ES2606168T3 - Compuestos bencil aralquil éter, método para preparar los mismos, compuestos intermedios, uso de dichos compuestos, procedimiento para el tratamiento y/o prevención, composición farmacéutica y medicamento que contiene la misma - Google Patents
Compuestos bencil aralquil éter, método para preparar los mismos, compuestos intermedios, uso de dichos compuestos, procedimiento para el tratamiento y/o prevención, composición farmacéutica y medicamento que contiene la misma Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
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- A—HUMAN NECESSITIES
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A—HUMAN NECESSITIES
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
- C07C22/08—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings containing fluorine
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- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
Compuestos bencil aralquil éteres, caracterizados por ser de fórmula (I):**Fórmula** sus sales, solvatos, ésteres, enantiómeros y/o diastereoisómeros farmacéuticamente aceptables, en la que: Ar es imidazolilo; R1, R2, R4 y R5 son independientemente hidrógeno; R3 es un halógeno; R6 es trifluorometilo o triclorometilo; n es un número entero de 0 a 2; m es 1.
Description
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Babesia, Theileria, Dientamoeba, Giardia, Leishmania, Acanthamoeba, Blastocystis, Anaplasma, Ehrlichia, Trychomonas, Trypanosoma, Giardia, Entamoeba, entre otros.
Los compuestos descritos en la presente invención, así como sus sales, solvatos, ésteres, enantiómeros y/o diastereoisómeros farmacéuticamente aceptables, pueden usarse en la fabricación de un fármaco para el tratamiento y/o prevención de afecciones y/o enfermedades asociadas a microorganismos tales como hongos, bacterias y/o protozoos. Además, los compuestos descritos en la presente invención, así como sus sales, solvatos, profármacos, ésteres, enantiómeros y/o diastereoisómeros farmacéuticamente aceptables pueden usarse en la fabricación de una medicina para la inhibición de la proliferación y/o supervivencia de microorganismos, tales como hongos, bacterias y/o protozoos, particularmente de microorganismos patógenos.
Por lo tanto, la presente invención proporciona una cantidad eficaz de al menos un compuesto descrito en la fórmula
(I) de la presente invención y sus sales, solvatos, ésteres, enantiómeros y/o diastereoisómeros farmacéuticamente aceptables o mezclas del mismo para su uso en el tratamiento y/o prevención de afecciones y/o enfermedades asociadas a microorganismos tales como hongos, bacterias y/o protozoos, por ejemplo, dermatofitos, levaduras, hongos no dermatofitos filamentosos, bacterias Gran negativas y Gran positivas, y protozoos en un mamífero.
La presente invención también proporciona los compuestos de fórmula (I) para su uso en un procedimiento para la inhibición de la proliferación y/o supervivencia de microorganismos, tales como hongos, bacterias y/o protozoos, particularmente microorganismos patógenos.
Por lo tanto, dada su eficacia probada, se considera que los compuestos de fórmula (I) y las sales farmacéuticamente aceptables de los mismos son de interés en terapia, específicamente en el tratamiento y/o la prevención de afecciones y/o enfermedades en individuos asociadas a microorganismos, tales como hongos, bacterias y/o protozoarios. Se entiende por individuo el organismo que representa tanto una unidad fisiológica totalmente independiente como un genotipo único.
Las enfermedades que afectan a los hombres, cuando son causadas por patógenos fúngicos, se denominan micosis. Las micosis pueden clasificarse en tres grupos dependiendo del lugar y la profundidad en la que aparecen en el cuerpo, que son: (i) micosis superficiales: infección sobre la superficie de la piel, uñas, vello, mucosas y/o cabellos; (ii) micosis subcutáneas: causadas por hongos capaces de penetrar en las capas profundas de la piel, tales como tejido subcutáneo, tejido conectivo y tejido óseo; y (iii) micosis sistémicas (o profundas): infecciones fúngicas más severas e invasivas que pueden ser adquiridas por la inhalación de esporas de hongos patógenos que permanecen y crecen en los pulmones o alcanzan el torrente sanguíneo, y que pueden infectar otros órganos internos del organismo.
