AR066379A1 - CARBOXILIC ACID AMIDAS ITS PREPARATION AND ITS USE AS MEDICATIONS - Google Patents

CARBOXILIC ACID AMIDAS ITS PREPARATION AND ITS USE AS MEDICATIONS

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AR066379A1
AR066379A1 ARP080101851A ARP080101851A AR066379A1 AR 066379 A1 AR066379 A1 AR 066379A1 AR P080101851 A ARP080101851 A AR P080101851A AR P080101851 A ARP080101851 A AR P080101851A AR 066379 A1 AR066379 A1 AR 066379A1
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Argentina
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alkyl
group
amino
substituted
alkylcarbonyl
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ARP080101851A
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Spanish (es)
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Wolfgang Wienen
Kai Gerlach
Annette Schuler-Metz
Herbert Nar
George Dahmann
Henning Priepke
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Boehringer Ingelheim Int
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Publication of AR066379A1 publication Critical patent/AR066379A1/en

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen 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
    • C07D513/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Reivindicacion 1: Compuestos de la formula general (1) en los cuales D representa un sistema de anillos bicíclico sustituido de la formula (2a), (2b) o (2c) en donde K1 y K4, en cada caso independientemente uno de otro, significan un enlace, un grupo -CH2-, -CHR2a-, -CR2bR2c o un grupo -C(O), y en donde R2a/R2b/R2c, en cada caso de modo independiente entre sí, significan un átomo de fluor, un grupo hidroxi, alquil C1-5-oxi, amino, alquil C1-5-amino, di-alquil C1-5-amino, cicloalquilen C3-5-imino, alquil C1-5-carbonilamino, un grupo alquilo C1-5, que puede estar sustituido con 1-3 átomos de fluor, un grupo hidroxi-alquilo C1-5, alquil C1-5-oxi-alquilo C1-5, amino-alquilo C1-5, alquil C1-5-amino-aIquilo C1-5, di-alquil C1-5-amino-alquilo C1-5, cicloalquilen C4-7-imino-alquilo C1-5, carboxialquilo C0-5, alquil C1-5-oxicarbonil-alquilo C0-5, aminocarbonil-alquilo C0-5, alquil C1-5-aminocarbonil-alquilo C0-5, di-alquil C1-5-aminocarbonil-alquilo C0-5 o un grupo cicloalquilen C4-7- iminocarbonil-alquilo C0-5, en donde al mismo tiempo los dos radicales R2b/R2c no pueden estar unidos al átomo de carbono del anillo a través de un heteroátomo, a excepcion de que -C(R2bR2c)- corresponda a un grupo -CF2, o R2a significa un grupo fenilo sustituido con fluor, cloro , bromo, metilo, metoxi, amino o nitro o heteroarilo monocíclico, o dos radicales R2b/R2c, junto con el átomo de carbono del anillo, pueden formar un carbociclo saturado de 3, 4, 5, 6 o 7 miembros o un anillo de ciclopenteno, ciclohexeno, oxetano, azetidina, tietano, tetrahidrofurano, pirrolidina, tetrahidrotiofeno, tetrahidropirano, piperidina, sulfuro de pentametileno, hexametilenimina, 1,3-dioxolano, 1,4-dioxano, hexahidropiridazina, piperazina, tiomorfolina, morfolina, 2-imidazolidinona, 2-oxazolidinona, tetrahidro-2(1H)-pirimidinona o [1,3]-oxazinan-2-ona, en donde sus grupos metileno pueden estar sustituidos con 1-2 grupos alquilo C1-3 o CF3, y/o sus grupos metileno, en la medida en que no estén unidos a un heteroátomo, pueden estar sustituidos con 1-2 átomos de fluor, y/o en el que un grupo -CH2, junto a un átomo de N, puede estar reemplazado por un grupo -CO, y/o sus grupos