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AR115965A1 - Derivados heteroaromáticos de carboxamida como inhibidores de la calicreína plasmática - Google Patents

Derivados heteroaromáticos de carboxamida como inhibidores de la calicreína plasmática

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Publication number
AR115965A1
AR115965A1 ARP190102330A ARP190102330A AR115965A1 AR 115965 A1 AR115965 A1 AR 115965A1 AR P190102330 A ARP190102330 A AR P190102330A AR P190102330 A ARP190102330 A AR P190102330A AR 115965 A1 AR115965 A1 AR 115965A1
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AR
Argentina
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optionally substituted
alkyl
group
membered
ring
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Application number
ARP190102330A
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English (en)
Inventor
Dieter Wiedenmayer
Holger Wagner
Elke Langkopf
Andreas Gollner
Matthias Eckhardt
Original Assignee
Boehringer Ingelheim Int
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Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int
Publication of AR115965A1 publication Critical patent/AR115965A1/es

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    • 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
    • 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
    • C07D401/14—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
    • 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
    • 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
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with 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
    • A61K31/535—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
    • A61K31/5386—1,4-Oxazines, e.g. morpholine spiro-condensed or forming part of bridged ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/08—Bridged systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Carboxamidas heteroaromáticas de la fórmula (1), en donde Y, R, y X son como se definen en la descripción y las reivindicaciones, y sales de aquellos aceptables desde el punto de vista farmacéutico se pueden usar en los métodos para el tratamiento de enfermedades que pueden verse influenciadas por la inhibición de la calicreína plasmática. Reivindicación 1: Un compuesto caracterizado por la fórmula (1), en donde Y se selecciona del grupo Y-G¹ que consiste en los compuestos del grupo de fórmulas (2), cada uno de los cuales se sustituye con 1 ó 2 sustituyentes independientes R¹; R se selecciona del grupo R-G¹ que consiste en sistemas de anillos monocíclicos de 4 a 7 miembros saturados y bicíclicos de 6 a 12 miembros saturados, que contiene de 1 a 3 átomos de N como miembros del anillo y, de manera opcional, 1 a 2 miembros del anillo seleccionados del grupo que consiste en C=O, O, S, S=O y SO₂, siempre que los sistemas de anillos no contengan ningún enlace heteroátomo-heteroátomo entre miembros del anillo, en donde dichos sistemas de anillos están unidos a Y en la fórmula (1) mediante un átomo de N, y en donde dichos sistemas de anillos se sustituyen opcionalmente con de 1 a 6 F, se sustituyen opcionalmente con 1 sustituyente R², y se sustituyen opcionalmente con 1 ó 2 grupos CH₃; X se selecciona del grupo X-G¹ que consiste en heteroarilos de 5 miembros, que contienen de 1 a 4 átomos de N o que contienen 1 átomo de O ó S o que contienen de 1 a 3 átomos de N y 1 átomo de O ó S, y heteroarilos de 9 miembros, que consisten en un anillo de 5 miembros fusionado a un anillo de 6 miembros y que contienen de 1 a 5 átomos de N, en donde dichos heteroarilos están unidos al grupo carbonilo en la fórmula (1) mediante un átomo de C del anillo de 5 miembros y al grupo CH₂ en la fórmula (1) mediante un átomo de C o N no adyacente del anillo de 5 miembros, y en donde dichos heteroarilos se sustituyen opcionalmente con 1 sustituyente R³; R¹ se selecciona del grupo R¹-G¹ que consiste en H, C₁₋₄ alquilo opcionalmente sustituido con de 1 a 5 F ciclopropilo opcionalmente sustituido con 1 F o 1 grupo CH₃, CN, OH, O-C₁₋₃ alquilo opcionalmente sustituido con de 1 a 5 F, C₁₋₃ alquilo opcionalmente sustituido con 1 sustituyente seleccionado del grupo que consiste en CN, OH, y O-CH₃; R² se selecciona del grupo R²-G¹ que consiste en Cl, C₁₋₄ alquilo opcionalmente sustituido con de 1 a 5 F, C₃₋₄ cicloalquilo, C₁₋₃ alquilen-OH, C₁₋₃ alquilen-O-C₁₋₄ alquilo, CN, COOH, NH₂, NH-C₁₋₃ alquilo, N(C₁₋₃ alquilo)₂, OH, O-C₁₋₄ alquilo opcionalmente sustituido con de 1 a 5 F, fenilo, heteroarilos de 5 miembros que contienen 1 miembro del anillo -NH-, -N<, -O- o -S- y, opcionalmente, de manera adicional, 1 ó 2 miembros del anillo =N-, y heteroarilos de 6 miembros que contienen 1 ó 2 miembros del anillo =N-; en donde dichos fenilo y heteroarilos de 5 y 6 miembros se sustituyen opcionalmente en 1 ó 2 átomos de carbono independientemente entre sí con F, Cl, CH₃, CF₃, CN, OH, y/o O-CH₃, y en donde los grupos N-H presentes dentro de estos anillos se reemplazan opcionalmente por N-C₁₋₃ alquilo; R³ se selecciona del grupo R³-G¹ que consiste en F, Cl, Br, CN, COOH, C₁₋₄ alquilo opcionalmente sustituido con de 1 a 5 F, C₃₋₅ cicloalquilo, C₁₋₃ alquilen-OH, C₁₋₃ alquilen-O-C₁₋₄ alquilo, O-C₁₋₄ alquilo opcionalmente sustituidos con de 1 a 5 F, heteroarilos de 5 miembros que contienen 1 miembro del anillo -NH-, -O- o -S- y opcionalmente, de manera adicional, 1 ó 2 miembros del anillo =N-, y heteroarilos de 6 miembros que contienen 1 ó 2 miembros del anillo =N-; en donde dichos heteroarilos de 5 y 6 miembros se sustituyen opcionalmente en 1 ó 2 átomos de carbono independientemente entre sí con F, Cl, CH₃, CF₃, CN, OH, y/o O-CH₃, y en donde los grupos N-H presentes dentro de estos anillos se reemplazan opcionalmente por N-C₁₋₃ alquilo; y/o sus tautómeros o una sal de estos.
ARP190102330A 2018-08-16 2019-08-15 Derivados heteroaromáticos de carboxamida como inhibidores de la calicreína plasmática AR115965A1 (es)

