- Synthesis of terramycin
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The present invention relates to the synthesis of terramycin, specifically (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-13-[[3S,4S,6R,8R]-8-methoxy-4,8-dimethyl-1,5-dioxa snail [2,5]octyl-6-yl]oxo) 3,5,8,10,12,14-hexamethyl-11-[3,4, 6-Tr
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Paragraph 0020-0021
(2022/01/08)
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- Preparation method of tulathromycin
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The invention relates to a synthetic method of tulathromycin. Under the action of illumination and a specific catalytic system, rapid, efficient and pollution-free synthesis of tulathromycin is realized. Compared with the existing synthetic method, the synthetic method provided by the invention is simple to operate, mild in condition and capable of meeting the requirement of large-scale industrial production.
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Paragraph 0022-0033
(2021/05/05)
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- Preparation method for tulathromycin
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The invention provides a preparation method for tulathromycin, and belongs to the technical field of drug synthesis. The method comprises the following steps: mainly by using dihydroerythromycin (9-deoxo-9a-aza-9a-homoerythromycin A) as a raw material, performing a hydroxyl protection reaction, performing a selective oxidation reaction of 4'-hydroxyl to generate a ketone, performing an epoxidationreaction to generate an epoxide, performing deprotection, and performing a ring-opening reaction to introduce n-propylamine to generate the target product tulathromycin. In the method, an oxidizing agent for the selective oxidation reaction of the 4'-hydroxyl is hydrogen peroxide or a Dess-Martin periodinane, so that the method avoids the use of equivalent or excessive amounts of a high-valent metal oxidizing agent, has low costs and mild reaction conditions, and improves the yield and purity of the product.
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- Preparation method of tulathromycin
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The invention provides a preparation method of tulathromycin, and belongs to the field of pharmaceutical chemicals. The method comprises the following steps of: reacting azithromycin serving as a rawmaterial with phenyl chloroformate to protect hydroxyl to obtain protected nitrogen azithromycin, oxidizing the hydroxyl into a ketone group by oxidation, epoxidizing, deprotecting, and reacting withn-propylamine to obtain tulathromycin. The product produced by the method has the characteristics of high purity, high yield, low cost, simple operation and stable process.
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Paragraph 0058-0060
(2020/04/02)
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- Method for synthesizing oxytetracycline and oxytetracycline phosphate (by machine translation)
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Step A product shown in Formula is obtained by dissolving, a product of: Formula I with a product shown by subjecting a product shown II in Formula to a reaction; to obtain a product having a hydroxyl: protection product II as shown in Formula I, and a ca
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Paragraph 0052-0056
(2020/04/22)
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- METHOD AND INTERMEDIATE FOR PREPARING TULATHROMYCIN
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A method and an intermediate for preparing a tulathromycin. The method includes the following step: in an organic solvent, subjecting a compound represented by formula (II) and an n-propylamine to a ring-opening addition shown below to obtain a tulathromycin represented by formula (I), wherein the organic solvent is a 1,2-propandiol. Tulathromycin obtained using the method has a high purity, with an HPLC purity being 95% and above, and up to 99% and above, satisfying a required purity for preparing a tulathromycin as a pharmaceutical formulation. The method has a high yield, is simple to operate, and is more suitable for industrial production.
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Paragraph 0074; 0075; 0076; 0084; 0085
(2019/02/05)
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- Method for preparing tulathromycin
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The invention relates to a novel method for preparing tulathromycin. The method includes the steps that 3,4-acetonylidene protected demethylazithromycin is used as a starting material, a 2-hydroxyl group is firstly protected, then a 4-hydroxyl group is oxidized to a carbonyl group under Swern conditions, TMSCN is used for performing a cyano group addition reaction on the carbonyl group under the action of TBAF, a resulting intermediate compound is subjected to a hydrogenation reaction in the presence of HOAc with Pd/C as a catalyst, the cyano group in the compound is converted into an amine methyl group while a 2-hydroxy group protecting group and 3,4-acetonylidene protection are removed, and finally under the action of base, an amine methyl compound is reacted with 1-halogenated propane to achieve the preparation of tulathromycin.
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- Tulathromycin oxalate
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The invention discloses salt of tulathromycin, particularly oxalate, a preparation method of tulathromycin oxalate and application of tulathromycin oxalate to preparation of tulathromycin.
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- Salt for tulathromycin intermediate
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The invention discloses a salt for preparing a tulathromycin intermediate, and particularly relates to oxalate and a preparation method thereof as well as application of the oxalate in a method for preparing tulathromycin.
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- A synthetic Alterra cephalosporin new route
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The invention discloses a new route for synthesizing tulathromycin. The new route for synthesizing the tulathromycin is different from the previous epoxidation reaction, ring-opening reaction and the like reaction process. The new route for synthesizing the tulathromycin uses Passerini reaction, all the groups are led in by one time, and then the tulathromycin is obtained through Clemmensen reaction and hydrogenation reduction reaction. The new route for synthesizing the tulathromycin includes steps that taking hydroxyl protecting demethylation azithromycin, generating hydroxyl protecting ketone (compound I) through oxidation reaction, leading amido bond and cyclopropyl to a ketone-hydroxyl group position, generating (compound II), reducing the hydroxyl into methylene through Clemmensen reaction, generating (compound III), carrying out hydrogenation and ring opening on cyclopropyl to generate n-propyl through ring-opening reaction, and obtaining the tulathromycin (compound IV). The new route for synthesizing the tulathromycin is simple in process, easy to implement, easy to obtain reaction reagent, moderate in reaction condition, high in selectivity, less in by-product, easy to purify and low in facility request.
