AR114070A1 - Inhibidores de glicolato oxidasa para el tratamiento de una enfermedad - Google Patents
Inhibidores de glicolato oxidasa para el tratamiento de una enfermedadInfo
- Publication number
- AR114070A1 AR114070A1 ARP180103914A ARP180103914A AR114070A1 AR 114070 A1 AR114070 A1 AR 114070A1 AR P180103914 A ARP180103914 A AR P180103914A AR P180103914 A ARP180103914 A AR P180103914A AR 114070 A1 AR114070 A1 AR 114070A1
- Authority
- AR
- Argentina
- Prior art keywords
- ring
- alkyl
- phenyl
- halo
- cycloalkyl
- Prior art date
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract 6
- 201000010099 disease Diseases 0.000 title abstract 3
- 108010062584 glycollate oxidase Proteins 0.000 title abstract 3
- 102100038837 2-Hydroxyacid oxidase 1 Human genes 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 18
- 125000000217 alkyl group Chemical group 0.000 abstract 15
- 125000005843 halogen group Chemical group 0.000 abstract 15
- 125000003545 alkoxy group Chemical group 0.000 abstract 14
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 12
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 5
- -1 2,3-dihydrobenzo [b] [1,4] dioxinyl Chemical group 0.000 abstract 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract 4
- 229910052717 sulfur Inorganic materials 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 208000035475 disorder Diseases 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 abstract 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 abstract 2
- 125000001041 indolyl group Chemical group 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 abstract 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 208000004777 Primary Hyperoxaluria Diseases 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 abstract 1
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 abstract 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000002431 aminoalkoxy group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 abstract 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 abstract 1
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 abstract 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 abstract 1
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000005046 dihydronaphthyl group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 abstract 1
- 230000004060 metabolic process Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000001425 triazolyl group Chemical group 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- 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
- A61K31/41—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
-
- 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
-
- 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
-
- 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
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- 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
- C07D401/04—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
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- 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
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
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- 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
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- 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
-
- 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
- C07D417/04—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
En la presente se describen compuestos, métodos de fabricación de esos compuestos, composiciones farmacéuticas y medicamentos que contienen dichos compuestos, y métodos de uso de los compuestos para tratar o prevenir enfermedades o trastornos en relación con la enzima glicolato oxidasa (GO). Tales enfermedades o trastornos incluyen, por ejemplo, trastornos del metabolismo del glioxilato, incluso hiperoxaluria primaria, que se asocian a la producción excesiva de oxalato. Reivindicación 1: Un compuesto de la fórmula (1) en donde: el anillo C se selecciona los compuestos de fórmula (2) y (3); en donde las líneas ondeadas (~~~~) indican los puntos de unión del C₁ carbono al carbonilo de C(O)-OR¹, y el C₂ carbono a L; L es un enlace, CH₂, CF₂, O, NRL, S, S(=O), C(=O), CH₂-Q o Q-CH₂; en donde Q es O, NRL o S; RL es hidrógeno o C₁₋₄ alquilo, C₃₋₆ cicloalquilo, fenilo o bencilo; en donde el C₁₋₄ alquilo se sustituye opcionalmente con hidroxicarbonilo, alcoxicarbonilo, hidroxicarbonilalquilo o alquilcarboniloxi; y el grupo fenilo solo o como parte del grupo bencilo se sustituye