- Preparation method of fexofenadine
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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.
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- METHODS AND COMPOSITIONS FOR TREATING INFECTION
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Provided herein are compositions and methods for treating or preventing infection.
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Paragraph 0210; 0241
(2015/09/28)
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- Repurposing the antihistamine terfenadine for antimicrobial activity against staphylococcus aureus
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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.
- Perlmutter, Jessamyn I.,Forbes, Lauren T.,Krysan, Damian J.,Ebsworth-Mojica, Katherine,Colquhoun, Jennifer M.,Wang, Jenna L.,Dunman, Paul M.,Flaherty, Daniel P.
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p. 8540 - 8562
(2014/12/11)
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- PREPARATION OF 2-(4-BROMOPHENYL)-2-METHYLPROPANOIC ACID
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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.
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- Preparation of 2-(4-bromophenyl)-2-methylpropanoic acid
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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.
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- PROCESS FOR PREPARING FEXOFENADINE
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A process for preparing fexofenadine is described, which provides for the hydrolysis of 4-[4-[4-(hydroxydiphenylmethyl)-l-piperidyl]-l-oxobutyl]-α,α- dimethylbenzeneacetic acid-alkyl ester, in a mixture of water and optionally an organic solvent, in the presence of a base; the carboxylate salt of 4- [4- [4- (hydroxydiphenylmethyl)- 1 -piperidyl] - 1 -oxobutyl] -α,α -dimethylbenzeneacetic acid is thus obtained, which is directly reduced as carboxylate in a basic environment with hydrogen in the presence of a suitable hydrogenation catalyst to give the carboxylate of fexofenadine, which is precipitated by neutralisation of the solution.
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Page/Page column 5-6
(2008/06/13)
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- INDUSTRIAL PROCESS OF FEXOFENADINE HYDROCHLORIDE WITH CONTROLLED SIDE PRODUCTS
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The present invention relates to a process for the preparation of Anhydrous Fexofenadine Hydrochloride with controlled level of side products. Another aspect of the present invention is purification of Fexofenadine base free of meta isomer of fexofenadine base and fexofenadinone.
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Page/Page column 8; 12
(2008/06/13)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF HIGHLY PURE FEXOFENADINE
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The present invention provides an improved process for the preparation of highly pure 4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-butyl]-α,α-dimethylbenzene acetic acid (fexofenadine) of Formula (I), or its salts thereof.
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Page/Page column 7-8
(2008/06/13)
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- INTERMEDIATES USEFUL FOR THE PREPARATION OF ANTIHISTAMINIC PIPERIDINE DERIVATIVE
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The present invention relates to process for preparing antihistaminic piperidine derivative, specifically fexofenadine and its pharmaceutically acceptable salts by using novel synthetic intermediates of following formula (I), wherein R is lower alkyl; R2 is H, cyclopropyl, R1is alkyl, 4-(hydroxy-dipheτiyl-methyl)-piperidin-l-yl.
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Page/Page column 15
(2008/06/13)
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- Process for production of piperidine derivatives
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Processes are disclosed for preparing piperidine derivative compounds of the formulae I, II or III: The processes involve reacting a compound of formula Ia, IIa or IIIa with isobutyrate or an isobutyrate equivalent.
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Page/Page column 8; 10; 12; 14
(2008/06/13)
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- Combination of dehydroepiandrosterone or dehydroepiandrosterone-sulfate with an antihistamine for treatment of asthma or chronic obstructive pulmonary disease
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A pharmaceutical or veterinary composition, comprises a first active agent selected from a dehydroepiandrosterone and/or dehydroepiandrosterone-sulfate, or a salt thereof, and a second active agent comprising an antihistamine for the treatment of asthma, chronic obstructive pulmonary disease, or any other respiratory disease. The composition is provided in various formulations and in the form of a kit. The products of this patent are applied to the prophylaxis and treatment of asthma, chronic obstructive pulmonary disease, or any other respiratory disease.
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- Combination of dehydroepiandrosterone or dehydroepiandrosterone-sulfate with an antihistamine for treatment of asthma or chronic obstructive pulmonary disease
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A pharmaceutical or veterinary composition, comprises a first active agent selected from a dehydroepiandrosterone and/or dehydroepiandrosterone-sulfate, or a salt thereof, and a second active agent comprising an antihistamine for the treatment of asthma, chronic obstructive pulmonary disease, or other respiratory diseases. The composition is provided in various formulations and in the form of a kit. The products of this patent are applied to the prophylaxis and treatment of asthma, chronic obstructive pulmonary disease, or other respiratory diseases.
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- PROCESS FOR THE PREPARATION OF FEXOFENADINE
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The invention relates to highly pure fexofenadine and a process for preparing highly pure fexofenadine. The invention also relates to pharmaceutical compositions that include the highly pure fexofenadine and use of said compositions for treating a patient
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- METHOD OF PREPARATION OF TERFENADINE AND ITS DERIVATIVES
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The invention relates to a new method of preparation of derivatives of piperidinyl butylphenylacetic acids. The compounds are histaminically active. The substances are prepared by Grignard reaction of alkylhalohydrins and suitably substituted aromatic aldehydes. The resulting diols are subjected to subsequent substitution reaction.
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- Process for the production of piperidine derivatives
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The present invention relates to processes for preparing certain piperidine derivatives, including fexofenadine (F), the active ingredient in the non-sedating antihistamine sold in the U.S. under the designation “Allegra”. This invention also relates to novel synthetic intermediates useful in the processes of the present invention.
