59804-37-4

Basic information

• Product Name: Tenoxicam
• Synonyms: MOBIFLEX;tilcotil;TENOXICAM;4-HYDROXY-2-METHYL-N-2-PYRIDINYL-2H-THIENO[2,3-E]-1,2-THIAZINE-3-CARBOXAMIDE 1,1-DIOXIDE;AKOS 93347;3-e)-1,2-thiazine-3-carboxamide,4-hydroxy-2-methyl-n-2-pyridinyl-2h-thieno(;4-hydroxy-2-methyl-n-2-pyridinyl-2h-thieno(2,3-e)-1,2-thiazine-3-carboxamide;ro12-0068
• CAS NO: 59804-37-4
• Molecular Formula: C₁₃H₁₁N₃O₄S₂
• Molecular Weight: 337.37
• EINECS: 1312995-182-4
• Product Categories: Active Pharmaceutical Ingredients;Tenoxicam;Intermediates & Fine Chemicals;Pharmaceuticals;Fused Ring Systems;Lipid signaling;Amines;Heterocycles;Sulfur & Selenium Compounds;Pharmaceutical raw material;API;TARACTAN
• Mol File: 59804-37-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 209-2130C (dec)
• Appearance: yellow crystalline powder
• Density: 1.4737 (rough estimate)
• Refractive Index: 1.6390 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Practically insoluble in water, sparingly soluble in methylene chloride, very slightly soluble in anhydrous ethanol. It dissolves in solutions of acids and alkalis.
• PKA: pKa1 5.3, pKa2 1.1(at 25℃)
• Water Solubility: 61.9mg/L(32 oC)
• CAS DataBase Reference: Tenoxicam(CAS DataBase Reference)
• NIST Chemistry Reference: Tenoxicam(59804-37-4)
• EPA Substance Registry System: Tenoxicam(59804-37-4)

Safety Data

• Hazard Codes: T,Xi
• Statements: 23/24/25-36/37/38
• Safety Statements: 36/37/39-45-36-26-36/37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 2
• RTECS: XJ9095060
• HazardClass: 6.1
• Hazardous Substances Data: 59804-37-4(Hazardous Substances Data)

Usage

Description

Tenoxicam, a non-steroidal anti-inflammatory agent (NSAID), is a thienothiazine-derived monocarboxylic acid amide. It is structurally similar to piroxicam and the now withdrawn isoxicam. Tenoxicam is known for its effectiveness in treating pain and inflammation associated with osteoarthritis and rheumatoid arthritis. It is also used for the short-term treatment of acute musculoskeletal disorders, such as strains, sprains, and other soft-tissue injuries. Chemically, it is a yellow crystalline powder and is marketed under the brand name Tilcotil.

Uses

Used in Pharmaceutical Industry:
Tenoxicam is used as a non-steroidal anti-inflammatory agent (NSAID) for the treatment of pain and inflammation in osteoarthritis and rheumatoid arthritis. It is also indicated for short-term treatment of acute musculoskeletal disorders, including strains, sprains, and other soft-tissue injuries.
Used in Research and Development:
Tenoxicam is used as a standard in microanalysis of NSAIDs by spectrophotometry to test its effect on surface potential and membrane fluidity modification in phosphoglyceride monolayers. Additionally, it is used as a non-steroidal anti-inflammatory agent to study its effects on root gravitropism in Arabidopsis thaliana.
Used in Antipsychotic Applications:
Although not explicitly mentioned in the provided materials, Tenoxicam may also be used in antipsychotic applications due to its anti-inflammatory properties, which can potentially help in managing inflammation-related symptoms in certain psychiatric disorders.

Biochem/physiol Actions

Tenoxicam (TX) possesses antipyretic?and analgesic effects. It elicits radical scavenging activity and has the potential to treat enkylosing spondylitis, extra-articular diseases, acute gout, and rheumatic diseases. It is also effective in treating primary dysmenorrhea, postpartum uterine contraction pain, and post-operation backaches. TX is capable of inhibiting prostaglandin synthesis.

Clinical Use

NSAID and analgesic

Drug interactions

Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia. Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage). Antibacterials: possibly increased risk of convulsions with quinolones. Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxaban. Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine. Antidiabetic agents: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib. Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics. Lithium: excretion decreased. Pentoxifylline: increased risk of bleeding. Tacrolimus: increased risk of nephrotoxicity.

Metabolism

Metabolised in the liver via cytochrome P450 2C9 to several pharmacologically inactive metabolites (mainly 5'-hydroxy-tenoxicam). Metabolites are excreted mainly in the urine; there is some biliary excretion of glucuronide conjugates of the metabolites.

