CO5080805A1 - NEW ASYMETRICALLY SUBSTITUTED CARBOXYLIC ACID DERIVATIVES, THEIR OBTAINING AND USE AS ANTAGONISTS OF ET [sub A] / ET [sub B] MIXED RECEIVERS - Google Patents

NEW ASYMETRICALLY SUBSTITUTED CARBOXYLIC ACID DERIVATIVES, THEIR OBTAINING AND USE AS ANTAGONISTS OF ET [sub A] / ET [sub B] MIXED RECEIVERS

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CO5080805A1
CO5080805A1 CO99013467A CO99013467A CO5080805A1 CO 5080805 A1 CO5080805 A1 CO 5080805A1 CO 99013467 A CO99013467 A CO 99013467A CO 99013467 A CO99013467 A CO 99013467A CO 5080805 A1 CO5080805 A1 CO 5080805A1
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alkyl
phenyl
optionally substituted
alkylthio
alkoxy
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CO99013467A
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Spanish (es)
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Wilhelm Amberg
Rolf Jansen
Klinge Dagmar
Hartmut Riechers
Stefan Herms
Raschack Manfred
Unger Unger
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Basf Ag
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms

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Abstract

Derivados de ácido carboxílico de la fórmula I<EMI FILE="99013467_1" ID="1" IMF=JPEG >En la que los sustituyentes tienen los significados siguientes:R1 tetrazol o un grupo<EMI FILE="99013467_2" ID="2" IMF=JPEG >Ra) un radical OR7 , donde R7 significa:hidrógeno, el catión de un metal alcalino, el catíón de un metal alcalinotérreo o un ión amonio fisiológicamente tolerado;C3-C8-cicloalquilo, C1-C8-alquilo,CH2-fenilo eventualmente sustituido,Un grupo C3-C6-alquenilo o un grupo C3-C6-alquinilo eventualmente sustituido, o fenilo eventualmente sustituido. un heteroátomo de 5 miembros ligado por vía de un átomo de nitrógenoun grupo<EMI FILE="99013467_3" ID="3" IMF=JPEG >Donde k puede adoptar los valores 0,1 y 2, p los valores 1, 2, 3 y 4 y R8 significaC1-C4-alquilo, C3-C8-cicloalquilo, C3-C6-alquinilo o fenilo eventualmente sustituido.d) un radical<EMI FILE="99013467_4" ID="4" IMF=JPEG >Donde R9 significa:C1-C4-alquilo, C3-C6-alquinilo, C3-C8-cicloalquilo, C1-C4-halógenoalquilo, pudiendo estos radicales llevar un radical C1-C4-alcoxi, C1-C4-alquiltio y/o un radical fenilo;- 2 -e) un grupo<EMI FILE="99013467_5" ID="5" IMF=JPEG >Pudiendo R13 y R14 ser idénticos o diferentes y tener los significados siguientes:Hidrógeno, C1-C8-alquilo, C3-C8-cicloalquilo, C3-C8-alquenilo,C3-C8-alquinilo, bencilo, fenilo, eventualmente sustituidoO R13 y R14 forman juntos una cadena de C4-C7-alquileno cerrada formando un anillo, eventualmente sustituida, y que puede contener un heteroátomo, oR2 hidrógeno, hidroxi, NH2, NH(C1-C4-alquilo), N(C1-C4-alquilo)2, halógeno, C1-C4-alquilo C2-C4-alquenilo, C2-C4-alquinilo, C1-C4-hidroxialquilo, C1-C4-halógenoalquilo, C1-C4-alcoxi, C1-C4-halógenoalcoxi o C1-C4-alquiltio, o CR2 está ligado con CR10 en la forma abajo indicada, formando un anillo de 5 ó 6 miembros. a X nitrógeno o metino.Y nitrógeno o metino.Z nitrógeno o CR10, significado R10 hidrógeno, hidroxi, C1-C4 -halógenoalquilo o C1-C4-alquilo, o CR10 forma junto con CR2 o CR3 un anillo de alquileno o alquenileno de 5 ó 6 miembros, que puede estar eventualmente sustituido, y donde cada vez uno o varios grupos metileno pueden estar sustituidos por oxígeno, azufre, -NH o N(C1-C4-alquilo)2 .R3 hidrógeno, hidroxi, NH2, NH(C1-C4-alquilo), N(C1-C4-alquilo)2, halógeno, C1-C4-alquilo, C2-C4-alquenilo, C2-C4-alquinilo, C1-C4-halógenoalquilo, C1-C4-alcoxi, C1-C4-halógenoalcoxi, C1-C4-hidroxialquilo, C1-C4-alquiltio, o