IP Library › Granted Patent US 9,994,564

Granted Patent B2

US 9,994,564 · App. 15/254,517 · Granted Jun 12, 2018

Myosin II ATPase inhibitor compounds

Inventors: Michael E. DiSanto (Burlington, NJ); Karl P. Dresdner, Jr. (Newtown, PA)

C07D471/04

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Quick Facts

Patent No.: US 9,994,564
App. No.: 15/254,517
Granted: Jun 12, 2018
Kind: B2

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Abstract

The present invention relates to Myosin II ATPase inhibitor compounds, including substituted 3a-hydroxy-1,2,3,3a-tetrahydro-4H-pyrrolo [2,3b] quinolin-4-one compounds which are blebbistatin derivatives.

Claims (195)

1. A Myosin II ATPase inhibitor compound of Formula (IV) or a pharmaceutically-acceptable salt, a racemic mixture, or an enantiomer thereof, comprising:

wherein an X is selected from the group consisting of fluoro, chloro, bromo, iodo, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynl, thio, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkoxy, (C 1-6 )alkylamino(C 1-6 )alkyl, (C 1-6 )alkylaminoketo, acetamido, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, benzyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the X is optionally substituted at a carbon atom with a substituent B selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, methoxy, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 4-10 )aryl, (C 1-6 )alkylamino(C 1-6 )alkyl, benzyl, (C 1-6 )alkylaminoketo, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, acetamido, and (C 4-8 )heteroaryl, and

wherein the X is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with a substituent E selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, benzyl, (C 4-8 )heterocyclic, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heteroaryl, glycinyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, prolinyl, methionyl, phenylalanyl, tyrosinyl, tryptophanyl, threonyl, cystinyl, asparginyl, lysinyl, histidinyl, arginyl, aspartyl, and glutamyl;

wherein a Y is selected from the group consisting of hydrogen, hydroxy, fluoro, chloro, bromo, cyano, carboxy, (C 1-6 )alkyl, (C 1-6 )alkoxy, thio, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, iodo, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, carbamyl, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkylamino(C 1-6 )alkyl, acetamido, (C 1-6 )alkylaminoketo, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, nitro, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )aryl, benzyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the Y is optionally substituted at a carbon atom with a substituent G selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, (C 1-6 )alkyl, (C 1-6 ) alkoxy, thio, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, amino, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , C 1-6 )alkylamino, carb(C 1-6 )alkoxy, (C 1-6 )alkylamino(C 1-6 )alkyl, (C 1-6 )alkylaminoketo, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, acetamido, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, benzyl, and (C 4-8 )heteroaryl, and

wherein the Y is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with a substituent J selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, (C 4-8 )heteroaryl, benzyl, glycinyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, prolinyl, methionyl, phenylalanyl, tyrosinyl, tryptophanyl, threonyl, cystinyl, asparginyl, lysinyl, histidinyl, arginyl, aspartyl, and glutamyl;

wherein an S1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynl, thio, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkoxy, (C 1-6 )alkylamino(C 1-6 )alkyl, (C 1-6 )alkylaminoketo, acetamido, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, benzyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the S1 is optionally substituted at a carbon atom with a substituent H selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, methoxy, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 4-10 )aryl, (C 1-6 )alkylamino(C 1-6 )alkyl, benzyl, (C 1-6 )alkylaminoketo, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, acetamido, and (C 4-8 )heteroaryl, and

wherein the S1 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with a substituent K selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, benzyl, (C 4-8 )heterocyclic, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heteroaryl, glycinyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, prolinyl, methionyl, phenylalanyl, tyrosinyl, tryptophanyl, threonyl, cystinyl, asparginyl, lysinyl, histidinyl, arginyl, aspartyl, and glutamyl;

wherein an R1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynl, thio, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkoxy, (C 1-6 )alkylamino(C 1-6 )alkyl, (C 1-6 )alkylaminoketo, acetamido, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, benzyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R1 is optionally substituted at a carbon atom with a substituent D1 selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, methoxy, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 4-10 )aryl, (C 1-6 )alkylamino(C 1-6 )alkyl, benzyl, (C 1-6 )alkylaminoketo, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, acetamido, and (C 4-8 )heteroaryl, and

