US 9,540,350 B2Granted

1-substituted, 4-(substituted phenoxymethyl)-1,2,3-triazole compounds with antifungal properties and methods for preparation thereof

AssigneesFDC Limited, Council of Scientific and Industrial Research

InventorsHanumant Bapurao Borate, Ananda Shahaji Kudale, Subhash Prataprao Chavan, Sunita Sharad Kunte, Mohan Anand Chandavarkar, Ramkrishnan Ramachandran Iyer, Amit Chandrakant Tawte, Deepali Damodar Rao

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Abstract

Disclosed herein are novel antifungal compounds of Formula 1, containing 1-substituted, 4-(substituted phenoxy-methyl)-1,2,3-triazole moieties coupled to a core having triazole ring, (un)substituted phenyl ring and tertiary alcoholic functionality, and pharmaceutically acceptable salts thereof; methods for preparing these compounds; and pharmaceutical preparations containing these novel compounds for prevention and treatment of fungal infections.

Claims16

Dependent claims

An antifungal compound of Formula 1, or a pharmaceutically acceptable salt thereof,

wherein R1 and R2 are independently selected from the group consisting or hydrogen and a halogen;
R3 is selected from the group consisting of hydrogen, a halogen, a substituted or unsubstituted alkyl having a linear or branched chain of 1 to 20 carbon atoms, a substituted or unsubstituted aryl, nitro, a substituted or unsubstituted alkylamino, a substituted or unsubstituted arylamino, a substituted or unsubstituted heteroarylamino,
C(O)R4, —COCH═CHR5, —CH═CH—COR6, or a substituted or unsubstituted alkenyl;
R4 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl having a linear or branched chain of 1 to 20 carbon atoms, and a substituted or unsubstituted alkenyl having a linear or branched chain of 1 to 20 carbon, atoms;
and
R5 selected from the group consisting of a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, and a substituted or unsubstituted heteroaryl.

3 more elements

An antifungal compound selected from the group consisting of:

(E)-1-(4-((1-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-phenylprop-2-en-1-one;
(E)-1-(4-((1-(2-(2,4-diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one;
(E)-1-(4-((1-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(4-methylphenyl)prop-2-en-1-one;
(E)-1-(4-((1-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(2-thienyl)prop-2-en-1-one;
(E)-1-(4-((1-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one;
(E)-3-(4-((1-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-(4-fluorophenyl)prop-2-en-1-one;
(E)-4-(4-((1-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)but-3-en-2-one;
(E)-1-(Cyclopropyl)-3-(4-((1-(2-(2,4-diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)prop-2-en-1-one;
(E)-3-(4-((1-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-(4-(4-propylpiperazin-1-yl)phenyl)prop-2-en-1-one;
(E)-1-(4-(4-n-Butylpiperazin-1-yl)phenyl)-3-(4-((1-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)prop-2-en-1-one;
(E)-3-(4-((1-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-(4-(4-n-pentylpiperazin-1-yl)phenyl)prop-2-en-1-one;
(E)-3-(4-((1-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-(4-(4-(4-methoxybenzyl)piperazin-1-yl)phenyl)prop-2-en-1-one;
(1E,4E)-1-(4-(Buta-2,3-dienyloxy)phenyl)-5-(4-((1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)penta-1,4-dien-3-one;
(E)-1-(4-(2-(2,4-Diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propoxy)phenyl)-3-(4-((1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)prop-2-en-1-one;
(E)-1-(4-((4-(But-1-en-1-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol;
(E)-2-(2,4-Diflourophenyl)-1-(4-((4-(n-hex-1-en-1-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol;
(E)-2-(2,4-Diflourophenyl)-1-(4-((4-(n-dodec-1-en-1-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol;
(E)-2-(2,4-Diflourophenyl)-1-(4-((4-(prop-1-en-1-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol;
2-(2,4-Diflourophenyl)-1-(4-phenyloxymethyl-1H-1,2,3-triazol-1-yl)-3-1,2,4-triazol-1-yl)propan-2-ol;
4-((1-(2-(2,4-diflourophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde;
2-(2,4-Difluorophenyl)-1-(4-(4-acetylphenyloxy)methyl-1H-1,2,3-triazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol;
1-(4-(4-Acetylaminophenyloxy)methyl-1H-1,2,3-triazol-1-yl)-2-2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol;
2-(2,4-Difluorophenyl)-1-(4-(4-methylphenyloxy)methyl-1H-1,2,3-triazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol;
and
3-Amino-4′-((1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)-6-methylbiphenyl-2,4-dicarbonitrile.

22 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/771,991Filed 21 Feb 2014
Priority: IN 626/MUM/20131 Mar 2013
Published: US 2016/0009692 A114 Jan 2016
Granted: 10 Jan 2017
Term ends: Not estimatedThe source records don’t support an estimate.

Classification13 codes

C07D 403/06
Containing two hetero rings: linked by a carbon chain containing only aliphatic carbon atoms
A01N 43/653
Triazoles; Hydrogenated triazoles: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
A61K 31/4196
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: 1,2,4-Triazoles
A61K 31/496
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: non-condensed piperazines…