cas 144690-92-6, Trityl olmesartan | Articles data

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Preparation and purification method for triphenyl methyl olmesartan compound (I)
The present invention provides a preparation and purification method for triphenyl methyl olmesartan. The method comprises the following steps: forming a triphenyl methyl olmesartan carboxylate reaction liquid by using ethyl 4-(2-hydroxy-2-propanyl)-2-pro
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(2020/01/03)

A high purity of the preparation process of trityl olmesartan medoxomil
The invention discloses a preparation method of a triphenyl methyl olmesartan intermediate compound I. The method comprises the steps of a) hydrolyzing a compound II in the presence of alkali to generate a compound III; b) performing a condensation reaction on the compound III and a compound IV in the presence of a catalyst to prepare a compound I; c) adding water in the step b), and then extracting by using a halogenated hydrocarbon solvent system; d) concentrating the compound I obtained in the step c). The equation is as shown in the specification. The preparation method disclosed by the invention is mild in reaction conditions, small in by-products, high in purity of final products and high in yield; the preparation process is environment-friendly, and is low in wastewater production and beneficial in industrial mass production.
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Paragraph 0020; 0039-0044

(2019/03/21)

Method for preparing high-purity trityl olmesartan medoxomil
The invention relates to a method for preparing high-purity trityl olmesartan medoxomil. An inorganic salt solution is adopted for cooling and crystallization. The trityl olmesartan medoxomil preparedby the method has high purity. The method avoids use of
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Paragraph 0030-0033

(2019/11/13)

Preparation method of high purity olmesartan medoxomi I
The invention relates to a preparation method of high purity olmesartan medoxomi I. The preparation method comprises following steps: 1,5-(4'-bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole (A) and ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate (B) are taken as raw materials to prepare an olmesartan medoxomi I intermediate 1 (C) through condensation reaction; theolmesartan medoxomi I intermediate 1 (C) is subjected to hydrolysis in the presence of sodium hydroxide so as to obtain a compound (D); without separation, the compound (D) and raw material 4-Cloromethyl-5-methyl-1,3-dioxol-2-one (E) are directly subjected to condensation reaction so as to obtain an olmesartan medoxomi I intermediate 2 (F); and the olmesartan medoxomi I intermediate 2 (F) is subjected to deprotection in a 75% acetic acid aqueous solution so as to obtain olmesartan medoxomi I crude product, and acetone is adopted for recrystallization so as to obtain high purity olmesartan medoxomi I (G). The reaction conditions are mild; side products are few; the finished product purity is high; the preparation method is safe, is friendly to the environment, and is suitable for industrialized production; residual solvent is less; and quality standards are achieved.
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(2018/09/08)

A olmesartan medoxomil and its preparation method (by machine translation)
The invention discloses a olmesartan medoxomil and its preparation method, the present invention discloses a olmesartan medoxomil, its chemical structure is: The present invention novel method for preparation method, comprises the following steps: (1) preparing AMST - 3 C45 H44 N6 O3 ; (2) preparing C43 H39 N6 NaO3 AMST - 4; (3) preparing C48 H44 N6 O6 AMST - 6; (4) preparing olmesartan sha tanzhi thick; (5) to make the C29 H30 N6 O6 Olmesartan medoxomil. The invention separation effect is good, relatively low viscosity system, split-phase required time is short, the time is saved but also reduces energy consumption. Filtering and separating the high recovery rate, the product quality is high, the running cost is low; process without the need to add chemical, solvent solvent, not into the secondary pollution material; equipment and automatic operation, good stability, easy to realize industrial demand. (by machine translation)
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(2017/11/16)

Preparation method of olmesartan medoxomil
The invention provides an improved synthesis method of olmesartan medoxomil. The improved synthesis method comprises the following steps: enabling ethyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate and 4-[2-(triphenylmethyl tetrazole-5-yl)phenyl]phenylmethyl bromide to make alkylation reaction; after carrying out hydrolysis on an ester group, enabling a product and a 4-substituted methyl-5-methyl-2-oxo-1,3-dioxole derivative to make nucleophilic substitution reaction, so as to form ester; then removing the protection of triphenylmethyl to obtain the olmesartan medoxomil. According to the improved synthesis method provided by the invention, alkylation, hydrolysis, esterification and protective group removal reaction are finished through a one-pot method, and a separation and purification process is not needed. A few of instruments and equipment are needed and a technology is simple; the whole process only utilizes an organic solvent, so that industrial production is facilitated; filtering and desalting are used for replacing extraction and washing operation, so that a few of three wastes are generated, and the improved synthesis method is environmentally friendly.
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Paragraph 0043; 0044; 0045; 0046

