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103577-45-3

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103577-45-3 Usage

Brief Introduction

Lansoprazole is in a class of drugs called proton pump inhibitors (PPI) which prevent the stomach from producing gastric acid.The other drugs in PPI family include: rabeprazole (Aciphex), omeprazole (Prilosec), pantoprazole (Protonix), esomeprazole (Nexium). Proton pump inhibitors are used for the treatment of conditions such as ulcers, gastroesophageal reflux disease (GERD) and Zollinger-Ellison syndrome that are caused by stomach acid. Lansoprazole, like other proton-pump inhibitors, blocks the enzyme in the wall of the stomach that produces acid. By blocking the enzyme, the production of acid is decreased, and this allows the stomach and esophagus to heal.

Uses

Different sources of media describe the Uses of 103577-45-3 differently. You can refer to the following data:
1. Lansoprazole is a proton pump inhibitor (PPI) similar to omeprazole that inactivates the hydrogen/potassium-stimulated ATPase pumps in parietal cells, thus inhibiting gastric acid secretion and increasing intragastric pH. It is a potent inhibitor of gastric acidity which is widely used in the therapy of gastroesophageal reflux and peptic ulcer disease. Lansoprazole is a racemic mixture of (R)- and (S)-isomers. Dexlansoprazole is an isomer of lansoprazole that has a similar spectrum of activity and toxicities. Lansoprazole therapy is associated with a low rate of transient and asymptomatic serum aminotransferase elevations and is a reported, but very rare cause of clinically apparent liver injury. Lansoprazole's plasma elimination half-life is not proportional to the duration of the drug's effects (i. e. gastric acid suppression). The plasma elimination half-life is 1. 5 hours or less, and the effects of the drug last for over 24 hours after it has been given for 5 days or more. Lansoprazole is a prescription medicine used to treat: gastroesophageal reflux disease (GERD) erosive esophagitis stomach ulcers duodenal ulcers H. Pylori infections Zollinger-Ellison syndrome
2. A H+,K+-ATPase inhibitor that displays antisecretory activity
3. Treatment of gastroesophageal reflux disease (GERD), erosive esophagitis, duodenal ulcers, Helicobacter pylori (H. pylori) infections,stomach ulcers, prevention of stomach ulcers in those people taking non-steroidal anti-inflammatory drugs (NSAIDs), such
4. For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
5. Used as a gastric proton pump inhibitor. An antiulcerative

Gastric acid secretion inhibitor

R-(+)-Lansoprazole is the dextroisomer of lansoprazole and a kind of anti-ulcer drug. It is the substitution product of benzimidazole derivative byimporting the fluorine element in the molecular structure and the is the second proton pump inhibitor after omeprazole.? R-(+)-Lansoprazole has a better inhibitory effect for gastric acid secretion than that of other drugs (omeprazole, pantoprazole, rabeprazole) and it can significantly inhibit ulcer. It has a better Curative effect for ethanol-induced gastric mucosa lesion and acid hypersecretion induced duodenal ulcer than that of famotidine and omeprazole. In addition, This product also has an anti-Helicobacter pylori effect similar to that of Bismuth preparations and can be used to treat reflux esophagitis and Zollinger-Ellison syndrome. pharmacodynamics??? R-(+)-Lansoprazole can transform into active sulfonamide derivatives. In the tubule acidic environment of parietal cells, which are connected to the sulfydryl of H+-K+-(ATP)adenosine triphosphatase(the last step of the enzyme catalyzed gastric acid secretion process),passivat H+-K+-ATP enzyme and Inhibit the gastric acid secretion regulated by central and peripheral nervous systems. The inhibition effect of gastric acid secretion of this product is at least as strong as omeprazole. In vivo studies of animal model have demonstrated that the inhibition effect for gastric acid secretion of R-(+)-Lansoprazole is inferior to H2 receptor antagonist ranitidine and famotidine, but just as effective as omeprazole. Unlike the H2 receptor antagonist, whether taken in the morning or evening, this product can inhibit gastric acid secretion during the day and night. It can also reduce the gastric acid secretion, inhibit the secretion of pepsin and its activity and clear pyloric campylobacter on gastric mucosa (A bacterium of causing recurrence. of peptic ulcer). It can also be used to treat Helicobacter pylori infection, alongside antibiotics as adjunctive treatment, to kill H. pylori causing ulcers or other problems involves using two other drugs known as "triple therapy", and involves taking twice daily for 10 or 14 days lansoprazole, amoxicillin, and clarithromycin.

