AR068064A1 - DERIVATIVES OF OXAZOLIDINONA, ITS COMPOSITIONS AND USES - Google Patents

DERIVATIVES OF OXAZOLIDINONA, ITS COMPOSITIONS AND USES

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Publication number
AR068064A1
AR068064A1 ARP080103743A ARP080103743A AR068064A1 AR 068064 A1 AR068064 A1 AR 068064A1 AR P080103743 A ARP080103743 A AR P080103743A AR P080103743 A ARP080103743 A AR P080103743A AR 068064 A1 AR068064 A1 AR 068064A1
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Argentina
Prior art keywords
alkyl
optionally substituted
cyano
halogens
hydroxyls
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ARP080103743A
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Spanish (es)
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Pfizer Prod Inc
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Publication of AR068064A1 publication Critical patent/AR068064A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18Oxygen atoms
    • C07D263/20Oxygen atoms attached in position 2
    • C07D263/22Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Cardiology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Uso de tales compuestos para elevar ciertos niveles lipídicos plasmáticos, incluyendo el colesterol de lipoproteínas de alta densidad y para disminuir otros determinados niveles lipídicos plasmáticos, tales como el colesterol LDL y triglicéridos y por consiguiente para tratar enfermedades que se agravan por bajos niveles de colesterol HDL y/o altos niveles de colesterol LDL y triglicéridos, tales como aterosclerosis y enfermedades cardiovasculares en algunos mamíferos, incluyendo seres humanos. Reivindicacion 1: Un compuesto de formula (1) o una sal farmacéuticamente aceptable de dicho compuesto en la que A es una de las estructuras del grupo de formulas (2); B es -OR6 o-NR7R8; M y J son cada uno independientemente CH2 o un enlace en el que al menos uno de M y J son CH2; W es hidrogeno o una cadena lineal o ramificada completamente saturada, parcialmente insaturada o completamente insaturada que tiene de 1 a 6 átomos de carbono estando cada átomo de carbono de dicha cadena opcionalmente sustituido por un heteroátomo seleccionado de nitrogeno, oxigeno o azufre. y estando dicho átomo de carbono de dicha cadena opcionalmente mono-, di- o trisustituido con amino, halogeno, ciano, alquilo C1-6, alcoxilo C1-6, hidroxilo u oxo y estando dicho átomo de nitrogeno de dicha cadena opcionalmente mono- o disustituido con alquilo C1-6, ciano u oxo y estando dicho átomo de azufre opcionalmente sustituido con uno o dos oxo; R1, R2, R3 y R4 son cada uno independientemente hidrogeno, halogeno, ciano, hidroxilo, nitro, (alquilo C1-6 opcionalmente sustituido con uno a nueve halogenos, uno o dos hidroxilos, uno o dos alcoxilos C1-6, uno o dos aminos, uno o dos nitros, ciano, oxo, carboxilo), (alcoxilo C1-6 opcionalmente sustituido con uno a nueve halogenos, uno a dos hidroxilos, o ciano) o (alquiltio C1-6 opcionalmente sustituido con uno a nueve halogenos, uno a dos hidroxilos, o ciano); o R1 y R2 o R2 y R3 se toman opcionalmente juntos para formar un anillo de 5 a 7 miembros parcialmente insaturado a completamente insaturado, estando cada átomo de carbono de dicho anillo opcionalmente sustituido con un átomo de oxígeno, no estando los átomos de oxígeno conectados entre