Patent ID: 6656910
Filing Date: 2003-12-02
Classification: A61K,C07D,C07K

Abstract:
A compound of the formula: wherein X and Y are independently O, S or N, wherein N can be substituted with alkyl or alkenyl, which alkyl or alkenyl can be substituted with 1-3 halo atoms; or N can be substituted with a cyclic moiety selected from the group consisting of: (C5-C6)aryl, (C5-C6)arylalkyl and (C5-C6)arylalkenyl, which cyclic moiety can include 1-3 non-carbon atoms, which non-carbon atoms are N, O or S and which cyclic moiety can be substituted with one or more of the following: halo, cyano, nitro, hydroxyl, haloalkyl, amino, aminoalkyl, dialkylamino, alkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide , (C5-C12arylcarboxamide or alkylthio; R1 is an alkyl, alkenyl or alkynyl, which alkyl, alkenyl or alkynyl can be substituted with one or more of the following: halo, hydroxyl, cyano, nitro, haloalkyl, alkylamino, dialkylamino, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, (C5-C12)arylcarboxamide or â€”Oâ€”(C5-C6)aryl; or R1 is hydroxyl, amino, alkylamino, or dialkylamino; or R1 is a cyclic moiety selected from the group consisting of: cycloalkyl, alkylcycloalkyl, alkenylcycloalkyl, cycloalkenyl, alkylcycloalkenyl, alkenylcycloalkenyl, (C5-C12)aryl, (C5-C12)arylalkyl, (C5-C12)arylalkenyl, fused (C5-C12)aryl-cycloalkyl and alkyl fused (C5-C12)aryl-cycloalkyl, which cyclic moiety can include 1-4 non-carbon atoms, which non-carbon atoms are N, O or S and which cyclic moiety can be substituted with one or more of the following: halo, cyano, nitro, hydroxyl, haloalkyl, amino, aminoalkyl, dialkylamino, alkyl, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, (C5-C6)aryl, â€”Oâ€”(C5-C6)aryl; C5-C12)arylcarboxamide, alkylthio or haloalkylthio; R2 and R3 are independently H, alkyl or alkenyl, each of which alkyl or alkenyl can be substituted with 1-3 of the following: halo, hydroxyl, thio, alkylthio, amino, alkylamino, dialkylamino, alkylguanidinyl, dialkylguanidinyl, guanidinyl or amidylguanidine; or R2 or R3 are independently or together â€”RCORâ€², â€”RCOORâ€², â€”RNRâ€²Râ€³Ro or â€”RC(O)NRâ€²Râ€³, where R is alkyl or alkenyl, and Râ€², Râ€³ and Ro are independently H, alkyl, alkenyl, cycloalkyl or (C5-C6)aryl; or R2 and R3 are independently or together a cyclic moiety selected from the group consisting of: cycloalkyl, alkylcycloalkyl, alkenylcycloalkyl, alkyl-oxy(C5-C12)aryl, alkyl-thio(C5-C12)aryl, alkyl-amino(C5-C12)aryl, (C5-C12)aryl, (C5-C12)arylalkyl and (C5-C12)arylalkenyl, which cyclic moiety can include 1-4 non-carbon atoms, which non-carbon atoms are N, O or S and which cyclic moiety can be substituted with one or more of the following: halo, cyano, keto, nitro, hydroxyl, haloalkyl, amino, aminoalkyl, dialkylamino, amidine, alkylamidine, dialkylamidine, alkyl, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, (C5-C6)aryl, â€”Oâ€”(C5-C6)aryl, (C5-C12)arylcarboxamide, alkylthio or haloalkylthio; R2â€² and R3â€² are independently H, alkyl or alkenyl, each of which alkyl or alkenyl can be substituted with 1-3 of the following: halo, hydroxyl, thio, alkylthio, amino, alkylamino, dialkylamino, alkylguanidinyl, dialkylguanidinyl, guanidinyl or amidylguanidine; or R2â€² and R3â€² are independently or together â€”RCORâ€², â€”RCOORâ€², â€”RNRâ€²Râ€³Ro or RC(O)NRâ€²Râ€³, where R is alkyl or alkenyl, and Râ€²Râ€³ and Ro are independently H, alkyl, alkenyl, cycloalkyl or (C5-6)aryl; or R2â€² and R3â€² are independently or together a cyclic moiety selected from the group consisting of: cycloalkyl, alkylcycloalkyl, alkenylcycloalkyl, alkyl-oxy (C5-C12)aryl, alkyl-thio (C5-C12)aryl, alkyl-amino (C5-C12)aryl, (C5-C12)aryl, (C5-C12)arylalkyl and (C5-C12)arylalkenyl, which