76646-91-8

Usage

Uses

Used in Pharmaceutical Industry:
(3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE is used as an impurity in the production of the semi-synthetic β-lactamase inhibitor Sulbactam (S699185) for its role in enhancing the effectiveness of certain antibiotics. As an impurity, it is essential to monitor and control its presence to ensure the safety and efficacy of the final pharmaceutical product.
In the context of Sulbactam, (3S)-6,6-DIBROMO-2,2-DIMETHYLPENAM-3-CARBOXYLIC ACID 1,1-DIOXIDE serves as a reminder of the importance of quality control and purity in the pharmaceutical manufacturing process. While it may not have a direct application as a therapeutic agent, its presence in the production of Sulbactam highlights the need for thorough analysis and purification of active pharmaceutical ingredients to maintain the highest standards of patient care.

InChI:InChI=1/C8H9Br2NO5S/c1-7(2)3(4(12)13)11-5(14)8(9,10)6(11)17(7,15)16/h3,6H,1-2H3,(H,12,13)/t3-,6+/m0/s1

Upstream product

• 36091-15-3 (5R,6R)-6-amino-2,2-dimethyl-1,1-dioxopenam-3-carboxylic acid 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 551-16-6 6-Aminopenicillanic Acid 
• 76454-48-3 Sodium 6,6-dibromopenicillanate 
• 205320-24-7 6,6-dibromopenicillanic acid 

Downstream Products

• 121370-36-3 p-methoxybenzyl (3S,5R,6S)-6-bromopenam-3-carboxylate 1,1-dioxide 
• 121370-47-6 p-methoxybenzyl 6-α-allylpenicillanate 1,1-dioxide 
• 68373-14-8 sulbactum 
• 69388-84-7 sodium sulbactam 
• 68373-14-8 sulbactam 
• 666174-87-4 [(1R)-1-(benzoyl)oxy]ethyl (2S,5R,6R)-3,3-dimethyl-6-(hydroxymethyl)-7-oxo-4-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylate-4,4-dioxide 
• 666174-91-0 benzyl (2S,5R,6S)-6-bromo-3,3-dimethyl-6-hydroxymethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4,4-dioxide 
• 76454-56-3 benzyl bromopenicillanate-S,S-dioxide 
• 76454-55-2 6β-bromopenicillanic acid 1,1-dioxide benzyl ester 
• 76454-54-1 benzyl (2S,5R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]-heptane-2-carboxylate-4,4-dioxide 
• 174322-09-9 allyl (6E)-<(1-<2-(4,4'-dimethoxytrityloxy)ethyl>-1,2,3-triazol-4-yl)methylene>penicillanate 1,1-dioxide 
• 174322-08-8 allyl (6Z)-<(1-<2-(4,4'-dimethoxytrityloxy)ethyl>-1,2,3-triazol-4-yl)methylene>penicillanate 1,1-dioxide 
• 305796-55-8 [2S,5R,6R]-3,3-dimethyl-4,4,7-trioxo-6-[6-(4-methylphenylsulfonyl)-isoxazol-3-ylmethyl]-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl 

Relevant academic research and scientific papers

A versatile strategy for the solid-phase synthesis of penicillin derivatives: Efficient preparation of 2β-methyl substituted penams as β-lactamase inhibitor analogues

A convenient solid-phase method for the synthesis of 2β-methyl substituted penicillins using commercially available resins is described. Functionalization of Merrifield and Wang resin bound penam derivatives was performed by penicillin sulfoxide rearrangement and the products were released from the supports under mild conditions. The utility of this methodology has been demonstrated by synthesizing a small library of penicillin derivatives in moderate to very good overall isolated yields for the multistep synthetic sequence. Georg Thieme Verlag Stuttgart.

β-Lactams on solid support: Mild and efficient removal of penicillin derivatives from Merrifield resin using aluminum chloride

Penicillin derivatives linked to Merrifield resin are efficiently released from this support under mild conditions using aluminum chloride in dichloromethane/nitromethane. Extension to Wang resin-linked analogues and studies on the solid-phase oxidation of penicillin is also reported.

Synthesis method of sulbactam

The invention relates to a synthesis method of sulbactam, and belongs to the field of beta-lactamase inhibitor synthesis. In the method, 6-aminopenicillanic acid (6-APA) as a raw material is dissolvedin an organic solvent, and is adopted together with bromine as substrates under a strong acid condition, 6,6-dibromo penicillanic acid is formed through diazotization bromination in a manner of dropwise adding a sodium nitrite solution, and then one-step oxidation and reduction are performed to obtain sulbactam. According to the method, a hydrogen peroxide one-step oxidation mode is adopted, andthe use of potassium permanganate is avoided from the source, so that the generation of waste salt is reduced, and meanwhile, the use of a large amount of ethyl acetate is avoided. The method not onlyreduces the emission of three wastes from the source and greatly reduces the emission of organic matters and waste salt in the original process, but also greatly reduces the side reaction and the rawmaterial cost.

Sulbactam sodium compound containing one-twentieth water and pharmaceutical composition thereof

The invention discloses a sulbactam sodium compound containing one-twentieth water. The sulbactam sodium compound is white crystalline powder, and each mole of sulbactam sodium contains one-twentiethmole of water. The sulbactam sodium compound has main diffraction peaks at the positions with the corresponding main X-ray characteristic diffraction peak 2 theta angle of 14.23+/-0.2 degrees, 17.76+/-0.2 degrees, 19.22+/-0.2 degrees, 23.09+/-0.2 degrees, 24.60+/-0.2 degrees and 27.86+/-0.2 degrees. The sulbactam sodium compound prepared by means of a method has high stability and meets the requirements for being used a raw material of a preparation.

