AR114065A1 - Inhibidores de glicolato oxidasa y uso de los mismos - Google Patents

Inhibidores de glicolato oxidasa y uso de los mismos

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Publication number
AR114065A1
AR114065A1 ARP180103903A ARP180103903A AR114065A1 AR 114065 A1 AR114065 A1 AR 114065A1 AR P180103903 A ARP180103903 A AR P180103903A AR P180103903 A ARP180103903 A AR P180103903A AR 114065 A1 AR114065 A1 AR 114065A1
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AR
Argentina
Prior art keywords
subscript
diyl
ring
methyl
group
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Application number
ARP180103903A
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English (en)
Inventor
Miguel Xavier Fernandes
Hans Maag
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Orfan Biotech Inc
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Publication date
Application filed by Orfan Biotech Inc filed Critical Orfan Biotech Inc
Publication of AR114065A1 publication Critical patent/AR114065A1/es

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    • 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
    • C07D403/02—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 two hetero rings
    • C07D403/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D231/14—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
    • C07D231/18—One oxygen or sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D231/14—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
    • C07D231/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
    • C07D237/18—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
    • C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
    • 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D417/12—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 linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Urology & Nephrology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (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)

Abstract

La presente proporciona pirazoles, isoxazoles, isotiazoles, tiadiazoles y piridazinas de acuerdo con la fórmula (1) como se describe en el presente documento, y sus sales farmacéuticamente aceptables. También se describen composiciones farmacéuticas y métodos para tratar la hiperoxaluria primaria, tipo I (PH) y cálculos renales. Reivindicación 1: Un compuesto de acuerdo a la fórmula (1), o una sal farmacéuticamente aceptable o éster de alquilo C₁₋₆ del mismo, en donde: el anillo A es seleccionado del grupo conformado por 1,2,3-tiadiazol-4,5-diil, (5-metil)-1H-pirazol-3,4-diil, (5-metil)-isoxazol-3,4-diil, (5-metil)-isotiazol-3,4-diil, y piridazin-3,4-diil; el subíndice n es 0, 1, 2 ó 3; el subíndice m es 0, 1, ó 2; W es seleccionado del grupo conformado por -NR³-, -C(R³)₂-, -O-, -S-, -S(O)-, y -S(O)₂-; cada Y es seleccionado independientemente del grupo conformado por -O- y -C(R⁴)₂-; R¹ es seleccionado del grupo conformado por halo, ciano, heteroarilo de 5 a 6 miembros, y -L-(arilo C₆₋₁₀), donde arilo está opcionalmente sustituido con R¹ᵃ; R² es seleccionado del grupo conformado por H y alquilo C₁₋₆; cada R³ es seleccionado independientemente del grupo conformado por H, alquilo C₁₋₆, y arilalquilo C₇₋₁₆, donde arilo en arilalquilo es opcionalmente sustituidos con R³ᵃ; cada R⁴ es seleccionado independientemente del grupo conformado por H, alquilo C₁₋₆ y arilalquilo C₇₋₁₆, donde arilo en arilalquilo es opcionalmente sustituidos con R⁴ᵃ; o dos R⁴ son tomados juntos para formar alquenilo C₁₋₆; R¹ᵃ es seleccionado independientemente del grupo conformado por halo, ciano, -M-(heterociclil de 8- a 12- miembros), -M-(heteroaril de 5- a 6- miembros), -M-(cicloalquil C₃₋₈), y -M-(aril C₆₋₁₀), donde heterociclil, heteroaril, cicloalquil, y aril son sustituidos opcionalmente con R¹ᵇ; R³ᵃ es seleccionado independientemente del grupo conformado por halo, ciano, alquilo C₁₋₆, alcoxi C₁₋₆, -M-(heterociclil de 8- a 12- miembros), -M-(heteroaril de 5- a 6- miembros), -M-(cicloalquil C₃₋₈), y -M-(aril C₆₋₁₀), donde heterociclil, heteroaril, cicloalquil, y aril son sustituidos opcionalmente con R³ᵇ; R⁴ᵃ es seleccionado independientemente del grupo conformado por halo, ciano, -Q-(heterociclil de 8- a 12- miembros), -Q-(heteroaril de 5- a 6- miembros), -Q-(cicloalquil C₃₋₈), y -Q-(aril C₆₋₁₀), donde heterociclil, heteroaril, cicloalquil, y aril son sustituidos opcionalmente con R⁴ᵇ, cada uno de R¹ᵇ, R³ᵇ, y R⁴ᵇ es seleccionado independientemente del grupo conformado por halo y ciano; L, M, y Q son independientemente seleccionados del grupo conformado por un enlace, -O-, alquileno C₁₋₆, alquenileno C₁₋₆, alquinileno C₁₋₆ y heteroalquileno de 2- a 6- miembros; y cada heterociclil es opcional e independientemente sustituido con uno o más grupos protectores de amina; con la condición que si el anillo A es (5-metil)-isoxazol-3,4-diil, W es -CH₂-, subíndice n es 1, y subíndice m es 1, entonces Y es O; con la condición que si el anillo A es (5-metil)-isoxazol-3,4-diil, W es -CH₂-, y subíndice m es 0, entonces subíndice n es 1, 2, ó 3; con la condición que si el anillo A es (5-metil)-isoxazol-3,4-diil, W es -CH₂-, subíndice n es 1, y subíndice m es 0, entonces R¹ es diferente a 3-bromo, 4-bromo, 3-cloro, 4-cloro, 3-fluoro, y 4-fluoro; con la condición que si el anillo A es (5-metil)-lH-pirazol-3,4-diil, W es -NR³-, R³ es H o alquilo C₁₋₆, y subíndice m es 0, entonces subíndice n es 1, 2, ó 3; con la condición que si el anillo A es (5-metil)-1H-pirazol-3,4-diil, W es -NR³-, R³ es H o alquilo C₁₋₆, subíndice m es 1, e Y es -CH₂-, entonces subíndice n es 1, 2, ó 3; con la condición que si el anillo A es (5-metil)-isoxazol-3,4-diil, W es -NH-, subíndice n es 1, y subíndice m es 0, entonces R¹ es diferente a 3-ciano, 4-ciano, 3-bromo, 4-bromo, 3-cloro, 4-cloro, 3, fluoro, y 4-fluoro; con la condición que si el anillo A es (5-metil)-1H-pirazol-3,4-diil, W es -CH₂-, subíndice n es 1, y subíndice m es 1, entonces Y es O; con la condición que si el anillo A es (5-metil)-1H-pirazol-3,4-diil, W es -CH₂-, y subíndice m es 0, entonces subíndice n es 1, 2, ó 3; con la condición que si el anillo A es (5-metil)-1H-pirazol-3,4-diil, W es -CH₂-, subíndice n es 1, y subíndice m es 0, entonces R¹ es diferente a 3-ciano, 4-ciano, 4-bromo, 3-cloro, 4-cloro, 3-fluoro, 4-fluoro, 3-piridin-3-il, 3-piridin-4-il, 3-(4-cianofenil), 3-(4-fluorofenil), 4-(4-fluorofenil), 3-fenoxifenil, y 4-fenoxifenil; con la condición que si el anillo A es 1,2,3-tiadiazol-4,5-diil, W es -CH₂- o -NH-, y subíndice m es 0, entonces subíndice n es 1, 2, ó 3; con la condición que si el anillo A es 1,2,3-tiadiazol-4,5-diil, W es -S-, Y es -CH₂-, y subíndice m es 1, entonces subíndice n es 1, 2, ó 3; con la condición que si el anillo A es 1,2,3-tiadiazol-4,5-diil, W es S, subíndice n es 1, y subíndice m es 0, entonces R¹ es diferente a 4-cloro; con la condición que si el anillo A es 1,2,3-tiadiazol-4,5-diil, W es -NR³-, Y es -CHR⁴-, R³ es butil, R⁴ es H, subíndice n es 1, y subíndice m es 1, entonces R¹ es diferente a 4-(2H-tetrazol-5-il)fenil; con la condición que si el anillo A es piridazin-3,4-diil, W es -NR³-, Y es -CHR⁴-, R³ es propil, R⁴ es H, subíndice n es 1, y subíndice m es 1, entonces R¹ es diferente a 4-(2H-tetrazol-5-il)fenil.
ARP180103903A 2017-12-29 2018-12-28 Inhibidores de glicolato oxidasa y uso de los mismos AR114065A1 (es)

