Sulfur (VI) fluoride compounds and methods for the preparation thereof

Patent metadata

Field	Value
Publication number	US-11141385-B2
Application number	US-202017012783-A
Country	US
Kind code	B2
Filing date	Sep 4, 2020
Priority date	Jun 6, 2014
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

Abstract

This application describes a compound represented by Formula (I):wherein: Y is a biologically active organic core group comprising one or more of an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which Z is covalently bonded; n is 1, 2, 3, 4 or 5; m is 1 or 2; Z is O, NR, or N; X1 is a covalent bond or —CH2CH2—, X2 is O or NR; and R comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group. Methods of preparing the compounds, methods of using the compounds, and pharmaceutical compositions comprising the compounds are described as well.

First claim

We claim:

1. A compound of Formula (I):

wherein:
Y is an antibiotic core group comprising one or more unsubstituted or substituted moiety selected from the group consisting of an aryl group, a heteroaryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which each Z independently is covalently bonded;
n is 1, 2, 3, 4 or 5;
each Z independently is NR, or N;
when Z is NR, m is 1, X 1 is a covalent bond or CH 2 CH 2 , and the Z is covalently bonded to a nonaromatic hydrocarbyl, a nonaromatic heterocyclic, an aryl, or heteroaryl moiety of Y;
when Z is N, either (a) m is 2, X 1 is CH 2 CH 2 and the Z is covalently bonded to a nonaromatic hydrocarbyl, a nonaromatic heterocyclic, an aryl, or a heteroaryl moiety of Y; or (b) m is 1, X 1 is a covalent bond or CH 2 CH 2 , and the Z is a nitrogen in an aromatic or non-aromatic heterocyclic ring portion of core group Y;
each X 2 independently is O or NR; and
each R independently comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group.

2. The compound of claim 1 , wherein the antibiotic is selected from the group consisting of a cephalosporin, ciprofloxacin, sulfacetamide, amoxicillin, sulfanilamide, sulfamethoxazole, norfloxacin, gatifloxacin, gemifloxacin, trimethoprim, pyrimethamine, cefadroxil, isoniazid, streptomycin, moxifloxacin, and aminosalicylic acid.

3. The compound of claim 1 , wherein the antibiotic is selected from the group consisting of a cephalosporin or ciprofloxacin.

4. The compound of claim 1 having the formula:

Assignees

• Scripps Research Inst

Inventors

• Dong Jiajia
• Sharpless K Barry
• Kelly Jeffery W
• Baranczak Aleksandra
• Chen Wentao

Classifications

• A61K31/05 Primary

  Phenols {(cannabinoids A61K31/658)} · CPC title

• A61K31/197

  the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid (carnitine A61K31/205) · CPC title

• A61K31/14

  Quaternary ammonium compounds, e.g. edrophonium, choline (betaines A61K31/205) · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• A61K31/198

  Alpha-amino acids, e.g. alanine or edetic acid [EDTA] (betaine A61K31/205; proline A61K31/401; tryptophan A61K31/405; histidine A61K31/4172; peptides not degraded to individual amino acids A61K38/00) · CPC title