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AR110241A1 - Ácidos indanilaminopiridil-ciclopropano-carboxílicos, composiciones farmacéuticas y usos de los mismos - Google Patents

Ácidos indanilaminopiridil-ciclopropano-carboxílicos, composiciones farmacéuticas y usos de los mismos

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Publication number
AR110241A1
AR110241A1 ARP170103293A ARP170103293A AR110241A1 AR 110241 A1 AR110241 A1 AR 110241A1 AR P170103293 A ARP170103293 A AR P170103293A AR P170103293 A ARP170103293 A AR P170103293A AR 110241 A1 AR110241 A1 AR 110241A1
Authority
AR
Argentina
Prior art keywords
alkyl
group
nrn
cycloalkyl
heterocyclyl
Prior art date
Application number
ARP170103293A
Other languages
English (en)
Inventor
Stefan Peters
Holger Wagner
Matthias Eckhardt
Original Assignee
Boehringer Ingelheim Int
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Filing date
Publication date
Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int
Publication of AR110241A1 publication Critical patent/AR110241A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
    • 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
    • A61K31/4427—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
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • 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
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
    • 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—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
    • C07D405/02—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
    • 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
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Compuestos que tienen valiosas propiedades farmacológicas que, en particular, se unen al receptor GPR40 y modulan su actividad. Los compuestos son adecuados para el tratamiento y la prevención de enfermedades que pueden ser influenciadas por este receptor, tales como las enfermedades metabólicas, en particular la diabetes de tipo 2. Además, productos intermedios, útiles para la síntesis de tales compuestos. Reivindicación 1: Un compuesto caracterizado por la fórmula (1), en la que R se selecciona del grupo que consiste en H, F, Cl, Br, I, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, NC-, HNRN-C(=O)-, alquilo C₁₋₄-NRN-C(=O)-, cicloalquilo C₃₋₆-NRN-C(=O)-, heterociclilo-NRN-C(=O)-, heteroarilo-NRN-C(=O)-, HOOC-, alquilo C₁₋₄-OC(=O)-, O₂N-, HRNN-, alquilo C₁₋₄-RNN-, alquilo C₁₋₄-C(=O)NRN-, cicloalquilo C₃₋₆-C(=O)NRN-, heterociclilo-C(=O)-NRN-, heteroarilo-C(=O)NRN-, alquilo C₁₋₄-S(=O)₂NRN-, cicloalquilo C₃₋₆-S(=O)₂NRN-, heterociclilo-S(=O)₂NRN-, heteroarilo-S(=O)₂NRN-, HO-, alquilo C₁₋₆-O-, HOOC-alquilo C₁₋₃-O-, heterociclilo C₁₋₃-O-, fenil-alquilo C₁₋₃-O-, cicloalquilo C₃₋₆-O-, heterociclilo-O-, heteroarilo-O-, alquilo C₁₋₄-S-, cicloalquilo C₃₋₆-S-, heterociclilo-S-, alquilo C₁₋₄-S(=O)-, cicloalquilo C₃₋₆-S(=O)-, heterociclilo-S(=O)-, alquilo C₁₋₄-S(=O)₂-, cicloalquilo C₃₋₆-S(=O)₂-, heterociclilo-S(=O)₂-, fenilo-S(=O)₂-, heteroarilo-S(=O)₂-, HNRN-S(=O)₂-, alquilo C₁₋₄-NRN-S(=O)₂-, heterociclilo, fenilo, y heteroarilo, en la que cada grupo o subgrupo alquilo, cicloalquilo, y heterociclilo dentro de los grupos que forman R está opcionalmente sustituido con 1 o más átomos de F y opcionalmente sustituido con 1 a 3 grupos seleccionados en forma independiente de Cl, alquilo C₁₋₃, NC-, (RN)₂N-, HO-, alquilo C₁₋₃-O-, y alquilo C₁₋₃-S(=O)₂-; y en el que cada grupo o subgrupo fenilo y heteroarilo dentro de los grupos que forman R está opcionalmente sustituido con 1 a 5 sustituyentes seleccionados en forma independiente de F, Cl, alquilo