Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
First Claim
Patent Images
1. A compound of formula I, or a pharmaceutically acceptable salt thereof:
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wherein---- represents a double or single bond;
X and Y are N;
Z is O;
Ar1 and Ar2 are independently selected from the group consisting of;
optionally substituted phenyl and optionally substituted 2-pyridyl wherein at least one of Ar1 and Ar2 is phenyl and at least one of Ar1 and Ar2 is 2-pyridyl and at least one of Ar1 and Ar2 is substituted with at least one substituent G;
wherein G is selected from the group consisting of;
haloalkyl;
pyridyl;
thiophene;
pyrimidine;
furan;
cycloalkene;
alkenyl;
alkynyl;
A-alkenyl;
A-alkynyl;
A-alkyloxy;
—
R2OR3;
—
R2OC(O)R3;
(CH2)m—
NR2R3;
—
OCH2CH(Cl)CH2Cl; and
substituted aryl wherein the aryl substituent is R4, and wherein A is a linker selected from the group consisting of;
CH2;
O;
NH;
S;
SO;
SO2;
NSO2;
—
OSO2; and
—
C(NR2)NR3;
m is selected from 0 and 1;
R2 and R3 may be independently selected from the group consisting of;
H;
alkyl;
haloalkyl;
alkyloxy;
alkylamine;
cycloalkyl;
heterocycloalkyl;
aryl;
heteroaryl;
alkylaryl;
alkylheteroaryl;
haloaryl;
alkyloxyaryl;
alkenylaryl;
alkenyloxyaryl; and
haloheteroaryl; and
R4 is selected from the group consisting of;
halo;
—
OR2;
—
SR2;
—
SOR2;
—
SO2R2;
—
SO2NR2R3;
—
R2OR3;
—
R2SR3;
—
OCOR2;
—
OCONR2R3;
—
NR2COR3;
—
NR2CO2R3;
—
CN;
—
NO2;
—
C(NR2)NR3;
—
CO2R2R3;
—
CONR2R3;
—
C(O)R2;
—
CH(OR2)R3;
—
CH2(OR2);
—
A—
(CH2)m—
NR2R3;
NR2R3;
aryl;
aralkyl;
heteroaryl; and
heteroaralkyl; and
Ar1, Ar2, and the substituent G are optionally further substituted with one or more substituents selected independently from the group consisting of R2 and R4, with the proviso that when ---- represents a double bond, then either of Ar1 or Ar2 is pyridyl and the compound is not;
3-(2-pyridyl)-5-(4-aminophenyl)-1,2,4-oxadiazole, 3-(2-pyridyl)-5-{2-[2-(N,N,dimethylamino)-ethyl]oxyphenyl}-1,2,4-oxadiazole, 3-(2-Pyridyl)-5-(2-chlorophenyl)-1,2,4-oxadiazole, or 3-(2-pyridyl)-5-phenyl-1,2,4-oxadiazole.
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Abstract
The present invention provides compounds and pharmaceutical compositions that act as antagonists at metabotropic glutamate receptors, and that are useful for treating neurological diseases and disorders. Methods of preparing the compounds also are disclosed.