opcionalmente con uno o dos grupos seleccionados de halo y haloalcoxi; el anillo A es C₃₋₈ cicloalquilo, C₈₋₁₁ espirocicloalquilo, heterocicloalquilo de 5 a 8 miembros, pirazolilo, imidazolilo, triazolilo, tiazolilo, tienilo, fenilo, naftilo, indanilo, tetrahidronaftilo, dihidronaftilo, piridilo, indolilo, benzotiazolilo, quinolinilo, isoquinolinilo, indolinilo, isoindolinilo, tetrahidroquinolinilo, dihidroisoquinolinilo, tetrahidroisoquinolinilo, 2,3-dihidrobenzo[b][1,4]dioxinilo o tetrahidro-metanonaftalenilo; el anillo B está o no presente; en donde: si el anillo B está presente, entonces el anillo A se sustituye opcionalmente con uno o dos grupos independientemente seleccionados de halo, alquilo, alcoxi, ciano, hidroxi, haloalcoxi, (cicloalquil)alcoxi y cicloalquilo; si el anillo B no está presente y el anillo A es fenilo, entonces el anillo A se sustituye con: (i) uno o dos grupos RAA; (ii) dos grupos halo cuando L es distinto a O; (iii) dos grupos halo cuando L es O, y R² y R³ no son hidrógeno o alquilo; (iv) un grupo halo cuando L es CH₂NRL; (v) un grupo halo y un grupo seleccionado del grupo que consiste en haloalcoxi, cicloalquiloxi, (cicloalquil)alcoxi y (fenil)alcoxi, cuando L es un enlace, O, S o S(=O), en donde el fenilo se sustituye opcionalmente con halo, ciano, haloalquilo o haloalcoxi; o (vi) un grupo ciano y un grupo (fenil)alcoxi, cuando L es un enlace u O, en donde el fenilo como parte del grupo (fenil)alcoxi se sustituye opcionalmente con halo o haloalcoxi; si el anillo B no está presente y el anillo A es distinto a fenilo, entonces (i) el anillo A se sustituye con uno o dos grupos RAB o (ii) el anillo A es no sustituido, en donde: 1) cuando el anillo A es tetrahidroquinolinilo no sustituido, entonces L es un enlace; 2) cuando el anillo A es no sustituido 2,3-dihidrobenzo[b][1,4]dioxinilo, entonces L es O; 3) cuando el anillo A es tetrahidronaftilo no sustituido, entonces L es O, y R¹ no es hidrógeno o etilo; o 4) cuando el anillo A es espirocicloalquilo no sustituido, entonces L es O, S O CH₂S; cada RAA es independientemente alquilo; haloalquilo; haloalcoxi; cicloalquiloxi; (cicloalquil)alcoxi; fenoxi opcionalmente sustituido con uno o dos grupos halo; o alquilcarbonilaminoalcoxi; cada RAB es independientemente halo; alquilo; hidroxi; alcoxi; haloalquilo; haloalcoxi; cicloalquiloxi; (cicloalquil)alcoxi; o fenoxi opcionalmente sustituido con uno o dos grupos halo; el anillo B, si está presente, es cicloalquilo, heterocicloalquilo, arilo o heteroarilo; en donde cada uno se sustituye opcionalmente con 1, 2 ó 3 grupos RB; cada RB es independientemente halo; ciano; alquilo; hidroxialquilo; alquilsulfonilo; aminosulfonilo; alquilaminosulfonilo; dialquilaminosulfonilo; haloalquilo; alcoxi; aminoalcoxi; alquilaminoalcoxi; dialquilaminoalcoxi; hidroxialcoxi; haloalcoxi; alquilcarbonilo; alcoxialcoxi; aminocarbonilo; alquilaminocarbonilo; dialquilaminocarbonilo; alquilcarbonilaminoalcoxi; cicloalquilo; (cicloalquil)alquilo; cicloalquiloxi; (cicloalquil)alcoxi, en donde el grupo cicloalquilo se sustituye opcionalmente con hidroxialquilo; cicloalquilcarbonilo; cicloalquilcarboniloxi; heterocicloalquilo opcionalmente sustituido con uno o dos grupos independientemente seleccionados de halo, alquilo y alquilcarbonilo; (heterocicloalquil-ona de 5 a 6 miembros)alquilo; heterocicloalquil-ona de 5 a 6 miembros; (heterocicloalquil)alquilo; heterocicloalquilcarbonilo; o heteroarilo de 5 a 6 miembros opcionalmente sustituido con un grupo seleccionado de alquilo, hidroxialquilo, (hidroxicicloalquil)alquilo, alcoxialquilo y hidroxicicloalquilo; R¹ es hidrógeno, alquilo, cicloalquilo, heterocicloalquilo o W; en donde W es alquilo sustituido con amino, alquilamino, dialquilamino, alquilcarboniloxi, alcoxicarbonilo, fenilcarboniloxi, aminocarboniloxi, alquilaminocarboniloxi, dialquilaminocarboniloxi, alcoxicarboniloxi, cicloalquilcarboniloxi, N(R¹A)C(O)R¹B, -N(R¹A)C(O)OR¹B o -N(R¹A)C(O)NR¹BR¹C; en donde R¹A, R¹B y R¹C son, cada uno independientemente, hidrógeno o C₁₋₆ alquilo; R² y R³ son independientemente hidrógeno, alquilo, fenilo, bencilo o bencilo sustituido con alcoxi; en donde el alquilo se sustituye opcionalmente con halo, alcoxi, haloalcoxi, alquilcarboniloxi, cicloalquilcarboniloxi o heterocicloalquilcarboniloxi opcionalmente sustituido con alcoxicarbonilo; siempre que: i) cuando L es S o CH₂, y el anillo A es fenilo distinto a fenilo sustituido con (cicloalquil)alcoxi, entonces el anillo B no puede ser fenilo sustituido con halo; ii) cuando L es O, el anillo A es fenilo, y el