Thiadiazole antifungal agents
OwnerDingwei Tim Yu, Orest Taras Macina +3inventors
InventorsDingwei Tim Yu, Orest Taras Macina, Ila Sircar, Jagadish Chandra Sircar, Christopher Mark Riviello
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Abstract
Disclosed is a novel class of thiazole, thiadiazole, and oxadiazole compounds which are substituted at their nuclear carbons by aromatic moieties. These compounds exhibit antifungal activity against a variety of fungi including strains which have proven to be resistant to treatment with known antifungal agents such as Fluconazole.
Claims20
A compound of the formula:
- 33
- wherein:
- Ar is phenyl, thienyl or pyridyl substituted by R1 and R2;
- where R1, R2 are the same or different and represent hydrogen, halo, alkyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, alkylthio, amino, hydroxy, cyano, nitro, carboxy, aminocarbonyl or aminosulfonyl, alkylamino, dialkylamino, acylamino, dialkylaminosulfonyl or alkylaminosulfonyl or taken together R1 and R2 may be combined to form —O—(CH2)n—O— where n is an integer having a value of 1 or 2;
- R3 and R4 are the same or different and represent hydrogen, alkyl which may be optionally substituted by amino, alkylamino, dialkylamino, hydroxy, cyano, carboxy alkenyl, alkynyl or acyl, taken together R3 and R4 may be combined to form —(CH2)m—Q—(CH2)m′— where Q is selected from among CH2, O, S(O)n or NR7 where n is an integer having a value of 0, 1, or 2;
- R7 is lower alkyl and m and m′ are integers having a value of 2 with the proviso that when Q is CH2, m′ may also have a value of 1;
- R5 is H, halo, OR, OH, NO2, NH2 and NHCOR where R is alkyl, lower alkyl or aryl;
- X is N, O or S,
- Y is N or S;
- with the proviso when X is O or S, Y must be N;
- Z is N, CR8, where R8 is hydrogen, halo, lower alkyl or alkoxycarbonyl;
- with the proviso that X, Y, Z cannot all represent N at the same time;
- VR3R4 represents heterocyclic rings selected from among pyrrole, immidazole, 1,3,4-triazole,1,2,4-triazole and pyrazole linked via the nitrogen;
- V is N, O, or S;
- and P is 1-3;
- and the non-toxic pharmacologically acceptable salts thereof.
allylaminomethyl)phenyl]-thiazole2-(4-nitrophenyl)-4-[4″-(N-methyl-N-allylaminomethyl)phenyl]-thiazole.
2-(3′-nitrophenyl)-4-[4″-(N-methyl-N-allylaminomethyl)phenyl]thiazole.
2-(4′-methoxy-3-nitrophenyl)-4-[4″-(dimethylaminomethyl)phenyl]thiazole.
2-(4′methoxy-3-nitrophenyl)-4-[4″-N-methyl-N-allylaminomethyl)phenyl]thiazole.
Dependencies are inferred from the claim text.