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AR059687A1 - Derivados de pirazol inhibidores de la enzima mao-b,utiles para mejorar la funcion cognitiva, composiciones farmaceuticas que los contienen,y metodo de preparacion. - Google Patents

Derivados de pirazol inhibidores de la enzima mao-b,utiles para mejorar la funcion cognitiva, composiciones farmaceuticas que los contienen,y metodo de preparacion.

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Publication number
AR059687A1
AR059687A1 ARP070100832A ARP070100832A AR059687A1 AR 059687 A1 AR059687 A1 AR 059687A1 AR P070100832 A ARP070100832 A AR P070100832A AR P070100832 A ARP070100832 A AR P070100832A AR 059687 A1 AR059687 A1 AR 059687A1
Authority
AR
Argentina
Prior art keywords
alkyl
aryl
het
halo
substituted
Prior art date
Application number
ARP070100832A
Other languages
English (en)
Inventor
Andrew Mcriner
Roderick E M Scott
Rusiko Bourtchouladze
Xianbo Zhou
Terence P Keenan
Alan P Kaplan
Original Assignee
Helicon Therapeutics Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Helicon Therapeutics Inc filed Critical Helicon Therapeutics Inc
Publication of AR059687A1 publication Critical patent/AR059687A1/es

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    • 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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4152—1,2-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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    • A61P25/00—Drugs for disorders of the nervous system
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    • 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
    • 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
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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    • A61P25/22—Anxiolytics
    • 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
    • A61P25/24—Antidepressants
    • 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
    • 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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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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    • 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
    • C07D401/10—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 carbon chain containing aromatic rings
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    • C07—ORGANIC CHEMISTRY
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    • C07D401/14—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 three or more hetero rings
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    • C07D417/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
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    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08—Bridged systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Veterinary Medicine (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Reivindicacion 64: Un compuesto caracterizado porque responde a la formula (1) en donde R1 es alquilo C1-6, haloalquilo C1-6, o arilo, no sustituido o sustituido con uno o más Re; uno de R2 y R3 está ausente y el otro es hidrogeno, alquilo C1-6, halo(C1-6)alquilo, hidroxi(C1-6)alquilo, cicloalquilo C3-8, amino(C2-6)alquilo, o arilo, cada uno no sustituido o sustituido con uno o más grupos seleccionados entre alquilo, halo, haloalquilo o nitro, Het, cicloalquil C3-8-alquilo C1-6, aril(C1- 6)alquilo, o Het(C1-6)alquilo; B es arilo o heteroarilo; X es -C(O), -C(=S), -C(R4)2, o -S(O)z; cada z es en forma independiente 0, 1, o 2; Y es R4, -N(R4)2,-OR4, -SR4, o -C(R4)3, cada R4 se selecciona en forma independiente entre el grupo formado por hidrogeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6, alcanoilo C1-6, alcoxicarbonilo C1-6, cicloalquilo C3-8, cicloalquil C3-8-alquilo C1-6, alcoxi C1-6-alquilo C2-6, hidroxi(C2-6)alquilo, ciano(C1-6)alquilo, alquiltio C1-6- alquilo C2-6, arilo, aril (C1-6)alquilo, ariloxi (C2-6)alquilo, halo(C2-6)alquilo, alcoxicarbonil C1-6-alquilo C1-6, NRaRb, Het, o Het(C1-6)alquilo, en donde cada alquilo, arilo, o Het es no sustituido o sustituido con uno o más Rd; o dos grupos R4 se toman junto con el átomo al cual están unidos para formar arilo, Het, o un sistema de anillos saturado o insaturado monocíclico de 3-8 miembros o bicíclico de 8-12 miembros que comprende átomos de carbono y que opcionalmente comprende uno o más heteroátomos adicionales seleccionados entre O, S(O)z y NRc, en donde cada sistema de anillos está opcionalmente sustituido con uno o más Rd; cada Ra y Rb es en forma independiente hidrogeno o alquilo C1-6; cada Rc es en forma independiente hidrogeno, arilo, S(O)2, alcanoilo C1-6, hidroxi(C1-6)alquilo, alcoxi(C1-6)alquilo, Het, alcoxicarbonilo C1-6 o alquilo C1-6, no sustituido o sustituido con uno o más sustituyentes Re; cada Rd es en forma independiente halo, hidroxi, ciano, nitro, azido, amino, alquilamino C1-6, amino(C1-6)alquilo, amido, alquilamido C1-6, arilo amido, ácido carboxílico, alquilo C1-6, hidroxi(C1-6)alquilo, halo(C1-6)alquilo, alcoxi C1-6, halo(C1-6)alcoxi, alcanoilo C1-6, alcoxicarbonilo C1-6, alcanoiloxi C1- 6, Het, arilo, Het(C1-6)alquilo, o aril(C1-6)alquilo, alquilarilo C1-6,.sulfonilo, sulfonamido, urea, carbamato, no sustituido o sustituido con uno o más sustituyentes Re, o dos Rd se unen con el átomo al cual están unidos para formar una cetona o anillo espirocíclico carbocíclico o heterocíclico, o dos Rd se unen con los átomos a los cuales están unidos para formar un anillo carbocíclico bicíclico o heterocíclico, en donde cada anillo espirocíclico o bicíclico es no sustituido o sustituido con uno o más halo, hidroxi, ciano, nitro, azido, alquilo C1-6, hidroxi(C1-6)alquilo, halo(C1-6)alquilo, alcoxi C1-6, halo(C1-6)alcoxi, alcanoilo C1-6, alcoxicarbonilo C1-6, carboxi, alcanoiloxi C1-6, NRfRg, RfRgNC(=O)-, fenilo, o fenil(C1- 6)alquilo, sulfonilo, sulfonamido, urea, carbamato, en donde Rf y Rg junto con el nitrogeno al cual están unidos forman un anillo piperidino, pirrolidino, morfolino, o tiomorfolino, no sustituido o sustituido con uno o más sustituyentes Re; cada Re se selecciona en forma independiente entre halo, hidroxi, ciano, nitro, azido, alquilo C1-6, Het, arilo, alquilHet C1-6, alquilarilo C1-6, alquilHet C1-6-alquilo C1-6, alquilaril C1-6-alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, alcanoilo C1-6, alcoxicarbonilo C1-6, carboxi, y alcanoiloxi C1-6; R5 es H, alquilo C1-6, alquenilo C1-6, alquinilo C1-6, aril(C1-6)alquilo; y cada R6 es H, alquilo C1-6, amino, amido, ceto, o aril(C1-6)alquilo; con la salvedad de que cuando Bis tiofene, R1 es trifluorometilo, R2 es metilo, R3 y R6 están ausentes, R5 es H, X es C(=O) y Y es N(R4)2, ambos R4 no son metilo.
ARP070100832A 2006-02-28 2007-02-28 Derivados de pirazol inhibidores de la enzima mao-b,utiles para mejorar la funcion cognitiva, composiciones farmaceuticas que los contienen,y metodo de preparacion. AR059687A1 (es)

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US89045507P 2007-02-16 2007-02-16

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AR059687A1 true AR059687A1 (es) 2008-04-23

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US (3) US7919626B2 (es)
EP (2) EP1989185B8 (es)
JP (1) JP5503874B2 (es)
CN (1) CN101484424B (es)
AR (1) AR059687A1 (es)
AU (1) AU2007221020B9 (es)
BR (1) BRPI0708353A8 (es)
CA (1) CA2644068C (es)
ES (1) ES2425578T3 (es)
IL (1) IL193678A (es)
NZ (2) NZ570847A (es)
SG (1) SG171617A1 (es)
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