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

Patent metadata

Field	Value
Publication number	US-10117840-B2
Application number	US-201515316742-A
Country	US
Kind code	B2
Filing date	Jun 5, 2015
Priority date	Jun 6, 2014
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

This application describes a compound represented by Formula (I): (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; X 1 is a covalent bond or —CH 2 CH 2 —, X 2 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. An amino protected O-fluorosulfonyl-L-tyrosine of formula:

wherein “Fmoc” represents a 9-fluorenylmethyloxycarbonyl protecting group.

2. A polypeptide comprising an O-fluorosulfonyl-L-tyrosine residue.

3. The polypeptide of claim 2 , wherein the polypeptide is selected from the group consisting of oxytocin, indolicin, thymopentin, and arginine vassopressin, in which the tyrosine residue thereof is replaced by an O-fluorosulfonyl-L-tyrosine residue.

4. A method of preparing a sulfated polypeptide comprising contacting the polypeptide of claim 2 with cesium carbonate and a solution of ammonia in methanol to selectively hydrolyze the fluoro group of the fluorosulfonyl-L-tyrosine residue and from a sulfated tyrosine residue therefrom.

Assignees

• Scripps Research Inst

Inventors

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

Classifications

• C07D279/08

  condensed with carbocyclic rings or ring systems · CPC title

• A61P5/24

  of the sex hormones · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P5/38

  of the suprarenal hormones · CPC title

• A61P31/00

  Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics · CPC title