wherein the R1 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with a substituent F1 selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, benzyl, (C 4-8 )heterocyclic, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heteroaryl, glycinyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, prolinyl, methionyl, phenylalanyl, tyrosinyl, tryptophanyl, threonyl, cystinyl, asparginyl, lysinyl, histidinyl, arginyl, aspartyl, and glutamyl;

wherein an R2 is selected from the group consisting of hydrogen, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynl, thio, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkoxy, (C 1-6 )alkylamino(C 1-6 )alkyl, (C 1-6 )alkylaminoketo, acetamido, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, benzyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, napthyl-(C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R2 is optionally substituted at a carbon atom with a substituent D2 selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, methoxy, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 4-10 )aryl, (C 1-6 )alkylamino(C 1-6 )alkyl, benzyl, (C 1-6 )alkylaminoketo, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, acetamido, and (C 4-8 )heteroaryl, and

wherein the R2 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with a substituent F2 selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, benzyl, (C 4-8 )heterocyclic, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heteroaryl, glycinyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, prolinyl, methionyl, phenylalanyl, tyrosinyl, tryptophanyl, threonyl, cystinyl, asparginyl, lysinyl, histidinyl, arginyl, aspartyl, and glutamyl;

wherein an R3 is selected from the group consisting of carboxy, (C 2-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynl, thio, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkylamino(C 1-6 )alkyl, (C 1-6 )alkylaminoketo, acetamido, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, benzyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R3 is optionally substituted at a carbon atom with a substituent D3 selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, methoxy, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 4-10 )aryl, (C 1-6 )alkylamino(C 1-6 )alkyl, benzyl, (C 1-6 )alkylaminoketo, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkyl-O—C(═O)—(C 1-6 )alkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, acetamido, and (C 4-8 )heteroaryl, and

wherein the R3 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with a substituent F3 selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, benzyl, (C 4-8 )heterocyclic, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heteroaryl, glycinyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, prolinyl, methionyl, phenylalanyl, tyrosinyl, tryptophanyl, threonyl, cystinyl, asparginyl, lysinyl, histidinyl, arginyl, aspartyl, and glutamyl;

wherein an R4 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynl, thio, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkoxy, (C 1-6 )alkylamino(C 1-6 )alkyl, (C 1-6 )alkylaminoketo, acetamido, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, benzyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R4 is optionally substituted at a carbon atom with a substituent D4 selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, methoxy, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 4-10 )aryl, (C 1-6 )alkylamino(C 1-6 )alkyl, benzyl, (C 1-6 )alkylaminoketo, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, acetamido, and (C 4-8 )heteroaryl, and

wherein the R4 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with a substituent F4 selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, benzyl, (C 4-8 )heterocyclic, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heteroaryl, glycinyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, prolinyl, methionyl, phenylalanyl, tyrosinyl, tryptophanyl, threonyl, cystinyl, asparginyl, lysinyl, histidinyl, arginyl, aspartyl, and glutamyl; and

wherein an R5 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynl, thio, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkoxy, (C 1-6 )alkylamino(C 1-6 )alkyl, (C 1-6 )alkylaminoketo, acetamido, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, benzyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R5 is optionally substituted at a carbon atom with a substituent D5 selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, (C 1-6 )alkyl, (C 2-6 )alkenyl, methoxy, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 4-10 )aryl, (C 1-6 )alkylamino(C 1-6 )alkyl, benzyl, (C 1-6 )alkylaminoketo, carb(C 1-6 )alkoxy, (C 1-6 )alkyl-C(═O)—O—(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkyl-O—C(═O)-(C 1-6 )alkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, acetamido, and (C 4-8 )heteroaryl,

wherein the R5 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with a substituent F5 selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, benzyl, (C 4-8 )heterocyclic, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heteroaryl, glycinyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, prolinyl, methionyl, phenylalanyl, tyrosinyl, tryptophanyl, threonyl, cystinyl, asparginyl, lysinyl, histidinyl, arginyl, aspartyl, and glutamyl, and

wherein when substituents R1, R2, R4, and R5 are hydrogen and substituent R3 is (C 4-12 )aryl, then the substituent (C 4-10 )aryl is other than phenyl.

