Transdermally deliverable opioid prodrugs, abuse-resistant compositions and methods of using opioid prodrugs
AssigneeAllTranz Inc.
InventorsAudra Lynn Stinchcomb, Miroslaw Jerzy Golinski, Dana Carmel Hammell, Jeffrey Lynn Howard
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Abstract
Described herein are opioid prodrugs, methods of making opioid prodrugs, formulations comprising opioid prodrugs, and methods of using opioid prodrugs. One embodiment described herein relates to the transdermal administration of a buprenorphine prodrug in an abuse-resistant formulation for treating and preventing diseases and/or disorders.
Claims22
A compound having the formula:
- wherein R1 is selected from the group consisting of oxygenated alkyl carbonate, alkyl carbonate and oxygenated ester.
A compound selected from the group consisting of:
A pharmaceutical composition comprising:
- (a) a buprenorphine prodrug selected from the group consisting of:
- (b) a pharmaceutical excipient.
A method of treating a medical condition in a mammal comprising the step of transdermally administering a buprenorphine prodrug from the group consisting of:
A method of transdermally administering a buprenorphine prodrug to a mammal comprising the steps of:
- (a) selecting a compound from the group consisting of:
- (b) combining a compound selected in step (a) with a pharmaceutically acceptable excipient to form a pharmaceutical composition;
- and
- (c) contacting the pharmaceutical composition formed in step (b) with the skin of the mammal.
A method for transdermally delivering a buprenorphine prodrug to a mammal comprising the steps of:
- (a) selecting a buprenorphine prodrug from the group consisting of:
- (b) selecting a naltrexone prodrug of having the formula
- wherein R3 is selected from the group consisting of:
- H;
- —COC(CH3)3;
- —COCH(CH3)2;
- —COCH2CH(CH3)2;
- —COCH(CH2CH3)2;
- —CON(CH2CH3)2;
- —CON(CH(CH3)2)2;
- —COOCH(CH3)2;
- and —CO(CH2)2OCH3;
- (c) combining the compounds selected in (a) and (b) with a pharmaceutically acceptable excipient to form a pharmaceutical composition;
- and
- (d) contacting the pharmaceutical composition with the skin of the mammal.
A prodrug of buprenorphine having an in vitro transdermal flux enhancement of greater than one relative to buprenorphine.
A prodrug of buprenorphine having an in vitro transdermal flux (nmol/cm2/hr) greater than buprenorphine.
A prodrug of buprenorphine having a twenty-four hour cumulative amount (nmol) of in vitro transdermal permeation greater than buprenorphine.
Dependencies are inferred from the claim text.