75007-71-5

Usage

Uses

Used in Respiratory Infections:
LISTERIA MOX SUPPLEMENT is used as an antibiotic for treating infections of the respiratory organs, such as pneumonia, bronchitis, and sinusitis, due to its effectiveness against a wide range of bacteria.
Used in Urinary Tract Infections:
LISTERIA MOX SUPPLEMENT is used as an antibiotic for treating infections of the urinal tract, such as cystitis and pyelonephritis, due to its ability to target bacteria that commonly cause these infections.
Used in Abdominal Cavity Infections:
LISTERIA MOX SUPPLEMENT is used as an antibiotic for treating infections of the abdominal cavity, such as peritonitis and intra-abdominal abscesses, due to its broad-spectrum activity against various bacteria.
Used in Gynecological Infections:
LISTERIA MOX SUPPLEMENT is used as an antibiotic for treating gynecological infections, such as pelvic inflammatory disease and endometritis, due to its effectiveness against bacteria that cause these conditions.
Used in Bone and Joint Infections:
LISTERIA MOX SUPPLEMENT is used as an antibiotic for treating infections of the bones and joints, such as osteomyelitis and septic arthritis, due to its ability to penetrate and treat infections in these areas.
Used in Skin and Soft Tissue Infections:
LISTERIA MOX SUPPLEMENT is used as an antibiotic for treating skin and soft tissue infections, such as cellulitis and wound infections, due to its effectiveness against a wide range of bacteria that cause these conditions.
Used in Gonorrhea Treatment:
LISTERIA MOX SUPPLEMENT is used as an antibiotic for treating gonorrhea, a sexually transmitted infection caused by the bacterium Neisseria gonorrhoeae, due to its effectiveness against this bacterium.

Synthesis

Moxalactam, 7β[2-carboxy-2-(4-hydroxyphenyl)acetamido]-7α-methoxy- 3-(1-methyltetrazol-5-yl)-thiomethyl-1-oxa-dethia-3-cefem-4-carboxylic acid (32.1.2.98), is synthesized in a multi-stage synthesis from 6-APA, which is acylated by benzoylchloride in the presence of triethylamine to give 6-benzoylpenicillin (32.1.2.85). The carboxyl group of LISTERIA MOX SUPPLEMENT is protected by a reaction with diphenyldiazomethane, to form the 3-diphenylmethyl ester of 6-benzoylpenicillin (32.1.2.86). Oxidation of this product with molecular chlorine under basic conditions gives the S-oxide of the 3-diphenylmethyl ester of 6-benzoylpenicillin (32.1.2.87). Upon reacting this with triphenylphosphine, the expected reduction of sulfoxide to sulfide does not occur, but rather the thiazine ring is opened, causing sulfur to be released while also resulting in its simultaneous substitution with oxygen and subsequent formation of a cyclic iminoester (32.1.2.88). Chlorinating the double bond of this product with chlorine and subsequent treatment of obtained dichloro derivative with sodium bicarbonate gives a chloromethyallyl derivative (32.1.2.89), which upon reaction with potassium iodide substitutes the chlorine with iodine, forming an iodomethylallyl derivative (32.1.2.90), and finally, hydrolyzing this product in dimethylsulfoxide in the presence of copper(I) oxide forms the corresponding allylic alcohol (32.1.2.91).Upon heating this in the presence of boron trifluoride–diethyl etherate, it recyclizes back to form an oxazine ring and the reverse transformation of the cyclic iminoester into the amide form (32.1.2.92). The exocyclic double bond of the resulting product undergoes chlorination and subsequent treatment of the product with a base using 1,7-diazabicyclo-[4.5.0]undec-6-ene (DBU), gives the 3-chloromethyl derivative (32.1.2.93). Reacting this with tert-butyl hypochlorite, obviously to make an N-chloro derivative, and then with lithium methoxide, after acidification and treatment with sodium thiosulfate gives diphenylmethyl ester of 7β-benzoylamido-7 α-methoxy-3-(chloromethylyl)-1-oxa-dethia-3-cefem-4-carboxylic acid (32.1.94). Reacting this with the sodium salt of 5-mercapto-1-methyl-tetrazol gives the diphenylmethyl ester of 7β-benzoylamido-7α-methoxy-3-(1-methyltetrazol-5-yl)-thiomethyl-1-oxa-dethia-3-cefem- 4-carboxylic acid (32.1.95). Debenzoylation of this product and subsequent treatment with phosphorous pentachloride in pyridine and then with methanol and diethylamine gives the diphenylmethyl ester of 7β-amino-7α-methoxy-3-(1-methyltetrazol-5-yl)-thiomethyl-1-oxadethia-3-cefem-4-carboxylic acid (32.1.2.96). Acylating LISTERIA MOX SUPPLEMENT with the mixed anhydride synthesized from mono-diphenylmethyl ester of (4-hydroxyphenyl)malonic acid and oxalylchloride in the presence of triethylamine gives the bis-diphenylmethyl ester protection on both carboxyl groups of the desired product (32.1.2.97). Finally, removing the indicated protecting groups from both carboxyls by boiling it with trifluoroacetic acid in toluene gives the desired moxalactam (32.1.2.98)

Upstream product

• 66510-99-4 (6R,7R)-benzhydryl-7-amino-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 64952-86-9 chlorocarbonyl-[4-(4-methoxy-benzyloxy)-phenyl]-acetic acid 4-methoxy-benzyl ester 
• 70653-54-2 C₄₁H₃₈N₆O₁₀S 
• 70653-54-2 C₄₁H₃₈N₆O₁₀S 
• 1079440-87-1 moxalactam 
• 64952-97-2 moxalactam 
• 70175-90-5 4-(4-methoxybenzyloxy)benzene malonic acid-4-methoxybenzyl monoester 

