AR063661A1 - INDOLES DERIVED FROM SOLUBLE CYCLING ADENYLATE, PROCEDURE FOR THE PREPARATION AND MEDICINES CONTAINING THEM. - Google Patents

INDOLES DERIVED FROM SOLUBLE CYCLING ADENYLATE, PROCEDURE FOR THE PREPARATION AND MEDICINES CONTAINING THEM.

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AR063661A1
AR063661A1 ARP070101194A ARP070101194A AR063661A1 AR 063661 A1 AR063661 A1 AR 063661A1 AR P070101194 A ARP070101194 A AR P070101194A AR P070101194 A ARP070101194 A AR P070101194A AR 063661 A1 AR063661 A1 AR 063661A1
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alkyl
acyl
aryl
optionally substituted
different
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Spanish (es)
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Bernd Menzenbach
Dirk Kosemund
Bernd Buchmann
Martin Fritsch
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Bayer Schering Pharma Ag
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/16—Masculine contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

Compuestos de la fórmula general (1) donde R1 representa hidrógeno, halógeno, CF3, cicloalquilo C3-6, que opcionalmente puede estar saturado varias veces, u opcionalmente puede estar sustituido varias veces, o el grupo alquilo C1-6, arilo C1-6, acilo C1-6, halo-C1-6-alquilo, alquil C1-6-alquilo C1-6, alquil C1-6-acilo C1-6, acil C1-6-acilo C1-6, alquil C1-6-arilo C1-6, aril C1-6-alquilo C1-6 o CF3, donde el grupo alquilo C1-6, arilo C1-6, acilo C1-6, halo-C1-6-alquilo, alquil C1-6-alquilo C1-6, alquil C1-6-acilo C1-6, acil C1-6-acilo C1-6, alquil C1-6-arilo C1-6 o aril C1-6-alquilo C1-6 puede estar interrumpido por uno o más átomos de oxígeno, azufre o nitrógeno, iguales o diferentes, o el grupo sulfonil C1-6-alquilo, sulfonamida, o ciano, R2 representa halógeno, CF3, cicloalquilo C3-6, que opcionalmente puede estar saturado varias veces, u opcionalmente puede estar sustituido varias veces, o el grupo alquilo C1-6, arilo C1-6, acilo C1-6, halo-C1-6-alquilo, alquil C1-6-alquilo C1-6, alquil C1-6-acilo C1-6, acil C1-6-acilo C1-6, alquil C1-6-arilo C1-6, aril C1-6-alquilo C1-6 o CF3, donde el grupo alquilo C1-6, arilo C1-6, acilo C1-6, halo-C1-6-alquilo, alquil C1-6-alquilo C1-6, alquil C1-6-acilo C1-6, acil C1-6-acilo C1-6, alquil C1-6-arilo C1-6 o aril C1-6-alquilo C1-6 puede estar interrumpido por uno o más átomos de oxígeno, azufre o nitrógeno, iguales o diferentes, o el grupo sulfonil C1-6-alquilo, sulfonamida, o ciano, R3 representa arilo C6-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6 o acilo C1-6, que pueden estar opcionalmente sustituidos en una o más posiciones, o con alcoxilo C1-6, hidroxilo, ciano, CO2-alquilo C1- 6, N-(alquilo C1-6)2, CO-NR4R5 o CF3, heteroarilo C5-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6, acilo C1-6, alcoxilo C1-6, hidroxilo, ciano, CO2-alquilo C1-6 , N-(alquilo C1-6)2, CO-NR4R5 o CF3 o cicloalquilo C3-6, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, CF3, hidroxilo, ciano, CO2-alquilo C1-6, alquilo C1-6, acilo C1-6, N-(alquilo C1-6)2, CO-NR4R5 o alcoxilo C1-6, R4 representa hidrógeno, cicloalquilo C3-6, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre alquilo C1-6, acilo C1-6, alcoxilo C1-6, o CF3, arilo C6-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6, acilo C1-6, alcoxilo C1-6, N-alquil C1-6-alquilo C1-6, CF3 o ciano, o heteroarilo C5-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6, acilo C1-6, alcoxilo C1-6, N-alquil C1-6-alquilo C1-6, CF3 o ciano, o alquilo C1-6, el cual puede estar opcionalmente sustituido, R5 representa hidrógeno, alquil C1-6-cicloalquilo