Pharmacokinetics

When this product transform into active AG-1812 and AG-2000, R-(+)-Lansoprazole in serum is metabolized quickly and completely into two main faeces: Lansoprazole sulfone and hydroxy orchid sola. About 14%~23% of doses are excreted in the urine as conjugated and non-conjugated hydroxylation metabolites and no prototype of this product is found. The half-life of this product is 1.3~1.7 h, about 2 h for elderly people and as long as 7 h for patients with severe liver failure. The Peak blood concentration can reach 1038μg/L within 2 h after taking 30 mg enteric capsules of this product.

Marketing internationally

The lansoprazole molecule is off-patent and so generic drugs are available under many brand names in many countries;there are patents covering some formulations in effect as of 2015. Since 2009, lansoprazole has been sold over the counter (OTC) in the U.S. in a marketed by Novartis as Prevacid 24HR. In Australia, it is being marketed by Pfizer as Zoton.

Clinical application

Applied to reflux esophagitis, gastric ulcer, duodenal ulcer. Patients with duodenal ulcer take this product 30 mg a day for a period of 2~4 weeks. An cure efficiency rate of 75%~100% can be achieved.It cures faster than famotidine and omeprazole and reduces ulcers-induced pain faster thanranitidine. Taking this product 30 mg a day can effectively treat reflux esophagitis and the cure rates after 4 weeks and 8 weeks can reach? 63%~84% and 85%~92% respectively. The cure effect for reflux esophagitis of this product is better than ranitidine and comparative to omeprazole. After 4 weeks treatment, the alleviation effect for heartburn symptoms of this product is much better than that of ranitidine and omeprazole. R-(+)-Lansoprazole can effectively treat patients with Peptic ulcer and reflux esophagitis whom cannot be cured by H2 receptor antagonist. A cure rate of 69%~100% can be achieved by taking this product 30 mg a day for a period of 8 weeks. A higher cure rate can be achieved if the dosage is increased to 30mg a day.

Drug interactions

1. Take R-(+)-Lansoprazole in conjunction with acetaminophen can increase the Peak blood concentration and shorten the time to peak. 2. Take R-(+)-Lansoprazole in conjunction with Roxithromycin can increase the local concentration of the latter and has a synergistic effect when treating Hp infection. 3. Take R-(+)-Lansoprazole in conjunction with antacids can reduce the bioavailability of this product. If necessary, this product should be taken after 1 hour use of antacids. 4. Take R-(+)-Lansoprazole in conjunction with theophylline can slightly reduce the? blood concentrations of theophylline. 5. R-(+)-Lansoprazole can inhibit gastric acid secretion significantly and persistently, thereby reduce the absorption of itraconazole and ketoconazole. So they should not be used at the same time. 6. Sucralfate may interfere the absorption of this product and reduce its bioavailability. So this product should be taken at least 30 minutes before taking sucralfate. 7. Take R-(+)-Lansoprazole in conjunction with clarithromycin may cause? Glossitis, stomatitis and black tongue. Patients should pay attention to the change of oral mucosa , stop using clarithromycin and reduce the dose of this product if necessary.

Adverse reactions

This product can cause constipation, diarrhea, dry mouth, abdominal distention, anemia, increased white blood cells and eosinophils, thrombocytopenia, elevated liver enzymes, headache, drowsiness, insomnia, skin rashes, itching, etc., and occasionally cause fever, increased total cholesterol and uric acid value, etc.

Cautions

1.This drug is forbidden for those who are allergic to this product, pregnant and lactant women. Patients with a history of drug allergy and hepatic insufficiency should use this product with caution. 2.Elderly patients with medication must be closely observed 3.This product may mask the stomach cancer symptoms. Therefore, this product should be taken before excluding stomach cancer.

Description

Different sources of media describe the Description of 103577-45-3 differently. You can refer to the following data:
1. Lansoprazole is a proton pump inhibitor that inhibits the H+/K+-ATPase. It inhibits K+ and H+ accumulation in gastric microsomes in a concentration-dependent manner (IC50s = 6.3 and 7.0 μM, respectively) and inhibits H+/K+-ATPase activity by approximately 60% when used at a concentration of 10 μM. Lansoprazole inhibits the H+/K+-ATPase in parietal cells, thus inhibiting gastric acid secretion and increasing intragastric pH. It is a substituted benzimidazole that binds covalently to proton pumps, providing complete and prolonged inhibition of acid secretion. Formulations containing lansoprazole have been used as a proton pump inhibitor and in combination with antibiotics in the treatment of H. pylori infections and duodenal ulcer disease.
2. Lansoprazole is the second proton pump inhibitor approved as an antiulcer agent for the short term treatment of duodenal ulcer and gastroesophageal reflux disease. Like omeprazole, lansoprazole is reported to be more efficacious than the H2-antagonists in treating peptic ulcer disease.Other potential uses could be in the treatment of Zollinger-Ellison syndrome.

