# US 7,745,656 B2 · Stable no-delivering compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,745,656 B2 - Document ID: US7745656B2 - Status: Granted - Kind: B2 - Application number: 11/376,756 - Filed: 2006-03-14 - Published: 2006-09-28 - Granted: 2010-06-29 - Earliest claimed: 1998-06-23 - Assignees: Duke University - Inventors: Eric J. Toone; Jonathan S. Stamler - Web page: https://patentgrep.com/patent/US7745656B2 ## CPC - A61L 2/23: Solid materials, e.g. granules, powders, blocks or tablets - A61L 2/20: Gaseous substances, e.g. vapours - A61L 29/16: Biologically active materials, e.g. therapeutic substances {(A61L29/048 takes precedence)} - A61P 31/04: Antibacterial agents - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - C07C 381/00: Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00 - A61L 2300/114: Nitric oxide, i.e. NO - A61L 2300/216: with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups - A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract Disclosed are novel NO-releasing compounds which comprise a stabilized S-nitrosyl group and a free alcohol or a free thiol group. Also disclosed is a method of preparing the NO-releasing compounds. The method comprises reacting a polythiol or a thioalcohol with a nitrosylating agent. Also disclosed are medical devices coated with the disclosed compounds, methods of delivering NO to treatments sites in a subject by utilizing the medical devices and methods of sterilizing surfaces. ## Claims ### Claim 1 A compound containing at least one S-nitrosyl group and at least one free thiol group, wherein the free thiol group stabilizes the S-nitrosyl group, and optionally one or more functional groups selected from the group consisting of alcohols, amides, thioamides, aldehydes, ketones, halogens, double bonds, triple bonds and aryl groups, wherein the compound has a molecular weight greater than about 375 atomic mass units, wherein at least one free thiol is located within three covalent bonds of at least one S-nitrosyl group, with the proviso that the compound is not an S-nitrosylated derivative of a polypeptide, a polythiolated polysaccharide, or a polymer with pendant thiol groups and is not an S-nitrosylated derivative of a compound represented by one of the following structural formulas: wherein each Ra is —H or methyl and is independently chosen. ### Claim 2 (depends on 1) The compound of claim 1, wherein the compound is prepared by reacting a polythiol with a nitrosylating agent. ### Claim 3 (depends on 2) The compound of claim 2, wherein 0.5 to 0.7 equivalents of nitrosylating agent are used per free thiol in the polythiol. ### Claim 4 (depends on 1) The compound of claim 1, wherein the compound is prepared by reacting a thioalcohol with a nitrosylating agent. ### Claim 5 (depends on 1) The compound of claim 1, wherein the compound has a molecular weight less than 1000 atomic mass units. ### Claim 6 (depends on 4) The compound of claim 4, wherein the compound has a molecular weight less than about 1000 atomic mass units and wherein the alcohol and thiol of the thioalcohol are both primary. ### Claim 7 (depends on 2) The compound of claim 2, which has a molecular weight less than 1000 atomic mass units and which has two primary thiols. ### Claim 8 (depends on 2) The compound of claim 2, wherein the nitrosylating agent is S-nitroso-N-acetyl-D,L-penicillamine. ### Claim 9 A compound containing at least one S-nitrosyl group and at least one free alcohol group, wherein the free alcohol group stabilizes the S-nitrosyl group, and optionally one or more functional groups selected from the group consisting of thiols, amides, thioamides, aldehydes, ketones, halogens, double bonds, triple bonds and aryl groups, wherein the compound has a molecular weight greater than about 500 atomic mass units, and wherein at least one free alcohol group is located within three covalent bonds of at least one S-nitrosyl group, with the proviso that the compound is not an S-nitrosylated derivative of a polypeptide, a polythiolated polysaceharide, or a polymer with pendant thiol groups and is not an S-nitrosylated derivative of a compound represented by one of the following structural formulas: wherein each Ra is —H or methyl and is independently chosen. ### Claim 10 (depends on 9) The compound of claim 9, wherein the compound is prepared by reacting a thioalcohol with a nitrosylating agent. ### Claim 11 (depends on 10) The compound of claim 10, wherein 0.5 to 0.7 equivalents of nitrosylating agent are used per free thiol and per free alcohol in the thioalcohol. ### Claim 12 (depends on 9) The compound of claim 9, wherein the compound has a molecular weight less than 1000 atomic mass units. ### Claim 13 (depends on 11) The compound of claim 11, wherein the compound has a molecular weight less than about 1000 atomic mass units and wherein the alcohol and thiol are both primary. ### Claim 14 (depends on 9) The compound of claim 9, wherein the nitrosylating agent is S-nitroso-N-acetyl-D,L-penicillamine. ### Claim 15 (depends on 1) The compound of claim 1, wherein the compound has a molecular weight greater than about 500 atomic mass units.