sí, estando dicho anillo opcionalmente mono-, di-, tri- o tetra-sustituido con halogeno, y opcionalmente mono- o disustituido con hidroxilo, amino, nitro, ciano, oxo, carboxilo, (alquilo C1-6 opcionalmente sustituido con uno a nueve halogenos, uno o dos hidroxilos, uno o dos alcoxilos C1-6, uno o dos aminos, uno o dos nitros, ciano, oxo o carboxilo), o (alcoxilo C1-6 opcionalmente sustituido con uno a nueve halogenos, uno o dos hidroxilos, o ciano); R5 es hidrogeno o alquilo C1-6 opcionalmente sustituido con uno a nueve halogenos; R6 es -alquil C1-6-NR9R10, -alquil C0-6-CO-NR9R10, -alquil C0-6-COOR13. -alquil C1-6-NR10-alquil C0-6-CO-O-R13, -alquil C1-6-NR10-alquil C0-6-CO-R13, -alquil C1-6-NR10-alquil C0-6-SO2R13, -alquil C1-6-O-CO-NR9R10, -alquenil C2-6-CO-O-R13, -alquil C1-6-arilo, alquil C1-6-heteroarilo. -alquil C1-6-O-arilo, -alquil C1-6-O-heteroarilo, -alquil C0-6-heterociclo, -alquil C0-6-cicloalquilo C3-6, -alquil C0-6-cicloalquenilo C3-6, alquinilo C2-6, alquenilo C2-6, alquilo C1-6 o -CO-alquilo C1-6, estando dichos grupos arilo, heteroarilo, heterociclo, cicloalquenilo, cicloalquilo, alquinilo, alquenilo y alquilo cada uno opcionalmente sustituido independientemente con uno a nueve halogenos, uno o dos hidroxilos, de uno a tres alquilos C1-6, de uno a tres haloalquilos C1-6, de uno a tres alcoxilos C1-6, de uno a tres haloalcoxilos C1-6, uno o dos aminos, uno o dos nitros, ciano, oxo o carboxilo; R7 y R8 son cada uno independientemente hidrogeno, -alquil C1-6-NR9R10, -alquil C0-6-CO-NR9R10, -alquil C0-6-CO-OR13, -alquil C1-6-NR10-alquil C0-6-CO-O-R13, -alquil C1-6-NR10-alquil C0-6-CO-R13, -alquil C1-6-NR10-alquil C0-6-SO2-R13, -alquil C1-6-O-CO-NR9R10, -alquenil C2-6-CO-O-R13, -alquil C0-6-arilo, -alquil C0-6-heteroarilo, -alquil C1-6-O-arilo, -alquil C1-6-O-heteroarilo, -alquil C0-6-heterociclo, -alquil C0-6-cicloalquilo C3-6, -alquil C0-6-cicloalquenilo C3-6, alquinilo C2-6, alquenilo C2-6, alquilo C1-6, ciano, o -CO-alquilo C1-6 estando dichos sustituyentes arilo, heteroarilo, heterociclo, cicloalquenilo, cicloalquilo, alquinilo, alquenilo y alquilo cada uno opcionalmente sustituido independientemente con uno a nueve halogenos, uno o dos hidroxilos, de uno a tres alquilos C1-6, de uno a tres haloalquilos C1-6, de uno tres alcoxilos C1-6, de uno a tres haloalcoxilos C1-6, uno o dos aminos, uno o dos nitros, ciano, oxo o carboxilo; o R7 y R8 se toman opcionalmente juntos para formar un anillo de 3 a 8 miembros mono- o bicíclico completamente saturado o parcialmente insaturado que tiene opcionalmente uno o dos heteroátomos seleccionados de oxígeno, nitrogeno y azufre, estando el anillo opcionalmente mono-, di- o trisustituido con R14; R9 y R10 son cada uno independientemente hidrogeno, arilo o alquilo C1-6 opcionalmente sustituido con uno a nueve halogenos; R11 y R12 son cada uno independientemente hidrogeno, una cadena completamente saturada, parcialmente insaturada o completamente insaturada que tiene 1, 2 o 3 átomos de carbono, o un anillo mono- o bicíclico completamente saturado, parcialmente insaturado o completamente insaturado que tiene de 3 a 10 átomos de carbono, siendo dicho anillo opcionalmente bicíclico, y estando cada átomo de carbono de dicho anillo opcionalmente sustituido por un heteroátomo seleccionado de nitrogeno. oxígeno o azufre, y estando dicho átomo de