2. The compound according to claim 1 , wherein the X is selected from the group consisting of (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynl, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino amino(C 1-6 )alkyl, (C 1-6 )alkylamino, (C 1-6 )alkoxy, (C 1-6 )alkylamino(C 1-6 )alkyl, carb(C 1-6 )alkoxy, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, benzyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the X is optionally substituted at a carbon atom with the substituent B selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, acetyl, (C 1-6 )alkyl, (C 2-6 )alkenyl, methoxy, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, (C 1-6 )alkylamino, (C 4-10 )aryl, (C 1-6 )alkylamino(C 1-6 )alkyl, benzyl, (C 1-6 )alkylaminoketo, carb(C 1-6 )alkoxy, (C 1-6 )alkylcarboxy, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, acetamido, and (C 4-8 )heteroaryl, and

wherein the X is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent E selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, phenyl, glycinyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, prolinyl, methionyl, phenylalanyl, tyrosinyl, threonyl, cystinyl, lysinyl, aspartyl, and glutamyl;

wherein the Y is selected from the group consisting of hydrogen, hydroxy, fluoro, chloro, bromo, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, amino, (C 1-6 )alkoxy, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, nitro, (C 3-7 )cycloalkyl, (C 4-10 )aryl, benzyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the Y is optionally substituted at a carbon atom with the substituent G selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, methoxy, (C 1-6 ) alkoxy, amino, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-8 )heterocyclic, benzyl, and (C 4-8 )heteroaryl, and

wherein the Y is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent J selected from the group consisting of (C 1-6 )alkyl, glycinyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, prolinyl, methionyl, phenylalanyl, tyrosinyl, tryptophanyl, threonyl, cystinyl, asparginyl, lysinyl, histidinyl, arginyl, aspartyl, and glutamyl;

wherein the S1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxy, carbethoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, acetyl, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynl, (C 1-6 )alkoxy, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, benzyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the S1 is optionally substituted at a carbon atom with the substituent H selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, amino, (C 4-8 )heterocyclic, acetamido, and (C 4-8 )heteroaryl, and

wherein the S1 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent K selected from the group consisting of (C 1-6 )alkyl, alanyl, methionyl, phenylalanyl, tyrosinyl, threonyl, cystinyl, lysinyl, aspartyl, and glutamyl;

wherein the R1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, amino(C 1-6 )alkyl, (C 1-6 )alkylamino, (C 1-6 )alkoxy, and (C 1-6 )alkylamino(C 1-6 )alkyl,

wherein the R1 is optionally substituted at a carbon atom with the substituent D1 selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, (C 2-6 )alkenyl, methoxy, chloromethyl, carbamyl, fluoromethyl, and trifluoromethyl, and

wherein the R1 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F1 selected from the group consisting of (C 1-6 )alkyl, cyclopropyl, and (C 1-6 )haloalkyl;

wherein the R2 is selected from the group consisting of hydrogen, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, (C 2-6 )alkenyl, (C 2-6 )alkynl, thio, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, (C 1-6 )alkoxy, (C 1-6 )alkylcarboxy, phenyl-,benzyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R2 is optionally substituted at a carbon atom with the substituent D2 selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, methoxy, chloromethyl, carbamyl, fluoromethyl, trifluoromethyl, and (C 4-8 )heteroaryl, and

wherein the R2 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F2 selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, phenyl, serinyl, methionyl, phenylalanyl, tyrosinyl, lysinyl, aspartyl, and glutamyl;

wherein the R3 is selected from the group consisting of carboxy, carbethoxy, acetyl, (C 2-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 1-6 )alkanoyl, acetonyl, benzyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R3 is optionally substituted at a carbon atom with the substituent D3 selected from the group consisting of hydroxy, chloro, bromo, iodo, nitro, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, (C 2-6 )alkenyl, methoxy, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, amino, acetonyl, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 4-10 )aryl, (C 1-6 )alkylamino(C 1-6 )alkyl, benzyl, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl, and