Downstream Products

• 75007-70-4 decarboxy-moxalactam 
• 1079440-87-1 moxalactam 

Relevant academic research and scientific papers

Latamoxef carboxyl and hydroxyl protection group removing method

The invention discloses a latamoxef carboxyl and hydroxyl protection group removing method, which comprises that a compound represented by the following formula I is subjected to protection group removing under the actions of hydrochloric acid and a carbo

A β - lactam compound carboxy and hydroxy protecting group removing method (by machine translation)

The invention discloses a β - lactam compound carboxyl and hydroxyl protecting group removal method, the method is that the carboxyl and/or hydroxyl protected β - lactam compounds in the trichloro acetic acid and carbon is ion absorbent for removing protecting group and gets the role of β - lactam compound deprotected product. The method adopts the trichloro acetic acid instead of trifluoro acetic acid, trichloro acetic acid and phenol or cresol and, anisole together, can greatly reduce the consumption of the trichloroacetic acid; in addition, trichloro acetic acid in the cephalosporin into sodium salt in the follow-up process meets the volunteer fire brigade into chloroform and carbon dioxide, is easy to remove, does not exist the problem of residual of the trichloroacetic acid, the reaction yield is high, relatively few impurities; trichloro acetic acid is inexpensive and environmentally friendly, reduce the cost beneficial to industrial production. (by machine translation)

Method for removing protecting group of latamoxef sodium

A compound (I) is firstly chlorinated in an organic solvent, a compound (II) is obtained and reacts with a compound (III) to produce a compound (IV), water washing purification, removal of the protecting group and water washing purification are preformed, concentration crystallization is performed finally, and a target compound (V) is obtained. The product obtained with the preparation method is high in purity, high in yield and good in color, the operation is simple, equipment investment is reduced, and energy consumption is low.

Method for preparing high-purity pulls the oxygen spore sodium

The invention discloses a preparing method for high-purity latamoxef sodium. The method comprises the steps that a compound I is subjected to a deprotection reaction in organic solvent, washed with water for impurity removal, and washed with alkali to obtain a latamoxef sodium saline solution, the latamoxef sodium saline solution is degraded for impurity removal, then acid regulating is carried out on the latamoxef sodium saline solution to prepare a latamoxef monosodium saline solution crude product, and the crude product is extracted for impurity removal to obtain a latamoxef monosodium saline solution refined product; the latamoxef monosodium saline solution refined product is acidized, and extracted with organic solvent, water is removed from an organic layer, the solvent is distilled and recovered, and crystallization is carried out to obtain refined solid latamoxef acid; alkali regulating is carried out on the refined solid latamoxef acid to obtain a sodium saline solution, and decoloration and lyophilization are carried out to obtain the high-purity latamoxef sodium. The preparing method is simple and efficient, the quality of the obtained high-purity latamoxef sodium meets the requirement of the ICH guiding principle Q3A, other special purification processes are not needed, operating steps are reduced, purification equipment investment is saved, and energy consumption is low.

Epimerization kinetics of moxalactam, its derivatives, and carbenicillin in aqueous solution

The mechanism of the epimerization of moxalactam was studied by measuring the rate of epimerization after deuteration of the C-7 side-chain chiral carbon, introduction of different substituents on the side chain, and variation of the ring system. Deuteration slowed the epimerization rate considerably. The rate was also influenced by the choice of the ring system and the substituent on the C-7 side-chain chiral carbon. When the penicillin ring system with the 2-carboxy-2-phenylacetamide was studied, the epimerization rate decreased indicating that the same ring system needed to be used throughout the epimerization studies. Thus, experiments were conducted with different substituents replacing the phenolic group at the C-7 side-chain chiral carbon of moxalactam. The epimerization rate decreased in the substituent order thienyl, phenyl, 4-hydroxyphenyl, the ionized form of 4-hydroxyphenyl, and ethyl. These results showed that dehydrogenation of the chiral carbon seems to be the rate-determining step and that the stronger the electron-donating effect of the substituent, the slower the epimerization rate becomes.

Degradation and epimerization kinetics of moxalactam in aqueous solution

The kinetics of epimerization and degradation of moxalactam in aqueous solution was investigated by HPLC. The pH-rate profiles of the degradation and epimerization were determined separately over the pH range of 1.0-11.5 at 37°C and constant ionic strength 0.5. The degradation and simultaneous epimerization were followed by measuring both of the residual R- and S-epimers of moxalactam and were found to follow pseudo-first-order kinetics. The degradation was subjected to hydrogen ion and hydroxide ion catalyses and influenced by the dissociation of the side chain phenolic group. The epimerization rates were influenced significantly in the acidic region by the dissociation of the side chain carboxylic acid group and in the basic region by hydroxide ion catalysis. The pH-degradation rate profile of moxalactam showed a minimum degradation rate constant between pH 4.0 and 6.0. The pH-epimerization rate profiles of moxalactam showed minimum epimerization rate constants at pH 7.0. The epimerization rate constant of the R- and S-epimers were not very different.

Cephalosporin analogues and compositions

Novel cephalosporin analogues, salts and esters thereof, their preparation, intermediates and antibacterial compositions containing them. The compositions are formulated for human use into unit dosage form containing 100-4,000 mg of antibacterial compound. The cephem analogues are characterized by having a ring O-heteroatom instead of a ring N-heteroatom and are designated as oxacephems.