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Citations
58 Claims
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1. A compound of formula I, or a pharmaceutically acceptable salt thereof:
-
wherein ---- represents a double or single bond;
X and Y are N;
Z is O;
Ar1 and Ar2 are independently selected from the group consisting of;
optionally substituted phenyl and optionally substituted 2-pyridyl wherein at least one of Ar1 and Ar2 is phenyl and at least one of Ar1 and Ar2 is 2-pyridyl and at least one of Ar1 and Ar2 is substituted with at least one substituent G;
wherein G is selected from the group consisting of;
haloalkyl;
pyridyl;
thiophene;
pyrimidine;
furan;
cycloalkene;
alkenyl;
alkynyl;
A-alkenyl;
A-alkynyl;
A-alkyloxy;
—
R2OR3;
—
R2OC(O)R3;
(CH2)m—
NR2R3;
—
OCH2CH(Cl)CH2Cl; and
substituted aryl wherein the aryl substituent is R4, andwherein A is a linker selected from the group consisting of;
CH2;
O;
NH;
S;
SO;
SO2;
NSO2;
—
OSO2; and
—
C(NR2)NR3;
m is selected from 0 and 1;
R2 and R3 may be independently selected from the group consisting of;
H;
alkyl;
haloalkyl;
alkyloxy;
alkylamine;
cycloalkyl;
heterocycloalkyl;
aryl;
heteroaryl;
alkylaryl;
alkylheteroaryl;
haloaryl;
alkyloxyaryl;
alkenylaryl;
alkenyloxyaryl; and
haloheteroaryl; and
R4 is selected from the group consisting of;
halo;
—
OR2;
—
SR2;
—
SOR2;
—
SO2R2;
—
SO2NR2R3;
—
R2OR3;
—
R2SR3;
—
OCOR2;
—
OCONR2R3;
—
NR2COR3;
—
NR2CO2R3;
—
CN;
—
NO2;
—
C(NR2)NR3;
—
CO2R2R3;
—
CONR2R3;
—
C(O)R2;
—
CH(OR2)R3;
—
CH2(OR2);
—
A—
(CH2)m—
NR2R3;
NR2R3;
aryl;
aralkyl;
heteroaryl; and
heteroaralkyl; and
Ar1, Ar2, and the substituent G are optionally further substituted with one or more substituents selected independently from the group consisting of R2 and R4, with the proviso that when ---- represents a double bond, then either of Ar1 or Ar2 is pyridyl and the compound is not;
3-(2-pyridyl)-5-(4-aminophenyl)-1,2,4-oxadiazole, 3-(2-pyridyl)-5-{2-[2-(N,N,dimethylamino)-ethyl]oxyphenyl}-1,2,4-oxadiazole, 3-(2-Pyridyl)-5-(2-chlorophenyl)-1,2,4-oxadiazole, or 3-(2-pyridyl)-5-phenyl-1,2,4-oxadiazole. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30)
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31. A compound selected from the group consisting of:
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3-(5-Methyl-pyrid-2-yl)-5-(3-cyanophenyl)-1,2,4-oxadiazole (B57), 3-(5-Cyano-pyrid-2-yl)-5-(3-cyanophenyl)-1,2,4-oxadiazole (B58), 3-(2-Pyridyl)-5-(5-bromo-2-methoxyphenyl)-1,2,4-oxadiazole (B62), 3-(2-Pyridyl)-5-(5-bromo-2-fluorophenyl)-1 ,2,4-oxadiazole (B63), 3-(2-Pyridyl)-5-(5-cyano-2-fluorophenyl)-1,2,4-oxadiazole (B64), 3-(2-Pyridyl)-5-(3-cyano-5-methylphenyl)-1,2,4-oxadiazole (B73), 3-(2-Pyridyl)-5-(3-fluoro-5-bromophenyl)-1,2,4-oxadiazole (B74), 3-(2-Pyridyl)-5-(3-iodo-5-bromophenyl)-1,2,4-oxadiazole (B75), 3-(5-Fluoro-2-pyridyl)-5-(3-fluoro-5-bromophenyl)-1,2,4-oxadiazole (B76), 3-(2-Pyridyl)-5-(3-iodo-5-(methylphenylester)-1,2,4-oxadiazole (B78), 3-(2-Pyridyl)-5-(3-methoxy-5-(methoxycarbonyl)phenyl)-1,2,4-oxadiazole (B79) 3-(2-Pyridyl)-5-(3-bromo-5-cyanophenyl)-1,2,4-oxadiazole (B80), 3-(2-Pyridyl)-5-(5-cyano-3-iodophenyl)-1,2,4-oxadiazole (B81), 3-(5-Cyano-2-pyridyl)-5-(3-bromophenyl)-1,2,4-oxadiazole (B59), 3-(5-Cyano-2-pyridyl)-5-(3-cyano-5-fluorophenyl)-1,2,4-oxadiazole (B60), 3-(5-Cyano-2-pyridyl)-5-(3-bromo-5-fluorophenyl)-1,2,4-oxadiazole (B61), 3-(2-Pyridyl)-5-(5-cyano-2-methoxyphenyl)-1,2,4-oxadiazole (B97), 3-(2-Pyridyl)-5-(2-cyano-5-methoxyphenyl)-1,2,4-oxadiazole (B98), 3-(2-Pyridyl)-5-(3-cyano-5-(methoxycarbonyl)phenyl)-1,2,4-oxadiazole (B100), 3-(2-Pyridyl)-5-(3-cyano-5-methoxyphenyl)-1,2,4-oxadiazole (B134), 3-(2-Pyridyl)-5-(3-cyano-5-hydroxyphenyl)-1,2,4-oxadiazole (B137), 3-(2-Pyridyl)-5-(3-cyano-5-propoxyphenyl)-1,2,4-oxadiazole (B141), 2-(2-Pyridyl)-5-(3-iodophenyl)-1,3,4-oxadiazole (B148), 2-(2-Pyridyl)-5-(3-cyanophenyl)-1,3,4-oxadiazole (B149), 3-(5-Chloropyrid-2-yl)-5-(3-cyano-5-fluorophenyl)-1,2,4-oxadiazole (B83), 3-(5-Chloropyrid-2-yl)-5-(3-cyano-5-chlorophenyl)-1,2,4-oxadiazole (B84), 3-(5-Chloropyrid-2-yl)-5-(3-chloro-5-fluorophenyl)-1,2,4-oxadiazole (B85), 3-(5-Chloropyrid-2-yl)-5-(3-cyano-5-methoxyphenyl)-1,2,4-oxadiazole (B86), 3-(5-Fluoropyrid-2-yl)-5-(3-cyano-5-chlorophenyl)-1,2,4-oxadiazole (B87), 3-(5-Fluoropyrid-2-yl)-5-(3-fluoro-5-chlorophenyl)-1,2,4-oxadiazole (B88), 3-(5-Fluoropyrid-2-yl)-5-(3-cyano-5-methoxyphenyl)-1,2,4-oxadiazole (B89), 3-(5-Cyanopyrid-2-yl)-5-(3-cyano-5-chlorophenyl)-1,2,4-oxadiazole (B90), 3-(5-Cyanopyrid-2-yl)-5-(3-fluoro-5-chlorophenyl)-1,2,4-oxadiazole (B91) 3-(5-Cyanopyrid-2-yl)-5-(3-cyano-5-methoxyphenyl)-1,2,4-oxadiazole (B92), 3-(5-Fluoropyrid-2-yl)-5-(3,5-di-cyanophenyl)-1,2,4-oxadiazole (B93), 3-(3-(4-Dimethylaminobutoxy)-pyrid-2-yl)-5-(3-cyano-5-fluorophenyl)-1,2,4-oxadiazole (B94) 3-(3-(5-Dimethylaminopentyloxy)-pyrid-2-yl)-5-(3-Cyano-5-fluorophenyl)-1,2,4-oxadiazole (B95), and [3-(3-(6-Dimethylaminohexyloxy)-pyrid-2-yl)-5-(3-cyano-5-fluorophenyl)-1,2,4-oxadiazole](B96).
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32. A compound selected from the group consisting of:
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3-(2-Pyridyl)-5-(methoxycarbonyl)phenyl)-1,2,4-oxadiazole (B77), 3-(2-Pyridyl)-5-(3-N,N-dimethylaminophenyl)-1,2,4-oxadiazole (B82), 3-(2-Pyridyl)-5-(3-cyano-5-(4-pyridyl)phenyl)-1,2,4-oxadiazole (B101), 3-(2-Pyridyl)-5-[2-methoxy-5-(4-pyridyl)phenyl]-1,2,4-oxadiazole (B102), 3-(2-pyridyl)-5-[2-fluoro-5-(4-pyridyl)phenyl]-1,2,4-oxadiazole (B103), 3-(2-Pyridyl)-5-(3-fluoro-5-(4-pyridyl)phenyl)-1,2,4-oxadiazole (B104), 3-(2-Pyridyl)-5-(3-fluoro-5-(3-pyridyl)phenyl)-1,2,4-oxadiazole (B105), 3-(2-Pyridyl)-5-[2-fluoro-5-(3pyridyl)phenyl]-1,2,4-oxadiazole (B106), 3-(2-Pyridyl)-5-[2-methoxy-5(3-pyridyl)phenyl]-1,2,4-oxadiazole (B107), 3-(2-Pyridyl)-5-(3-cyano-5-(3-pyridyl)phenyl)-1,2,4-oxadiazole (B108), 3-(5-Fluoro-2pyridyl)-5(3-pyridyl)phenyl)-1,2,4-oxadiazole (B109), 3-(5-Cyanopyrid-2-yl-5-(3-(pyrid-3-yl)phenyl)-1,2,4-oxadiazole (B112), 3-(5-Cyanopyrid-2-yl)-5-(3-fluoro-5-(pyrid-3-yl)phenyl)-1,2,4-oxadiazole (B113), 3-(2-Pyridyl)-5-(3-cyano-5-(2-pyridyl)phenyl)-1,2,4-oxadiazole (B124), 3-(2Pyridyl)5-[2-methoxy-5-(2-pyridyl)phenyl]-1,2,4-oxadiazole (B125), 3-(2-Pyridyl)-5-[2-fluoro-5-(2-pyridyl)phenyl]-1,2,4-oxadiazole (B126), 3-(2-Pyridyl)-5-[(3-(3-fluorophenyl)-5-fluorophenyl)]-1,2,4-oxadiazole (B114), 3-(2-Pyridyl)-5-(3-cyano-5-(3-thiophene)phenyl)-1,2,4-oxadiazole (B115), 3-(2-Pyridyl)-5-(3-cyano-5-(5-pyrimidyl)phenyl)-1,2,4-oxadiazole (B120), 3-(2-Pyridyl)-5-(3-cyano-5-(3-aminophenyl)phenyl)-1,2,4-oxadiazole (B121), 3-(2-Pyridyl)-5-(3-fluorophenyl)phenyl)-1,2,4-oxadiazole (B122), 3-(2-Pyridyl)-5(3-aminomethyl-5-cyanophenyl)-1,2,4-oxadiazole (B127), 3-(2-Pyridyl)-5-(3-cyano-5-vinylphenyl)-1,2,4-oxadiazole (B129), 3-(2-Pyridyl)-5-(3-cyano-5-(2-hydroxyethyl)phenyl)-1,2,4-oxadiazole (B130), 3-(2-Pyridyl)-5-(3-cyano-5-(2,3-dichloropropoxy)phenyl)-1,2,4-oxadiazole (B131), 3-(2-Pyridyl)-5-(3-allyloxy-5-carboxyphenyl)-1,2,4-oxadiazole (B135), 3-(2-Pyridyl)-5-(3-allyloxy-5-cyanophenyl)-1,2,4-oxadiazole (B136), 3-(2-Pyridyl)-5-(5-cyano-3-[3-hydroxypropyn-1-yl]phenyl)-1,2,4-oxadiazole (B142), and 3-(2-Pyridyl)-5-(2-N-methylaminophenyl)-1,2,4-oxadiazole (B
144).
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33. A compound of Formula I, or a pharmaceutically acceptable salt thereof:
-
wherein X and Y are N;
Z is O;
Ar1 and Ar2 are independently selected from the group consisting of optionally substituted phenyl and optionally substituted 2-pyridyl wherein at least one of Ar1 and Ar2 is phenyl and at least one of Ar1 and Ar2 is 2-pyridyl, wherein at least one of Ar1 and Ar2 is substituted with at least one substituents G, wherein
G is selected from the group consisting of —
F, —
Cl, —
Br, —
I, —
SR1, —
SOR, —
SO2R1, —
SO2NR1R2, —
OCOR1, —
OCONR1R2, —
NR1COR2, —
NR1CO2R2, —
CN, —
NO2, —
CO2R1, —
CONR1R2, —
C(O)R1, —
CH(OR1)R2, —
CH2(OR1), —
R1, and —
A—
(CH2)n—
NR1R2,wherein
R1 and R2 are independently selected from the group consisting of —
H, —
CF3, —
