AR036776A1 - CYCLIC DERIVATIVES OF INDOL AND HETEROINDOL, ITS PREPARATION AND USE AS MEDICATIONS - Google Patents

CYCLIC DERIVATIVES OF INDOL AND HETEROINDOL, ITS PREPARATION AND USE AS MEDICATIONS

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Publication number
AR036776A1
AR036776A1 ARP020103329A ARP020103329A AR036776A1 AR 036776 A1 AR036776 A1 AR 036776A1 AR P020103329 A ARP020103329 A AR P020103329A AR P020103329 A ARP020103329 A AR P020103329A AR 036776 A1 AR036776 A1 AR 036776A1
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AR
Argentina
Prior art keywords
alkyl
substituted
straight
different
alkoxy
Prior art date
Application number
ARP020103329A
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Spanish (es)
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Zentaris Gmbh
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.)
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Publication date
Priority claimed from DE10143079A external-priority patent/DE10143079A1/en
Application filed by Zentaris Gmbh filed Critical Zentaris Gmbh
Publication of AR036776A1 publication Critical patent/AR036776A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D515/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D515/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D515/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D515/14—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Derivados de indol y heteroindol, de la formula general (1), donde R1 significa hidrógeno, arilo C6-14 insustituido ó sustituido total ó parcialmente, igual o diferente, heteroarilo C1-13 insustituido ó sustituido total ó parcialmente, igual o diferente, que presenta al menos uno a cuatro N, NH, O y/o S como miembros del anillo, cicloalquilo C3-8 insustituido ó sustituido total ó parcialmente, igual o diferente, ó alquilo C1-20 insustituido ó sustituido total ó parcialmente, igual o diferente, de cadena lineal o ramificada; A, B, C, ó D son, independientemente entre sí, un átomo de carbono ó un átomo de nitrógeno, sustituido con R2-R5; R2, R3, R4 y R5 significan, independientemente entre sí, un par de electrones libres (cuando A, B, C ó D son un átomo de nitrógeno), hidrógeno, halógeno, ciano, nitro, hidroxi, alquilo C1-6 de cadena lineal o ramificada, alquilo C1-6 de cadena lineal o ramificada, sustituido con uno o varios átomos de halógeno, alcoxi C1-6 de cadena lineal o ramificada, alcoxi C1-6 de cadena lineal o ramificada, sustituido con uno o varios átomos de halógeno, alquilendioxi C1-6 de cadena lineal o ramificada, alquilcarboniloxi C1-6, alcoxicarboniloxi C1-6, alquiltio C1-6, alquilsulfinilo C1-6, alquilsulfonilo C1-6, carboxi, éster carboxi alquilo C1-6, carboxamida, N-alquil C1-6-carboxamida, N,N-di-alquil C1-6-carboxamida, alcoxi C1-6-alquilo C1-6, amino, mono-alquilamino C1-6, di-alquilamino C1-6, donde los dos radicales C1-6 pueden formar entre sí un anillo, el cual presenta opcionalmente uno o varios NH, N-alquilo C1-6, O ó S, arilo C6-14, ariloxi C6-14, aril C6-14-alquilo-C1-6, aril C6-14-alcoxi-C1-6-alquilo-C1-6, alquilcarbonilo C1-6, alcoxicarbonilo C1-6, hidroxi, donde dos radicales adyacentes pueden estar unidos entre sí; R6 significa arilo C6-14 insustituido ó sustituido total ó parcialmente, igual o diferente, heteroarilo C1-13 insustituido ó sustituido total ó parcialmente, igual o diferente, que presenta al menos uno a cuatro N, NH, O y/o S como miembros del anillo, cicloalquilo C3-8 insustituido ó sustituido total ó parcialmente, igual o diferente, alquilo C1-20 insustituido ó sustituido total ó parcialmente, igual o diferente, de cadena lineal o ramificada, donde los sustituyentes, iguales o diferentes, están seleccionados del grupo compuesto por hidrógeno, flúor, cloro, bromo, iodo, ciano, nitro, hidroxi, alquilo C1-6, alcoxi C1-6, carboxi, alquilo C1-6 sustituido igual o diferente, con uno o varios átomos de halógeno, alcoxi C1-6, sustituido igual o diferente con uno o varios átomos de halógeno, alquenilo C2-6 de cadena lineal o ramificada, alquinilo C2-6 de cadena lineal o ramificada, cicloalquilo C3-8, alcoxi C1-6 de cadena lineal o ramificada, alquilendioxi C1-6 de cadena lineal o ramificada, alcoxi C1-6-alquilo-C1-6, arilo C6-14, aril C6-14-alquilo-C1-6, aril C6-14-alcoxi-C1-4-alquilo-C1-6; X es un grupo carbonilo (C=O), sulfóxido (S=O) ó sulfonilo (SO2); Y significa un átomo de oxígeno ó un átomo de nitrógeno (NR7), sustituido con el radical R7, donde R7 significa arilo C6-14 insustituido ó sustituido total ó parcialmente, igual o diferente, heteroarilo C1-13 insustituido ó sustituido total ó parcialmente, igual o diferente, que presenta al menos uno a cuatro N, NH, O y/o S como miembros del anillo, cicloalquilo C3-8 insustituido ó sustituido total ó parcialmente, igual o diferente, alquilo C1-20, insustituido o sustituido total o parcialmente igual o diferente, de cadena lineal o ramificada, donde los sustituyentes, iguales o diferentes, están seleccionados del grupo compuesto por