[go: up one dir, main page]

AR079438A1 - SUGAR DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND THEIR USES - Google Patents

SUGAR DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND THEIR USES

Info

Publication number
AR079438A1
AR079438A1 ARP100104559A ARP100104559A AR079438A1 AR 079438 A1 AR079438 A1 AR 079438A1 AR P100104559 A ARP100104559 A AR P100104559A AR P100104559 A ARP100104559 A AR P100104559A AR 079438 A1 AR079438 A1 AR 079438A1
Authority
AR
Argentina
Prior art keywords
alkyl
aryl
heteroaryl
nrarb
heterocyclyl
Prior art date
Application number
ARP100104559A
Other languages
Spanish (es)
Inventor
Rajesh Jain
Sanjay Trehan
Sastry V R S Thungathurthi
Gurmeet Kaur Nanda
Jagattaran Das
Sitaram Kumar Magadi
Sudhir Kumar Sharma
Original Assignee
Panacea Biotec Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Panacea Biotec Ltd filed Critical Panacea Biotec Ltd
Publication of AR079438A1 publication Critical patent/AR079438A1/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02Acyclic radicals, not substituted by cyclic structures
    • C07H15/04Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
    • C07D309/10Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Diabetes (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Hematology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Obesity (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

Composiciones farmacéuticas que comprenden compuestos de formula (1) y métodos para tratar o prevenir una o más condiciones o enfermedades que se pueden regular o normalizar a través de la inhibicion del Cotransportador de Sodio y Glucosa -2 (SGLT-2). Uso de compuestos de formula (1), sus derivados, análogos, formas tautoméricas, isomeros, polimorfos, prodrogas, metabolitos, sales o solvatos de los mismos aceptables farmacéuticamente, para la fabricacion de un medicamento para la profilaxis, mejora y/o tratamiento de condiciones o enfermedades que se puedan regular o normalizar a través de la inhibicion del Cotransportador de Sodio y Glucosa -2 (SGLT-2) y las enfermedades, trastornos y condiciones relacionados, en un sujeto que lo necesite. Reivindicacion 1: Un compuesto caracterizado porque es de formula (1), o sus derivados, análogos, formas tautoméricas, isomeros, polimorfos, prodrogas, metabolitos, sales o solvatos del mismo farmacéuticamente aceptables, donde: el anillo A representa arilo; el anillo B representa arilo o heteroarilo; U, V y W se seleccionan en forma independiente entre -OH, hidrogeno, halogeno, alcoxi C1-12, -CN, -(CH2)nNR8R9, -OR8, -C(=Y)OR8 o -C(=Y)NR8R9; con la siguiente condicion: al menos dos grupos entre U, V y W representan -OR8; Y representa O o S; R7 se selecciona entre halogeno, alquilo C1-12, alquenilo C2-12, alquinilo C2-12, alquilcarbonilo C1-12, alcoxicarbonilo C1-12, cicloalquilo C3-20, heterociclilo, arilo, heteroarilo, (CH2)nRe, -CN, -NO2, -NR8R9, -N3, -CR8(=NOR9), -OH, -OR8, -CH2OH, -C(=Y)R8, -C(=Y)OR8, -C(=Y)SR8, -C(=Y)NR8R9, -OC(=Y)R8, OC(=Y)OR8, -OC(=Y)NR8R9, -OP(=O)R8R9, -(CH2)n-heterociclilo, -(CH2)n-NR8R9, -(CH2)n-N3, -(CH2)n-NCS, -(CH2)n-S(O)dR8, -(CH2)n-S(O)dNR8R9, -(CH2)n-P(=O)R8R9, -(CH2)n-OP(=O)R8R9, -(CH2)n-NR8C(=Y)R9, -(CH2)n-NR8C(=Y)OR9, -(CH2)n-NR10C(=Y)NR8R9, -(CH2)n-NR8S(O)dR9 o -(CH2)n-NHP(=O)R8R9, cada uno de los cuales puede estar opcionalmente sustituido en cualquier posicion disponible con uno o más sustituyentes seleccionados entre R11; R1, R2, R3 y R4 se seleccionan en forma independiente entre hidrogeno, halogeno, alquilo C1-12, alquenilo C2-12, alquinilo C2-12, haloalquilo C1-12, haloalquenilo C2-12, haloalquinilo C2-12, alcoxi C1-12, haloalcoxi C1-12, alcoxi C1-6alquilo C1-6, alcoxi C1-6aIcoxi C1-6aIquilo C1-3, alquilcarbonilo C1-12, alcoxicarbonilo C1-12, cicloalquilo C3-20, heterociclilo, arilo, heteroarilo, -(CH2)n-cicloalquilo, cicloalquenilo, cicloalquinilo, -(CH2)n-heterociclilo, -(CH2)n-arilo, -(CH2)n-heteroarilo, -CN, -NO2, -NR12R13, -(CH2)nNR12R13, -N3, -NCO, -(CH2)nN3, -(CH2)nNCS, -CR12(=NOR13), -NR14NR12R13, oxo, -OR12, -SR12, -(CH2)nYR12, -S(O)dR12, -S(O)dNR12R13, -(CH2)nS(O)dR12, -(CH2)nS(O)dNR12R13, -P(=O)R12R13, -(CH2)nP(=O)R12R13, -C(=Y)R12, -C(=Y)OR12, -C(=Y)SR12, -C(=Y)NR12R13, -(CH2)nC(=Y)R12, -(CH2)nC(=Y)OR12, -(CH2)nC(=Y)NR12R13, -(CH2)n-C(=Y)SR12, -OC(=Y)R12, -OC(=Y)OR12, -OC(=Y)NR12R13, -OP(=O)R12R13, -(CH2)nOC(=Y)R12, -(CH2)nOC(=Y)OR12, -(CH2)nOC(=Y)NR12R13, -(CH2)nOP(=O)R12R13, -N(R12)C(=Y)R13, -N(R12)C(=Y)OR13, -N(R14)C(=Y)NR12R13, -NR12S(O)dR13, -NHP(=O)R12R13, -(CH2)nNR12C(=Y)R13, -(CH2)nNR12C(=Y)OR13, -(CH2)nNR14C(=Y)NR12R13, -(CH2)nNR12S(O)dR13 