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AR073010A1 - Compuesto amida con actividad agonista del gpr52 - Google Patents

Compuesto amida con actividad agonista del gpr52

Info

Publication number
AR073010A1
AR073010A1 ARP090103088A ARP090103088A AR073010A1 AR 073010 A1 AR073010 A1 AR 073010A1 AR P090103088 A ARP090103088 A AR P090103088A AR P090103088 A ARP090103088 A AR P090103088A AR 073010 A1 AR073010 A1 AR 073010A1
Authority
AR
Argentina
Prior art keywords
phenyl
substituents
dihydro
ring
group
Prior art date
Application number
ARP090103088A
Other languages
English (en)
Inventor
Yuhei Miyanohana
Masaki Setoh
Mitsunori Kouno
Masakuni Kori
Original Assignee
Takeda Pharmaceutical
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 Takeda Pharmaceutical filed Critical Takeda Pharmaceutical
Publication of AR073010A1 publication Critical patent/AR073010A1/es

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    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
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    • C07D277/62—Benzothiazoles
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    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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    • 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
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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    • 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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    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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  • Organic Chemistry (AREA)
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  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Indole Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

El compuesto puede ser provisto como agente terapéutico o de prevencion para la esquizofrenia o similar. Método y usos. Reivindicacion 1: Un compuesto caracterizado por la formula (1) donde A representa -CONRa- o -NRaCO-; Ra representa un átomo de hidrogeno o un sustituyente; B representa un átomo de hidrogeno o un sustituyente; o en forma alternativa, cuando A es -CONRa-, Ra y B pueden formar junto con un átomo de nitrogeno adyacente un grupo heterocíclico que contiene nitrogeno el cual puede tener uno o más sustituyentes; o además en forma alternativa, cuando A es -CONRa-, B puede unirse al átomo de carbono adyacente al átomo de carbono al cual -A-B está unido para formar un anillo de cinco o seis miembros el cual puede tener uno o más sustituyentes; el anillo Cy1 representa un anillo aromático de seis miembros el cual puede tener uno o más sustituyentes además de un grupo representado por -A-B; el anillo Cy2 representa un anillo de seis miembros el cual puede tener uno o más sustituyentes seleccionados de un átomo de halogeno, un grupo ciano, un grupo hidroxi, un grupo hidrocarburo-oxi el cual puede tener uno o más sustituyentes, un grupo hidrocarburo en cadena el cual puede tener uno o más sustituyentes (salvo un grupo metilo sustituido con un grupo heterocíclico de cinco miembros), un grupo heterocíclico el cual puede tener uno o más sustituyentes, un grupo amino el cual puede tener uno o más sustituyentes, un grupo acilo, y un grupo carboxi el cual puede estar esterificado; anillo Cy3 representa un anillo de cinco o seis miembros el cual puede tener uno o más sustituyentes; X representa un alquileno C1-2 el cual puede estar sustituido con hidroxi, -Y-, Y-CH2-, o -CH2-Y-; Y representa -O-, -NRb-, o -S(O)m-; Rb representa un átomo de hidrogeno o un sustituyente; m representa un entero de 0 a 2; y el anillo Cy4 representa un anillo aromático de seis miembros el cual puede tener uno o más sustituyentes (salvo un grupo sulfamoilo el cual puede tener uno o más sustituyentes); con la condicion que un compuesto representado por la formula (2) donde R1p representa alquilo o cicloalquilalquilo; R2p y R3p