Local delivery of drugs from self assembled coatings

1. A transient medical device having a surface with a self assembling coating deposited thereon, said self assembling coating comprising (i) an oligofluorinated oligomer of formula (XV-C):

wherein

F T is a polyfluoroorgano group;

L is a linker;

X 1 is H, CH 3 , or CH 2 CH 3 ;

X 2 is H, CH 3 , or CH 2 CH 3 ; and

n is an integer from 5 to 50;

or

formula (XVII):

wherein

F T is a polyfluoroorgano group;

L 2 is a substituted or unsubstituted C 1-10 alkyl, a heteroalkyl of 1 to 10 atoms, a C 2-10 alkene, a C 2-10 alkyne, a C 5-10 aryl, a cyclic system of 3 to 10 atoms, —(CH 2 CH 2 O) q CH 2 CH 2 — in which q is an integer of 1 to 10;

X 1 is H, CH 3 , or CH 2 CH 3 ;

X 2 is H, CH 3 , or CH 2 CH 3 ; and

n is an integer from 5 to 50;

and (ii) a biologically active agent, wherein

said transient medical device comprises an energy generating element, said energy generating element being capable of disrupting said self assembling coating when activated;

or

said transient medical device is a deformable transient medical device which, upon being deployed into a deformed configuration, mechanically disrupts said self assembling coating.

2. A method for delivering a biologically active agent to a site in a vessel, said method comprising inserting into said vessel a transient medical device of claim 1 , positioning said transient medical device near said site, and disrupting the coating on said transient medical device deliver said biologically active agent to said site.

3. A method for inhibiting restenosis at a site in a vessel, said method comprising inserting into said vessel a transient medical device of claim 1 , and activating said energy generating element, wherein said biologically active agent is selected from antiproliferative agents and rapamycin macrolides.

4. A method for inhibiting restenosis at a site in a vessel, said method comprising inserting into said vessel a deformable transient medical device of claim 1 , and deploying said deformable transient medical device into a deformed configuration, wherein said biologically active agent is selected from antiproliferative agents and rapamycin macrolides.

5. The method of claim 2 , comprising a bioactive agent and an oligofluorinated oligomer wherein the oligofluorinated oligomer comprises a structure according to formula (XV-C):

Wherein

FT is s a polyfluoroorgano group;

L is a linker;

X 1 is H, CH 3 , or CH 2 CH 3 ;

X 2 is H, CH 3 , or CH 2 CH 3 ; and

n is an integer from 5 to 50;

or

wherein the oligofluorinated oligomer comprises a structure according to formula (XVII):

wherein

F T is a polyfluoroorgano group;

L 2 is a substituted or unsubstituted C1-10 alkyl, a heteroalkyl of 1 to 10 atoms, a C 2-10 alkene, a C 2-10 alkyne, a C 5-10 aryl, a cyclic system of 3 to 10 atoms, —(CH 2 CH 2 O) q CH 2 CH 2 — in which q is an integer of 1 to 10;

X 1 is H, CH 3 , or CH 2 CH 3 ,

X 2 is H, CH 3 , or CH 2 CH 3 ; and

n is an integer from 5 to 50.

6. The method of claim 5 , wherein said linker is described by formula (XVI):

G 1 -(Z 1 ) o —(Y 1 ) u —(Z 2 ) s —(R 10 )—(Z 3 ) t —(Y 2 ) v —(Z 4 ) p -G 2   (XVI)

wherein

G 1 is a bond between said polyfluoroorgano group and said linker;

G 2 is a bond between said linker and an oxygen atom;

Z 1 , Z 2 , Z 3 , and Z 4 each, independently, is selected from O, S, and NR 11 ;

R 11 is hydrogen or a C 1-10 alkyl group;

Y 1 and Y 2 are each, independently, selected from carbonyl, thiocarbonyl, sulphonyl, or phosphoryl;

o, p, s, t, u, and v are each, independently, 0 or 1; and

R 10 is a substituted or unsubstituted C 1-10 alkyl, a heteroalkyl of 1 to 10 atoms, a C 2-10 alkene, a C 2-10 alkyne, a C 5-10 aryl, a cyclic system of 3 to 10 atoms, —(CH 2 CH 2 O) q CH 2 CH 2 — in which q is an integer of 1 to 10, or a chemical bond linking G 1 -(Z 1 ) o —(Y 1 ) u —(Z 2 ) s — to —(Z 3 ) t —(Y 2 ) v —(Z 4 ) p -G 2 .

7. The method of claim 5 , wherein said polyfluoroorgano group is a polyfluoroalkyl having a molecular weight of between 100-1,500 Da;

or

said polyfluoroorgano group is a radical of the general formula CF 3 (CF 2 ) r CH 2 CH 2 — or CF 3 (CF 2 ) s (CH 2 CH 2 O) χ —, wherein r is an integer from 2 to 20, χ is an integer from 1 to 10, and s is an integer from 1 to 20

or

said polyfluoroorgano group is a radical of the general formula CH m F (3-m) (CF 2 ) r CH 2 CH 2 — or CH m F (3-m) (CF 2 ) s (CH 2 CH 2 O) χ —, wherein m is 0, 1, 2, or 3; χ is an integer between 1 and 10; r is an integer between 2 and 20; and s is an integer between 1 and 20;

or

said polyfluoroorgano group is selected from (CF 3 )(CF 2 ) 5 CH 2 CH 2 O—, (CF 3 )(CF 2 ) 7 CH 2 CH 2 O—, (CF 3 )(CF 2 ) 5 CH 2 CH 2 O—, CHF 2 (CF 2 ) 3 CH 2 O—, and (CF 3 )(CF 2 ) 2 CH 2 O—, 1H,1H,2H,2H-perfluoro-1-decanol; 1H,1H,2H,2H-perfluoro-1-octanol; 1H,1H,5H-perfluoro-1-pentanol; and 1H,1H, perfluoro-1-butanol, and mixtures thereof.

8. The method of claim 5 , wherein said biologically active agent is a hydrophobic drug.

9. The method of claim 8 , wherein said hydrophobic drug is selected from antiproliferative agents and rapamycin macrolides.

10. The method of claim 9 , wherein said hydrophobic drug is an antiproliferative agent selected from methotrexate, trimetrexate, gemcitabine, vinblastine, vincristine, etoposide, teniposide, topotecan, irinotecan, camptothecin, 9-aminocamptothecin, docetaxel, daunorubicin, doxorubicin, dactinomycin, idarubincin, bleomycin, and tamoxifen, rapamycin, CCI-779, Everolimus, ABT-578, and paclitaxel.