ES2317103T3 - Derivados de c-ciclohexilmetilamina sustituidos. - Google Patents

Derivados de c-ciclohexilmetilamina sustituidos. Download PDF

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ES2317103T3
ES2317103T3 ES05011581T ES05011581T ES2317103T3 ES 2317103 T3 ES2317103 T3 ES 2317103T3 ES 05011581 T ES05011581 T ES 05011581T ES 05011581 T ES05011581 T ES 05011581T ES 2317103 T3 ES2317103 T3 ES 2317103T3
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substituted
phenyl
unsubstituted
cycloalkyl
alkyl
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Bernd Dr. Sundermann
Corinna Dr. Sundermann
Helmut Dr. Buschmann
Michael Dr. Finkam
Babett-Yvonne Dr. Kogel
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Gruenenthal GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/24—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/41—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/79—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/14—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/54—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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Abstract

Derivados de C-ciclohexilmetilamina sustituidos de fórmula general I ** ver fórmula** donde A se selecciona entre H o fenilo; R 1 se selecciona entre alquilo(C1-10) o cicloalquilo(C3-10), en cada caso saturado o insaturado, ramificado o no ramificado, sustituido de forma simple o múltiple o no sustituido, naftilo, fenilo con la condición de que R 1 no sea un anillo fenilo O- o S-sustituido en la posición 3, furilo, tiofenilo; fenilo, naftilo unido a través de un alquileno(C 1-3) o un etinilo, cicloalquilo(C 3-10) unido a través de un alquileno(C 1-3) o un etinilo; o tiofenilo, furilo unido a través de un alquileno(C1-3) o un etinilo, en cada caso sustituido de forma simple o múltiple o no sustituido, seleccionándose los sustituyentes, independientemente entre sí, de entre F, Cl, Br, I, OR 18 , SR 18 , SO 2R 18 , SO2OR 18 , CN, COOR 18 , NR 19 R 20 ; alquilo(C1-10) o cicloalquilo(C3-10), en cada caso no sustituido o sustituido de forma simple o múltiple, de forma igual o diferente, con F, Cl, Br, I, NH2, SH u OH, o sililo; R 18 se selecciona entre H, alquilo(C 1-10) o cicloalquilo(C 3-10), en cada caso saturado o insaturado, ramificado o no ramificado; R 19 y R 20 se seleccionan, independientemente entre sí, entre H, alquilo(C1-10) o cicloalquilo(C3-10), en cada caso saturado o insaturado, ramificado o no ramificado; o R 19 y R 20 forman conjuntamente CH2CH2OCH2CH2, CH2CH2NR 21 CH2CH2 o (CH2)3-6; donde R 21 se selecciona entre H, fenilo, alquilo(C1-10) saturado o insaturado, ramificado o no ramificado; R 2 y R 3 se seleccionan, independientemente entre sí, entre H, alquilo(C 1-10) o cicloalquilo(C 3-10), en cada caso saturado o insaturado, ramificado o no ramificado; o los grupos R 2 y R 3 significan conjuntamente CH2CH2OCH2CH2, CH2CH2NR 6 CH2CH2 o (CH2)3-6; R 6 se selecciona entre H, alquilo(C 1-10) o cicloalquilo(C 3-10), en cada caso saturado o insaturado, ramificado o no ramificado; X en la fórmula I según la fórmula parcial Ia de la fórmula I ** ver fórmula** significa , ** ver fórmula** donde B se selecciona entre OH, OR 7 , H, F, Cl o NR 8 R 9 , seleccionándose R 7 de entre alquilo(C1-10) o cicloalquilo(C3-10), en cada caso saturado o insaturado, ramificado o no