thieno[2,3-e]-1,2-thiazine-3-methyl formate1,1-dioxide intermediate; carrying out reaction on the 4-hydroxy-2H-thieno[2,3-e]-1,2-thiazine-3-methyl formate1,1-dioxide intermediate, dimethyl carbonate and 2-aminopyridine through a one-pot method to prepare the tenoxicam. A synthesis route is as follows: the synthesis route is shown in the description. The synthesis method provided by the invention has the advantages that the synthesis method has a short route and no hazardous process and is green and environmentally friendly; a final aminolysis step is avoided and raw materials react completely; the yield is more than or equal to 80 percent; the raw materials and a product are not easy to carbonize and decompose and side reaction is reduced; the product is easy to purify and the purity of the product can reach 99.85 percent; the synthesis method is a synthesis process capable of realizing industrialized production.
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Paragraph 0026; 0027; 0028; 0029
(2017/08/30)
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- Organotin-drug interactions. Organotin adducts of tenoxicam: Synthesis and characterization of the first organotin complex of tenoxicam
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The synthesis and spectral characterization of the novel organotin complexes [SnBu2(ten)] (1) and [SnBu2(Hten)2] (2) of the potent and widely used anti-inflammatory drug tenoxicam (H2ten) are reported. A crystal-structure determination of 1 showed that, in this complex, the ligand is doubly deprotonated at the hydroxy O-atom and the amide N-atom and is coordinated to the SnBu2 fragment via four- and six-membered chelate rings. An extended network of Sn - O - Sn, C - H ··· O and C - H ··· π contacts lead to aggregation and a supramolecular assembly. Potentiometric titrations in nonaqueous solutions support the ionization of the drug by removal of the second H-atom, the amide H-atom, in the presence of the diorganotin(IV) fragment. The K(a) values of the poorly H2O-soluble drug tenoxicam were obtained spectrophotometrically in aqueous solutions of constant ionic strength.
- Demertzis, Mavroudis A.,Hadjikakou, Sotiris K.,Kovala-Demertzi, Dimitra,Koutsodimou, Aglaia,Kubicki, Maciej
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p. 2787 - 2801
(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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- Pharmaceutical preparation for the therapeutic treatment of rheumatic diseases
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Pharmaceutical preparation containing phospholipids for the therapeutic treatment of rheumatic diseases which contain in addition to the antiphlogistically acting oxicam derivatives of the general formula STR1 special 1,2-diacyl-glycero-3-phosphocholines wherein 75-86% by weight of the acyl radicals are unsaturated fatty acid radicals, and the preparation thereof.
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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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