US2002013367A1PendingUtilityA1
Antiproliferative and neurotrophic molecules

Priority: Aug 30, 1994Filed: Aug 14, 2001Published: Jan 31, 2002
Est. expiryAug 30, 2014(expired)· nominal 20-yr term from priority
A61P 43/00A61P 3/10A61P 25/14A61P 25/00A61P 25/16A61P 25/28C07C 57/02C07C 57/18C07C 51/38A61P 17/02C07C 53/128C07C 57/03
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References
Claims
Abstract

Neurotrophic and antiproliferative compounds related to the antiepileptic drug valproate are provided. These compounds are useful for promoting neuronal function as in neurodegenerative disorders and for treating neoplastic disease.
Claims

exact text as granted — not AI-modified
We claim:  
     
         1 . Compounds of formula (I)  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  is —C≡—CH, —CH═CH 2 , or —CH 2 -CH 3 ,  
 R 2  is a saturated, unsaturated, branched and/or unbranched C 1 -C 30  alkyl group, optionally comprising an aliphatic or aromatic C 3-9  cyclohydrocarbon or heterocyclic group; and  
 M is a hydrogen or a metal atom,  
 and enantiomeres thereof and pharmaceutical acceptable salts thereof; with the proviso that the compound of formula (I) is not 2-n-propyl-4-pentynoic acid, or 2-n-propyl-4-pentenoic acid (4-en-VPA), and when R 1  is —CH 2 -CH 3 , R 2  is a C 5  to C 30  alkyl.  
 
     
     
         2 . The compounds according to  claim 1  wherein R 1  is —C≡CH or —CH═CH 2  and R 2  is unbranched and —(CH 2 ) 1-9 —CH 3 .  
     
     
         3 . The compound according to  claim 2  wherein R 2  is —(CH 2 ) 3-6 —CH 3 .  
     
     
         4 . The compounds according to  claim 2  wherein R 2  is —(CH 2 ) 4-5 —CH 3 .  
     
     
         5 . The compounds according to  claim 4  wherein R 1  is —C≡CH.  
     
     
         6 . The S enantiomer of the compounds according to  claim 1 .  
     
