AR068109A1 - TETRACICLIC DERIVATIVES OF INDOL AND A PHARMACEUTICAL COMPOSITION - Google Patents

TETRACICLIC DERIVATIVES OF INDOL AND A PHARMACEUTICAL COMPOSITION

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Publication number
AR068109A1
AR068109A1 ARP080103718A ARP080103718A AR068109A1 AR 068109 A1 AR068109 A1 AR 068109A1 AR P080103718 A ARP080103718 A AR P080103718A AR P080103718 A ARP080103718 A AR P080103718A AR 068109 A1 AR068109 A1 AR 068109A1
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Argentina
Prior art keywords
alkyl
heterocycloalkyl
cycloalkyl
heteroaryl
aryl
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ARP080103718A
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Spanish (es)
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Schering Corp
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Publication of AR068109A1 publication Critical patent/AR068109A1/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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered

Abstract

La presente se refiere a derivados tetracíclicos de indol y a composiciones que comprenden por lo menos un derivado tetracíclico de indol. Estos compuestos son utiles en el tratamiento o en la prevencion de una infeccion viral o un trastorno relacionado con virus en un paciente. Reivindicacion 1: Un compuesto que tiene la formula (1) o una de sus sales, solvatos, ésteres o prodrogas aceptable para uso farmacéutico en donde X es -O-, -S-, -NH-, -N(R9)-, -OC(R8)2O- o -OC(R8)2N(R9)-; Y es =O, =NH, =NR9, =NSOR11, =NSO2R11 o =NSO2N(R11)2; Z es -N- o -C(R31)-; R1 es un enlace, -[C(R12)2]r-, -[C(R12)2]r-O-[C(R12)2]q-, -[C(R12)2]r-N(R9)-[C(R12)2]q-, -[C(R12)2]q-CH=CH-[C(R12)2]q-, -[C(R12)2]q-C:::C-[C(R12)2]q- o -[C(R12)2]q-SO2-[C(R12)2]q-; R4, R5, R6 y R7 son cada uno, de manera independiente, H, alquilo, alqueniIo, alquinilo, arilo, -[C(R12)2]q-cicloalquilo, -[C(R12)2]q-cicloalquenilo, -[C(R12)2]q-heterocicloalquilo, -[C(R12)2]q-heterocicloalquenilo, -[C(R12)2]q-heteroarilo, -[C(R12)2]q-haloalquilo, -[C(R12)2]q-hidroxialquilo, halo, hidroxi, -OR9, -CN, -[C(R12)2]q-C(O)R8, -[C(R12)2]q-C(O)OR9, -[C(R12)2]q-C(O)N(R9)2, -[C(R12)2]q-OR9, -[C(R12)2]q-N(R9)2, -[C(R12)2]q-NHC(O)R8, -[C(R12)2]q-NR8C(O)N(R9)2, -[C(R12)2]q-NHSO2R11, -[C(R12)2]q-S(O)pR11, -[C(R12)2]q-SO2N(R9)2 y -SO2N(R9)C(O)N(R9)2; o R4 y R5, junto con los átomos de carbono a los cuales están ligados, se unen para formar un grupo cíclico de 3 a 7 miembros, seleccionado entre cicloalquilo, heterocicloalquilo, arilo o heteroarilo, o R5 y R6, junto con los átomos de carbono a los cuales están ligados, se unen para formar un grupo cíclico de 3 a 7 miembros, seleccionado entre cicloalquilo, heterocicloalquilo, arilo o heteroarilo, o R6 y R7, junto con los átomos de carbono a los cuales están ligados, se unen para formar un grupo cíclico de 3 a 7 miembros, seleccionado entre cicloalquilo, heterocicloalquilo, arilo o heteroarilo, cada aparicion de R8 es de manera independiente H, alquilo, alquenilo, alquinilo, -[C(R12)2]q-arilo, -[C(R12)2]q-cicloalquilo, -[C(R12)2]q-cicloalquenilo, -[C(R12)2]q-heterocicloalquilo, -[C(R12)2]q-heterocicloalquenilo, -[C(R12)2]q-heteroarilo, haloalquilo, o hidroxialquilo, cada aparicion de R9 es de manera independiente H, alquilo, alquenilo, alquinilo, -[C(R12)2]q-arilo, -[C(R12)2]q-cicloalquilo, -[C(R12)2]q-cicloalquenilo, -[C(R12)2]q-heterocicloalquilo, -[C(R12)2]q-heterocicloalquenilo, -[C(R12)2]q-heteroarilo, haloalquilo