o -(CH2)nNHP(=O)R12R13, cada uno de los cuales puede estar opcionalmente sustituido en cualquier posicion disponible con uno o más sustituyentes seleccionados entre R11; L se selecciona entre O, S, SO, SO2, -C(=O)-, -(CH2)n-, -C(=CH2)-, 1,1-ciclopropiLeno, -NR16- o -(C(R8)2)m; donde cada grupo metileno puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados en forma independiente entre halogeno, hidroxi, oxo, -C(=O)O-, -C(=O)NR16-, alquilo C1-12, alcoxi C1-12, cicloalquilo C3-20 o cicloalcoxi C3-20; E puede estar ausente o se selecciona entre CH2, O, S o NR16; G puede estar ausente o se selecciona entre alquileno C1-12, alquenileno C2-12, alquinileno C2-12, alquilencarbonilo C1-12, cicloalquileno C3-20, heterociclilo, arilo, heteroarilo, -NR15-, -(CH2)nNR15-, -(CH2)nS(O)d-, -(CH2)nS(O)dNR15-, -(CH2)nP(=O)R15-, -C(=Y)-, C(=Y)NR15-, -(CH2)nC(=Y)-, -(CH2)nC(=Y)NR15-, -(CH2)nOC(=Y)-, -(CH2)nOP(=O)R15- o -(CH2)nNR15S(O)d-, cada uno de los cuales puede estar opcionalmente sustituido en cualquier posicion disponible con uno o más sustituyentes seleccionados entre R11; R5 y R6 se seleccionan en forma independiente entre hidrogeno, alquilo C1-12, -S(O)dRa, -S(O)dNRaRb o -P(=O)RaRb, cada uno de los cuales puede estar opcionalmente sustituido en cualquier posicion disponible con R11; donde Ra y Rb pueden estar unidos para formar un anillo monocíclico o policíclico, que puede contener además uno o más heteroátomos seleccionados en forma no limitante entre O, S, SO, SO2, NR16, PR15, oxo o P(=O)R15; donde el anillo así formado puede estar sustituido adicionalmente en cualquier posicion disponible con R11; o R5 y R6 se unen junto con el átomo de nitrogeno al cual están unidos para formar un anillo monocíclico o policíclico, que contiene al menos un átomo de fosforo y puede contener además uno o más heteroátomos seleccionados en forma no limitante entre O, S, SO, SO2, NR16, PR15, oxo o P(=O)R15; donde el anillo así formado puede estar sustituido adicionalmente en cualquier posicion disponible con R11; con las siguientes condiciones: (a) R5 y R6 no pueden ser ambos hidrogeno al mismo tiempo; (b) R5 y R6 no pueden ser ambos alquilo al mismo tiempo; (c) R5 y R6 no pueden ser una combinacion de hidrogeno y alquilo al mismo tiempo; (d) cuando E y G están ausentes y R5 es hidrogeno luego R6 no puede representar -S(O)dRa; (e) cuando R7 representa alquilo C1-12, alquenilo C2-12, alquinilo C2-12, -CH2OH o -(CH2)nRe, donde n no es igual a cero; uno de R5 y R6 representa -H o alquilo C1-6 y el otro representa -S(O)dRa, donde d representa 1 o 2; luego Ra no pueden ser alquilo C1-6, alquenilo C2-6, alquinilo C2-6, arilo o heteroarilo; R8, R9, R10, R12, R13, R14 y R15 se seleccionan en forma independiente entre hidrogeno, halogeno, alquilo C1-12, alquenilo C2-12, alquinilo C2-12, alquilcarbonilo C1-12, alcoxicarbonilo C1-12, cicloalquilo C3-20, heterociclilo, arilo, heteroarilo, -(CH2)n-cicloalquilo, -(CH2)n-heterociclilo, -(CH2)n-arilo, -(CH2)n-heteroarilo, -CN, -NO2, -NRaRb, -(CH2)nNRaRb, -N3, -NCS, -(CH2)nN3, -(CH2)nNCS, -CRa(=NORb), -NRcNRaRb, -ORa, -SRa, -(CH2)nYRa, -S(O)dRa, -S(O)dNRaRb, -(CH2)nS(O)dRa, -(CH2)nS(O)dNRaRb, -P(=O)RaRb, -(CH2)nP(=O)RaRb, -C(=Y)Ra, -C(=Y)ORa, -C(=Y)SRa, -C(=Y)NRaRb, -(CH2)nC(=Y)Ra, -(CH2)nC(=Y)ORa, -(CH2)nC(=Y)NRaRb, -(CH2)n-C(=Y)SRa, -OC(=Y)Ra, -OC(=Y)ORa, -OC(=Y)NRaRb, -OP(=O)RaRb, -(CH2)nOC(=Y)Ra, -(CH2)nOC(=Y)ORa, -(CH2)nOC(=Y)NRaRb, -(CH2)nOP(=O)RaRb, -N(Ra)C(=Y)Rb, -N(Ra)C(=Y)ORb, -N(Rc)C(=Y)NRaRb, -NRaS(O)dRb, -NHP(=O)RaRb, -(CH2)nNRaC(=Y)Rb, -(CH2)nNRaC(=Y)ORb, -(CH2)nNRcC(=Y)NRaRb, -(CH2)nNRaS(O)dRb o -(CH2)nNHP(=O)RaRb, cada uno de los cuales puede estar opcionalmente sustituido en cualquier posicion disponible con uno o más sustituyentes seleccionados entre alquilo C1-12, alquenilo C2-12, alquinilo C2-12, cicloalquilo C3-20, heterociclilo, arilo, heteroarilo, halogeno, -CN, -NO2 o NH2; o R8 y R9 se unen para formar un anillo monocíclico o policíclico, que puede contener además uno