C1-C10 alkyl, -cycloalkyl, -alkyl-aryl, -alkyl-heteroaryl, -heterocycloalkyl, -aryl and where R1 and R2 may combine to form a ring, and A is defined as CH2, O, NH, S, SO, or SO2 and n is 1,2,3, or 4,with the proviso that when ---- represents a double bond, then either of Ar1 or Ar2 is pyridyl and the compound is not;
3-(2-Pyridyl)-5-(2-nitrophenyl)-1,2,4-oxadiazole, 3-(2-Pyridyl)-5-(2-chlorophenyl)-1,2,4-oxadiazole, 3-(2-pyridyl)-5-(4-nitrophenyl)-1,2,4-oxadiazole, 3-(2-pyridyl)-5-(4-aminophenyl)-1,2,4-oxadiazole, 3-(2-pyridyl)-5-{2-[2-(N,N,dimethylamino)-ethyl]oxyphenyl}-1,2,4-oxadiazole, or 3-(2-pyridyl)-5-phenyl-1,2,4-oxadiazole. - View Dependent Claims (34, 35, 36, 37, 45, 46, 47, 48, 49, 50, 51)
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38. A compound selected from the group consisting of:
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3-(2-pyridyl)-5-(3-methoxyphenyl)-1,2,4-oxadiazole (B1), 3-(2-pyridyl)-5-(3,5-dichlorophenyl)-1,2,4-oxadiazole (B2), 3-(2-pyridyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole (B3), 3-(2-pyridyl)-5-(3-methylphenyl)-1,2,4-oxadiazole (B9), 3-(2-pyridyl)-5-[3-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole (B11), 3-(2-pyridyl)-5-(2,3-difluorophenyl)-1,2,4-oxadiazole (B16), 3-(2-pyridyl)-5-(2,5-difluorophenyl)-1,2,4-oxadiazole (B17), 3-(2-pyridyl)-5-(3,5-difluorophenyl)-1,2,4-oxadiazole (B18), 3-(2-pyridyl)-5-(3-nitrophenyl)-1,2,4-oxadiazole (B19), 3-(2-pyridyl)-5-(3-cyanophenyl)-1,2,4-oxadiazole (B21), 3-(2-pyridyl)-5-(3-bromophenyl)-1,2,4-oxadiazole (B22), 3-(2-pyridyl)-5-(3,5-dimethoxyphenyl)-1,2,4-oxadiazol (B23), 3-(2-pyridyl)-5-(2,3-dichlorophenyl)-1,2,4-oxadiazole (B25), 3-(2-pyridyl)-5-(3-chloro-5-cyanophenyl)-1,2,4-oxadiazole (B26), 3-(2-pyridyl)-5-(3-fluoro-5-cyanophenyl)-1,2,4-oxadiazole (B27), 3-(2-pyridyl)-5-(3-chloro-5-fluorophenyl)-1,2,4-oxadiazole (B28), 3-(5-chloropyrid-2-yl)-5-(3-cyanophenyl)-1,2,4-oxadiazole (B29) 3-(5-fluoropyrid-2-yl)-5-(3-cyanophenyl)-1,2,4-oxadiazole (B30), 3-(5-fluoropyrid-2-yl)-5-(3-cyano-5-fluorophenyl)-1,2,4-oxadiazole (B31), 3-(3-fluoropyrid-2-yl)-5-(3-cyanophenyl)-1,2,4-oxadiazole (B32), 3-(5-fluoropyrid-2-yl)-5-(3,5-dimethoxyphenyl)-1,2,4-oxadiazole (B33), 3-(5-methoxypyrid-2-yl)-5-(3-cyanophenyl)-1,2,4-oxadiazole (B34), 3-(2-quinolinyl)-5-(3-cyanophenyl)-1,2,4-oxadiazole (B35), 3-(3-chloro-5-trifluoromethylpyrid-2-yl)-5-(3-cyanophenyl)-1,2,4-oxadiazole (B36), 3-(2pyridyl)-5-(5-chloro-2-methoxyphenyl)-1,2,4-oxadiazole (B37), 3-(2-pyridyl)-5-(2-chloro-5-methylthiophenyl)-1,2,4-oxadiazole (B39), 3-(2-pyridyl)-5-(2-bromo-5-methoxyphenyl)-1,2,4-oxadiazole (B42), and 3-(2-pyridyl)-5-(2,5,6-trifluorophenyl)-1,2,4-oxadiazole (B45).
