AR063302A1 - DERIVATIVES OF 4-BENZO [B] TIOFEN-4-IL-PIPERAZIN-1-IL WITH ANTAGONIST ACTION OF THE 5-HT2A SEROTONINE RECEIVER AND ADRENALINE ALFA1 RECEPTOR AND PARTIAL AGRONIST OF THE D2 RECEPTOR, A PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND UNDERSTANDS TO PRODUCE IT. - Google Patents

DERIVATIVES OF 4-BENZO [B] TIOFEN-4-IL-PIPERAZIN-1-IL WITH ANTAGONIST ACTION OF THE 5-HT2A SEROTONINE RECEIVER AND ADRENALINE ALFA1 RECEPTOR AND PARTIAL AGRONIST OF THE D2 RECEPTOR, A PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND UNDERSTANDS TO PRODUCE IT.

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Publication number
AR063302A1
AR063302A1 ARP070104563A ARP070104563A AR063302A1 AR 063302 A1 AR063302 A1 AR 063302A1 AR P070104563 A ARP070104563 A AR P070104563A AR P070104563 A ARP070104563 A AR P070104563A AR 063302 A1 AR063302 A1 AR 063302A1
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Argentina
Prior art keywords
group
halogen
lower alkyl
aryl
alkyl
Prior art date
Application number
ARP070104563A
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Spanish (es)
Inventor
Yamashita Hiroshi
Oshima Kunio
Shimizu Satoshi
Fukushima Tae
Kuroda Hideaki
Tanaka Tatsuyoshi
Taira Shinichi
Matsubara Jun
Sakurai Yohji
Takahashi Haruka
Kondo Kazumi
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Otsuka Pharma Co Ltd
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Application filed by Otsuka Pharma Co Ltd filed Critical Otsuka Pharma Co Ltd
Publication of AR063302A1 publication Critical patent/AR063302A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 to carbon atoms of the hetero ring
    • C07D333/66—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Una composicion farmacéutica que los comprende y un proceso para producirlos. Reivindicacion 1: Un compuesto heterocíclico o una de sus sales caracterizado por la formula general (1) [en donde Q representa un grupo representado por la siguiente formula R11-C(=Z)N(R12)A1- (en donde A1 representa un grupo alquileno inferior; Z representa O o Si; R11 representa (1-1) hidrogeno, (1-2) alquilo inferior, (1-3) arilo seleccionado del grupo que consiste en un grupo fenilo, naftilo y dihidroindenilo (en donde el grupo arilo puede estar seleccionado por al menos un grupo seleccionado del grupo que consiste en los siguientes sustituyentes (i) a (xxxiii): (i) alquilo inferior, (ii) alquenilo inferior, (iii) alquilo inferior sustituido con halogeno, (iv) alcoxi inferior, (v) alcoxi inferior sustituido con halogeno, (vi) nitro, (vii) ciano, (viii) halogeno, (ix) arilo, (x) ariloxi, (xi) alcoxicarbonilo inferior, (xii) hidroxi, (xiii) hidroxi protegido, (xiv) alcanoilo inferior, (xv) sulfamoilo, (xvi) alquiltio inferior, (xvii) alquilsulfonilo inferior, (xviii) hidroxisulfonilo, (xix) amino que puede tener grupos seleccionados del grupo que consiste en alquilo inferior, alcanoilo inferior, cicloalquilo C3-8, arilo y aroílo, (xx) morfolinilcarbonilalquenilo inferior, (xxi) morfolinilcarbonilalquilo inferior, (xxii) pirrolilo, (xxiii) pirazolilo, (xxiv) imidazolilo, (xxv) triazolilo, (xxvi) piridilo, (xxvii) pirrolidinilo que puede tener uno o varios grupos oxo, (xxviii) morfolinilo, (xxix) tiomorfolinilo, (xxx) alquinilo inferior, (xxxi) cicloalquilo C3-8, (xxxii) guanidino y (xxxiii) dihidropirazolilo que puede tener 1 o varios grupos seleccionados del grupo que consiste en un grupo oxo y un grupo alquilo inferior), (1-4) un grupo heterocíclico (en donde el grupo heterocíclico puede estar seleccionado por al menos un grupo seleccionado del grupo que consiste en los siguientes sustituyentes (i) a (xix): (i) alquilo inferior, (ii) alquilo inferior sustituido con halogeno, (iii) alcoxi inferior, (iv) alcoxi inferior sustituido con halogeno, (v) halogeno, (vi) arilo que puede tener, en el grupo arilo, un grupo seleccionado el grupo que consiste en halogeno y un alquilo inferior