o más heteroátomos seleccionados en forma no limitante entre O, S, SO, SO2, NR16, PR15, oxo o P(=O)R15; donde el anillo así, formado puede estar sustituido adicionalmente. en cualquier posicion disponible con R11; R12 y R13 se unen para formar un anillo monocíclico o policíclico, que puede contener además uno o más heteroátomos seleccionados en forma no limitante entre O, S, SO, SO2, NR16, PR15, oxo o P(=O)R15; donde el anillo así formado puede estar sustituido adicionalmente en cualquier posicion disponible con R11; R11 se selecciona entre hidrogeno, halogeno, alquilo C1-12, alquenilo C2-12, alquinilo C2-12, haloalquilo C1-12, haloalquenilo C2-12, haloalquinilo C2-12, alcoxi C1-12, haloalcoxi C1-12, alcoxi C1-6alquilo C1-6, alcoxi C1-6alcoxi C1-6alquilo C1-3, alquilcarbonilo C1-12, alcoxicarbonilo C1-12, cicloalquilo C3-20, heterociclilo, arilo, heteroarilo, -(CH2)n-cicloalquilo, -(CH2)n-heterociclilo, -(CH2)n-arilo, -(CH2)n-heteroarilo, -CN, -NO2, -NRaRb, -(CH2)nNRaRb, -N3, -NCS, -(CH2)nN3, -(CH2)nNCS, -CRa(=NORb), -NRcNRaRb, -ORa, -SRa, -(CH2)nYRa, -S(O)dRa, -S(O)dNRaRb, -(CH2)nS(O)dRa, -(CH2)nS(O)dNRaRb, -P(=O)RaRb, -(CH2)nP(=O)RaRb, -C(=Y)Ra, -C(=Y)ORa, -C(=Y)SRa, -C(=Y)NRaRb, -(CH2)nC(=Y)Ra, -(CH2)nC(=Y)ORa, -(CH2)nC(=Y)NRaRb, -(CH2)n-C(=Y)SRa, -OC(=Y)Ra, -OC(=Y)ORa, -OC(=Y)NRaRb, -OP(=O)RaRb, -(CH2)nOC(=Y)Ra, -(CH2)nOC(=Y)ORa, -(CH2)nOC(=Y)NRaRb, -(CH2)nOP(=O)RaRb, -N(Ra)C(=Y)Rb, -N(Ra)C(=Y)ORb, -N(Rc)C(=Y)NRaRb, -NRaS(O)dRb, -NHP(=O)RaRb, -(CH2)nNRaC(=Y)Rb, -(CH2)nNRaC(=Y)ORb, -(CH2)nNRcC(=Y)NRaRb, -(CH2)nNRaS(O)dRb o -(CH2)nNHP(=O)RaRb, cada uno de los cuales puede estar opcionalmente sustituido en cualquier posicion disponible con uno o más sustituyentes seleccionados entre alquilo C1-12, alquenilo C2-12, alquinilo C1-12, cicloalquilo C3-20, heterociclilo, arilo, heteroarilo, -CN, -NO2 o NH2; R16 se selecciona entre hidrogeno, alquilo C1-12, alquenilo C2-12, alquinilo C2-12, cicloalquilo C3-20, heterociclilo, arilo, heteroarilo, -CRa(=NORb), -S(O)dRa, -S(O)dNRaRb, -(CH2)nS(O)dRa, -P(=O)RaRb, -C(=Y)Ra, -C(=Y)ORa, -C(=Y)SRa o -C(=Y)NRaRb, cada uno de los cuales puede estar opcionalmente sustituido en cualquier posicion disponible con uno o mas sustituyentes seleccionados entre alquilo C1-12, alquenilo C2-12, alquinilo C2-12, cicloalquilo C3-20, heterociclilo, arilo, heteroarilo, -CN, -NO2 o NH2; Ra, Rb y Rc se seleccionan en forma independiente entre hidrogeno, halogeno, alquilo C1-12, alquenilo C2-12, alquinilo C2-12, alcoxi C1-12, alcoxi C1-6alquilo C1-6, alquilcarbonilo C1-12, alcoxicarbonilo C1-12, cicloalquilo C3-20, heterociclilo, arilo, heteroarilo, -(CH2)n-cicloalquilo, -(CH2)n-heterociclilo, -(CH2)n-arilo, -(CH2)n-heteroarilo, -CN, -NO2, -N3, -NCS, -NR8R9, -(CH2)nNR8R9, -(CH2)nN3, -(CH2)nNCS, -CR8(=NOR9), -OH, -OR8, -CH2OH, -(CH2)nYR8, -(CH2)Pharmaceutical compositions comprising compounds of formula (1) and methods for treating or preventing one or more conditions or diseases that can be regulated or normalized through the inhibition of the Sodium and Glucose Cotransporter -2 (SGLT-2). Use of compounds of formula (1), their derivatives, analogs, tautomeric forms, isomers, polymorphs, prodrugs, metabolites, salts or solvates thereof pharmaceutically acceptable, for the manufacture of a medicament for the prophylaxis, improvement and / or treatment of conditions or diseases that can be regulated or normalized through the inhibition of the Sodium and Glucose Cotransporter -2 (SGLT-2) and related diseases, disorders and conditions, in a subject in need. Claim 1: A compound characterized in that it is of formula (1), or its derivatives, analogs, tautomeric forms, isomers, polymorphs, prodrugs, metabolites, pharmaceutically acceptable salts or solvates thereof, wherein: ring A represents aryl; ring B represents aryl or heteroaryl; U, V and W are independently selected from -OH, hydrogen, halogen, C1-12 alkoxy, -CN, - (CH2) nNR8R9, -OR8, -C (= Y) OR8 or -C (= Y) NR8R9 ; with the following condition: at least two groups between U, V and W represent -OR8; Y represents O or S; R7 is selected from halogen, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 alkylcarbonyl, C1-12 alkoxycarbonyl, C3-20 cycloalkyl, heterocyclyl, aryl, heteroaryl, (CH2) nRe, -CN, -NO2, -NR8R9, -N3, -CR8 (= NOR9), -OH, -OR8, -CH2OH, -C (= Y) R8, -C (= Y) OR8, -C (= Y) SR8, - C (= Y) NR8R9, -OC (= Y) R8, OC (= Y) OR8, -OC (= Y) NR8R9, -OP (= O) R8R9, - (CH2) n-heterocyclyl, - (CH2) n-NR8R9, - (CH2) n-N3, - (CH2) n-NCS, - (CH2) nS (O) dR8, - (CH2) nS (O) dNR8R9, - (CH2) nP (= O) R8R9 , - (CH2) n-OP (= O) R8R9, - (CH2) n-NR8C (= Y) R9, - (CH2) n-NR8C (= Y) OR9, - (CH2) n-NR10C (= Y ) NR8R9, - (CH2) n-NR8S (O) dR9 or - (CH2) n-NHP (= O) R8R9, each of which may be optionally substituted at any available position with one or more substituents selected from R11; R1, R2, R3 and R4 are independently selected from hydrogen, halogen, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl, C1- alkoxy 12, C1-12 haloalkoxy, C1-6 alkoxy C1-6 alkyl, C1-6 alkoxy C1-6 alkoxy C1-3 alkyl, C1-12 alkylcarbonyl, C1-12 alkoxycarbonyl, C3-20 cycloalkyl, heterocyclyl, aryl, heteroaryl, - (CH2 ) n-cycloalkyl, cycloalkenyl, cycloalkynyl, - (CH2) n-heterocyclyl, - (CH2) n-aryl, - (CH2) n-heteroaryl, -CN, -NO2, -NR12R13, - (CH2) nNR12R13, -N3 , -NCO, - (CH2) nN3, - (CH2) nNCS, -CR12 (= NOR13), -NR14NR12R13, oxo, -OR12, -SR12, - (CH2) nYR12, -S (O) dR12, -S ( O) dNR12R13, - (CH2) nS (O) dR12, - (CH2) nS (O) dNR12R13, -P (= O) R12R13, - (CH2) nP (= O) R12R13, -C (= Y) R12 , -C (= Y) OR12, -C (= Y) SR12, -C (= Y) NR12R13, - (CH2) nC (= Y) R12, - (CH2) nC (= Y) OR12, - (CH2 ) nC (= Y) NR12R13, - (CH2) nC (= Y) SR12, -OC (= Y) R12, -OC (= Y) OR12, -OC (= Y) NR12R13, -OP (= O) R12R13 , - (CH2) nOC (= Y) R12, - (CH2) nOC (= Y) OR12, - (CH2) nOC (= Y) NR12R13, - (CH2) nOP (= O) R12R13, -N (R12) C (= Y ) R13, -N (R12) C (= Y) OR13, -N (R14) C (= Y) NR12R13, -NR12S (O) dR13, -NHP (= O) R12R13, - (CH2) nNR12C (= Y ) R13, - (CH2) nNR12C (= Y) OR13, - (CH2) nNR14C (= Y) NR12R13, - (CH2) nNR12S (O) dR13 or - (CH2) nNHP (= O) R12R13, each of the which may be optionally substituted in any available position with one or more substituents selected from R11; L is selected from O, S, SO, SO2, -C (= O) -, - (CH2) n-, -C (= CH2) -, 1,1-cyclopropylene, -NR16- or - (C (R8 ) 2) m; where each methylene group may be optionally substituted with one or more substituents independently selected from halogen, hydroxy, oxo, -C (= O) O-, -C (= O) NR16-, C1-12 alkyl, C1-alkoxy 12, C3-20 cycloalkyl or C3-20 cycloalkoxy; E may be absent or is selected from CH2, O, S or NR16; G may be absent or is selected from C1-12 alkylene, C2-12 alkenylene, C2-12 alkynylene, C1-12 alkylenecarbonyl, C3-20 cycloalkylene, heterocyclyl, aryl, heteroaryl, -NR15-, - (CH2) nNR15-, - (CH2) nS (O) d-, - (CH2) nS (O) dNR15-, - (CH2) nP (= O) R15-, -C (= Y) -, C (= Y) NR15-, - (CH2) nC (= Y) -, - (CH2) nC (= Y) NR15-, - (CH2) nOC (= Y) -, - (CH2) nOP (= O) R15- or - (CH2) nNR15S (O) d-, each of which may be optionally substituted in any available position with one or more substituents selected from R11; R5 and R6 are independently selected from hydrogen, C1-12 alkyl, -S (O) dRa, -S (O) dNRaRb or -P (= O) RaRb, each of which may be optionally substituted in any position available with R11; where Ra and Rb may be joined to form a monocyclic or polycyclic ring, which may also contain one or more heteroatoms selected in a non-limiting manner from O, S, SO, SO2, NR16, PR15, oxo or P (= O) R15; where the ring thus formed may be additionally substituted in any position available with R11; or R5 and R6 join together with the nitrogen atom to which they are attached to form a monocyclic or polycyclic ring, which contains at least one phosphorus atom and can also contain one or more heteroatoms selected in a non-limiting manner between O, S, SO, SO2, NR16, PR15, oxo or P (= O) R15; where the ring thus formed may be additionally substituted in any position available with R11; with the following conditions: (a) R5 and R6 cannot both be hydrogen at the same time; (b) R5 and R6 cannot both be alkyl at the same time; (c) R5 and R6 cannot be a combination of hydrogen and alkyl at the same time; (d) when E and G are absent and R5 is hydrogen then R6 cannot represent -S (O) dRa; (e) when R7 represents C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, -CH2OH or - (CH2) nRe, where n is not equal to zero; one of R5 and R6 represents -H or C1-6 alkyl and the other represents -S (O) dRa, where d represents 1 or 2; then Ra cannot