- Novel stereoselective synthesis and chromatographic evaluation of E-guggulsterone
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A new stereoselective synthesis of E-guggulsterone is described starting from androsten-3,17-dione. Protection of the ring A enonic system, followed by regioselective Wittig reaction and C-16 oxidation, affords E-guggulsterone in good yields and high ster
- Gioiello, Antimo,Sardella, Roccaldo,Rosatelli, Emiliano,Sadeghpour, Bahman M.,Natalini, Benedetto,Pellicciari, Roberto
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- Synthesis method of alkyl acid testosterone
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The invention discloses a synthesis method of alkyl acid testosterone, and belongs to the technical field of synthesis and processing of medicines. The method comprises the following steps of: taking4-androstenedione (4AD) as an initial raw material, firstly, carrying out enol ether protection on the keto group at the site 3, and reducing carbonyl at the site 17 into hydroxyl; or taking 4-androstenedione (4AD) as an initial raw material, firstly carrying out enol ether protection on the keto group at the site 3, then reducing carbonyl at the site 17 into hydroxyl, then carrying out hydrolysison the site 3 to obtain testosterone, and carrying out esterification and third-site hydrolysis to obtain the testosterone ester after testosterone third-site ketal protection. According to the method disclosed by the invention, the third site is protected during esterification reaction, the generation of impurities can be reduced, and an esterification reaction solvent is a water-insoluble organic solvent, so that after the reaction is completed, products can be directly extracted in a layered manner, a large amount of water does not need to be added to separate out the products, the amountof wastewater is reduced, the solvent can be recycled, and the process is more suitable for industrial production.
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Paragraph 0037-0038; 0043-0044; 0053-0054; 0059-0060; 0065
(2020/12/10)
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- Preparation method of androst-2-en-17-one
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The invention discloses a preparation method of androst-2-en-17-one. The method comprises the steps that 4-androstenedione is adopted as a raw material, three-step reactions of a protective reaction,a reduction reaction and a deprotection reaction are ado
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Paragraph 0028; 0031-0032; 0035; 0038-0039; 0042; 0045-0046
(2019/04/30)
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- Preparation method of 5alpha-androstane-3,17-dione
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The invention relates to a preparation method of 5alpha-androstane-3,17-dione. The method specifically comprises the following steps: 1, carrying out an etherification reaction on 4-androstenedione, triethyl orthoformate and anhydrous ethanol in the presence of an etherification catalyst, and performing post-treatment after the etherification reaction is completed in order to prepare a compoundwet 3-ethoxy-3,5-androstadien-17-one; 2, adding a the wet 3-ethoxy-3,5-androstadien-17-one into a methanol-dichloromethane mixed solvent, performing uniform stirring, adjusting the pH value of the obtained solution, carrying out a catalytic hydrogenation reaction under the action of a palladium-carbon catalyst, and filtering out the catalyst after the reaction is finished in order to obtain a 3-ethoxy-3-androstene-17-one solution; and 3, carrying out a hydrolysis reaction on the 3-ethoxy-3-androstene-17-tone solution and an acid, removing the solvent after the hydrolysis reaction is finished,and carrying out filtering, water washing and drying to obtain the 5alpha-androstane-3,17-dione. The method has the advantages of short process route, easily controlled production process, environmental friendliness, low production cost, and suitableness for industrial large-scale production.
