76247-40-0

Usage

InChI:InChI=1/C9H12ClNO5S/c1-9(2)7(8(13)16-4-10)11-5(12)3-6(11)17(9,14)15/h6-7H,3-4H2,1-2H3/t6-,7+/m1/s1

Upstream product

• 49715-04-0 chlorosulfuric acid chloromethyl ester 
• 68373-14-8 sulbactum 
• 593-71-5 Chloroiodomethane 
• 144-55-8 sodium hydrogencarbonate 
• 76350-35-1 potassium penicillanate 1,1-dioxide 
• 76350-37-3 chloromethyl 6α-chloropenicillanate 1,1-dioxide 
• 69388-84-7 sodium sulbactam 
• 74-97-5 chlorobromomethane 
• 688-73-3 tri-n-butyl-tin hydride 
• 7439-96-5 manganese 
• 84458-09-3 chloromethyl 6,6-dibromopenicillanate 1,1-dioxide 
• 7440-48-4 cobalt 

Downstream Products

• 84519-07-3 6'-(2-Benzyloxycarbonylamino-2-phenylacetamido)-penicillanoyloxymethyl Penicillanate 1,1-Dioxide 
• 103063-56-5 6'-(2-[4-nitrobenzyloxycarbonylamino]-2-[4-hydroxyphenyl]acetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide 
• 103063-55-4 6'-(2-[4-Nitrobenzyloxycarbonylamino]-2phenylacetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide 
• 76247-39-7 iodomethyl penicillanate 1,1-dioxide 
• 84519-06-2 6'-(2,2-dimethyl-4-phenyl-5-imidazolidinon-1-yl)-penicillanoyloxymethyl penicillanate 1,1-dioxide 

Relevant academic research and scientific papers

Synthesis method and application of amoxicillin and sulbactam hybrid molecule

The invention discloses a synthesis method and application of an amoxicillin and sulbactam hybrid molecule, and belongs to the technical field of organic synthesis. According to the method, chlorobromomethane is used as a chloromethyl reagent of sulbactam acid, so that the yield of a key intermediate sulbactam chloromethyl ester is effectively increased, and sulbactam chloromethyl ester and (Z)-6-(2-(4-hydroxyphenyl)-2-((4-methoxy-4-oxobutyl-2-ene-2-yl) amino) acetamido)-3, 3'-dihydroxyl-7-oxo-4-sulfo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid as a raw material to carry out condensation reaction, and a protecting group is removed by using strong acid, so as to prepare the amoxicillin and sulbactam hybrid molecule. The synthesis method has the advantages of mild reaction conditions, cheap and easily available raw materials, low preparation cost, good safety, simple and feasible process and high product yield.

Procedure for the preparation of dioxopenicillanic acid derivatives

Procedure for the preparation of dioxopenicillanic acid derivatives and its salts pharmaceutically acceptable with general formula I, where, R is hydrogen, alkyl group containing 1 to 5 Carbon atoms or a residue of type -CH2R', where R' is hydrogen, halogen or a p-toluensulfonyl group. These are prepared by treatment of the compounds of general formula II, where R is as previously defined and X may be hydrogen or bromine, with a metallic reagent constituted by a mixture or alloy of copper and/or cobalt and/or manganese with iron and/or nickel in an aqueous/organic medium. These compounds are useful as inhibitors of beta-lactamase.

Procedure for the preparation of dioxopenicillanic acid derivatives

Procedure for the preparation of dioxopenicillanic acid derivatives and its salts pharmaceutically acceptable with general formula I, where, R is hydrogen, alkyl group containing 1 to 5 Carbon atoms or a residue of type -CH2R ', where R ' is hydrogen, halogen or a p-toluensulfonyl group. These are prepared by treatment of the compounds of general formula II, where R is as previously defined and X may be hydrogen or bromine, with a metallic reagent constituted by a mixture or alloy of copper and/or cobalt and/or manganese with iron and/or nickel in an aqueous/organic medium. These compounds are useful as inhibitors of beta-lactamase.