InChI:InChI=1/C13H11N3O4S2/c1-16-10(13(18)15-9-4-2-3-6-14-9)11(17)12-8(5-7-21-12)22(16,19)20/h2-7,17H,1H3,(H,14,15,18)

Synthetic route

4-hydroxy-N-2-pyridyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide (106820-67-1) + carbonic acid dimethyl ester (616-38-6) → tenoxicam (59804-37-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 7h; Large scale;	89%

2-aminopyridine (504-29-0) + methyl 4-hydroxy-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide (98827-44-2) + carbonic acid dimethyl ester (616-38-6) → tenoxicam (59804-37-4)

Conditions	Yield
Stage #1: methyl 4-hydroxy-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide; carbonic acid dimethyl ester With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 5h; Large scale; Stage #2: 2-aminopyridine With potassium carbonate In N,N-dimethyl-formamide for 7h; Large scale;	83%

2-aminopyridine (504-29-0) + 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine,1,1-dioxide (59804-25-0) → tenoxicam (59804-37-4)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Concentration; Reflux;	76.9%
In xylene for 7h; Heating;	75%

3-chlorothiophene-2-carboxylic acid (59337-89-2) → tenoxicam (59804-37-4)

Conditions	Yield
Multi-step reaction with 7 steps 1: 210 g / 1.) sodium bisulfite, NaOH, CuCl, 2.) KCl / H2O / 16 h / 143 °C 2: POCl3, PCl5 / 1.5 h / Heating 3: 95 percent / CHCl3 / 3 h / Heating 4: 71 percent / pyridine / 4 h / Ambient temperature 5: 58 percent / CH3ONa / methanol; hexane / 6 h / Heating 6: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 16 h 7: 75 percent / xylene / 7 h / Heating View Scheme
Multi-step reaction with 6 steps 1: 210 g / 1.) sodium bisulfite, NaOH, CuCl, 2.) KCl / H2O / 16 h / 143 °C 2: POCl3, PCl5 / 1.5 h / Heating 3: 95 percent / CHCl3 / 3 h / Heating 4: 84 percent / pyridine / 2 h / Ambient temperature 5: 11 g / CH3ONa / methanol / a) RT, 15 min, b) reflux, 25 min 6: 75 percent / xylene / 7 h / Heating View Scheme

2-(carbomethoxy)thiophene-3-sulfonyl chloride (59337-92-7) → tenoxicam (59804-37-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 71 percent / pyridine / 4 h / Ambient temperature 2: 58 percent / CH3ONa / methanol; hexane / 6 h / Heating 3: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 16 h 4: 75 percent / xylene / 7 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 84 percent / pyridine / 2 h / Ambient temperature 2: 11 g / CH3ONa / methanol / a) RT, 15 min, b) reflux, 25 min 3: 75 percent / xylene / 7 h / Heating View Scheme
Multi-step reaction with 4 steps 1: water / 6 h / 20 °C / pH 7 - 8 2: sodium methylate / methanol / 2 h / Reflux 3: sodium hydroxide / methanol / 3 h / 20 °C 4: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux View Scheme

3-chlorosulfonyl-thiophene-2-carboxylic acid chloride (59337-91-6) → tenoxicam (59804-37-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / CHCl3 / 3 h / Heating 2: 71 percent / pyridine / 4 h / Ambient temperature 3: 58 percent / CH3ONa / methanol; hexane / 6 h / Heating 4: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 16 h 5: 75 percent / xylene / 7 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 95 percent / CHCl3 / 3 h / Heating 2: 84 percent / pyridine / 2 h / Ambient temperature 3: 11 g / CH3ONa / methanol / a) RT, 15 min, b) reflux, 25 min 4: 75 percent / xylene / 7 h / Heating View Scheme

methyl 4-hydroxy-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide (98827-44-2) → tenoxicam (59804-37-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 16 h 2: 75 percent / xylene / 7 h / Heating View Scheme

methyl 3-<<<(methoxcarbonyl)methyl>amino>sulfonyl>-2-thiophenecarboxylate (106820-63-7) → tenoxicam (59804-37-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 58 percent / CH3ONa / methanol; hexane / 6 h / Heating 2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 16 h 3: 75 percent / xylene / 7 h / Heating View Scheme
Multi-step reaction with 3 steps 1: sodium methylate / methanol / 2 h / Reflux 2: sodium hydroxide / methanol / 3 h / 20 °C 3: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux View Scheme

methyl 3-<-N-methylamino>sulfonyl>-2-thiophenecarboxylate (59804-24-9) → tenoxicam (59804-37-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 11 g / CH3ONa / methanol / a) RT, 15 min, b) reflux, 25 min 2: 75 percent / xylene / 7 h / Heating View Scheme

dibutylbis[4-(hydroxy-κO)-2-methyl-N-(pyridin-2-yl-κN)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxidato]tin → [Sn(C4H9)2(C6H2S2NCH3O3C(O)NC5H4N)]*0.5CH3OH + tenoxicam (59804-37-4)