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Paragraph 0072-0074
(2017/11/16)
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- Animal antibiotiki Alterra ycin preparation method
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The invention belongs to the technical field of organic synthesis and pharmaceutical chemistry and especially relates to a preparation method of an animal antibiotic tulathromycin. According to the preparation method, azithromycin A and acetic anhydride which are used as raw materials are subjected to protection and oxidation to obtain oxide cyclic ketone; the intermediate is used for innovative addition of cyclic ketone and nitromethane; an addition product is reduced to obtain methyleneamine; direct condensation between methyleneamine and propionaldehyde is carried out; and reduction is conducted to obtain the high-purity target compound. Raw materials which are cheap and easily available are adopted. The preparation method has advantages of simple reaction, easily-controlled reaction process, high product purity, manageability, high yield, low cost and the like, and is suitable for large-scale industrial production.
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Paragraph 0037; 0042; 0043; 0048; 0049; 0054; 0055
(2019/02/02)
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- A Alterra rhzomorph method for the synthesis of (by machine translation)
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The invention relates to the field of organic synthetic chemistry and specifically relates to a synthetic method of tulathromycin. No Cbz (carbamazepine)-Cl protection is used in the synthetic method of tulathromycin, which is provided by the invention; no Pd/C-H2 system needs to be used for deprotection; therefore, the operation is safer; besides, the reaction does not need to be carried out at an ultralow temperature, so that the energy source is saved; moreover, dimethylsulfide generated in the reaction process can be recovered and reused, so that the cost is relatively low; the reaction only comprises three steps, which is simpler than that in the known documents.
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- Zymoid intermediate and its preparation method and Alterra MYCIN preparation method
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The invention provides a tulathromycin intermediate, a preparation method of the tulathromycin intermediate, and a preparation method of the tulathromycin. The preparation method of the tulathromycin has the advantages of mild condition, convenience for operation, and low cost. The preparation method of the tulathromycin comprises the following steps of: using azithromycin A as a raw material; protecting 2'-hydroxy and 6'-amino in the azithromycin A through di-tert-butyl dicarbonate so as to obtain double-protective azithromycin A; carrying out Swern oxidation to 4''-hydroxy to the double-protective azithromycin A; salifying along with trifluoroacetic acid; and synchronously removing boc t-butyloxycarbonyl to obtain the azithromycin A bitrifluoroacetic acid salt of 4''-carbonyl; and then reacting with trimethylsulfonium bromide to obtain 4''-epoxy compound; and finally carrying out nucleophilic addition on the 4''-epoxy compound by n-propylamine so as to obtain the phosphate of tulathromycin; and further neutralizing via alkaline to obtain the target compound tulathromycin; and synchronously obtaining the tulathromycin intermediate of azithromycin A bitrifluoroacetic acid salt of 4''-carbonyl.
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- PROCESS FOR PREPARATION OF TULATHROMYCIN
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The present invention discloses a novel process for preparation of tulathromycin. The process uses fewer steps due to a more direct route without prior protection of functional groups of the compound of formula (I).
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- NOVEL PROCESS FOR THE PREPARATION OF 9-DEOXO-9A-AZA- 9A-HOMOERYTHROMYCIN A MODIFIED IN THE C-4'' OF THE CLADINOSE RING BY AN EPOXIDE GROUP
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The present invention concerns a process for the preparation of the compound of formula (1). The compound of formula (1) is the key intermediate in the synthesis of some antibacterial agents of the triamilide class, such as Tulathromycin, useful to treat bacterial and protozoa infections.
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- Synthesis and activity of a novel class of tribasic macrocyclic antibiotics: The triamilides
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The stereoselective synthesis of two novel series of tribasic macrocyclic antibiotics with potent in vitro activity against Pasteurella multocida and Escherichia coli strains of bacteria is described. The in vitro activity can be significantly influenced
- Letavic, Michael A.,Bronk, Brian S.,Bertsche, Camilla D.,Casavant, Jeffrey M.,Cheng, Hengmiao,Daniel, Kirsten L.,George, David M.,Hayashi, Shigeru F.,Kamicker, Barbara J.,Kolosko, Nicole L.,Norcia, Laura J.L.,Oberton, Vanessa D.,Rushing, Margaret A.,Santoro, Sheryl L.
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p. 2771 - 2774
(2007/10/03)
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- Process for preparing 4"-substituted-9-deoxo-9a-aza-9a-homoerythromycin A derivatives
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The invention relates to processes for preparing compounds of formula 1 ???wherein R3 is as defined herein, and to pharmaceutically acceptable salts thereof, as well as intermediates useful in such processes. The compounds of formula 1 are antibacterial agents that may be used to treat various bacterial and protozoa infections. The invention also relates to pharmaceutical compositions containing compounds prepared by the processes of the invention and to methods of treating bacterial protozoa infections by administering such compounds.
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