o hidroxialquilo; R10 es H, cicloalquilo, cicloalquenilo, heterocicloalquilo, heterocicloalquenilo, arilo, heteroarilo, en donde un grupo cicloalquilo, cicloalquenilo, heterocicloalquilo, heterocicloalquenilo, arilo o heteroarilo puede estar sustituido de manera opcional e independiente con hasta 4 sustituyentes, que están seleccionados cada uno de manera independiente de H, alquilo, alquenilo, alquinilo, arilo, -[C(R12)2]q-cicloalquilo, -[C(R12)2]q-cicloalquenilo, -[C(R12)2]q-heterocicloalquilo, -[C(R12)2]q-heterocicloalquenilo, -[C(R12)2]q-heteroarilo,-[C(R12)2]q-haloalquiIo, -[C(R12)2]q-hidroxialquilo, halo, hidroxi, -OR9, -CN, -[C(R12)2]q-C(O)R8, -[C(R12)2]q-C(O)OR9, -[C(R12)2]q-C(O)N(R9)2, -[C(R12)2]q-OR9, -[C(R12)2]q-N(R9)2, -[C(R12)2]q-NHC(O)R8, -[C(R12)2]q-NR8C(O)N(R9)2, -[C(R12)2]q-NHSO2R11, -[C(R12)2]q-S(O)pR11, -[C(R12)2]q-SO2N(R9)2 y -SO2N(R9)C(O)N(R9)2; de modo tal que cuando R1 es un enlace, R10 es distinto de H; cada aparicion de R11 es en manera independiente alquilo, arilo, cicloalquilo, cicloalquenilo, heterocicloalquilo, heterocicloalquenilo, heteroarilo, haloalquilo, hidroxi, o hidroxialquilo, en donde un grupo cicloalquilo, cicloalquenilo, heterocicloalquilo, heterocicloalquenilo, arilo o heteroarilo puede estar sustituido de manera opcional e independiente con hasta 4 sustituyentes, que están seleccionados cada uno de manera independiente entre -H, alquilo, alqueniIo, alquinilo, arilo, -[C(R12)2]q-cicloalquilo, -[C(R12)2]q-cicloalquenilo, -[C(R12)2]q-heterocicloalquilo, -[C(R12)2]q-heterocicloalquenilo, -[C(R12)2]q-heteroarilo, -[C(R12)2]q-haloalquilo, -[C(R12)2]q-hidroxialquilo, halo, hidroxi, -OR9, -CN, -[C(R12)2]q-C(O)R8, -[C(R12)2]q-C(O)OR9, -[C(R12)2]q-C(O)N(R9)2, -[C(R12)2]q-OR9, -[C(R12)2]q-N(R9)2, -[C(R12)2]q-NHC(O)R8, -[C(R12)2]q-NR8C(O)N(R9)2, -[C(R12)2]q-NHSO2alquilo, -[C(R12)2]q-NHSO2cicloalquilo, -[C(R12)2]q-NHSO2arilo, -[C(R12)2]q-SO2N(R9)2 y -SO2N(R9)C(O)N(R9)2; cada aparicion de R12 es de manera independiente H, halo, -N(R9)2, -OR9, alquilo, cicloalquilo, cicloalquenilo, heterocicloalquilo o heterocicloalquenilo, en donde un grupo cicloalquilo, cicloalquenilo, heterocicloalquilo o heterocicloalquenilo puede estar sustituido de manera opcional e independiente con hasta 4 sustituyentes, que están seleccionados cada uno de manera independiente entre alquilo, halo, haloalquilo, hidroxialquilo, hidroxi, -CN, -C(O)alquilo, -C(O)Oalquilo, -C(O)NH-alquilo, -C(O)N(alquilo)2, -O-alquilo, -NH2, -NH(alquilo), -N(alquilo)2, -NHC(O)alquilo, -NHSO2alquilo, -SO2alquilo o -SO2NH-alquilo, o dos grupos geminales R12, junto con el átomo de carbono en comun al cual están ligados, se unen para formar un grupo cicloalquilo de 3 a 7 miembros, heterocicloalquilo de 3 a 7 miembros o C=O; cada aparicion de R30 es de manera independiente H, alquilo, alquenilo, alquinilo, arilo, -[C(R12)2]q-C(O)R8, -[C(R12)2]q-C(O)OR9, -[C(R12)2]q-C(O)N(R9)2, -[C(R12)2]q-OR9, -[C(R12)2]q-N(R9)2, -[C(R12)2]q-NHC(O)R8, -[C(R12)2]q-NR8C(O)N(R9)2, -[C(R12)2]q-NHSO2R11, -[C(R12)2]q-S(O)pR11, -[C(R12)2]q-SO2N(R9)2 y -SO2N(R9)C(O)N(R9)2, o cualquier R30 y R31, junto con los átomos de carbono a los cuales están ligados, se unen para formar un grupo cíclico de 3 a 7 miembros, seleccionado entre cicloalquilo, heterocicloalquilo, arilo y heteroarilo; R31 es