     
         7 . The compounds according to  claim 1 , selected from the group consisting of: 
 2-n-propyl-4-pentynoic acid    2-n-prop-1 1 -enyl-4-pentynoic acid    2-n-prop-2 1 -enyl4-pentynoic acid    2-i-propyl-4-pentynoic acid    2-i-propenyl-4-pentynoic acid    2-n-butyl-4-pentynoic acid    2-n-but-1 1 -enyl-4-pentynoic acid    2-n-but-2 1 -enyl-4-pentynoic acid    2-n-but-3 1 -enyl-4-pentynoic acid    2-(1 1 -methylbutyl)-4-pentynoic acid    2-(1 1 -methylprop-1 1 -enyl)-4-pentynoic acid    2-(1 1 -methylprop-2 1 -enyl)-4-pentynoic acid    2-(2 1 -methylpropyl)-4-pentynoic acid    2-(2 1 -methylprop-1 1 -enyl)-4-pentynoic acid    2-(2 1 -methylprop-2 1 -enyl)-4-pentynoic acid    2-tert.-butyl-4-pentynoic acid    2-n-pentyl-4-pentynoic acid    2-(1 1 -methylbutyl)-4-pentynoic acid    2-(2 1 -methylbutyl)-4-pentynoic acid    2-(3 1 -methylbutyl)-4-pentynoic acid    2-(1 1 ,1 1 -dimethylpropyl)-4-pentynoic acid    2-(1 1 ,2 1 -dimethylpropyl)-4-pentynoic acid    2-(2 1 ,2 1 -dimethylpropyl)-4-pentynoic acid    2-n-hexyl-4-pentynoic acid    2-n-hex-1 1 -enyl-4-pentynoic acid    2-n-hex-2 1 -enyl-4-pentynoic acid    2-n-hex-3 1 -enyl-4-pentynoic acid    2-n-hex-4 1 -enyl-4-pentynoic acid    2-n-hex-5 1 -enyl-4-pentynoic acid    2-(1 1 -methylpentyl)-4-pentynoic acid    2-(1 1 -methylpent-1 1 -enyl)-4-pentynoic acid    2-(1 1 -methylpent-2 1 -enyl)-4-pentynoic acid    2-(1 1 -methylpent-3 1 -enyl)-4-pentynoic acid    2-(1 1 -methylpent-4 1 -enyl)-4-pentynoic acid    2-(2 1 -methylpentyl)-4-pentynoic acid    2-(2 1 -methylpent-1 1 -enyl)-4-pentynoic acid    2-(2 1 -methylpent-2 1 -enyl)-4-pentynoic acid    2-(2 1 -methylpent-3 1 -enyl)-4-pentynoic acid    2-(2 1 -methylpent-4 1 -enyl)-4-pentynoic acid    2-(3 1 -methylpentyl)-4-pentynoic acid    2-(3 1 -methylpent-1 1 -enyl)-4-pentynoic acid    2-(3 1 -methylpent-2 1 -enyl)-4-pentynoic acid    2-(3 1 -methylpent-3 1 -enyl)-4-pentynoic acid    2-(3 1 -methylpent-4 1 -enyl)-4-pentynoic acid    2-(4 1 -methylpentyl)-4-pentynoic acid    2-(4 1 -methylpent-1 1 -enyl)-4-pentynoic acid    2-(4 1 -methylpent-2 1 -enyl)-4-pentynoic acid    2-(4 1 -methylpent-3 1 -enyl)-4-pentynoic acid    2-(4 1 -methylpent-4 1 -enyl)-4-pentynoic acid    2-(1 1 ,1 1 -dimethylbutyl)-4-pentynoic acid    2-(1 1 ,1 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid    2-(1 1 ,1 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid    2-(1 1 ,2 1 -dimethylbutyl)-4-pentynoic acid    2-(1 1 ,2 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid    2-(1 1 ,2 1 ,dimethylbut-2 1 -enyl)-4-pentynoic acid    2-(1 1 ,2 1 ,dimethylbut-3 1 -enyl)-4-pentynoic acid    2-(1 1 ,3 1 -dimethylbutyl)-4-pentynoic acid    2-(1 1 ,3 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid    2-(1 1 ,3 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid    2-(1 1 ,3 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid    2-(2 1 ,2 1 -dimethylbutyl)-4- pentynoic acid    2-(2 1 ,2 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid    2-(2 1 ,3 1 -dimethylbutyl)-4-pentynoic acid    2-(2 1 ,3 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid    2-(2 1 ,3 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid    2-(2 1 ,3 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid    2-(3 1 ,3 1 -dimethylbutyl)-4-pentynoic acid    2-(3 1 ,3 1 -dimethylbut-1 1 -enyl)-4--pentynoic acid    2-(1 1 ,1 1 ,2 1 -trimethylpropyl)-4-pentynoic acid    2-(1 1 ,1 1 ,2 1 -trimethylprop-2 1 -enyl)-4-pentynoic acid    2-(1 1 ,2 1 ,2 1 -trimethylpropyl)-4-pentynoic acid    2-n-heptyl-4-pentynoic acid    2-(1 1 -methylhexyl)-4-pentynoic acid    2-(2 1 -methylhexyl)-4-pentynoic acid    2-(3 1 -methylhexyl)-4-pentynoic acid    2-(4 1 -methylhexyl)-4-pentynoic acid    2-(5 1 -methylhexyl)-4-pentynoic acid    2-(1 1 ,1 1 -dimethylpentyl)-4-pentynoic acid    2-(1 1 ,2 1 -dimethylpentyl)-4-pentynoic acid    2-(1 1 ,3 1 -dimethylpentyl)-4-pentynoic acid    2-(1 1 ,4 1 -dimethylpentyl)-4-pentynoic acid    2-(2 1 ,2 1 -dimethylpentyl)-4-pentynoic acid    2-(2 1 ,3 1 -dimethylpentyl)-4-pentynoic acid    2-(2 1 ,4 1 -dimethylpentyl)-4-pentynoic acid    2-(3 1 ,3 1 -dimethylpentyl)-4-pentynoic acid    2-(3 1 ,4 1 -dimethylpentyl)-4-pentynoic acid    2-(4 1 ,4 1 -dimethylpentyl)-4-pentynoic acid    2-(1 1 ,1 1 ,2 1 -trimethylbutyl)-4-pentynoic acid    2-(1 1 ,1 1 ,3 1 -trimethylbutyl)-4-pentynoic acid    2-(1 1 ,2 1 ,3 1 -trimethylbutyl)-4-pentynoic acid    2-(2 1 ,2 1 ,3 1 -trimethylbutyl)-4-pentynoic acid    2-(2 1 ,3 1 ,3 1 -trimethylbutyl)-4-pentynoic acid.    
     