imino pueden estar sustituidos en cada caso con un grupo alquilo C1-3 o alquil C1-3-carbonilo, y/o en el que el átomo de azufre puede estar oxidado en un grupo sulfoxido o sulfona, K2 y K3, en cada caso independientemente uno de otro, significan un grupo -CH2, -CHR6a, -CR6bR6c o un grupo -C(O), en donde R6a/R6b/R6c en cada caso, de modo independiente entre sí, significan un grupo alquilo C1-5, que puede estar sustituido con 1-3 átomos de fluor, un grupo hidroxi-alquilo C1-5, alquil C1-5-oxi-alquilo C1-5, amino-alquilo C1-5, alquil C1-5-amino-alquilo C1-5, di-alquil C1-5-amino-alquilo C1-5, cicloalquilen C4-7-imino-alquilo C1-5, carboxi-alquilo C0-5, alquil C1-5-oxicarbonil-alquilo C0-5, aminocarbonil-alquilo C0-5, alquil C1-5-aminocarbonil-alquilo C0-5, di-alquil C1-5-aminocarbonil-alquilo C0-5 o un grupo cicloalquilen C4-7-iminocarbonil-alquilo C0-5, o dos radicales R6b/R6c, junto con el átomo de carbono del anillo, pueden formar un carbociclo saturado de 3, 4, 5, 6 o 7 miembros, o un anillo de ciclopenteno, ciclohexeno, oxetano, azetidina, tietano, tetrahidrofurano, pirrolidina, tetrahidrotiofeno, tetrahidropirano, piperidina, sulfuro de pentametileno, hexametilenimino, hexahidropiridazina, tetrahidro-2(1H)pirimidinona, [1,3]oxazinan-2-ona, en donde sus grupos metileno pueden estar sustituidos con 1-2 grupos alquilo C1-3 o CF3, y/o sus grupos metileno, en la medida en que no estén unidos a un heteroátomo, pueden estar sustituidos con 1-2 átomos de fluor, y/o en el que un grupo -CH2, junto a un átomo de nitrogeno, lo puede estar reemplazado por un grupo -CO, y/o sus grupos imino pueden estar sustituidos en cada caso con un grupo alquilo C1-3 o alquil C1-3-carbonilo, y/o en el que el átomo de azufre puede estar oxidado en un grupo sulfoxido o sulfona, con la condicion de que un heteroátomo incorporado por R6b o R6c no pueda ser separado por solo un átomo de carbono de X en la formula (1), y en la formula (2a) o (2b) o (2c) pueden estar presentes en total como máximo cuatro radicales seleccionados de R2a, R2b, R2c, R6a, R6b y R6c, y X significa un átomo de oxigeno o de azufre, un grupo CF2, sulfeno, sulfona o un grupo NR1, en el que R1 significa un átomo de hidrogeno o un grupo hidroxi, alquil C1-3-oxi, amino, alquil C1-3-amino, di-alquil C1-3-amino, un grupo alquilo C1-5, alquenil C2-5-CH2-, alquinil C2-5-CH2-, cicloalquilo C3-6, cicloalquenilo C4-6, oxetan-3-ilo, tetrahidrofuran-3-ilo, bencilo, alquil C1-5-carbonilo, trifluorometilcarbonilo, cicloalquil C3-6-carbonilo, alquil C1-5-sulfonilo, cicloalquil C3-6-sulfonilo, aminocarbonilo, alquil C1-5-aminocarbonilo, di-alquil C1-5-aminocarbonilo, alquil C1-5-oxicarbonilo, cicloalquilen C47-iminocarbonilo, en donde los grupos metileno y metilo que se encuentran en los grupos precedentemente mencionados pueden estar sustituidos adicionalmente con un grupo alquilo C1-3, carboxi, alcoxi C1-5-carbonilo, o con un grupo hidroxi, alquiloxi C1-5, amino, alquil C1-5-amino, dialquil C1-5-amino o cicloalquilen C4-7-imino, en la medida en que los grupos metileno o metilo no estén unidos directamente a un heteroátomo del grupo O, N o S, y/o uno a tres átomos de hidrogeno pueden estar reemplazados por átomos de fluor, en la medida en que los grupos metileno o metilo no estén unidos directamente a un heteroátomo del grupo O, N o S, y en el que A1 significa N o CR10, A2 significa N o CR11, A3 significa N o CR12; A4 significa N o CR12, A5 