wherein the R3 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F3 selected from the group consisting of (C 1-6 )alkyl, (C 1-6 )haloalkyl, (C 3-7 )cycloalkyl, phenyl, serinyl, phenylalanyl, tyrosinyl, lysinyl, aspartyl, and glutamyl;

wherein the R4 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, methylamino, amino, hydroxyalkyl, benzyl, (C 1-6 )alkyl-keto-(C 1-6 )alkyl, (C 1-6 )alkoxy(C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R4 is optionally substituted at a carbon atom with the substituent D4 selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, (C 4-8 )heterocyclic, acetamido, and (C 4-8 )heteroaryl, and

wherein the R4 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F4 selected from the group consisting of (C 1-6 )alkyl, cyclopropyl, (C 1-6 )haloalkyl, phenylalanyl, tyrosinyl, lysinyl, aspartyl, and glutamyl; and

wherein the R5 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxy, acetyl, (C 1-6 )alkyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R5 is optionally substituted at a carbon atom with the substituent D5 selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, and carboxy, and

wherein when substituents R1, R2, R4, and R5 are hydrogen and substituent R3 is (C 4-12 )aryl, then the substituent (C 4-10 )aryl is other than phenyl.

3. The compound according to claim 1 , wherein the X is selected from the group consisting of (C 1-6 )alkyl, amino, amino(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the X is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent E selected from the group consisting of (C 1-6 )alkyl, alanyl, serinyl, valinyl, leucinyl, isoleucinyl, lysinyl, aspartyl, and glutamyl;

wherein the Y is selected from the group consisting of hydrogen, hydroxy, fluoro, chloro, bromo, cyano, amino, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the Y is optionally substituted at a carbon atom with the substituent G selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, benzyl, and (C 4-8 )heteroaryl, and

wherein the Y is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent J selected from the group consisting of methyl(C 1-6 )alkyl, phenylalanyl, tyrosinyl, lysinyl, aspartyl, and glutamyl;

wherein the R1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, (C 1-6 )alkyl, and amino,

wherein the R1 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F1 selected from the group consisting of methyl, (C 1-6 )alkyl, and cyclopropyl;

wherein the R2 is selected from the group consisting of hydrogen, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, and (C 4-8 )heteroaryl, and

wherein the R2 is optionally substituted at a carbon atom with the substituent D2 selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, and carboxy;

wherein an R3 is selected from the group consisting of carboxy, carbethoxy, acetyl, (C 2-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, methylamino, aminomethyl, acetonyl, benzyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R3 is optionally substituted at a carbon atom with the substituent D3 selected from the group consisting of methyl, hydroxy, chloro, bromo, iodo, nitro, cyano, carboxy, methoxy, amino, (C 3-7 )cycloalkyl, (C 4-7 )cycloalkenyl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl, and

wherein the R3 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F3 selected from the group consisting of phenylalanyl, tyrosinyl, lysinyl, aspartyl, and glutamyl;

wherein the R4 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxy, acetyl, (C 1-6 )alkyl, (C 1-6 )alkylthio, thio(C 1-6 )alkyl, carbamyl, amino, hydroxyalkyl, benzyl, (C 4-10 )aryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R4 is optionally substituted at a carbon atom with the substituent D4 selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, and cyano, and

wherein the R5 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, and iodo,

wherein the R5 is optionally substituted at a carbon atom with the substituent D5 selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, and nitro, and

wherein when substituents R1, R2, R4, and R5 are hydrogen and when substituent R3 is (C 4-12 )aryl, then the substituent (C 4-10 )aryl is other than phenyl.

4. The compound according to claim 1 , wherein the X is selected from the group consisting of (C 1-6 )alkyl, amino, amino(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 1-6 )alkylcarboxy, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the Y is selected from the group consisting of hydrogen, hydroxy, fluoro, chloro, bromo, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the Y is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent J selected from the group consisting of (C 1-6 )alkyl, phenylalanyl, tyrosinyl, lysinyl, aspartyl, and glutamyl;

wherein the R1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, (C 1-6 )alkyl, and amino,

wherein the R1 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F1 selected from the group consisting of (C 1-6 )alkyl, and cyclopropyl;