C₁₋₃, HF₂C-, F₃C-, NC-, (RN)₂N-, HO-, alquilo C₁₋₃-O-, F₃C-O-, y alquilo C₁₋₃-S(=O)₂-; en la que cada grupo o subgrupo heterociclilo dentro de los grupos que forman R se selecciona de un grupo ciclobutilo en el que 1 grupo CH₂ está reemplazado por NRN- u -O-; un grupo cicloalquilo C₅₋₆ en el que 1 grupo CH₂ está reemplazado por -C(=O)-, NRN-, -O- o -S(=O)₂- y/o 1 grupo CH está reemplazado por N; un grupo cicloalquilo C₅₋₆ en el que 1 grupo CH₂ está reemplazado por NRN- u -O-, un segundo grupo CH₂ está reemplazado por NRN-, -C(=O)- o -S(=O)₂- y/o 1 grupo CH está reemplazado por N; y un grupo cicloalquilo C₅₋₆ en el que 2 grupos CH₂ están reemplazados por NRN- o 1 grupo CH₂ por -NRN- y el otro por -O- y un tercer grupo CH₂ está reemplazado por -C(=O)- o -S(=O)₂- y/o 1 grupo CH está reemplazado por N; en el que cada grupo o subgrupo heteroarilo dentro de los grupos que forman R se selecciona de tetrazolilo y un anillo heteroaromático de 5 ó 6 miembros que contiene 1, 2, ó 3 heteroátomos en forma independiente el uno del otro seleccionados de =N-, -NRN-, -O-, y -S-, en el que en los grupos heteroaromáticos que contienen una unidad -HC=N- este grupo está reemplazado en forma opcional por -NRN-C(=O)-; en el que en los anillos de heteroarilo y heterociclilo con uno o más grupos NH, cada uno de dichos grupos NH está reemplazado por NRN; R¹ se selecciona del grupo que consiste en H, F, Cl, alquilo C₁₋₄, cicloalquilo C₃₋₆, HO-alquilo C₁₋₄, alquilo C₁₋₄-O-alquilo C₁₋₄, NC-, HO-, alquilo C₁₋₄-O-, cicloalquilo C₃₋₆-O-, alquilo C₁₋₄-S-, alquilo C₁₋₄-S(O)-, y alquilo C₁₋₄-S(O)₂-, en el que cualquier grupo o subgrupo alquilo y cicloalquilo dentro de los grupos que forman R¹ está opcionalmente sustituido con 1 o más átomos de F, y en el que múltiples R¹ pueden ser iguales o diferentes si mes es 2, 3 ó 4; m es un número entero seleccionado de 1, 2, 3, y 4; R² se selecciona del grupo que consiste en H, F, Cl, alquilo C₁₋₄, NC-, y alquiloxi C₁₋₄, en el que cualquier grupo o subgrupo alquilo dentro de los grupos que forman R² está opcionalmente sustituido con 1 o más átomos de F, y en el que múltiples R² pueden ser idénticos o diferentes si n es 2 ó 3; R³ se selecciona del grupo que consiste en H, F, Cl, alquilo C₁₋₄, NC-, y alquilo C₁₋₄-O-, en el que cada grupo o subgrupo alquilo dentro de los grupos que forman R³ está opcionalmente sustituido con 1 o más átomos de F; n es un número entero seleccionado de 1, 2, y 3; RN está seleccionado independientemente uno de otro del grupo que consiste en H, alquilo C₁₋₄, HO-alquilo C₁₋₄-(H₂C)-, alquilo C₁₋₃-O-alquilo C₁₋₄, alquilo C₁₋₄-C(=O)-, alquilo C₁₋₄-NH-C(=O)-, alquilo C₁₋₄-N(alquilo C₁₋₄)-C(=O)-, alquilo C₁₋₄-OC(=O)-, y alquilo C₁₋₄-S(=O)₂-, en el que cada grupo o subgrupo alquilo dentro de los grupos que forman RN está opcionalmente sustituido con 1 o más átomos de F; en la que en cualquier definición mencionada con anterioridad, si no se específica otra cosa, cualquier grupo o subgrupo alquilo pueden ser de cadena lineal o ramificada; o una sal del mismo. Reivindicación 17: Un compuesto caracterizado por la estructura y la estereoquímica que se muestra en las fórmulas (2), (3), (4) y (5), en las que R³ es H, R’ es H o alquilo C₁₋₄, y LG es Cl, Br, o I; o una sal de los mismos.
ARP170103293A 2016-11-28 2017-11-27 Ácidos indanilaminopiridil-ciclopropano-carboxílicos, composiciones farmacéuticas y usos de los mismos AR110241A1 (es)

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US (1) US10125101B2 (es)
EP (1) EP3544958B1 (es)
JP (1) JP7008704B2 (es)
CN (1) CN110312706B (es)
AR (1) AR110241A1 (es)
TW (1) TW201831451A (es)
WO (1) WO2018095877A1 (es)

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