- 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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- Synthetic method of fexofenadine intermediate
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The invention provides a synthetic method of a fexofenadine intermediate 2-[4-[4-[4-(hydroxybenzhydryl)-1-piperidyl]-butyryl]phenyl]-2- methylmethacrylate. The method comprises the following steps: methylation of phenylacetonitrile which is used as a raw material, basic hydrolysis, weinreb amidation reaction, Friedel-crafts reaction, acid hydrolysis, esterification and condensation. The method has the following advantages: raw materials and auxiliary materials are cheap and easily available; yield is high; cost is low; there is no meta-isomer; and the method is suitable for industrial production.
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- INTERMEDIATES USEFUL FOR THE SYNTHESIS OF FEXOFENADINE, PROCESSES FOR THEIR PREPARATION AND FOR THE PREPARATION OF FEXOFENADINE
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Intermediates useful for the synthesis of fexofenadine, processes for their preparation and processes for the synthesis of fexofenadine are described.
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Paragraph 0121
(2013/09/26)
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- A process for producing 4-(4-halo-1-oxybutyl)-alpha,alpha-dimethylbenzene acetic acid or alkyl esters thereof
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Disclosed herein is a process for large scale production of pure 4-(4-halo-1-oxybutyl)-α,α-dimethylbenzene acetic acid or alkyl esters thereof, wherein the process comprises of condensing (2-halo-1,1-dimethyl-ethyl)benzene with acetate salt followed by acylation with ω-halo compound, hydrolyzing and cyclizing the resultant regioisomers, subsequently oxidizing and purifying to obtain pure regioisomer, further halogenating and/or esterifying the para regioisomer to produce 4-(4-halo-1-oxybutyl)-α,α-dimethylbenzene acetic acid or their alkyl esters.
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Page/Page column 8
(2011/04/14)
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- PROCESS FOR PREPARING FEXOFENADINE
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A process for preparing fexofenadine is described, comprising the purification of 4-[4-chloro-l-oxobutyl]-2,2-dimethylphenyl acetic acid alkyl ester by means of suspension in a hydrocarbon, preferably n-heptane. The compound thus obtained is dissolved in a suitable solvent and condensed with azacyclanol to give the compound shown below (I) where R is an alkyl radical, which is then hydrolysed and reduced to give fexofenadine.
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Page/Page column 4
(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 4; 7; 11
(2008/06/13)
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- Process for production of carebastine
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Processes are disclosed for preparing piperidine derivative compounds of the formulae I, II or III:
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Page/Page column 12; 21
(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 9; 14
(2008/06/13)
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- FEXOFENADINE POLYMORPHS AND PROCESSES OF PREPARING THE SAME
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Anhydrous crystalline fexofenadine hydrochloride Form C, crystalline fexofenadine acetate monohydrate Form D, crystalline fexofenadine acetate dihydrate Form E and crystalline fexofenadine free base monohydrate Form F, processes of preparing the same, pharmaceutical compositions thereof, therapeutic uses thereof and methods of treatment therewith.
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Page/Page column 26
(2008/06/13)
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- Intermediates useful for the preparation of antihistaminic piperidine derivatives
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The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula whereinW represents —C(=O)— or —CH(OH)—;R1 represents hydrogen or hydroxy;R2 represents hydrogen;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;m is an integer 0 or 1;R3 is —COOH or —COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched each of A is hydrogen or hydroxy; andpharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R1 and R2 are taken together to form a second bond between the carbon atoms bearing R1 and R2 or where R1 represented hydroxy, m is an integer 0.
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Page column 78
(2008/06/13)
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- Intermediates useful for the preparation of antihistaminic piperidine derivatives
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The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula whereinW represents —C(=O)— or —CH(OH)—;R1 represents hydrogen or hydroxy;R2 represents hydrogen;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;m is an integer 0 or 1;R3 is —COOH or —COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched each of A is hydrogen or hydroxy; and pharmaceutically acceptable salts and individual optical isomers thereof,with the proviso that where R1 and R2 are taken together to form a second bond between the carbon atoms bearing R1 and R2 or where R1 represented hydroxy, m is an integer 0.
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Page column 78
(2010/01/30)
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- Intermediates useful for the preparation of antihistaminic piperidine derivatives
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The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula wherein W represents —C(═O)— or —CH(OH)—; R1represents hydrogen or hydroxy; R2represents hydrogen; R1and R2taken together form a second bond between the carbon atoms bearing R1and R2; n is an integer of from 1 to 5; m is an integer 0 or 1; R3is —COOH or —COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; each of A is hydrogen or hydroxy; and pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R1and R2are taken together to form a second bond between the carbon atoms bearing R1and R2or where R1represented hydroxy, m is an integer 0.
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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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