Antibacterial 6'-(2-amino-2-[4-acyloxyphenyl]acetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide compounds

6-(2-Amino-2-[4-acyloxyphenyl]acetamido)penicillanoyloxymethyl esters of penicillanic acid 1,1-dioxide are useful as antibacterial agents. Derivatives of the aforesaid antibacterial agents which have an amino protecting group on the amino function in the 2-amino-2-(4-acyloxyphenyl)acetamido side chain are useful intermediates to the antibacterial agents themselves.

Process and intermediates for preparation of 1,1-dioxopenicillanoyloxymethyl 6-beta-aminopenicillanate

A process for the preparation of 1,1-dioxopenicillanoyloxymethyl 6-beta-aminopenicillanate which comprises reacting 1,1-dioxopenicillanoyloxymethyl 6-phenylacetamidopenicillanate or the corresponding phenoxyacetamidopenicillanate under anhydrous conditions with a halogenating agent in the presence of a reaction inert solvent to form an intermediate imino halide, addition of a primary alcohol having from one to four carbon atoms to convert the imino halide to an imino ether and subsequent hydrolysis to give the desired product.

1,1-Alkanediol dicarboxylate linked antibacterial agents

Useful antibacterial agents in which a penicillin and/or a beta-lactamase inhibitor are linked via 1,1-alkanediol dicarboxylates are of the formula STR1 where A is the residue of certain dicarboxyic acids, R3 is H or (C1 -C3), n is zero or 1 such that when n is zero R is P or B and R1 is the residue of certain esters, H or a salt thereof; and when n is 1, one of R and R1 is P and the other is B, and P is STR2 where R2 is H or certain acyl groups, and B is the residue of a beta-lactamase inhibiting carboxylic acid; a method for their use, pharmaceutical compositions thereof and intermediates useful in their production.

Crystalline benzenesulfonate salts of sultamicillin

Novel benzenesulfonic acid addition salts of sultamicillin of the formula STR1 and hydrated forms thereof, where X is hydrogen or chloro, especially the crystalline dihydrate salts, having advantages over the prior art forms of sultamicillin in pharmaceutical dosage forms, most particularly those for use in pediatric medicine, method for their use and pharmaceutical compositions thereof.

Bis-esters of dicarboxylic acids with amoxicillin and certain hydroxymethylpenicillanate 1,1-dioxides

Antibacterial bis-esters of 1,4-cyclohexanedicarboxylic acids and alkane dicarboxylic acids wherein the ester moieties are derived from different alcohols; one alcohol being hydroxymethylpenicillanate 1,1-dioxide, or the 6-beta-hydroxymethyl or the 6-alpha-aminomethyl derivative thereof; and the other being 6-[D-(2-amino-2-(p-hydroxyphenyl)acetamido)]penicillanic acid (amoxicillin); and pharmaceutically acceptable salts thereof; a method for the use of said esters and their salts, and methods for their preparation.

Preparation of halomethyl esters (and related esters) of penicillanic acid 1,1-dioxide

Process for preparation of halomethyl esters (and related esters) of penicillanic acid 1,1-dioxide of the formula STR1 where X is Cl, Br, I, certain alkylsulfonyloxy or arylsulfonyloxy groups, useful as intermediates in production of antibiotics having beta-lactamase activity, which comprises hydrogenolysis of an ester of the formula STR2 where n is zero, 1 or 2; Y and Z are each Cl, Br or I, or Y is H and Z is Cl, Br, I, C N-- or SCN--, or Y is arylselenyl and Z is Cl or Br; and when n is zero or 1, oxidation of the hydrogenolysis product; a process for preparing compounds of formula (VI, n=2) by oxidation of the corresponding compound (VI) wherein n is zero or 1, and certain novel intermediates useful in the above processes.