H, alquilo, alquenilo, alquinilo, arilo; -[C(R12)2]q-cicloalquilo, -[C(R12)2]q-cicloalquenilo, -[C(R12)2]q-heterocicloalquilo, -[C(R12)2]q-heterocicloalquenilo, -[C(R12)2]q-heteroarilo, -[C(R12)2]q-haloalquilo, -[C(R12)2]q-hidroxialquilo, halo, hidroxi, -OR9, -CN, cada aparicion de p es de manera independiente 0, 1 o 2; cada aparicion de q es de manera independiente un numero entero que varía de 0 a 4; y cada aparicion de r es de manera independiente un numero entero que varía de 1 a 4.This refers to indole tetracyclic derivatives and compositions comprising at least one indole tetracyclic derivative. These compounds are useful in the treatment or prevention of a viral infection or a virus-related disorder in a patient. Claim 1: A compound having the formula (1) or one of its salts, solvates, esters or prodrugs acceptable for pharmaceutical use wherein X is -O-, -S-, -NH-, -N (R9) -, -OC (R8) 2O- or -OC (R8) 2N (R9) -; Y is = O, = NH, = NR9, = NSOR11, = NSO2R11 or = NSO2N (R11) 2; Z is -N- or -C (R31) -; R1 is a link, - [C (R12) 2] r-, - [C (R12) 2] rO- [C (R12) 2] q-, - [C (R12) 2] rN (R9) - [ C (R12) 2] q-, - [C (R12) 2] q-CH = CH- [C (R12) 2] q-, - [C (R12) 2] qC ::: C- [C ( R12) 2] q- or - [C (R12) 2] q-SO2- [C (R12) 2] q-; R4, R5, R6 and R7 are each, independently, H, alkyl, alkeny, alkynyl, aryl, - [C (R12) 2] q-cycloalkyl, - [C (R12) 2] q-cycloalkenyl, - [C (R12) 2] q-heterocycloalkyl, - [C (R12) 2] q-heterocycloalkenyl, - [C (R12) 2] q-heteroaryl, - [C (R12) 2] q-haloalkyl, - [C (R12) 2] q-hydroxyalkyl, halo, hydroxy, -OR9, -CN, - [C (R12) 2] qC (O) R8, - [C (R12) 2] qC (O) OR9, - [C (R12) 2] qC (O) N (R9) 2, - [C (R12) 2] q-OR9, - [C (R12) 2] qN (R9) 2, - [C (R12) 2] q -NHC (O) R8, - [C (R12) 2] q-NR8C (O) N (R9) 2, - [C (R12) 2] q-NHSO2R11, - [C (R12) 2] qS (O ) pR11, - [C (R12) 2] q-SO2N (R9) 2 and -SO2N (R9) C (O) N (R9) 2; or R4 and R5, together with the carbon atoms to which they are attached, bind to form a 3- to 7-membered cyclic group, selected from cycloalkyl, heterocycloalkyl, aryl or heteroaryl, or R5 and R6, together with the atoms of carbon to which they are attached, join to form a 3- to 7-membered cyclic group, selected from cycloalkyl, heterocycloalkyl, aryl or heteroaryl, or R6 and R7, together with the carbon atoms to which they are linked, bind to forming a 3 to 7 membered cyclic group, selected from cycloalkyl, heterocycloalkyl, aryl or heteroaryl, each occurrence of R8 is independently H, alkyl, alkenyl, alkynyl, - [C (R12) 2] q-aryl, - [ C (R12) 2] q-cycloalkyl, - [C (R12) 2] q-cycloalkenyl, - [C (R12) 2] q-heterocycloalkyl, - [C (R12) 2] q-heterocycloalkenyl, - [C ( R12) 2] q-heteroaryl, haloalkyl, or hydroxyalkyl, each occurrence of R9 is independently H, alkyl, alkenyl, alkynyl, - [C (R12) 2] q-aryl, - [C (R12) 2] q-cycloalkyl, - [C (R12) 2] q-cycloalkenyl, - [C (R12) 2] q-heterocycloalkyl, - [C (R12) 2] q-heterocycloalkenyl, - [C (R12) 2] q- heteroaryl, haloalkyl or hydroxyalkyl; R 10 is H, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl, wherein a cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl or heteroaryl group may be optionally and independently substituted with up to 4 substituents, which are each selected from independently of H, alkyl, alkenyl, alkynyl, aryl, - [C (R12) 2] q-cycloalkyl, - [C (R12) 2] q-cycloalkenyl, - [C (R12) 2] q-heterocycloalkyl, - [C (R12) 2] q-heterocycloalkenyl, - [C (R12) 