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US11389456B2 (en) 2018-02-23 2022-07-19 Oxalurx, Inc. Compounds and methods for treating oxalate-related diseases
JP7348705B2 (ja) 2018-07-06 2023-09-21 カンテロ セラピューティクス，インコーポレイティド トリアゾールグリコール酸オキシダーゼ阻害剤
KR20220051213A (ko) * 2019-08-22 2022-04-26 옥살럭스 인코포레이티드 옥살레이트-관련 질환의 치료를 위한 화합물 및 방법
AU2020376792A1 (en) 2019-11-01 2022-05-26 Lilac Therapeutics, Inc. Heterocyclic carboxylate compounds as glycolate oxidase inhibitors
CN114230518A (zh) * 2021-12-13 2022-03-25 海南梵圣生物科技有限公司 一种5-苄基-1h-吲唑-3-胺类化合物的制备方法

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US7022702B2 (en) * 2000-04-07 2006-04-04 Qlt Inc. Antiproliferative 1,2,3-thiadiazole compounds
PT1682138E (pt) * 2003-11-19 2011-02-28 Array Biopharma Inc Inibidores heterocíclicos de mek
CA2580845A1 (en) * 2004-09-20 2006-03-30 Xenon Pharmaceuticals Inc. Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase
RU2627661C2 (ru) * 2012-01-10 2017-08-09 Ф. Хоффманн-Ля Рош Аг Соединения пиридазинамида и их применение в качестве ингибиторов тирозинкиназы селезенки (syk)
EP3386949A4 (en) * 2015-12-07 2019-11-20 Wake Forest University Health Sciences GLYCOLATE OXIDASE INHIBITORS AND METHODS OF USE FOR THE TREATMENT OF RENAL CALCULATIONS

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