hidrógeno, flúor, cloro, bromo, iodo, ciano, nitro, hidroxi, alquilo C1-6, alcoxi C1-6, carboxi, alquilo C1-6 sustituido igual o diferente con uno o varios átomos de halógeno, alcoxi C1-6 sustituido igual o diferente con uno o varios átomos de halógeno, alquenilo C2-6 de cadena lineal o ramificada, alquinilo C2-6 de cadena lineal o ramificada, cicloalquilo C3-8, alcoxi C1-6 de cadena lineal o ramificada, alquilendioxi C1-6 de cadena lineal o ramificada, alcoxi C1-6-alquilo-C1-6, mono-alquilamino C1-6 de cadena lineal o ramificada, dialquilamino C1-6 de cadena lineal o ramificada, donde los dos radicales C1-4 pueden formar entre sí un anillo, el cual presenta opcionalmente uno o varios NH, N-alquilo C1-6, O ó S, arilo C6-14, aril C6-14-alquilo-C1-6-, aril C6-14-alcoxi-C1-4-alquilo-C1-6, alquilcarbonilo C1-6, alcoxicarbonilo C1-6; n es igual a 0 ó 1, con la condición de que, cuando n = 0, entonces Z sea un átomo de carbono (C-R8), sustituido con el radical R8, donde R8 significa arilo C6-14 insustituido ó sustituido total ó parcialmente, igual o diferente, heteroarilo C1-13 insustituido ó sustituido total ó parcialmente, igual o diferente, que presenta al menos uno a cuatro N, NH, O y/o S como miembros del anillo, cicloalquilo C3-8 insustituido ó sustituido total ó parcialmente, igual o diferente, alquilo C1-20 insustituido ó sustituido total ó parcialmente, igual o diferente, de cadena lineal o ramificada, donde los sustituyentes, iguales o diferentes, están seleccionados del grupo compuesto por hidrógeno, flúor, cloro, bromo, iodo, ciano, nitro, hidroxi, alquilo C1-6, alcoxi C1-6, carboxi, alquilo C1-6 sustituido igual o diferente por uno o varios átomos de halógeno, alcoxi C1-6 igual o diferente sustituido con uno o varios átomos de halógeno, alquenilo C2-6 de cadena lineal o ramificada, alquinilo C2-6 de cadena lineal o ramificada, cicloalquilo C3-8, alcoxi C1-6 de cadena lineal o ramificada, alquilendioxi C1-6 de cadena lineal o ramificada, alquiltio C1-6 de cadena lineal o ramificada, alquilsulfinilo C1-4, alquilsulfonilo C1-4, ariltio C6-14, arilsulfinilo C6-14, arilsulfonilo C6-14, alcoxi C1-6-alquilo-C1-6 ó mono-alquilamino C1-6, de cadena lineal o ramificada, dialquilamino C1-6 de cadena lineal o ramificada, donde los dos radicales C1-4 pueden formar entre sí un anillo, el cual presenta opcionalmente uno o varios NH, N-alquilo C1-6, O ó S, arilo C6-14, ariloxi C6-14, aril C6-14-alquilo-C1-6, aril C6-14-alcoxi-C1-4-alquilo-C1-6, alquilcarbonilo C1-6, alcoxicarbonilo C1-6, mono-N-alquil C1-6-carbonilamino de cadena lineal o ramificada, di-N,N-alquil C1-6-carbonilamino de cadena lineal o ramificada, mono-N-alcoxi C1-6-carbonilamino de cadena lineal o ramificada, di-N,N-alcoxi C1-6-carbonilamino de cadena lineal o ramificada, N-alquil C1-6-carbonilamino-N-alquil C1-6-amino de cadena lineal o ramificada, N-alcoxi C1-6-carbonilamino-N-alquil C1-6-amino de cadena lineal o ramificada; y que, cuando n = 1, entonces Z significa un átomo de nitrógeno; sus tautómeros, sus estereoisómeros, sus mezclas, así como sus sales de tolerancia farmacéutica. Procedimiento para preparar compuestos de acuerdo con la fórmula (1). Medicamento que contiene al menos un compuesto de fórmula (1) junto con excipientes, diluyentes y/o vehículos farmacéuticamente usuales. Los compuestos de fórmula (1) son útiles como medicamentos, sobre todo como agentes antitumorales en mamíferos, especialmente en el ser humano.Derivatives of indole and heteroindole, of the general formula (1), where R1 means hydrogen, C6-14 aryl unsubstituted or substituted totally or partially, the same or different, C1-13 heteroaryl unsubstituted or substituted totally or partially, the same or different, than it has at least one to four N, NH, O and / or S as ring members, C3-8 cycloalkyl unsubstituted or substituted totally or partially, the same or different, or C1-20 alkyl unsubstituted or substituted totally or partially, the same or different , linear or branched chain; A, B, C, or D are, independently of each other, a carbon atom or a nitrogen atom, substituted with R2-R5; R2, R3, R4 and R5 mean, independently of each other, a pair of free electrons (when A, B, C or D are a nitrogen atom), hydrogen, halogen, cyano, nitro, hydroxy, C1-6 alkyl chain linear or branched, C1-6 straight or branched chain alkyl, substituted with one or more halogen atoms, C1-6 straight or branched chain alkoxy, C1-6 straight or branched chain alkoxy, substituted with one or more atoms of halogen, C1-6 straight or branched chain alkylenedioxy, C1-6 alkylcarbonyloxy, C1-6 alkoxycarbonyloxy, C1-6 alkylthio, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, carboxy, carboxy ester C1-6 alkyl, carboxamide, N- C 1-6 alkyl-carboxamide, N, N-di-C 1-6 alkyl-carboxamide, C 1-6 alkoxy-C 1-6 alkyl, amino, mono- C 1-6 alkylamino, C 1-6 alkylamino, where the two radicals C1-6 can form a ring with each other, which optionally has one or more NH, N- C1-6 alkyl, O or S, C6-14 aryl, C6-14 aryloxy, C6-14 aryl-C1-6 alkyl , aril C6-1 