Las micosis superficiales principales están causadas por hongos dermatofitos y se denominan dermatofitosis. Los ejemplos de dermatofitosis más comunes pueden ser: (i) tiña captis (cuero cabelludo) causada por diversos dermatofitos, tales como M. canis (tiña captis microspórica), T. tonsurans (tiña tonsurante), T. mentagrophytes, E. floccosum, M. gypseum (Querión), T. violaceum, T. schoenleinii (pie de atleta de tiña captis) T. verrucosum, y T. schonleinii (tiña de peines), (ii) tinea barbae (barba) causada por T. rubrum y T. mentagrophytes (iii) tinea corporis (piel lampiña) causada con mayor frecuencia por T. rubrum, T. mentagrohytes y M. kennels, (iv) pie de atleta (pies y manos), causado a menudo por T. rubrum, T. mentagrohytes y E. floccosum (v) tinea cruris (zona inguinal) causada por T. rubrum, T. mentagrohytes y E. floccosum (vi) tiña del oído causada por M. kennels, (vii) imbricate tinea causada por T. concentricum (viii) tiña de la uña (Onicomicosis) causada principalmente por diversos dermatofitos de los géneros Trichophyton, Epidermophyton, rara vez por Microsporum;
Además, los hongos que no son naturalmente patógenos a los humanos pueden desarrollar infecciones oportunistas, secundariamente a otras afecciones preexistentes y debilitantes del sistema inmunológico del huésped. Los principales ejemplos de hongos que causan las infecciones oportunistas son: (i) hongos filamentosos, que pertenecen principalmente a los géneros Aspergillus sp, Fusarium sp, Scedosporium sp, Mucorales y Dematiaceous y (ii) levadura, que pertenecen principalmente a los géneros Candida sp, Cryptococcus sp, Trichosporon sp, Rhodotorula SP, Malassezia sp y Saccharomyces sp.
Los ejemplos de dermatosis clínicamente relevante causada por otros hongos filamentosos oportunistas, pueden ser
(i) pitiriasis versicolor (piel) causada por Malassezia furfur; (ii) foliculitis pitirospórica causada por la infección del hongo Malassezia furfur en los folículos pilosebáceos; (iii) tiña negra (palmas de las manos o puntas de los dedos), causada por Cladosporium werneckii (iv) piedra negra (pelo) causada por el hongo Piedraia hortai.
Además, también se pueden citar ejemplos de las enfermedades causadas por los hongos levaduriformes oportunistas, tales como (i) tricosporonosis, causada por el hongo levaduriforme Trichosporon beigelii subdividida en piedra blanca (pelo) y tricosporonosis génito-inguinal (erupción en la zona génito-inguinal), (ii) candidiasis, causada por las levaduras del género Candida sp, siendo el más frecuente C. albicans, pero también puede encontrarse en las especies C. tropicalis, C. parapsilosis, C. guilliermondii y las candidiasis se pueden subdividir en candidiasis oral, candidiasis vulvo-vaginal, candidiasis balanoprepucial, candidiasis intertriginosa, candidiasis mucocutánea y candidiasis folicular.
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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BR0904249 | 2009-08-28 | ||
BRPI0904249-0A BRPI0904249B1 (pt) | 2009-08-28 | 2009-08-28 | Compostos éteres aralquil benzílicos, processo de preparação dos mesmos, uso dos referidos compostos, composição farmacêutica |
PCT/BR2010/000276 WO2011022798A1 (pt) | 2009-08-28 | 2010-08-27 | Compostos éteres aralquil benzílicos, processo de preparação dos mesmos, compostos intermediários, uso dos referidos compostos, método de tratamento e/ou prevenção, composição farmacêutica e medicamento contendo os mesmos |
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ES2606168T3 true ES2606168T3 (es) | 2017-03-23 |
