AR043860A1 - Compuesto de anillo heteroaromatico de 5 miembros y su uso farmaceutico - Google Patents

Compuesto de anillo heteroaromatico de 5 miembros y su uso farmaceutico

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Publication number
AR043860A1
AR043860A1 ARP040101228A ARP040101228A AR043860A1 AR 043860 A1 AR043860 A1 AR 043860A1 AR P040101228 A ARP040101228 A AR P040101228A AR P040101228 A ARP040101228 A AR P040101228A AR 043860 A1 AR043860 A1 AR 043860A1
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Argentina
Prior art keywords
group
optionally substituted
atom
alkyl
optionally
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Application number
ARP040101228A
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English (en)
Inventor
T Ikemoto
M Tanaka
T Yuno
J Sakamoto
H Nakanishi
Y Nakagawa
T Ohta
S Sakata
H Morinaga
Original Assignee
Japan Tobacco Inc
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Publication date
Application filed by Japan Tobacco Inc filed Critical Japan Tobacco Inc
Publication of AR043860A1 publication Critical patent/AR043860A1/es

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    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
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    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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    • 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
    • A61K31/42—Oxazoles
    • A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
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    • A61K31/42—Oxazoles
    • A61K31/423—Oxazoles condensed with carbocyclic rings
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    • 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
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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    • 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
    • A61K31/425—Thiazoles
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    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
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    • 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
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
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    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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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    • 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
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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Emergency Medicine (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Child & Adolescent Psychology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Endocrinology (AREA)
  • Cardiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Indole Compounds (AREA)