(2017/11/30)

A process for the preparation of olmesartan
The invention discloses a preparation method of Olmesartan Medoxomil. The method is used for synthesizing an important intermediate 4-[2-(2-triphenylmethyl tetrazole-5-yl) phenyl] benzyl bromide (a compound III) so as to prepare the compound Olmesartan Medoxomil. The method is high in yield, easy to separate and purify, simple to operate and suitable for industrial production.
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(2017/04/19)

Preparation method of key intermediate of olmesartan medoxomil and olmesartan medoxomil
The invention relates to a preparation and refinement method of a key intermediate of olmesartan medoxomil and the olmesartan medoxomil, and belongs to the technical field of medicine. The structural formula of the olmesartan medoxomil is shown as a formula I (Please see the specification).
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Paragraph 0076; 0077; 0078; 0079; 0080; 0081; 0082

(2016/10/17)

Method for preparing olmesartan medoxomil
The invention provides a method for preparing olmesartan medoxomil and belongs to the field of medicine synthesis. The method comprises the steps that imidazole monoester and 5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole (BBTT) are used as starting materials and subjected to condensation, hydrolysis and acidification through a one-pot method in an acetone system to obtain 4-(1-hydroxyl-1-methylethyl)-2-propyl-{4-[2-(triphenylmethyl tetrazole-5-base) phenyl] phenyl} methylimidazole-5-carboxylic acid; the obtained product is then esterified with 4-chloromethyl-5-methyl-1,3-dioxole-2-ketone, wherein the purity of the esterified product through purification is larger than or equal to 99.5%; the esterified product is subjected to deprotection under the action of a 22.5% sulfuric acid solution to obtain highly purified olmesartan medoxomil. Condensation and esterification are performed through the one-pot method, so that the operation procedure is simplified, control is facilitated, the key intermediate esterified product is purified and then subjected to deprotection in the reaction, the olmesartan medoxomil with purity larger than or equal to 99.5% can be obtained, the total yield can reach 60%-75%, the raw materials are easy to obtain, cost is low, and the method is applicable to industrial production.
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(2016/10/10)

A process for the preparation of olmesartan
The invention relates to a method for preparing a medicine olmesartan medoxomil for treating hypertension, belongs to the field of medicines, and provides a method for preparing the olmesartan medoxomil with low material cost and mild reaction condition. The method comprises the following steps of: feeding two initial raw materials ( a compound 1 and a compound 2) according to a mole ratio of 1:1 during the process; adding the polyethylene glycol/N,N-dimethylacetamide composite catalyst to be completely reacted with the two initial raw materials so as to avoid a necessary impurity control process caused by excessive raw materials during classic reaction; and removing triphenylmethyl from a methanol/organic solvent mixed system to avoid participation of acid. Based on the improvement, the operation is greatly simplified, the cost is reduced, and the industrial production is facilitated.
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(2018/02/04)

DEPROTECTION METHOD FOR TETRAZOLE COMPOUND
The present invention relates to a method of deprotecting a tetrazole compound, useful as an intermediate for angiotensin II receptor blockers, and provides a novel production method of angiotensin II receptor blockers. Provided is a production method of a compound represented by the formula [3] or [4] or a salt thereof, including (i) reducing a compound represented by the formula [1] or [2] or a salt thereof in the presence of a metal catalyst and an alkaline earth metal salt, or (ii) reacting the compound with a particular amount of Br?nsted acid: wherein each symbol is as defined in the present specification.
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(2015/09/23)

METHOD FOR PRODUCING BIARYL COMPOUND
Provided is a novel production method capable of producing a biaryl compound, which is useful as an intermediate for angiotensin II receptor blockers, economically under conditions suitable for industrial production. A production method of a biaryl compound of the formula [3] or a salt thereof, including reacting a 2-phenylazole derivative of the formula [1] or a salt thereof, with a benzene derivative of the formula [2] or a salt thereof in the presence of a metal catalyst, a base, and one or more kinds of compounds selected from the group consisting of (a) a monocarboxylic acid metal salt, (b) a dicarboxylic acid metal salt, (c) a sulfonic acid metal salt, and (d) a phosphate or phosphoric amide metal salt represented by RAxP(O)(OM)y wherein each symbol is as defined in the DESCRIPTION.
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(2015/07/15)