Chemical Properties

White Crystalline Powder

Originator

Takeda (Japan)

Manufacturing Process

Preparation of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methylthio-1Hbenzimidazole:A mixture of 6.63 g of 2-hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy) pyridine (30 mmol), 4.5 g of 2-mercaptobenzimidazol (30 mmol) and 8.67 g of triphenylphosphine (33 mmol) was dissolved in 100 ml of tetrahydrofuran, 5.75 g of diethyl azodicarboxylate (33 mmol) dissolved in 30 ml of tetrahydrofuran was added dropwise thereto at room temperature, and stirred for 1 hour. The reaction mixture was concentrated under a reduced pressure, the resulting residue was combined with 100 ml of ethylacetate, and extracted twice with 50 ml portions of 1 N HCl. The aqueous layer was then washed with 50 ml of diethylether; neutralized with 1 N NaOH to adjust the pH to 7. The resulting precipitates were filtrated, washed with water, and dried, to obtain 10.06 g of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methylthio- 1H-benzimidazole as a white solid (yield: 95%), m.p.142-144°C.4.46 g of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methylthio-1Hbenzimidazole (12 mmol) and 18.74 mg of tetramethyl-1-piperidinyloxy free radical (1 mol %, used as a catalyst) were dissolved in 40 ml of tetrahydrofuran, and combined with 166.76 mg of tetrabutylammonium chloride (5 mol %) dissolved in 20 ml of distilled water. The resulting mixture was cooled to 0°C and 13.6 ml of NaOCl (12%, 2.2 equivalent) dissolved in 20 ml of distilled water was added thereto over 2 hours at 0°C, stirred for 10 min, and then for additional 10 min at 20°C. Then, the reaction mixture was extracted with 40 ml of ethylacetate and the organic layer was washed with sat. NaHCO3 (30 ml) and then with sat. brine (30 ml), dried over anhydrous MgSO4, and the solvent was removed therefrom. The resulting crude product as recrystallized from acetone/hexane, to obtain 3.99 g of 2-[3-methyl-4- (2,2,2-trifluoroethoxy)-2-pyridyl]methylsulphinyl-1H-benzimidazol (lansoprazole) as a white-light brown solid (yield: 90%), melting point 164- 165°C (decomposition).

Brand name

Prevacid (TAP);Ogast;Lanzor.

Therapeutic Function

Antiulcer

General Description

Lansoprazole, 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole(Prevacid), is a white to brownish white, odorless crystallinepowder that is practically insoluble in water.Lansoprazole is a weak base (pyridine N, pKa 3.83.) and aweak acid (benzimidazole N-H, pK 0.62). Like other PPIs,lansoprazole is essentially a prodrug that, in the acidic biophaseof the parietal cell, forms an active metabolite thatirreversibly interacts with the target ATPase of the pump.Lansoprazole must be formulated as encapsulated entericcoatedgranules for oral administration to protect the drugfrom the acidic environment of the stomach.In the fasting state, about 80% of a dose of lansoprazole(vs. 50% of omeprazole) reaches the systemic circulation,where it is 97% bound to plasma proteins. Thedrug is metabolized in the liver (sulfone and hydroxymetabolites) and excreted in bile and urine, with a plasmahalf-life of about 1.5 hours.

Biological Activity

H + ,K + -ATPase inhibitor (IC 50 = 6.3 μ M) that displays antisecretory and antiulcer activity. Inhibits gastric acid secretion (IC 50 = 0.09 μ M for histamine-induced acid formation) and reduces gastric lesion formation induced by a variety of ulcerative stimuli. Antibacterial against Helicobacter pylori in vitro . Also blocks swelling-dependent chloride channel (ICIswell) in NIH3T3 fibroblasts. More potent than omeprazole (5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole ).

Biochem/physiol Actions

Gastric proton pump inhibitor.

