INTERMITTENT CATHETERS

Abstract

The invention relates to intermittent catheters comprising a calixarene bonded to a surface thereof, in particular to provide a bacteria-repellent and/or lubricous coating on the outer surface of an intermittent catheter. The calixarene moiety may comprises hydrophilic surface groups to provide lubricity, whilst also providing a bacteria-repellent effect, especially useful preventing discomfort and/or infection for a user inserting multiple catheters per day.

Claims

1. An intermittent catheter comprising a surface comprising a calixarene.

2. An intermittent catheter as claimed in claim 1, wherein said calixarene is bonded to the surface of the intermittent catheter via one or more surface-linker groups on a rim of the calixarene, said surface-linker groups being bonded to the surface of the device via covalent bonds, ionic bonds, hydrogen bonds, or Van der Waals forces.

3. An intermittent catheter according to claim 2, wherein an opposing rim of the calixarene is substituted by one or more polyethylene glycol, polypropylene glycol or polytrimethylene glycol groups, or a mixture thereof, forming glycol surface-linker groups.

4. An intermittent catheter according to claim 3, wherein said glycol linker groups are attached to the calixarene via (C.sub.3 to C.sub.16)alkyl spacer groups, said glycol groups, each independently, have from 2 to 250 repeating glycol units and may be optionally terminated by hydrogen or (C.sub.1 to C.sub.4)alkyl, said (C.sub.3 to C.sub.16)alkyl spacer groups may be optionally substituted by one or more fluoro, methyl or ethyl groups and may optionally contain one or more unsaturated bonds.

5. An intermittent catheter according to claim 4, wherein said glycol groups are attached to the alkylene spacer group directly via the oxygen of the glycol or via another linker group.

6. An intermittent catheter according to claim 3, wherein the glycol linker group is selected from carbonate, carbamate, urea, phosphate and triazole.

7. An intermittent catheter according to a claim 2, wherein the calixarene is bonded to the surface of the intermittent catheter via 2 to 8 surface-linker groups.

8. An intermittent catheter according to claim 3, wherein a rim of the calixarene is substituted by one or more polyethylene glycol groups.

9. (canceled)

10. An intermittent catheter according to claim 1, wherein said calixarene is derived from a compound of formula (I) ##STR00006## wherein X is H, (C.sub.1-C.sub.30)alkyl, NH.sub.2, NH(C.sub.1-C.sub.30)alkyl, N(C.sub.1-C.sub.30)alkyl2, CH.sub.2NH(C.sub.1-C.sub.30)alkyl, OH, O(C.sub.1-C.sub.30)alkyl or OCH.sub.2CO.sub.2(C.sub.1-C.sub.30)alkyl; Y is OH, O(C.sub.1-C.sub.30)alkyl, OCH.sub.2CO.sub.2(C.sub.1-C.sub.30)alkyl, H, (C.sub.1-C.sub.30)alkyl, NH.sub.2, NH(C.sub.1-C.sub.30)alkyl, N(C.sub.1-C.sub.30)alkyl.sub.2 or CH.sub.2NH(C.sub.1-C.sub.30)alkyl; Z is H, OH or methyl; n is 1, 3 or 5; and R is —(C.sub.1-C.sub.30)alkyl- or —(C.sub.1-C.sub.30)alkylene-L.sup.1-G-R.sup.1 wherein said alkyl or alkylene may be optionally substituted by one or more fluoro, methyl or ethyl groups and may optionally contain one or more unsaturated bonds; L.sup.1 is a bond or a linking group; G is —O(CH.sub.2CH.sub.2O).sub.m-, —O(CH.sub.2CH(CH.sub.3)O).sub.m-, —(O(CH(CH.sub.3)CH.sub.2O).sub.m-, or —O(CH.sub.2CH.sub.2CH.sub.2O).sub.m-; m is 2 to 250; R.sup.1 is H or (C.sub.1-C.sub.30)alkyl; and wherein each X, Y, Z, R and R.sup.1 group may be the same or different.

11. An intermittent catheter according to claim 10, wherein X is H and Y is OH.

12. An intermittent catheter according to any one of claim 10, wherein X is H and R is —CH.sub.2C.sub.8F.sub.17.

13. An intermittent catheter according to claim 10, wherein R is —(C.sub.10)alkylene-L.sup.1-G-R.sup.1.

14. An intermittent catheter according to claim 10, wherein L.sup.1 is a linking group selected from carbonate, carbamate, urea, phosphate and triazole.