C3-6, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre alquilo C1-6, acilo C1-6, alcoxilo C1-6, o CF3, cicloalquilo C3-6, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre alquilo C1-6, acilo C1-6, alcoxilo C1-6, o CF3, arilo C6-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6, acilo C1-6, alcoxilo C1-6, N-alquil C1-6-alquilo C1-6, CF3 o ciano, o heteroarilo C5-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6, acilo C1-6, alcoxilo C1-6, N-alquil C1-6-alquilo C1-6, CF3 o ciano, o alquilo C1-6, el cual puede estar opcionalmente sustituido, R4 y R5 forman juntos un anillo de 5-8 miembros, que puede contener otros heteroátomos, y R6 representa el grupo alquilo C1- 6, acilo C1-6, alquil C1-6-cicloalquilo C3-6, alquil C1-6-arilo C6-12, donde el grupo alquilo C1-6, acilo C1-6, alquil C1-6-cicloalquilo C3-6, alquil C1-6-arilo C6-12, que opcionalmente puede estar sustituido por uno o más grupos hidroxilo, metoxilo, etoxilo, iso-propoxilo, cloro, bromo, fluoro, ciano, metil-sulfonilo o amino-sulfonilo, y también sus isómeros, sus diastereómeros, sus enantiómeros y sus sales. Procedimientos para elaborarlos, medicamentos que los contienen e intermediarios de la fórmula general (2) donde R1, R2, R3 y R6 tienen los significados indicados con anterioridad, y R7 puede ser H o un radical alquilo C1-6, de la fórmula general (7) donde R1, R2 y R7 tienen los significados indicados con anterioridad, y de la fórmula general (9) donde R1, R2, R6 y R7 tienen los significados indicados con anterioridad. Reivindicación 1: Compuestos de la fórmula general (1) donde R1 representa hidrógeno, halógeno, CF3, cicloalquilo C3-6, que opcionalmente puede estar saturado varias veces, u opcionalmente puede estar sustituido varias veces, o el grupo alquilo C1-6, arilo C1-6, acilo C1-6, halo-C1-6-alquilo, alquil C1-6-alquilo C1-6, alquil C1-6-acilo C1-6, acil C1-6-acilo C1-6, alquil C1-6-arilo C1-6, aril C1-6-alquilo C1-6 o CF3, donde el grupo alquilo C1-6, arilo C1-6, acilo C1-6, halo-C1-6-alquilo, alquil C1-6-alquilo C1-6, alquil C1-6-acilo C1-6, acil C1-6-acilo C1-6, alquil C1-6-arilo C1-6 o aril C1-6-alquilo C1-6 puede estar interrumpido por uno o más átomos de oxígeno, azufre o nitrógeno, iguales o diferentes, o el grupo sulfonil C1-6-alquilo, sulfonamida, o ciano, R2 representa halógeno, CF3, cicloalquilo C3-6, que opcionalmente puede estar saturado varias veces, u opcionalmente puede estar sustituido varias veces, o el grupo alquilo C1-6, arilo C1-6, acilo C1-6, halo-C1-6-alquilo, alquil C1-6-alquilo C1-6, alquil C1-6-acilo C1-6, acil C1-6-acilo C1-6, alquil C1-6-arilo C1-6, aril C1-6-alquilo C1-6 o CF3, donde el grupo alquilo C1-6, arilo C1-6, acilo C1-6, halo-C1-6-alquilo, alquil C1-6-alquilo C1-6, alquil C1-6-acilo C1-6, acil C1-6-acilo C1-6, alquil C1-6-arilo C1-6 o aril C1-6-alquilo C1-6 puede estar interrumpido por uno o más átomos de oxígeno, azufre o nitrógeno, iguales o diferentes, o el grupo sulfonil C1-6-alquilo, sulfonamida, o ciano, R3 representa arilo C6-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6 o acilo C1-6, que pueden estar opcionalmente sustituidos en una o más posiciones, o con alcoxilo C1-6, hidroxilo, ciano, CO2-alquilo C1-6, N-(alquilo C1-6)2, CO-NR4R5 o CF3, heteroarilo C5-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6, acilo C1-6, alcoxilo C1-6, hidroxilo, ciano, CO2-alquilo C1-6 , N-(alquilo C1-6)2, CO-NR4R5 o CF3 o cicloalquilo C3-6, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, CF3, hidroxilo, ciano, CO2-alquilo C1-6, alquilo C1-6, acilo C1-6, N-(alquilo C1-6)2, CO-NR4R5 o