significa NH, azufre u oxigeno, en donde R10, R11 y R12, en cada caso independientemente uno de otro, significan un átomo de hidrogeno, fluor, cloro, bromo o yodo, o un grupo fenilo, alquilo C1-5, CF3, alquenilo C2-5, alquinilo C2-5, un grupo ciano, carboxi, alquil C1-5-oxicarbonilo, hidroxi, alquil C1-5-oxi, CF3O, CHF2O, CH2FO, amino, alquil C1-5-amino, di-alquil C1-5-amino o cicloalquilen C4-7-imino y R3 significa un átomo de hidrogeno, un grupo alquenilo C2-3 o alquinilo C2-3 o grupo alquilo C1-6 de cadena lineal o ramificado, en el que los átomos hidrogeno pueden estar reemplazados, en su totalidad o en parte, por átomos de fluor, y que, eventualmente, está sustituido con un grupo nitrilo, hidroxi, un grupo alcoxi C1-5, en el que los átomos de hidrogeno pueden estar reemplazados en su totalidad o en parte por átomos de fluor, un grupo aliloxi, propargiloxi, benciloxi, alquil C1-5-carboniloxi, alquiloxi C1-5-carboniloxi, carboxi-alquiloxi C1-3, alquiloxi C1-5-carbonil-alquiloxi C1-3, alquiloxi C1-8-carbonilamino, mercapto, alquil C1-3-sulfanilo, alquil C1-3-sulfinilo, alquil C1-3-sulfonilo, alquil C1-3-carbonilamino-alquil C1-3-sulfanilo, alquil C1-3-carbonilamino-alquil C1-3-sulfinilo, alquil C1-3-carbonilamino-alquil C1-3-sulfonilo, carboxi, alquiloxi C1-3-carbonilo, aliloxicarbonilo, propargiloxicarbonilo, benciloxicarbonilo, aminocarbonilo, alquil C1-3-aminocarbonilo, di-alquil C1-3-aminocarbonilo, cicloalquilen C3-6-iminocarbonilo, aminosulfonilo, alquil C1-3-aminosulfonilo, di-alquil C1-3-aminosulfonilo, cicloalquilen C3-6-iminosulfonilo, amino, alquil C1-3-amino, di-alquil C1-3-amino, alquil C1-5-carbonilamino, alquil C1-3-sulfonilamino, N-alquil C1-3-sulfonil-alquil C1-3-amino, cicloalquil C3-6-carbonilamino, aminocarbonilamino, alquil C1-3-aminocarbonilamino, di-alquil C1-3-aminocarbonilamino-, un grupo cicloalquileniminocarbonilamino de 4 a 7 miembros, benciloxicarbonilamino, fenilcarbonilamino o guanidino, un grupo carboxi, aminocarbonilo, alquil C1-4-aminocarbonilo, cicloalquil C3-6-aminocarbonilo, di-alquil C1-3-aminocarbonilo, alcoxi C1-4-carbonilo, cicloalquilen C4-6-iminocarbonilo, un grupo fenilo o heteroarilo, fenilcarbonil-alquilo C1-3, fenil-alquilo C1-3 o heteroaril-alquilo C1-3, que en la parte de fenilo o heteroarilo está sustituido, eventualmente una o más veces, con átomos de fluor, cloro o bromo, un grupo alquilo C1-3, amino, alquil C1-3-amino, di-alquil C1-3-amino, hidroxi, alquiloxi C1-4, mono-, di- o tri-fluorometoxi, benciloxi, carboxi-alquiloxi C1-3, alquiloxi C1-3-carbonil-alquiloxi C1-3, aminocarbonil-alquiloxi C1-3, alquil C1-3-aminocarbonil-alquiloxi C1-3, di-alquil C1-3-aminocarbonil-alquiloxi C1-3, un grupo cicloalquileniminocarbonil-alcoxi C1-3 de 4 a 7 miembros, carboxi, alquiloxi C1-3-carbonilo o alquiloxi C1-3-carbonilamino, un grupo cicloalquilo, cicloaquilenimino, cicloalquil-alquilo C1-3 o cicloalquilenimino-alquilo C1-3 de 3 a 7 miembros, en el que en la parte cíclica un grupo metileno puede estar reemplazado por un grupo -NH, eventualmente sustituido con un grupo alquilo C1-3 o alquil C1-3-carbonilo o un átomo de oxígeno y en el que, adicionalmente, un grupo metileno vecino a un grupo -NH, -Nalquil C1-3-carbonilo o -Nalquilo C1-3 puede estar reemplazado en cada caso por un grupo carbonilo o sulfonilo, con la condicion de que esté excluido un grupo cicloalquilenimino definido como antes, en el que dos átomos de