sustituido con halogeno, (vii) arilalquilo inferior que puede tener átomos de halogenos, (viii) alcanoilo inferior, (ix) aroílo, (x) aminoalcanoilo inferior que puede tener, en el grupo amino, un grupo alcanoilo inferior, (xi) alquiltio inferior, (xii) pirrolilo, (xiii) oxo, (xiv) tioxo, (xv) carbamoilo, (xvi) hidroxi, (xvii) piranilo, (xviii) tienilo y (xix) furilo, (1-15) un grupo aminoalquilo inferior que puede tener, en el grupo amino y/o el grupo alquilo inferior, un grupo o grupos seleccionados del grupo que consiste en un grupo alquilo inferior, alcanoilo inferior, hidroxialquilo inferior, alcoxicarbonilo inferior, carbamoilalquilo inferior, indolilcarbonilo, arilo (el grupo arilo puede tener un grupo o grupos seleccionados del grupo que consiste en halogeno y un grupo alcoxi inferior) y arilalcoxicarbonilo inferior, (1-6) alcoxi inferior-alquilo inferior, (1-7) aroilalquilo inferior, (1-8) arilalquilo inferior que puede tener, en el grupo arilo, un grupo o grupos seleccionados del grupo que consiste en un grupo alquilo inferior, alcoxi inferior, hidroxi, halogeno y un grupo nitro, (1-9) ariloxialquilo inferior que puede tener, en el grupo arilo, un grupo seleccionado del grupo que consiste en un grupo alquilo inferior, alcoxi inferior, halogeno y un grupo ciano, (1-10) adamantilalquilo inferior, (1-11) arilalquenilo inferior que puede tener, en el grupo arilo, un grupo seleccionado el grupo que consiste en un grupo alquilo inferior, alcoxi inferior, alquilo inferior sustituido con halogeno, alcoxi inferior sustituido con halogeno, amino que puede tener un grupo o grupos alquilo inferior, halogeno y un grupo nitro, (1-12) cicloalquilo C3-8 que puede tener un grupo o grupos seleccionados del grupo que consiste en: amino que puede tener un grupo o grupos alquilo inferior, aminoalquilo inferior que puede tener un grupo o grupos alquilo inferior, y arilo que puede tener un grupo seleccionado del grupo que consiste en halogeno y alquilo inferior, (1-13) cicloalquil C3-8-alquilo inferior, (1-14) ariltioalquilo inferior, (1-15) alquilo inferior sustituido con un grupo heterocíclico seleccionado del grupo que consiste en piperidilo, tetrahidropiranilo, piridilo, tienilo, imidazolilo, tetrazolilo, bencimidazolilo, isoindolilo, tiazolidinilo y un grupo indolilo (en donde el grupo heterocíclico puede tener un grupo o grupos seleccionados del grupo que consiste en un grupo alquilo inferior, alcoxi inferior, halogeno, oxo y tioxo), (1-16) arilalquenilo inferior (que puede tener, en el grupo alquenilo inferior, arilo), (1-17) alquenilo inferior sustituido con un grupo heterocíclico seleccionado del grupo que consiste en benzodioxolilo, piridilo, furilo y un grupo imidazolilo, (1-18) un grupo benzodioxoliloxialquilo inferior, (1-19) piridiltioalquilo inferior, o (1-20) amino que puede tener un grupo o grupos alquilo inferior; y R12 representa (2-1) hidrogeno, (2-2) alquilo inferior, (2-3) alquilo inferior sustituido con halogeno, (2-4) alquenilo inferior, (2-5) alquinilo inferior, (2-6) alcanoilo inferior, (2-7) hidroxialquilo inferior, (2-8) alcoxi inferior-alquilo inferior, (2-9) cicloalquilo C3-8, (2-10) cicloalquil C3-8-alquilo inferior, (2-11) arilo, (2-12) arilalquilo inferior que puede tener, en el grupo arilo, un grupo seleccionado del grupo que consiste en un grupo amino que puede tener un grupo o grupos alquilo inferior y un grupo ariloxi, (2-13) tetrahidrofurilo, (2-14) alquilo inferior sustituido con un grupo heterocíclico seleccionado del grupo que consiste en un grupo furilo y un grupo piridilo, (2-15) tetrahidropiranilo, o (2-16) alcanoiloxi inferior-alquilo inferior), o un grupo representado por la siguiente formula general R21-A2- ( en donde -A2- representa alquileno inferior, alquenileno inferior o un grupo -A21-O-A22-, en donde A21 y A22 son iguales o diferentes y cada uno representa alquileno C1-5, (con la condicion de que