2] q-heteroaryl, - [C (R12) 2] q-haloalkyl, - [C (R12) 2] q-hydroxyalkyl, halo, hydroxy , -OR9, -CN, - [C (R12) 2] qC (O) R8, - [C (R12) 2] qC (O) OR9, - [C (R12) 2] qC (O) N (R9 ) 2, - [C (R12) 2] q-OR9, - [C (R12) 2] qN (R9) 2, - [C (R12) 2] q-NHC (O) R8, - [C (R12 ) 2] q-NR8C (O) N (R9) 2, - [C (R12) 2] q-NHSO2R11, - [C (R12) 2] qS (O) pR11, - [C (R12) 2] q -SO2N (R9) 2 and -SO2N (R9) C (O) N (R9) 2; such that when R1 is a bond, R10 is different from H; Each occurrence of R 11 is independently alkyl, aryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, haloalkyl, hydroxy, or hydroxyalkyl, wherein a cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl group may be optionally substituted or heteroaryl. and independently with up to 4 substituents, which are each independently selected from -H, alkyl, alkenium, alkynyl, aryl, - [C (R12) 2] q-cycloalkyl, - [C (R12) 2] q-cycloalkenyl , - [C (R12) 2] q-heterocycloalkyl, - [C (R12) 2] q-heterocycloalkenyl, - [C (R12) 2] q-heteroaryl, - [C (R12) 2] q-haloalkyl, - [C (R12) 2] q-hydroxyalkyl, halo, hydroxy, -OR9, -CN, - [C (R12) 2] qC (O) R8, - [C (R12) 2] qC (O) OR9, - [C (R12) 2] qC (O) N (R9) 2, - [C (R12) 2] q-OR9, - [C (R12) 2] qN (R9) 2, - [C (R12) 2 ] q-NHC (O) R8, - [C (R12) 2] q-NR8C (O) N (R9) 2, - [C (R12) 2] q-NHSO2alkyl, - [C (R12) 2] q -NHSO2cycloalkyl, - [C (R12) 2] q-NHSO2aryl, - [C (R12) 2] q-SO2N (R9) 2 and -SO2N (R9) C (O) N (R9) 2; each occurrence of R12 is independently H, halo, -N (R9) 2, -OR9, alkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl or heterocycloalkenyl, wherein a cycloalkyl, cycloalkenyl, heterocycloalkyl or heterocycloalkenyl group may be optionally substituted and independently with up to 4 substituents, which are each independently selected from alkyl, halo, haloalkyl, hydroxyalkyl, hydroxy, -CN, -C (O) alkyl, -C (O) Oalkyl, -C (O) NH-alkyl , -C (O) N (alkyl) 2, -O-alkyl, -NH2, -NH (alkyl), -N (alkyl) 2, -NHC (O) alkyl, -NHSO2alkyl, -SO2alkyl or -SO2NH-alkyl , or two R12 geminal groups, together with the common carbon atom to which they are attached, join to form a 3- to 7-membered cycloalkyl group, 3 to 7-membered heterocycloalkyl or C = O; each occurrence of R30 is independently H, alkyl, alkenyl, alkynyl, aryl, - [C (R12) 2] qC (O) R8, - [C (R12) 2] qC (O) OR9, - [C ( R12) 2] qC (O) N (R9) 2, - [C (R12) 2] q-OR9, - [C (R12) 2] qN (R9) 2, - [C (R12) 2] q- NHC (O) R8, - [C (R12) 2] q-NR8C (O) N (R9) 2, - [C (R12) 2] q-NHSO2R11, - [C (R12) 2] qS (O) pR11, - [C (R12) 2] q-SO2N (R9) 2 and -SO2N (R9) C (O) N (R9) 2, or any R30 and R31, together with the carbon atoms to which they are linked , join to form a 3- to 7-membered cyclic group, selected from cycloalkyl, heterocycloalkyl, aryl and heteroaryl; R31 is H, alkyl, alkenyl, alkynyl, aryl; - [C (R12) 2] q-cycloalkyl, - [C (R12) 2] q-cycloalkenyl, - [C (R12) 2] q-heterocycloalkyl, - [C (R12) 2] q-heterocycloalkenyl, - [ C (R12) 2] q-heteroaryl, - [C (R12) 2] q-haloalkyl, - [C (R12) 2] q-hydroxyalkyl, halo, hydroxy, -OR9, -CN, each occurrence of p is of independent way 0, 1 or 2; each occurrence of q is independently an integer that varies from 0 to 4; and each occurrence of r is independently an integer that varies from 1 to 4.

ARP080103718A 2007-08-29 2008-08-27 TETRACICLIC DERIVATIVES OF INDOL AND A PHARMACEUTICAL COMPOSITION AR068109A1 (en)

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