Check Digit Verification of cas no

The CAS Registry Mumber 103577-45-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,3,5,7 and 7 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 103577-45:
(8*1)+(7*0)+(6*3)+(5*5)+(4*7)+(3*7)+(2*4)+(1*5)=113
113 % 10 = 3
So 103577-45-3 is a valid CAS Registry Number.
InChI:InChI=1/C17H14F3N3O2/c1-10-13(21-7-6-15(10)25-9-17(18,19)20)8-14(24)16-22-11-4-2-3-5-12(11)23-16/h2-7H,8-9H2,1H3,(H,22,23)

103577-45-3 Well-known Company Product Price

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

  • (L0233)  Lansoprazole  >98.0%(HPLC)(T)

  • 103577-45-3

  • 1g

  • 690.00CNY

  • Detail
  • TCI America

  • (L0233)  Lansoprazole  >98.0%(HPLC)(T)

  • 103577-45-3

  • 5g

  • 1,850.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000773)  Lansoprazole  European Pharmacopoeia (EP) Reference Standard

  • 103577-45-3

  • Y0000773

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000774)  Lansoprazole for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 103577-45-3

  • Y0000774

  • 1,880.19CNY

  • Detail
  • USP

  • (1356916)  Lansoprazole  United States Pharmacopeia (USP) Reference Standard

  • 103577-45-3

  • 1356916-150MG

  • 4,662.45CNY

  • Detail
  • Sigma

  • (L8533)  Lansoprazole  ≥98% (TLC), powder

  • 103577-45-3

  • L8533-250MG

  • 565.11CNY

  • Detail
  • Sigma

  • (L8533)  Lansoprazole  ≥98% (TLC), powder

  • 103577-45-3

  • L8533-1G

  • 1,786.59CNY

  • Detail

103577-45-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name lansoprazole

1.2 Other means of identification

Product number -
Other names Lanz

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:103577-45-3 SDS

103577-45-3Synthetic route

lansoprazole sulfide
103577-40-8

lansoprazole sulfide

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With 2C5H8N2*VO2F; dihydrogen peroxide In ethanol at 10 - 15℃; for 2h; Temperature; Industrial scale;100%
With dihydrogen peroxide; methyltrioxorhenium(VII) In 2,2,2-trifluoroethanol; water at 0℃; for 1h; Product distribution / selectivity;98%
With magnesium monoperoxyphthalate hexahydrate In ethanol; water at -20 - -10℃; for 4h;95%
3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride

3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride

Benzimidazol-2-thiol
134469-07-1

Benzimidazol-2-thiol

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
Stage #1: 3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride; Benzimidazol-2-thiol With carboxy chlorine; sodium carbonate In methanol at 64℃; for 3h;
Stage #2: With titanium(IV) isopropylate In water; toluene at 28 - 55℃; for 1.83333h; Temperature; Solvent; Reagent/catalyst; Further stages;
98%
lansoprazole hydrate acetonitrile solvate

lansoprazole hydrate acetonitrile solvate

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With ammonia In water; acetonitrile at 0 - 40℃; for 3.5h; Product distribution / selectivity;95.2%
With ammonia In water; acetone at 30 - 35℃; Product distribution / selectivity;79%
In water at 15 - 30℃; Product distribution / selectivity;
lansoprazole sulphide hydrate

lansoprazole sulphide hydrate

water ethanol
180330-54-5

water ethanol

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With dihydrogen peroxide; sodium thiosulfate In vanadium(V) oxide; dichloromethane; tert-butyl alcohol93.2%
With dihydrogen peroxide; sodium thiosulfate In vanadium(V) oxide; dichloromethane; tert-butyl alcohol93.2%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In ethanol; chloroform
iansoprazole ethanol hydrate
207790-96-3

iansoprazole ethanol hydrate

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
In water at 40℃; Product distribution / selectivity;93%
With triethylamine In water; acetonitrile at 35℃; Product distribution / selectivity;92%
In water; acetonitrile at 35℃; Product distribution / selectivity;92%
2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-1,4-dihydropyridin-2-yl]methyl}sulfinyl)-1H-benzimidazole

2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-1,4-dihydropyridin-2-yl]methyl}sulfinyl)-1H-benzimidazole

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In toluene at 0 - 10℃; for 9h; Solvent; Reagent/catalyst; Temperature;93%
2-[(RS)-[(4-chloro-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole

2-[(RS)-[(4-chloro-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole

2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

sodium 2,2,2-trifluoroethanolate
420-87-1

sodium 2,2,2-trifluoroethanolate

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
In dimethyl sulfoxide at 90 - 100℃; Solvent; Large scale;92.1%
lansoprazole sulphide hydrate

lansoprazole sulphide hydrate

Vanadium(IV) acetylacetonate

Vanadium(IV) acetylacetonate

water ethanol
180330-54-5

water ethanol

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With dihydrogen peroxide; sodium thiosulfate In ethanol91%
With dihydrogen peroxide; sodium thiosulfate In ethanol91%
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