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Paragraph 0039; 0044; 0049
(2019/12/25)
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- Preparation method of 5alpha-androstane-17-hydroxy-3-one
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The invention relates to a preparation method of 5alpha-androstane-17-hydroxy-3-one. The method specifically comprises the following steps: 1, carrying out an etherification reaction on 4-androstenedione, triethyl orthoformate and anhydrous ethanol in the
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Paragraph 0038; 0043; 0048
(2019/12/25)
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- A [...] intermediate androst - 17 α - methyl - 17 β - hydroxy -3 - ketone (by machine translation)
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The present invention provides a [...] intermediate androst - 17 α - methyl - 17 β - hydroxy - 3 - ketone synthesis method, the method is to 4 - androstenedione (abbreviated as 4 AD) as raw materials, through the 3 position alkone pyridynyl alkylene ether, 17 [...] addition; then in Grignard addition after acid hydrolysis is not carried out in advance 5 at the catalytic hydrogenation reaction of the olefinic bond, then do the 3 bit ether with the 17 bit dual-hydrolysis preparation to obtain compound androst - 17 α - methyl - 17 β - hydroxy - 3 - one, HPLC purity 99.0% or more. The method of the invention route is brief, the production process is easy to control, environmental friendly, low production cost, is suitable for industrial scale production. (by machine translation)
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Paragraph 0016; 0017; 0020; 0021; 0024; 0025
(2019/05/04)
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- Preparation method of 17 beta-androst-4-ene-3-one-17-carboxylic acid
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The invention discloses a preparation method of 17 beta-androst-4-ene-3-one-17-carboxylic acid. The preparation method comprises that 4-androstenedione (called as 4AD for short) as a raw material andtriethyl orthoformate undergo a reaction in an organic solvent under acid catalysis, the reaction product is after-treated to form an etherate, the etherate is dissolved in an organic solvent and undergoes a reaction with trimethylsulfonium iodide under strong base catalysis, the product is after-treated to form an epoxide, the epoxide is dissolved in an organic solvent and then is subjected to rearrangement under acid catalysis to form an aldehyde, and aldehyde is dissolved in an organic solvent and undergoes a catalytic oxidation reaction with hydrogen peroxide acid to produce 17 beta-androst-4-ene-3-one-17-carboxylic acid. The 17 beta-androst-4-ene-3-one-17-carboxylic acid has a melting point of 244-246 DEG C, HPLC content of 99.0% or more and a reaction weight total yield of 70-72%. Compared with the traditional method, the preparation method utilizes cheap and easily available raw materials, has simple and environmental friendly processes and a high synthesis yield, produces highquality products, reduces a cost by 30-40% and is conducive to industrial production.
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Paragraph 0012; 0013; 0017; 0021
(2018/04/02)
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- PROCESS FOR PREPARATION OF TESTOSTERONE
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The present invention relates to a process for purification of 4-androsten-3,17-dione (II) and its conversion to testosterone (I) having purity > 99 % as measured by HPLC.
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Page/Page column 6
(2017/06/21)
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- A acetate synthesis method
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The invention relates to a synthesis method of abiraterone acetate. According to the synthesis method of the abiraterone acetate, a compound 1 is taken as a revelator, and the abiraterone acetate is prepared through steps such as esterification, Grignard reagent reaction, dehydration, acylation, reduction, acetylation and the like.
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Paragraph 0054; 0055; 0056; 0057
(2017/08/31)
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- A preparation method of male nandrolone (by machine translation)
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A male nandrolone preparation method, namely in order to 4 - androstenedione (abbreviated as 4AD) as raw materials, the first 4AD with the original carboxylic acid triethyl in organic solvent, acid catalyzed reaction shall be etherification 3 - ethoxy - androstane - 3, 5 - diene - 17 - one; then the etherification in the organic solvent, adding metal borohydride reducing agent, etherification molecule in the 17 bit keto also restored to hydroxy, shall also the original 3 - ethoxy - androstane - 3, 5 - diene - 17 - ol; then also the original in the organic solvent, adding hydrogenation reaction catalyst, selective hydrogenation also the original molecule of 5 bit double bond, shall be hydride 3 - ethoxy - androstane - 3 - en - 17 - ol; finally the hydride in an organic solvent, acid catalytic hydrolysis extraction male nandrolone; the method of the invention compared with the traditional production method, raw material sources are wide, short synthetic route, process convenient and environmental protection, high product yield, economy and environmental protection, the production cost is reduced 35 - 40%, which is very beneficial to industrial production. (by machine translation)
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Paragraph 0012; 0016; 0020
(2017/08/28)
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- Testosterone preparation method
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Provided is a testosterone preparation method. The method uses androstenedione (also known as 4AD) as the raw material and comprises the following steps: A, synthesizing imidazoleethylamine which is to mix the 4AD and triethyl orthoformate with higher alcohol organic solution for acid catalysis to obtain 3beta Ethoxy-androsta 3,5-diene 17-ketone; B, synthesizing reducing substance, mixing the imidazoleethylamine with organic solution, adding metal borohydride to reduce the 17 ketone to 3beta Ethoxy-androsta 3,5-diene 17-alcohol; C, synthesizing testosterone, mixing the aforementioned reducing substance with organic solution, hydrolyzing with water, conducting post-treatment to acquire the testosterone crude which is mixed with low carbon alcohol to be decolored by active carbon and recrystallized, obtaining the final product of testosterone. The overall recovery rate of synthesized weight is 70%-75%. The method has the advantages of widely available material sources, simple operation, high yield rate, high purity, extreme reduction of costs, high recovery rate of solution in the reaction and processing, cost effectiveness and environmental protection.