be C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, aryl or heteroaryl; R8, R9, R10, R12, R13, R14 and R15 are independently selected from hydrogen, halogen, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 alkylcarbonyl, C1-12 alkoxycarbonyl, C3 cycloalkyl -20, heterocyclyl, aryl, heteroaryl, - (CH2) n-cycloalkyl, - (CH2) n-heterocyclyl, - (CH2) n-aryl, - (CH2) n-heteroaryl, -CN, -NO2, -NRaRb, - (CH2) nNRaRb, -N3, -NCS, - (CH2) nN3, - (CH2) nNCS, -CRa (= NORb), -NRcNRaRb, -ORa, -SRa, - (CH2) nYRa, -S (O ) dRa, -S (O) dNRaRb, - (CH2) nS (O) dRa, - (CH2) nS (O) dNRaRb, -P (= O) RaRb, - (CH2) nP (= O) RaRb, - C (= Y) Ra, -C (= Y) ORa, -C (= Y) SRa, -C (= Y) NRaRb, - (CH2) nC (= Y) Ra, - (CH2) nC (= Y ) ORa, - (CH2) nC (= Y) NRaRb, - (CH2) nC (= Y) SRa, -OC (= Y) Ra, -OC (= Y) ORa, -OC (= Y) NRaRb, - OP (= O) RaRb, - (CH2) nOC (= Y) Ra, - (CH2) nOC (= Y) ORa, - (CH2) nOC (= Y) NRaRb, - (CH2) nOP (= O) RaRb , -N (Ra) C (= Y) Rb, -N (Ra) C (= Y) ORb, -N (Rc) C (= Y) NRaRb, -NRaS (O) dRb, -NHP (= O) RaRb, - (CH2) nNRaC (= Y) Rb, - (CH2) nNRaC (= Y) ORb, - (CH2) nNRcC (= Y) NRaRb, - (CH2) nNRaS (O) dRb or - (CH2) nNHP (= O) RaRb, each of which may optionally be its substituted in any available position with one or more substituents selected from C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-20 cycloalkyl, heterocyclyl, aryl, heteroaryl, halogen, -CN, -NO2 or NH2; or R8 and R9 join to form a monocyclic or polycyclic ring, which may also contain one or more heteroatoms selected in a non-limiting manner from O, S, SO, SO2, NR16, PR15, oxo or P (= O) R15; where the ring thus formed may be additionally substituted. in any position available with R11; R12 and R13 join to form a monocyclic or polycyclic ring, which may also contain one or more heteroatoms selected in a non-limiting manner from O, S, SO, SO2, NR16, PR15, oxo or P (= O) R15; where the ring thus formed may be additionally substituted in any position available with R11; R11 is selected from hydrogen, halogen, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl, C1-12 alkoxy, C1-12 haloalkoxy, C1 alkoxy -6 C1-6 alkyl, C1-6 alkoxy C1-6 alkoxy C1-3 alkyl, C1-12 alkylcarbonyl, C1-12 alkoxycarbonyl, C3-20 cycloalkyl, heterocyclyl, aryl, heteroaryl, - (CH2) n-cycloalkyl, - (CH2) n-heterocyclyl, - (CH2) n-aryl, - (CH2) n-heteroaryl, -CN, -NO2, -NRaRb, - (CH2) nNRaRb, -N3, -NCS, - (CH2) nN3, - (CH2 ) nNCS, -CRa (= NORb), -NRcNRaRb, -ORa, -SRa, - (CH2) nYRa, -S (O) dRa, -S (O) dNRaRb, - (CH2) nS (O) dRa, - (CH2) nS (O) dNRaRb, -P (= O) RaRb, - (CH2) nP (= O) RaRb, -C (= Y) Ra, -C (= Y) ORa, -C (= Y) SRa, -C (= Y) NRaRb, - (CH2) nC (= Y) Ra, - (CH2) nC (= Y) ORa, - (CH2) nC (= Y) NRaRb, - (CH2) nC (= Y) SRa, -OC (= Y) Ra, -OC (= Y) ORa, -OC (= Y) NRaRb, -OP (= O) RaRb, - (CH2) nOC (= Y) Ra, - (CH2 ) nOC (= Y) ORa, - (CH2) nOC (= Y) NRaRb, - (CH2) nOP (= O) RaRb, -N (Ra) C (= Y) Rb, -N (Ra) C (= Y) ORb, -N (Rc) C (= Y) NRaRb, -NRaS (O) dRb, -NHP (= O) RaRb, - (CH2) nNRaC (= Y) Rb, - (CH2) nNRaC (= Y ) ORb, - (CH2) nNRcC (= Y) NRaRb, - (CH2) nNRaS (O) dRb or - (CH2) nNHP (= O) RaRb, each of which may be optionally substituted at any available position with one or more substituents selected from C1-12 alkyl, C2-12 alkenyl, C1-12 alkynyl, C3-20 cycloalkyl, heterocyclyl, aryl, heteroaryl, -CN, -NO2 or NH2; R16 is selected from hydrogen, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-20 cycloalkyl, heterocyclyl, aryl, heteroaryl, -CRa (= NORb), -S (O) dRa, -S (O ) dNRaRb, - (CH2) nS (O) dRa, -P (= O) RaRb, -C (= Y) Ra, -C (= Y) ORa, -C (= Y) SRa or -C (= Y ) NRaRb, each of which may be optionally substituted in any available position with one or more substituents selected from C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-20 cycloalkyl, heterocyclyl, aryl, heteroaryl, - CN, -NO2 or NH2; Ra, Rb and Rc are independently selected from hydrogen, halogen, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 alkoxy, C1-6 alkoxy C1-6 alkyl, C1-12 alkylcarbonyl, C1 alkoxycarbonyl -12, C3-20 cycloalkyl, heterocyclyl, aryl, heteroaryl, - (CH2) n-cycloalkyl, - (CH2) n-heterocyclyl, - (CH2) n-aryl, - (CH2) n-heteroaryl, -CN, - NO2, -N3, -NCS, -NR8R9, - (CH2) nNR8R9, - (CH2) nN3, - (CH2) nNCS, -CR8 (= NOR9), -OH, -OR8, -CH2OH, - (CH2) nYR8 , - (CH2)