     
         8 . The compounds according to  claim 7  selected from the group consisting of 2-n-butyl-4-pentynoic acid; 2-n-pentyl-4-pentynoic acid and 2-n-hexyl-4-pentynoic acid.  
     
     
         9 . A pharmaceutical composition for inhibiting cell mitosis comprising an effective amount of at least one compound according to any one of  claims 1  to  8  and a pharmaceutically acceptable carrier.  
     
     
         10 . A method of preparing compounds having the general formula (I)  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  is —C≡CH, —CH═CH 2 , or —CH 2 -CH 3 ,  
 R 2  is a saturated, unsaturated, branched and/or unbranched C 1-30  alkyl group, optionally substituted with an aliphatic or aromatic C 3-9  cyclohydrocarbon or heterocyclic group; and  
 M is a hydrogen or a metal atom, comprising;  
 combining a malonic acid diester with a first halide having the general formula (VII) 
 R 2 —X  (VII) 
 wherein R 2  has the meaning given previously and X is halogen, to form a 2-alkyl malonic acid diester, and combining the 2-alkyl malonic acid diester with a second halide having the general formula (VIII) 
 R 1 —CH 2 —X  (VIII) 
 wherein R 1  has the meaning given previously; or combining the malonic acid diester with the second halide having the general formula (VIII) to form a 2-alkyl malonic acid diester; and  
 combining the first halide having the general formula (VII) to form a compound of formula (IX)  
                     
 wherein R 5  is an alkyl group; and hydrolyzing and decarboxylating the compound of formula (IX) to form the compound of formula (I); and optionally converting the compound of formula (I) to a salt.  
 
     
     
         11 . The method according to  claim 10  wherein R 1  is —C≡CH and R 2  is —(CH 2 ) 1-9 —CH 3 .  
     
     
         12 . The method according to  claim 11  wherein R 2  is —(CH 2 ) 3-6 —CH 3 .  
     
     
         13 . The method according to  claim 12  wherein R 2  is —(CH 2 ) 4-5 —CH 3 .  
     
     
         14 . The method according to  claim 10  wherein the method is used to prepare a compound selected from the group consisting of: 
 2-n-propyl-4-pentynoic acid  
 2-n-prop-1 1 -enyl-4-pentynoic acid  
 2-n-prop-2 1 -enyl-4-pentynoic acid  
 2-i-propyl-4-pentynoic acid  
 2-i-propenyl-4-pentynoic acid  
 2-n-butyl-4-pentynoic acid  
 2-n-but-1 1 -enyl-4-pentynoic acid  
 2-n-but-2 1 -enyl-4-pentynoic acid  
 2-n-but-3 1 -enyl-4-pentynoic acid  
 2-(1 1 -methylbutyl)-4-pentynoic acid  
 2-(1 1 -methylprop-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylprop-2 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpropyl)-4-pentynoic acid  
 2-(2 1 -methylprop-1 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylprop-2 1 -enyl)-4-pentynoic acid  
 2-tert.-butyl-4-pentynoic acid  
 2-n-pentyl-4-pentynoic acid  
 2-(1 1 -methylbutyl)-4-pentynoic acid  
 2-(2 1 -methylbutyl)-4-pentynoic acid  
 2-(3 1 -methylbutyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylpropyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylpropyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylpropyl)-4-pentynoic acid  
 2-n-hexyl-4-pentynoic acid  
 2-n-hex-1 1 -enyl-4-pentynoic acid  
 2-n-hex-2 1 -enyl-4-pentynoic acid  
 2-n-hex-3 1 -enyl-4-pentynoic acid  
 2-n-hex-4 1 -enyl-4-pentynoic acid  
 2-n-hex-5 1 -enyl-4-pentynoic acid  
 2-(1 1 -methylpentyl)-4-pentynoic acid  
 2-(1 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpentyl)-4-pentynoic acid  
 2-(2 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpentyl)-4-pentynoic acid  
 2-(3 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpentyl)-4-pentynoic acid  
 2-(4 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(3 1 ,3 1 -dimethylbutyl)-4-pentynoic acid  
 2-(3 1 ,3 1 -dimethylbut-1 1 -enyl)-4--pentynoic acid  
 2-(1 1 ,1 1 ,2 1 -trimethylpropyl)-4-pentynoic acid  
 2-(1 1 ,1 1 ,2 1 -trimethylprop-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,2 1 -trimethylpropyl)-4-pentynoic acid  
 2-n-heptyl-4-pentynoic acid  
 2-(1 1 -methylhexyl)-4-pentynoic acid  
 2-(2 1 -methylhexyl)-4-pentynoic acid  
 2-(3 1 -methylhexyl)-4-pentynoic acid  
 2-(4 1 -methylhexyl)-4-pentynoic acid  
 2-(5 1 -methylhexyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylpentyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylpentyl)-4-pentynoic acid  
 2-(2 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(3 1 ,3 1 -dimethylpentyl)-4-pentynoic acid  
 2-(3 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(4 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,1 1 ,2 1 -trimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,1 1 ,3 1 -trimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,3 1 -trimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,2 1 ,3 1 -trimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,3 1 ,3 1 -trimethylbutyl)-4-pentynoic acid.  
 