carbono de dicha cadena o dicho anillo opcionalmente mono, di- o trisustituido con R14 y estando dicho átomo de nitrogeno de dicho anillo opcionalmente sustituido con R15 y no estando R11 y R12 unidos al carbono de Y en un heteroátomo, y no siendo R11 y R12 ambos hidrogeno, con la condicion de que cuando B es NR7R8, entonces R12 es H; o R11 y R12 se toman opcionalmente juntos para formar cicloalquilo C4-7 opcionalmente mono-, di- o trisustituido con R14; R13 es hidrogeno, arilo, o alquilo C1-6 opcionalmente substituido con uno a nueve halogenos; cada R14 es independientemente -alquil C0-6-NR9R10, -alquil C0-6-CO-NR9R10, -alquil C0-6-CO-OR10, -O-alquil C0-6-CO-O-R10, halogeno, alquilo C1-6, hidroxilo, alcoxilo C1-6, ciano, oxo o -CO-alquilo C1-6, estando dichos grupos alquilo y alcoxilo cada uno opcionalmente substituido independientemente con uno a nueve halogenos, uno o dos hidroxilos, de uno a tres alquilos C1-6, de uno a tres haloalquilos C1-6, de uno a tres alcoxilos C1-6, de uno a tres haloalcoxilos C1-6, uno o dos aminos. uno o dos nitros, ciano, oxo o carboxilo; cada R15 es independientemente alquil C1-6-NR9R10, -alquil C0-6-CO-NR9R10, -alquil C0-6-CO-OR10, o -CO-alquilo C1-6, estando dichos grupos alquilo cada uno opcionalmente sustituido independientemente con uno a nueve halogenos, uno o dos hidroxilos, de uno a tres alquilos C1-6, de uno a tres haloalquilos C1-6, de uno a tres alcoxilos C1-6, de uno a tres haloalcoxilos C1-6, uno o dos aminos, uno o dos nitros, ciano, oxo o carboxilo; cada R16 es independientemente halogeno, nitro, ciano, hidroxilo, oxo, carboxilo. alcoxicarbonilo C1-6, (alquilo C1-6 opcionalmente substituido con uno a nueve halogenos o uno o dos hidroxilos), (alcoxilo C1-6 opcionalmente substituido con uno a nueve halogenos o uno o dos hidroxilos), o (alquiltio C1-6 opcionalmente sustituido con uno a nueve halogenos o uno o dos hidroxilos); y n es 0, 1, 2, 3 o 4.Use of such compounds to raise certain plasma lipid levels, including high-density lipoprotein cholesterol and to lower certain other plasma lipid levels, such as LDL cholesterol and triglycerides and therefore to treat diseases that are aggravated by low levels of HDL cholesterol. and / or high levels of LDL cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases in some mammals, including humans. Claim 1: A compound of formula (1) or a pharmaceutically acceptable salt of said compound in which A is one of the structures of the group of formulas (2); B is -OR6 or-NR7R8; M and J are each independently CH2 or a link in which at least one of M and J are CH2; W is hydrogen or a fully saturated, partially unsaturated or completely unsaturated linear or branched chain having 1 to 6 carbon atoms, each carbon atom of said chain being optionally substituted by a heteroatom selected from nitrogen, oxygen or sulfur. and said carbon atom of said chain being optionally mono-, di- or trisubstituted with amino, halogen, cyano, C1-6 alkyl, C1-6 alkoxy, hydroxyl or oxo and said nitrogen atom of said chain being optionally mono- or disubstituted with C1-6 alkyl, cyano or oxo and said sulfur atom being optionally substituted with one or two oxo; R1, R2, R3 and R4 are each independently hydrogen, halogen, cyano, hydroxyl, nitro, (C1-6 alkyl optionally substituted with one to nine halogens, one or two hydroxyls, one