US2009318490A1PendingUtilityA1

Compounds and methods for promoting smoking cessation

Assignee: RES TRIANGLE INSITUTEPriority: Nov 8, 2000Filed: Aug 31, 2009Published: Dec 24, 2009
Est. expiryNov 8, 2020(expired)· nominal 20-yr term from priority
Inventors:F. Ivy Carroll
A61P 43/00A61P 25/34A61P 25/00A61P 25/18A61P 3/04A61P 25/22A61P 25/28A61P 25/16A61P 25/04A61P 25/24A61P 25/08A61P 1/04C07D 487/22A61K 31/4439A61K 31/44
65
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Claims

Abstract

Compounds and methods for promoting smoking cessation. The compounds may be used to treat a variety of other conditions and disease states.

Claims

exact text as granted — not AI-modified
1 - 71 . (canceled) 
   
   
       72 . A method of treating depression, comprising administering to a patient in need thereof an effective amount of a compound represented by formula (II): 
     
       
         
         
             
             
         
       
     
     wherein
 A 3  is —R, —N(R) 2 , —C(═NR)N(R) 2 , or —OR; 
 each Q is, independently, C—X or N, wherein one Q is N and each other Q is C—X; 
 each X is, independently, H, halogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, with the proviso that at least one X is represented by the formula: 
 
     
       
         
         
             
             
         
       
       each S is, independently, halogen, alkyl, alkenyl, alkynyl, phenyl, aralkyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, or two S, taken together with the phenyl group to which they are bonded, form a 2-naphthyl group; 
       c is 1, 2, 3, 4 or 5; 
       Y is a halogen; and 
       each R is, independently, H, alkyl, alkenyl, alkynyl, aryl, or aralkyl; 
       or a pharmaceutically acceptable salt thereof. 
     
   
   
       73 . The method of  claim 72 , wherein c is 1. 
   
   
       74 . The method of  claim 72 , wherein c is 2. 
   
   
       75 . The method of  claim 72 , wherein c is 3. 
   
   
       76 . The method of  claim 72  wherein two of said S, taken together with the phenyl group to which they are bonded, form a 2-naphthyl group. 
   
   
       77 . The method of  claim 72 , wherein c is 1, 2, 3, 4, or 5, and at least one S is halogen, alkyl, alkenyl, alkynyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3  CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, wherein R and Y are as defined in  claim 72 . 
   
   
       78 . The method of  claim 72 , wherein c is 1, 2, 3, 4, or 5, and at least one S is halogen, alkyl, or —NO 2 . 
   
   
       79 . The method of  claim 72 , wherein c is 1, 2, or 3, and at least one S is halogen, alkyl, or —NO 2 . 
   
   
       80 . The method of  claim 72 , wherein c is 1 or 2, and at least one S is halogen, alkyl, or —NO 2 . 
   
   
       81 . The method of  claim 72 , wherein at least one X is halogen or —NH 2 . 
   
   
       82 . The method of  claim 72 , wherein at least one X is halogen, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, wherein R is as defined in  claim 72 . 
   
   
       83 . The method of  claim 72 , wherein A 3  is H or alkyl. 
   
   
       84 . The method of  claim 72 , wherein A 3  is H. 
   
   
       85 . The method of  claim 72 , wherein one Q is N. 
   
   
       86 . The method of  claim 72 , wherein each X is independently selected from the group consisting of H, F, Cl, Br, l, CH 3 , OH, NH 2 , (CH 3 ) 2  N, NHAc, CF 3 SO 3 , subject to said proviso. 
   
   
       87 . The method of  claim 72 , wherein R is H, alkyl or benzyl. 
   
   
       88 . The method of  claim 72 , wherein said alkyl group in the definition of R is represented by the formula —(CH 2 ), —Y, wherein Y is a halogen and n is an integer from 1 to 8. 
   
   
       89 . The method of  claim 72 , wherein the compound is represented by formula (IIa): 
     
       
         
         
             
             
         
       
     
     wherein
 A 3  is as defined in  claim 72 ; 
 X 1 , X 2 , X 3  and X 4  are each, independently, H, halogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, wherein at least one of X 1 , X 2 , X 3 , and X 4  is represented by said formula: 
 
     
       
         
         
             
             
         
       
     
     wherein
 S and c are as defined in  claim 72 ; 
 Y is as defined in  claim 72 ; and 
 R is as defined in  claim 72 . 
 