     
     
         15 . The method according to  claim 10  wherein the method is used to prepare at least one compound selected from the group consisting of 2-n-butyl-4-pentynoic acid; 2-n-pentyl-4-pentynoic acid and 2-n-hexyl-4-pentynoic acid.  
     
     
         16 . A method of promoting neuronal function comprising providing to neuronal cells a neurotrophic amount of a compound of formula (II)  
       
         
           
           
               
               
           
         
       
       wherein R 3  and R 4  are independently of each other saturated or unsaturated, branched, or unbranched, aliphatic C 1-30  hydrocarbons, optionally possessing at least one double or triple bond; and M is hydrogen or a metal atom.  
     
     
         17 . The method according to  claim 16  where R 3  and R 4  are unbranched and R 3  is a C 2-3  alkyl.  
     
     
         18 . The method according to  claim 17  wherein R 3 ═R 4  which are selected from —CH 2 -CH 3  and —(CH 2 ) 2 —CH 3 .  
     
     
         19 . The method according to  claim 17  wherein R 3  is —CH 2 —C≡—CH or —CH 2 —CH═CH 2 , and R 4  is a C 2 -C 10  alkyl.  
     
     
         20 . The method according to  claim 19  wherein R 3  is —CH 2 —C≡CH and R 4  is —C 3 -C 6  alkyl.  
     
     
         21 . The method according to  claim 20  wherein R 4  is —(CH 2 ) 5 —CH 3  or —(CH 2 ) 4 —CH 3 .  
     
