- Method for preparing high-purity erythrocin A
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The invention provides a method for preparing high-purity erythrocin A. According to the method, the high-purity erythrocin A is prepared by alkali transduction on erythromycin thiocyanate and aqueous-phase recrystallization, and the problem of viscosity in a preparation process of erythrocin A in the prior art is effectively solved. The method provided by the invention has a stable process, is easy to operate, and can prepare products with the erythrocin A as high as 96% or more in content; the erythrocin A can be used as a reference substance of the erythrocin A; besides, in the alkali transduction process, the price of dichloromethane used as a solvent is only about half the price of acetone adopted as a solvent in a traditional process, therefore, the production cost is greatly lowered, and the method has a great application prospect.
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Paragraph 0074; 0075; 0076; 0078; 0079; 0080; 0081
(2016/12/22)
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- A NOVEL PROCESS OF LIBERATION OF ERYTHROMYCIN AND PREPARATION OF ITS SALTS
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The present invention relates to a novel process for the liberation of Erythromycin from Erythromycin salts such as Erythromycin thiocyanate using water as a solvent in presence of a base. Erythromycin obtained by process of the present invention has purity of more than 95%. The present invention further relates to a novel process for the preparation of Erythromycin Stearate by reacting Erythromycin or its salts with stearic acid in presence of water.
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Page/Page column 12
(2014/09/29)
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- Benzoyl Peroxide Composition, Methods for Making Same, and Pharmaceutical or Cosmetic Formulations Comprising Same, and Uses Thereof
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The present invention relates to the preparation of compositions comprising benzoyl peroxide, with or without other additional active ingredients. The process involves introducing benzoyl peroxide, along with any other active ingredients present, into a fatty substance that contains and protects the ingredients that would otherwise be unstable when in contact with one another. The composition is designed to allow all ingredients to become available for skin contact or skin absorption when the fatty substance softens and/or melts as the composition is applied to the skin. The benzoyl peroxide may be pre-micronized to a particle distribution size of about d90 of 0.1 to 150 microns, preferably d90 of 10 to 15 microns. Further, pharmaceutical or cosmetic ingredients may be contained within the fatty substances, with or without, benzoyl peroxide therein or may be present outside of the fatty substance but elsewhere within formulated pharmaceutical or cosmetic products using the active ingredients protected by the fatty substance. These compositions are useful in aqueous-based formulations to treat diseases by topical, transdermal and/or subcutaneous administration.
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- CRYSTALLIZING METHOD OF ERYTHROMYCIN
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The present invention provides an erythromycin crystallizing method, which comprises using dichloromethane containing solvent as a preparation solvent, and the dichloromethane solution of erythromycin received was gradiently cooled from high temperature down to low temperature, and thus making erythromycin crystallize. According to the method of the present invention, the content of erythromycin A is high, the content of erythromycin A in the erythromycin crystalline is more than 94.5% (HPLC detection method), the content of dichloromethane in the erythromycin crystalline is less than 600 ppm, the content of water in the erythromycin crystalline is less than 2.5%, the microbiological titre of the erythromycin crystalline is more than 940μ/mg.
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Page/Page column 3
(2011/07/30)
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- METHOD OF PREPARING CLARITHROMYCIN
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This invention discloses a method of manufacturing clarithromycin, where an erythromycin A 9-oxime thiocyanate salt is used directly to perform an etherification reaction, and then successively silanizattion, methylattion and hydrolysis reactions are sequentially conducted. It is a new process with simple process with a high yield, low cost, less pollution, high quality and is suitable for commercial manufacturing.
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Page/Page column 3
(2010/12/29)
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- Process for the preparation of clarithromycin
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The present invention includes a process involving a one-pot reaction for preparing erythromycin 9-oxime salt comprising: (a) reacting erythromycin thiocyanate with an ammonium source to obtain erythromycin free base; (b) oximating the C-9 carbonyl of the erythromycin free base by reacting the erythromycin free base with triethylamine and hydroxyl amine hydrochloride to form erythromycin oxime; and (c) reacting the erythromycin oxime obtained in step (b) with an ammonium source to obtain the erythromycin 9-oxime salt. The present invention is also drawn to a one-pot reaction for preparing clarithromycin starting with the one-pot reaction for preparing erythromycin 9-oxime salt, further comprising after step (c): (d) silylating the hydroxy groups at the oxime group, and the 2′ and 4″ positions of the erythromycin 9-oxime salt to obtain a silylated derivative; (e) methylating the hydroxy group at the 6 position of the silylated derivative using at least one methylating agent in the presence of at least one inorganic base to obtain SMOP, wherein SMOP is 6-O-methyl-2′,4″-bis(trimethylsilyl)-erythromycin A 9-O-(2-methoxyprop-2-yl)oxime; and (f) converting the SMOP into clarithromycin using at least one deoximating agent in the presence of aqueous ethanol.