ramificado, no sustituido o sustituido de forma simple o múltiple, de forma igual o diferente, con F, Cl, Br, I, NH 2, SH u OH; R 8 y R 9 se seleccionan, independientemente entre sí, entre H, alquilo(C1-10) o cicloalquilo(C3-10), en cada caso saturado o insaturado, ramificado o no ramificado, no sustituido o sustituido de forma simple o múltiple, de forma igual o diferente, con F, Cl, Br, I, NH 2, SH u OH; o los grupos R 8 y R 9 forman conjuntamente CH2CH2OCH2CH2, CH2CH2NR 10 CH2CH2 o (CH2)3-6; donde R 10 se selecciona entre H, alquilo(C 1-10-alquilo) o cicloalquilo(C 3-10), en cada caso saturado o insaturado, ramificado o no ramificado, no sustituido o sustituido de forma simple o múltiple, de forma igual o diferente, con F, Cl, Br, I, NH2, SH u OH; ** ver fórmula** se selecciona entre ** ver fórmula** seleccionándose R 4 entre COR 5 ; SO 2R 5 ; alquilo(C 1-10) o cicloalquilo(C 3-10), en cada caso saturado o insaturado, ramificado o no ramificado, sustituido de forma simple o múltiple o no sustituido; naftilo, fenilo, furilo o tiofenilo, en cada caso sustituido de forma simple o múltiple o no sustituido; o naftilo, fenilo, cicloalquilo(C3-10), furilo o tiofenilo unido a través de un alquileno(C1-3), en cada caso sustituido de forma simple o múltiple o no sustituido; R 5 se selecciona entre alquilo(C1-10) o cicloalquilo(C3-10), en cada caso saturado o insaturado, ramificado o no ramificado, sustituido de forma simple o múltiple o no sustituido; naftilo, fenilo, furilo, tiofenilo, en cada caso sustituido de forma simple o múltiple o no sustituido; o naftilo, fenilo, cicloalquilo(C 3-10), furilo o tiofenilo unido a través de un alquileno(C 1-3), en cada caso sustituido de forma simple o múltiple o no sustituido; V se selecciona entre OR 4 o NR 4 R 11 ; W se selecciona entre R 11 , OR 12 o NR 11 R 12 ; donde R 11 y R 12 se seleccionan, independientemente entre sí, entre H, alquilo(C7-10) o cicloalquilo(C3-10), en cada caso saturado o insaturado, ramificado o no ramificado, sustituido de forma simple o múltiple o no sustituido; naftilo, fenilo, furilo o tiofenilo, en cada caso sustituido de forma simple o múltiple o no sustituido; o naftilo, fenilo, cicloalquilo(C 3-10), furilo o tiofenilo unido a través de un alquileno(C 1-3), en cada caso sustituido de forma simple o múltiple o no sustituido; debiendo entenderse por el concepto "sustituido" en relación con alquilo y cicloalquilo para R 4 , R 5 , R 11 y R 12 , la sustitución con F, Cl, Br, I, NH 2, SH u OH, y debiendo entenderse por el concepto "sustituido" en relación con naftilo, fenilo, furilo y tiofenilo para R 4 , R 5 , R 11 y R 12 , la sustitución del naftilo, fenilo, furilo o tiofenilo por R 23 , OR 23 , un halógeno, un CF3, un CN, un NO 2, un NR 24 R 25 , un alquilo(C 1-6) (saturado), un alcoxi(C 1-6), un cicloalcoxi(C 3-8), un cicloalquilo(C 3-8) o un alquileno(C 2-6); donde el grupo R 23 representa H, un grupo alquilo(C1-10), un grupo naftilo, fenilo, furilo o tiofenilo, o un grupo naftilo, fenilo, furilo o tiofenilo unido a través de un grupo alquileno(C 1-3), no pudiendo estos grupos naftilo, fenilo, furilo o tiofenilo estar sustituidos a su vez con grupos arilo o heteroarilo; los grupos R 24 y R 25 , iguales o diferentes, representan H, un grupo (C1-10), un grupo naftilo, fenilo, furilo o tiofenilo, o un grupo naftilo, fenilo, furilo