161715-24-8

Basic information

• Product Name: (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester
• Synonyms: (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester;Tebipenem Pivoxil;[(2,2-Dimethylpropanoyl)oxy]methyl (4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;(4R,5S,6S)-3-[[1-(4,5-Dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid (2,2-DiMethyl-1-oxopropoxy)Methyl Ester;[4R-[4α,5β,6β(R*)]]-3-[[1-(4,5-Dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-(1-hydroxyethyl)-4-Methyl-7-oxo-1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid (2,2-DiMethyl-1-oxopropoxy)Methyl Ester;OrapeneM;ME1211;TBPM-PI
• CAS NO: 161715-24-8
• Molecular Formula: C23H32N2O6S2
• Molecular Weight: 496.63998
• EINECS: 1308068-626-2
• Product Categories: API;Inhibitors
• Mol File: 161715-24-8.mol

Chemical Properties

• Melting Point: 140-142℃
• Boiling Point: 661.905 °C at 760 mmHg
• Flash Point: 354.107 °C
• Appearance: /
• Density: 1.50
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.36±0.20(Predicted)
• CAS DataBase Reference: (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester(161715-24-8)
• EPA Substance Registry System: (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester(161715-24-8)

Safety Data

• Hazardous Substances Data: 161715-24-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tebipenem Pivoxil is used as an oral carbapenem antibiotic for the treatment of various bacterial infections. Its application is based on its ability to be absorbed and metabolized into Tebipenem, its active metabolite, which demonstrates excellent bactericidal activity against resistant bacterial strains.
Used in Research and Development:
In the field of pharmaceutical research and development, Tebipenem Pivoxil serves as a valuable compound for studying the structure-activity relationships of carbapenem antibiotics. Its unique chemical structure allows scientists to explore new avenues in the design and synthesis of novel antibiotics with improved properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Drug Delivery Systems:
Similar to gallotannin, Tebipenem Pivoxil can also be incorporated into drug delivery systems to improve its bioavailability, delivery, and therapeutic outcomes. These systems can include organic and metallic nanoparticles, liposomes, or other advanced drug carriers, which can help overcome limitations associated with the compound's pharmacokinetics and pharmacodynamics.

InChI:InChI=1/C22H31N3O6S2/c1-11-15-14(12(2)26)18(27)25(15)16(19(28)30-10-31-20(29)22(3,4)5)17(11)33-13-8-24(9-13)21-23-6-7-32-21/h11-15,26H,6-10H2,1-5H3/t11-,12-,14-,15-/m1/s1

Upstream product

• 161715-21-5 Tebipenem 
• 18997-19-8 Chloromethyl pivalate 
• 179337-62-3 3-methanesulfonyloxy-1-(1,3-thiazolin-2-yl)azetidine 
• 161715-27-1 1-(1,3-thiazolin-2-yl-)azetidin-3-ol 
• 161715-28-2 3-acetylthio-1-(1,3-thiazolin-2-yl)azetidine 
• 161715-20-4 (+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-{[1-(2-thiazolin-2-yl)-3-azetidinyl]sulfanyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid-p-nitrobenzyl ester 
• 179337-57-6 1-(4,5-dihydro-1,3-thiazol-2-yl)-3-mercaptoazetidine hydrochloride 
• 682747-73-5 (4R,SR,6S)-6-[(1R)-1-hydroxyethyl]-3-diphenylphosphoryloxy-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid pivaloyloxymethyl ester 
• 692779-24-1 (4R,5R,6S)-6-[(1R)-1-trimethylsilyloxyethyl]-3-diphenylphosphoryloxy-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid pivaloyloxymethyl ester 
• 93711-81-0 (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 53064-79-2 iodomethyl pivaloate 
• 189188-38-3 MAP 