cyclic moiety can include 1-4 non-carbon atoms, which non-carbon atoms are N, O, or S and which cyclic moiety can be substituted with one or more of the following: halo, cyano, keto, nitro, hydroxyl, haloalkyl, amino, aminoalkyl, dialkylamino, amidine, alkylamidine, dialkylamidine, alkyl, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, (C5-C6)aryl, â€”Oâ€”(C5-C6)aryl, (C5-C12)arylcarboxamide, alkylthio or haloalkylthio; A is a direct bond, â€”C(O)â€”, â€”NHâ€”C(O)â€”, â€”S(O)2â€”, â€”NHâ€”S(O)2â€”, â€”S(O)2â€”NHâ€”, â€”OC(O)NHâ€”, â€”OC(O)â€” or â€”CH2â€”; V1, V2, V3 and V4 are independently C or N; when Vis C, R13 is H, alkyl, halo, alkoxy, carboalkoxy, carboxyl, alkylthio, amino, alkylamino or dialkylamino; or when V3 is C, R13 is a cyclic moiety selected from the group consisting of: (C5-C12)aryl, (C5-C12)arylalkyl, cycloalkyl, alkylcycloalkyl, fused (C5-C12)aryl-cycloalkyl and alkyl fused (C5-C12)aryl-cycloalkyl, which cyclic moiety can include 1 or more non-carbon atoms, which non-carbon atoms are O, N or S and which cyclic moiety can be substituted with one or more of the following: halo or alkyl; when Vis N, then R13 is absent; R14 is H, alkyl, alkenyl, amino, alkylamino or dialkylamino; or R14 is a cyclic moiety selected from the group consisting of: (C5-C12)aryl, (C5-C12)arylalkyl, cycloalkyl, alkylcycloalkyl, fused (C5-C12)aryl-cycloalkyl and alkyl fused (C5-C12)aryl-cycloalkyl, which cyclic moiety can include 1 or more non-carbon atoms, which non-carbon atoms are N, O or S, which cyclic moiety can be substituted with one or more of the following: alkyl, halo, alkoxy, amino, alkylamino, dialkylamino, carboxy, alkenyl, alkynyl, haloalkoxy, carboalkoxy, alkylcarboxamide, (C5-C12)aryl, (C5-C12)arylalkyl, (C5-C12)arylcarboxamide, alkylthio or haloalkylthio; provided that one or more of the following conditions are satisfied: (i) at least one of X and Y is N substituted with a cyclic moiety selected from the group consisting of: (C5-C6)aryl, (C5-C6)arylalkyl and (C5-C6)arylalkenyl, which cyclic moiety can have 1-3 non-carbon atoms, which non-carbon atoms are N, O or S and which cyclic moiety is substituted with hydroxyl; (ii) R1 is alkyl or alkenyl, which alkyl or alkenyl is substituted with one or more of the following: cyano, nitro, alkylamino, dialkylamino, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, (C5-C19)arylcarboxamide or â€”Oâ€”(C5-C6)aryl; or R1 is alkynyl substituted with one or more of the following: halo, hydroxyl, cyano, nitro, haloalkyl, alkylamino, dialkylamino, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, (C5-C12)arylcarboxamide or â€”Oâ€”(C5-C6)aryl; or R1 is hydroxyl, amino or alkylamino; or R1 is a first cyclic moiety selected from the group consisting of: cycloalkenyl, alkylcycloalkenyl, alkenylcycloalkenyl, fused (C5-C12)aryl-cycloalkyl and alkyl fused (C5-C12)aryl-cycloalkyl, which first cyclic moiety can include 1-4 non-carbon atoms, which non-carbon atoms are N, O or S and which first cyclic moiety can be substituted with one or more of the following: halo, cyano, nitro, hydroxyl, haloalkyl, amino, aminoalkyl, dialkylamino, alkyl, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, (C5-C6)aryl, â€”Oâ€”(C5-C6)aryl, (C5-C12)arylcarboxamide, alkylthio or haloalkylthio; or R1 is a second cyclic moiety selected from the group consisting of: cycloalkyl, alkylcycloalkyl and alkenylcycloalkyl, which second cyclic moiety can include 1-4 non-carbon atoms, which non-carbon atoms are N, O or S and which second cyclic moiety is substituted with one or more of the following: hydroxyl or alkylenedioxy; or R1 is a third cyclic moiety selected from the group consisting of: (C5-C12)aryl, (C5-C12)arylalkyl and (C5-C12)arylalkenyl, which