Conditions	Yield
In methanol; acetonitrile slow crystn. of soln.;
In chloroform-d1

2-aminopyridine (504-29-0) → tenoxicam (59804-37-4)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran-d8 / 2 h / 20 °C / Large scale 1.2: 20 °C / Large scale 2.1: triethylamine / ethyl acetate / 0 - 20 °C / Large scale 3.1: sodium methylate / methanol / 2 h / Reflux; Large scale 4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / Large scale View Scheme

2-amino-N-(pyridin-2-yl)acetamide → tenoxicam (59804-37-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / ethyl acetate / 0 - 20 °C / Large scale 2: sodium methylate / methanol / 2 h / Reflux; Large scale 3: potassium carbonate / N,N-dimethyl-formamide / 7 h / Large scale View Scheme

tenoxicam (59804-37-4) → 4-(N,N-dimethylaminobutyryloxy)-2-methyl-N-2-pyridyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide-1,1-dioxide hydrochloride

Conditions	Yield
Stage #1: tenoxicam With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3h; Stage #2: With hydrogenchloride In dichloromethane	80.1%

tenoxicam (59804-37-4) + 4-dimethylamino-butyric acid (693-11-8) → 4-(N,N-dimethylaminobutyryloxy)-2-methyl-N-2-pyridyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide-1,1-dioxide hydrochloride

Conditions	Yield
Stage #1: tenoxicam; 4-dimethylamino-butyric acid With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3h; Stage #2: With hydrogenchloride	80.1%

tenoxicam (59804-37-4) + methyl iodide (74-88-4) → 4-methoxy-2-methyl-N-(pyridin-2-yl)-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide + 2-{[(4-hydroxy-2-methyl-1,1-dioxido-2H-thieno[2,3-e][1,2]thiazine-3-yl)carbonyl]amino}-1-methylpyridinium (868522-78-5)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 120h;	A 12% B 72%

potassium trichloro(η2-ethene)platinate(II) hydrate + tenoxicam (59804-37-4) → trans-[dichloro(4-hydroxy-2-methyl-N-2-pyridyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide-1,1-dioxide)(η2-ethene)platinum(II)] (588699-00-7)

Conditions	Yield
In ethanol a warmed soln. of ligand mixed with a soln. of Pt compd., stirred at room temp. for 30 min; ppt. filtered, washed (ethanol, diethyl ether), recrystd. (benzene); elem. anal.;	66%

tenoxicam (59804-37-4) → 5-methyl-5H,6H-pyrido[2',1':2,3]pyrimido[5,4-c]thieno[2,3-e][1,2]thiazin-6-one 4,4-dioxide

Conditions	Yield
With trichlorophosphate at 100℃; for 3h;	56%

benzoyl chloride (98-88-4) + tenoxicam (59804-37-4) → 2-methyl-1,1-dioxido-3-[(pyridin-2-ylamino)carbonyl]-2H-thieno[2,3-e][1,2]thiazin-4-yl benzoate hydrochloride

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 3h;	43%

cinnamoyl chloride (102-92-1) + tenoxicam (59804-37-4) → 2-methyl-1,1-dioxido-3-[(pyridin-2-ylamino)carbonyl]-2H-thieno[2,3-e][1,2]thiazin-4-yl 3-phenylprop-2-enoate hydrochloride

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 3h;	39%

tenoxicam (59804-37-4) + acetyl chloride (75-36-5) → 2-methyl-1,1-dioxido-3-[(pyridin-2-ylamino)carbonyl]-2H-thieno[2,3-e][1,2]thiazin-4-yl acetate hydrochloride

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 3h;	39%

2-furancarbonyl chloride (527-69-5) + tenoxicam (59804-37-4) → 2-methyl-1,1-dioxido-3-[(pyridin-2-ylamino)carbonyl]-2H-thieno[2,3-e][1,2]thiazin-4-yl 2-furoate hydrochloride

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 3h;	24%

water (7732-18-5) + copper(II) acetate monohydrate (6046-93-1) + tenoxicam (59804-37-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → C26H24CuN6O10S4*4H2O*2C3H7NO

Conditions	Yield
Stage #1: copper(II) acetate monohydrate; tenoxicam In methanol for 1h; Reflux; Stage #2: water; N,N-dimethyl-formamide for 24h;	10%

tenoxicam (59804-37-4) → 2-aminopyridine (504-29-0)