nitrogeno están separados uno de otro por un grupo -CH2, R4 representa un átomo de hidrogeno o un grupo alquilo C1-3 o R3 y R4 forman, junto con el átomo de carbono al que están unidos, un grupo cicloalquilo C3-7, en donde uno de los grupos metileno del grupo cicloalquilo C3-7 puede estar reemplazado por un grupo imino, alquil C1-3-imino, acilimino o sulfonilimino, R5 representa un átomo de hidrogeno o un grupo alquilo C1-3, B un grupo de formulas (3) en la cual n representa el numero 1 o 2, R7 representa un átomo de hidrogeno o un grupo alquilo C1-3, hidroxi, alquiloxi C1-5-carbonilo, carboxi-alquilo C1-3, alquiloxi C1-3-carbonil-alquilo C1-3, amino o alquil C1-3-amino y R8, independientemente uno de otro, representan un átomo de hidrogeno, fluor, cloro, bromo o yodo, un grupo alquilo C1-3, en el que los átomos de hidrogeno pueden estar reemplazados, en su totalidad o en parte, por átomos de fluor, un grupo alquenilo C2-3 o alquinilo C2-3, un grupo hidroxi, alcoxi CClaim 1: Compounds of the general formula (1) in which D represents a substituted bicyclic ring system of the formula (2a), (2b) or (2c) wherein K1 and K4, in each case independently of each other, they mean a bond, a group -CH2-, -CHR2a-, -CR2bR2c or a group -C (O), and where R2a / R2b / R2c, in each case independently of each other, means a fluorine atom, a hydroxy group, C1-5-oxy alkyl, amino, C1-5-amino alkyl, di-C1-5-alkyl alkyl, C3-5 cycloalkylene, C1-5 alkylcarbonylamino, a C1-5 alkyl group, which it may be substituted with 1-3 fluorine atoms, a hydroxy-C1-5 alkyl, C1-5 alkyl-C1-5 alkyl, amino C1-5 alkyl, C1-5 alkyl-amino-C1-5 alkyl group , di-C1-5 alkyl-C1-5 alkyl-alkyl, C4-7 cycloalkylene-C1-5 alkyl, C0-5 carboxyalkyl, C1-5 alkyl-oxycarbonyl-C0-5 alkyl, aminocarbonyl-C0-5 alkyl , C1-5-alkylcarbonyl-C0-5 alkyl, di-C1-5-alkylcarbonyl-C0-5 alkyl or a C4-7 -imino cycloalkylene group C0-5 carbonyl-alkyl, wherein at the same time the two radicals R2b / R2c cannot be attached to the ring carbon atom through a heteroatom, except that -C (R2bR2c) - corresponds to a group -CF2 , or R2a means a phenyl group substituted with fluorine, chlorine, bromine, methyl, methoxy, amino or nitro or monocyclic heteroaryl, or two radicals R2b / R2c, together with the carbon atom of the ring, can form a saturated carbocycle of 3, 4, 5, 6 or 7 members or a ring of cyclopentene, cyclohexene, oxetane, azetidine, tiethane, tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, piperidine, pentamethylene sulfide, hexamethyleneimine, 1,3-dioxolane, 1,4-dioxane, hexahydropyridazine, piperazine, thiomorpholine, morpholine, 2-imidazolidinone, 2-oxazolidinone, tetrahydro-2 (1H) -pyrimidinone or [1,3] -oxazinan-2-one, where their methylene groups may be substituted with 1-2 groups C1-3 alkyl or CF3, and / or its methylene groups, insofar as they are not attached to a heteroatom, they may be substituted with 1-2 fluorine atoms, and / or in which a -CH2 group, together with an N atom, may be replaced by a -CO group, and / or their imino groups may be substituted in each case with a C1-3 alkyl or C1-3 alkylcarbonyl group, and / or in which the sulfur atom may be oxidized in a sulfoxide or sulfone group, K2 and K3, in each case independently of each other , they mean a group -CH2, -CHR6a, -CR6bR6c or a group -C (O), where R6a / R6b / R6c in each case, independently of each other, means a C1-5 alkyl group, which can be substituted with 