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71125-38-7 Usage

Description

Different sources of media describe the Description of 71125-38-7 differently. You can refer to the following data:
1. Known as a nonsteroidal anti-inflammatory drug (NSAID), Meloxicam is commonly used to treat pain or inflammation caused by rheumatoid arthritis and osteoarthritis in adults. It is also used to treat juvenile rheumatoid arthritis in children who are at least 2 years old. It is effective to reduce pain, inflammation, swelling, and stiffness of the joints. Developed by Boehringer-Ingelheim, Meloxicam is a derivative of oxicam that can relieve the symptoms of arthritis, primary dysmenorrhea, fever with analgesic and antipyretic properties. Meloxicam was approved for use in April 2000. Anti-inflammatory effects of meloxicam function by inhibiting the prostaglandin synthetase (cyclooxygenase 1 and 2) which results in a decrease of the synthesis of prostaglandins. As prostaglandins are chemicals that contribute to inflammation especially within joints, which leads to the common symptoms of pain, tenderness, and swelling associated with arthritis, inhibition of their synthesis can be associated with the analgesic and antipyretic effects of meloxicam. As a result, inflammation and its accompanying symptoms are reduced. Meloxicam starts to relieve pain about 30 to 60 minutes after administration.
2. Mobec was launched in Columbia, Denmark, France, Germany, Ireland, Italy, Netherlands, S. Africa, Sweden, and the UK for osteo- and rheumatoid arthritis as an NSAID. It can be synthesized in four steps from benzisothiazolo-3(2H)-one- 1,1-dioxide. By shutting down prostaglandin synthesis, it has antiinflammatory, antipyretic and analgesic properties. This is accomplished by preferentially inhibiting the COX-2 system relative to the COX-I which also leads to an improved GI safety profile relative to naproxen, diclofenac and prioxicam. It can also interfere with neutrophil function like degranulation. Meloxicam did not inhibit proteoglycan synthesis in osteroarthitic cartilage or chondrocytes and had no effect on platelet aggregation. It is metabolized by the P450 2C9 system into four metabolites which are all inactive.
3. Viramune was launched in the US for use in combination with nucleoside analogs to treat HIV-infected adults who have experienced clinical and/or immulogic deterioration. It can be prepared in four steps from 2chloro-4-methyl-3-nitropyridine. It is a potent inhibitor of HIV-1 reverse transcriptase with no rnuscarinic or benzodiazepine activity. Mechanistically, it is a non-competitive non-nucleoside inhibitor. It has a low toxicity for uninfected cells most likely due to its specificity, i.e., it does not inhibit eukaryotic DNA polymerase α, β, γ and δ. HIV-2, SIV and FeLV are not affected by nevirapine and monotherapy is limited by the rapid onset of resistance.
4. Meloxicam is a selective inhibitor of COX-2 (IC50s = 11.8 and 143 μM for COX-2 and COX-1, respectively, in an enzyme activity assay) and a non-steroidal anti-inflammatory drug (NSAID). Meloxicam (0.03%) reduces croton oil-induced increases in TNF-α and IL-1β mRNA levels and increases IL-10 mRNA levels in cornea in a rabbit model of acute ocular inflammation. It inhibits pleural plasma exudation in a carrageenan-induced rat model of pleurisy when administered at a dose of 3 mg/kg. In a canine model of unilateral osteoarthritis of the right stifle joint, meloxicam reduces prostaglandin E2 (PGE2) levels in plasma and right stifle joint synovial fluid when administered at a dose of 0.2 mg/kg. Formulations containing meloxicam have been used in the treatment of osteoarthritis and rheumatoid arthritis.

References

https://en.wikipedia.org/wiki/Meloxicam https://www.drugbank.ca/drugs/DB00814 https://www.drugs.com/meloxicam.html http://www.medicinenet.com/meloxicam/article.htm

Chemical Properties

Light Yellow Solid

Uses

Different sources of media describe the Uses of 71125-38-7 differently. You can refer to the following data:
1. Preferential cyclooxygenase (COX-2) inhibitor. Sudoxicam and Meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class.
2. angiotensin 2 receptor antagonist
3. For symptomatic treatment of arthritis and osteoarthritis.
4. An inhibitor of Cox-1 and Cox-2, selective for Cox-2.
5. Preferential cyclooxygenase (COX-2) inhibitor. Used as an anti-inflammatory.