or two C1-6 alkoxyls, one or two aminos, one or two nitros, cyano, oxo, carboxyl), (C1-6 alkoxy optionally substituted with one to nine halogens, one to two hydroxyls, or cyano) or (C1-6 alkylthio optionally substituted with one to nine halogens, one to two hydroxyls, or cyano); or R1 and R2 or R2 and R3 are optionally taken together to form a 5 to 7-membered ring partially unsaturated to completely unsaturated, each carbon atom of said ring being optionally substituted with an oxygen atom, the oxygen atoms not being connected each other, said ring being optionally mono-, di-, tri- or tetra-substituted with halogen, and optionally mono- or disubstituted with hydroxyl, amino, nitro, cyano, oxo, carboxyl, (C1-6 alkyl optionally substituted with one to nine halogens, one or two hydroxyls, one or two C1-6 alkoxyls, one or two aminos, one or two nitros, cyano, oxo or carboxyl), or (C1-6 alkoxy optionally substituted with one to nine halogens, one or two hydroxyls, or cyano); R5 is hydrogen or C1-6 alkyl optionally substituted with one to nine halogens; R6 is -C1-6-NR9R10 alkyl, -C0-6-CO-NR9R10 alkyl, -C0-6-COOR13 alkyl. -C1-6-NR10-C0-6-CO-O-R13 alkyl, -C1-6-NR10-C0-6-CO-R13 alkyl, -C1-6-NR10-C0-6-SO2R13 alkyl , -C 1-6 alkyl-O-CO-NR9R10, -C 2-6 alkenyl-CO-O-R 13, -C 1-6 alkyl-aryl, C 1-6 alkyl-heteroaryl. -C 1-6 alkyl-O-aryl, -C 1-6 alkyl-O-heteroaryl, -C 0-6 alkyl-heterocycle, -C 0-6 alkyl-C 3-6 cycloalkyl, -C 0-6 alkyl-C 3-6 cycloalkenyl, C2-6 alkynyl, C2-6 alkenyl, C1-6 alkyl or -CO-C1-6 alkyl, said aryl, heteroaryl, heterocycle, cycloalkenyl, cycloalkyl, alkynyl, alkenyl and alkyl groups each optionally independently substituted with one to nine halogens, one or two hydroxyls, one to three C1-6 alkyls, one to three C1-6 haloalkyls, one to three C1-6 alkoxyls, one to three C1-6 haloalkoxyls, one or two aminos, one or two nitros, cyano, oxo or carboxyl; R7 and R8 are each independently hydrogen, -C1-6-NR9R10 alkyl, -C0-6-CO-NR9R10 alkyl, -C0-6-CO-OR13 alkyl, -C1-6-NR10-C0-6 alkyl CO-O-R13, -C 1-6 alkyl-NR10-C0-6-CO-R13 alkyl, -C 1-6 alkyl-NR10-C0-6-SO2-R13 alkyl, -C 1-6 alkyl-O-CO- NR9R10, -C2-6-CO-O-R13 alkyl, -C0-6-aryl alkyl, -C0-6-heteroaryl alkyl, -C 1-6 alkyl-O-aryl, -C 1-6 alkyl-O-heteroaryl, -C0-6-heterocycle, -C0-6 alkyl-C3-6 cycloalkyl, -C0-6 alkyl-C3-6 cycloalkenyl, C2-6 alkynyl, C2-6 alkenyl, C1-6 alkyl, cyano, or -CO - C1-6 alkyl, said substituents being aryl, heteroaryl, heterocycle, cycloalkenyl, cycloalkyl, alkynyl, alkenyl, and alkyl each optionally substituted independently with one to nine halogens, one or two hydroxyls, one to three C1-6 alkyls, one to three C1-6 haloalkyls, one to three C1-6 alkoxyls, one to three C1-6 haloalkoxyls, one or two aminos, one or two nitros, cyano, oxo or carboxyl; or R7 and R8 are optionally taken together to form a fully saturated or partially unsaturated mono- or bicyclic 3- to bicyclic ring having optionally one or two heteroatoms selected from oxygen, nitrogen and sulfur, the ring being optionally mono-, di- or trisubstituted with R14; R9 and R10 are each independently hydrogen, aryl or C1-6 alkyl optionally substituted with one to nine halogens; R11 and R12 are each independently hydrogen, a completely saturated, partially unsaturated or completely unsaturated chain having 1, 2 or 3 carbon atoms, or a fully saturated, partially