Relevant articles and documents

Preparation method of medicinal tebipenem pivoxil

The invention discloses a preparation method of medicinal tebipenem pivoxil, which comprises the following steps: taking MAP and YKTP-1 as raw materials, sequentially carrying out condensation, reduction and substitution reaction, and purifying the material after the substitution reaction twice to obtain the medicinal tebipenem pivoxil. A primary purification process comprises the following steps: adding ethyl acetate into the material after the substitution reaction, conducting filtering, adding water into the filtrate, adjusting the pH value, carrying out liquid separation to obtain a water layer, adjusting the pH value of the water layer, conducting extracting with ethyl acetate to obtain an organic layer, washing the organic layer, conducting drying, decolorizing and filtering, carrying out vacuum concentration on the filtrate, conducting crystallizing and centrifuging, leaching a filter cake with ethyl acetate, and conducting drying in vacuum to obtain YKTP-4; and a secondary purification process comprises the following steps: mixing YKTP-4 with ethyl acetate, adding activated carbon, conducting stirring, conducting filtering to obtain filtrate, concentrating the filtrate to YKTP-4 under reduced pressure, conducting crystallizing and centrifuging, leaching a filter cake with ethyl acetate, and performing vacuum drying to obtain the medicinal tebipenem pivoxil.

Preparation method of tebipenem pivoxil

The invention provides a novel preparation method of tebipenem pivoxil, and belongs to the technical field of chemical drug synthesis. Cesium carbonate is used as an acid-binding agent for the first time to introduce methyl pivalate into the construction process of tebipenem pivoxil molecules. According to the method, a cheap inorganic alkali that is the cesium carbonate is used as an acid-bindingagent, so that the use of a phase transfer catalyst and organic alkali is avoided, and the reduction of the cost of bulk drugs and the control of impurity residues are facilitated. The novel preparation process has the advantages of mild conditions, simple operation, high yield and short reaction time, and is suitable for commercial production of tebipenem pivoxil bulk drugs.

Tebipenem pivoxil and synthetic method thereof

The invention provides tebipenem pivoxil and a synthetic method thereof. The invention relates to the technical field of drug synthesis. The synthetic method comprises the three-step synthetic reactions of condensation of a main ring and a tebipenem side chain, a TB-1 hydrogenation reduction reaction, and a reaction of a TB-2 intermediate and iodomethyl pivalate. The preparation method of tebipenem pivoxil provided by the invention is simple and convenient in preparation process, suitable for industrial production, and relatively high in yield; processing operations, such as column chromatography, which are required to be adopted by traditional synthesis are eliminated; a reasonable synthetic route is designed; the reaction time is effectively shortened; the post-processing process is simplified.

Preparation method of high-purity tebipenem pivoxil crystals

The invention discloses a preparation method of high-purity tebipenem pivoxil crystals. The method comprises the following steps: adding a first solvent to crude tebipenem pivoxil, and performing stirring to obtain a primary dissolved product; adding a second solvent dropwise to the primary dissolved product at a reaction temperature, and then performing stirring for crystallization, wherein the first solvent contains water; the second solvent is acetonitrile; the reaction temperature is 0-60 DEG C. The tebipenem pivoxil crystals with high purity and low solvent residue content can be preparedwith the method.

Industrial preparation process more than the [...] method

The invention relates to the field of medical chemistry, and specifically relates to a tebipenem pivoxil industrial preparation method. The method comprises the following steps: tebipenem, a solvent I, salt, and a phase-transfer catalyst are mixed, and a salt-forming reaction is carried out under normal temperature; chloromethylpivalate is added under a same temperature, and an esterification reaction is carried out; when the reaction is finished, extraction and concentration are carried out; a solvent II is dropped for crystallization; and filtering is carried out, such that tebipenem pivoxil is obtained. With the method, operation is simple, and complicated operations of pH regulation and repeated extraction are avoided. Post-treatment solvent dose is low, such that resource is saved, and environment pollution is reduced. Chloromethylpivalate property is stable, and normal-temperature reaction requirement is low. Product yield is high, and a maximal yield can be higher than 88%. The purity of synthesized tebipenem pivoxil can be higher than 99.7%. Without refining, the obtained tebipenem pivoxil can be used for preparing medicine preparations as a raw material medicine satisfying medical requirements, and the medicine preparation can be safely used by patients. The method is suitable for industrial productions.

Preparation method of tebipenem pivoxil and intermediate thereof

The invention provides a preparation method of tebipenem pivoxil. A three-step method synthesis route taking MAP (compound 2) and TAT (compound 3) as starting raw materials is adopted. The preparation method is characterized in that in the first step, the temperature of reaction for preparing an intermediate compound 4 of the tebipenem pivoxil from the MPA and the TAT is -4 to 5 DEG C. Compared with the preparation method using the three-step method synthesis route in the prior art, the preparation method has the following advantages: the step avoids ultralow reaction temperature, so that the method is mild in reaction condition, easy to implement and suitable for industrialized production; furthermore, the reaction yield in each step is increased and the purify of reactants is improved.