4-C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkylcarbonyl, C 1-6 alkoxycarbonyl, hydroxy, where two adjacent radicals can be linked together; R6 means C6-14 aryl unsubstituted or substituted in whole or in part, same or different, C1-13 heteroaryl unsubstituted or substituted in whole or in part, same or different, having at least one to four N, NH, O and / or S as members of the ring, C3-8 cycloalkyl unsubstituted or substituted totally or partially, same or different, C1-20 alkyl unsubstituted or substituted totally or partially, same or different, straight or branched chain, where the substituents, the same or different, are selected from group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, hydroxy, C1-6 alkyl, C1-6 alkoxy, carboxy, C1-6 alkyl substituted the same or different, with one or more halogen atoms, C1 alkoxy -6, substituted the same or different with one or more halogen atoms, straight or branched C2-6 alkenyl, straight or branched C2-6 alkynyl, C3-8 cycloalkyl, straight or branched C1-6 alkoxy, C1-6 alkylenedioxy chain line 1 or branched, C 1-6 alkoxy-C 1-6 alkyl, C 6-14 aryl, C 6-14 aryl-C 1-6 alkyl, C 6-14 aryl-C 1-4 alkoxy-C 1-6 alkyl; X is a carbonyl (C = O), sulfoxide (S = O) or sulfonyl (SO2) group; Y means an oxygen atom or a nitrogen atom (NR7), substituted with the radical R7, where R7 means C6-14 aryl unsubstituted or substituted totally or partially, the same or different, C1-13 heteroaryl unsubstituted or substituted totally or partially, same or different, having at least one to four N, NH, O and / or S as ring members, C3-8 cycloalkyl unsubstituted or substituted totally or partially, same or different, C1-20 alkyl, unsubstituted or substituted totally or partially equal or different, straight or branched chain, where the substituents, the same or different, are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, hydroxy, C1-6 alkyl, C1-6 alkoxy , carboxy, C1-6 alkyl substituted the same or different with one or more halogen atoms, C1-6 alkoxy substituted the same or different with one or more halogen atoms, C2-6 straight or branched chain alkenyl, C2-6 alkynyl of linear or branched chain gives, C3-8 cycloalkyl, C1-6 straight or branched chain alkoxy, C1-6 straight or branched chain alkylenedioxy, C1-6 alkoxy-C1-6 alkoxy, C1-6 straight or branched chain alkylamino, C1-6 straight or branched chain dialkylamino, where the two C1-4 radicals can form a ring, which optionally has one or more NH, N- C1-6 alkyl, O or S, C6-14 aryl, aryl C6-14-C1-6- alkyl, C6-14 aryl-C1-4 alkoxy-C1-6 alkyl, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl; n is equal to 0 or 1, with the proviso that, when n = 0, then Z is a carbon atom (C-R8), substituted with the radical R8, where R8 means unsubstituted or substituted C6-14 aryl or partially, the same or different, unsubstituted or substituted C1-13 heteroaryl totally or partially, the same or different, presenting at least one to four N, NH, O and / or S as ring members, unsubstituted or substituted C3-8 cycloalkyl total or partially, same or different, unsubstituted or substituted C1-20 alkyl totally or partially, same or different, straight or branched chain, where the substituents, the same or different, are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, hydroxy, C1-6 alkyl, C1-6 alkoxy, carboxy, C1-6 alkyl substituted the same or different by one or more halogen atoms, C1-6 alkoxy the same or different substituted with one or more atoms of halogen, C2-6 straight or branched chain alkenyl, alq C2-6 linear or branched chain uinyl, C3-8 cycloalkyl, C1-6 straight or branched chain alkoxy, C1-6 straight or branched chain alkylenedioxy, C1-6 straight or branched chain alkylthio, C1-4 alkylsulfinyl, C1-4 alkylsulfonyl, C6-14 arylthio, C6-14 arylsulfinyl, C6-14 arylsulfonyl, C1-6 alkoxy-C1-6 alkyl or mono- C 1-6 alkylamino chain, straight or branched chain, C1-6 dialkylamino chain linear or branched, where the two C1-4 radicals can form a ring with each other, which optionally has one or more NH, N- C1-6 alkyl, O or S, C6-14 aryl, C6-14 aryloxy, C6 aryl -14-C1-6 alkyl, C6-14 aryl-C1-4 alkoxy-C1-6 alkyl, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, mono-N-C1-6 straight-chain alkylcarbonylamino or branched, di-N, N-C 1-6 alkyl-straight or branched chain carbonylamino, mono-N-C 1-6 alkoxy-straight or branched chain, di-N, N-C 1-6 alkoxy-carbonylamino chain linear or branched, N-C1-6 alkylcarbonylamino-N-C1-alkyl 6-amino straight or branched chain, N-alkoxy C1-6-carbonylamino-N-alkyl C1-6-straight or branched chain amino; and that, when n = 1, then Z means a nitrogen atom; their tautomers, their stereoisomers, their mixtures, as well as their pharmaceutical tolerance salts. Procedure for preparing compounds according to formula (1). Medication containing at least one compound of formula (1) together with pharmaceutically usual excipients, diluents and / or vehicles. The compounds of formula (1) are useful as medicaments, especially as antitumor agents in mammals, especially in humans.

