Ibogaine-related compounds and corresponding methods

Abstract

The present invention relates to Ibogaine derivatives and related methods. It more specifically relates to deutero- and fluoro-derivatives of Ibogaine and related methods. In one aspect, the present invention provides a compound. The structure of the compound is shown as compound 1 in FIG. 1. In another aspect, the present invention provides a method of treating an addiction disorder. The method comprises administration of compound 1. In another aspect, the present invention provides a method of treating an anxiety-related disorder or impulse control disorder. The method comprises administration of compound 1.

1 . A compound, wherein the compound is of the following structure: 
       
         
           
           
               
               
           
         
         wherein, R 1  is H, D, OH, CH 2 OH, CD 2 OH, CH 2 CH 2 OH, CH 2 CD 2 OH, CD 2 CD 2 OH, OCH 3 , OCDH 2 , OCD 2 H, OCD 3 , CH 2 OCDH 2 , CH 2 OCD 2 H, CH 2 OCD 3 , CH 2 CH 2 OCDH 2 , CH 2 CH 2 OCD 2 H, CH 2 CH 2 OCD 3 , CH 2 CD 2 OCDH 2 , CH 2 CD 2 OCD 2 H, CH 2 CD 2 OCD 3 , CD 2 CD 2 OCDH 2 , CD 2 —CD 2 OCD 2 H, CD 2 CD 2 OCD 3 , CH 2 CH 2 OCH 2 OCH 2 CH 2 OCH 3 , CH 2 CH 2 OCH 2 OCH 2 CH 2 OCDH 2 , CH 2 CH 2 OCH 2 OCH 2 CH 2 O—CD 2 H, CH 2 CH 2 OCH 2 OCH 2 CH 2 OCD 3 , CH 2 CH 2 OCH 2 OCH 2 CD 2 —OCD 3 , CH 2 CH 2 OCH 2 OCD 2 CD 2 OCD 3 , CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 3 , CH 2 CH 2 O—CH 2 CH 2 OCH 2 CH 2 OCDH 2 , CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCD 2 H, CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 —OCD 3 , CH 2 CH 2 OCH 2 CH 2 OCH 2 CD 2 OCD 3 , CH 2 CH 2 OCH 2 CH 2 OCD 2 CD 2 OCD 3 , OCF 3 , CH 2 OCF 3 , or CD 2 OCF 3 ; R 2  is H, D, CO 2 H, CO 2 R 12  where R 12  is a pharmaceutically acceptable salt (e.g., sodium, fumaric, etc.), CO 2 CH 3 , CO 2 CH 2 D, CO 2 CHD 2 , CO 2 CD 3 , CO 2 CH 2 CH 3 , CO 2 CH 2 CD 3 , CO 2 CD 2 CD 3 , C(O)NH 2 , C(O)NHCH 3 , C(O)NHCD 3 , C(O)N(CH 3 ) 2 , C(O)N(CH 3 )(CD 3 ), or C(O)N(CD 3 ) 2 ; R 3  is H, C(O)OCH 3 , C(O)OCD 3 , C(O)CH 2 CH 3 , C(O)CH 2 CD 3 , C(O)CD 2 CD 3 , C(O)OCH 2 CH 2 OCH 3 , C(O)OCH 2 CH 2 OCD 3 , C(O)OCH 2 CD 2 OCD 3 , C(O)OCD 2 CD 2 OCD 3 , or C(O)OCF 3 ; R 4  is H, D, F, Cl, Br, I, CH 3 , CF 3 , CH 2 CH 3 , CO 2 H, CO 2 CH 3 , C(O)NH 2 , C(O)NHCH 3 , C(O)N(CH 3 ) 2 , OH, OCH 3 , OCD 3 , or CN; R 5  is H, D, F, Cl, Br, I, CH 3 , CF 3 , CH 2 CH 3 , CO 2 H, CO 2 CH 3 , C(O)NH 2 , C(O)NHCH 3 , C(O)N(CH 3 ) 2 , OH, OCH 3 , OCD 3 , or CN; R 6  is H or D; R 7  is H or D; R 8  is H or D; R 9  is H or D; R 10  is H or D; R 11  is H or D; “n” is an integer selected from 1, 2, 3, 4, 5, 6, 7 and 8. 
       
     
     
         2 . A method of treating an addiction disorder comprising administration of a compound according to  claim 1 . 
     
     
         3 . A method of treating an anxiety-related disorder or impulse control disorder comprising administration of a compound according to  claim 1 .