Definition

ChEBI: A benzothiazine that is piroxicam in which the pyridin-2-yl group is replaced by a 5-methyl-1,3-thiazol-2-yl group. A non-steroidal anti-inflammatory drug and selective inhibitor of COX-2, it is used particularly for the management of rheumatoid arthritis.

Indications

Meloxicam (Mobic), recently introduced for the treatment of osteoarthritis, is also used for rheumatoid arthritis and certain acute conditions. Although meloxicam is sometimes reported to be a selective COX-2 inhibitor, it is considerably less selective than celecoxib or rofecoxib. Its adverse effects are similar to those of piroxicam and other NSAIDs; however, the frequency of GI side effects is lower for meloxicam than for piroxicam and several other NSAIDs.

Manufacturing Process

A mixture of 26.9 g (0.1 mol) of the 1,1-dioxide of methyl 4-hydroxy-2- methyl-2H-1,2-benzothiazine-3-carboxylate and 12.5 g (0.11 mol) of 2- amino-5-methylthiazole was refluxed in 4 liters of xylene for 24 hours in a nitrogen atmosphere. The methanol formed by the reaction was removed by means of a 4-A-molecular sieve mounted in a Soxhlet-extractor. The hot reaction solution was filtered. Upon cooling and standing overnight, the crude product separated out of the filtrate in the form of crystals (32.0 g, 91% of theory). After recrystallization from ethylene chloride 26.0 g (74% of theory) of 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3- carboxamide-1,1-dioxide were obtained; M.P.: 254°C (decomp.).

Brand name

Mobic (Boehringer Ingelheim).

Therapeutic Function

Antiinflammatory

General Description

Meloxicam (Mobic) is a selective COX-2 inhibitor amongoxicams indicated for use in RA and OA. It also has a relativelylong half-life of 15 to 20 hours and has a much lowerrate of serious GI side effects and a lower than average riskof nephropathy when compared with other conventionalNSAIDs.196 The recommended dose is 7.5 mg once dailywith a maximum of 15 mg/d. Meloxicam is metabolized inhumans mainly by CYP2C9 (with a minor contribution viaCYP3A4) to 5'-hydroxymethylmeloxicam and 5 carboxymeloxicam.In large-scale comparative trials, meloxicam was foundto be at least as effective as most conventional NSAIDs inthe treatment of rheumatic disease or postoperative pain, buthas demonstrated a more favorable GI tolerability profile.

Clinical Use

In April 2000, the U.S. FDA approved meloxicam for the treatment of osteoarthritis. When meloxicam was initially introduced in the United Kingdom, it was promoted as a selective COX-2 inhibitor.

Veterinary Drugs and Treatments

Meloxicam is principally used for the symptomatic treatment of osteoarthritis in dogs. Short-term (single dose injectable) use is also approved (in the USA) for cats for the control of postoperative pain and inflammation associated with orthopedic surgery, ovariohysterectomy and castration when administered prior to surgery.

Metabolism

Meloxicam, however, is less selective than celecoxib and much less selective than rofecoxib in in vitro studies. Meloxicam is readily absorbed when administered orally and is highly bound to plasma proteins. Meloxicam is extensively metabolized in the liver, primarily by CYP2C9 and, to a lesser extent, by CYP3A4. The advantages of meloxicam over celecoxib and rofecoxib in the treatment of osteoarthritis (or rheumatoid arthritis) are not readily apparent.

Check Digit Verification of cas no

The CAS Registry Mumber 71125-38-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,1,2 and 5 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 71125-38:
(7*7)+(6*1)+(5*1)+(4*2)+(3*5)+(2*3)+(1*8)=97
97 % 10 = 7
So 71125-38-7 is a valid CAS Registry Number.