CR3 está ligado con CR10, en la forma arriba indicada, formando un anillo de cinco o seis miembros.R4 C1-C4-alquilo, C2-C4-alquenilo o C2-C4-alquinilo, eventualmente sustituidoR5 fenilo o naftilo, eventualmente sustituido, o fenilo o naftilo, que está ligado en la posición orto por vía de un enlace directo, un grupo metileno, etileno o etenileno, un átomo de oxígeno o de azufre o un grupo SO2 , NH o N-alquilo con R4 C3-C8-cicloalquilo eventualmente sustituido;R6 C3-C8-cicloalquilo eventualmente sustituido; fenilo o naftilo, que en cada caso pueden llevar uno o varios de los radicales siguientes; halógeno, R15, nitro, mercapto, carboxi, ciano, hidroxi, amino, C1-C4-alquilo, C2-C4-alquenilo, C2-C4-alquinilo, C3-C6-alqueniloxi, C1-C4-halógenoalquilo, C3-C6-alquiniloxi, C1-C4-alquilcarbonilo, C1-C4-alcoxicarbonilo, C1-C4-alcoxi, C1-C4-halógenoalcoxi, fenoxi, C1-C4-alquiltio, NH(C1-C4-alquilo), N(C1-C4-alquilo)2, dioxometileno, dioxoetileno o fenilo, que puede estar mono o polisustituido, P.ej. mono a trisustituido por halógeno, nitro ciano, C1-C4-alquilo, C1-C4-halógenoalquilo, C1-C4-alcoxi, C1-C4-halógenoalcoxi o C1-C4-alquiltio, siendo preciso, que cuando R6 es un radical fenilo sin sustituir, entonces R2 y R3 no pueden significar simultáneamente OCH3;un heteroaromático de cinco o seis miembros, que contiene de uno a tres átomos de nitrógeno y/o un átomo de azufre o de oxígeno, que puede llevar uno a cuatro átomos de halógeno y/o uno de los radicales siguiente:C1-C4-alquilo, C2-C4-alquenilo, C1-C4-halógenoalquilo, C1-C4-alcoxi, C1-C4-halógenoalcoxi, C1-C4-alquiltio, fenilo o fenoxi, pudiendo los radicales fenilo a su vez llevar uno de cinco átomos de halógeno y/o uno a tres de los radicales siguientes: C1-C4-alquilo, C1-C4-halógenoalquilo, C1-C4-alcoxi, C1-C4-halógenoalcoxi y/o C1-C4-alquiltio;R15 C1-C4-alquilo, C1-C4-alquiltio, C1-C4-alcoxi, que llevan uno de los radicales siguientes hidroxi, carboxi, amino, NH(C1-C4-alquilo), N(C1-C4-alquilo)2, carboxamida o CON(C1 -C4-alquilo)2,W azufre u oxígeno;Q un espaciador, que en su longitud equivale a una cadena de 2 a 4 átomos de carbono,Así como sus sales fisiológicamente toleradas, y las formas enantiómeras y diastereómeras.Carboxylic acid derivatives of the formula I <EMI FILE = "99013467_1" ID = "1" MFI = JPEG> In which the substituents have the following meanings: R1 tetrazole or a group <EMI FILE = "99013467_2" ID = "2 "MFI = JPEG> Ra) an OR7 radical, where R7 means: hydrogen, the cation of an alkali metal, the cation of an alkaline earth metal or a physiologically tolerated ammonium ion; C3-C8-cycloalkyl, C1-C8-alkyl, CH2 - optionally substituted phenyl, a C3-C6-alkenyl group or a C3-C6-optionally substituted alkynyl group, or optionally substituted phenyl. a 5-membered heteroatom linked via a nitrogen atom group <EMI FILE = "99013467_3" ID = "3" MFI = JPEG> Where k can adopt values 0.1 and 2, p values 1, 2, 3 and 4 and R8 means C1-C4-alkyl, C3-C8-cycloalkyl, C3-C6-alkynyl or phenyl optionally substituted d) a radical <EMI FILE = "99013467_4" ID = "4" IMF = JPEG> Where R9 means: C1-C4-alkyl, C3-C6-alkynyl, C3-C8-cycloalkyl, C1-C4-halogenoalkyl, these radicals being able to carry a C1-C4-alkoxy, C1-C4-alkylthio radical and / or a phenyl radical; - 2 -e) a group <EMI FILE = "99013467_5" ID = "5" IMF = JPEG> R13 and R14 may be identical or different and have the following meanings: Hydrogen, C1-C8-alkyl, C3-C8-cycloalkyl, C3 -C8-alkenyl, C3-C8-alkynyl, benzyl, phenyl, optionally substituted OR R13 and R14 together form a closed C4-C7-alkylene chain forming a ring, optionally substituted, and which may contain a heteroatom, or R2 hydrogen, hydroxy, NH2, NH (C1-C4-alkyl), N (C1-C4-alkyl ilo) 2, halogen, C1-C4-C2-C4-alkenyl alkyl, C2-C4-alkynyl, C1-C4-hydroxyalkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy, C1-C4-halogenoalkoxy or C1-C4 -alkylthio, or CR2 is linked with CR10 in the manner indicated below, forming a 5 or 6 member ring. a X nitrogen or metino.Y nitrogen or metino.Z nitrogen or CR10, meaning R10 hydrogen, hydroxy, C1-C4 -haloalkyl or C1-C4-alkyl, or CR10 together with CR2 or CR3 forms an alkylene or alkenylene ring of 5 or 6 members, which may be eventually substituted, and where each time one or more methylene groups may be substituted by oxygen, sulfur, -NH or N (C1-C4-alkyl) 2 .R3 hydrogen, hydroxy, NH2, NH (C1 -C4-alkyl), N (C1-C4-alkyl) 2, halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-halogenoalkyl, C1-C4-alkoxy, C1- C4-halogenoalkoxy, C1-C4-hydroxyalkyl, C1-C4-alkylthio, or CR3 is linked with CR10, as indicated above, forming a five or six membered ring. R4 C1-C4-alkyl, C2-C4-alkenyl or C2-C4-alkynyl, optionally substituted R5 phenyl or naphthyl, optionally substituted, or phenyl or naphthyl, which is linked in the ortho position via a direct bond, a methylene, ethylene or ethenylene group, an oxygen atom or sulfur or an SO2, NH or N-alkyl group with optionally substituted R4 C3-C8-cycloalkyl; optionally substituted R6 C3-C8-cycloalkyl; phenyl or naphthyl, which in each case can carry one or more of the following radicals; halogen, R15, nitro, mercapto, carboxy, cyano, hydroxy, amino, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-alkenyloxy, C1-C4-halogenoalkyl, C3-C6- alkynyloxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxy, C1-C4-halogenoalkoxy, phenoxy, C1-C4-alkylthio, NH (C1-C4-alkyl), N (C1-C4-alkyl ) 2, dioxomethylene, dioxoethylene or phenyl, which may be mono or polysubstituted, e.g. mono to trisubstituted by halogen, nitro cyano, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy, C1-C4-halogenoalkoxy or C1-C4-alkylthio, being precise that when R6 is a phenyl radical without replace, then R2 and R3 cannot simultaneously mean OCH3; a five or six membered heteroaromatic, which contains one to three nitrogen atoms and / or a sulfur or oxygen atom, which can carry one to four halogen atoms and / or one of the following radicals: C1-C4-alkyl, C2-C4-alkenyl, C1-C4-halogenoalkyl, C1-C4-alkoxy, C1-C4-halogenoalkoxy, C1-C4-alkylthio, phenyl or phenoxy, whereby Phenyl radicals in turn carry one of five halogen atoms and / or one to three of the following radicals: C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy, C1-C4-halogenoalkoxy and / or C1 -C4-alkylthio; R15 C1-C4-alkyl, C1-C4-alkylthio, C1-C4-alkoxy, bearing one of the following radicals hydroxy, carboxy, amino, NH (C1-C4-alkyl), N (C1- C4-alkyl) 2, carboxy gives or CON (C1-C4-alkyl) 2, W sulfur or oxygen; Q a spacer, which in its length is equivalent to a chain of 2 to 4 carbon atoms, as well as its physiologically tolerated salts, and enantiomeric and diastereomeric forms .

CO99013467A 1998-03-04 1999-03-04 NEW ASYMETRICALLY SUBSTITUTED CARBOXYLIC ACID DERIVATIVES, THEIR OBTAINING AND USE AS ANTAGONISTS OF ET [sub A] / ET [sub B] MIXED RECEIVERS CO5080805A1 (en)

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