AR065374A1 - 1, 1-DIOXO-1-TIA-5, 10-DIAZADIBENZOCICLOHEPTENOS USEFUL AS INHIBITORS OF THE VIRUSES OF HEPATITIS C, METHODS FOR THEIR PREPARATION, A PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND ITS USE IN THE MANUFACTURE OF AN INHIBITION REPLACEMENT MEDICATION HCV - Google Patents

1, 1-DIOXO-1-TIA-5, 10-DIAZADIBENZOCICLOHEPTENOS USEFUL AS INHIBITORS OF THE VIRUSES OF HEPATITIS C, METHODS FOR THEIR PREPARATION, A PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND ITS USE IN THE MANUFACTURE OF AN INHIBITION REPLACEMENT MEDICATION HCV

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Publication number
AR065374A1
AR065374A1 ARP080100660A ARP080100660A AR065374A1 AR 065374 A1 AR065374 A1 AR 065374A1 AR P080100660 A ARP080100660 A AR P080100660A AR P080100660 A ARP080100660 A AR P080100660A AR 065374 A1 AR065374 A1 AR 065374A1
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Argentina
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formula
alkyl
optionally substituted
compound
aryl
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ARP080100660A
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Spanish (es)
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Tibotec Pharm Ltd
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Publication of AR065374A1 publication Critical patent/AR065374A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Virology (AREA)
  • Veterinary Medicine (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Prosesos para preparar dichos compuestos, composiciones farmaceuticas que los contiene y su uso en terapia de VHC. Reivindicacion 1: Un compuesto que tiene la formula (1):y sus estereoisomeros, profármacos, tautomeros, racémicos, sales, hidratos osolvatos, donde R1a es hidrogeno, hidroxi, amino, alcoxi C1-6, halo o alquilo C1-6 opcionalmente sustituido con hidroxilo; R1b es hidrogeno, hidroxi, amino, alcoxi C1-6, -O-CH2-tiazolilo, halo, trifluorometilo, o alquilo C1-6 opcionalmentesustituido con ciano; R2 es hidrogeno, -C(=O)-R5, -C(=O)-C(=O)-R5, -C(=O)-OR6, o -C(=O)-NR7aR7b; R3 es alquilo C1-6 opcionalmente sustituido con cicloalquilo C3-7, arilo, o Het; cicloalquilo C3-7 arilo; o Het; cada R4a y R4b es, independientemente,hidrogeno, alquilo C1-6, alquenilo C2-6 o ambos R4a y R4b junto con el átomo de carbono del anillo tricíclico al cual estan unidos pueden formar un C3-7 cicloalquilo o un oxetanilo; R5 es alquilo C1-6 opcionalmente sustituido con uno o dossustituyentes seleccionados de halo, C3-7 cicloalquilo, fenilalquiltio C1-6, ciano, polihalo-alquilo C1-6, oxo, -OR9, -C(O)-Het, -C(=O)-OR6, -C(=O)-OH, -C(=O)-NR7aR7b, -C(=O)-NH-S(=O)2-R8, -NR7aR7b, -S(=O)2-arilo, arilo, y Het; alquenilo C2-6opcionalmente sustituido con arilo; polihalo-alquilo C1-6 cicloalquilo C3-7; arilo; o Het; R6 es arilo o alquilo C1-6 opcionalmente sustituido con -OR9, -C(=O)-OR9, -C(=O)-NR7aR7b, -C(=O)-NH-S(=O)2-R8, arilo, o Het; cada R7a y R7b es,independientemente, hidrogeno; alquilo C1-6 opcionalmente sustituido con uno o dos sustituyentes seleccionados de -OR9, mono- o dialquilamino C1-6, -C(=O)-OR9, -C(=O)-NH2, -C(=O)-NH-C1-6 alquilo, -C(=O)-NH-hidroxialquilo C1-6, -C(=O)-Het, C3-7cicloalquilo, arilo, y Het; alquenilo C2-6; cicloalquilo C3-7 opcionalmente sustituido con hídroxi; arilo; o Het; R8 es alquilo C1-6 cicloalquilo C3-7, di(alquilo C1-3)amino, o arilo; R9 es hidrogeno; alquilo C1-6 opcionalmente sustituido con uno,dos o tres sustituyentes cada uno independientemente seleccionado de halo, hidroxilo, cicloalquenilo C3-7, cicloalquilo C3-7, ciano, alcoxí C1-6, fenilo, o Het, donde el fenilo puede estar opcionalmente sustituido con halo, hidroxilo, alcoxi C1-6,alcoxi C1-6. alcoxi C1-6 alquilo C1-6, nitro, o amino; alquenilo C2-6 opcionalmente sustituido con uno o dos sustituyentes seleccionados de halo y polihalo-alquilo C1-6; alquinilo C2-6; cicloalquenilo C3-7; o fenilo opcionalmente sustituido con unoo dos sustituyentes seleccionados de hidroxilo, alcoxi C1-6, halo, polihalo-alquilo C1-6, amino, nitro, C1-6 alquilo, y fenilo; Arilo como un grupo o parte de un grupo es fenilo, naftilo, indanilo, o 1,2,3,4-tetrahidronaftilo, cada uno de los cualespuede estar opcionalmente sustituido con uno, dos, tres o cuatro sustituyentes cada uno independientemente seleccionado del grupo integrado por cicloalquilo C3-7, fenilalquilo C1-6, fenilpolihalo-alquilo C1-6, fenilalquiloxi C1-6, halo, polihalo-alquilo C1-6, ciano, alquilo C1-6, polihalo-alcoxi C1-6, -OR9, -C(=O)OH, alquilcarbonilo C1-6, alquiltio C1-6 alquilsulfonilo C1-6, -S(=O)2NH2, y pirrolilo, donde el fenilo puede estar opcionalmente sustituido con halo; o dos sustituyentes sobre elanillo arilo pueden formar -O-CH2-O- o a -O-C(CH3)2-CH2-; Het como un grupo o parte de un grupo es un anillo mono- o biciclico, saturado, parcialmente