wherein the R2 is selected from the group consisting of hydrogen, cyano, carboxy, carbethoxy, acetyl, (C 1-6 )alkyl, and (C 4-8 )heteroaryl, and

wherein the R2 is optionally substituted at a carbon atom with the substituent D2 selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, and carboxy;

wherein the R3 is selected from the group consisting of carboxy, carbethoxy, acetyl, (C 2-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, methylamino, aminomethyl, acetonyl, benzyl, (C 3-7 )cycloalkyl, napthyl-(C 4-10 )aryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R4 is optionally substituted at a carbon atom with the substituent D4 selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, and cyano, and

wherein the R5 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, and iodo, and

wherein when substituents R1, R2, R4, and R5 are hydrogen and substituent R3 is (C 4-12 )aryl, then the substituent (C 4-10 )aryl is other than phenyl.

5. The compound according to claim 1 , wherein the X is selected from the group consisting of (C 1-6 )alkyl, amino, amino(C 1-6 )alkyl, (C 1-6 )hydroxyalkyl, (C 3-7 )cycloalkyl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the X is optionally substituted at a carbon atom with the substituent B selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, carboxy, amino, phenyl, and (C 4-8 )heterocyclic, and

wherein the Y is selected from the group consisting of hydrogen, hydroxy, fluoro, chloro, bromo, cyano, carboxy, carbethoxy, acetyl, and (C 1-6 )alkyl,

wherein the Y is optionally substituted at a carbon atom with the substituent G selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, and nitro, and

wherein the S1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxy, carbethoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, acetyl, (C 1-6 )alkyl, acetonyl, benzyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the S1 is optionally substituted at a carbon atom with the substituent H selected from the group consisting of methyl, amino, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl, and

wherein the R1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, (C 1-6 )alkyl, and amino,

wherein the R1 is optionally substituted at a carbon atom with the substituent D1 selected from the group consisting of hydroxy, fluoro, chloro, bromo, and trifluoromethyl, and

wherein the R1 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F1 selected from the group consisting of (C 1-6 )alkyl;

wherein the R2 is selected from the group consisting of hydrogen, cyano, carboxy, (C 1-6 )alkyl, and (C 4-8 )heteroaryl, and

wherein the R2 is optionally substituted at a carbon atom with the substituent D2 selected from the group consisting of methyl, hydroxy, fluoro, chloro, and bromo;

wherein the R3 is selected from the group consisting of carboxy, carbethoxy, acetyl, (C 2-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, (C 4-10 )aryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R4 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, cyano, carboxyphenyl, benzyl, (C 4-10 )aryl, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R4 is optionally substituted at a carbon atom with the substituent D4 selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, and cyano, and

wherein the R4 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F4 selected from the group consisting of (C 1-6 )alkyl, phenylalanyl, tyrosinyl, lysinyl, aspartyl, and glutamyl; and

wherein the R5 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, and iodo, and

wherein when substituents R1, R2, R4, and R5 are hydrogen and substituent R3 is (C 4-12 )aryl, then the substituent (C 4-10 )aryl is other than phenyl.

6. The compound according to claim 1 , wherein the X is selected from the group consisting of (C 1-6 )alkyl, amino, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the X is optionally substituted at a carbon atom with the substituent B selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, iodo, nitro, cyano, and carboxy, and

wherein the X is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent E selected from the group consisting of (C 1-6 )alkyl, lysinyl, aspartyl, and glutamyl;

wherein the Y is selected from the group consisting of hydrogen, fluoro, bromo, cyano, carboxy, and (C 1-6 )alkyl,

wherein the Y is optionally substituted at a carbon atom with the substituent G selected from the group consisting of methyl, fluoro, bromo, and nitro, and

wherein the S1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, carboxy, carbethoxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, acetyl, (C 1-6 )alkyl, benzyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, (C 4-10 )haloaryl, and (C 4-8 )heterocyclic,

wherein the S1 is optionally substituted at a carbon atom with the substituent H selected from the group consisting of methyl, amino, and (C 4-8 )heterocyclic, and

wherein the R1 is selected from the group consisting of hydrogen, fluoro, bromo, (C 1-6 )alkyl, and amino,