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ES10811042.0T Active ES2606168T3 (es) | 2009-08-28 | 2010-08-27 | Compuestos bencil aralquil éter, método para preparar los mismos, compuestos intermedios, uso de dichos compuestos, procedimiento para el tratamiento y/o prevención, composición farmacéutica y medicamento que contiene la misma |
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Country | Link |
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US (1) | US8975289B2 (es) |
EP (1) | EP2471781B1 (es) |
JP (1) | JP5718334B2 (es) |
KR (1) | KR101765752B1 (es) |
CN (1) | CN102625800A (es) |
AR (1) | AR078115A1 (es) |
AU (1) | AU2010286266B2 (es) |
BR (1) | BRPI0904249B1 (es) |
CA (1) | CA2771044C (es) |
CL (1) | CL2012000463A1 (es) |
DK (1) | DK2471781T3 (es) |
ES (1) | ES2606168T3 (es) |
HU (1) | HUE032199T2 (es) |
IL (1) | IL218044A (es) |
IN (1) | IN2012DN00611A (es) |
MX (1) | MX2012002276A (es) |
PE (1) | PE20120921A1 (es) |
PL (1) | PL2471781T3 (es) |
PT (1) | PT2471781T (es) |
RU (1) | RU2548009C2 (es) |
SG (1) | SG178298A1 (es) |
UA (1) | UA108479C2 (es) |
WO (1) | WO2011022798A1 (es) |
ZA (1) | ZA201201442B (es) |
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CN102579829B (zh) * | 2012-03-06 | 2013-09-18 | 康莉 | 一种治疗牛放线菌病的中药组合物及其制备方法 |
CN104016837B (zh) * | 2014-05-26 | 2016-08-24 | 武汉有机实业有限公司 | 4,4’-二甲基二苄基醚的制备方法 |
RU2603622C1 (ru) * | 2015-06-25 | 2016-11-27 | Федеральное государственное бюджетное научное учреждение "Прикаспийский зональный научно-исследовательский ветеринарный институт" | Комплексный метод лечения тейлериоза мелкого рогатого скота |
CN108047147A (zh) * | 2017-12-08 | 2018-05-18 | 长江大学 | 一类三唑类化合物以及作为杀菌剂的用途 |
KR101983575B1 (ko) * | 2017-12-21 | 2019-06-03 | 대한민국 | 신균주 세라토바시디움 속 js1289 및 이의 용도 |
US20220267280A1 (en) * | 2019-08-16 | 2022-08-25 | Purdue Research Foundation | Small molecule stimulators of the core particle of the proteasome |
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GB1170188A (en) | 1967-09-15 | 1969-11-12 | Bayer Ag | N-trityl-imidazoles and salts and uses thereof |
SU557755A3 (ru) * | 1968-08-19 | 1977-05-05 | Янссен Фармасьютика Н.В. (Фирма) | Способ получени производных имидазола |
DE2333354C2 (de) * | 1973-06-30 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | 2-Aryloxy-2-(imidazol-1-yl)-äthanole sowie deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
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AU2010286266A1 (en) | 2012-04-05 |
BRPI0904249B1 (pt) | 2018-03-06 |
SG178298A1 (en) | 2012-03-29 |
JP5718334B2 (ja) | 2015-05-13 |
US20120196908A1 (en) | 2012-08-02 |
ZA201201442B (en) | 2012-10-31 |
AR078115A1 (es) | 2011-10-12 |
BRPI0904249A2 (pt) | 2011-05-17 |
RU2012110925A (ru) | 2013-10-10 |
CL2012000463A1 (es) | 2012-09-21 |
CA2771044A1 (en) | 2011-03-03 |
IL218044A (en) | 2017-02-28 |
KR20120050490A (ko) | 2012-05-18 |
UA108479C2 (en) | 2015-05-12 |
DK2471781T3 (da) | 2017-01-02 |
JP2013503111A (ja) | 2013-01-31 |
HUE032199T2 (en) | 2017-08-28 |
KR101765752B1 (ko) | 2017-08-07 |
PL2471781T3 (pl) | 2017-08-31 |
MX2012002276A (es) | 2012-04-19 |
IN2012DN00611A (es) | 2015-06-12 |
PE20120921A1 (es) | 2012-08-01 |
CA2771044C (en) | 2017-07-04 |
PT2471781T (pt) | 2016-12-15 |
RU2548009C2 (ru) | 2015-04-10 |
IL218044A0 (en) | 2012-04-30 |
EP2471781A1 (en) | 2012-07-04 |
AU2010286266B2 (en) | 2015-02-12 |
CN102625800A (zh) | 2012-08-01 |
US8975289B2 (en) | 2015-03-10 |
WO2011022798A1 (pt) | 2011-03-03 |
EP2471781B1 (en) | 2016-09-07 |
EP2471781A4 (en) | 2013-01-23 |
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