representan cada uno independientemente un alquilo o un cicloalquilo o representan junto con un átomo de carbono adyacente, cualquiera de los anillos de carbono de tres a seis miembros saturados o anillos heterocíclicos (donde alquilo, cicloalquilo, un anillo de carbono, o un anillo heterocíclico es insaturado o saturado); y R4p representa arilo el cual puede estar sustituido o heteroarilo el cual puede estar sustituido; un compuesto representado por la formula (3) donde Rq1 representa fenilo el cual puede tener uno o más sustituyentes; Rq2 representa hidrogeno, o un sustituyente, los otros símbolos son sinonimo con los descriptos anteriormente; un compuesto representado por la formula (4) donde Rr1 representa fenilo el cual puede tener uno o más sustituyentes; Rq2 representa hidrogeno, o un sustituyente, los otros símbolos son sinonimo con los descriptos anteriormente; 7-[4-(acetilamino)fenil]-2-(bencilsulfanil)-5-metil-N-fenil-3,7-dihidro[1,2,4]triazolo[1,5-a]pirimidin-6-carboxamida, 7-[4-(acetilamino)fenil]-2-[(4-clorobencil)sulfanil]-N-(2,4-dimetilfenil)-5-metil-3,7-dihidro[1,2,4]triazolo[1,5-a]pirimidin-6-carboxamida, 7-[4-(acetilamino)fenil]-2-(bencilsulfanil)-N-(2-metoxifenil)-5-metil-3,7-dihidro[1,2,4]triazolo[1,5-a]pirimidin-6-carboxamida, 7-[4-(acetilamino)fenil]-2-[(2,4-dimetilbencil) sulfanil]-N-(4-metoxifenil)-5-metil-3,7-dihidro[1,2,4]triazolo[1,5-a]pirimidin-6-carboxamida, 7-[4-(acetilamino)fenil]-2-(bencilsulfanil)-N-(2,4-dimetilfenil)-5-metil-3,7-dihidro[1,2,4]triazolo[1,5-a]pirimidin-6-carboxamida, N-(3-(2-((4-cloro-2-metoxi-6-metilfenil)amino)-1-metil-1H-benzoimidazol-7-il)fenil)acetamida), [4-[2-metil-1-(fenilsulfonil)-1H-pirrolo[2,3-b]piridin-4-il]fenil]carbamato de metil ter-butilo, (4-[3-[(4-metoxibencil)amino]imidazo[1,5-a]piridin-5-il]fenil)carbamato de ter-butilo, 1-[4-(dietilcarbamoil)fenil]-6-metoxi-7-fenoxi-3,4-dihidroisoquinoIin-2(1H)-carboxilato de ter-butilo, 1-[4-(dietilcarbamoil)fenil]-7-(4-fluorofenoxi)-6-metoxi-3,4-dihidroisoquinolin-2(1H)-carboxilato de ter-butilo, 1-[4-(dietilcarbamoil)fenil]-6-metoxi-7-(4-metoxi fenoxi)-3,4-dihidroisoquinolin-2(1H)-carboxilato de ter-butilo, 1-[4-(dietilcarbamoil)fenil]-6-metoxi-7-(piridin-3-iloxi)-3,4-dihidroisoquinolin-2(1H)-carboxilato de ter-butilo, 1-[4-(1-bencil-1H-pirazolo[3,4-c]piridin-4-il)fenil]-3-[3-trifluorometil)fenil]urea, 1-[4-[1-(4-metoxibencil)-1H-pirazolo[3,4-c]piridin-4-il]fenil]-3-[3-(trifluorometil)fenil]urea, 3-cloro-2-[6-[(2-cloro-4-fluorofenil)sulfanil]-2-oxo-3,4-dihidropirido[3,2-d]pirimidin-1(2H)-il]benzamida, 3,5-dicloro-4-[6-[(2,4-difluorofenil)sulfanil]-2-oxo-3,4-dihidropirido[3,2-d]pirimidin-1(2H)-il]benzamida, 3,5-dicloro-4-[6-[(2,4-difluorofenil)sulfanil]-2-oxo-3,4-dihidropirido[3,2-d]pirimidin-1(2H)-il]-N-[2-(dimetilamino)etil]benzamida, 2-cloro-N-(3-cloro-4-[2-[(4-fluorofenil)sulfanil]-6-oxo-7,8-dihidro-6H-pirimido[1,6-b]piridazin-5-il] fenil)acetamida, N-(3-cloro-4-[2-[(4-fluorofenil)sulfanil]-6-oxo-7,8-dihidro-6H-pirimido[1,6-b]piridazin-5-il]fenil)acetamida, N-(3-cloro-4-[2-[(4-fluorofenil)sulfanil]-6-oxo-7,8-dihidro-6H-pirimido[1,6-b]piridazin-5-il]fenil)-2-morfolin-4-ilacetamida, N-(4-[2-[(3,4,5-trimetoxifenil)amino]-1,3-benzoxazol-7-il]fenil)acetamida, N-(3-[2-[(3,4,5-trimetoxifenil)amino]-1,3-benzoxazol-7-il]fenil)acetamida, N-(2-amino-4-[2-[(3,4,5-trimetoxifenil)amino]-1,3-benzoxazol-7-il]fenil)formamida, 7-[4-(acetilamino)fenil]-2-[(2,4-dimetilbencil)sulfanil]-5-metil-N-fenil-3,7-dihidro[1,2,4]triazolo[1,5-a]pirimidin-6-carboxamida, 5-[(3S)-3-(dibencilamino)-3,4-dihidro-2H-cromen-5-il]-2-metoxi-N,N-dimetilpiridin-3-carboxamida, 5-[(3S)-3-(dibencilamino)-3,4-dihidro-2H-cromen-5-il]-2-metoxi-N-metilpiridin-3-carboxamida, 5-[(3S)-3-(dibencilamino)-3,4-dihidro-2H-cromen-5-il]-2-metoxi-N-metilpiridin-3-carboxamida, y N-(6-[1-[(4-metilfenil)sulfonil]-1H-pirrolo[2,3-b]piridin-4-il]piridin-2-il)acetamida, se excluyen; o una sal del mismo.
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