un numero total de átomos de C que constituyen el grupo alquileno de A21 y el grupo alquileno de A22 no exceda 6); y R21 representa un grupo heterocíclico que contiene N, en donde el grupo heterocíclico que contiene N representado por R21 puede estar seleccionado por al menos un grupo seleccionado del grupo que consiste en los siguientes puntos (1) a (13): (1) alquilo inferior sustituido con halogeno o no sustituido, (2) alquenilo inferior, (3) alcoxi inferior, (4) hidroxi, (5) hidroxi protegido, (6) arilo, (7) alcanoilo inferior, (8) carboxi, (9) alcoxicarbonilo inferior, (10) carbamoilo que puede tener un grupo o grupos alquilo inferior, (11) arilalquilo inferior (que puede tener, en el grupo arilo, un grupo o grupos alcoxi inferior) (12) oxo y (13) tioxo)].A pharmaceutical composition that understands them and a process to produce them. Claim 1: A heterocyclic compound or a salt thereof characterized by the general formula (1) [wherein Q represents a group represented by the following formula R11-C (= Z) N (R12) A1- (wherein A1 represents a lower alkylene group; Z represents O or Si; R11 represents (1-1) hydrogen, (1-2) lower alkyl, (1-3) aryl selected from the group consisting of a phenyl, naphthyl and dihydroindenyl group (wherein the aryl group may be selected by at least one group selected from the group consisting of the following substituents (i) to (xxxiii): (i) lower alkyl, (ii) lower alkenyl, (iii) lower alkyl substituted with halogen, (iv ) lower alkoxy, (v) halogen substituted lower alkoxy, (vi) nitro, (vii) cyano, (viii) halogen, (ix) aryl, (x) aryloxy, (xi) lower alkoxycarbonyl, (xii) hydroxy, ( xiii) protected hydroxy, (xiv) lower alkanoyl, (xv) sulfamoyl, (xvi) lower alkylthio, (xvii) lower alkylsulfonyl, (xviii) hydroxysulfoni lo, (xix) amino which may have groups selected from the group consisting of lower alkyl, lower alkanoyl, C3-8 cycloalkyl, aryl and aroyl, (xx) lower morpholinylcarbonylalkyl, (xxi) morpholinylcarbonylalkyl, (xxii) pyrrolyl, (xxiii ) pyrazolyl, (xxiv) imidazolyl, (xxv) triazolyl, (xxvi) pyridyl, (xxvii) pyrrolidinyl which may have one or more oxo groups, (xxviii) morpholinyl, (xxix) thiomorpholinyl, (xxx) lower alkynyl, (xxxi) C3-8 cycloalkyl, (xxxii) guanidino and (xxxiii) dihydropyrazzolyl which may have 1 or several groups selected from the group consisting of an oxo group and a lower alkyl group), (1-4) a heterocyclic group (wherein the group heterocyclic may be selected by at least one group selected from the group consisting of the following substituents (i) to (xix): (i) lower alkyl, (ii) lower alkyl substituted with halogen, (iii) lower alkoxy, (iv) lower alkoxy substituted with halogen, (v) halogen, ( vi) aryl which may have, in the aryl group, a group selected from the group consisting of halogen and a lower alkyl substituted with halogen, (vii) lower arylalkyl which may have halogen atoms, (viii) lower alkanoyl, (ix) aroyl, (x) lower aminoalkanoyl which may have, in the amino group, a lower alkanoyl group, (xi) lower alkylthio, (xii) pyrrolyl, (xiii) oxo, (xiv) thioxo, (xv) carbamoyl, (xvi) hydroxy, (xvii) pyranyl, (xviii) thienyl and (xix) furyl, (1-15) a lower aminoalkyl group which may have, in the amino group and / or the lower alkyl group, a group or groups selected from the group that it consists of a lower alkyl, lower alkanoyl, lower hydroxyalkyl, lower alkoxycarbonyl, lower carbamoylalkyl, indolylcarbonyl, aryl group (the aryl group may have a group or groups selected from the group consisting of halogen and a lower alkoxy group) and lower arylalkoxycarbonyl, ( 1-6) lower alkoxy-lower alkyl , (1-7) lower aroylalkyl, (1-8) lower arylalkyl which may have, in the aryl group, a group or groups selected from the group consisting of a lower alkyl, lower alkoxy, hydroxy, halogen and a nitro group , (1-9) lower aryloxyalkyl which may have, in the aryl group, a group selected from