third cyclic moiety can include 1-4 non-carbon atoms, which non-carbon atoms are N, O or S and which third cyclic moiety is substituted with one or more hydroxyl; (iii) at least one of R2 and R3 is alkenyl which can be substituted with 1-3 of the following: halo, hydroxyl, thio, alkylthio, amino, alkylamino, dialkylamino, alkylguanidinyl, dialkylguanidinyl, guanidinyl or amidylguanidine; or at least one of R2 and R3 is â€”RCORâ€², â€”RCOORâ€², â€”RNRâ€²Râ€³Ro or â€”RC(O)NRâ€²Râ€³where R is alkyl or alkenyl, and Râ€², Râ€³ and Ro are independently H, alkyl, alkenyl, cycloalkyl or (C5-C12)aryl; or at least one of R2 and R3 is a first cyclic moiety selected from the group consisting of: alkenylcycloalkyl, alkyl-amino (C5-C12)aryl and (C5-C12)arylalkenyl, which first cyclic moiety can include 1-4 non-carbon atoms, which non-carbon atoms are N, O or S and which first cyclic moiety can be substituted with one or more of the following: halo, cyano, keto, nitro, hydroxyl, haloalkyl, amino, aminoalkyl, dialkylamino, amidine, alkylamidine, dialkylamidine, alkyl, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, (C5-C6)aryl, â€”Oâ€”(C5-C6)aryl, (C5-C12)arylcarboxamide, alkylthio or haloalkylthio; or at least one of R2 and R3 is a second cyclic moiety selected from the group consisting of: alkyl-oxy (C5-C12)aryl, alkyl-thio (C5-C12)aryl, cycloalkyl, alkylcycloalkyl, (C5-C12)aryl and (C5-C12)arylalkyl, which second cyclic moiety can include 1-4 non-carbon atoms, which non-carbon atoms are N, O or S and which second cyclic moiety is substituted with one or more of the following: keto, amino, aminoalkyl, dialkylamino, alkylamidine, dialkylamidine, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, alkylcarboxamide, (C5-C6)aryl, â€”Oâ€”(C5-C6)aryl, (C5-C12)arylcarboxamide or haloalkylthio; or (iv) at least one of R2â€² and R3â€² is alkyl substituted with 1-3 of the following: halo, hydroxyl, amino, alkylamino, dialkylamino, alkylguanidinyl, dialkylguanidinyl, guanidinyl or amidylguanidine; or at least one of R2â€² and R3â€² is alkenyl which can be substituted with 1-3 of the following: halo, hydroxyl, thio, alkylthio, amino, alkylamino, dialkylamino, alkylguanidinyl, dialkylguanidinyl, guanidinyl or amidylguanidine; or at least one of R2â€² and R3â€² is â€”RCORâ€², â€”RCOORâ€², â€”RNRâ€²Râ€³Ro or â€”RC(O)NRâ€²Râ€³, where R is alkyl or alkenyl, and Râ€², Râ€³ and Ro are independently H, alkyl, alkenyl, cycloalkyl or (C5-C6)aryl; or at least one of R2â€² and R3â€² is a first cyclic moiety selected from the group consisting of: alkenylcycloalkyl, alkyl-amino(C5-C12)aryl and (C5-C12)arylalkenyl, which first cyclic moiety can include 1-4 non-carbon atoms, which non-carbon atoms are N, O or S and which first cyclic moiety can be substituted with one or more of the following: halo, cyano, keto, nitro, hydroxyl, haloalkyl, amino, aminoalkyl, dialkylamino, amidine, alkylamidine, dialkylamidine, alkyl, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, (C5-C6)aryl, â€”Oâ€”(C5-C6)aryl, (C5-C12)arylcarboxamide, alkylthio or haloalkylthio; or at least one of R2â€² and R3â€² is a second cyclic moiety selected from the group consisting of: alkyl-oxy(C5-C12)aryl, alkyl-thio(C5-C12)aryl, cycloalkyl, alkylcycloalkyl, (C5-C12)aryl and (C5-C12)arylalkyl, which second cyclic moiety can include 1-4 non-carbon atoms, which non-carbon atoms are N, O or S and which second cyclic moiety is substituted with one or more of the following: keto, amino, aminoalkyl, dialkylamino; alkylamidine, dialkylamidine, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, alkylcarboxamide, (C5-C6)aryl, â€”Oâ€”(C5-C6)aryl, (C5-C12)arylcarboxamide or haloalkylthio; or a pharmaceutically acceptable salt thereof.