Oxathiazin-like compounds, processes for making new oxathiazin-like compounds, compounds useful for making oxathiazin-like compounds, and their uses are disclosed. Processes of treating patients suffering from cancers, bacterial infections, fungal infections and/or viral infections by administering oxathiazin-like compounds are also disclosed. These compounds were found to have significantly longer half-life compared to taurolidine and taurultam.

The present invention generally relates to a process for the preparation of a product, the product being 6-methyl-3,4-dihydro1,2,3-oxathiazin-4-one 2,2-dioxide or a derivative thereof. The present invention also relates to the use of such a process for making diammonium sulphate. The present invention relates to a process for the preparation of a product, the product being 6-methyl-3,4-dihydro1,2,3-oxathiazin-4-one 2,2-dioxide or a derivative thereof, the process comprising the following steps: a. Contacting SO 3 and acetoacetamide-N-sulphonic acid or a derivative thereof in the presence of an amine, thereby obtaining a first stream comprising the amine and sulphuric acid; b. Providing a second stream comprising ammonia; c. Providing a circuit; d. Introducing the second stream into the circuit at point A and the first stream into the circuit at point B to obtain a cycle stream cycling in the circuit; e. Removing a portion of the cycle stream at a point C to obtain a third stream; wherein the circulation ratio is in the range from 3 to 30, the circulation ratio being the value of the mass flow rate of the cycle stream immediately preceding point A F c divided by the value of the mass flow rate of the first stream into the circuit at point B F according to the following formula: circulation ratio=F c/F 2 FIG. 130

The present invention generally relates to a process for the preparation of a product, the product being 6-methyl-3,4-dihydro1,2,3-oxathiazin-4-one 2,2-dioxide or a derivative thereof. The present invention also relates to the use of such a process for making diammonium sulphate. The present invention relates to a process for the preparation of a product, the product being 6-methyl-3,4-dihydro1,2,3-oxathiazin-4-one 2,2-dioxide or a derivative thereof, the process comprising the following steps: a. Contacting SO 3 and acetoacetamide-N-sulphonic acid or a derivative thereof in the presence of an amine, thereby obtaining a first stream comprising the amine and sulphuric acid; b. Providing a second stream comprising ammonia; c. Providing a circuit; d. Introducing the second stream into the circuit at point A and the first stream into the circuit at point B to obtain a cycle stream cycling in the circuit; e. Removing a portion of the cycle stream at a point C to obtain a third stream; wherein the circulation ratio is in the range from 3 to 30, the circulation ratio being the value of the mass flow rate of the cycle stream immediately preceding point A F c divided by the value of the mass flow rate of the first stream into the circuit at point B F according to the following formula: circulation ratio=F c/F 2 FIG. 130

Methods for producing compounds useful in reactions to produce oxathiazin-like compounds are disclosed including a process of adding sodium 2-bromoethanesulfonate to a solution of benzyl alcohol and sodium benzyloxide to for mixture, boiling the mixture to reflux four times, concentrating under vacuum until dry, boiling with ethyl alcohol, filtering the ethyl alcohol, and concentrating to dryness to obtain solid sodium 2-benzyletherethanesulfonate.

Methods for producing compounds useful in reactions to produce oxathiazin-like compounds are disclosed including a process of adding sodium 2-bromoethanesulfonate to a solution of benzyl alcohol and sodium benzyloxide to for mixture, boiling the mixture to reflux four times, concentrating under vacuum until dry, boiling with ethyl alcohol, filtering the ethyl alcohol, and concentrating to dryness to obtain solid sodium 2-benzyletherethanesulfonate.

Improved processes for producing high purity acesulfame potassium. In one embodiment, the process comprises the steps of contacting a solvent, e.g., dichloromethane, and a cyclizing agent, e.g., sulfur trioxide, to form a cyclizing agent composition and reacting an acetoacetamide salt with the cyclizing agent in the composition to form a cyclic sulfur trioxide adduct. The contact time is less than 60 minutes. The process also comprises forming from the cyclic sulfur trioxide adduct composition a finished acesulfame potassium composition comprising non-chlorinated, e.g., non-chlorinated, acesulfame potassium and less than 35 wppm 5-halo acesulfame potassium, preferably less than 5 wppm.

Improved processes for producing high purity acesulfame potassium. In one embodiment, the process comprises the steps of contacting a solvent, e.g., dichloromethane, and a cyclizing agent, e.g., sulfur trioxide, to form a cyclizing agent composition and reacting an acetoacetamide salt with the cyclizing agent in the composition to form a cyclic sulfur trioxide adduct. The contact time is less than 60 minutes. The process also comprises forming from the cyclic sulfur trioxide adduct composition a finished acesulfame potassium composition comprising non-chlorinated, e.g., non-chlorinated, acesulfame potassium and less than 35 wppm 5-halo acesulfame potassium, preferably less than 5 wppm.

In one embodiment, the invention relates to processes for producing acesulfame potassium. In one embodiment, the process comprises the step of reacting a first reaction mixture to form an amidosulfamic acid salt such as a trialkyl ammonium amidosulfamic acid salt. The first reaction mixture comprises sulfamic acid, an amine, and smaller amounts, if any, acetic acid, e.g., less than 1 wt % (10000 wppm). In terms of ranges, the first reaction mixture may comprise from 1 wppm to 1 wt % acetic acid. The process further comprises the step of reacting the amidosulfamic acid salt with diketene to form an acetoacetamide salt. In preferred embodiments, the amidosulfamic acid salt formation reaction is conducted at pH levels from 5.5 to 7.0. The process further comprises the step of deriving the acesulfame-K from the acetoacetamide salt.

In one embodiment, the invention relates to processes for producing acesulfame potassium. In one embodiment, the process comprises the step of reacting a first reaction mixture to form an amidosulfamic acid salt such as a trialkyl ammonium amidosulfamic acid salt. The first reaction mixture comprises sulfamic acid, an amine, and smaller amounts, if any, acetic acid, e.g., less than 1 wt % (10000 wppm). In terms of ranges, the first reaction mixture may comprise from 1 wppm to 1 wt % acetic acid. The process further comprises the step of reacting the amidosulfamic acid salt with diketene to form an acetoacetamide salt. In preferred embodiments, the amidosulfamic acid salt formation reaction is conducted at pH levels from 5.5 to 7.0. The process further comprises the step of deriving the acesulfame-K from the acetoacetamide salt.

Compositions and processes for producing high purity acesulfame potassium are described. One process comprises the steps of forming a cyclic sulfur trioxide adduct; hydrolyzing the cyclic sulfur trioxide adduct to form an acesulfame-H composition comprising acesulfame-H; neutralizing the acesulfame-H in the acesulfame-H composition to form a crude acesulfame potassium composition comprising acesulfame potassium and less than 2800 wppm acetoacetamide-N-sulfonic acid, wherein the neutralizing step is conducted or maintained at a pH at or below 11.0; and treating the crude acesulfame potassium composition to form the finished acesulfame potassium composition comprising acesulfame potassium and less than 37 wppm acetoacetamide-N-sulfonic acid.