   
   
       90 . The method of  claim 89 , wherein the compound is represented by formula (IIb): 
     
       
         
         
             
             
         
       
     
     wherein
 A 3  is as defined in  claim 89 ; 
 X 1 , X 3  and X 4  are each, independently, H, halogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN; 
 R is as defined in  claim 89 ; 
 Y is as defined in  claim 89 ; 
 S is as defined in  claim 89 ; and 
 c is as defined in  claim 89 . 
 
   
   
       91 . The method of  claim 90 , wherein c is 1. 
   
   
       92 . The method of  claim 90 , wherein c is 2. 
   
   
       93 . The method of  claim 90 , wherein c is 3. 
   
   
       94 . The method of  claim 90 , wherein two of said S, taken together with the phenyl group to which they are bonded, form a 2-naphthyl group. 
   
   
       95 . The method of  claim 90 , wherein c is 1, 2, 3, 4, or 5, and at least one S is halogen, alkyl, alkenyl, alkynyl, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, wherein R and Y are as defined in  claim 90 . 
   
   
       96 . The method of  claim 90 , wherein c is 1, 2, 3, 4, or 5, and at least one S is halogen, alkyl, or —NO 2 . 
   
   
       97 . The method of  claim 90 , wherein c is 1, 2, or 3, and at least one S is halogen, alkyl, or —NO 2 . 
   
   
       98 . The method of  claim 90 , wherein c is 1 or 2, and at least one S is halogen, alkyl, or —NO 2 . 
   
   
       99 . The method of  claim 90 , wherein at least one of X 1 , X 3 , and X 4  is halogen or —NH 2 . 
   
   
       100 . The method of  claim 90 , wherein at least one of X 1 , X 3 , and X 4  is halogen, —OH, —OR, —CH 2 —CO 2 R, —CO—R, —CO 2 R, —N(R) 2 , —NR—CO—R, —CO—N(R) 2 , —NRCO 2 R, —SO 3 CF 3 , —NO 2 , —N 3 , —CF 3 , —CH═CHY, or —CN, wherein R is as defined in  claim 90 . 
   
   
       101 . The method of  claim 90 , wherein A 3  is H or alkyl. 
   
   
       102 . The method of  claim 90 , wherein A 3  is H. 
   
   
       103 . The method of  claim 90 , wherein X 1 , X 3 , and X 4  are each hydrogen. 
   
   
       104 . The method of  claim 90 , wherein R is H, alkyl or benzyl. 
   
   
       105 . The method of  claim 90 , wherein said alkyl group in the definition of R is represented by the formula —(CH 2 ) n —Y, wherein Y is a halogen and n is an integer from 1 to 8. 
   
   
       106 . The method of  claim 90 , wherein X 1  is fluorine and X 3  and X 4  are hydrogen. 
   
   
       107 . The method of  claim 106 , wherein c is 1. 
   
   
       108 . The method of  claim 107 , wherein S is fluorine, chlorine, methoxy, —NO 2  or —NH 2 . 
   
   
       109 . The method of  claim 108 , wherein A 3  is hydrogen. 
   
   
       110 . The method of  claim 90 , wherein X 1  is —Cl, —Br, NH 2  or OH and X 3  and X 4  are hydrogen. 
   
   
       111 . The method of  claim 110 , wherein c is 1. 
   
   
       112 . The method of  claim 111 , wherein S is —Cl, —Br, —F, —NO 2 , methoxy, —NH 2  or N(CH 3 ) 3 . 
   
   
       113 . The method of  claim 112 , wherein A 3  is hydrogen. 
   
   
       114 . The method of  claim 72 , wherein at least one atom in the compound is a member selected from the group consisting of  3 H,  11 C,  14 C,  35 S,  18 F,  123 I,  125 I, and  131 I. 
   
   
       115 . The method of  claim 114 , wherein at least one atom in the compound is a member selected from the group consisting of  3 H,  11 C,  18 F, and  123 I. 
   
   
       116 . The method of  claim 114 , wherein at least one X is  18 F,  123 I,  125 I, or  131 I. 
   
   
       117 . The method of  claim 114 , wherein at least one X is a phenyl group substituted with one or more of  18 F,  123 I,  125 I, or  131 I.

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