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Paragraph 0009; 0012; 0015
(2017/08/27)
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- Preparation method of methyltestosterone
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The invention provides a preparation method of methyltestosterone. 4AD short for 4-androstenedione is taken as a raw material, and etherate is synthesized firstly as follows: 4AD and triethyl orthoformate are subjected to an acid catalyzed reaction in a low-carbon alcohol organic solvent, and 3-ethoxy-androst-3,5-diene-17-one as the etherate is obtained; then a Grignard product is synthesized as follows: a Grignard reagent methyl magnesium halide and the etherate are placed in an organic solvent, the 17-position ketone group of the etherate and the Grignard reagent are subjected to addition, and the Grignard product 3-ethoxy-17a-methyl-androst-3,5-diene-17-ol is obtained through hydrolysis; then the Grignard product is subjected to an acid catalyzed hydrolysis in an organic solvent, and crude methyltestosterone is obtained; the crude methyltestosterone is decolorized by activated carbon in C4-below low-carbon alcohol and recrystallized, the methyltestosterone is obtained, HPLC content is 99.0%-99.5%, and the total yield of synthesis weight is 75%-78%. According to the method, the raw materials are widely sourced, the process is simple and convenient to operate, the product yield is high, the purity is good, the solvent recovery rate is high in reaction and technological processing, and the method is economical and environment-friendly.
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Paragraph 0011; 0012; 0015; 0018
(2017/08/27)
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- A method for synthesis of alkyne progesterone
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The invention discloses a synthesis method of ethisterone which is prepared by adopting 4AD namely soybean oil tailings as a raw material, carrying out etherification protection as well as two-step reaction, namely, ethynylation and hydrolysis, and then refining. According to the invention, the raw material is replaced, that is the industrial tailing fermentation product 4AD of the soybean oil is used to replace diene; the raw material is wide in supply, low in cost and little in pollution; the reaction route is short; the process is simple; the auxiliary materials are commonly used chemical products; the generation amount of waste gas, waste water and waste solid is small and is a quarter of that generated in the traditional process.
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Paragraph 0025; 0035; 0036; 0042
(2017/12/28)
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- Preparation method of mestanolone
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The invention relates to a preparation method of mestanolone. The preparation method comprises the following steps of adopting 4AD as a raw material, carrying out acid catalyzed reaction on the 4AD and triethyl orthoformate in an organic solvent such as lower alcohol to obtain etherate; carrying out grignard addition reaction on the etherate and a methyl-grignard-reagent in an organic solvent to obtain grignard which is 3-ethyoxyl-17a methyl-androstane-3,5-diene-17-alcohol; then catalyzing through palladium-charcoal, carrying out double-bond hydrogenation on a grignard 5 bit to obtain hydride which is 3-ethyoxyl-androstane-3 alkene-17-ketone, finally carrying out acid-catalyzed hydrolysis on the hydride in the organic solvent such as lower alcohol to obtain a mestanolone crude product, and then carrying out decoloration refining through ethyl alcohol and activated carbon to obtain the mestanolone. The HPLC content is 99.5 percent or more, the melting point is 192.5 to 194.0 DEG C, and the synthesis weight total yield is 76 to 83 percent. The preparation method provided by the invention is cheap and easily available in raw materials, simple and convenient in process operation, good in product purity, high in yield, high in solvent recovery rate, reduced in production cost by 25 to 30 percent, and favorable for industrial production.
