- 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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(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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- 2-[2-[4-[(4-CHLOROPHENYL) PHENYLMETHYL]-1-PIPERAZINYL]ETHOXY]ACETIC ACID MONOHYDROCHLORIDE AS ANTI-ALLERGENIC COMPOUND AND PROCESS FOR ITS PRODUCTION
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An anti-allergenic compound having therapeutic value and a process for its manufacture. The disclosure is directed to 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1piperazinyl]ethoxy]acetic acid monohydrochloride, to compositions containing 2-[2-[4-[(4chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid monohydrochloride, and to a process for the preparation of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid monohydrochloride.
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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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(2008/06/13)
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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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- Substituted [2-(1-piperazinyl)ethoxy]methyl compounds
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PCT No. PCT/BE97/00038 Sec. 371 Date Oct. 9, 1998 Sec. 102(e) Date Oct. 9, 1998 PCT Filed Mar. 28, 1997 PCT Pub. No. WO97/37982 PCT Pub. Date Oct. 16, 1997Novel substituted [2-(1-piperazinyl)ethoxy]methyl compounds. The present invention related to novel substituted [2-(1-piperazinyl)-ethoxy]methyl compounds of formula in which R1 represents a -CONH2, -CN, -COOH, -COOM or -COOR3 group, M being an alkali metal and R3 being an alkyl radical having from 1 to 4 carbon atoms; and R2 represents a hydrogen atom or a group -COR4 or -R5, where R4 is chosen from the groups -OR6 or -R7, in which R5 represents an allyl or alkylaryl radical, R6 represents a linear or branched alkyl radical having from 1 to 4 carbon atoms, a haloalkyl, alkylaryl, alkylnitroaryl or alkylhaloaryl radical, and R7 represents a haloalkyl radical, to a process for the preparation of these compounds, and to their use for the preparation of compounds which are themselves valuable intermediates for the preparation of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid or 2-[2-[4-[bis(4-fluorophenyl)methyl]-1-piperazinyl]ethoxy]-acetic acid and/or pharmaceutically acceptable salts thereof.
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- Methods for the manufacture of cetirizine
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PCT No. PCT/CA97/00496 Sec. 371 Date Jan. 20, 1999 Sec. 102(e) Date Jan. 20, 1999 PCT Filed Jul. 11, 1997 PCT Pub. No. WO98/02425 PCT Pub. Date Jan. 22, 1998The present invention relates to a process for the preparation of a [2-[4-[4-(chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid derivative of formula I: and, in particular, for the preparation of cetirizine. The method comprises the oxidation of a primary alcohol of a hydroxyzine. Cetirizine is a non-sedating type histamine H1-receptor antagonist and is used in the treatment of allergic syndromes.
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- 2-[4-(Diphenylmethyl)-1-piperazinyl]-acetic acids and their amides
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New 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids, their amides and their salts, processes for the preparation thereof and therapeutic compositions. These compounds have the formula STR1 wherein Y=--OH or --NH2 ; X and X'=H, halogen, alkoxy or trifluoromethyl; m=1 or 2 and n=1 or 2. The amides of the 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids are prepared either by reacting a 1-(diphenylmethyl)-piperazine with an omegahaloacetamide, or by reacting an alkali metal salt of an omega-[4-(diphenylmethyl)-1-piperazinyl]-alkanol with a 2-haloacetamide, or yet by reacting ammonia with a halide or alkyl ester of a 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acid, whereas the 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids are prepared by hydrolyzing the corresponding amide or lower alkyl ester. These compounds have in particular an antiallergic, spasmolytic and antihistaminic activity.
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