Abstract

l compuesto de la presente tiene una actividad inhibidora de la proteintirosinafosfatasa 1 B superior y es útil como agente terapéutico para diabetes, complicaciones diabéticas hiperlipidemia, obesidad y similares. Reivindicación 1:Un compuesto de anillo heteroaromático de 5 miembros representado por la fórmula (1) donde V es =N- o =CH-; W es -S- u -O-; m es 0, 1 o 2; R1 y R2 son cada uno, de modo independiente, un átomo de H o un grupo alquilo C1-4; X es -N(R4)-, -N(R5)-CO-O-, -SO2-N(R5)-, -N(R5)-SO2-, -N(R6)-, -SO2-N(R5)-, -CO-N(R7)-, -N(R8)-CO-, -N(R 9 )-CO-N(R5)-, -N(R10)-(CH2)k-N(R5)-, -N(R10)-(CH2)k-N(R5)-CO-, -C(R10)=N-N(R7)-, -N(R10)-(CH2)k-CH(R6)-; -O-, -S- o -SO2- donde k es 0 o un entero de 1 a 4; R4, R5, R6, R7, R8, R9 y R10 son cada uno, de modo independiente, (1) un átomo de H, (2) un grupo alquilo C1-6 donde dicho grupo alquilo C1-6 está opcionalmente sustituido con (a) un grupo arilo opcionalmente sustituido, (b) un grupo de anillo heteroaromático opcionalmente sustituido, (c) un grupo carboxi, (d) un grupo alcoxicarbonilo C1-4, (e) -CO-N(R15)(R16) donde R15 y R16 son cada uno, de modo independiente, un átomo de H, un grupo arilo opcionalmente sustituido, un grupo de anillo heteroaromático opcionalmente sustituido, un grupo alquilo C1-6, donde dicho grupo alquilo C1-6 está opcionalmente sustituido con sustituyentes seleccionados del grupo integrado por un grupo arilo opcionalmente sustituido, un grupo de anillo heteroaromático opcionalmente sustituido, un grupo alcoxi C1-4 opcionalmente sustituido con un grupo arilo y un grupo ariloxi opcionalmente sustituido, o pueden formar un anillo indolina junto con el átomo de N unido a el, o pueden formar un anillo hetero de 5 a 7 miembros que opcionalmente contiene al menos un heteroátomo seleccionado del grupo integrado por átomo de N, átomo de O y átomo de S, (f) -N(R15)(R16) donde R15 y R16 son como se definieron con anterioridad, (g) -O-R17 donde R17 es un átomo de H, un grupo arilo opcionalmente sustituido, un grupo de anillo heteroaromático opcionalmente sustituido o un grupo alquilo C1-6, donde dicho grupo alquilo C1-6 está opcionalmente sustituido con sustituyentes seleccionados del grupo integrado por un grupo arilo opcionalmente sustituido, un grupo de anillo heteroaromático opcionalmente sustituido, un grupo alcoxi C1-4 opcionalmente sustituido con un grupo arilo y un grupo ariloxi opcionalmente sustituido, (h) -CO-R17 donde R17 es como se definió con anterioridad; (i) -SO2-R17 donde R17 es como se definió con anterioridad o (j) un grupo cicloalquilo C3-7, (3) -CO-N(R15)(R16) donde R15 y R16 son como se definieron con anterioridad, (4) -SO2-N(R15)(R16) donde R15 y R16 son como se definieron con anterioridad, (5) -CO-R17 donde R17 es como se definió con anterioridad, (6) -SO2-R17 donde R17 es como se definió con anterioridad, (7) un grupo arilo opcionalmente sustituido, (8) un grupo de anillo heteroaromático opcionalmente sustituido, o (9) R4 y R1 están opcionalmente unidos para formar un grupo de fórmula (2) donde i y j son cada uno, de modo independiente, 0, 1 o 2, (10) R5 y R9 están opcionalmente unidos para formar un grupo de fórmula (3) donde a y b son cada uno, de modo independiente, 0, 1 o 2, (11) R5 y R10 están opcionalmente unidos para formar un grupo de fórmula (4) donde k1 y c son cada uno, de modo independiente, 0 o un número entero de 1 a 4, (12) R5 y R10 están opcionalmente unidos para formar un grupo de fórmula (5) donde d y e son cada uno, de modo independiente, 0, 1 o 2, (13) R6 y R10 están opcionalmente unidos para formar un grupo de fórmula (6) donde k1 y c son como se definieron con anterioridad, o (14) R7 y R10 están opcionalmente unidos para formar un grupo de fórmula (7) donde R10´ es un átomo de H o un grupo alquilo C1-6; n es 0 o un número entero de 1 a 4; p es 0 o 1; L es (1) -C(R20)(R21)- donde R20 es (a) un átomo de H, (b) un grupo alquilo C1-6, o (c) opcionalmente unido con R4 o R8 para formar un grupo de fórmula (8) donde n1 y q son cada uno, de modo independiente, 0 o un número entero de 1 a 4, R9´ es un átomo de H, un grupo hidroxilo, un grupo alquilo C1-6, un grupo carboxi o un grupo alcoxi C1-6, o (d) opcionalmente unido con R4 para formar un grupo de fórmula (9) donde u y v son cada uno, de modo independiente, 0, 1, o 2, R21 es un átomo de H, un grupo alquilo C1-6, donde dicho grupo alquilo C1-6 está opcionalmente sustituido con un grupo arilo opcionalmente sustituido o un grupo de anillo heteroaromático opcionalmente sustituido, un grupo arilo opcionalmente sustituido o un grupo de anillo heteroaromático opcionalmente sustituido, (2) el anillo E y sus sustituyentes donde E es un grupo arilo o un grupo de anillo heteroaromático R22 es (a) un átomo de H, (b) un átomo de halógeno, (c) un grupo alquilo C1-4, (d) un grupo alcoxi C1-4 opcionalmente sustituido con un grupo carboxi, (e) un grupo alquiltio C1-6, (f) un grupo nitro, (g) -N(R23)(R24) donde R23 y R24 son cada uno, de modo independiente, un átomo de H, un grupo alquilo C1-6, un grupo alquilcarbonilo C1-4, donde dicho grupo alquilcarbonilo C1-4 está opcionalmente sustituido con un grupo amino, un grupo alquilamino C1-4 o un grupo di(alquil C1-4)amino, o un grupo alquilsulfonilo C1-4, o (h) opcionalmente