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Paragraph 0010; 0014; 0018
(2017/11/18)
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- 3-β-hydroxy-androstene -17-ketone preparation method
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A preparation method for 3-beta-hydroxyandrost-17-one comprises taking 4AD (androstenedione) as a raw material, performing 3-position alkene etherification on 4AD in an organic solvent, employing triethyl orthoformate as a reagent, and performing acid cat
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Paragraph 0018-0020
(2017/05/12)
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- Process for the preparation of danazol
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The invention discloses preparation methods of danazol and an intermediate thereof. The preparation method of danazol is prepared by the steps of taking androstenedione as a starting raw material, and carrying out 3-site enol etherification, 17-site carbonyl ethinylation, 3-site hydrolysis, 2-site methylidynel hydroxylation and oximation to obtain danazol. The 3-site enol etherification comprises firstly carrying out a reaction of androstenedione and triethyl orthoformate for 4-10 h in the presence of absolute ethyl alcohol and p-toluenesulfonic acid and at the temperature of 30-50 DEG C, then adding triethylamine at the temperature of 0-10 DEG C, and continuing to carry out a reaction for 0.2-1 h; the 17-site carbonyl ethinylation comprises firstly carrying out a reaction of a potassium hydroxide powder for 1-2 h in an acetylene airflow and at the temperature of 5-10 DEG C, and then carrying out a reaction with the 3-site enol etherified product for 2-4 h in the presence of tetrahydrofuran and a catalyst, at the temperature of 15-30 DEG C and in the acetylene airflow. The 3-site enol etherification is mild in reaction conditions and relatively high in yield, and the 17-site carbonyl ethynylation is relatively high in reaction yield and relatively short in time.
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Paragraph 0013; 0015; 0016; 0027; 0031
(2019/02/04)
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- A by the 3,17-dione steroid preparing steroid the synthetic method of the compound of
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The invention discloses a synthetic method of steroid type drugs and intermediates, in particular relates to a synthetic method for preparing 17-hydroxy-20-ketone steroid compounds from 3,17-diketone steroids, and belongs to the field of synthesis of drugs. The method takes 3,17-diketone steroids as raw materials and adopts a conventional, environment-friendly, low-toxicity reagent, and the steroid type drugs such as cortisone, hydrocortisone, metacortandracin, or hydroprednisone, or intermediates 17alpha-hydroxy-20-ketone compounds are prepared simply and conveniently at high yield by selective protection of C3 or (and) C11-ketone group, Wittig reaction of C17, selective oxidization of 17(20)-position double bonds and halogenating replacement. The aftertreatment is simple, few three wastes are generated, the reaction selectivity is good, the yield is high, and byproducts anti-pregnancy steroidal drugs and steroidal compounds can be obtained. The raw materials are easy to get, the cost is low and the synthetic process is simple; the synthetic method is suitable for industrial production.