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US (1) US10695334B2 (es)
EP (1) EP3837252A1 (es)
JP (1) JP6828191B2 (es)
CN (1) CN113039181B (es)
AR (1) AR115965A1 (es)
TW (1) TW202021586A (es)
WO (1) WO2020035540A1 (es)

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WO2020074442A1 (en) 2018-10-10 2020-04-16 Boehringer Ingelheim International Gmbh Phenyltetrazole derivatives as plasma kallikrein inhibitors
TW202144331A (zh) * 2020-02-13 2021-12-01 德商百靈佳殷格翰國際股份有限公司 作為血漿激肽釋放酶抑制劑之雜芳族甲醯胺衍生物
BR112022013979A2 (pt) 2020-02-13 2022-10-11 Boehringer Ingelheim Int Derivados de carboxamida heteroaromáticos como inibidores da calicreína plasmática
EP4178620A4 (en) * 2020-07-10 2024-08-07 Merck Sharp & Dohme LLC PLASMA KALLICREIN INHIBITORS
CA3217423A1 (en) 2021-06-16 2022-12-22 Jeffrey M. Schkeryantz Azetidinyl compounds comprising a carboxylic acid group for the treatment of neurodegenerative diseases
CN118084767A (zh) * 2024-04-02 2024-05-28 康龙化成手性医药技术(宁波)有限公司 一种外型-6-氟甲基-3-氮杂双环[3,1,0]己烷盐酸盐及其衍生物的合成方法

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JP2005089362A (ja) 2003-09-17 2005-04-07 Sumitomo Chemical Co Ltd アリールピラゾリン化合物及びその用途
WO2009097141A1 (en) 2008-01-31 2009-08-06 Joslin Diabetes Center Methods for treatment of kallikrein-related disorders
EP2807157A1 (en) 2012-01-27 2014-12-03 Novartis AG 5-membered heteroarylcarboxamide derivatives as plasma kallikrein inhibitors
WO2013111107A1 (en) 2012-01-27 2013-08-01 Novartis Ag Aminopyridine derivatives as plasma kallikrein inhibitors
ES2909885T3 (es) 2013-05-23 2022-05-10 Kalvista Pharmaceuticals Ltd Inhibidores de la calicreína plasmática
CA2920815C (en) * 2013-08-14 2021-09-21 Kalvista Pharmaceuticals Limited Inhibitors of plasma kallikrein
US10640486B2 (en) * 2015-10-27 2020-05-05 Boehringer Ingelheim International Gmbh Heteroarylcarboxamide derivatives as plasma kallikrein inhibitors
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EP3481391A4 (en) * 2016-07-11 2020-03-11 Lifesci Pharmaceuticals, Inc. THERAPEUTIC INHIBITOR COMPOUNDS

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US10695334B2 (en) 2020-06-30
JP2020529389A (ja) 2020-10-08
CN113039181A (zh) 2021-06-25
CN113039181B (zh) 2024-08-13
EP3837252A1 (en) 2021-06-23
WO2020035540A1 (en) 2020-02-20
JP6828191B2 (ja) 2021-02-10
TW202021586A (zh) 2020-06-16

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