     
         22 . The method according to  claim 16  wherein the compound provided to neuronal cells is selected from the group consisting of: 
 2-n-propylpentanoic acid  
 2-n-propyl-4-pentenoic acid  
 2-n-propyl-4-pentynoic acid  
 2-n-prop-1 1 -enyl-4-pentynoic acid  
 2-n-prop-2 1 -enyl-4-pentynoic acid  
 2-n-propylhexanoic acid  
 2-i-propyl-4-pentynoic acid  
 2-i-propenyl-4-pentynoic acid  
 2-n-butyl-4-pentynoic acid  
 2-n-butylhexanoic acid  
 2-n-but-1 1 -enyl-4-pentynoic acid  
 2-n-but-2 1 -enyl-4-pentynoic acid  
 2-n-but-3 1 -enyl-4-pentynoic acid  
 2-(1 1 -methylbutyl)-4-pentynoic acid  
 2-(1 1 -methylprop-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylprop-2 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpropyl)-4-pentynoic acid  
 2-(2 1 -methylprop-1 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylprop-2 1 -enyl)-4-pentynoic acid  
 2-tert.-butyl-4-pentynoic acid  
 2-n-pentyl-4-pentynoic acid  
 2-(1 1 -methylbutyl)-4-pentynoic acid  
 2-(2 1 -methylbutyl)-4-pentynoic acid  
 2-(3 1 -methylbutyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylpropyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylpropyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylpropyl)-4-pentynoic acid  
 2-n-hexyl-4-pentynoic acid  
 2-n-hex-1 1 -enyl-4-pentynoic acid  
 2-n-hex-2 1 -enyl-4-pentynoic acid  
 2-n-hex-3 1 -enyl-4-pentynoic acid  
 2-n-hex-4 1 -enyl-4-pentynoic acid  
 2-n-hex-5 1 -enyl-4-pentynoic acid  
 2-(1 1 -methylpentyl)-4-pentynoic acid  
 2-(1 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpentyl)-4-pentynoic acid  
 2-(2 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpentyl)-4-pentynoic acid  
 2-(3 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpentyl)-4-pentynoic acid  
 2-(4 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(3 1 ,3 1 -dimethylbutyl)-4-pentynoic acid  
 2-(3 1 ,3 1 -dimethylbut-1 1 -enyl)-4--pentynoic acid  
 2-(1 1 ,1 1 ,2 1 -trimethylpropyl)-4-pentynoic acid  
 2-(1 1 ,1 1 ,2 1 -trimethylprop-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,2 1 -trimethylpropyl)-4-pentynoic acid  
 2-n-heptyl-4-pentynoic acid  
 2-(1 1 -methylhexyl)-4-pentynoic acid  
 2-(2 1 -methylhexyl)-4-pentynoic acid  
 2-(3 1 -methylhexyl)-4-pentynoic acid  
 2-(4 1 -methylhexyl)-4-pentynoic acid  
 2-(5 1 -methylhexyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylpentyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylpentyl)-4-pentynoic acid  
 2-(2 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(3 1 ,3 1 -dimethylpentyl)-4-pentynoic acid  
 2-(3 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(4 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,1 1 ,2 1 -trimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,1 1 ,3 1 -trimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,3 1 -trimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,2 1 ,3 1 -trimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,3 1 ,3 1 -trimethylbutyl)-4-pentynoic acid.  
 
     
     
         23 . The method according to  claim 22  wherein the compound provided to neuronal cells is selected from the group consisting of 2-n-butyl-4-pentynoic acid; 2-n-pentyl-4-pentynoic acid and 2-n-hexyl-4-pentynoic acid.  
     
     
         24 . The method according to  claim 16  wherein the compound of formula (II) is administered to an individual for the prevention or treatment of a neurodegenerative disorder.  
     
     
         25 . The method according to  claim 24  wherein the neurodegenerative disorder is selected from the group consisting of Alzheimers disease, Parkinson&#39;s disease, ALS, Huntington&#39;s disease, stroke, diabetic neuropathy and trauma.  
     
     
         26 . The method according to  claim 25  wherein R 3  is —CH 2 —CH≡CH and R 4  is —(CH 2 ) 1-9 —CH 3 .  
     
     
         27 . The method according to  claim 26  wherein R 4  is —(CH 2 ) 3-5 —CH 3 .  
     
     
         28 . The method according to  claim 27  wherein the neurodegenerative disorder is Alzheimer disease.  
     
     
         29 . A pharmaceutical composition for promotoing neuronal function comprising a therapeutically effective amount of at least one compound useful for promoting neuronal function according to any one of  claims 16  to  23  and a pharmaceutically acceptable carrier.  
     
     
         30 . A method of inhibiting cell mitosis comprising administering to proliferating cells an anti-mitotic effective amount of a compound of formula (II)  
       
         
           
           
               
               
           
         
       
       wherein R 3  and R 4  are independently of each other saturated or unsaturated, branched, or unbranched, aliphatic C 1-30  hydrocarbons, optionally possessing at least one double or triple bond; M is hydrogen or a metal; with the proviso that formula II is not valproate.  
     
     
         31 . The method according to  claim 30  wherein R 3  is —CH 2 —CH≡CH and R 4  is —(CH 2 ) 1-9 —CH 3 .  
     
     
         32 . The method according to  claim 31  wherein R 4  is —(CH 2 ) 3-5 —CH 3 .  
     