wherein the R1 is optionally substituted at a carbon atom with the substituent D1 selected from the group consisting of hydroxy, fluoro, and bromo, and

wherein the R1 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F1 selected from the group consisting of (C 1-6 )alkyl;

wherein the R2 is selected from the group consisting of hydrogen, carboxy, (C 1-6 )alkyl, and

wherein the R2 is optionally substituted at a carbon atom with the substituent D2 selected from the group consisting of fluoro, chloro, and bromo;

wherein the R3 is selected from the group consisting of carboxy, (C 2-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, (C 4-10 )aryl, and (C 4-8 )heterocyclic,

wherein the R3 is optionally substituted at a carbon atom with the substituent D3 selected from the group consisting of methyl, chloro, bromo, iodo, nitro, methoxy, amino, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl, and

wherein the R3 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F3 selected from the group consisting of phenylalanyl, tyrosinyl, and lysinyl;

wherein the R4 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl,

wherein the R4 is optionally substituted at a carbon atom with the substituent D4 selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, and iodo,

wherein the R5 is selected from the group consisting of hydrogen, fluoro, and bromo,

wherein the R5 is optionally substituted at a carbon atom with the substituent D5 selected from the group consisting of hydroxy, fluoro, bromo, and nitro, and

wherein when substituents R1, R2, R4, and R5 are hydrogen and substituent R3 is (C 4-12 )aryl, then the substituent (C 4-10 )aryl is other than phenyl.

7. The compound according to claim 1 , wherein the X is selected from the group consisting of (CI-6)alkyl, amino, and (C 4-8 )heteroaryl,

wherein the X is optionally substituted at a carbon atom with the substituent B selected from the group consisting of methyl, hydroxy, fluoro, chloro, bromo, and nitro, and

wherein the X is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent E selected from the group consisting of (C 1-6 )alkyl, lysinyl, and aspartyl;

wherein the Y is selected from the group consisting of fluoro, bromo, and (C 1-6 )alkyl, and

wherein the Y is optionally substituted at a carbon atom with the substituent G selected from the group consisting of methyl, fluoro, bromo, and nitro;

wherein the S1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, iodo, carboxy, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkyl, benzyl, (C 3-7 )cycloalkyl, (C 4-10 )aryl, and (C 4-8 )heterocyclic,

wherein the S1 is optionally substituted at a carbon atom with the substituent H selected from the group consisting of methyl, amino, and (C 4-8 )heterocyclic, and

wherein the R1 is selected from the group consisting of hydrogen, fluoro, (C 1-6 )alkyl, and

wherein the R1 is optionally substituted at a carbon atom with the substituent D1 selected from the group consisting of fluoro, and bromo;

wherein the R2 is selected from the group consisting of hydrogen, and (C 1-6 )alkyl, and

wherein the R2 is optionally substituted at a carbon atom with the substituent D2 selected from the group consisting of fluoro, and bromo;

wherein the R3 is selected from the group consisting of carboxy, (C 2-6 )alkyl, (C 1-6 )haloalkyl, (C 1-6 )haloalkoxy, (C 4-10 )aryl, and (C 4-8 )heterocyclic,

wherein the R3 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F3 selected from the group consisting of phenylalanyl and tyrosinyl;

wherein the R4 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, and (C 4-8 )heterocyclic,

wherein the R4 is optionally substituted at a carbon atom with the substituent D4 selected from the group consisting of fluoro, chloro, bromo, and iodo, and

wherein the R4 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F4 selected from the group consisting of phenylalanyl, tyrosinyl, and lysinyl; and

wherein the R5 is selected from the group consisting of hydrogen, and

wherein when substituents R1, R2, R4, and R5 are hydrogen and substituent R3 is (C 4-12 )aryl, then the substituent (C 4-10 )aryl is other than phenyl.

