Synthesis of cephalosporin compounds

US10125149B2 · US · B2

Patent metadata
FieldValue
Publication numberUS-10125149-B2
Application numberUS-201515503907-A
CountryUS
Kind codeB2
Filing dateAug 14, 2015
Priority dateAug 15, 2014
Publication dateNov 13, 2018
Grant dateNov 13, 2018

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  1. Title

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  2. Abstract

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  3. Assignees and inventors

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  4. Key dates

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  5. First independent claim

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  6. CPC / IPC classifications

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  7. Citations and related patents

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Abstract

Official abstract text for this publication.

Provided herein is a method for the synthesis of cephalosporin antibiotic compounds comprising a palladium-catalyzed coupling reaction. Provided herein are methods for the synthesis of cephalosporin compounds of formula (I) employing a palladium-catalyzed alkylation reaction, as well as compositions related to the same. In an aspect, provided herein is a method for preparing a compound of formula (II), or a salt thereof, comprising the step of admixing, e.g., reacting, a compound of formula (III), or a salt thereof, with a nucleophile (Nuc) in the presence of reagents comprising: (a) a palladium source; and (b) a palladium-binding ligand, to form a compound of formula (II), or a salt thereof.

First claim

Opening claim text (preview).

What is claimed is: 1. A composition comprising a compound of formula (Va): and from about 0.01 ppm to about 5 ppm palladium, wherein A ⊖ is a pharmaceutically acceptable anion selected from chloride, bromide, iodide, sulfate, bisulfate, toluenesulfonate, methanesulfonate, edisylate, maleate, phosphate, ketoglutarate, acetate, trifluoroacetate, and trifluoromethanesulfonate. 2. The composition of claim 1 , which comprises from about 0.01 ppm to about 3 ppm palladium. 3. The composition of claim 1 , which comprises from about 0.01 ppm to about 2 ppm palladium. 4. The composition of claim 1 , which comprises from about 0.01 ppm to about 1 ppm palladium. 5. The composition of claim 1 , wherein A ⊖ is chloride. 6. The composition of claim 1 , wherein A ⊖ is bisulfate. 7. The composition of claim 1 , wherein A ⊖ is acetate. 8. The composition of claim 1 , wherein A ⊖ is trifluoroacetate. 9. A composition comprising a compound of formula (VII): and from about 0.01 ppm to about 5 ppm palladium. 10. The composition of claim 9 , which comprises from about 0.01 ppm to about 3 ppm palladium. 11. The composition of claim 9 , which comprises from about 0.01 ppm to about 2 ppm palladium. 12. The composition of claim 9 , which comprises from about 0.01 ppm to about 1 ppm palladium. 13. A composition comprising a compound of formula (VII): and from about 0.01 ppm to about 1 ppm palladium.

Assignees

Inventors

Classifications

  • C07D501/56Primary

    with the 7-amino radical acylated by carboxylic acids containing hetero rings · CPC title

  • from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents · CPC title

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What does patent US10125149B2 cover?
Provided herein is a method for the synthesis of cephalosporin antibiotic compounds comprising a palladium-catalyzed coupling reaction. Provided herein are methods for the synthesis of cephalosporin compounds of formula (I) employing a palladium-catalyzed alkylation reaction, as well as compositions related to the same. In an aspect, provided herein is a method for preparing a compound of formu…
Who is the assignee on this patent?
Merck Sharp & Dohme
What technology area does this patent fall under?
Primary CPC classification C07D501/56. Mapped technology areas include Chemistry & Metallurgy.
When was this patent published?
Publication date Tue Nov 13 2018 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
What related patents are in patentsdb?
We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).