insaturado o completamente insaturado de 5 a 12 miembros que contienen 1 a 4 heteroátomos cada unoindependientemente seleccionado de nitrogeno, oxígeno y azufre, estando opcionalmente condensado con un anillo de benceno, y donde el grupo Het en su totalidad puede estar opcionalmente sustituido con uno o dos sustituyentes cada unoindependientemente seleccionado del grupo integrado por halo; polihalo-alquilo C1-6 C1-6alquiltio, oxo; -OR9; -NR10aR10b; -CN; alquilo C1-6 opcionalmente sustituido con -OR9, -CN, -NR10aR10b, o fenilo;-C(=O)-NH2;-C(=O)-fenilo; C3-7cicloalquilo;fenilo opcionalmente sustituido con alcoxi C1-6; morfolinilo; pirrolidinilo; pirrolilo; furanoílo; tetrazolilo; y tiofenilo; y cada R10a y R10b es, independientemente, hidrogeno, alquilo C1-6, arilalquilo C1-6, o R10a y R10b, junto con el nitrogenoal cual están unidos, pueden formar un monociclo de 5 a 8 miembros saturado, parcialmente insaturado, o completamente insaturado, donde dicho monociclo contiene opcionalmente un heteroátomo adicional seleccionado del grupo integrado por oxígeno,azufre y nitrogeno, y donde los miembros monociclo restantes son átomos de carbono; donde dicho monociclo puede estar opcionalmente sustituido sobre cualquier átomo de carbono con uno o dos sustituyentes cada uno independientemente seleccionado dehalo, C1-6alquilo, hidroxi, u oxo. Reivindicacion 22: Un proceso para la preparacion de un compuesto de acuerdo con cualquiera de las reivindicaciones 1-12 que tiene la formula (I-8), que comprende los pasos de hacer reaccionar un compuesto deformula (I-2) con un compuesto de formula (I-4) obteniendo de este modo un compuesto de formula (I-5), y hacer reaccionar un compuesto de formula (I-5) con un aldehído de formula (I-7); opcionalmente en presencia de un ácido, obteniendo de este modoun compuesto de formula (I-8), donde R1a, R1b, R4a , R4b, y R3 tienen el mismo significado que en cualquiera de las reivindicaciones 1-12. Reivindicacion 23: Un proceso para la preparacion de un compuesto de acuerdo con cualquiera de lasreivindicaciones 1-12 que tiene la formula (I-9), que comprende el paso de acilar un compuesto de formula (I-8) con un ácido o un ácido activado obteniendo de este modo un compuesto de formula (1) que tiene la formula (I-9) donde R1a, R1b, R4a R4b,R3 y R5 tienen el mismo significado que en cualquiera de las reivindicaciones 1-12. Reivindicacion 24: Un proceso para la preparacion de un compuesto de acuerdo con cualquiera de las reivindicaciones 1-12 que tiene la formula (I-10), que comprendelos pasos de hacer reaccionar un compuesto de formula (I-8) con un isocianato de formula (l-8a) obteniendo de este modo un compuesto de formula (I-10) siendo R7b hidrogeno, o hacer reaccionar un compuesto de formula (I-8) con fosgeno o unequivalente de fosgeno de formula (I-8b), donde LG representa un grupo saliente, seguido del tratamiento con una amina de formula (l-8c) obteniendo de este modo un compuesto de formula (I-10), donde R1a, R1b, R4a, R4b, R3, R7a y R7b tienen el mismosignificado que en cualquiera de las reivindicaciones 1-12. Reivindicacion 25: Un proceso para la preparacion de un compuesto de acuerdo con las reivindicaciones 1-12 que tiene la formula (I-11), que comprende el paso de hacer reaccionar uncompuesto de formula (I-8) con un cloroformiato de formula (l-8d) en presencia de una base, en un solvente inerte obteniendo de esteProgress to prepare said compounds, pharmaceutical compositions containing them and their use in HCV therapy. Claim 1: A compound having the formula (1): and its stereoisomers, prodrugs, tautomers, racemic, salts, osolvate hydrates, wherein R1a is hydrogen, hydroxy, amino, C1-6 alkoxy, halo or C1-6 alkyl optionally substituted with hydroxyl; R1b is hydrogen, hydroxy, amino, C1-6 alkoxy, -O-CH2-thiazolyl, halo, trifluoromethyl, or C1-6 alkyl optionally substituted with cyano; R2 is hydrogen, -C (= O) -R5, -C (= O) -C (= O) -R5, -C (= O) -OR6, or -C (= O) -NR7aR7b; R3 is C1-6 alkyl optionally substituted with C3-7 cycloalkyl, aryl, or Het; C3-7 cycloalkyl aryl; or Het; each R4a and R4b is independently hydrogen, C1-6 alkyl, C2-6 alkenyl or both R4a and R4b together with the carbon atom of the tricyclic ring to which they are attached can form a C3-7 cycloalkyl or an oxetanyl; R5 is C1-6 alkyl optionally substituted with one or two substituents selected from halo, C3-7 cycloalkyl, C1-6 phenylalkylthio, cyano, polyhalo-C1-6 alkyl, oxo, -OR9, -C (O) -Het, -C (= O) -OR6, -C (= O) -OH, -C (= O) -NR7aR7b, -C (= O) -NH-S (= O) 2-R8, -NR7aR7b, -S (= O) 2-aryl, aryl, and Het; C2-6 alkenyl optionally substituted with aryl; polyhalo-C 1-6 alkyl C 3-7 cycloalkyl; aryl; or Het; R6 is aryl or C1-6 alkyl optionally substituted with -OR9, -C (= O) -OR9, -C (= O) -NR7aR7b, -C (= O) -NH-S (= O) 2-R8, aryl, or het; each R7a and R7b is independently hydrogen; C1-6 alkyl optionally substituted with one or two substituents selected from -OR9, mono- or C1-6 dialkylamino, -C (= O) -OR9, -C (= O) -NH2, -C (= O) -NH -C1-6 alkyl, -C (= O) -NH-C1-6 hydroxyalkyl, -C (= O) -Het, C3-7cycloalkyl, aryl, and Het; C2-6 alkenyl; C3-7 cycloalkyl optionally substituted with hydroxy; aryl; or Het; R 8 is C 1-6 alkyl C 3-7 cycloalkyl, di (C 1-3 alkyl) amino, or aryl; R9 is hydrogen; C1-6 alkyl optionally substituted with one, two or three substituents each independently selected from halo, hydroxy, C3-7 cycloalkenyl, C3-7 cycloalkyl, cyano, C1-6 alkoxy, phenyl, or Het, where the phenyl may optionally be substituted with halo, hydroxyl, C1-6 alkoxy, C1-6 alkoxy. C1-6 alkoxy C1-6 alkyl, nitro, or amino; C2-6 alkenyl optionally substituted with one or two substituents selected from halo and polyhalo-C1-6 alkyl; C2-6 alkynyl; C3-7 cycloalkenyl; or phenyl optionally substituted with one or two substituents selected from hydroxyl, C1-6 alkoxy, halo, polyhalo-C1-6 alkyl, amino, nitro, C1-6 alkyl, and phenyl; Aryl as a group or part of a group is phenyl, naphthyl, indanyl, or 1,2,3,4-tetrahydronaphthyl, each of which may be optionally substituted with one, two, three or four substituents each independently selected from the group composed of C3-7 cycloalkyl, C1-6 phenylalkyl, C1-6 alkyl phenylpolylo, C1-6 phenylalkyl, halo, polyhalo-C1-6 alkyl, cyano, C1-6 alkyl, polyhalo-C1-6 alkoxy, -OR9, -C (= O) OH, C1-6 alkylcarbonyl, C1-6 alkylthio C1-6 alkylsulfonyl, -S (= O) 2NH2, and pyrrolyl, where the phenyl may be optionally substituted with halo; or two substituents on aryl ring can form -O-CH2-O- or a -O-C (CH3) 2-CH2-; Het as a group or part of a group is a mono- or bicyclic, saturated, partially unsaturated or completely unsaturated ring of 5 to 12 members containing 1 to 4 heteroatoms each independently selected from nitrogen, oxygen and sulfur, being optionally condensed with a benzene ring, and where the entire Het group may be optionally substituted with one or two substituents each independently selected from the group consisting of halo; polyhalo-C 1-6 alkyl C 1-6 alkylthio, oxo; -OR9; -NR10aR10b; -CN; C1-6 alkyl optionally substituted with -OR9, -CN, -NR10aR10b, or phenyl; -C (= O) -NH2; -C (= O) -phenyl; C3-7cycloalkyl; phenyl optionally substituted with C1-6 alkoxy; morpholinyl; pyrrolidinyl; pyrrolyl; furanoyl; tetrazolyl; and thiophenyl; and each R10a and R10b is, independently, hydrogen, C1-6 alkyl, C1-6 arylalkyl, or R10a and R10b, together with the nitrogen to which they are attached, can form a 5 to 8-membered saturated, partially unsaturated, or completely monocycle unsaturated, wherein said monocycle optionally contains an additional heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, and where the remaining monocycle members are carbon atoms; wherein said monocycle may be optionally substituted on any carbon atom with one or two substituents each independently selected from halo, C1-6alkyl, hydroxy, or oxo. Claim 22: A process for the preparation of a compound according to any of claims 1-12 having the formula (I-8), comprising the steps of reacting a deformula compound (I-2) with a compound of formula (I-4) thereby obtaining a compound of formula (I-5), and reacting a compound of formula (I-5) with an aldehyde of formula (I-7); optionally in the presence of an acid, thereby obtaining a compound of formula (I-8), wherein R1a, R1b, R4a, R4b, and R3 have the same meaning as in any of claims 1-12. Claim 23: A process for the preparation of a compound according to any of claims 1-12 having formula (I-9), comprising the step of acylating a compound of formula (I-8) with an acid or a activated acid thereby obtaining a compound of formula (1) having the formula (I-9) wherein R1a, R1b, R4a R4b, R3 and R5 have the same meaning as in any of claims 1-12. Claim 24: A process for the preparation of a compound according to any of claims 1-12 having formula (I-10), comprising the steps of reacting a compound of formula (I-8) with an isocyanate of formula (l-8a) thereby obtaining a compound of formula (I-10) being R7b hydrogen, or reacting a compound of formula (I-8) with phosgene or a phosgene equivalent of formula (I-8b), where LG represents a leaving group, followed by treatment with an amine of formula (1-8c) thereby obtaining a compound of formula (I-10), where R1a, R1b, R4a, R4b, R3, R7a and R7b have the same meaning than in any of claims 1-12. Claim 25: A process for the preparation of a compound according to claims 1-12 having the formula (I-11), comprising the step of reacting an compound of formula (I-8) with a chloroformate of formula ( l-8d) in the presence of a base, in an inert solvent obtaining from this