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Paragraph 0105-0111
(2017/03/14)
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- Preparation method of 17beta-androst-4-ene-3-one-17-carboxylic acid
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The invention discloses a preparation method of 17beta-androst-4-ene-3-one-17-carboxylic acid. The preparation method comprises the following specific operation steps of performing acid catalyzed reaction on 4AD (Androstenedione) and triethyl orthoformate in low-carbon alcohol organic solvent to obtain etherate 3-ethyoxyl-androst-3,5-diene-17-one; performing 17-situ addition on the obtained etherate and nitromethane in the organic solvent under the catalysis of ethanediamine to obtain a nitro compound; reducing the obtained nitro compound in the organic solvent with zinc powder, and hydrolyzing with acid to obtain 17beta-androst-4-ene-3-one-17-formaldehyde; oxidizing an intermediate obtained by hydrolyzing in the organic solvent with hydrogen peroxide to obtain a 17beta-androst-4-ene-3-one-17-formic acid crude product; recrystallizing the crude product through methyl alcohol to obtain a finished product. According to the preparation method, total yield of synthesis weight is 70 to 72 percent, and the content of HPLC (High Performance Liquid Chromatography) is 99.0 percent or over 99.0 percent. The method disclosed by the invention has the advantages of high production yield, low cost, good purity, stable quality, high recovery rate of solvent, economy and environment friendliness.
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Paragraph 0014
(2016/10/07)
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- Industrial production method of exemestane
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An industrial production method of exemestane comprises the following steps: adding androsta-1,4-diene-3,17-dione, anhydrous ethanol, triethyl orthoformate and p-toluenesulfonic acid into a reactor, stirring above added materials, carrying out rotary drying, and crystallizing the obtained dried mixture to obtain an intermediate YXMT01; sequentially adding the intermediate YXMT01, anhydrous ethanol, tetrahydrofuran, 37% formaldehyde, N-toluidine and p-toluenesulfonic acid into the reactor, and carrying out rotary drying to obtain an intermediate YXMT02; sequentially adding the intermediate YXMT02, ethyl acetate and hydrochloric acid into the reactor, precipitating, carrying out suction filtration to obtain white solid, and re-crystallizing the white solid with toluene to obtain an intermediate YXMT03; and sequentially adding the intermediate YXMT03, toluene and IBX into the reactor, stirring the added substances, cooling the obtained substance, concentrating the obtained filtrate, and re-crystallizing the obtained concentrate to obtain white solid YXMT. The method has the advantages of avoiding of uncontrollability of a one-kettle method in industrial production, cheap sources of raw materials, easiness in control of the process operation, high yield, stable quality, and suitableness for industrial production.
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Paragraph 0010; 0011; 0012; 0013
(2017/02/09)
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- PROCESS FOR THE PREPARATION OF DROSPIRENONE
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The present invention describes a process for the preparation of drospirenone (I) using androstendione as a starting material. In particular, androstendione protected on carbonyl group in position 3 as an enol-ether is functionalized in position 16 with a sulfoxide group and the derivative thus obtained undergoes thermal elimination in alkaline to give androsta-4,15- diene-3, 17-dione (V) which is further transformed into Drospirenone (I).
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Page/Page column 5-6
(2009/06/27)
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- 5β-cyano-substituted steroid compounds
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Novel 5β-cyano steroid compounds including compounds of Formula VII: wherein A—A, B—B, R3, R8and R9are as defined in the specification.
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- Processes for preparation of 9,11-epoxy steroids and intermediates useful therein
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Multiple reaction schemes, process steps and intermediates are provided for the synthesis of epoxymexrenone, useful as a diuretic, and other 9,11-epoxy-steroids.
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- Sulfuric acid adsorbed on silica gel. A multipurpose acid catalyst
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A series of acid catalyzed reactions like the dehydration of alcohols, conversion of ketones to 1,3-dioxolanes and their hydrolysis, α, β- unsaturated ketones to enol ethers, and alcohols to methyl-methoxyethyl ethers are performed efficiently in high yield with sulfuric acid adsorbed on silica gel as catalyst.
- Chavez,Suarez,Diaz
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p. 2325 - 2339
(2007/10/02)
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- Process for preparing active compounds
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A process for the preparation of a compound of the formula (A): STR1 wherein: R3 is a C1-5 alkyl group, a C3-6 alkenyl group, a C3-6 cycloalkyl group or an alkylphenyl group in which the alkyl moiety contains 1
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