ARP100104559A 2009-12-09 2010-12-09 SUGAR DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND THEIR USES AR079438A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IN2553DE2009 2009-12-09

Publications (1)

Publication Number Publication Date
AR079438A1 true AR079438A1 (en) 2012-01-25

Family

ID=44145994

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP100104559A AR079438A1 (en) 2009-12-09 2010-12-09 SUGAR DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND THEIR USES

Country Status (2)

Country Link
AR (1) AR079438A1 (en)
WO (1) WO2011070592A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014530186A (en) 2011-09-13 2014-11-17 パナセア バイオテック リミテッド Novel SGLT inhibitor
TW201335176A (en) 2011-12-15 2013-09-01 Nat Health Research Institutes Novel glycoside compounds
CA2857603C (en) 2011-12-15 2016-08-02 Pfizer Limited Sulfonamide derivatives
PT3489226T (en) 2012-11-20 2021-03-02 Lexicon Pharmaceuticals Inc Inhibitors of sodium glucose cotransporter 1
US20220259247A1 (en) * 2019-07-26 2022-08-18 Dongbao Purple Star (Hangzhou) Biopharmaceutical Co., Ltd. Sglts/dpp4 inhibitor and application thereof
EP4006017B1 (en) * 2019-07-26 2024-10-23 CGenetech (Suzhou, China) Co., Ltd. Sglt2/dpp4 inhibitor and application thereof
WO2022160737A1 (en) * 2021-01-26 2022-08-04 东宝紫星(杭州)生物医药有限公司 Crystal form of tetrahydropyran ring compound and preparation method therefor