71125-38-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (M1959)  Meloxicam  >98.0%(HPLC)

  • 71125-38-7

  • 5g

  • 410.00CNY

  • Detail
  • TCI America

  • (M1959)  Meloxicam  >98.0%(HPLC)

  • 71125-38-7

  • 25g

  • 1,240.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001080)  Meloxicam  European Pharmacopoeia (EP) Reference Standard

  • 71125-38-7

  • Y0001080

  • 1,880.19CNY

  • Detail
  • USP

  • (1379401)  Meloxicam  United States Pharmacopeia (USP) Reference Standard

  • 71125-38-7

  • 1379401-400MG

  • 7,318.35CNY

  • Detail

71125-38-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name meloxicam

1.2 Other means of identification

Product number -
Other names Movalis

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:71125-38-7 SDS

71125-38-7Synthetic route

meloxicam potassium salt monohydrate
892395-40-3

meloxicam potassium salt monohydrate

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
Stage #1: meloxicam potassium salt monohydrate With potassium hydroxide; pyrographite In ethanol; water at 40 - 45℃; for 0.666667h;
Stage #2: With acetic acid In ethanol; water at 10 - 30℃; for 2.5h; pH=3 - 5; Product distribution / selectivity;
98.5%
Stage #1: meloxicam potassium salt monohydrate With potassium hydroxide; pyrographite In ethanol; water at 40 - 45℃; for 0.666667h;
Stage #2: With hydrogenchloride In ethanol; water at 10 - 30℃; for 2.5h; pH=3 - 5; Product distribution / selectivity;
97.1%
Stage #1: meloxicam potassium salt monohydrate With potassium hydroxide In ethanol; water at 50 - 55℃; Large scale reaction;
Stage #2: With hydrogenchloride In ethanol; water at 65 - 70℃; Reflux; Large scale reaction;
91%
5-methyl-2-thiazol-2-amine
7305-71-7

5-methyl-2-thiazol-2-amine

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
In o-xylene for 24h; Product distribution / selectivity; Heating / reflux;95%
In xylene at 139 - 140℃; for 32 - 37h; Product distribution / selectivity; Heating / reflux; Molecular sieve;92.48%
5-methyl-2-thiazol-2-amine
7305-71-7

5-methyl-2-thiazol-2-amine

methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
35511-15-0

methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
In o-xylene at 25 - 145℃; for 33.5 - 38h; Industry scale;88.8%
In xylene for 48h; Heating;
N-methylglucamine salt of meloxicam
244241-52-9

N-methylglucamine salt of meloxicam

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
Stage #1: N-methylglucamine salt of meloxicam In water at 70℃; for 0.5h; CN1 carbon;
Stage #2: With water; acetic acid at 70℃; for 0.25h; pH=4.6; Product distribution / selectivity;
87%
5-methyl-2-thiazol-2-amine
7305-71-7

5-methyl-2-thiazol-2-amine

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
With 1,2-dichloro-ethane76%
5-methyl-2-thiazol-2-amine
7305-71-7

5-methyl-2-thiazol-2-amine

4-hydroxy-2-methyl-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide
24683-25-8

4-hydroxy-2-methyl-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
With toluene-4-sulfonic acid; 1,2-dichloro-ethane48%
methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-acetate 1,1-dioxide
6639-62-9

methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-acetate 1,1-dioxide

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 25percent MeONa/MeOH / toluene / 4 h / 80 °C
2: 1M aq.NaOH / ethanol / 24 h / Ambient temperature
3: xylene / 48 h / Heating
View Scheme
methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
35511-14-9

methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1M aq.NaOH / ethanol / 24 h / Ambient temperature
2: xylene / 48 h / Heating
View Scheme
saccharin
81-07-2

saccharin

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) NaH / 1.) DMF, 50 deg C, 30 min, 2.) DMF, 4 h
2: 25percent MeONa/MeOH / toluene / 4 h / 80 °C
3: 1M aq.NaOH / ethanol / 24 h / Ambient temperature
4: xylene / 48 h / Heating
View Scheme
5-methyl-2-thiazol-2-amine
7305-71-7

