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
• Article Data: 14

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

Description

(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, also known as Tebipenem Pivoxil, is a derivative of carbapenem antibiotics. It is a white solid with potent bactericidal activity against β-lactamase-nonproducing, ampicillin-resistant isolates. The compound is characterized by its unique stereochemistry and functional groups, which contribute to its biological activity and pharmacological properties.

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

• 18997-19-8 Chloromethyl pivalate 
• 179337-57-6 1-(4,5-dihydro-1,3-thiazol-2-yl)-3-mercaptoazetidine hydrochloride 
• 189188-38-3 MAP 
• 161715-21-5 Tebipenem 
• 53064-79-2 iodomethyl pivaloate 
• 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 
• 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 
• 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 
• 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 
• 161715-28-2 3-acetylthio-1-(1,3-thiazolin-2-yl)azetidine 
• 161715-27-1 1-(1,3-thiazolin-2-yl-)azetidin-3-ol 
• 179337-62-3 3-methanesulfonyloxy-1-(1,3-thiazolin-2-yl)azetidine 

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.

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 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.