2-(((4-nitro-3-methyl-2-pyridyl)methyl)sulfinyl)benzimidazole

2-(((4-nitro-3-methyl-2-pyridyl)methyl)sulfinyl)benzimidazole

sodium 2,2,2-trifluoroethanolate
420-87-1

sodium 2,2,2-trifluoroethanolate

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
In dimethyl sulfoxide at 90 - 100℃; Solvent; Large scale;90.8%
sodium vanadate

sodium vanadate

lansoprazole sulphide hydrate

lansoprazole sulphide hydrate

water ethanol
180330-54-5

water ethanol

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With dihydrogen peroxide; sodium thiosulfate In ethanol90.5%
With dihydrogen peroxide; sodium thiosulfate In ethanol90.5%
vanadium(V) oxide
788133-24-4

vanadium(V) oxide

lansoprazole sulphide hydrate

lansoprazole sulphide hydrate

water ethanol
180330-54-5

water ethanol

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With dihydrogen peroxide; sodium thiosulfate In ethanol89.5%
With dihydrogen peroxide; sodium thiosulfate In ethanol89.5%
2-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]thio]-1H-benzimidazole
666727-70-4

2-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]thio]-1H-benzimidazole

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
Stage #1: 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]thio]-1H-benzimidazole With tert.-butylhydroperoxide; vanadium(III) 2,4-pentanedionate In ethanol at 5℃; for 6h;
Stage #2: With ammonia; sodium sulfite In ethanol; water at 25℃; for 17h; pH=8 - 8.5;
85%
lansoprazole sulfide
103577-40-8

lansoprazole sulfide

A

lansoprasole
103577-45-3

lansoprasole

B

Lansoprazole sulfone

Lansoprazole sulfone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; vanadium acetyl acetonate In ethanol at 5℃; for 4h; Purification / work up;A 79%
B 0.3%
Stage #1: lansoprazole sulfide With tert.-butylhydroperoxide; vanadium acetyl acetonate In ethanol at 5℃; for 6h;
Stage #2: With ammonium hydroxide In water at 25℃; for 17h; pH=8 - 8.5; Purification / work up; Alkaline aqueous solution;
A n/a
B 0.15%
aqueous sodium metabisulphate

aqueous sodium metabisulphate

(acac)2

(acac)2

aqueous tert-butyl hydroperoxide (TBHP)

aqueous tert-butyl hydroperoxide (TBHP)

lansoprazole sulfide
103577-40-8

lansoprazole sulfide

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
In ethanol79%
2-[[(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole
163119-30-0

2-[[(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
sodium(hydrogen ethylenediaminetetraacetato)ruthenium(III)Cl} In ethanol; water at 50℃; for 1h;50%
{Ru[(EDTA)H]Cl}Na In ethanol; water at 50℃; for 1h;50%
2,3-dimethyl-4-nitropyridine N-oxide
37699-43-7

2,3-dimethyl-4-nitropyridine N-oxide

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 94 percent / tert-BuOK / 42 h / 50 - 60 °C
2: 1) Ac2O, conc. H2SO4, 2) aq. NaOH / 1) 100-120 deg C, 5 h, 2) MeOH, rt, 3 h
3: 1) SOCl2, 2) MeONa / 1) CHCl3, reflux, 20 min, 2) MeOH, reflux, 1 h
4: 45 percent / m-chloroperbenzoic acid / CHCl3 / ice-cooling
View Scheme
2-Hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine
103577-66-8

2-Hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) SOCl2, 2) MeONa / 1) CHCl3, reflux, 20 min, 2) MeOH, reflux, 1 h
2: 45 percent / m-chloroperbenzoic acid / CHCl3 / ice-cooling
View Scheme
Multi-step reaction with 3 steps
1: Triphenylphosphine oxide; bis(trichloromethyl) carbonate / toluene / 6 h / 20 - 60 °C
2: sodium hydroxide / ethanol / 2 h / Reflux
3: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 0.5 h / -5 - 20 °C
View Scheme
2,3-dimethyl-4-(2,2,2-trifluoroethoxy)-pyridine N-oxide
103577-61-3

2,3-dimethyl-4-(2,2,2-trifluoroethoxy)-pyridine N-oxide

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) Ac2O, conc. H2SO4, 2) aq. NaOH / 1) 100-120 deg C, 5 h, 2) MeOH, rt, 3 h
2: 1) SOCl2, 2) MeONa / 1) CHCl3, reflux, 20 min, 2) MeOH, reflux, 1 h
3: 45 percent / m-chloroperbenzoic acid / CHCl3 / ice-cooling
View Scheme
Diethyl tartrate
408332-88-7