5-methyl-2-thiazol-2-amine

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

A

4-hydroxy-2-methyl-N-ethyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

4-hydroxy-2-methyl-N-ethyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

B

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
In xylene at 139 - 140℃; for 32 - 37h;
Reaxys ID: 11649320

Reaxys ID: 11649320

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
Stage #1: With sodium methylate In methanol for 0.166667h;
Stage #2: With pyrographite In methanol
Stage #3: With hydrogenchloride In methanol; water pH=1.12 - 3.70; Purification / work up;
Reaxys ID: 11649324

Reaxys ID: 11649324

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
Stage #1: With sodium methylate In methanol for 0.166667h;
Stage #2: With pyrographite In methanol
Stage #3: With hydrogenchloride In methanol; water pH=2.3 - 2.4; Purification / work up;
5-methyl-2-thiazol-2-amine
7305-71-7

5-methyl-2-thiazol-2-amine

methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
35511-15-0

methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

A

methanol
67-56-1

methanol

B

4-hydroxy-2-methyl-N-methyl-(5-methyl-2-thiazolyl)-2H-l,2-benzothiazine-3-carboxamide-1,1-dioxide

4-hydroxy-2-methyl-N-methyl-(5-methyl-2-thiazolyl)-2H-l,2-benzothiazine-3-carboxamide-1,1-dioxide

C

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
pyrographite In xylene at 170 - 180℃; for 24h; Product distribution / selectivity;
5-methyl-2-thiazol-2-amine
7305-71-7

5-methyl-2-thiazol-2-amine

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
24683-26-9

ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

A

methanol
67-56-1

methanol

B

4-hydroxy-2-methyl-N-methyl-(5-methyl-2-thiazolyl)-2H-l,2-benzothiazine-3-carboxamide-1,1-dioxide

4-hydroxy-2-methyl-N-methyl-(5-methyl-2-thiazolyl)-2H-l,2-benzothiazine-3-carboxamide-1,1-dioxide

C

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
pyrographite In xylene at 170 - 180℃; for 24h; Product distribution / selectivity;
5-methyl-2-thiazol-2-amine
7305-71-7

5-methyl-2-thiazol-2-amine

methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
35511-15-0

methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

A

N-[3,5-dimethyl-1,3-thiazol-2(3H)-ylidene]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide
1145656-36-5

N-[3,5-dimethyl-1,3-thiazol-2(3H)-ylidene]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

B

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
With methane In 5,5-dimethyl-1,3-cyclohexadiene at 138 - 142℃; for 24h; Inert atmosphere; Large scale reaction;
ethene
74-85-1

ethene

meloxicam
71125-38-7

meloxicam

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; [(2)H6]acetone
(S)-Malic acid
97-67-6

(S)-Malic acid

meloxicam
71125-38-7

meloxicam

meloxicam:L-malic acid

meloxicam:L-malic acid

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

meloxicam
71125-38-7

meloxicam

meloxicam glutaric acid
1246227-11-1

meloxicam glutaric acid

Conditions
ConditionsYield
In chloroform for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
meloxicam
71125-38-7

meloxicam

maleic acid
110-16-7

maleic acid

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide maleic acid (1:1)
1174325-93-9

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide maleic acid (1:1)

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
In ethyl acetate for 19h; Solvent;
In tetrahydrofuran at 20℃; for 24h;
meloxicam
71125-38-7

meloxicam

benzoic acid
65-85-0

benzoic acid

meloxicam benzoic acid
1174325-83-7

meloxicam benzoic acid

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
Stage #1: meloxicam; benzoic acid for 0.25h; Milling;
Stage #2: In acetone
In tetrahydrofuran at 20℃; for 0.5h; Solvent; Milling;
glycolic Acid
79-14-1

glycolic Acid

meloxicam
71125-38-7

meloxicam

meloxicam glycolic acid
1174325-97-3

meloxicam glycolic acid

Conditions
ConditionsYield
In chloroform for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
malonic acid
141-82-2

malonic acid

meloxicam
71125-38-7

meloxicam

meloxicam malonic acid
1174325-96-2

meloxicam malonic acid

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
succinic acid
110-15-6

succinic acid

meloxicam
71125-38-7

meloxicam

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide succinic acid (2:1)