Family Cites Families (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100591585B1 (en) 1999-08-31 2006-06-20 깃세이 야쿠힌 고교 가부시키가이샤 Glucopyranosyloxypyrazole derivatives, pharmaceutical compositions containing them, and intermediates for the production thereof
US6515117B2 (en) 1999-10-12 2003-02-04 Bristol-Myers Squibb Company C-aryl glucoside SGLT2 inhibitors and method
PH12000002657B1 (en) * 1999-10-12 2006-02-21 Bristol Myers Squibb Co C-aryl glucoside SGLT2 inhibitors
US6683056B2 (en) 2000-03-30 2004-01-27 Bristol-Myers Squibb Company O-aryl glucoside SGLT2 inhibitors and method
US6555519B2 (en) 2000-03-30 2003-04-29 Bristol-Myers Squibb Company O-glucosylated benzamide SGLT2 inhibitors and method
AU9025701A (en) 2000-09-29 2002-04-15 Kissei Pharmaceutical Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containingthe same
ES2337127T3 (en) 2000-11-02 2010-04-21 Ajinomoto Co., Inc. NEW DERIVATIVES OF PIRAZOL AND REMEDIES AGAINST DIABETES CONTAINING THEM.
CA2429833A1 (en) 2000-11-30 2002-06-06 Kissei Pharmaceutical Co., Ltd. Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates in the production thereof
TWI255817B (en) 2001-02-14 2006-06-01 Kissei Pharmaceutical Glucopyranosyloxybenzylbenzene derivatives and medicinal use thereof
CA2438593C (en) 2001-02-26 2010-09-21 Kissei Pharmaceutical Co., Ltd. Glucopyranosyloxypyrazole derivatives and medicinal use thereof
ES2350084T3 (en) 2001-02-27 2011-01-18 Kissei Pharmaceutical Co., Ltd. DERIVATIVES OF GLUCOPIRANOSILOXIPIRAZOL AND MEDICAL USE OF THE SAME.
US6936590B2 (en) 2001-03-13 2005-08-30 Bristol Myers Squibb Company C-aryl glucoside SGLT2 inhibitors and method
WO2002088157A1 (en) 2001-04-27 2002-11-07 Ajinomoto Co., Inc. N-substituted pyrazolyl-o-glycoside derivatives and remedial agent for diabetes containing the same
JP4399254B2 (en) 2001-06-20 2010-01-13 キッセイ薬品工業株式会社 Nitrogen-containing heterocyclic derivative, pharmaceutical composition containing the same, pharmaceutical use thereof and production intermediate thereof
EP1432720A1 (en) 2001-09-05 2004-06-30 Bristol-Myers Squibb Company O-pyrazole glucoside sglt2 inhibitors and method of use
TWI254635B (en) 2002-08-05 2006-05-11 Yamanouchi Pharma Co Ltd Azulene derivative and salt thereof
WO2004058790A1 (en) 2002-12-25 2004-07-15 Kissei Pharmaceutical Co., Ltd. Nitrogen-containing heterocycic derivatives, medicinal compositions containing the same and medicinal use thereof
AU2004220222B2 (en) 2003-03-14 2009-10-01 Astellas Pharma Inc. C-glycoside derivatives and salts thereof
JP2004300102A (en) 2003-03-31 2004-10-28 Kissei Pharmaceut Co Ltd Condensed heterocyclic derivative, pharmaceutical composition containing the same and its pharmaceutical application
EP1609799A4 (en) 2003-04-01 2008-10-29 Taisho Pharmaceutical Co Ltd HETEROARYL 5-THIO-BETA-D-GLUCOPYRANOSIDE DERIVATIVES AND DIABETES DRUG CONTAINING THESE DERIVATIVES
AU2003902263A0 (en) 2003-05-12 2003-05-29 Fujisawa Pharmaceutical Co., Ltd. Monosaccharide compounds
JP2004359630A (en) 2003-06-06 2004-12-24 Yamanouchi Pharmaceut Co Ltd Difluorodiphenylmethane derivative and its salt
ES2322059T3 (en) 2003-08-26 2009-06-16 Boehringer Ingelheim International Gmbh GLUCOPIRANOSILOXI-PIRAZOLES, MEDICATIONS CONTAINING THESE COMPOUNDS, THEIR USE AND PROCEDURE FOR THEIR PREPARATION.
NZ549628A (en) 2004-03-04 2010-06-25 Kissei Pharmaceutical Nitrogenous fused-ring derivatives, medicinal compositions containing the derivatives, and use thereof as drugs
JP5078350B2 (en) 2004-03-04 2012-11-21 キッセイ薬品工業株式会社 Fused heterocyclic derivative, pharmaceutical composition containing the same, and pharmaceutical use thereof
US20070185197A1 (en) 2004-03-31 2007-08-09 Hideki Fujikura Phenol derivative, medicinal composition containing the same, and medicinal use thereof
US7393836B2 (en) 2004-07-06 2008-07-01 Boehringer Ingelheim International Gmbh D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture
DE102004034690A1 (en) 2004-07-17 2006-02-02 Boehringer Ingelheim Pharma Gmbh & Co. Kg Methylidene-D-xylopyranosyl and oxo-D-xylopyranosyl-substituted phenyls, medicaments containing these compounds, their use and processes for their preparation
TW200606129A (en) 2004-07-26 2006-02-16 Chugai Pharmaceutical Co Ltd Novel cyclohexane derivative, its prodrug, its salt and diabetic therapeutic agent containing the same
JP2008508213A (en) 2004-07-27 2008-03-21 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング D-glucopyranosyl-phenyl-substituted cyclics, pharmaceuticals containing such compounds, their use and methods for their production
AR051446A1 (en) 2004-09-23 2007-01-17 Bristol Myers Squibb Co C-ARYL GLUCOSIDS AS SELECTIVE INHIBITORS OF GLUCOSE CONVEYORS (SGLT2)
DE102004048388A1 (en) 2004-10-01 2006-04-06 Boehringer Ingelheim Pharma Gmbh & Co. Kg D-pyranosyl-substituted phenyls, pharmaceutical compositions containing them, their use and processes for their preparation
EP1813611B1 (en) 2004-11-18 2014-10-01 Kissei Pharmaceutical Co., Ltd. 1-substituted-3- beta-d-glycopyranosylated nitrogenous hetero- cyclic compounds and medicines containing the same
JP2008524162A (en) 2004-12-16 2008-07-10 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Glucopyranosyl-substituted benzene derivative, drug containing the compound, use thereof and production method thereof
EP1856082B1 (en) 2005-02-23 2009-10-14 Boehringer Ingelheim International GmbH Glucopyranosyl-substituted ((hetero)arylethynyl-benzyl)-benzene derivatives and use thereof as sodium-dependent glucose cotransporter 2 (sglt2) inhibitors
WO2007000445A1 (en) 2005-06-29 2007-01-04 Boehringer Ingelheim International Gmbh Glucopyranosyl-substituted benzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
CA2620566A1 (en) 2005-08-30 2007-03-08 Boehringer Ingelheim International Gmbh Glucopyranosyl-substituted benzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
EP1989191B1 (en) 2006-02-15 2011-07-20 Boehringer Ingelheim International GmbH Glucopyranosyl-substituted benzonitrile derivatives, pharmaceutical compositions containing such compounds, their use and process for their manufacture
JP2009167104A (en) 2006-05-02 2009-07-30 Taisho Pharmaceutical Co Ltd Phenyl 5-thioglycoside compound
BRPI0711949A2 (en) 2006-05-19 2012-01-17 Taisho Pharmaceutical Co., Ltd. c-phenyl glycitol compound
TWI432446B (en) 2006-07-27 2014-04-01 Chugai Pharmaceutical Co Ltd Fused ring spiroketal derivative and use thereof as anti-diabetic drug
US20080027014A1 (en) 2006-07-28 2008-01-31 Tanabe Seiyaku Co., Ltd. Novel SGLT inhibitors
JP5384343B2 (en) 2006-08-15 2014-01-08 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Glucopyranosyl-substituted cyclopropylbenzene derivatives, pharmaceutical compositions containing such compounds, their use as SGLT inhibitors and methods for their preparation
TWI499414B (en) 2006-09-29 2015-09-11 Lexicon Pharmaceuticals Inc Inhibitors of sodium glucose co-transporter 2 and methods of their use
UY30730A1 (en) 2006-12-04 2008-07-03 Mitsubishi Tanabe Pharma Corp CRYSTAL FORM OF HEMIHYDRATE 1- (B (BETA) -D-GLUCOPYRANOSIL) -4-METHYL-3- [5- (4-FLUOROPHENYL) -2-TIENYLMETHYL] BENZENE
WO2008090570A1 (en) 2007-01-25 2008-07-31 Panacea Biotec Ltd Novel antimicrobials
TW200904454A (en) 2007-03-22 2009-02-01 Bristol Myers Squibb Co Methods for treating obesity employing an SGLT2 inhibitor and compositions thereof
US7838498B2 (en) 2007-04-02 2010-11-23 Theracos, Inc. Benzylic glycoside derivatives and methods of use
WO2009026537A1 (en) * 2007-08-23 2009-02-26 Theracos, Inc. Benzylbenzene derivatives and methods of use
WO2009116090A2 (en) 2008-03-18 2009-09-24 Panacea Biotec Limited Novel antimicrobials
CN102177147A (en) 2008-08-22 2011-09-07 泰拉科斯有限公司 Processes for the preparation of SGLT2 inhibitors