alcoxilo C1-6, R4 representa hidrógeno, cicloalquilo C3-6, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre alquilo C1-6, acilo C1-6, alcoxilo C1-6, o CF3, arilo C6-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6, acilo C1-6, alcoxilo C1-6, N-alquil C1-6-alquilo C1-6, CF3 o ciano, o heteroarilo C5-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6, acilo C1-6, alcoxilo C1-6, N-alquil C1-6-alquilo C1-6, CF3 o ciano, o alquilo C1-6, el cual puede estar opcionalmente sustituido, R5 representa hidrógeno, alquil C1-6-cicloalquilo C3-6, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre alquilo C1-6, acilo C1-6, alcoxilo C1-6, o CF3, cicloalquilo C3-6, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre alquilo C1-6, acilo C1-6, alcoxilo C1-6, o CF3, arilo C6-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6, acilo C1-6, alcoxilo C1-6, N-alquil C1-6-alquilo C1-6, CF3 o ciano, o heteroarilo C5-12, que puede estar opcionalmente sustituido con uno o más grupos, iguales o diferentes, seleccionados entre halógeno, alquilo C1-6, acilo C1-6, alcoxilo C1-6, N-alquil C1-6-alquilo C1-6, CF3 o ciano, o alquilo C1-6, el cual puede estar opcionalmente sustituido, R4 y R5 forman juntos un anillo de 5-8 miembros, que puede contener otros heteroátomos, y R6 representa el grupo alquilo C1-6, acilo C1-6, alquil C1-6-cicloalquilo C3-6, alquil C1-6-arilo C6-12, donde el grupo alquilo C1-6, acilo C1-6, alquil C1-6-cicloalquilo C3-6, alquil C1-6-arilo C6-12, que opcionalmente puede estar sustituido por uno o más grupos hidroxilo, metoxilo, etoxilo, iso-propoxilo, cloro, bromo, fluoro, ciano, metil-sulfonilo o amino-sulfonilo, y también sus isómeros, sus diastereómeros, sus enantiómeros y sus sales.Compounds of the general formula (1) wherein R 1 represents hydrogen, halogen, CF 3, C 3-6 cycloalkyl, which may optionally be saturated several times, or optionally may be substituted several times, or the C 1-6 alkyl group, C 1-6 aryl , C1-6 acyl, halo-C1-6-alkyl, C1-6 alkyl-C1-6 alkyl, C1-6 alkyl-C1-6 acyl, C1-6 acyl-C1-6 acyl, C1-6-aryl alkyl C1-6, C1-6 aryl-C1-6 alkyl or CF3, where the group C1-6 alkyl, C1-6 aryl, C1-6 acyl, halo-C1-6-alkyl, C1-6 alkyl-C1- alkyl 6, C1-6 alkyl C1-6 acyl, C1-6 acyl C1-6 acyl, C1-6 alkyl C1-6 aryl or C1-6 aryl C1-6 alkyl may be interrupted by one or more atoms of oxygen, sulfur or nitrogen, the same or different, or the sulfonyl C1-6-alkyl, sulfonamide, or cyano group, R2 represents halogen, CF3, C3-6 cycloalkyl, which may optionally be saturated several times, or optionally may be substituted several times, or the group C1-6 alkyl, C1-6 aryl, C1-6 acyl, halo-C1-6-alkyl, C1-6 alkyl C1-6, C1-6 alkyl C1-6 acyl, C1-6 acyl C1-6 acyl, C1-6 alkyl C1-6 aryl, C1-6 aryl C1-6 alkyl or CF3, where the alkyl group C1-6, C1-6 aryl, C1-6 acyl, halo-C1-6-alkyl, C1-6 alkyl-C1-6 alkyl, C1-6 alkyl-C1-6 acyl, C1-6 acyl-C1- acyl 6, C1-6 alkyl-C1-6 aryl or C1-6 aryl-C1-6 alkyl may be interrupted by one or more oxygen, sulfur or nitrogen atoms, the same or different, or the C1-6-alkyl sulfonyl group, sulfonamide, or cyano, R3 represents C6-12 aryl, which may be optionally substituted with one or more groups, the same or different, selected from halogen, C1-6 alkyl or C1-6 acyl, which may be optionally substituted in one or more positions, or with C1-6 alkoxy, hydroxyl, cyano, CO2-C1-6 alkyl, N- (C1-6 alkyl) 2, CO-NR4R5 or CF3, C5-12 heteroaryl, which may be optionally substituted with one or more groups, the same or different, selected from halogen, C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, hydroxyl, cyano, CO2-C1 