Indole and indoline derivatives and methods of use thereof

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Quick Facts

Patent No.: US 9,063,126
App. No.: 12/568,085
Granted: Jun 23, 2015
Kind: B2

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Abstract

The present application relates to indole and indoline derivatives of formula (I), (II), (III), (IV), (V), or (VI) wherein a, R 1 , R 2 , R 3 , R 4 , R 5 , U, V, W, X, Y, and Z are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating disease conditions using such compounds and compositions, and methods for identifying such compounds.

Claims (71)

1. A compound of formula (III), (IV), (V), or (VI):

or a pharmaceutically acceptable salt thereof, wherein

a is a single or double bond;

X is NR 6 ;

V is —(CH 2 ) p —, wherein p is 0 or 1;

Y is —(CH 2 ) p —, wherein p is 2;

Z is —(CH 2 ) q —;

q is 1, 2, or 3;

R 1 , R 2 , R 3 , and R 4 are each independently hydrogen, alkyl, alkenyl, alkynyl, halogen, cyano, —OR 1a , —SR 1a , —S(O) 2 R 2a , or haloalkyl; wherein

R 1a , at each occurrence, is independently hydrogen, alkyl, or haloalkyl;

R 2a , at each occurrence, is independently alkyl, or haloalkyl;

R 6 is —CH 2 CH 2 -pyridinyl, —CH═CH-pyridinyl, —CH 2 CH 2 -phenyl, or —CH═CH-phenyl, wherein pyridinyl and phenyl are each independently unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of alkyl, alkenyl, alkynyl, halogen, cyano, oxo, —NO 2 , —OR 1b , —OC(O)R 1b , —OC(O)N(R b )(R 3b ), —SR 1b , —S(O) 2 R 2b , —S(O) 2 N(R b )(R 3b ), —C(O)R 1b , —C(O) OR 1b , —C(O)N(R b )(R 3b ), —N(R b )(R 3b ), —N(R a )C(O)R 1b , —N(R a )C(O)N(R 1b ), —N(R a )C(O)N(R b )(R 3b ), —(CR 4b R 5b ) m —NO 2 , —(CR 4b R 5b ) m OR 1b , —(CR 4b R 5b ) m —OC(O)R 1b , —(CR 4b R 5b ) m OC(O)N(R b )(R 3b ), —(CR 4b R 5b ) m —SR 1b , —(CR 4b R 5b ) m —S(O) 2 R 2b , —(CR 4b R 5b ) m —S(O) 2 N(R b )(R 3b ), —(CR 4b R 5b ) m —C(O)R 1b , —(CR 4b R 5b ) m —C(O)OR 1b , —(CR 4b R 5b ) m —C(O)N(R b )(R 3b ), —(CR 4b R 5b ) m —N(R b )(R 3b ), —(CR 4b R 5b ) m —N(R a )C(O)R 1b , —(CR 4b R 5b ) m —N(R a )C(O)O(R 1b ), —(CR 4b R 5b ) m —N(R a )C(O)N(R b )(R 3b ), cyanoalkyl, and haloalkyl;

m, at each occurrence, is independently 1, 2, 3, 4, or 5;

R a and R b , at each occurrence, are each independently hydrogen, alkyl, or haloalkyl;

R 1b and R 3b , at each occurrence, are each independently hydrogen, alkyl, or haloalkyl;

R 2b , at each occurrence, is independently alkyl or haloalkyl;

R 4b and R 5b , at each occurrence, are each independently hydrogen, halogen, alkyl, or haloalkyl;

with the proviso that compounds of formula (IV) are excluded wherein,

a is a double bond;

V is —(CH 2 ) p —, wherein p is 0;

Y is —(CH 2 ) p —, wherein p is 2; and

Z is —(CH 2 ) q —, wherein q is 1.

2. The compound according to claim 1 of formula (III), wherein