Diethyl tartrate

lansoprazole sulfide
103577-40-8

lansoprazole sulfide

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; ethyl acetate
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene
lansoprazole sulphide hydrate

lansoprazole sulphide hydrate

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With urea hydrogen peroxide adduct; vanadium(V) oxytrifluoride In 1-methyl-pyrrolidin-2-one at 0 - 20℃; Product distribution / selectivity;
Tri-n-octylamine
1116-76-3

Tri-n-octylamine

Diethyl tartrate
408332-88-7

Diethyl tartrate

lansoprazole sulfide
103577-40-8

lansoprazole sulfide

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene
dimethyl tartrate
405897-14-5

dimethyl tartrate

lansoprazole sulfide
103577-40-8

lansoprazole sulfide

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene
dibutyl tartrate
344268-32-2

dibutyl tartrate

lansoprazole sulfide
103577-40-8

lansoprazole sulfide

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

lansoprazole sulfide
103577-40-8

lansoprazole sulfide

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene0.63 g (29%)
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

(R)-2-(4-methanesulfonyl-3-methyl-pyridin-2-ylmethanesulfinyl)-1H-benzimidazole

(R)-2-(4-methanesulfonyl-3-methyl-pyridin-2-ylmethanesulfinyl)-1H-benzimidazole

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
Stage #1: 2,2,2-trifluoroethanol With potassium tert-butylate In N,N-dimethyl-formamide at 25 - 30℃;
Stage #2: (R)-2-(4-methanesulfonyl-3-methyl-pyridin-2-ylmethanesulfinyl)-1H-benzimidazole In N,N-dimethyl-formamide at 25 - 30℃; for 24h;
Stage #3: With acetic acid In water; N,N-dimethyl-formamide at 0 - 10℃; pH=7.0 - 7.5;
C26H28F3N3O5S2

C26H28F3N3O5S2

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
Stage #1: C26H28F3N3O5S2 With sodium hydroxide In methanol; water at 30℃; for 0.916667h;
Stage #2: With acetic acid pH=7;
(S)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

(S)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethyl acetate at 5 - 10℃; for 0.5h;
(R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole (R)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

(R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole (R)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethyl acetate at 5 - 10℃; for 0.5h;
2-(chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine
128430-66-0

2-(chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine

Benzimidazol-2-thiol
134469-07-1

Benzimidazol-2-thiol

lansoprasole
103577-45-3

lansoprasole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / Flow reactor
2: sodium hypochlorite; sodium hydroxide / water; acetonitrile / Flow reactor; Large scale
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide / 1,2-dimethoxyethane / 8 h / 50 °C
2: 3-chloro-benzenecarboperoxoic acid / chloroform / 0 °C
View Scheme
2-[p-(chlorosulfonyl)phenoxy]acetamide
69986-21-6

2-[p-(chlorosulfonyl)phenoxy]acetamide

lansoprasole
103577-45-3

lansoprasole

2-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)acetamide
259183-34-1

2-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)acetamide

Conditions
ConditionsYield
Inert atmosphere; Basic conditions;96%
With triethylamine In dichloromethane
choline chloride
67-48-1

choline chloride

lansoprasole
103577-45-3

lansoprasole

2-[3-methyl-4-(2,2,2-trifluoroethoxy)-pyridin-2-ylmethanesulfinyl]-1H-benzoimidazole choline salt

2-[3-methyl-4-(2,2,2-trifluoroethoxy)-pyridin-2-ylmethanesulfinyl]-1H-benzoimidazole choline salt

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; for 24h;94%
(4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester
651728-13-1

(4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester

lansoprasole
103577-45-3

lansoprasole

(4-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester

(4-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester

Conditions
ConditionsYield
With sodium hydride; sodium hydrogencarbonate In dichloromethane at 20℃;94%
Stage #1: lansoprasole With sodium hydride In dichloromethane at 20℃; Inert atmosphere;
Stage #2: (4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester With sodium hydrogencarbonate In dichloromethane Inert atmosphere;
94%
6-[2-(4-chlorosulfonyl-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester
651728-35-7

6-[2-(4-chlorosulfonyl-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester

lansoprasole
103577-45-3

lansoprasole

6-[2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester

6-[2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester

Conditions
ConditionsYield
With sodium hydride In dichloromethane at 20℃; for 2h;94%
2-[p-(chlorosulfonyl)phenoxy]-N-(2-pyridyl)acetamide
259183-87-4

2-[p-(chlorosulfonyl)phenoxy]-N-(2-pyridyl)acetamide

lansoprasole
103577-45-3

lansoprasole

2-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}-phenoxy)-N-(2-pyridyl)acetamide
259183-03-4