alkyl -6, N- (C1-6 alkyl) 2, CO-NR4R5 or CF3 or C3-6 cycloalkyl, which may be optionally substituted with one or more groups, the same or different, selected from halogen, CF3, hydroxyl, cyano, CO2 -C1-6 alkyl, C1-6 alkyl, C1-6 acyl, N- (C1-6 alkyl) 2, CO-NR4R5 or C1-6 alkoxy, R4 represents hydrogen, C3-6 cycloalkyl, which may be optionally substituted with one or more groups, the same or different, selected from C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, or CF3, C6-12 aryl, which may be optionally substituted with one or more groups, same or different, selected among halogen, C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, N-C1-6 alkyl-C1-6 alkyl, CF3 or cyano, or C5-12 heteroaryl, which may be optionally substituted with one or more groups , same or different, selected from halogen, C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, N-C1-6 alkyl-C1-6 alkyl, CF3 or cyano, or C1-6 alkyl, which may be optionally substituted, R5 represents hydr Oxygen, C1-6 alkyl C3-6 cycloalkyl, which may be optionally substituted with one or more groups, the same or different, selected from C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, or CF3, C3- cycloalkyl 6, which may be optionally substituted with one or more groups, the same or different, selected from C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, or CF3, C6-12 aryl, which may be optionally substituted with one or more groups, the same or different, selected from halogen, C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, N- C1-6 alkyl-C1-6 alkyl, CF3 or cyano, or C5-12 heteroaryl, which may be optionally substituted with one or more groups, the same or different, selected from halogen, C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, N-C1-6 alkyl-C1-6 alkyl, CF3 or cyano, or alkyl C1-6, which may be optionally substituted, R4 and R5 together form a 5-8 membered ring, which may contain other heteroatoms, and R6 represents the C1-6 alkyl group, C1-6 acyl, C1-6 alkyl C3-6 cycloalkyl, C1-6 alkyl-C6-12 aryl, where the group C1-6 alkyl, C1-6 acyl, C1-6 alkyl C3-6 alkyl, C1-6 alkyl-C6 aryl -12, which may optionally be substituted by one or more hydroxyl, methoxy, ethoxy, iso-propoxy, chloro, bromo, fluoro, cyano, methyl sulfonyl or amino sulfonyl groups, and also their isomers, their diastereomers, their enantiomers and Your salts Methods for making them, medicines containing them and intermediaries of the general formula (2) where R1, R2, R3 and R6 have the meanings indicated above, and R7 can be H or a C1-6 alkyl radical, of the general formula ( 7) where R1, R2 and R7 have the meanings indicated above, and of the general formula (9) where R1, R2, R6 and R7 have the meanings indicated above. Claim 1: Compounds of the general formula (1) wherein R 1 represents hydrogen, halogen, CF 3, C 3-6 cycloalkyl, which may optionally be saturated several times, or optionally may be substituted several times, or the C 1-6 alkyl group, aryl C1-6, C1-6 acyl, halo-C1-6-alkyl, C1-6 alkyl-C1-6 alkyl, C1-6 alkyl-C1-6 acyl, C1-6 acyl-C1-6 acyl, C1- alkyl 6-aryl C1-6, aryl C1-6-alkyl C1-6 or CF3, where the group C1-6 alkyl, aryl C1-6, acyl C1-6, halo-C1-6-alkyl, alkyl C1-6- C 1-6 alkyl, C 1-6 alkyl-C 1-6 acyl, C 1-6 acyl-C 1-6 acyl, C 1-6 alkyl-C 1-6 aryl or C 1-6 aryl-C 1-6 alkyl may be interrupted by one or more oxygen, sulfur or nitrogen atoms, the same or different, or the group C1-6 sulfonyl-alkyl, sulfonamide, or cyano, R2 represents halogen, CF3, C3-6 cycloalkyl, which may optionally be saturated several times, or optionally be substituted several times, or