1-3 fluorine atoms, a hydroxy-C1-5 alkyl, C1-5 alkyl-C1-5 alkyl, amino C1-5 alkyl, C1-5 alkyl-amino-C1-5 alkyl group, di- C1-5 alkyl-C1-5 alkyl, C4-7 cycloalkylene-C1-5 alkyl, carboxy-C0-5 alkyl, C1-5 alkyl-oxycarbonyl-C0-5 alkyl, aminocarbonyl-C0-5 alkyl, C1-5-alkylcarbonyl-C0-5 -alkyl, di-C1-5 -alkylcarbonyl-C0-5 -alkyl or a group C4-7 cycloalkylene-iminocarbonyl-C0-5 alkyl, or two radicals R6b / R6c, together with the carbon atom of the ring, can form a saturated carbocycle of 3, 4, 5, 6 or 7 members, or a cyclopentene ring , cyclohexene, oxetane, azetidine, thiethane, tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, piperidine, pentamethylene sulfide, hexamethyleneimino, hexahydropyridazine, tetrahydro-2 (1H) pyrimidinone, [1,3] oxazinan-2-sus-groups where methylene may be substituted with 1-2 C1-3 alkyl groups or CF3, and / or their methylene groups, insofar as they are not bound to a heteroatom, may be substituted with 1-2 fluorine atoms, and / or in that a -CH2 group, together with a nitrogen atom, can be replaced by a -CO group, and / or their imino groups can be substituted in each case with a C1-3 alkyl or C1-3 alkylcarbonyl group , and / or in which the sulfur atom may be oxidized into a sulfoxide or sulfone group, with the proviso that a he The thermoatome incorporated by R6b or R6c cannot be separated by only one carbon atom of X in the formula (1), and in the formula (2a) or (2b) or (2c) a maximum of four selected radicals can be present in total of R2a, R2b, R2c, R6a, R6b and R6c, and X means an oxygen or sulfur atom, a CF2 group, sulfen, sulfone or an NR1 group, in which R1 means a hydrogen atom or a hydroxy group, C1-3-oxy alkyl, amino, C1-3-amino alkyl, di-C1-3-amino alkyl, a C1-5 alkyl group, C2-5-CH2- alkenyl, C2-5-CH2- alkynyl, C3 cycloalkyl -6, C4-6 cycloalkenyl, oxetan-3-yl, tetrahydrofuran-3-yl, benzyl, C1-5 alkylcarbonyl, trifluoromethylcarbonyl, C3-6cycloalkylcarbonyl, C1-5 alkyl sulfonyl, C3-6 cycloalkyl sulfonyl, aminocarbonyl, C1-5-alkylcarbonyl, di-C1-5-alkylcarbonyl, C1-5-alkylcarbonyl, C47-iminocarbonyl cycloalkylene, wherein the methylene and methyl groups found in the aforementioned groups may be further substituted with a C1-3 alkyl, carboxy, C1-5 alkoxycarbonyl group, or with a hydroxy, C1-5 alkyloxy, amino, C1-5-amino alkyl, C1-5-dialkyl or C4- cycloalkylene group 7-imino, to the extent that the methylene or methyl groups are not directly linked to a heteroatom of the group O, N or S, and / or one to three hydrogen atoms may be replaced by fluorine atoms, to the extent that that the methylene or methyl groups are not directly linked to a heteroatom of the group O, N or S, and in which A1 means N or CR10, A2 means N or CR11, A3 means N or CR12; A4 means N or CR12, A5 means NH, sulfur or oxygen, where R10, R11 and R12, in each case independently of each other, mean a hydrogen, fluorine, chlorine, bromine or iodine atom, or a phenyl, alkyl group C1-5, CF3, C2-5 alkenyl, C2-5 alkynyl, a cyano group, carboxy, C1-5-oxycarbonyl alkyl, hydroxy, C1-5-oxy alkyl, CF3O, CHF2O, CH2FO, amino, C1-5 alkyl -amino, di-C1-5-amino or C4-7 -imino cycloalkylene and R3 means a hydrogen atom, a C2-3 alkenyl group or C2-3 alkynyl or straight or branched chain C1-6 alkyl group, in that the hydrogen atoms can be replaced, in whole or in part, by fluorine atoms, and which, if necessary, is substituted with a nitrile group, hydroxy, a C1-5 alkoxy