2-(4-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}-phenoxy)-N-(2-pyridyl)acetamide

Conditions
ConditionsYield
Inert atmosphere; Basic conditions;94%
With triethylamine In dichloromethane
2-(4-chlorosulfonylphenoxy)butyric acid 2-(toluene-4-sulfonyl)ethyl ester
651728-20-0

2-(4-chlorosulfonylphenoxy)butyric acid 2-(toluene-4-sulfonyl)ethyl ester

lansoprasole
103577-45-3

lansoprasole

2-(4-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]benzoimidazole-1-sulfonyl}phenoxy)butyric acid 2-(toluene-4-sulfonyl)ethyl ester

2-(4-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]benzoimidazole-1-sulfonyl}phenoxy)butyric acid 2-(toluene-4-sulfonyl)ethyl ester

Conditions
ConditionsYield
With sodium hydride In dichloromethane at 20℃; for 2h;93%
Stage #1: lansoprasole With sodium hydride In dichloromethane at 20℃; Inert atmosphere;
Stage #2: 2-(4-chlorosulfonylphenoxy)butyric acid 2-(toluene-4-sulfonyl)ethyl ester In dichloromethane at 20℃; Inert atmosphere;
93%
neodymium(III) nitrate hexahydrate

neodymium(III) nitrate hexahydrate

lansoprasole
103577-45-3

lansoprasole

uracil
66-22-8

uracil

[Nd2([[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-yl]methyl]sulfinyl]-1H-benzimidazole)(uracil)·4H2O]NO4·nH2O

[Nd2([[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-yl]methyl]sulfinyl]-1H-benzimidazole)(uracil)·4H2O]NO4·nH2O

Conditions
ConditionsYield
In ethanol; water at 80℃;93%
(R)-1,1'-Bi-2-naphthol
18531-94-7

(R)-1,1'-Bi-2-naphthol

lansoprasole
103577-45-3

lansoprasole

(R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole R-(+)-2,2'-dihydroxy-1,1'-binaphthyl

(R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole R-(+)-2,2'-dihydroxy-1,1'-binaphthyl

Conditions
ConditionsYield
In dichloromethane at 20 - 40℃; Resolution of racemate;92.55%
In dichloromethane at 20 - 40℃;92.55%
In dichloromethane at 20 - 40℃;92.55%
lansoprasole
103577-45-3

lansoprasole

copper(II) sulfate
7758-99-8

copper(II) sulfate

C16H14F3N3O2S*Cu(2+)*2C5H5N5*(x)H2O*O4S(2-)

C16H14F3N3O2S*Cu(2+)*2C5H5N5*(x)H2O*O4S(2-)

Conditions
ConditionsYield
In ethanol; water Reflux;89%
3-chlorosulfonylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester
651728-72-2

3-chlorosulfonylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester

lansoprasole
103577-45-3

lansoprasole

2-[(4-methylphenyl)sulfonyl]ethyl 3-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)(2-pyridyl)]methyl}sulfinyl)benzimidazolyl]sulfonyl}benzoate

2-[(4-methylphenyl)sulfonyl]ethyl 3-{[2-({[3-methyl-4-(2,2,2-trifluoroethoxy)(2-pyridyl)]methyl}sulfinyl)benzimidazolyl]sulfonyl}benzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h;87%
chromium sulfate

chromium sulfate

lansoprasole
103577-45-3

lansoprasole

C16H14F3N3O2S*Cr(2+)*(x)H2O*O4S(2-)*2C5H5N5

C16H14F3N3O2S*Cr(2+)*(x)H2O*O4S(2-)*2C5H5N5

Conditions
ConditionsYield
In ethanol; water Reflux;87%
cobalt(II) sulfate

cobalt(II) sulfate

lansoprasole
103577-45-3

lansoprasole

C16H14F3N3O2S*Co(2+)*(x)H2O*O4S(2-)*2C5H5N5

C16H14F3N3O2S*Co(2+)*(x)H2O*O4S(2-)*2C5H5N5

Conditions
ConditionsYield
In ethanol; water Reflux;83%
[2-(morpholin-4-yl)ethoxy]benzene-4-sulfonyl chloride
259183-84-1

[2-(morpholin-4-yl)ethoxy]benzene-4-sulfonyl chloride

lansoprasole
103577-45-3

lansoprasole

1-[{2-(morpholin-4-yl)ethoxy}phenyl-4-sulfonyl]-2-[(3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl)methylsulfinyl]-1H-benzimidazole
259183-38-5

1-[{2-(morpholin-4-yl)ethoxy}phenyl-4-sulfonyl]-2-[(3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl)methylsulfinyl]-1H-benzimidazole

