139965-11-0

Usage

Uses

Used in Pharmaceutical Industry:
S-FEXOFENADINE is used as an active pharmaceutical ingredient for treating allergic conditions such as seasonal allergies, hives, and itching. It functions by acting as an H1-histamine receptor antagonist, which helps to alleviate the symptoms associated with these conditions.
Used in Research and Development:
S-FEXOFENADINE is also used as a research compound in the field of pharmaceuticals and biochemistry. It serves as a valuable tool for studying the mechanisms of histamine action and the development of new drugs targeting histamine receptors.
Used in Drug Formulation:
In the drug formulation industry, S-FEXOFENADINE is used as a key component in the development of various dosage forms, such as tablets, capsules, and oral solutions, to provide relief from allergic symptoms.
Used in Quality Control:
S-FEXOFENADINE is utilized in the quality control of pharmaceutical products to ensure the presence, potency, and purity of the active ingredient in the final product. This helps to maintain the safety and efficacy of the medication for patients.

Upstream product

• 169280-30-2 N-methoxy-N-methyl-2-(4-{1-hydroxy-4-[4-(hydroxy-diphenylmethyl)-piperidine-1-yl]-butyryl}-phenyl)-isobutyramide 
• 1319714-86-7 fexofenadine sodium salt 
• 50679-08-8 terfenadine 
• 185066-40-4 4-(4'-(hydroxy(diphenyl)methyl)piperidin-1-yl)-1-(4-isopropylphenyl)butan-1-one 
• 98-82-8 Isopropylbenzene 
• 1313731-46-2 tert-butyl(4-(4-(hydroxyldiphenylmethyl)piperidin-1-yl)-1-(4-isopropylphenyl)butan-1-oxy)dimethylsilane 
• 1313731-47-3 tert-butyl(4-(4-(hydroxyldiphenylmethyl)piperidin-1-yl)-1-(4-(2-bromopropan-2-yl)phenyl)butan-1-oxy)dimethylsilane 
• 70289-38-2 4-Chloro-1-(4-isopropyl-phenyl)-butan-1-one 
• 162096-54-0 2-(4-cyclopropanecarbonyl-phenyl)-2-methyl-propionic acid 
• 76811-97-7 4-(4-chloro-1-oxobutyl)-α,α-dimethylbenzeneacetic acid ethyl ester 
• 169280-26-6 2-(4-(1-Oxo-1-cyclopropanyl)-phenyl)-2-methylpropanol 
• 2901-13-5 ethyl 2-methyl-2-phenylpropionate 
• 1448311-89-4 4-(4-chloro-1-hydroxyl-butyl)-α,α-dimethyl phenyl acetic acid ethyl ester 
• 4559-96-0 1-(4-bromophenyl)-4-chlorobutan-1-one 

Relevant academic research and scientific papers

Microbial oxidation of terfenadine and ebastine into fexofenadine and carebastine

Fexofenadine 5 and carebastine 6 were obtained in good yield by optimization of culture conditions of microorganisms. Oxidation of 1 into 9 was observed as described in mammalian metabolism. The oxidation of tert-butyl-phenyl group of title compounds by s

Preparation method of fexofenadine

The invention provides a preparation method of fexofenadine, which comprises the following steps: by using bromobenzene as a raw material, carrying out Friedel-Crafts acylation reaction to obtain 4'-bromo-4-chlorophenone ; enabling 4'-bromo-4-chlorobutanone and 1-methoxy-1-(trimethylsiloxy)-2-methyl-1-propene to subjected to coupling reaction to obtain 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methyl methyl propionate; and sequentially carrying out N-alkylation, carbonyl reduction and alkaline hydrolysis on 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methylpropanoate to obtain fexofenadine. The method has the advantages of cheap and easily available raw materials, easiness in operation, high yield, low cost, no meta-isomer, suitability for industrial production and the like.

A fexofenadine and method for synthesizing intermediate

The invention relates to a simple and efficient synthetic method of fexofenadine (chemical name: 4-{1-hydroxyl-4-[4-(hydroxyl benzhydryl)-1-piperidyl]-butyl}-alpha, alpha-dimethyl-phenylacetic acid (I)) and its intermediate. According to the method, isopropyl benzene is used as a raw material. Through a Friedel-Crafts acylation reaction, a halogenation reaction and a carbonyl insertion reaction, a key intermediate 4-(4-chloro-1-butyryl)-alpha, alpha-dimethyl phenylacetic acid (IV) is obtained; the key intermediate reacts with another raw material dibenzyl-(4-pyridyl)-methanol (E) to obtain a key pyridinium intermediate 4-{4-chloro-[4-hydroxydiphenylmethyl]-1-pyridinium]-1-butyryl}-alpha, alpha-dimethyl phenylacetic acid (V); and through catalytic hydrogenation and metallic hydrogen reduction, high-purity fexofenadine is obtained. The synthetic method provided by the invention has advantages of smooth process, simple reaction, short route, convenient post-treatment, high yield and low cost, and is a very ideal preparation method of fexofenadine and industrialization feasible route.