Improved synthesis process of olmesartan medoxomil derivatives
The present invention relates to an improved olmesartan medoxomil derivative preparation method. More specifically, the olmesartan medoxomil derivative preparation method includes the steps of: initiating a coupling reaction between imidazole compounds and biphenyl methyl halide compounds; initiating a de-esterification reaction of the products of the coupling reaction; and initiating a condensation reaction between the de-esterified products with dioxolen derivatives. The present invention can optimize the reaction conditions of the coupling and de-esterification reactions to minimixe the content of the conventionally produced byproducts and residual solvent to significantly increase the yield and purity of the target products. The final olmesartan medoxomil derivatives obtained by using the method has the residual solvent content less than or equal to 500 ppm, thereby being lowered to 1/10 or less of the ICH guidelines.
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(2016/12/22)

PROCESS FOR OLMESARTAN MEDOXOMIL
The present invention provides a process for the preparation of substantially pure trityl olmesartan medoxomil. The present invention also provides a process for purification of trityl olmesartan medoxomil. The present invention further provides a process for purification of olmesartan medoxomil.
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Paragraph 0050

(2013/07/31)

PROCESS FOR OLMESARTAN MEDOXOMIL
The present invention provides a process for the preparation of substantially pure trityl olmesartan medoxomil. The present invention also provides a process for purification of trityl olmesartan medoxomil. The present invention further provides a process for purification of olmesartan medoxomil.
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Page/Page column 9-10

(2012/01/14)

PROCESS FOR PREPARING OLMESARTAN MEDOXOMIL
The invention relates to a process for preparing olmesartan medoxomil by the reaction of sodium 5-(1-hydroxy-1-methylethyl)-2-propyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylate, obtained by the reaction between ethyl 5-(1-hydroxy-1-methylethyl)-2-propyl-3H-imidazole-4- carboxylate from and 5-(4'-bromomethylbiphenyl-2-yl)-1-trityl-1H-tetrazole followed by saponification, with 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one, deprotection and purification.
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(2012/05/19)

NOVEL SOLVATE CRYSTALS
Acetone solvate crystals of trityl olmesartan medoxomil are provided.
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Page/Page column 5

(2012/03/26)

PREPARATION OF OLMESARTAN MEDOXOMIL
Processes for preparing olmesartan medoxomil. In embodiments, processes for preparing olmesartan medoxomil do not require isolating one or more intermediate compounds.
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(2011/02/24)

PROCESS FOR PREPARING OLMESARTAN MEDOXOMIL INTERMEDIATE
The present invention discloses a process for preparing tritylolmesartan medoxomil with purity greater than 98% and further converting such an intermediate to olmesartan medoxomil.
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Paragraph 0077-0078

(2011/07/06)

PROCESS FOR THE PREPARATION OF OLMESARTAN MEDOXOMIL
The present invention provides a process for the preparation of Olmesartan medoxomil] by condensing the ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate with 4-[2-(trityl tetrazol-5-yl)phenyl]benzyl bromide to obtain ethyl 4-(1-hydroxy-1-methyl ethyl)-2-propyl-1-{4-[2-(trityl tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate and then hydrolyzing ethyl 4-(1-hydroxy-1-methyl ethyl)-2-propyl-1-{4-[2-(trityl tetrazol-5-yl)phenyl]phenyl}methyl imidazole-5-carboxylate to obtain trityl Olmesartan dihydrate followed by reacting trityl Olmesartan dihydrate with 4-chloromethyl-5-methyl-2-oxo-1,3-dioxolene to obtain trityl Olmesartan medoxomil and then deprotecting trityl Olmesartan medoxomil to obtain Olmesartan medoxomil.
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Page/Page column 5-6

(2009/12/04)

Efficient synthesis of olmesartan medoxomil, an antihypertensive drug
This document describes a simple and robust process for the synthesis of olmesartan medoxomil. This tailored process allows us to synthesize olmesartan medoxomil on a large scale with 50% overall yield. Also, our process has excellent control of the impurity profile in all the stages. Copyright Taylor & Francis Group, LLC.
Babu, Karrothu Srihari,Reddy, Mallepalli Srinivasa,Tagore, Amirisetty Ravindranath,Reddy, Gade Srinivas,Sebastian, Sony,Varma, Mudunuru Satish,Venkateswarlu, Gandu,Bhattacharya, Apurba,Reddy, Padi Pratap,Anand, Ramasamy Vijaya
experimental part
p. 291 - 298
(2009/05/07)