Conditions	Yield
With water In ethanol at 100℃; for 4h; pH 1;

tenoxicam (59804-37-4) → 2-aminopyridine (504-29-0) + 4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxylic acid 1,1-dioxide + 2-Methylamino-3-oxo-3-(3-sulfo-thiophen-2-yl)-propionic acid

Conditions	Yield
With water In ethanol at 100℃; Rate constant; other pH;

tenoxicam (59804-37-4) → 4-methyl-1-phenyl-1,4-dihydropyrazolo[4,3-c]thieno[2,3-e][1,2]thiazin-3(2H)-one 5,5-dioxide

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 57 percent / dimethylformamide / 8 h / 100 °C 3: 47 percent / N,N-dimethylaniline; POCl3 / toluene / 7 h / 100 °C View Scheme

tenoxicam (59804-37-4) → N-(2-chlorophenyl)-4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 51 percent / dimethylformamide / 10 h / 140 °C View Scheme

tenoxicam (59804-37-4) → 4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxylic acid 2-phenylhydrazide 1,1-dioxide (868393-67-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 57 percent / dimethylformamide / 8 h / 100 °C View Scheme

tenoxicam (59804-37-4) → 4-hydroxy-N-(4-methoxyphenyl)-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 82 percent / dimethylformamide / 3 h / 130 °C View Scheme

tenoxicam (59804-37-4) → 4-hydroxy-2-methyl-N-[3-(trifluoromethyl)phenyl]-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 37 percent / dimethylformamide / 20 h / 150 °C View Scheme

tenoxicam (59804-37-4) → 4-hydroxy-2-methyl-N-[4-(trifluoromethyl)phenyl]-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 44 percent / dimethylformamide / 18 h / 150 °C View Scheme

tenoxicam (59804-37-4) → 4-hydroxy-2-methyl-N-phenyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide (59804-36-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 74 percent / dimethylformamide / 3 h / 130 °C View Scheme

tenoxicam (59804-37-4) → 4-hydroxy-N-(3-methylphenyl)-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide (59804-41-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 65 percent / dimethylformamide / 6 h / 130 °C View Scheme

tenoxicam (59804-37-4) → N-(3-chlorophenyl)-4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide (59804-42-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 78 percent / dimethylformamide / 10 h / 140 °C View Scheme

tenoxicam (59804-37-4) → ethyl 4-hydroxy-2-methyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide (98827-42-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 58 percent / EtONa / 12 h / 80 °C View Scheme

tenoxicam (59804-37-4) → 4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxylic acid 1,1-dioxide

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / K2CO3 / acetone / 120 h / 20 °C 2: 57 percent / aq. NaOH / ethanol / 3 h / 80 °C View Scheme

Upstream product

• 106820-67-1 4-hydroxy-N-2-pyridyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide 
• 616-38-6 carbonic acid dimethyl ester 
• 504-29-0 2-aminopyridine 
• 98827-44-2 methyl 4-hydroxy-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide 
• 59804-24-9 methyl 3-<-N-methylamino>sulfonyl>-2-thiophenecarboxylate 
• 106820-63-7 methyl 3-<<<(methoxcarbonyl)methyl>amino>sulfonyl>-2-thiophenecarboxylate 
• 59337-91-6 3-chlorosulfonyl-thiophene-2-carboxylic acid chloride 
• 59337-92-7 2-(carbomethoxy)thiophene-3-sulfonyl chloride 
• 59337-89-2 3-chlorothiophene-2-carboxylic acid 
• 59804-25-0 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine,1,1-dioxide 

Downstream Products

• 1428327-93-8 tenoxicam-benzoic acid 
• 1400663-47-9 tenoxicam-salicylic acid 
• 1428327-94-9 tenoxicam-catechol 
• 1428327-95-0 tenoxicam-resorcinol 
• 1428327-96-1 tenoxicam-pyrogallol 
• 5380-42-7 thiophene-2-carboxylic acid methyl ester 
• 54166-60-8 methyl (pyridin-2-ylcarbamoyl)formate 
• 94040-09-2 2,3-Dihydro-2-methyl-3-oxo-thieno<2,3-d>isothiazol-1,1-dioxid 
• 868393-66-2 4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxylic acid 1,1-dioxide 
• 59804-42-1 N-(3-chlorophenyl)-4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide 
• 59804-41-0 4-hydroxy-N-(3-methylphenyl)-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide 
• 59804-36-3 4-hydroxy-2-methyl-N-phenyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide 
• 868393-67-3 4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxylic acid 2-phenylhydrazide 1,1-dioxide 

Relevant articles and documents

Synthesis method of tenoxicam

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.

Preparation method of tenoxicam

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.

Analogues and Derivatives of Tenoxicam. 1. Synthesis and Antiinflammatory Activity of Analogues with Different Residues on the Ring Nitrogen and the Amide Nitrogen

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.