- A synthesis process of cetirizine hydrochloride
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A new technology for synthesizing cetirizine hydrochloride. The technology includes following steps: oxidizing hydroxyzine, which is used as a raw material, into a substance containing an aldehyde group; further oxidizing the substance containing the aldehyde group into cetirizine; and finally performing a salification and purification process to obtain the cetirizine hydrochloride. A total yield of the synthetic method is higher than 80%. Meanwhile, the method is simple in operation, is short in production period, is low in energy consumption and cost, is little in waste water, waste gas and residues and is suitable for large-scale industrial production.
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Paragraph 0074; 0075; 0076; 0077
(2017/03/08)
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- New manufacturing procedure of cetirizine
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A new procedure for the manufacture of cetirizine dihydrochloride via the new intermediate 2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)- N,N-dimethylacetamide dihydrochloride, synthesized by O-alkylation of 2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethanol with 2-chloro-N,N-dimethylacetamide, is elaborated. Hydrolysis of the resulting amide and subsequent salification provided cetirizine dihydrochloride.
- Reiter, Jozsef,Trinka, Peter,Bartha, Ferenc L.,Pongo, Laszlo,Volk, Balazs,Simig, Gyula
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p. 1279 - 1282
(2012/09/08)
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- Process for obtaining cetirizine dihydrochloride
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Process for the synthesis of cetirizine dihydrochloride, wherein (a) a solution of {2-[4-(α-phenyl-p-chlorobenzyl)piperazin-1-yl]}ethanol in 1-7 volumes, referred to the weight of {2-[4-(α-phenyl-p-chlorobenzyl)piperazin-1-yl]}ethanol, of an organic solvent having a boiling point higher than 90° C. and being chosen from the group consisting of aliphatic, cycloalifatic or aromatic solvents is provided, whereafter(b) per equivalent of {2-[4-(α-phenyl-p-chlorobenzyl)piperazin-1-yl]}ethanol employed, 1-2 equivalents of a metal haloacetate or of haloacetic acid, as well as 3-7 equivalents of an alkaly metal hydroxyde are added to the solution as per (a), providing a reaction mixture, where 0.05-0.3 volumes, referred to the weight of {2-[4-(α-phenyl-p-chlorobenzyl)piperazin-1-yl]}ethanol employed, of water and 0.1-1.2 volumes, referred to the weight of {2-[4-(α-phenyl-p-chlorobenzyl)piperazin-1-yl]}ethanol employed, of a polar aprotic, water miscible solvent are added, keeping the internal temperature of the reaction mixture below 60° C., whereafter(c) the cetirizine base formed within the reaction mixture is converted into its dihydrochloride salt and isolated as such.
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Page/Page column 3-4
(2009/02/11)
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- Crystalline cetirizine monohydrochloride
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A novel crystalline form of cetirizine monohydrochloride and processes for making the crystalline form as well as compositions, pharmaceutical compositions, and methods utilizing the crystalline form are described.
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- Novel amorphous form of [2-[4-[(4-chlorophenyl)-phenyl methyl]-1-piperazinyl]ethoxy]acetic acid and process for the preparation thereof
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A novel amorphous form of cetirizine and processes for making the amorphous form as well as compositions, pharmaceutical compositions, and methods utilizing the crystalline form are described.
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Page/Page column 6
(2008/06/13)
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- Process for the preparation of {2-[4-(alpha-phenyl-p-chlorobenzyl)piperazin-1-yl]ethoxy} acetic acid and novel intermediates therefor
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The invention refers to a novel process for the preparation of cetirizine of formula (I) as well as to novel {2-[4-(α-phenyl-p-chloro-benzyl)piperazin-1-yl]ethoxy}acetamides of formula II, wherein R1 and R2 represent, independently, a C1-4 alkyl group optionally substituted by a phenyl group, a C2-4 alkenyl group or a cyclohexyl group, or R1 and R2 form together with the adjacent nitrogen atom a morpholino group. According to the novel process, an acetamide of formula (II) is hydrolized, if desired in the presence of a phase transfer catalyst, to obtain cetirizine.
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- A PROCESS FOR THE PREPARATION OF 2- 2- 4-(DIPHENYLMETHYL)-1-PIPERAZINYL]ETHOXY ACETIC ACID COMPOUNDS OR SALTS THEREOF
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2-{2-[4-(diphenylmethyl)-1-piperazinyl]ethoxy}acetic acid compounds of general formula (I) wherein R and R independently represent hydrogen, halogen, lower alkoxy or trifluoromethyl, or salts thereof are prepared by reacting a corresponding 2-[4-(diphenylmethyl)-1-piperazinyl]ethanol with a 2-substituted acetaldehyde dialkylacetal in the presence of a proton acceptor in an inert solvent to form a corresponding diphenylmethylpiperazinoethoxyacetaldehyde dialkylacetal, and thereafter hydrolysing the acetal to the corresponding aldehyde, catalysed by a proton donor, and then oxidising the aldehyde to the acid (I) by means of a suitable oxidation agent. If desired, the acid (I) is converted into a salt thereof. The process is cheap, easy to perform and gives a high yield. The most interesting compound is 2-{2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]-ethoxy}acetic acid in the form of its dihydrochloride known by the generic name of cetirizine. The 2-{2-[4-(diphenylmethyl)-1-piperazinyl]ethoxy}acetaldehyde compounds and their dialkylacetals are novel compounds.
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Page/Page column 5
(2008/06/13)
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- CRYSTALLINE [2-[4-[(4-CHLOROPHENYL)-PHENYL METHYL]-1-PIPERAZINYL] ETHOXY] ACETIC ACID DIHYDROCHLORIDE
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A crystalline form of cetirizine dihydrochloride is provided. A Form I of cetirizine dihydrochloride having a defined X-ray diffraction pattern is also provided, as well as pharmaceutical compositions containing the same.
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- PHARMACEUTICAL COMPOSITIONS FOR ORAL ADMINISTRATION, COMPRISING AN ACTIVE SUBSTANCE AND A CYCLODEXTRIN
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The invention concerns pharmaceutical compositions for oral administration, comprising an active substance belonging to the family of substituted benzhydrylpiperazines and at least a cyclodextrin.
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- Process for preparing piperazine-substituted aliphatic carboxylates
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A process is disclosed for the preparation of a piperazine-substituted aliphatic carboxylate having the formula where m and n are individually an integer of from 1 to 6, R and R′ are the same or different and are hydrogen, C1to C6alkyl or aryl or heteroaryl that is unsubstituted or is substituted with at least one substituent that is halo, C1to C6alkyl or C1to C6alkoxy and R″ is C3to C12branched alkyl or an organic or inorganic cation. The process comprises treating a solution comprising a compound of the formula wherein m, R and R′ are as defined above and an aliphatic ester of the formula X—(CH2)n—O—CH2—CO(O)R″ where X is a leaving group and n and R″ are as defined above, with an effective amount of a base for a time and at a temperature sufficient to form a piperazine-substituted aliphatic carboxylate. Hydrolysis of the carboxylate with acid produces a piperazine-substituted aliphatic carboxylic acid or the acid salt thereof.
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