group, in which the hydrogen atoms can be substituted in whole or in part by fluorine atoms, an allyloxy, propargiloxy, benzyloxy, C1-5 alkylcarbonyloxy, C1-5 alkyloxycarbonyloxy, carboxy C1-3 alkyloxy, alky loxy C1-5-carbonyl-C1-3 alkyloxy, C1-8 alkyloxycarbonylamino, mercapto, C1-3 alkyl sulfanyl, C1-3 alkyl sulfinyl, C1-3 alkyl sulfonyl, C1-3 alkylcarbonylamino alkyl C1-3-sulfanyl, C1-3 alkylcarbonylamino-C1-3-sulfinyl alkyl, C1-3 alkylcarbonylamino-C1-3-sulfonyl alkyl, carboxy, C1-3 alkyloxycarbonyl, allyloxycarbonyl, propargiloxycarbonyl, benzyloxycarbonyl, aminocarbonyl , C1-3-alkylcarbonyl, di-C1-3-aminocarbonyl, C3-6-iminocarbonyl, aminosulfonyl, C1-3-aminosulfonyl, di-C1-3-aminosulfonyl, C3-6-iminosulfonyl, cycloalkylene, amino , C1-3-amino alkyl, di-C1-3-amino alkyl, C1-5 alkylcarbonylamino, C1-3 alkyl sulfonylamino, N-C1-3 alkyl sulfonyl-C1-3-alkyl alkyl, C3- cycloalkyl 6-carbonylamino, aminocarbonylamino, C1-3-alkylcarbonylamino, di-C1-3-aminocarbonylamino-, a 4- to 7-membered cycloalkyleneiminocarbonylamino group, benzyloxycarbonylamino, phenylcarbonylamino or guanidino, a carb group oxy, aminocarbonyl, C 1-4 alkylcarbonyl, C 3-6 cycloalkylcarbonyl, di C 1-3 alkylcarbonyl, C 1-4 alkoxycarbonyl, C 4-6 iminocarbonyl cycloalkylene, a phenyl or heteroaryl group, phenylcarbonyl alkyl C1-3, phenyl-C1-3 alkyl or heteroaryl-C1-3 alkyl, which in the phenyl or heteroaryl part is substituted, optionally one or more times, with fluorine, chlorine or bromine atoms, a C1-3 alkyl group , amino, C1-3-alkyl, di-C1-3-alkyl, hydroxy, C1-4 alkyloxy, mono-, di- or tri-fluoromethoxy, benzyloxy, carboxy-C1-3 alkyloxy, C1-3 alkyloxy- C1-3 carbonyl-alkyloxy, C1-3 aminocarbonyl-C1-3 alkyl, C1-3-aminocarbonyl-C1-3 alkyloxy, di-C1-3-aminocarbonyl-C1-3 alkyloxy group, a cycloalkyleneiminocarbonyl-C1-3 alkoxy group of 4 to 7 members, carboxy, C1-3 alkyloxycarbonyl or C1-3 alkyloxycarbonylamino, a cycloalkyl, cycloalkylimino, cycloalkyl-C1-3alkyl or cycloalkyleneimino-C1-3alkyl group of 3 to 7 members, wherein in the part cit Clicking on a methylene group may be replaced by a -NH group, optionally substituted with a C1-3 alkyl or C1-3 alkylcarbonyl group or an oxygen atom and in which, additionally, a methylene group neighboring a -NH group , -C1-3alkyl-carbonyl or -C1-3alkyl can be replaced in each case by a carbonyl or sulfonyl group, with the proviso that a cycloalkyleneimino group defined as before is excluded, in which two nitrogen atoms are separated from each other by a group -CH2, R4 represents a hydrogen atom or a C1-3 or R3 alkyl group and R4 form, together with the carbon atom to which they are attached, a C3-7 cycloalkyl group, wherein one of the methylene groups of the C3-7 cycloalkyl group may be replaced by an imino, C1-3-alkyl, acylimino or sulfonylimino group, R5 represents a hydrogen atom or a C1-3 alkyl group, B a group of formulas (3) in which n represents the number 1 or 2, R7 represents a hydrogen atom or a C1-3 alkyl, hydroxy, C1-5 alkyloxycarbonyl, carboxy C1-3 alkyl, C1-3 alkyloxycarbonyl C1-3 alkyl, amino or C1-3alkylamino and R8 group, independently of one of another, they represent a hydrogen, fluorine, chlorine, bromine or iodine atom, a C1-3 alkyl group, in which the hydrogen atoms may be replaced, in whole or in part, by fluorine atoms, a C2 alkenyl group -3 or C2-3 alkynyl, a hydroxy group, C alkoxy

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