53784-84-2

Usage

Uses

Used in Pharmaceutical Applications:
OCTAKIS-6-BROMO-6-DEOXY-GAMMA-CYCLODEXTRIN is used as a nanomolecular encapsulation agent for drug delivery. Its ability to form inclusion complexes with guest molecules allows for improved solubility, stability, and bioavailability of drugs, enhancing their therapeutic effects.
Used in the Synthesis of Unilamellar Vesicles:
In the field of supramolecular chemistry, OCTAKIS-6-BROMO-6-DEOXY-GAMMA-CYCLODEXTRIN is used in the synthesis of unilamellar vesicles. These vesicles have potential applications in drug delivery systems, as they can encapsulate and protect sensitive drug molecules, facilitating their transport and release in a controlled manner.
Used in Neurobiology Research:
OCTAKIS-6-BROMO-6-DEOXY-GAMMA-CYCLODEXTRIN is also utilized in neurobiology research, where it has been shown to inhibit neurite growth in vitro. This property makes it a valuable tool for studying the mechanisms underlying neuronal development and the potential development of therapeutic strategies for neurological disorders.

Upstream product

• 17465-86-0 cyclomaltooctaose 

Downstream Products

• 343306-89-8 6-per-deoxy-6-per-(N-methylamidomethyl)thio-γ-cyclodextrin 
• 343329-56-6 C₈₈H₁₄₄O₄₈S₈ 
• 871544-29-5 octakis[6-(2-aminoethylamino)-6-deoxy]-γCD 
• 1040373-29-2 octakis[6-(2-aminopropylamino)-6-deoxy]-γCD 
• 180839-61-6 6-per-deoxy-6-per-thio-γ-cyclodextrin 

Relevant academic research and scientific papers

Mechanistic Understanding of a Robust and Scalable Synthesis of Per(6-deoxy-6-halo)cyclodextrins, Versatile Intermediates for Cyclodextrin Modification

Cyclodextrin (CD) perfunctionalization reactions are challenging to study because they proceed through a number of regioisomeric intermediates, thus warranting creative approaches to understanding the reaction mechanism. Particularly useful perfunctionalization targets are per(6-deoxy-6-halo)cyclodextrins. Their standard synthesis entails selective SN2 halogenation at their primary alcohols using a Vilsmeier reagent, but this requires a strongly basic quench to unmask the Vilsmeier-capped secondary alcohols. Herein we present an alternative and simple acidic hydrolytic quench that utilizes existing HX in the end-of-reaction solution and requires only the addition of water. We performed a detailed mechanistic investigation of the new quench, and a central feature was the use of proton sponge to develop an 1H NMR titration method for HX in organic solvent. This method was used to both quantify and remove HX in the prequenched reaction solution. The HX-free prequenched solution enabled us to (1) identify sensitive intermediates during the quench, (2) quantify all of the reaction byproducts, and (3) determine that HX is critical for hydrolysis. We then studied the halogenation reaction, wherein the new acidic quench facilitated high-throughput experimentation, using mass spectrometry as well as Design of Experiments with automated reaction profiling. Through this, we were able to establish robustness and understand the complex effects of Vilsmeier equivalents and temperature on the reaction outcome.

AN IMPROVED PROCESS FOR THE PREPARATION OF SUGAMMADEX SODIUM AND ITS NOVEL POLYMORPHIC FORM

The present invention provides an improved process for the preparation of Sugammadex sodium of formula (I) having more than 98.5% purity along with less than 1.0% monohydroxy Sugammadex sodium and less than 0.15% any other known or unknown impurities by HPLC.

PROCESS FOR MAKING SUGAMMADEX

The invention deals with a novel process for making intermediates of the pharmaceutically useful product Sugammadex of formula (1).

POLYMORPHS OF SUGAMMADEX AND PROCESS FOR PREPARATION OF SUGAMMADEX

The present invention provides a crystalline form of Suagmmadex sodium, characterized by an X-ray powder diffraction pattern. The present invention further provides crystalline forms of Suagmmadex sodium for use in the manufacture of a pharmaceutical composition or a medicament. The present invention further provides a pharmaceutical composition comprising the crystalline form of Sugammadex sodium of the present invention and at least one pharmaceutical acceptable excipient.

PROCESSES FOR THE PREPARATION OF SUGAMMADEX

The present invention provides processes for the preparation of sugammadex: (I) In one aspect, there is provided a process for the preparation of sugammadex from 8-per-deoxy-8-bromo-γ-cyclodextrin and 3-mercaptopropionic acid. In another aspect, there is provided an alternative process for the preparation of sugammadex from 8-per-deoxy-8-bromo-γ-cyclodextrin and disodium 3-mercaptopropionate. In another aspect, there is provided a process for the preparation of 8-per-deoxy-8-bromo-γ-cyclodextrin, which may be used in the production of sugammadex. In one such aspect, there is provided a process for the preparation of 8-per-deoxy-8-bromo-γ-cyclodextrin from γ-cyclodextrin and a brominating agent. In another such aspect, there is provided a process for the preparation of 8-per-deoxy-8-bromo-γ-cyclodextrin comprising, inter alia, reacting γ-cyclodextrin with an electrophilic brominating agent, a deoxygenating agent, and an acid in the presence of an organic solvent.

METHOD FOR PREPARATION OF SUGAMMADEX SODIUM

The present invention provides a method for improved preparation of Sugammadex sodium.

PROCESS FOR MAKING SUGAMMADEX

The invention relates to a novel process for making the pharmaceutical product Sugammadex. OVERVIEW OF THE PRIOR ART Sugammadex, i.e. 5-Cyclooctakis-(1→4)- [6-S-(2-carboxyethyl)-6-thio-alfa-D-glucopyranosyl] of formula (I), is a modified γ-cyclodextrin. Sugammadex is the first selective relaxant binding agent for reversal of neuromuscular blockade by the agent rocuronium or vecuronium in general anesthesia. It was approved in 2008

Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins

A number of per-6-substituted cyclodextrin derivative syntheses have been effectively carried out in a planetary ball mill under solvent-free conditions. The preparation of Bridion and important per-6-amino/thiocyclodextrin intermediates without polar aprotic solvents, a source of byproducts and persistent impurities, could be performed. Isolation and purification processes could also be simplified. Considerably lower alkylthiol/halide ratio were necessary to reach the complete reaction in comparison with thiourea or azide reactions. While the presented mechanochemical syntheses were carried out on the millimolar scale, they are easily scalable.

A convenient procedure for the formation of per(6-deoxy-6-halo) cyclodextrins using the combination of tetraethylammonium halide with [Et 2NSF2]BF4

A convenient and efficient procedure for the regioselective halogenation of the primary alcohols of cyclodextrins using the reagent combination of tetraethylammonium halide with [Et2NSF2]BF4 is described. Georg Thieme Verlag Stuttgart New York.

An improved and alternative method for the preparation of per(6-bromo-6-deoxy)cyclodextrins

A practical and efficient approach to the regioselective synthesis of per(6-bromo-6-deoxy)cyclodextrins is described. The method utilizes the easily accessible (chloro(phenylthio)methylene)dimethylammonium chloride (CPMA), circumventing disadvantages of earlier protocols. Georg Thieme Verlag Stuttgart. New York.