ARP080100660A 2007-02-16 2008-02-15 1, 1-DIOXO-1-TIA-5, 10-DIAZADIBENZOCICLOHEPTENOS USEFUL AS INHIBITORS OF THE VIRUSES OF HEPATITIS C, METHODS FOR THEIR PREPARATION, A PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND ITS USE IN THE MANUFACTURE OF AN INHIBITION REPLACEMENT MEDICATION HCV AR065374A1 (en)

Applications Claiming Priority (1)

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EP07102520 2007-02-16

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AR065374A1 true AR065374A1 (en) 2009-06-03

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ARP080100660A AR065374A1 (en) 2007-02-16 2008-02-15 1, 1-DIOXO-1-TIA-5, 10-DIAZADIBENZOCICLOHEPTENOS USEFUL AS INHIBITORS OF THE VIRUSES OF HEPATITIS C, METHODS FOR THEIR PREPARATION, A PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND ITS USE IN THE MANUFACTURE OF AN INHIBITION REPLACEMENT MEDICATION HCV

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AR (1) AR065374A1 (en)
CL (1) CL2008000491A1 (en)
PE (1) PE20081786A1 (en)
TW (1) TW200848057A (en)
UY (1) UY30922A1 (en)
WO (1) WO2008099020A1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8198305B2 (en) 2007-04-13 2012-06-12 Concert Pharmaceuticals Inc. 1,2-benzisoxazol-3-yl compounds
WO2021030278A1 (en) * 2019-08-12 2021-02-18 Aligos Therapeutics, Inc. Bicyclic compounds

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1143946B1 (en) * 1999-04-30 2004-01-28 The Regents Of The University Of Michigan Use of benzodiazepines for treating autoimmune diseases induced by apoptosis
CA2585084A1 (en) * 2004-10-26 2006-05-04 Immacolata Conte Tetracyclic indole derivatives as antiviral agents

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WO2008099020A1 (en) 2008-08-21
TW200848057A (en) 2008-12-16
CL2008000491A1 (en) 2008-08-22
UY30922A1 (en) 2008-09-02
PE20081786A1 (en) 2008-12-18

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