US2016051535A1PendingUtilityA1

Morphinan Derivatives for the Treatment of Drug Overdose

Assignee: ALKERMES PHARMA IRELAND LTDPriority: Dec 4, 2009Filed: Aug 25, 2015Published: Feb 25, 2016
Est. expiryDec 4, 2029(~3.3 yrs left)· nominal 20-yr term from priority
A61P 25/30A61P 25/36A61K 31/485A61K 31/4748C07D 221/28C07D 221/22
48
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Claims

Abstract

The instant application relates to morphinan derivatives of Formula I with sustained effectiveness in treating drug toxicity and overdose:

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A method of treating drug toxicity or overdose in a subject in need thereof comprising administrating a compound of Formula I: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt, ester metabolite or prodrug wherein; 
         R 1  is —(CH 2 ) n -c-C 4 H 7 , —(CH 2 ) n -c-C 5 H 9 , —(CH 2 ) n —CH═CH 2  or —(CH 2 ) n —CH═C(CH 3 ) 2  wherein n is independently 0, 1, 2 or 3; 
         R 2  is —CONH 2  or —CSNH 2 ; 
         R 3  and R 4  are independently H, —OH or together R 3  and R 4  form an —O— or —S— group; 
         R 5  is H or C 1 -C 8  alkyl; and 
         R 6  and R 7  are independently H, —OH, OCH 3  or together R 6  and R 7  form a ═O or ═CH 2  group. 
       
     
     
         2 . The method according to any one of  claim 1 , wherein said drug toxicity or overdose is resulting from opioid administration to a non-dependent patient. 
     
     
         3 . The method according to any one of  claim 2 , wherein said subject is an opioid experienced, non-dependent opioid user. 
     
     
         4 . The method according to any one of  claim 1 , wherein said compound of Formula I is administered in a daily dose of about 3 to about 20 mg/day. 
     
     
         5 . The method according to  claim 4 , wherein said daily dose is about 10 mg/day. 
     
     
         6 . The method according to  claim 1 , wherein administration of a compound of Formula I reduces symptoms of drug toxicity or overdose over a period of at least about 15 to about 30 minutes. 
     
     
         7 . The method according to  claim 6 , wherein symptoms of drug overdose are reduced for a period of at least one hour. 
     
     
         8 . The method according to  claim 6 , wherein symptoms of drug overdose are reduced for a period of at least two hours. 
     
     
         9 . The method according to  claim 6 , wherein symptoms of drug overdose are reduced for a period of at least three hours. 
     
     
         10 . The method according to  claim 6 , wherein symptoms of drug overdose are reduced for a period of at least four hours. 
     
     
         11 . The method according to  claim 6 , wherein symptoms of drug overdose are reduced for a period of at least eight hours. 
     
     
         12 . The method according to any one of  claim 6 , wherein said administration comprises about 3 mg to about 20 mg of a compound of Formula I. 
     
     
         13 . The method according to any one of  claim 6 , wherein said symptoms of overdose is selected from decreased respiratory rate, decreased respiratory depth, apnea, comotosis, hypoxia, delirium hypotension, bradycardia, decreased body temperature, urinary retention and pupil miosis. 
     
     
         14 . A method of treating an opioid toxicity or overdose in a subject in need thereof comprising administrating a first opioid receptor antagonist followed by a compound of Formula I: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt, ester or prodrug thereof wherein; 
         R 1  is —(CH 2 ) n -c-C 4 H 7 , —(CH 2 ) n -c-C 5 H 9 , —(CH 2 ) n —CH═CH 2  or —(CH 2 ) n —CH═C(CH 3 ) 2  wherein n is independently 0, 1, 2 or 3; 
         R 2  is —CONH 2  or —CSNH 2 ; 
         R 3  and R 4  are independently H, —OH or together R 3  and R 4  form an —O— or —S— group; 
         R 5  is H or C 1 -C 8  alkyl; and 
         R 6  and R 7  are independently H, —OH, OCH 3  or together R 6  and R 7  form a ═O or ═CH 2  group. 
       
     
     
         15 . The method according to  claim 14 , wherein said first opioid receptor antagonist is naloxone. 
     
     
         16 . The method according to  claim 15 , wherein said subject is an opioid experienced non-dependent opioid user. 
     
     
         17 . The method according to  claim 15 , wherein said administration of compound of Formula I is preceded by said naloxone administration. 
     
     
         18 . The method according to  claim 17 , wherein said naloxone administration reduces symptoms of overdose or toxicity prior to administration of compounds of Formula I. 
     
     
         19 . The method according to  claim 15 , wherein naloxone is administered concurrently with a compound of Formula I. 
     
     
         20 . A method of treating acute opioid toxicity or overdose for a period of over one hour comprising a single administration of a compound of Formula I to a subject in need thereof: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt, ester or prodrug thereof wherein; 
         R 1  is —(CH 2 ) n -c-C 4 H 7 , —(CH 2 ) n -c-C 5 H 9 , —(CH 2 ) n —CH═CH 2  or —(CH 2 ) n —CH═C(CH 3 ) 2  wherein n is independently 0, 1, 2 or 3; 
         R 2  is —CONH 2  or —CSNH 2 ; 
         R 3  and R 4  are independently H, —OH or together R 3  and R 4  form an —O— or —S— group; 
         R 5  is H or C 1 -C 8  alkyl; and 
         R 6  and R 7  are independently H, —OH, OCH 3  or together R 6  and R 7  form a ═O or ═CH 2  group. 
       
     
     
         21 . The method according to  claim 20 , wherein said subject is a non-dependent opioid experienced patient. 
     
     
         22 . The method according to  claim 20 , wherein symptoms of opioid toxicity or overdose are reduced for a period of more than one hour. 
     
     
         23 . The method according to  claim 20 , wherein symptoms of opioid toxicity or overdose are reduced for a period of more than four hours. 
     
     
         24 . The method according to  claim 20 , wherein symptoms of opioid toxicity or overdose are reduced for a period of more than eight hours. 
     
     
         25 . The method according to  claim 20 , wherein symptoms of opioid toxicity or overdose are reduced for a period of more than twenty four hours. 
     
     
         26 . A method for unmonitored treatment of opioid toxicity or overdose in a patient in need thereof comprising administration of a compound of Formula I: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt, ester or prodrug thereof wherein; 
         R 1  is —(CH 2 ) n -c-C 4 H 7 , —(CH 2 ) n -c-C 5 H 9 , —(CH 2 ) n —CH═CH 2  or —(CH 2 ) n —CH═C(CH 3 ) 2  wherein n is independently 0, 1, 2 or 3; 
         R 2  is —CONH 2  or —CSNH 2 ; 
         R 3  and R 4  are independently H, —OH or together R 3  and R 4  form an —O— or —S— group; 
         R 5  is H or C 1 -C 8  alkyl; and 
         R 6  and R 7  are independently H, —OH, OCH 3  or together R 6  and R 7  form a ═O or ═CH 2  group. 
       
     
     
         27 . The method according to  claim 26 , wherein said unmonitored treatment is effective for a period of over one hour.

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