15. An intermittent catheter according to claim 10, wherein G is —O(CH.sub.2CH.sub.2O).sub.m-.

16. An intermittent catheter according to claim 10, wherein R.sup.1 is H or methyl.

17. An intermittent catheter according to claim 10, wherein m is 3 to 150.

18. An intermittent catheter according to claim 10, wherein said calixarene is bonded to the surface of the device via surface-linker groups substituted for any one or more of the X or Y substituents, or a combination thereof

19. An intermittent catheter according to claim 18, wherein the surface-linker groups X or Y, or a combination thereof, on the calixarene are derived from acid chloride, chloroformate, vinyl, acrylate, or silane functional groups.

20. (canceled)

21. An intermittent catheter according to claim 10, wherein R is —(C.sub.3-C.sub.16)alkylene-OH or —(C.sub.2-C.sub.15)alkylene-CH.sub.2═CH.sub.2 wherein said alkylene may be optionally substituted by one or more fluoro, methyl or ethyl groups and may optionally contain one or more unsaturated bonds; and wherein each X, Y, Z and R group may be the same or different; with the proviso that when X is H, OH, CH.sub.3 or OCH.sub.3; Y is OH; Z is H; and n is 1; R is not —(C.sub.8)alkylene-CH.sub.2═CH.sub.2.

22. An intermittent catheter according to claim 18, wherein said calixarene is ##STR00007## wherein R is —(C.sub.10)alkylene-OC(O)O—(CH.sub.2CH.sub.2O).sub.m—OH; and R.sup.3 is (C.sub.3)alkylene-Si(OEt).sub.3 or a combination thereof.

23-27. (canceled)

Description

DETAILED DESCRIPTION OF THE INVENTION

[0204] In order that the invention may be more clearly understood embodiments thereof will now be described, by way of example only:

Example 1

[0205] A first embodiment of an intermittent catheter of the invention comprises an intermittent catheter formed of a thermoplastic elastomeric material. The outer surface of the intermittent catheter is coated with a calixarene of formula:

##STR00004##

[0206] wherein R is —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2OC(O)O—(CH.sub.2CH.sub.2O).sub.7—CH.sub.3, and R.sup.3 is -CH.sub.2CH.sub.2CH.sub.2Si(OEt).sub.3.

[0207] The calixarene may be prepared as described in GB2498356.

[0208] The silane groups present in the calixarene act as surface-linker groups that allow the calixarene to bond to the outer surface of the intermittent catheter.

[0209] The intermittent catheter is used in the conventional manner.

[0210] The combination of the calixarene and the thermoplastic elastomeric material on the outer surface of the intermittent catheter allows the intermittent catheter to possess high lubricity and bacteria repellent properties, making it both easier to insert and remove, and safer to use with a decreased risk of developing infections.

Example 2

[0211] A second embodiment of an intermittent catheter of the invention comprises an intermittent catheter formed of polyethylene. The outer surface of the intermittent catheter is coated with a calixarene of formula (I); wherein X is H, Y is OH, Z is H, R is —CH.sub.2C.sub.8F.sub.17, and n is 1.

[0212] The calixarene may be prepared as described in WO9739077.

[0213] The intermittent catheter is used in the conventional manner.

[0214] The combination of the calixarene and the polyethylene material on the outer surface of the intermittent catheter allows the intermittent catheter to possess high lubricity and bacteria repellent properties, making it both easier to insert and remove, and safer to use with a decreased risk of developing infections.

Example 3

[0215] A third embodiment of the invention comprises an intermittent catheter that is formed of a thermoplastic elastomeric material (polyolefin—either polyethylene or polypropylene). The outer surface of the intermittent catheter is coated with a silver alloy and hydrogel coating as a further bacteria-repellent coating material, alongside a calixarene of formula

##STR00005##

[0216] wherein R is —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2OC(O)O—(CH.sub.2CH.sub.2O).sub.7—CH.sub.3, and R.sup.3 is —CH.sub.2CH.sub.2CH.sub.2Si(OEt).sub.3.

[0217] The calixarene may be prepared as described in GB2498356.

[0218] The present intermittent catheter is used in the conventional manner.

[0219] As in Example 1, the combination of the calixarene and the thermoplastic elastomeric material on the surface of the intermittent catheter allows the intermittent catheter to possess high lubricity and bacteria repellent properties, making it both easier to insert and remove, and safer to use, with a decreased risk of developing infections. The additional silver alloy and hydrogel coating further inhibits bacterial growth on the intermittent catheter surface and enhances its lubricity further, making it easier and less irritating to insert and remove the intermittent catheter.

[0220] Suitable methods for coating the intermittent catheters of Examples 1-3 with the respective calixarenes are known to those skilled in the art. They include methods described in the following: WO97/39077, WO2005/112570, U.S. Pat. Nos. 6,702,850, 6,602,287, 5,053,048, 7,070,798 and US 2002/0102405.

[0221] The above embodiments are described by way of example only. Many variations are possible without departing from the scope of the invention as defined in the appended claims.