the group consisting of a lower alkyl, lower alkoxy, halogen and a cyano group, (1-10) lower adamantyl alkyl, (1- 11) lower arylalkenyl which may have, in the aryl group, a group selected from the group consisting of a lower alkyl group, lower alkoxy, lower alkyl substituted by halogen, lower alkoxy substituted by halogen, amino which may have a group or alkyl groups lower, halogen and a nitro group, (1-12) C3-8 cycloalkyl which may have a group or groups selected from the group consisting of: amino that may have a lower alkyl group or groups, lower aminoalkyl that may have a group or alkyl groups in ferior, and aryl which may have a group selected from the group consisting of halogen and lower alkyl, (1-13) C3-8 cycloalkyl-lower alkyl, (1-14) lower arylthioalkyl, (1-15) lower alkyl substituted with a heterocyclic group selected from the group consisting of piperidyl, tetrahydropyranyl, pyridyl, thienyl, imidazolyl, tetrazolyl, benzimidazolyl, isoindolyl, thiazolidinyl and an indolyl group (wherein the heterocyclic group may have a group or groups selected from the group consisting of a group lower alkyl, lower alkoxy, halogen, oxo and thioxo), (1-16) lower arylalkenyl (which may have, in the lower alkenyl group, aryl), (1-17) lower alkenyl substituted with a heterocyclic group selected from the group that it consists of benzodioxolyl, pyridyl, furyl and an imidazolyl group, (1-18) a lower benzodioxoliloxyalkyl group, (1-19) lower pyridylthioalkyl, or (1-20) amino which may have a lower alkyl group or groups; and R12 represents (2-1) hydrogen, (2-2) lower alkyl, (2-3) lower alkyl substituted with halogen, (2-4) lower alkenyl, (2-5) lower alkynyl, (2-6) lower alkanoyl, (2-7) lower hydroxyalkyl, (2-8) lower alkoxy-lower alkyl, (2-9) C3-8 cycloalkyl, (2-10) C3-8 cycloalkyl-lower alkyl, (2-11) aryl, (2-12) lower arylalkyl which may have, in the aryl group, a group selected from the group consisting of an amino group that may have a lower alkyl group or groups and an aryloxy group, (2-13) tetrahydrofuryl, (2-14) lower alkyl substituted with a heterocyclic group selected from the group consisting of a furyl group and a pyridyl group, (2-15) tetrahydropyranyl, or (2-16) lower alkanoyloxy-lower alkyl), or a group represented by the following general formula R21-A2- (where -A2- represents lower alkylene, lower alkenylene or a group -A21-O-A22-, where A21 and A22 are the same or different and each represents alq C1-5 uylene, (with the proviso that a total number of C atoms constituting the alkylene group of A21 and the alkylene group of A22 does not exceed 6); and R21 represents an N-containing heterocyclic group, wherein the N-containing heterocyclic group represented by R21 may be selected by at least one group selected from the group consisting of the following points (1) to (13): (1) alkyl lower halogen substituted or unsubstituted, (2) lower alkenyl, (3) lower alkoxy, (4) hydroxy, (5) protected hydroxy, (6) aryl, (7) lower alkanoyl, (8) carboxy, (9) lower alkoxycarbonyl, (10) carbamoyl which may have a lower alkyl group or groups, (11) lower arylalkyl (which may have, in the aryl group, a lower alkoxy group or groups) (12) oxo and (13) thioxo)] .

ARP070104563A 2006-10-13 2007-10-12 DERIVATIVES OF 4-BENZO [B] TIOFEN-4-IL-PIPERAZIN-1-IL WITH ANTAGONIST ACTION OF THE 5-HT2A SEROTONINE RECEIVER AND ADRENALINE ALFA1 RECEPTOR AND PARTIAL AGRONIST OF THE D2 RECEPTOR, A PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND UNDERSTANDS TO PRODUCE IT. AR063302A1 (en)

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JP2006280002 2006-10-13
JP2006280030 2006-10-13

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AR063302A1 true AR063302A1 (en) 2009-01-21

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AR (1) AR063302A1 (en)
TW (1) TW200831498A (en)
WO (1) WO2008047883A1 (en)

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