PROCESS FOR THE PREPARATION OF OLMESARTAN MEDOXOMIL
The present invention relates to an improved process for the manufacture of olmesartan and pharmaceutically acceptable salts and esters thereof as an active ingredient of a medicament for the treatment of hypertension and related diseases and conditions.
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Page/Page column 8

(2009/05/28)

PROCESS FOR PREPARING TRITYL OLMESARTAN MEDOXOMIL AND OLMESARTAN MEDOXOMIL
A process for the preparation of trityl olmesartan comprising (a) condensing 4-(1-hydroxy- 1-methylethyl)-2-propyl-imidazol-5-carboxylic acid alkyl ester with trityl biphenyl bromide in the presence of a polar aprotic solvent and a base selected from the group consisting of alkali metal carbonates, alkali metal hydroxides, alkali metal alkoxides, and tertiary amines to obtain a compound of formula (V): b) deesterifying the compound of formula (V) with a base; and c) reacting the product of step (b) with 4-halomethyl-5-methyl-2-oxo-1,3-dioxolene of formula (IV): wherein X is halogen selected from F or Cl or Br or I, to obtain trityl olmesartan medoxomil of formula. The trityl olmesartan medoxomil may be deprotected to produce olmesartan medoxomil.
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Page/Page column 16-17; 18

(2008/06/13)

PROCESS FOR THE PREPARATION OF OLMESARTAN MEDOXOMIL
The present invention relates to an improved process for the manufacture of olmesartan and pharmaceutically acceptable salts and esters thereof as an active ingredient of a medicament for the treatment of hypertension and related diseases and conditions.
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Page/Page column 5; 21-22

(2010/11/25)

Process for the preparation of olmesartan medoxomil
The present invenion relates to an improved process for the manufacture of olmesartan and pharmaceutically acceptable salts and esters thereof as an active ingredient of a medicament for the treatment of hypertension and related diseases and conditions.
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Page/Page column 12

(2010/11/28)

A METHOD OF REMOVING THE TRIPHENYLMETHANE PROTECTING GROUP FROM PRECURSORS OF ANTIHYPERTENSIVE DRUGS
A method of removing the triphenylmethane protecting group from precursors of antihypertensive drugs of general formula I, wherein R is a metabolically degradable group, B is a heterocyclic moiety with one or two 5- or 6-membered rings at least one of which contains two nitrogen heteroatoms, in which the compound of formula I is reacted with water in the presence of a solvent which is partially or completely miscible with water.
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Page/Page column 9; 10

(2008/06/13)

ANGIOTENSIN II ANTAGONIST 1-BIPHENYLMETHYLIMIDAZOLE COMPOUNDS AND THEIR THERAPEUTIC USE
Compounds of the following formula (I) or the formula (I) p : STR1 wherein R 1 is alkyl or alkenyl; R 2 and R 3 are hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl, or aryl fused to cycloalkyl; R 4 is hydrogen, alkyl, alkanoyl, alkenoyl, arylcarbonyl, alkoxycarbonyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydrothienyl, tetrahydrofuryl, a group of formula--SiR a R b R c, in which R a, R b and R c are alkyl or aryl, alkoxymethyl, (alkoxyalkoxy)methyl, haloalkoxymethyl, aralkyl, aryl or alkanoyloxymethoxycarbonyl; R 5 is carboxy or--CONR 8 R 9, wherein R 8 and R 9 hydrogens or alkyl, or R 8 and R 9 together form alkylene; R 6 is hydrogen, alkyl, alkoxy or halogen; R. sup.7 is carboxy or tetrazol-5-yl; R p. sup.1 is hydrogen, alkyl, cycloalkyl or alkanoyl; R p 2 is a single bond, alkylene or alkylidene; R p 3 and R p 4 are each hydrogen or alkyl; R. sub.p 6 is carboxy or tetrazol-5-yl; and X p is oxygen or sulfur; and pharmaceutically acceptable salts and esters thereof. The compounds are AII receptor antagonists and thus have hypotensive activity and can be used for the treatment and prophylaxis of hypertension. The compounds may be prepared by reacting a biphenylmethyl compound with an imidazole compound.
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(2008/06/13)