Piperazine derivatives, compositions, and uses related thereto

1. A pharmaceutical composition comprising a compound of Formula IE,

or pharmaceutically acceptable salt thereof, wherein;

A is CR 9 ;

R 9 is hydrogen, or alkyl;

Y 3 is methoxy, ethoxy, trifluoromethoxy, isopropoxy, or alkoxy;

Y 1 , Y 2 , Y 4 and Y 5 are each, the same or different, hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl) 2 amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, or aryl;

R 3 , R 4 , and R 6 are each, the same or different, hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl) 2 amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, or aryl;

R 5 is alkylsulfonyl, alkoxycarbonyl, alkylcarbamoyl, alkanoyl, carboxy, or carbamoyl;

X 1 is hydrogen;

X 3 , X 4 , X 5 , and X 6 are each, the same or different, hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl) 2 amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, or aryl.

2. The composition of claim 1 wherein the compound is selected from the group consisting of:

1-(2-(4-(4-methoxyphenyl)piperazine-1-carbonyl)-1H-indol-5-yl)ethanone;

1-(2-(4-(4-methoxyphenyl)piperazine-1-carbonyl)-3-methyl-1H-indol-5-yl)ethanone;

(4-(4-methoxyphenyl)piperazin-1-yl)(5-(methylsulfonyl)-1H-indol-2-yl)methanone;

methyl 2-(4-(4-methoxyphenyl)piperazine-1-carbonyl)-1H-indole-5-carboxylate;

2-(4-(4-methoxyphenyl)piperazine-1-carbonyl)-N-methyl-1H-indole-5-carboxamide;

2-(4-(4-methoxyphenyl)piperazine-1-carbonyl)-1H-indole-5-carboxamide;

2-(4-(4-methoxyphenyl)piperazine-1-carbonyl)-1H-indole-5-carboxylic acid;

1-(2-(4-(4-ethoxyphenyl)piperazine-1-carbonyl)-1H-indol-5-yl)ethanone;

1-(2-(4-(3-fluoro-4-methoxyphenyl)piperazine-1-carbonyl)-1H-indol-5-yl)ethanone; and

1-(2-(4-(4-isopropoxyphenyl)piperazine-1-carbonyl)-1H-indol-5-yl)ethanone;

or salt thereof.

3. A pharmaceutical composition comprising a compound comprising Formula IIB,

or pharmaceutically acceptable salt thereof, wherein;

n is 1 or 2;

R 3 , R 4 , R 5 , and R 6 are each, the same or different, hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl) 2 amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, or aryl;

R 9 is amino, alkylamino, dialkylamino, piperidinyl, piperazinyl, or morpholinyl wherein R 9 is optionally substituted with alkyl or dialkylamino;

X 1 , X 4 , X 5 , and X 6 are each, the same or different, hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl) 2 amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, or aryl;

Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 are each, the same or different, hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl) 2 amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, or aryl.

4. A pharmaceutical composition comprising a compound selected from the group consisting of:

(3-(((2-(diethylamino)ethyl)amino)methyl)-5-fluoro-1H-indol-2-yl)(4-(4-methoxyphenyl)piperazin-1-yl)methanone;

(5-fluoro-3-(morpholinomethyl)-1H-indol-2-yl)(4-(4-methoxyphenyl)piperazin-1-yl)methanone;

(5-fluoro-3-(((1-methylpiperidin-4-yl)amino)methyl)-1H-indol-2-yl)(4-(4-methoxyphenyl)piperazin-1-yl)methanone;

(3-((4-ethylpiperazin-1-yl)methyl)-5-fluoro-1H-indol-2-yl)(4-(4-methoxyphenyl)piperazin-1-yl)methanone; and

(3-((diethylamino)methyl)-5-fluoro-1H-indol-2-yl)(4-(4-methoxyphenyl)piperazin-1-yl)methanone

or salts thereof.