- 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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Paragraph 0077-0079
(2021/04/17)
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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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Paragraph 0010; 0051; 0052; 0053; 0054; 0055
(2017/02/28)
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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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- 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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- 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 0106
(2013/09/26)
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- Process for Preparing Fexofenadine
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A process for preparing fexofenadine is described that includes the purification of 4-[4-chloro-1-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 where R is an alkyl radical, which is then hydrolysed and reduced to give fexofenadine.
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Page/Page column 2
(2010/02/17)
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- PROCESS FOR THE PREPARATION OF KETO INTERMEDIATES
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Process for the preparation of 4-[1-oxo-4-[4-(hydroxyphenylmethyl)-1-piperidinyl]butyl]-α,α-dimethylbenzenacetic acid, which is an intermediate useful in the preparation of fexofenadine, by hydrating asymmetric alkynes.
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Page/Page column 3
(2010/09/17)
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- PROCESS FOR PREPARATION OF 4-[4-(4-(HYDROXYDIPHENYLMETHYL)- 1-PIPERIDINYL]-1-OXOBUTYL]-α,α-DIMETHYLBENZENE ACETIC ACID METHYL ESTER AND USE THEREOF
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The present invention provides an improved process for preparing fexofenadine, its pharmaceutically acceptable salts and solvates thereof, the process comprising reacting methyl-4-(4-halo-1-oxobutyl]-α,α-dimethylphenyl acetate with α,α-diphenyl-4-piperidinemethanol in an alkyl nitrile solvent to prepare 4-[4-(4- (hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α,-dimethylbenzene acetic acid alkyl ester, which is further converted into fexofenadine.
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Page/Page column 8
(2010/01/29)
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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 4-5
(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 4-5; 7; 11
(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 14-15: 18
(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; 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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- 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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- 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 98-99
(2010/01/30)
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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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- 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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- 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)-; 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 ta to form a second bond between the carbon R1 and R2 or where R1 represented hydroxy 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: 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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- 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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Pharmaceutically useful compounds of the following formula: STR1 wherein R1 represents hydrogen or hydroxy; R2 represents hydrogen; or R1 and R2 taken together form a second bond between the carbon atoms bearing R1 and R2 ; n is a positive whole integer of from 1 to 5; R3 is --CH3, --CH2 OH, --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; and A and B are individually 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 acid addition salts thereof.
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