- Preparation method of azithromycin (by machine translation)
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After the reaction temperature is, the reaction temperature of A is adjusted 0 °C to, for NaHCO3 hours, and then the reaction solution is evaporated and dried, 1 by suction filtration, at NaOH. degree. C. for PH hours to obtain a white solid 11 - 12, which is dissolved in an ethanol solution 3 and subjected to suction filtration to obtain a white solid . The invention discloses a 2h preparation method, of azithromycin in an ethanol solution after reaction, A; hours to carry out suction filtration; to A g of the toluene, sulfonyl. chloride, obtained 10 °C. (by machine translation)
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Paragraph 0006
(2020/04/17)
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- NOVEL ANTI-INFECTIVE AND ANTI-INFLAMMATORY COMPOUNDS
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Lysosomally accumulated substances that release a nitroxy group, or a short chain fatty acid or a product of anaerobic metabolism or a thiol or a sulfide often from an ester or similar labile linkage have anti-inflammatory, anti-cancer and anti-bacterial activity. They are useful in treating infectious, inflammatory and malignant disease.
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Page/Page column 100
(2018/09/20)
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- Mild, calcium catalysed Beckmann rearrangements
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A mild calcium catalysed Beckmann rearrangement has been realised, which forgoes the more traditional harsh reactions conditions associated with the transformation. The catalyst system is shown to be tolerant towards a wide variety of functional groups relevant to natural product synthesis and medicinal chemistry and the synthetic utility of the reaction has also been investigated. A preliminary mechanistic investigation was performed to understand the nature of the incoming nucleophile and a possible reaction pathway is described.
- Kiely-Collins,Sechi,Brennan,McLaughlin
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p. 654 - 657
(2018/02/06)
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- Preparation method of norazithromycin
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The invention discloses a preparation method of norazithromycin and relates to the technical field of macrolide antibiotics. The preparation method comprises the following steps: reducing erythrocin A 6,9-imino ether in water at 0 DEG C to room temperature under the pH of 7.0-9.0 by using a reducing agent sodium borohydride or potassium borohydride; then in the presence of an organic solvent and water, performing continuous hydrolysis at 0 DEG C to room temperature under the pH of 2.0-3.0; then adding two-phase reaction liquids after continuous hydrolysis into an alkaline aqueous solution, adjusting the pH to be greater than or equal to 12, stirring, layering and abandoning the aqueous phase, wherein the organic solvent is dichloromethane, chloroform, 1,2-dichloromethane, ethyl acetate or butyl acetate; and after the last hydrolysis reaction in continuous hydrolysis, performing layering, directly adding the aqueous phase into the alkaline aqueous solution, adjusting the pH to be greater than or equal to 12, and performing stirring and separating out norazithromycin. The method increases the utilization ratio of the reducing agent, can control reverse reactions of borate, and reduces unnecessary separating process to obtain high quality norazithromycin.
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- Method for synthesizing azithromycin
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The invention relates to a method for synthesizing azithromycin. According to the invention, erythromycin thiocyanate is adopted as an initial raw material of an oximation reaction, such that erythromycin oxime thiocyanate is obtained; the next step of reaction is directly carried out; and through rearrangement, reduction and methylation reactions, azithromycin is obtained. The rearrangement and reduction reactions are carried out with a one-pot method. A reduction reaction product is not separated in a solid form, and is directly used in the methylation reaction. With the synthesizing method provided by the invention, a conversion process from erythromycin oxime thiocyanate to eythromycin oxime is eliminated, and steps that rearrangement and reduction products are separated in solid forms in an original process are also eliminated. The process is environment-friendly and simple, and has the advantages of high yield, low cost, low pollution and high product purity. The method is suitable for industrialized productions.
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- AZITHROMYCIN ANTIMICROBIAL DERIVATIVES WITH NON-ANTIBIOTIC PHARMACEUTICAL EFFECT
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The invention provides molecules, which are based on a modification of azithromycin, removing the antibiotic effect, while retaining other beneficial effects, such as, but not limited to imunomodulatory effects. The compounds of the invention can be described by compounds of Formula (I) as further defined herein.
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- PROCESS FOR THE PURIFICATION OF AZITHROMYCIN BY SEPARATION FROM ITS THERMAL DEGRADATION PRODUCTS AND/OR ISOMERS
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The present invention relates to methods for improving the purity of azithromycin, preferably by purifying azithromycin from degradation products and/or isomers. The invention describes a degradation product of azithromycin which may be produced during drying and/or storage of azithromycin and relates to methods of removing the degradation product(s). The invention further relates to a method for preparing azithromycin dihydrate from crude azithromycin containing the isomer azithromycin B. The invention furthermore relates to a combined process for making azithromycin dihydrate which combines the method for the purification of azithromycin from degradation products with the method for making azithromycin dihydrate which removes the isomer azithromycin B.