Conditions
ConditionsYield
Inert atmosphere; Basic conditions;82%
With sodium hydrogencarbonate; triethylamine; sodium chloride In dichloromethane
manganese(II) sulfate

manganese(II) sulfate

lansoprasole
103577-45-3

lansoprasole

C16H14F3N3O2S*Mn(2+)*(x)H2O*O4S(2-)*2C5H5N5

C16H14F3N3O2S*Mn(2+)*(x)H2O*O4S(2-)*2C5H5N5

Conditions
ConditionsYield
In ethanol; water Reflux;82%
3-chlorosulfonylbenzoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester
651728-08-4

3-chlorosulfonylbenzoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester

lansoprasole
103577-45-3

lansoprasole

3-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]benzimidazole-1-sulfon-yl}benzoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester

3-{2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]benzimidazole-1-sulfon-yl}benzoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester

Conditions
ConditionsYield
With sodium hydride In dichloromethane at 20℃; for 2h;80%
Stage #1: lansoprasole With sodium hydride In dichloromethane at 20℃; Inert atmosphere;
Stage #2: 3-chlorosulfonylbenzoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester In dichloromethane at 20℃; for 2h; Inert atmosphere;
80%
4-(4-chlorosulfonyl-3-isopropylphenoxyactamido)butyric acid 2-(3-nitrobenzenesulfonyl)ethyl ester
651728-46-0

4-(4-chlorosulfonyl-3-isopropylphenoxyactamido)butyric acid 2-(3-nitrobenzenesulfonyl)ethyl ester

lansoprasole
103577-45-3

lansoprasole

4-[2-(3-isopropyl-4-{-2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetylamino]butyric acid 2-(3-nitrobenzenesulfonyl)ethyl ester

4-[2-(3-isopropyl-4-{-2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetylamino]butyric acid 2-(3-nitrobenzenesulfonyl)ethyl ester

Conditions
ConditionsYield
With sodium hydride In dichloromethane at 20℃; for 2h;80%
3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride

3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride

lansoprasole
103577-45-3

lansoprasole

1-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole
1083100-26-8

1-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole

Conditions
ConditionsYield
With sodium hydroxide In water Heating;80%

103577-45-3Relevant articles and documents

Synthesis method of lansoprazole

-

Paragraph 0047-0075, (2021/04/28)

The invention discloses a synthesis method of lansoprazole, which comprises the following steps: condensing 2-mercaptobenzimidazole and 2-chloromethyl-3-methyl-4-(2, 2, 2-trifluoroethoxy) pyridine hydrochloride under alkaline conditions, oxidizing by a one-pot method to obtain a lansoprazole crude product, and finally refining to obtain the lansoprazole refined product. The method solves the problems that many three wastes are generated in lansoprazole production, a plurality of refining is needed, and drying deterioration is easily caused; the method is mild in reaction conditions, the total molar yield is 92% or above, the HPLC is 99.9% or above, and the method is suitable for industrial large-scale production.

Stable high-purity (R)-Lansoprazole, and preparation method thereof

-

Paragraph 0056-0058, (2019/09/14)

The invention provides (R)-Lansoprazole with a purity of 99.5% or higher. The preparation method comprises following steps: a (R)-Lansoprazole crude product is dissolved in a refined solvent system, dissolving and condensation are carried out, and then crystallization, filtering, and impurity removing are carried out to obtain refined (R)-Lansoprazole, wherein in the dissolving preparation process, an alkaline stabilizing agent 1 is added, and in the condensation process, an alkaline stabilizing agent 2 is added, so that the impurity I content of the obtained (R)-Lansoprazole refined product is lower than 0.1%, degradation impurity introduction is controlled preferably, in long term storage process, the obtained product is capable of satisfying medicine purity requirements, the controllability is high, and a quality control problem of (R)-Lansoprazole in industrialized production is solved.

Method for preparing benzimidazole proton pump inhibitor

-

Paragraph 0049; 0050; 0051; 0053; 0054; 0055; 0056-0058, (2018/09/08)

The invention provides a novel method for preparing a benzimidazole proton pump inhibitor, and belongs to the field of medicine synthesis. According to the method provided by the invention, a complexformed by using graphene oxide and a transition metal salt is used as a catalyst, and the corresponding benzimidazole proton pump inhibitor is obtained through oxidizing a thioether by an oxidizing agent under an alkaline condition in an organic solvent. The method has the advantages of mild reaction condition, high yield, environmental friendliness, and less impurity, the catalyst can be recycled, and the method is suitable for industrial production.

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