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4-HYDROXYPHENYL PHOSPHONIUM SALTS WITH ANTI-PARASITIC PROPERTIESCM Patents

The present invention provides a new series of compounds derived from 4-hydroxyphenyl phosphonium. The invention also relates to a pharmaceutical composition comprising the compounds and to the use thereof in the treatment or prevention of diseases caused by parasites, preferably trypanosomatid parasites. In particular, these compounds have demonstrated effectiveness in vivo for the treatment of visceral leishmaniasis in a mouse model. These diseases can occur in humans and in animals.

Datos clave

CategoríaInvención

Índice de la ficha

Updated at
05/11/2026
Numero publicacion
EP.3995502.A1
Fecha publicacion
11/05/2022
Anio publicacion
2022
Numero solicitud
EP20200835530

En detalle

Reivindicaciones

1. A compound of general formula (I), pharmaceutically acceptable salt, or solvate thereof <img class="EMIRef" id="6a00799e-92a5-4f5e-a0d0-eebd9eb92548-ib0003" /> wherein: R<1> is selected from OH and CH<3>; R<2> and R<3> are independently selected from C<1>-C<6> alkyl, cycloalkyl, aryl or heterocycle; X is a halogen. 2. The compound according to claim 1, wherein R<1> is OH. 3. The compound according to any of claims 1-2, wherein R<2> and R<3> are aryls, and more preferably phenyl. 4. The compound according to any of claims 1-2, wherein R<2> and R<3> are 1-naphthalenyl. 5. The compound according to any of claims 1-2, wherein R<2> is 2-pyridyl and R<3> is phenyl. 6. The compound according to claim 1 selected from the list comprising: - (15-(2,4-dihydroxyphenyl)-15-oxopentadecyl)triphenylphosphonium bromide (1) TAO99 - (16-(4-hydroxy-2-methylphenyl)-16-oxohexadecyl)triphenylphosphonium bromide (2) TAO100 - (16-(4-hydroxy-2-methylphenyl)-16-oxohexadecyl)diphenyl(pyridin-2-yl)phosphonium bromide (3) TAO101 - (16-(2,4-dihydroxyphenyl)-16-oxohexadecyl)tri(naphthalen-1-yl)phosphonium bromide (4) (TAO118). 7. A pharmaceutical composition comprising a compound of general formula (I) described according to any of claims 1 to 6, together with a pharmaceutically acceptable carrier. 8. The composition according to claim 7, further comprising another anti-parasitic active ingredient. 9. The compound of general formula (I) described according to any of claims 1 to 6 for use as a drug. 10. The compound of general formula (I) for use as a drug according to claim 9, wherein the drug is for the prevention and/or treatment of diseases caused by parasites. 11. The compound of general formula (I) for use as a drug according to claim 10, wherein the disease is caused by protozoan parasites. 12. The compound of general formula (I) for use as a drug according to claim 11, wherein the protozoan parasites are of the genus Leishmania or Trypanosoma. 13. The compound of general formula (I) for use as a drug according to claim 12, wherein the parasites are of the species L. aethiopica, L. amazonensis, L. arabica, L. archibaldi, L. aristedesi, L. braziliensis, L. chagasi (syn. L. infantum), L. colombiensis, L. deanei, L. donovani, L. enriettii, L. equatorensis, L. forattinii, L. garnhami, L. gerbili, L. guyanensis, L. herreri, L. hertigi, L. infantum, L. killicki, L. lainsoni, L. major, L. mexicana, L. naiffi, L. panamensis, L. peruviana, L. pifanoi, L. shawi, L. tarentolae, L. tropica, L. turanica, L. venezuelensis, Trypanosoma brucei, T. cruzi, T. congolense, T. equinum, T. equiperdum, T. evansi, T. vivax. 14. The compound of general formula (I) for use as a drug according to any of claims 9 to 13, wherein the diseases occur in animals, preferably in a mammal. 15. The compound of general formula (I) for use as a drug according to any of claims 9 to 14, wherein the disease is selected from leishmaniasis, human African trypanosomiasis (sleeping sickness), animal trypanosomiasis, American trypanosomiasis (Chagas disease).

Etiquetas

Inventores
Dardonville ChristopheDARDONVILLE, ChristopheCueto Díaz Eduardo JoséCUETO DÍAZ, Eduardo JoséGAMARRO CONDE, FranciscoGamarro Conde FranciscoManzano González José IgnacioMANZANO GONZÁLEZ, José IgnacioPEREA MARTÍNEZ, AnaPerea Martínez AnaALUNDA RODRÍGUEZ, José MaríaAlunda Rodríguez José MaríaTorrado Durán Juan JoséTORRADO DURÁN, Juan JoséOlías Molero Ana IsabelOLÍAS MOLERO, Ana Isabel
Solicitantes
Consejo Superior de Investigaciones CientíficasUniversidad Complutense de Madrid
Clasificacion ipc
A61K 31/ 66 A IA61P 33/ 02 A IC07F 9/ 54 A IC07F 9/ 58 A I
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