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide succinic acid (2:1)

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
Stage #1: succinic acid; meloxicam for 0.25h; Milling;
Stage #2: In acetone Solvent;
In ethyl acetate at 30℃; Solvent;
Adipic acid
124-04-9

Adipic acid

meloxicam
71125-38-7

meloxicam

meloxicam:adipic acid

meloxicam:adipic acid

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
Stage #1: Adipic acid; meloxicam for 0.25h; Milling;
Stage #2: In acetone Solvent;
2,5-dihydroxybenzoic acid.
490-79-9

2,5-dihydroxybenzoic acid.

meloxicam
71125-38-7

meloxicam

meloxicam gentisic acid
1174325-98-4

meloxicam gentisic acid

Conditions
ConditionsYield
for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
meloxicam
71125-38-7

meloxicam

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

meloxicam 4-hydroxybenzoic acid
1174325-95-1

meloxicam 4-hydroxybenzoic acid

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran
malic acid
617-48-1

malic acid

meloxicam
71125-38-7

meloxicam

meloxicam:DL-malic acid

meloxicam:DL-malic acid

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
meloxicam
71125-38-7

meloxicam

salicylic acid
69-72-7

salicylic acid

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide salicylic acid (1:1)
1174325-91-7

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide salicylic acid (1:1)

Conditions
ConditionsYield
In ethyl acetate for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
Stage #1: meloxicam; salicylic acid for 0.25h; Milling;
Stage #2: In acetone
meloxicam
71125-38-7

meloxicam

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

meloxicam hydrocinnamic acid
1174326-03-4

meloxicam hydrocinnamic acid

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran
meloxicam
71125-38-7

meloxicam

1-hydroxy-2-naphthoic acid
86-48-6

1-hydroxy-2-naphthoic acid

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 1-hydroxy-2-naphthoic acid (1:1)
1174325-92-8

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 1-hydroxy-2-naphthoic acid (1:1)

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
In tetrahydrofuran Product distribution / selectivity;
In dimethylsulfoxide-d6; water at 25 - 90℃; Solvent;71 g
D-(+)-camphoric acid
124-83-4

D-(+)-camphoric acid

meloxicam
71125-38-7

meloxicam

meloxicam (+)-camphoric acid
1246227-13-3

meloxicam (+)-camphoric acid

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
meloxicam
71125-38-7

meloxicam

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

C4H4O4*2C14H13N3O4S2

C4H4O4*2C14H13N3O4S2

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;100%
1-deoxy-1-(methylamino)-D-glucitol
6284-40-8

1-deoxy-1-(methylamino)-D-glucitol

meloxicam
71125-38-7

meloxicam

N-methylglucamine salt of meloxicam
244241-52-9

N-methylglucamine salt of meloxicam

Conditions
ConditionsYield
In ethanol at 60℃; for 0.5h;93%
meloxicam
71125-38-7

meloxicam

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, acetic acid solvate

4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, acetic acid solvate

Conditions
ConditionsYield
With acetic acid92%
D-(+)-camphoric acid
124-83-4

D-(+)-camphoric acid

meloxicam
71125-38-7

meloxicam

meloxicam:(+)-camphoric acid

meloxicam:(+)-camphoric acid

Conditions
ConditionsYield
In chloroform at 20℃;91%
In tetrahydrofuran Product distribution / selectivity;
methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide
35511-15-0

methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

meloxicam
71125-38-7

meloxicam

5-methyl-2-thiazol-2-amine
7305-71-7

5-methyl-2-thiazol-2-amine

Conditions
ConditionsYield
With montmorillonite MK10 impregnated with ZnCl2 In o-xylene for 24h; Reagent/catalyst; Reflux; Green chemistry;90%
iron(II) acetate tetrahydrate

iron(II) acetate tetrahydrate

meloxicam
71125-38-7

meloxicam

[bis(4-oxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide)iron(II)] tetrahydrate

