NO containing compositions

Patent metadata

Field	Value
Publication number	US-10449215-B2
Application number	US-201615547670-A
Country	US
Kind code	B2
Filing date	Jan 28, 2016
Priority date	Feb 3, 2015
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

Disclosed are metal organic framework materials (MOFs), comprising an extra-framework NO releasing compound within the internal pores and/or channels of the MOF, the NO-releasing compounds and their preparation and uses. The MOFs and NO-releasing compounds are capable of releasing NO on application of an external stimulus and may provide materials with multiple modes of antibacterial and/or drug action.

First claim

The invention claimed is:

1. A biguanide containing compound comprising one or more NO molecules bound thereto, wherein the biguanide is obtained by reacting a precursor compound having the general structure I:

with NO gas or a nitrosylating agent in order to generate a biguanide containing compound comprising one or more NO molecules bound thereto; wherein
R 1 -R 5 independently comprise (a) substituted or unsubstituted C 1 -C 10 alkyl-, (b) substituted or unsubstituted aryl-, (c) H, with the proviso that R 2 is not H when R 1 is H, and R 4 is not H when R 3 is H or (d) a bond or linking group to a further structure (I) as defined above, or to a polymer or other macromolecule;
R 6 and R 7 independently are H, C 1 -C 10 alkyl- or aryl- or together or independently represent a coordinated metal ion;
R 8 -R 12 are each optional, but when present result in the N atom to which they are bound becoming positively charged and independently comprise H, C 1 -C 10 alkyl- or aryl-; and

substituents independently comprise C 1 -C 10 alkyl-, phenyl- or halogen.

2. The biguanide containing compound of claim 1 , wherein the coordinated metal ion is selected from the group consisting of silver, copper, nickel, zinc, magnesium and calcium.

3. The biguanide containing compound of claim 1 wherein R 5 -R 7 and R 8 -R 12 , when present, are H.

4. The biguanide containing compound of claim 1 , which is N,N′-bi-substituted, N,N,N′-tri-substituted, N,N′,N′-tri-substituted or N,N,N′,N′-tetra-substituted molecule wherein each substituent is a non-H substituent.

5. A porous framework material comprising an extra-framework NO complexed biguanide containing compound of claim 1 within the internal pores and/or channels of the porous framework material.

6. The porous framework material of claim 5 which is a metal organic framework material (MOF).

7. A porous framework material according to claim 5 that releases NO from the extra-framework biguanide containing compound and/or the released biguanide compound, wherein the rate of release of NO optionally is altered by an external stimulus.

8. The porous framework material of claim 5 wherein the external stimulus is a change in temperature or pressure, irradiation with light, or contact with another species.

9. A method of preparing a porous framework material of claim 5 ;
the method comprising:
forming a NO complexed compound from a suitable precursor compound; and
contacting a porous framework material with the NO complexed compound so as to adsorb the NO complexed compound into the pores and/or channels of the porous framework material;

or the method comprising:
forming a porous framework material which comprises a precursor compound capable of reacting to form a NO complexed compound in the pores and/or channels of the porous framework material; and
forming an extra-framework NO complexed compound in situ by contacting the porous framework material with NO.

10. A method of releasing NO, comprising providing a porous framework material of claim 5 having an extra-framework NO complexed compound within the internal pores and/or channels of the porous framework material, contacting said porous framework material with a medium into which the NO is to be released, and releasing NO into the medium, and optionally further comprising applying an external stimulus to the porous framework material, wherein the external stimulus comprises an increase in temperature, a change in pH, irradiation with light, a change in pressure, or a combination thereof and/or wherein the external stimulus comprises contacting the porous framework material with another species.

11. The method of claim 10 wherein the another species is water.

12. A pharmaceutical, neutraceutical or cosmetic preparation comprising a porous framework material of claim 5 , together with a pharmaceutical, neutraceutical or cosmetic carrier therefor.

Assignees

• Univ Court Univ St Andrews

Inventors

• Duncan Morven
• Warrender Stewart
• Morris Russell Edward
• Cattaneo Damiano

Classifications

• A61P9/12

  Antihypertensives · CPC title

• A61P7/10

  Antioedematous agents; Diuretics · CPC title

• A61P31/04

  Antibacterial agents · CPC title

• A61K31/496

  Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin · CPC title

• A61K33/00 Primary

  Medicinal preparations containing inorganic active ingredients · CPC title