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Page/Page column 4-6
(2009/04/24)
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- A PROCESS FOR PREPARING 6,9-IMINO ETHER
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A process for preparing 6,9-Imino ether from Erythromycin thiocyanate without isolating Erythromycin base and Erythromycin oxime and Beckmann's rearrangement of erythromycin oxime is carried in the presence biphasic solvent system comprising methylene chloride and water in the presence of triethylamine along with sodium bicarbonate to obtain 87-96 % pure 6,9-Imino ether. Further the 6,9-Imino ether is hydrogenated to 9-Deoxo-9a-aza-9a-homoerythromycin A followed by reductive methylation to obtain Azithromycin dihydrate.
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Page/Page column 11
(2008/06/13)
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- Amido macrolides
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Various macrolide compounds such as those having the following formulas are provided where the variables have the values provided herein.
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- From (E)- and (Z)-ketoximes to N-sulfenylimines, ketimines or ketones at will. Application to erythromycin derivatives
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Reactions of (E)- and (Z)-ketoximes with trialkylphosphines and diphenyl disulfide (PhSSPh) have been compared to gain insight into the mechanisms involved and their potential applications. N-Sulfenylimine isomers and ketimines have been spectroscopically characterised. Both the E and Z isomers of erythromycin A oxime, when treated with Bu3P and PhSSPh (1:4:8 ratio), give the same N-phenylsulfenyl ketimine (of configuration E) as the major compound, whereas with Bu3P or Me3P and PySeSePy (1:8:4 ratio) afford the imine in good yield. Clarithromycin oxime behaves similarly.
- Esteban, Jorge,Costa, Anna M.,Urpí, Fèlix,Vilarrasa, Jaume
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p. 5563 - 5567
(2007/10/03)
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- Derivatives of erythromycin, clarithromycin, roxithromycin or azithromycin with antibiotic and mucolytic activity
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A pharmaceutical with an enhanced pharmaceutical profile comprises a mucolytic and an antibiotic in which the mucolytic is present in an amount of greater than one molar equivalent of the antibiotic. The antibiotic may be selected from Erythromycin, Roxithromycin, Clarithromycin, Azithromycin, Dirithromycin; and pharmaceutically acceptable salts or esters thereof. The mucolytic is a mucolytically active thiol, especially N-acetylcysteine, mercaptoethanesulfonic acid, tiopronin or methylcysteine. The adducts can be isolated via a simple and efficient process.
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- 9-hydrazone and 9-azine erythromycin derivatives and a process of making the same
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Disclosed are 9-hydrazone erythromycin and 9-azine erythromycin derivatives and the processes for making the same. The compounds are useful intermediates for conversion into 6-O-alkyl erythromycin. Also disclosed are the processes for converting the compounds into 6-O-alkyl erythromycin.
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- Chemical synthesis of 6-O-alkyl erythromycin A
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A process of preparing 6-O-alkyl erythromycin A is provided. The process includes the steps of protecting the oxime hydroxyl of 9-oxime erythromycin A with a benzoyl protecting group, protecting the 2'-hydroxyl group and optionally the 4'-hydroxyl group with an O-protecting group, alkylating the 6-hydroxyl, removing the benzoyl and O-protecting groups and deoximating the 9-oxime.
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- SYNTHESIS OF ERYTHROMYCIN RELATED MACROLIDES
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The synthesisand characterization of a number of macrolides, structurally related with erythromycin, is described.These derivatives have been previously investigated for thier ability to induce contractions and to displace bound motilin in rabbit duodenum.
- Paesen, Jos,Roets, Eugene,Janssen, Gerard,Busson, Roger,Cachet, Thierry,Hoogmartens, Jos
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p. 205 - 212
(2007/10/03)
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- Application of highly stereocontrolled glycosidations employing 2,6-anhydro-2-thio sugars to the syntheses of erythromycin A and olivomycin A trisaccharide
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The highly efficient syntheses of the erythromycin A (1) from its aglycon, (9S)-9-dihydroerythronolide A (4), and the C-D-E trisaccharide 3 of olivomycin A have been accomplished by the successful application of stereocontrolled glycosidations using 2,6-anhydro-2-thio sugars. The former synthesis includes the highly α-stereoselective glycosidation of the C5 desosaminated lactone 12 with phenyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-1,2-dithio-L-altropyranos ide (10), which was achieved by using NIS-TfOH. The latter synthesis involves both the highly β-stereoselective glycosidation of 1,3-di-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranose (23), which was realized by employing TMSOTf, and the highly α-stereoselective glycosidation of phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl- 1,2-dithio-L-manno-pyranoside (24), which succeeded by utilizing NBS. Hydrogenolyses using Raney Ni as a catalyst and selective deprotections of the key glyco substances 17 and 22 led to the total syntheses of erythromycin A (1) and the C-D-E trisaccharide 3 of olivomycin A, respectively.