8. The compound according to claim 1 , wherein the X is selected from the group consisting of (C 1-6 )alkyl, and

wherein the X is optionally substituted at a carbon atom with the substituent B selected from the group consisting of fluoro, bromo, and nitro;

wherein the Y is selected from the group consisting of bromo and (C 1-6 )alkyl, and

wherein the Y is optionally substituted at a carbon atom with the substituent G selected from the group consisting of methyl, and nitro;

wherein the S1 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkyl, phenyl, (C 3-7 )cycloalkyl, and (C 4-8 )heterocyclic;

wherein the R1 is selected from the group consisting of hydrogen and (C 1-6 )alkyl;

wherein the R2 is selected from the group consisting of hydrogen and (C 1-6 )alkyl, and

wherein the R2 is optionally substituted at a carbon atom with the substituent D2 selected from the group consisting of fluoro, and bromo;

wherein the R3 is selected from the group consisting of amino, carboxy, (C 2-6 )alkyl, (C 4-10 )aryl, and (C 4-8 )heterocyclic,

wherein the R3 is optionally substituted at a carbon atom with the substituent D3 selected from the group consisting of chloro, bromo, nitro, methoxy, amino, (C 4-8 )heterocyclic, and (C 4-8 )heteroaryl, and

wherein the R3 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F3 selected from the group consisting of phenylalanyl and tyrosinyl;

wherein the R4 is selected from the group consisting of hydrogen, chloro, bromo, and (C 4-8 )heterocyclic; and

wherein the R5 is selected from the group consisting of hydrogen, and

wherein when substituents R1, R2, R4, and R5 are hydrogen and substituent R3 is (C 4-12 )aryl, then the substituent (C 4-10 )aryl is other than phenyl.

9. The compound according to claim 1 , wherein the X is selected from the group consisting of (C 1-6 )alkyl;

wherein the Y is selected from the group consisting of (C 1-6 )alkyl;

wherein the S1 is selected from the group consisting of amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkyl, and (C 4-8 )heterocyclic;

wherein the R1 is selected from the group consisting of hydrogen and (C 1-6 )alkyl;

wherein the R2 is selected from the group consisting of hydrogen and (C 1-6 )alkyl;

wherein the R3 is selected from the group consisting of carboxy, (C 2-6 )alkyl, and (C 4-8 )heterocyclic,

wherein the R3 is optionally substituted at a carbon atom with the substituent D3 selected from the group consisting of chloro, bromo, nitro, methoxy, amino, and (C 4-8 )heteroaryl, and

wherein the R3 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F3 selected from the group consisting of phenylalanyl and tyrosinyl;

wherein the R4 is selected from the group consisting of bromo, and (C 4-8 )heterocyclic; and

wherein the R5 is selected from the group consisting of hydrogen.

10. The compound according to claim 1 , wherein the X is selected from the group consisting of (C 1-6 )alkyl, and

wherein the X is optionally substituted at a carbon atom with the substituent B selected from the group consisting of fluoro, and bromo;

wherein the Y is selected from the group consisting of hydrogen;

wherein the S1 is selected from the group consisting of amino, amino(C 1-6 )alkyl, amino[(C 1-6 )alkyl] 2 , (C 1-6 )alkylamino, (C 1-6 )alkyl, and (C 4-8 )heterocyclic;

wherein the R1 is selected from the group consisting of hydrogen and (C 1-6 )alkyl;

wherein the R2 is selected from the group consisting of hydrogen and (C 1-6 )alkyl;

wherein the R3 is selected from the group consisting of (C 4-8 )heterocyclic,

wherein the R3 is optionally substituted at a carbon atom with the substituent D3 selected from the group consisting of chloro, bromo, nitro, methoxy, amino, and (C 4-8 )heteroaryl, and

wherein the R3 is optionally substituted at a primary nitrogen atom or at a secondary nitrogen atom with the substituent F3 selected from the group consisting of phenylalanyl and tyrosinyl;

wherein the R4 is selected from the group consisting of hydrogen, and (C 1-6 )alkyl; and

wherein the R5 is selected from the group consisting of hydrogen.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 12, 2016

From: DISANTO, MICHAEL E., DR.; DRESDNER, KARL P., DR.

To: BLEBBICORP

Reel/Frame 039701/0319 →

Continuity (4)

Continuation In Part 14118448 · Jan 27, 2014

Continuation In Part 15209205 · Jul 13, 2016

Continuation In Part 15207718 · Jul 12, 2016

Related Publication 20170129886A1 · May 11, 2017