[bis(4-oxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide)iron(II)] tetrahydrate

Conditions
ConditionsYield
In methanol N2, mixed a hot solns., refluxed for 0.5 h; ppt. filtered, washed (hot methanol under N2), dried (vac., room temp.);elem. anal.;88%
[osmium(II)dichloride(η6-p-cymene)]2

[osmium(II)dichloride(η6-p-cymene)]2

meloxicam
71125-38-7

meloxicam

dichlorido(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-λ'6-benzo[e][1,2]thiazine-3-carboxylic acid(5-methyl-thiazol-2-yl)amide)(η6-p-cymene)osmium(II)

dichlorido(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-λ'6-benzo[e][1,2]thiazine-3-carboxylic acid(5-methyl-thiazol-2-yl)amide)(η6-p-cymene)osmium(II)

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h; Inert atmosphere;81%
ethanol
64-17-5

ethanol

zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

meloxicam
71125-38-7

meloxicam

trans-[Zn(Hmel)2(EtOH)2]

trans-[Zn(Hmel)2(EtOH)2]

Conditions
ConditionsYield
for 2h; Reflux;80%
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

meloxicam
71125-38-7

meloxicam

dichlorido(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-λ'6-benzo[e][1,2]thiazine-3-carboxylic acid(5-methyl-thiazol-2-yl)amide)(η6-p-cymene)ruthenium(II)

dichlorido(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-λ'6-benzo[e][1,2]thiazine-3-carboxylic acid(5-methyl-thiazol-2-yl)amide)(η6-p-cymene)ruthenium(II)

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h; Inert atmosphere;80%
copper(II) choride dihydrate

copper(II) choride dihydrate

meloxicam
71125-38-7

meloxicam

[Cu(meloxicam)2]

[Cu(meloxicam)2]

Conditions
ConditionsYield
In ethanol for 24h; Reflux;79%
di-μ-bromo-bis[bromo(η(6)-para-cymene)ruthenium(II)]
90591-13-2

di-μ-bromo-bis[bromo(η(6)-para-cymene)ruthenium(II)]

meloxicam
71125-38-7

meloxicam

bromido(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-λ'6-benzo[e][1,2]thiazine-3-carboxylic acid(5-methyl-thiazol-2-yl)amide)(η6-p-cymene)ruthenium(II)

bromido(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-λ'6-benzo[e][1,2]thiazine-3-carboxylic acid(5-methyl-thiazol-2-yl)amide)(η6-p-cymene)ruthenium(II)

Conditions
ConditionsYield
Stage #1: meloxicam With sodium methylate In methanol at 20℃; for 0.5h;
Stage #2: di-μ-bromo-bis[bromo(η(6)-para-cymene)ruthenium(II)] In methanol at 20℃; for 4h;
79%

71125-38-7Relevant articles and documents

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

Mezei, Tibor,Mesterhazy, Norbert,Bako, Tibor,Porcs-Makkay, Marta,Simig, Gyula,Volk, Balazs

, p. 567 - 572 (2009)

An improved procedure for the manufacture of 4-hydroxy-2- methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (meloxicam) is described. The key intermediate of this protocol is the new potassium salt monohydrate of meloxicam, which makes possible the efficient removal of impurities, resulting in an environmentally friendly manufacturing process of the high-purity (>99.90%) drug substance.

Process for the Purification of Meloxicam

-

Page/Page column 2, (2008/12/05)

A process for purifying meloxicam form I from a crude meloxicam, which comprises: i. contacting the crude meloxicam with an amine in a non-aqueous solvent to form a meloxicam salt;ii. isolating the meloxicam salt;iii. dissolving the meloxicam salt in an aqueous solvent to form a salt solution; andiv. adding an acid to the salt solution to precipitate free meloxicam.

Process for the purification of meloxicam

-

Page/Page column 3; 4, (2008/06/13)

The present invention relates to a process for the purification of meloxicam and in particular of the impurity composed of 4-hydroxy-2-methyl-N-ethyl-N′-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide and to meloxicam containing a quantity of less than 0.05% of the above-mentioned impurity (“ethylamide”).

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