o tiofenilo unido a través de un grupo alquileno(C1-3), no pudiendo estos grupos naftilo, fenilo, furilo o tiofenilo estar sustituidos a su vez con grupos arilo o heteroarilo; o los grupos R 24 y R 25 significan conjuntamente CH2CH2OCH2CH2, CH2CH2NR 26 CH2CH2 o (CH2)3-6; y el grupo R 26 representa H, un grupo alquilo(C1-10), naftilo, fenilo, furilo o tiofenilo, o un grupo naftilo, fenilo, furilo o tiofenilo unido a través de un grupo alquileno(C 1-3), no pudiendo estos grupos naftilo, fenilo, furilo o tiofenilo estar sustituidos a su vez con grupos arilo o heteroarilo; en caso dado en forma de sus racematos, de sus estereoisómeros puros, o en forma de mezcla de estereoisómeros en cualquier proporción de mezcla, en la forma representada o en forma de sus ácidos o bases o en forma de sus sales, o en forma de sus solvatos, a excepción de aquellos compuestos en los que R 2 , R 3 se seleccionan, independientemente entre sí, entre o H, alquilo(C1-C10) ramificado o no ramificado, sustituido de forma simple o múltiple o no sustituido, saturado o insaturado; cicloalquilo(C3-C7) saturado o insaturado, sustituido de forma simple o múltiple o no sustituido, o un heterociclo correspondiente en el que un átomo de C del anillo está sustituido por N, S u O, en cada caso sustituido de forma simple o múltiple o no sustituido; R 2 y R 3 forman conjuntamente un anillo y significan CH 2CH 2OCH 2CH 2, CH 2CH 2NR 6 CH 2CH 2 o (CH 2) 3-6; X en la fórmula I según la fórmula parcial Ia de la fórmula I ** ver fórmula** tiene el siguiente significado ** ver fórmula** es decir, X significa , ** ver fórmula** A es hidrógeno; R 1 es un anillo fenilo sustituido de forma simple o doble; B se selecciona entre H, F, Cl, OH u OR 7 , seleccionándose R 7 entre alquilo(C1-C10) ramificado o no ramificado, sustituido de forma simple o múltiple o no sustituido, saturado o insaturado; cicloalquilo(C 3-C 7) saturado o insaturado, sustituido de forma simple o múltiple o no sustituido, o un heterociclo correspondiente en el que un átomo de C del anillo está sustituido por N, S u O, en cada caso sustituido de forma simple o múltiple o no sustituido; y al mismo tiempo el grupo ** ver fórmula** significa** ver fórmula** , donde V se selecciona entre OR 4 , R 4 se selecciona entre COR 5 y R 5 se selecciona entre alquilo(C1-6) sustituido de forma simple o múltiple o no sustituido.
ES05011581T 2000-09-29 2001-09-28 Derivados de c-ciclohexilmetilamina sustituidos. Expired - Lifetime ES2317103T3 (es)

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DE10049481A DE10049481A1 (de) 2000-09-29 2000-09-29 Substituierte C-Cyclohexylmethylamin-Derivate

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DE10153347A1 (de) * 2001-10-29 2003-05-08 Gruenenthal Gmbh Substituierte 1H-Chinolin-2-on-Verbindungen
DE10153346A1 (de) 2001-10-29 2004-04-22 Grünenthal GmbH Substituierte Indole
DE10161644A1 (de) * 2001-12-14 2003-06-26 Gruenenthal Gmbh N,N'-disubstituierte Piperazin-Verbindungen
DE10261091A1 (de) * 2002-12-20 2004-07-01 Grünenthal GmbH Gesättigte und ungesättigte Heteroarylcycloalkylmethyl-Amine
DE102004039382A1 (de) * 2004-08-13 2006-02-23 Grünenthal GmbH Spirocyclische Cyclohexan-Derivate
DE102005061428A1 (de) * 2005-12-22 2007-08-16 Grünenthal GmbH Substituierte Cyclohexylmethyl-Derivate
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