A fexofenadine hydrochloride process for synthesizing

The invention discloses a synthetic process of fexofenadine hydrochloride. The synthetic process of fexofenadine hydrochloride comprises the following steps of: with alpha, alpha-dimethyl phenylacetic acid as a raw material, carrying out an esterification reaction on alpha, alpha-dimethyl phenylacetic acid and absolute ethyl alcohol under the catalysis of a silica gel loaded phosphotungstic acid (PW12/SiO2) solid acid catalyst to obtain alpha, alpha-dimethyl ethyl phenylacetate; carrying out Friedel-Grafts reaction on alpha, alpha-dimethyl ethyl phenylacetate and 4-chlorobutyryl chloride to obtain alpha, alpha-dimethyl-4-(4-chloro-1-oxo butyl) ethyl phenylacetate; reducing by virtue of sodium borohydride in 95% ethyl alcohol to obtain alpha, alpha-dimethyl-4-(4-chloro-1-hydroxyl butyl) ethyl phenylacetate; and carrying out N-alkylation reaction on alpha, alpha-dimethyl-4-(4-chloro-1-hydroxyl butyl) ethyl phenylacetate and alpha, alpha-dimethyl-4-piperidine methyl alcohol in DMF (dimethyl formamide) for 24 hours at the temperature of 80 DEG C to obtain alpha, alpha-dimethyl-4-[1-hydroxyl-4-[4-(hydroxyl diphenylmethyl)-1-piperidyl]-butyl] ethyl phenylacetate, and then carrying out alkali hydrolysis and salification by virtue of hydrochloric acid, so that fexofenadine hydrochloride is obtained. The synthetic process of fexofenadine hydrochloride is high in yield and low in cost, produces less pollution and is applicable to industrial mass production.

METHODS AND COMPOSITIONS FOR TREATING INFECTION

Provided herein are compositions and methods for treating or preventing infection.

Repurposing the antihistamine terfenadine for antimicrobial activity against staphylococcus aureus

Staphylococcus aureus is a rapidly growing health threat in the U.S., with resistance to several commonly prescribed treatments. A high-throughput screen identified the antihistamine terfenadine to possess, previously unreported, antimicrobial activity against S. aureus and other Gram-positive bacteria. In an effort to repurpose this drug, structure-activity relationship studies yielded 84 terfenadine-based analogues with several modifications providing increased activity versus S. aureus and other bacterial pathogens, including Mycobacterium tuberculosis. Mechanism of action studies revealed these compounds to exert their antibacterial effects, at least in part, through inhibition of the bacterial type II topoisomerases. This scaffold suffers from hERG liabilities which were not remedied through this round of optimization; however, given the overall improvement in activity of the set, terfenadine-based analogues provide a novel structural class of antimicrobial compounds with potential for further characterization as part of the continuing process to meet the current need for new antibiotics.

INTERMEDIATES USEFUL FOR THE SYNTHESIS OF FEXOFENADINE, PROCESSES FOR THEIR PREPARATION AND FOR THE PREPARATION OF FEXOFENADINE

Intermediates useful for the synthesis of fexofenadine, processes for their preparation and processes for the synthesis of fexofenadine are described.

The synthesis of fexofenadine

This work proposes a new simple route for fexofenadine synthesis with low cost and easily obtainable raw materials. We use benzene and methallyl as starting reactants, applying steps of Friedel-Crafts alkylation reaction, hydrolysis, oxidation, esterification reaction, and reduction reaction to obtain the intermediate product, followed by N-alkylation reaction to obtain 4-{1-hydroxy-4-[4-(hydroxydiphenyl)-piperidine]butyl}-α, α-dimethylbenzene acetate. Then, the final product fexofenadine is obtained upon hydrolysis. In the synthesis process, we constantly optimize the reaction conditions such as reaction time, reaction temperature, solvent selection, and other factors, thus improving the final yield of the target product fexofenadine to 33.51 %.

PREPARATION OF 2-(4-BROMOPHENYL)-2-METHYLPROPANOIC ACID

Selective bromination of 2-methyl-2-phenylpropanoic acid in aqueous medium is described to obtain pure 2-(4-bromophenyl)-2-methylpropanoic acid, which is a useful key intermediate in the process of manufacturing pure fexofenadine.

Preparation of 2-(4-bromophenyl)-2-methylpropanoic acid

Selective bromination of 2-methyl-2-phenytpropanoic acid on aqueous medium is described to obtain pure 2-(4-bromophenyl)-2-methylpropanoic acid, which is a useful key intermediate in the process of manufacturing pure fexofenadine.