     
         33 . The method according to  claim 30  wherein the compound administered to proliferating cells is selected from the group consisting of: 
 2-n-propyl-pentanoic acid  
 2-n-propyl-4-pentenoic acid  
 2-n-propyl-4-pentynoic acid  
 2-n-prop-1 1 -enyl-4-pentynoic acid  
 2-n-prop-2 1 -enyl-4-pentynoic acid  
 2-n-propylhexanoic acid  
 2-i-propyl-4-pentynoic acid  
 2-i-propenyl-4-pentynoic acid  
 2-n-butyl-4-pentynoic acid  
 2-n-butylhexanoic acid  
 2-n-but-1 1 -enyl-4-pentynoic acid  
 2-n-but-2 1 -enyl-4-pentynoic acid  
 2-n-but-3 1 -enyl-4-pentynoic acid  
 2-(1 1 -methylbutyl)-4-pentynoic acid  
 2-(1 1 -methylprop-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylprop-2 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpropyl)-4-pentynoic acid  
 2-(2 1 -methylprop-1 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylprop-2 1 -enyl)-4-pentynoic acid  
 2-tert.-butyl-4-pentynoic acid  
 2-n-pentyl-4-pentynoic acid  
 2-(1 1 -methylbutyl)-4-pentynoic acid  
 2-(2 1 -methylbutyl)-4-pentynoic acid  
 2-(3 1 -methylbutyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylpropyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylpropyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylpropyl)-4-pentynoic acid  
 2-n-hexyl-4-pentynoic acid  
 2-n-hex-1 1 -enyl-4-pentynoic acid  
 2-n-hex-2 1 -enyl-4-pentynoic acid  
 2-n-hex-3 1 -enyl-4-pentynoic acid  
 2-n-hex-4 1 -enyl-4-pentynoic acid  
 2-n-hex-5 1 -enyl-4-pentynoic acid  
 2-(1 1 -methylpentyl)-4-pentynoic acid  
 2-(1 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(1 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpentyl)-4-pentynoic acid  
 2-(2 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(2 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpentyl)-4-pentynoic acid  
 2-(3 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(3 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpentyl)-4-pentynoic acid  
 2-(4 1 -methylpent-1 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpent-2 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpent-3 1 -enyl)-4-pentynoic acid  
 2-(4 1 -methylpent-4 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbut-1 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbut-2 1 -enyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylbut-3 1 -enyl)-4-pentynoic acid  
 2-(3 1 ,3 1 -dimethylbutyl)-4-pentynoic acid  
 2-(3 1 ,3 1 -dimethylbut-1 1 -enyl)-4--pentynoic acid  
 2-(1 1 ,1 1 ,2 1 -trimethylpropyl)-4-pentynoic acid  
 2-(1 1 ,1 1 ,2 1 -trimethylprop-2 1 -enyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,2 1 -trimethylpropyl)-4-pentynoic acid  
 2-n-heptyl-4-pentynoic acid  
 2-(1 1 -methylhexyl)-4-pentynoic acid  
 2-(2 1 -methylhexyl)-4-pentynoic acid  
 2-(3 1 -methylhexyl)-4-pentynoic acid  
 2-(4 1 -methylhexyl)-4-pentynoic acid  
 2-(5 1 -methylhexyl)-4-pentynoic acid  
 2-(1 1 ,1 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,2 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,3 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(2 1 ,2 1 -dimethylpentyl)-4-pentynoic acid  
 2-(2 1 ,3 1 -dimethylpentyl)-4-pentynoic acid  
 2-(2 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(3 1 ,3 1 -dimethylpentyl)-4-pentynoic acid  
 2-(3 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(4 1 ,4 1 -dimethylpentyl)-4-pentynoic acid  
 2-(1 1 ,1 1 ,2 1 -trimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,1 1 ,3 1 -trimethylbutyl)-4-pentynoic acid  
 2-(1 1 ,2 1 ,3 1 -trimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,2 1 ,3 1 -trimethylbutyl)-4-pentynoic acid  
 2-(2 1 ,3 1 ,3 1 -trimethylbutyl)-4-pentynoic acid.  
 
     
     
         34 . The method according to  claim 33  wherein the compound administered is selected from the group consisting of 2-n-butyl-4-pentynoic acid; 2-n-pentyl-4-pentynoic acid and 2-n-hexyl-4-pentynoic acid.  
     
     
         35 . The method according to  claim 30  used to treat an individual with a neoplastic disease comprising administering an antimitotic amount of the compound according to  claim 2 .  
     
     
         36 . The method according to  claim 30  wherein the mitotic cells are derived from the neural crest.  
     
     
         37 . The method according to  claim 30  wherein the mitotic cells are present in the central nervous system.
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