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39. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective, non-toxic, amount of a compound of Formula I:
-
wherein ---- represents a double or single bond;
X and Y are N;
Z is O;
Ar1 and Ar2 are independently selected from the group consisting of;
optionally substituted phenyl and optionally substituted 2-pyridyl wherein at least one of Ar1 and Ar2 is phenyl and at least one of Ar1 and Ar2 is 2-pyridyl and at least one of Ar1 and Ar2 is substituted with at least one substituent G;
wherein G is selected from the group consisting of;
haloalkyl;
pyridyl;
thiophene;
pyrimidine;
furan;
cycloalkene;
alkenyl;
alkynyl;
A-alkenyl;
A-alkynyl;
A-alkyloxy;
-R2OR3;
—
R2OC(O)R3;
(CH2)m-NR2R3;
—
OCH2CH(Cl)CH2Cl; and
substituted aryl wherein the aryl substituent is R4, andwherein A is a linker selected from the group consisting of;
CH2;
O;
NH;
S;
SO;
SO2;
NSO2;
—
OSO2; and
—
C(NR2)NR3;
m is selected from 0 and 1;
R2 and R3 may be independently selected from the group consisting of;
H;
alkyl;
haloalkyl;
alkyloxy;
alkylamine;
cycloalkyl;
heterocycloalkyl;
aryl;
heteroaryl;
alkylaryl;
alkylheteroaryl;
haloaryl;
alkyloxyaryl;
alkenylaryl;
alkenyloxyaryl; and
haloheteroaryl; and
R4 is selected from the group consisting of;
halo;
—
OR2;
—
SR2;
—
SOR2;
—
SO2R2;
—
SO2NR2R3;
—
R2OR3;
—
R2SR3;
—
OCOR2;
—
OCONR2R3;
—
NR2COR3;
—
NR2CO2R3;
—
CN;
—
NO2;
—
C(NR2)NR3;
—
CO2R2R3;
—
CONR2R3;
—
C(O)R2;
—
CH(OR2)R3;
—CH2(OR2);
—
A—
(CH2)m-NR2R3;
NR2R3;
aryl;
aralkyl;
heteroaryl; and
heteroaralkyl; and
Ar1, Ar2, and the substituent G are optionally further substituted with one or more substituents selected independently from the group consisting of R2 and R4, with the proviso that when ---- represents a double bond, then either of Ar1 or Ar2 is pyridyl and the compound is not;
3-(2-pyridyl)-5-(4-aminophenyl)-1,2,4-oxadiazole, 3-(2-Pyridyl)-5-(2-chlorophenyl)-1,2,4-oxadiazole, 3-(2-pyridyl)-5-(4-nitrophenyl)-1,2,4-oxadiazole, 3-(2-pyridyl)-5-phenyl-1,2,4-oxadiazole, and 3-(2-pyridyl)-5-{2-[2-(N,N,dimethylamino)-ehtyl]oxyphenyl}-1,2,4-oxadiazole. - View Dependent Claims (40, 41, 42, 43, 44)
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52. A compound, or a pharmaceutically acceptable salt thereof, selected from the group consisting of compounds as set forth in the following table:
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53. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective, non-toxic, amount of a compound of Formula I:
-
wherein X and Y are N;
Z is O;
Ar1 and Ar2 are independently selected from the group consisting of optionally substituted phenyl and optionally substituted 2-pyridyl wherein at least one of Ar1 and Ar2 is phenyl and at least one of Ar1 and Ar2 is 2-pyridyl, wherein Ar1 and Ar2 are optionally substituted with one or more substituents G, wherein
G is selected from the group consisting of —
F, —
Cl, —
Br, —
I, —
SR1, —
SOR, —
SO2R1, —
SO2NR1R2, —
OCOR1, —
OCONR1R2, —
NR1CO2R2, —
NR1CO2R2, —
CN, —
NO2, —
CO2R1, —
CONR1R2, —
C(O)R1, —
CH(OR1)R2, —
CH2(OR1), —
R1, and —
A—
(CH2)n—
NR1R2,wherein
R1 and R2 are independently selected from the group consisting of —
H, —
CF3, —
C1-C10 alkyl, -cycloalkyl, -alkyl-aryl, -alkyl-heteroaryl, -heterocycloalkyl, -aryl and where R1 and R2 may combine to form a ring, and A is defined as CH2, O, NH, S, SO, or SO2 and n is 1, 2, 3, or 4,with the proviso that when ---- represents a double bond, then either of Ar1 or Ar2 is pyridyl and the compound is not;
3-(2-Pyridyl)-5-(2-chlorophenyl)-1,2,4-oxadiazole, 3-(2-pyridyl)-5-(4-nitrophenyl)-1,2,4oxadiazole, 3-(2pyridyl)5-(4-aminophenyl)-1,2,4-oxadiazole, 3-(2-pyridyl)-5-{2[2-(N,N,dimethylamino)-ethyl]oxyphenyl}-1,2,4-oxadiazole, or 3-(2-pyridyl)-5-phenyl-1,2,4-oxadiazole. - View Dependent Claims (54, 55, 56, 57, 58)
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Specification