the group C1-6 alkyl, aryl C1-6, acyl C1-6, halo-C1-6-alkyl, to C1-6 alkyl C1-6 alkyl, C1-6 alkyl C1-6 acyl, C1-6 acyl C1-6 acyl, C1-6 alkyl C1-6 aryl, C1-6 aryl C1-6 alkyl or CF3, where the group C1-6 alkyl, C1-6 aryl, C1-6 acyl, halo-C1-6-alkyl, C1-6 alkyl-C1-6 alkyl, C1-6 alkyl-C1-6 acyl, C1 acyl -6-C 1-6 acyl, C 1-6 alkyl-C 1-6 aryl or C 1-6 aryl-C 1-6 alkyl may be interrupted by one or more oxygen, sulfur or nitrogen atoms, the same or different, or the sulfonyl group C1-6-alkyl, sulfonamide, or cyano, R3 represents C6-12 aryl, which may be optionally substituted with one or more groups, the same or different, selected from halogen, C1-6 alkyl or C1-6 acyl, which may be optionally substituted in one or more positions, or with C1-6 alkoxy, hydroxyl, cyano, CO2-C1-6 alkyl, N- (C1-6 alkyl) 2, CO-NR4R5 or CF3, C5-12 heteroaryl, which may be optionally substituted with one or more groups, the same or different, selected from halogen, C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, hydroxyl, cia no, CO2-C1-6 alkyl, N- (C1-6 alkyl) 2, CO-NR4R5 or CF3 or C3-6 cycloalkyl, which may be optionally substituted with one or more groups, the same or different, selected from halogen, CF3 , hydroxyl, cyano, CO2-C1-6 alkyl, C1-6 alkyl, C1-6 acyl, N- (C1-6 alkyl) 2, CO-NR4R5 or C1-6 alkoxy, R4 represents hydrogen, C3-6 cycloalkyl, which may be optionally substituted with one or more groups, the same or different, selected from C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, or CF3, C6-12 aryl, which may be optionally substituted with one or more groups , same or different, selected from halogen, C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, N-C1-6 alkyl-C1-6 alkyl, CF3 or cyano, or C5-12 heteroaryl, which may optionally be substituted with one or more groups, the same or different, selected from halogen, C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, N-C1-6 alkyl-C1-6 alkyl, CF3 or cyano, or C1- alkyl 6, which may be optionally substituted, R 5 represents hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, which may be optionally substituted with one or more groups, the same or different, selected from C 1-6 alkyl, C 1-6 acyl, C 1-6 alkoxy, or CF 3, cycloalkyl. C3-6, which may be optionally substituted with one or more groups, the same or different, selected from C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, or CF3, C6-12 aryl, which may be optionally substituted with one or more groups, the same or different, selected from halogen, C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, N-C1-6 alkyl-C1-6 alkyl, CF3 or cyano, or C5-12 heteroaryl, which may be optionally substituted with one or more groups, the same or different, selected from halogen, C1-6 alkyl, C1-6 acyl, C1-6 alkoxy, N-C1-6 alkyl-C1-6 alkyl, CF3 or cyano, or C1-6 alkyl, which may be optionally substituted, R4 and R5 together form a 5-8 membered ring, which may contain other heteroatoms, and R6 represents the alkyl group C1-6, C1-6 acyl, C1-6 alkyl C3-6 cycloalkyl, C1-6 alkyl-C6-12 aryl, wherein the group C1-6 alkyl, C1-6 acyl, C1-6 alkyl C3- cycloalkyl 6, C1-6 alkyl-C6-12 aryl, which may optionally be substituted by one or more hydroxyl, methoxy, ethoxy, iso-propoxy, chloro, bromine, fluoro, cyano, methyl sulfonyl or amino sulfonyl groups, and also its isomers, its diastereomers, its enantiomers and its salts.

ARP070101194A 2006-03-23 2007-03-23 INDOLES DERIVED FROM SOLUBLE CYCLING ADENYLATE, PROCEDURE FOR THE PREPARATION AND MEDICINES CONTAINING THEM. AR063661A1 (en)

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