Also Published As

Publication number Publication date
WO2011070592A3 (en) 2012-05-10
WO2011070592A2 (en) 2011-06-16

Similar Documents

Publication Publication Date Title
AR079438A1 (en) SUGAR DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND THEIR USES
MX2021001754A (en) NOVEL SULFONAMIDAUREA COMPOUNDS.
AR063454A1 (en) ACETAMIDE DERIVATIVES OF DIAZEPAN AS SELECTIVE INHIBITORS OF 11 BETA - HSD1. PROCESSES OF OBTAINING AND PHARMACEUTICAL COMPOSITIONS.
AR077999A1 (en) ANTIGONISTS OF PYRIMIDIN AND TRIAZIN-HEPCIDINE
AR072249A1 (en) INHIBITORS OF AMIDA HYDROLASS ACID FAT. APPLICATIONS. METHODS
AR083367A1 (en) QUINAZOLINONE TYPE COMPOUNDS AS CRTH ANTAGONISTS
AR082562A1 (en) ISOXAZOLINE DERIVATIVES AS ANTIPARASITARY AGENTS
AR063226A1 (en) BIFENILSULFONILOS Y HENEROARIL SULFONILOS PHENYL AS MODULATORS OF THE H3 HISTAMINE RECEPTOR, ITS USE IN MEDICATIONS FOR THE TREATMENT OF RELATED DISORDERS AND A PHARMACEUTICAL COMPOSITION THAT INCLUDES THEM.
PE20142294A1 (en) INDOLE AND INDAZOLE COMPOUNDS THAT ACTIVATE AMPK
AR066882A1 (en) DERIVATIVES OF OXADIAZOL, A PHARMACEUTICAL COMPOSITION THAT INCLUDES THEM AND ITS USE IN THE PREPARATION OF MEDICINES FOR THE TREATMENT OF DISORDERS ASSOCIATED WITH THE DYSFUNCTION OF GLUTAMATE.
AR065811A1 (en) DERIVATIVES OF 2-AMINO-4H-IMIDAZOL-4-ONA, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND USES FOR THE TREATMENT OF ALZHEIMER'S DISEASE AND OTHER NEURODEGENERATIVE DISORDERS.
RU2009126745A (en) SULFONILPHENYL-2H- {1,2,4} OXADADIAZOL-5-ONE DERIVATIVES, METHODS FOR THEIR PRODUCTION AND THEIR APPLICATION AS PHARMACEUTICAL PRODUCTS
AR065622A1 (en) DERIVATIVES OF 3-CIANO -4- (4-PHENYL- PIPERIDIN -1- IL) PIRIDIN -2- ONA
AR066121A1 (en) PIRIMIDINONE DERIVATIVES AND METHODS FOR USE
AR066881A1 (en) DERIVATIVES OF OXADIAZOL, A PHARMACEUTICAL COMPOSITION THAT INCLUDES THEM AND ITS USE IN THE PREPARATION OF MEDICINES FOR THE TREATMENT OF DISORDERS ASSOCIATED WITH THE DYSFUNCTION OF GLUTAMATE.
MA32175B1 (en) Oxadiazoanthracenes for the treatment of diabetes
AR039934A1 (en) INDOLES REPLACED FOR THE TREATMENT OF RESPIRATORY DISORDERS
MA29685B1 (en) SPIROHETEROCYCLIC COMPOUNDS AND THEIR USES AS THERAPEUTIC AGENTS
AR083200A1 (en) N-HETEROARILO COMPOUNDS
BRPI0907122B8 (en) substituted pyridoindoles (1-azinone) compounds, pharmaceutical composition comprising said compounds, and uses thereof
AR077892A1 (en) ANTAGONIST QUINOLINS OF HEPCIDINE
AR064318A1 (en) COMPOUND AND COMPOSITION DERIVED FROM ARIL SULFAMIDA, USE OF THE COMPOUND AND PROCESS FOR THE PREPARATION OF THE COMPOUND
AR058760A1 (en) DERIVATIVES OF ARIL -ISOXASOL -4-IL- IMIDAZOL
AR049711A1 (en) HETEROCICLIC COMPOUNDS CONDENSED AS INHIBITORS OF ALDOSTERONE SINTASA; PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND THEIR USE IN THE PREPARATION OF A MEDICINAL PRODUCT FOR THE TREATMENT OR PREVENTION OF DISEASES RELATED TO HYPERALDOSTERISM AND EXCESSIVE CORTISO RELEASE
AR082111A1 (en) FUROPIRIDINES OR CONDENSED TENOPIRIDINS, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM USEFUL TO TREAT PSYCHOTIC AND CENTRAL NERVOUS SYSTEM DISORDERS, AND THE SAME PREPARATION METHOD

Legal Events

Date Code Title Description
FB Suspension of granting procedure