PREPARATION METHOD FOR TEBIPENEM PIVOXIL

The present invention refers to reel expense lung [neym [neym] coating chamber further pore number are disclosed. According to the present invention conventional publicly known process contrast 5 times can be achieved and high yields, vacuum, the shower head includes a first reel expense lung [neym [neym] can be obtained by coating chamber diameter number. (by machine translation)

A process for the preparation of antibacterial drug

The invention discloses a preparation method of an antibacterial medicament tebipenem pivoxil. (4R,5R,6S)-3-((diphenyl-phosphoroso-carbonyl)oxyl)-6-((R)-1-ethoxyl)-4-methyl-7-carbonyl-1-azabicyclo[3.2.0]heptane-2-alkenyl-2-carboxylic acid p-nitro ester(6-MAP(I)) serving as a raw material reacts with 1-(4,5-dihydro-2-thiazolinyl)-3-sulfydryl azetidine hydrochloride (II) in the presence of alkali to obtain (4R,5S,6S)-3-((1-(4,5-dihydro-2-thiazolinyl)-3-azetidine) sulfenyl)-6-((R)-1-ethoxy)-4-methyl-7-oxygen-1-azabicyclo[3.2.0]heptane-2-alkenyl-2-carboxylic acid p-nitro ester (III); the protecting group of the compound (III) is removed under the catalytic hydrogenation condition to obtain (4R,5S,6S)-3-((1-(4,50dihydro-2-thiazolinyl)-3-azetidine)sulfenyl)-6-((R)-1-ethoxy)-4-methyl-7-oxygen-1-azabicyclo[3.2.0]heptane-2-alkenyl-2-carboxylic acid (IV); and the compound (IV) reacts with chloromethyl pivalate and sodium iodide or potassium iodide in the presence of alkali to obtain tebipenem pivoxil (V). According to the preparation method, the selected initial raw materials are low in price and easily available, so that the synthesizing route is simplified, the raw material utilization and total yield can be improved; and the intermediate substance obtained in the reaction is purified by using a re-crystallization method with high yield, less three wastes are generated in the reacting process, and the low cost is advantageous to industrial production.

Preparation method of tebipenem pivoxil

The invention provides a preparation method of tebipenem pivoxil, and relates to the technical field of pesticide synthesis. The preparation method of the tebipenem pivoxil comprises the following steps that 1-(4,5-dihydro-2-thiazolyl) azetidine-3-thiol hydrochloride and 1 beta-methyl vinyl phosphate are used as raw materials to take a reaction under the existence of diisopropylethylamine, and an acetonitrile water solution is used for washing to obtain an intermediate I; the intermediate I, an n-butyl alcohol water solution, a palladium-carbon catalyst and sodium bicarbonate take a mixed reaction, and treatment is performed to obtain an intermediate II; the intermediate II and chloromethyl pivalate take a reaction through phase transfer catalyst catalysis under the existence of diisopropylethylamine and dimethylformamide to obtain an intermediate III; the intermediate III and a sodium bicarbonate water solution are mixed, ethyl acetate is added, and reaction and refining are performed to prepare the tebipenem pivoxil. The preparation method has the advantages that the purity and the yield of the intermediates are obviously improved; the purity of the final product of the tebipenem pivoxil reaches 99.21 to 99.78 percent; the yield reaches 88.7 to 92.1 percent.

The matching fu Zhi than peinan method for the preparation of

The invention discloses a preparation method for tebipenem pivoxil shown as formula 1. The preparation method comprises the following step of performing the following reaction on a compound III and a compound IV in an organic solvent and water, with the action of (R1)3P and an organic base, under inert gas protection, wherein the volume ratio of the organic solvent and water is 1000 : 1-20 : 1; a reaction temperature is -40-50 DEG C; and R1 represents phenyl or C2-C8 alkyls. The preparation method is easy to operate, simple in post-treatment, with the product having high yield and high purity, and is suitable for industrialized production.