Use of squalamine or analogue as a disinfecting agent

Patent metadata

Field	Value
Publication number	US-9700051-B2
Application number	US-201314371292-A
Country	US
Kind code	B2
Filing date	Jan 4, 2013
Priority date	Jan 12, 2012
Publication date	Jul 11, 2017
Grant date	Jul 11, 2017

Abstract

The present invention relates to the use of a compound chosen from squalamine and a squalamine-analog aminosteroid compound as agent for disinfecting an inert material object, in particular for the pre-disinfection of medical, dental, diagnostic or surgical equipment.
The present invention also provides an aqueous or water-soluble disinfecting composition beneficial for a use according to the invention, characterized in that as disinfecting active compound it comprises a said antibacterial and antifungal compound selected from squalamine and a said squalamine-analog aminosteroid compound and suitable excipients for a water-soluble or aqueous formulation.

First claim

The invention claimed is:

1. A method of disinfecting an inert material object comprising:
providing an agent for disinfection of the inert material object, said agent being a water-soluble salt of squalamine, or a water-soluble salt of an antibacterial and antifungal squalamine-analogue aminosteroid;
formulating said compound as an aqueous solution, or as a solid, water-soluble composition;
contacting the inert material object with an aqueous solution of the formulated compound; and
wherein said compound is capable of killing in vitro:
a) at least 99.999% of pathogenic bacteria S. aureus and P. aeruginosa in a suspension containing a concentration of 10 8 cfu/ml of said bacterium at 20° C.; and
b) at least 99.990% of pathogenic yeasts C. albicans and A. niger in a suspension containing a concentration of at least 10 7 cfu/ml of said yeast at 20° C.

2. The method according to claim 1 , wherein said inert material object is equipment for food, medical, dental, pharmaceutical, diagnostic, or surgical use.

3. The method according to claim 1 , wherein said inert material object is placed in contact with an aqueous composition of squalamine or said aminosteroid analogue compound.

4. The method according to claim 1 , wherein said compound is used in the form of an aqueous solution at a concentration of 3 mM to 8 mM.

5. The method according to claim 3 , wherein a solid water-soluble composition in powder or tablet form containing the compound at a concentration of at least 2.5% by weight is diluted in an aqueous solution, said composition being soluble in an aqueous solution.

6. The method according to claim 1 , wherein said compound is squalamine of formula Ia:

7. The method according to claim 1 , wherein said squalamine-analogue aminosteroid compound has a formula comprising a backbone of formula (I) below, on which at least one polyamine-NHR chain is grafted, R being an optionally substituted hydrocarbon chain comprising at least one-NH 2 group:

where:
either all the bonds lined with a dotted line between the carbons at positions 7-8, 5-6, 4-5, and 3-4 represent a single bond, the backbone being that of a 10, 13, 17 trimethyl cholestane,
or one of the bonds lined with a dotted line between the carbons at positions 7-8, 5-6, 4-5, and 3-4 represents a double bond and the other bonds lined with a dotted line are single bonds, the backbone being that of a 10, 13, 17 trimethyl cholestene.

8. The method according to claim 7 , wherein said compound has a formula comprising the backbone of formula (I) comprising:
a) at least 1-NHR chain on one of the carbons at positions 3, 7, and 20, and R is —[(CH 2 )n-(NR 1 ) k —(CH 2 ) m ] p —NH 2
where:
n and m are integers, the same or different, from 1 to 7;
k=0 or 1;
p is an integer from 1 to 4; and
R 1 is selected from H, a C1 to C8 alkyl, an optionally substituted phenyl and -COOalk group, alk being a C1 to C3 alkyl; and

b) the other carbons of said backbone comprise a radical R 0 the same or different selected from H, OH, NH 2 , SH and R 1 .

9. The method according to claim 8 wherein:
a) in the formula of R:
if k=0, then p=1, or if k=1, then p=2; and
if said compound comprises a single-NHR chain, this is grafted at position 3 or 7; and

b) the radical R 0 , on the other carbons of said backbone, is H or OH, but with only one R 0 representing OH.

10. The method according to claim 8 , wherein said aminosteroid compound has one of the following formulas IIa, IIb, IIc, or IId, wherein R represents —[(CH 2 ) n —(NR 1 ) k —(CH 2 ) m ] p —NH 2 , where

11. The method according to claim 10 , wherein R is selected from —(CH 2 )n1-NH 2 , where n1=2 to 14, and —(CH 2 )3-NH—(CH 2 )3-NH—(CH 2 )3-NH 2 .

12. The method according to claim 10 , wherein said compound has a formula II-1:

13. A method according to claim 1 , wherein said water soluble composition comprises an excipient for formulation in the form of a water-soluble solid tablet or water-soluble powder, said excipient being selected from the group consisting of microcrystalline cellulose, lactose, starch, scroscarmellose sodium, colloidal silica, and magnesium stearate.

14. The method according to claim 1 , wherein said water-soluble salt is selected from the group consisting of chlorhydrate, bromhydrate, triflate, phosphate, lactate, and succinate.

15. The method according to claim 1 , wherein the inert material object is contacted with an aqueous solution having a concentration of at least 2 g/L of the compound.

16. A method of disinfecting an inert material object comprising:
providing an agent for disinfection of the inert material object, said agent being a water-soluble salt of squalamine, or a water soluble salt of an antibacterial and antifungal squalamine-analogue aminosteroid;
formulating said compound as an aqueous solution, or as a solid, water-soluble composition;
contacting the inert material object with an aqueous solution of the formulated compound; and
wherein said compound has a formula II-1:

Assignees

• Brunel Jean-Michel
• Raoult Didier
• Rolain Jean-Marc
• Assist Publique—Hopitaux De Marseille
• Univ Aix Marseille
• Fond Mediterranee Infection

Inventors

• Brunel Jean-Michel
• Raoult Didier
• Rolain Jean-Marc

Classifications

• A01N63/10

  Animals; Substances produced thereby or obtained therefrom · CPC title

• A01N25/02

  containing liquids as carriers, diluents or solvents · CPC title

• A01N45/00 Primary

  Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring (halogenated hydrocarbons A01N29/08; condensed with heterocyclic rings A01N43/00) · CPC title

• A01N49/00 Primary

  Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group [IMAGE cpc-sch-A01N-0948.gif], wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group [IMAGE cpc-sch-A01N-0949.gif], wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof (containing hydrocarbons A01N27/00) · CPC title

• A01N2300/00

  Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48 · CPC title