- Toshima, Kazunobu,Nozaki, Yuko,Mukaiyama, Satsuki,Tamai, Tetsuro,Nakata, Masaya,Tatsuta, Kuniaki,Kinoshita, Mitsuhiro
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p. 3717 - 3727
(2007/10/02)
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- Application of efficient glycosylation of 2,6-anhydro-2-thio sugar to the total synthesis of erythromycin A
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The total synthesis of erythromycin A (1) from (9S)-9-dihydroerythronolide A (2) was achieved efficiently by the highly stereoselective and powerful glycosylation of 2,6-anhydro-2-thio sugar 9 as a key step.
- Toshima,Mukaiyama,Yoshida,Tamai,Tatsuta
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p. 6155 - 6158
(2007/10/02)
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- Erythromycin derivatives and compositions and use for inhibiting virus replication and disease
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Erythromycin derivatives of the formula wherein:, T is OH or a pharmaceutically acceptable organic substituent attached to C5 through an oxygen;, V is OH or a pharmaceutically acceptable organic substituent attached to C3 through an oxygen;, U is hydrogen, hydroxy, or alkoxy or acyloxy of from 1 to 10 carbons, or U at C6 and an H at C7 are removed to form a double bond between C6 and C7, or U is taken together with X to define an ether bridge between C6 and C9;, Y is hydrogen, hydroxy, alkoxy or acyloxy of from 1 to 10 carbon atoms, a sulphate or sulfonate group bonded to C11 through an oxygen atom, -OCH2SO2CH3, or -OCH2SOCH3; Y and H at C10 are removed to form a double bond between C10 and C11; or Y and W, when taken together with C9, C10 and C11 of the macrolide ring, represent a 5- to 7-membered heterocyclic ring; and Z, X and W independently represent hydrogen, hydroxy, or acyloxy or alkoxy of 1 to 10 carbon atoms; with the provision that X and W taken together with U as defined above; W can be taken together with Y as defined above; or Z can be taken together with a hydrogen on C13 to represent a double bond; are used in the prevention and treatment of diseases caused by viruses, especially retroviruses and hepadna viruses. Preferred derivatives are oximinoethers or vinyl ethers or have specified substituents in the macrolide or sugar rings.
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- The Chemistry od Erythromycin. Reactions of Erythromycin A Imine and its 6-Methyl Ether with Aldehydes and Hydrazines
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Erythromycin imine (3) and its 6-methyl ether (6) are multifunctional N-unsubstituted imines, which, in contrast to most unsubstituted imines, are readily isolable and relatively stable towards hydrolysis.With aldehydes in ethanol, the imines react quite differently: the imine (3) reacts with aliphatic and aromatic aldehydes to give predominantly the 9,11-cyclic imines (9), whereas the ether (6) reacts with aliphatic aldehydes to give N-(1-ethoxyalkyl)imines (13) and with benzaldehyde to give a 9,12-epoxy Schiff's base derivative (12).The imines also differ in their reactivities towards hydrazine derivatives: the imine (3) readily reacts with monosubstituted hydrazines to form erythromycin hydrazone derivatives, whereas the ether (6), in common with erythromycin (1), is unreactive towards these reagents.A rationale for the different modes of reaction of compounds (3) and (6) is discussed.
- Davies, J. Sydney,Hunt, Eric,Zomaya, Iskander I.
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p. 1409 - 1414
(2007/10/02)
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- Preparation for prophylaxis and treatment of myiases of animals
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The present invention relates to the art of veterinary science. The preparation for prevention and treatment of myiases of animals comprises the following components, percent by mass: an insecticide exhibiting a larvicidal effect: 1.4 to 2.3 a 5-10% ethanolic solution of polyvinylbutyral and a resol-type phenolformaldehyde resin taken in a ratio of 1:10-45: 16 to 35.0 a plastifying agent improving elasticity of the resulting polymeric film: 1.0 to 20.0 an antibiotic: 0.1 to 0.7 an organic solvent: the balance.
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- Erythromycin A silylated compounds and method of use
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Novel O-alkylsilyl derivatives of macrolide antibiotics are disclosed. These compounds have markedly superior taste properties when compared to the corresponding parent compounds.
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- Erythromycin aldobionates
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This invention relates to a novel process for the preparation of Erythromycin aldobionates and novel Erythromycin maltobionates, Erythromycin Cellobionate and Erythromycin mellibionate. The said process comprises converting an alkali metal salt of aldobionic acid into free aldobionic acid, neutralizing the obtained aldobionic acid with Erythromycin base and finally recovering the Erythromycin aldobionate.
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- Method of therapeutically treating warm blooded animals and compositions therefor
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Tissue in warm blooded animals which is damaged and/or infected is treated by administering a therapeutically effective amount of a composition containing a novel catalyst and water soluble catalyst treated lignite. The treatment is also effective in relieving stress and/or shock. In a further variant, warm blooded animals having damaged and/or infected tissue are treated with a composition containing therapeutically effective amounts of at least one antibiotic, the novel catalyst, and the catalyst treated lignite. Novel compositions are provided which contain therapeutic amounts of at least one antibiotic, the catalyst, and the catalyst treated lignite. The novel catalyst and the catalyst treated lignite are prepared by processes described in detail hereinafter.
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