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Page/Page column 15
(2011/02/24)
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- COATED PELLETS
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Coated pellets which comprise an active pharmaceutical ingredient that is poorly soluble in water, release at least 80% of the active ingredient under in vitro conditions in phosphate buffer at pH 5.0 after 30 minutes and are bioequivalent to a liquid formulation of the active ingredient under in vitro fed status test conditions and/orare coated with a composition, which includes a lipophilic component (A) and a hydrogel former (B), wherein the pure lipophilic component (A) has (i) an HLB value of ≦5, and/or(ii) a melting range of ≧60° C, and/or(iii) a solidification range Δ of less than 35° C., and/or(iv) a density of ≧0.80 g cm?3.
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- Total synthesis of azithromycin
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The quaternary king: Azithromycin (1), which has improved pharmacological profiles compared with erythromycins, was the target of an enantioselective synthesis. All the stereogenic quaternary carbon centers were elaborated by a desymmetrization of 2-subst
- Kim, Hyoung Cheul,Kang, Sung Ho
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supporting information; experimental part
p. 1827 - 1829
(2009/09/07)
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- A COST EFFECTIVE PROCESS FOR PREPARING 6,9-IMINO ETHER
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The present invention relates to an improved process for the preparation of 6,9-imino ether of formula (I) an intermediate used in preparation of Azithromycin. The present invention further provides a process for preparation of Azithromycin.
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Page/Page column 8
(2010/01/30)
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- Using chemical probes to investigate the sub-inhibitory effects of azithromycin
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The antibacterial drug azithromycin has clinically beneficial effects at sub-inhibitory concentrations for the treatment of conditions characterized by chronic Pseudomonas aeruginosa infection, such as cystic fibrosis. These effects are, in part, the result of inhibition of bacterial biofilm formation. Herein, the efficient synthesis of azithromycin in 4 steps from erythromycin and validation of the drug's ability to inhibit biofilm formation at sub-MIC (minimum inhibitory concentration) values are reported. Furthermore, the synthesis of immobilized and biotin-tagged azithromycin analogues is described. These chemical probes were used in pull-down assays in an effort to identify azithromycin's binding partners in vivo. Results from these assays revealed, as expected, mainly ribosomal-related protein binding partners, suggesting that this is the primary target of the drug. This was further confirmed by studies using a P. aeruginosa strain containing plasmid-encoded ermC, which expresses a protein that modifies 23S rRNA and so blocks macrolide entry to the ribosome. In this strain, no biofilm inhibition was observed. This work supports the hypothesis that the sub-inhibitory effects of azithromycin are mediated through the ribosome. Moreover, the synthesis of these chemical probes, and proof of their utility, is of value in global target identification in P. aeruginosa and other species.
- Glansdorp, Freija G.,Spandl, Richard J.,Swatton, Jane E.,Loiseleur, Olivier,Welch, Martin,Spring, David R.
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supporting information; experimental part
p. 4120 - 4124
(2009/02/07)
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- PROCESSES FOR THE PREPARATION OF AZITHROMYCIN
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The invention relates to processes for the preparation of anhydrous azithromycin. The invention also relates to a one-pot process for the preparation of azithromycin without isolation of intermediates. The invention also relates to pharmaceutical compositions that include the anhydrous azithromycin or a pharmaceutically acceptable salt thereof.
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Page/Page column 12
(2008/06/13)
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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 12-13
(2008/06/13)
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- Process of preparing a crystalline azithromycin monohydrate
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The present invention provides a process of preparing a crystalline azithromycin monohydrate. The process involves dissolving azithromycin in a solution containing ethanol, adding the dissolved azithromycin into water to precipitate the crystals, isolating and drying the precipitate to a water content of about 5% (w/w) to about 7% (w/w). The resulting azithromycin monohydrate is stable, exhibiting less than 2% degradation, and non-hydroscopic.
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Page/Page column 4
(2008/06/13)
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- NOVEL AMORPHOUS 9-DEOXO-9A-AZA-9A-METHYL-9A-HOMOERYTHROMYCIN A, PROCESS FOR PREPARING THE SAME, AND USE THEREOF
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Substantially pure amorphous 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A. In addition, this disclosure is directed to a process for the preparation thereof from crude 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A via orthorhombic isostructural pseudopolymorphs of 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A, of the general formula I x H2O x S I wherein S represents a water-miscible or water-immiscible organic solvent, characterized by the orthorhombic space group P212121, with average unit cell parameters a = 8.2 to 9.7 ?, b = 11.5 to 13.5 ?, c = 44.5 to 47.0 ?, α =β = γ = 90°, wherein a, b and c represent the crystal axes lengths and α, β and γ represent the angles between the crystal axes. In addition, pharmaceutical compositions containing the substantially pure amorphous 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A are disclosed, as well as a method for the treatment of bacterial and protozoal infections, and inflammation related diseases in humans and animals by administration of a pharmaceutical composition containing same.
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- Macrolides
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Azithromycin in the form of a stable monohydrate and processes for the preparation of azithromycin in the form of an, e.g. stable, monohydrate.
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Page/Page column 11
(2008/06/13)
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- An improved process for the preparation of azithromycin monohydrate
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The invention relates to a process for making Azithromycin crystals using a number of process steps that avoids the use of cumbersome and/or inefficient extraction and/or isolation procedures.