unido a R4 para formar un grupo de fórmula (10) donde n2 y w son cada uno, de modo independiente, 0 o un número entero de 1 a 3, (i) opcionalmente unido con R4 para formar un grupo de fórmula (11) donde n3 y x son cada uno, de modo independiente, 0 o 1, (j) opcionalmente unido con R7 para formar un grupo de fórmula (12) donde n4 e y son cada uno, de modo independiente, 0, 1 o 2, (k) opcionalmente unido con R7 para formar un grupo de fórmula (13) donde n5 y z son cada uno, de modo independiente, 0 o 1, (l) opcionalmente unido con R8 para formar un grupo de fórmula (14) donde n2 y w son cada uno, de modo independiente, 0 o un número entero de 1 a 3, o (m) opcionalmente unido con R4 para formar un grupo de fórmula (15) o (3) el grupo de fórmula (20) donde R20, R21 y E son como se definieron con anterioridad, R25 es (a) un átomo de H, (b) un átomo de halógeno, (c) un grupo alquilo C1-4, (d) un grupo alcoxi C1-4 opcionalmente sustituido con un grupo carboxi, (e) un grupo alquiltio C1-6, (f) un grupo nitro o (g) -N(R23)(R24) donde R23 y R24 son como se definieron con anterioridad; R es -COO(R19), -A1-COO(R19) u -O-A1-COO(R19), donde A1 es un grupo alquileno C1-4 y R19 es un átomo de H o un grupo alquilo C1-4; B es un grupo arilo o un grupo de anillo heteroaromático; R3 es (1) un átomo de H, (2) un átomo de halógeno, (3) un grupo alquilo C1-8, (4) un grupo alcoxi C1-6, (5) un grupo alquilamino C1-6, (6) un grupo di(alquil C1-6)amino, (7) un grupo ciano, (8) un grupo nitro, (9) un grupo haloalquilo C1-4, (10) -S-R18, donde R18 es un grupo alquilo C1-6 o un grupo arilo, (11) -SO-R18, donde R18 es un grupo alquilo C1-6 o un grupo arilo, (12) -SO2-R18, donde R18 es un grupo alquilo C1-6 o un grupo arilo, (13) un grupo arilo o (14) un grupo heterocíclico; Y es -O-, -S-, -SO-, -SO2-, -N(R11)-, -N(R12)-CO-, -N(R12)-SO2-, -SO2-N(R12)-, -C(R13)(R14)-, -CO-, -C(R13)(R14)-N(R12)-, -CO-N(R12)- o -C(R13)(R14)-O- donde R11 es (1) un átomo de H, (2) un grupo alquilo C1-8 donde dicho alquilo C1-8 está opcionalmente sustituido con sustituyentes seleccionados del grupo integrado por (a) un grupo cicloalquilo C3-7, (b) un grupo arilo opcionalmente sustituido, (c) un grupo heterocíclico opcionalmente sustituido, (d) un grupo hidroxilo, (e) un grupo alquilamino C1-4 y (f) un grupo di(alquil C1-4)amino, (3) un grupo alquenilo C2-4, (4) un grupo alquilsulfonilo C1-4, (5) un grupo alquilcarbonilo C1-4 donde dicho grupo alquilcarbonilo C1-4 está opcionalmente sustituido con un grupo hidroxilo o un grupo alcoxi C1-4, o (6) opcionalmente unido con R3 para formar el anillo B y sus sustituyentes donde t es un número entero de 1 a 4, R12 es (1) un átomo de H, (2) un grupo alquilo C1-8 donde dicho grupo alquilo C1-8 está opcionalmente sustituido con sustituyentes seleccionados del grupo integrado por (a) un grupo cicloalquilo C3-7, (b) un grupo arilo opcionalmente sustituido, (c) un grupo heterocíclico opcionalmente sustituido, (d) un grupo hidroxilo, (e) un grupo alquilamino C1-4 y (f) un grupo di(alquil C1-4)amino, (3) un grupo alquenilo C2-4, (4) un grupo alquilsulfonilo C1-4 o (5) un grupo alquilcarbonilo C1-4 donde dicho grupo alquilcarbonilo C1-4 está opcionalmente sustituido con un grupo hidroxilo o un grupo alcoxi C1-4, R13 y R14 son cada uno, de modo independiente, un átomo de H, un grupo alquilo C1-4, o forman opcionalmente un cicloalcano C3-7 junto con el átomo de C unido a él, o forman opcionalmente, junto con el átomo de C unido a él, un anillo hetero de 5 a 7 miembros que tiene opcionalmente al menos un heteroátomo seleccionado del grupo integrado por átomo de N, átomo de O y átomo de S, con la condición de que, cuando m es 0, p es 1 y L es el grupo de fórmula (20) o un anillo E con sus sustituyentes, donde R20 y R21 son, cada uno, un átomo de H, E es un grupo fenilo, R22 es un átomo de H, un átomo de halógeno, un grupo alquilo C1-4, un grupo alcoxi C1-4 o un grupo nitro, R25 es un átomo de H, un átomo de halógeno, un grupo alquilo C1-4, un grupo alcoxi C1-4 o un grupo nitro, Y debería ser -C(R13)(R14)-N(R12)-, -CO-N(R12)- o -C(R13)(R14)-O-, donde R12, R13 y R14 son como se definieron con anterioridad; s es 0 o 1; A es un grupo alquileno C1-4 opcionalmente sustituido con un grupo cicloalquilo C3-7; Z es (1) un grupo cicloalquilo C3-7, donde dicho grupo cicloalquilo C3-7 está opcionalmente sustituido con un grupo arilo, donde dicho grupo arilo está opcionalmente sustituido con un átomo de halógeno o un grupo alquilo C1-6, o un grupo de anillo heteroaromático, donde dicho grupo de anillo heteroaromático está opcionalmente sustituido con un átomo de halógeno o un grupo alquilo C1-6, (2) un grupo arilo donde dicho grupo arilo está opcionalmente sustituido con sustituyentes seleccion
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TW200500362A (en) 2005-01-01
US20060122181A1 (en) 2006-06-08
EP1553091A4 (en) 2007-01-17
MXPA05010945A (es) 2005-11-25
PE20050018A1 (es) 2005-03-23
AU2004228565A1 (en) 2004-10-21
JP3819415B2 (ja) 2006-09-06
BRPI0409136A (pt) 2006-04-25
NO20055246D0 (no) 2005-11-08
CL2004000778A1 (es) 2005-01-21
CO5700817A2 (es) 2006-11-30
RU2005134659A (ru) 2007-05-27
CA2521830A1 (en) 2004-10-21
KR20050119201A (ko) 2005-12-20
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