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- Process for the production of piperidine derivatives with microorganisms
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The present invention relates to the production of a product compound having a structure according to Formulae IA and/or IB: wherein n is 0 or 1; R1is hydrogen or hydroxy; R2is hydrogen; or, when n is 0, R1and R2taken together form a second bond between the carbon atoms bearing R1and R2, provided that when n is 1, R1and R2are each hydrogen; R3is —COOH or —COOR4; R4is an alkyl or aryl moiety; A, B, and D are the substituents of their rings, each of which may be different or the same, and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, and alkoxy. This process involves incubating a starting compound having a structure according to Formulae IIA and/or IIB: wherein R3is —CH3and R1, R2, A, B, and D are defined above In the presence of a microorganism under conditions effective to produce the product compound. The microorganism can be from the genus Streptomyces, Stemphylium, Gliocladium, Bacillus, Botrytis, Cyathus, Rhizopus, Pycniodosphora, Psuedomonas, Helicostylum, Aspergillus, Mucor, Gelasinospora, Rhodotorula, Candida, Mycobacterium, or Pennicillium. Alternatively, the microorganism can beCunninghamella bainieri.
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- Process for the production of piperidine derivatives with microorganisms
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The present invention relates to the production of a product compound having a structure according to Formulae IA and/or IB: wherein n is 0 or 1; R1 is hydrogen or hydroxy; R2 is hydrogen; or, when n is 0, R1 and R2 taken together form a second bond between the carbon atoms bearing R1 and R2, provided that when n is 1, R1 and R2 are each hydrogen; R3 is —COOH or —COOR4; R4 is an alkyl or aryl moiety; A, B, and D are the substituents of their rings, each of which may be different or the same, and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, and alkoxy. This process involves incubating a starting compound having a structure according to Formulae IIA and/or IIB: wherein R3 is —CH3 and R1, R2, A, B, and D are defined above. in the presence of a microorganism under conditions effective to produce the product compound. The microorganism can be from the genus Streptomyces, Stemphylium, Gliocladium, Bacillus, Botrytis, Cyathus, Rhizopus, Pycniodosphora, Psuedomonas, Helicostylum, Aspergillus, Mucor, Gelasinospora, Rhodotorula, Candida, Mycobacterium, or Pennicillium. Alternatively, the microorganism can be Cunninghamella bainieri.
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- A process for the preparation of 4-[1-hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-butyl]-alpha, alpha-dimethylbenzeneacetic acid
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A process for the preparation of 4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-butyl]-α,α-dimethylbenzeneacetic acid (Fexofenadine) of formula
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- Process for production of piperidine derivatives
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The present invention relates to a method for preparing piperidine derivative compounds by converting, with a piperidine compound, regioisomers having the formula: and where m is an integer from 1 to 6; Q and Y are the same or different and are selected from the group consisting of O, S, and NR5; G1, G2, and G3 are the same or different and are selected from the group consisting of OR8, SR8, and NR8R9; R6 and R7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR8, SR8, and NR8R9; X3 is halogen, OR15, SR15, NR15R16, OSO2R15, or NHSO2R15; R5, R8, R9, R15, and R16 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety; and A is a substituent of its ring and is selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents.
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- Process for production of piperidine derivatives
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The present invention relates to a method for preparing piperidine derivative compounds by converting, with a piperidine compound, regioisomers having the formula: where Z is -CG1G2G3, and where m is an integer from 1 to 6; Q and Y are the same or different and are selected from the group consisting of O, S, and NR5; G1, G2, and G3 are the same or different and are selected from the group consisting of OR8, SR8, and NR8R9; and R5, R8, and R9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety.
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- A new synthesis of carboxyterfenadine (fexofenadine) and its bioisosteric tetrazole analogs
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A new synthesis of carboxyterfenadine (4), based on the conversion of a α-halo-alkylarylketone into the corresponding substituted 2-arylalkanoic ester, is described. The enantioselective synthesis of its two bioisosteric tetrazole analogs together with preliminary biological results are reported. Copyright (C) 1999 Elsevier Science S.A.
- Di Giacomo, Barbara,Coletta, Donato,Natalini, Benedetto,Ni, Ming-Hong,Pellicciari, Roberto
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p. 600 - 610
(2007/10/03)
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- PIPERIDINE DERIVATIVES
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The present invention relates to substantially pure piperidine derivative compounds of the formulae: STR1 wherein R 1 is hydrogen or hydroxy;R 2 is hydrogen;or R 1 and R 2 taken together form a second bond between the carbon atoms bearing R 1 and R 2 ;R 3 is--COOH or--COOR 4 ;R 4 has 1 to 6 carbon atoms; A, B, and D are the substituents of their respective rings each of which may be different or the same and are hydrogen, halogens, alkyl, hydroxy, alkoxy, or other substituents. A process of preparing such piperidine derivative compounds in substantially pure form is also disclosed.
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- PIPERIDINE DERIVATIVES
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Novel compounds of the following formula: wherein R1 is hydrogen or hydroxy; R2 is hydrogen; or R1 and R2 taken together form a second bond between the carbon atoms bearing R1 and R2; n is an integer of from 1 to 5; R3 is -CH3, -CH2OH, -COOH or-COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; and each of A and B is hydrogen or hydroxy; with the provisos that at least one of A or B is hydrogen and one of A or B is other than hydrogen when R3 is -CH3; and pharmaceutically acceptable salts thereof
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