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- Novel amorphous 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A, process for preparing the same, and uses thereof
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Substantially pure amorphous 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A. In addition, this disclosure is directed to a process for the preparation thereof from crude 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A via orthorhombic isostructural pseudopolymorphs of 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A, of the general formula I wherein S represents a water-miscible or water-immiscible organic solvent, characterized by the orthorhombic space group P212121, with average unit cell parameters a=8.2 to 9.7 ?, b=11.5 to 13.5 ?, c=44.5 to 47.0 ?, α=β=γ=90°, wherein a, b and c represent the crystal axes lengths and α, β and γ represent the angles between the crystal axes. In addition, pharmaceutical compositions containing the substantially pure amorphous 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A are disclosed, as well as a method for the treatment of bacterial and protozoal infections, and inflammation related diseases in humans and animals by administration of a pharmaceutical composition containing same.
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- Crystal forms of azithromycin
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The invention relates to novel crystal forms of azithromycin, an antibiotic useful in the treatment of infections.
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- Process for preparation of anhydrous azithromycin
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The present invention provides a stable form of azithromycin derivatives that act as antibiotics. These compounds are in anhydrous form and have increased stability over the hydrated forms.
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- Azithromycin preparation in its noncryst alline and crystalline dihydrate forms
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The present invention describes new procedures for the preparation of the macrolide azithromycin in its non-crystalline and crystalline dihydrate forms, which are characterized and clearly differentiated by means of the following methods and techniques: 1. IR Spectroscopy. 2. Differential Scan Calorimetry (DSC). 3. X-Ray Diffraction. 4. Hygroscopicity. 5. Crystallinity test (Light Polarized Microscopy)
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- Macrolide production
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A process for the production of azithromycins by methylation of the nitrogen atom in position 9 of the ring structure in 9-deoxo-9a-aza-9a-homoerythromycins in the presence of formaldehyde and in the presence of a reducing agent in non-halogenated solvent; and azithromycin which is free from halogenated organic solvent in a stable anhydrous form; or in the form of a solvate with non-halogenated solvent with the exception of water.
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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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- Process for the preparation of azithromycin
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The present invention describes a new process for the preparation of azithromycin from a suitable imino ether as precursor, characterised by the fact that the reduction and the reductive methylation of said imino ether are sequentially carried out with a noble metal catalyst and hydrogen in the presence of formaldehyde, or a source thereof, wherein both reactions can be conducted in the same reaction vessel.
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- Preparation of azithromycin
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Azithromycin is prepared from an imino ether by carrying out the reduction and reductive methylation sequentially with a noble metal catalyst and hydrogen in the presence of formaldehyde, or a source thereof, both reactions being conducted in the same reaction vessel.
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- Novel transannular rearrangements of azalide iminoethers
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The transannular reactions between the aglycone hydroxyl groups and the iminoether and lactone groups of the 9a- and 8a-azalide iminoethers 4 and 5 were investigated under a variety of conditions. Translactonization by the 11-hydroxyl groups of 4 and 5 were found to give the corresponding 13-membered iminoethers 21 and 9. The thermal rearrangement of 4 produced an epimeric mixture of the 9,11-iminoethers 15 and 16. Further elaboration of isomer 16 produced 8-epi azithromycin 20. Finally, we have proposed an alternative structure, the amino γ-lactone 25, for one of the reported products (14) from the Beckmann rearrangement of erythromycin A (9E)-oxime 13. An authentic sample of 9a-aza-9a-homoerythromycin A 14 was prepared in three steps from iminoether 4.
- Wilkening, Robert R.,Ratcliffe, Ronald W.,Doss, George A.,Mosley, Ralph T.,Ball, Richard G.
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p. 16923 - 16944
(2007/10/03)
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- Azithromycin and derivatives as antiprotozoal agents
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The use of azithromycin, its 4§-epimer, or the 4§-amino-4§-deoxy analogs thereof in the treatment of systemic protozoal infections in mammals, particularly toxoplasmosis in man; and pharmaceutical compositions therefor.
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- 11-METHYL-11-AZA-4-0-CLADINOSYL-6-0-DESOSAMINYL-15-ETHYL-7,13,14-TRIHYDROXY-3,5,7,9,12,14-HEXAMETHYL-OXACYCLOPENTADECANE-2-ONE AND DERIVATIVES THEREOF
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11-Methyl-11-aza-4-0-cladinosyl-6-0-desosaminyl-15-ethyl-7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl-oxacyclopentadecane-2-one and derivatives thereof, such as the 13,14-carbonate and C1-C3-alkanoyl derivatives thereof. The compounds exhibit antibacterial activity.
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- Epimeric azahomoerythromycin A derivative, intermediates and method of use
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Antibacterial 4"-epi-9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A, pharmaceutically-acceptable salts thereof, pharmaceutical compositions comprising antibacterially-effective amounts thereof, a method of treatment of bacterial infections with antibacterially effective amounts thereof, and intermediates for the synthesis thereof from erythromycin A.
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- N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor
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Antibacterial N-methyl 11-aza-10-deoxo-10-dihydroerythromycin A and pharmaceutically acceptable acid addition salts thereof, intermediates therefor, and processes for their preparation.
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