Extends the batanbatan acid synthesis method (by machine translation)

The present invention relates to the field of drug synthesis, directed to the problem of low yield synthesis mode, provides a method of synthesizing extends the batanbatan acid, comprises the following steps: S1, diazotization and bromination reaction: in the 6 - amino penicillanic acid bromine is added in, the dilute sulfuric acid solution and sodium nitrite solid, dilute sulfuric acid concentration of the solution is 20% - 25%, to obtain the 1st intermediate; S2, oxidation reaction: to the 1st intermediate dropping potassium permanganate and dilute sulfuric acid solution, the concentration of the dilute sulfuric acid solution is 20% - 25%; S3, hydrogenation reaction: to the 2nd intermediate [...] and in dilute sulfuric acid solution, to obtain the extends the batanbatan acid. By using the 20% - 25% of the dilute sulfuric acid solution react, help to improve the diazo and bromination reaction and oxidation reaction of the active, so that the reactant more completely, thus help to improve the diazo and bromination reaction and oxidation of the yield of the reaction, and then make the overall yield of the reaction. (by machine translation)

Method for preparing sulbactam acid

The invention relates to the field of pharmaceutical synthesis and provides a method for preparing sulbactam acid. The method is used for solving the problem of the traditional synthesis methods thatthe yield is low. The method comprises the following steps: S1. diazotation and bromination reaction: adding bromine, a dilute sulfuric acid solution and sodium nitrite solids into 6-aminopenicillanicacid, so as to obtain a first intermediate, wherein the dilute sulfuric acid solution adopts depleted deuterium water as a solvent; S2. oxidation reaction: dropwise adding potassium permanganate anda dilute sulfuric acid solution into the first intermediate, so as to obtain a second intermediate; and S3. hydrogenation reaction: add strontium powder and a dilute sulfuric acid solution into the second intermediate, thereby obtaining a product, i.e., the sulbactam acid, wherein the dilute sulfuric acid solution adopts depleted deuterium water as a solvent. Through preparing the dilute sulfuricacid solution by adopting the depleted deuterium water as the solvent and adopting the strontium powder as a catalyst, the improvement on reaction activity of dilute sulfuric acid is facilitated, theconversion ratio of reaction is increased, and thus, the increase of reaction yield is facilitated, so that the yield of reaction can be higher than 90%.

New indications of troxofine ceftriaxone sodium pharmaceutical preparation for treatment of infection of patients with immunodeficiency

The invention belongs to the technical field of drug preparation, and discloses new indications of a troxofine ceftriaxone sodium pharmaceutical preparation for treatment of infection of patients withimmunodeficiency. By improving a raw material synthesis process, ceftriaxone sodium with the high effective constituent content and the low impurity content is provided so as to solve the problems ofpoor stability and reducing of the antibacterial effect of a ceftriaxone sodium preparation due to impurities. The ceftriaxone sodium provided by the specific production process is very low in impurity content and significant in efficacy, the quality of a preparation product is improved advantageously, safety and effectiveness of the preparation product are ensured, and the preparation product has uses in the aspects of preparing drugs for treating infection of the patients with immunodeficiency.

A [...] synthetic method

The invention discloses a synthetic method of salbactam acid. The synthetic method comprises the following steps: carrying out diazotized bromination reaction on 6-aminopenicillanic acid to form bromopenicillanic acid; and then, carrying out oxidation reaction and reduction reaction to obtain salbactam acid, wherein in the diazotized bromination reaction, 6-aminopenicillanic acid is continuously added in form of an acidic solution, the acidic solution of 6-aminopenicillanic acid is 5-8% sulfuric acid aqueous solution, 13-15% hydrobromic acid aqueous solution or 5-8% hydrochloric acid aqueous solution. 6-aminopenicillanic acid is dropwise added in form of the acidic solution, so that dust pollution is avoided and the work environment of field personnel is improved. Meanwhile, 6-aminopenicillanic acid exists in form of stable salt, decomposition reaction is avoided, and the reaction quality is improved. The three-step yield of the method is over 70%, the HPCL purity is over 99.7%, the individual impurity content is less than 0.1% and the total impurity content is less than 0.5%.

New synthesis method for sulbactam acid

The invention discloses a new synthesis method for sulbactam acid. The new synthesis method comprises the following steps: performing reaction between 6-amino-penicillanic acid and sodium nitrite and bromine in water-insoluble organic solvent under an acidic condition to obtain a reaction product: bis-bromo-penicillanic acid, and then, performing oxidation reaction and hydrogenation to obtain sulbactam. According to the new synthesis method disclosed by the invention, by adopting the water-insoluble solvent, emission of organic matter in water is reduced; by adopting a mode of step-by-step-oxidation, not only is the usage level of potassium permanganate reduced but also the phenomenon that a large amount of ethyl acetate is used originally is avoided; filtering separation is performed on manganese dioxide by the solvent, and thus, not only is emission of the three wastes reduced but also the solvent can also be utilized as a by-product; emission of organic matter and waste salt in an original process is greatly reduced, and side reaction and raw material cost are also greatly reduced.

Synthesis and crystal of methyl 6,6-dihydropenicillanate S,S-dioxide

6,6-dihydropenicillanate S,S-dioxide 5 was prepared and determined by X-ray crystallography. Single-crystal X-ray diffraction analysis reveals that the molecular structure of compound 5b is enantiomerically pure. The crystal belongs to orthorhombic, space group P212121, with unit cell parameters a = 6.5366 A, b = 10.7649(9) A, c = 15.5879(13) A, V = 1096.86(16) A3, Dx = 1.491 g cm 3, Z = 4, T = 296(2)K, F(000) = 520, R 1 = 0.0401, and wR 2 = 0.1200. Absolute structure parameter is 0.02(10).