unsaturated or completely unsaturated mono- or bicyclic ring having 3 to 3 10 carbon atoms, said ring being optionally bicyclic, and each carbon atom of said ring being optionally substituted by a heteroatom selected from nitrogen. oxygen or sulfur, and said carbon atom of said chain or said ring being optionally mono, di- or trisubstituted with R14 and said nitrogen atom of said ring being optionally substituted with R15 and R11 and R12 not being attached to the carbon of Y in a heteroatom, and R11 and R12 are not both hydrogen, with the proviso that when B is NR7R8, then R12 is H; or R11 and R12 are optionally taken together to form optionally mono-, di- or trisubstituted C4-7 cycloalkyl with R14; R13 is hydrogen, aryl, or C1-6 alkyl optionally substituted with one to nine halogens; each R14 is independently -C0-6-NR9R10 alkyl, -C0-6-CO-NR9R10 alkyl, -C0-6-CO-OR10 alkyl, -O-C0-6-CO-O-R10 alkyl, halogen, C1 alkyl -6, hydroxy, C1-6 alkoxy, cyano, oxo or -CO-C1-6 alkyl, said alkyl and alkoxy groups being each optionally substituted independently with one to nine halogens, one or two hydroxyls, one to three C1 alkyls -6, one to three C1-6 haloalkyls, one to three C1-6 alkoxyls, one to three C1-6 haloalkoxyls, one or two aminos. one or two nitros, cyano, oxo or carboxyl; each R15 is independently C1-6-NR9R10 alkyl, -C0-6-CO-NR9R10 alkyl, -C0-6-CO-OR10 alkyl, or -CO-C1-6 alkyl, said alkyl groups each being optionally substituted independently with one to nine halogens, one or two hydroxyls, one to three C1-6 alkyls, one to three C1-6 haloalkyls, one to three C1-6 alkoxyls, one to three C1-6 haloalkoxyls, one or two aminos , one or two nitros, cyano, oxo or carboxyl; Each R16 is independently halogen, nitro, cyano, hydroxyl, oxo, carboxyl. C1-6 alkoxycarbonyl, (C1-6 alkyl optionally substituted with one to nine halogens or one or two hydroxyls), (C1-6 alkoxy optionally substituted with one to nine halogens or one or two hydroxyls), or (C1-6 alkylthio optionally substituted with one to nine halogens or one or two hydroxyls); and n is 0, 1, 2, 3 or 4.

ARP080103743A 2007-08-30 2008-08-28 DERIVATIVES OF OXAZOLIDINONA, ITS COMPOSITIONS AND USES AR068064A1 (en)

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EP2612669A4 (en) 2010-08-31 2014-05-14 Snu R&Db Foundation Use of the fetal reprogramming of a ppar agonist
KR20190025737A (en) 2011-07-08 2019-03-11 노파르티스 아게 Method of treating atherosclerosis in high triglyceride subjects
WO2014111953A1 (en) * 2013-01-17 2014-07-24 Glenmark Pharmaceuticals Limited; Glenmark Generics Limited Process for preparation of anacetrapib and intermediates thereof
TW201609661A (en) 2013-12-05 2016-03-16 拜耳作物科學公司 N-cycloalkyl-N-{[2-(1-substitutedcycloalkyl)phenyl]methylene}-(thio)carboxamide derivatives
CN110157711B (en) * 2019-02-01 2023-10-24 大连大学 Method for cloning full-length segment of coding region of human srebp1 gene

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US5631365A (en) * 1993-09-21 1997-05-20 Schering Corporation Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents
AU2006332681B2 (en) * 2005-12-30 2011-04-07 Merck Sharp & Dohme Corp. 1, 3-oxazolidin-2-one derivatives useful as CETP inhibitors
US7781426B2 (en) * 2005-12-30 2010-08-24 Merck Sharp & Dohme Corp. CETP inhibitors

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