ARP020103329A 2001-09-03 2002-09-03 CYCLIC DERIVATIVES OF INDOL AND HETEROINDOL, ITS PREPARATION AND USE AS MEDICATIONS AR036776A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE10143079A DE10143079A1 (en) 2001-09-03 2001-09-03 Cyclic indole and heteroindole derivatives, their production and use as medicines

Publications (1)

Publication Number Publication Date
AR036776A1 true AR036776A1 (en) 2004-10-06

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Application Number Title Priority Date Filing Date
ARP020103329A AR036776A1 (en) 2001-09-03 2002-09-03 CYCLIC DERIVATIVES OF INDOL AND HETEROINDOL, ITS PREPARATION AND USE AS MEDICATIONS

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EP (1) EP1423393A1 (en)
JP (1) JP2005508898A (en)
KR (1) KR20040029463A (en)
CN (1) CN1551885A (en)
AR (1) AR036776A1 (en)
BR (1) BR0212300A (en)
CA (1) CA2458399A1 (en)
HU (1) HUP0401446A3 (en)
IL (1) IL160441A0 (en)
MX (1) MXPA04002034A (en)
NO (1) NO20040831L (en)
NZ (1) NZ531642A (en)
PL (1) PL370210A1 (en)
RU (1) RU2004110412A (en)
ZA (1) ZA200401290B (en)

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CN111362891A (en) * 2020-04-01 2020-07-03 杭州福斯特药业有限公司 Production device and production method of acetyl tetrahydrofuran

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CN1551885A (en) 2004-12-01
NZ531642A (en) 2005-01-28
KR20040029463A (en) 2004-04-06
BR0212300A (en) 2004-10-13
RU2004110412A (en) 2005-03-20
EP1423393A1 (en) 2004-06-02
NO20040831L (en) 2004-04-13
HUP0401446A3 (en) 2006-11-28
JP2005508898A (en) 2005-04-07
IL160441A0 (en) 2004-07-25
PL370210A1 (en) 2005-05-16
HUP0401446A2 (en) 2004-11-29
MXPA04002034A (en) 2004-07-08
CA2458399A1 (en) 2003-03-13
ZA200401290B (en) 2004-03-23

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