anillo B no está presente, entonces RAA no puede ser alquilo; iii) cuando L es O, el anillo A es fenilo sustituido con 1 RAA, y el anillo B no está presente, entonces RAA no puede ser trifluorometilo sustituido con meta; iv) cuando L es O, el anillo A es fenilo, el anillo B no está presente, y R¹ es etilo, entonces RAA no puede ser trifluorometoxi; v) cuando L es un enlace, el anillo A es distinto a fenilo, el anillo B no está presente, y R¹ es H, entonces RAB no puede ser metilo; y vi) cuando L es NH, el anillo A es piridilo, indolilo o indolinilo, y el anillo B no está presente, entonces RAB no puede ser alquilo; y opcionalmente un solo estereoisómero o una mezcla de estereoisómeros de aquellos y opcionalmente de manera adicional una sal de este aceptable desde el punto de vista farmacéutico.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762611995P | 2017-12-29 | 2017-12-29 | |
| US201862765313P | 2018-08-20 | 2018-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
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| EP (1) | EP3732167A2 (es) |
| JP (2) | JP7344878B2 (es) |
| KR (1) | KR20200112860A (es) |
| CN (6) | CN117126151A (es) |
| AR (1) | AR114070A1 (es) |
| AU (1) | AU2018395275A1 (es) |
| BR (1) | BR112020013073A2 (es) |
| CA (1) | CA3086401A1 (es) |
| CL (1) | CL2020001742A1 (es) |
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| PE (1) | PE20201500A1 (es) |
| SG (1) | SG11202005807QA (es) |
| TW (2) | TWI811282B (es) |
| WO (1) | WO2019133770A2 (es) |
Families Citing this family (15)
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| PE20201500A1 (es) * | 2017-12-29 | 2020-12-29 | Biomarin Pharm Inc | Inhibidores de glicolato oxidasa para el tratamiento de enfermedades |
| US11389456B2 (en) | 2018-02-23 | 2022-07-19 | Oxalurx, Inc. | Compounds and methods for treating oxalate-related diseases |
| KR102865323B1 (ko) * | 2018-07-06 | 2025-09-26 | 칸테로 테라퓨틱스, 인코포레이티드 | 트리아졸 글리콜레이트 옥시다아제 억제제 |
| CA3151932A1 (en) | 2019-08-22 | 2021-02-25 | Oxalurx, Inc. | Compounds and methods for treating oxalate-related diseases |
| JP7439248B2 (ja) | 2019-11-01 | 2024-02-27 | ライラック セラピューティクス， インク． | グリコール酸オキシダーゼ阻害剤としてのヘテロ環式カルボキシレート化合物 |
| WO2021142155A1 (en) * | 2020-01-08 | 2021-07-15 | Orfan Biotech Inc. | Processes for preparing triazole glycolate oxidase inhibitors |
| CN115702146B (zh) * | 2020-06-30 | 2024-10-18 | 苏州恩华生物医药科技有限公司 | 5-((1,2,3,4-四氢异喹啉-7-基)氨基)吡啶-2(1h)-酮衍生物及其应用 |
| MX2023001438A (es) | 2020-08-04 | 2023-06-15 | Calcilytix Therapeutics Inc | Formulaciones de compuestos calciliticos de trifenilo. |
| WO2022066933A1 (en) * | 2020-09-24 | 2022-03-31 | Chinook Therapeutics Canada, Inc. | Pentafluoro-sulfanyl -substituted triazolyl compounds and methods of use thereof |
| CN114478210A (zh) * | 2022-02-26 | 2022-05-13 | 江苏壹药新材料有限公司 | 一种7-氯萘-2-甲醛的合成方法 |
| WO2023170024A1 (en) * | 2022-03-11 | 2023-09-14 | University Of Copenhagen | Camk2 modulators and their use in medicine |
| GB202213162D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Prodrugs |
| WO2024109917A1 (zh) * | 2022-11-25 | 2024-05-30 | 西藏海思科制药有限公司 | 一种三唑衍生物及其在医药上的应用 |
| WO2024212137A1 (en) * | 2023-04-12 | 2024-10-17 | Cantero Therapeutics, Inc. | Crystalline forms of a 1h-1, 2, 3-triazole-4-carboxylic acid compound |
| WO2025206002A1 (ja) * | 2024-03-28 | 2025-10-02 | 日本曹達株式会社 | トリアゾール化合物および農園芸用殺菌剤 |
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| DE2757929A1 (de) * | 1977-12-24 | 1979-07-05 | Boehringer Sohn Ingelheim | Neue pyrido-eckige klammer auf 1,2-a eckige klammer zu -v-triazolo- eckige klammer auf 4,5-d eckige klammer zu pyrimidinone, deren salze und verfahren zu deren herstellung |
| JPS5519292A (en) * | 1978-07-24 | 1980-02-09 | Beecham Group Ltd | Benzopyranotriazoles*their manufacture and medical composition containing them |
| DE2966444D1 (en) | 1978-07-24 | 1984-01-05 | Beecham Group Plc | Benzopyranotriazoles, preparation of these compounds and pharmaceutical composition containing them |
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2018
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- 2018-12-28 TW TW107147699A patent/TWI811282B/zh not_active IP Right Cessation
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- 2018-12-28 CN CN202310936618.8A patent/CN117126151A/zh active Pending
- 2018-12-28 US US16/958,511 patent/US11384055B2/en active Active
- 2018-12-28 KR KR1020207022038A patent/KR20200112860A/ko not_active Ceased
- 2018-12-28 CN CN202310936523.6A patent/CN117069712A/zh active Pending
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- 2018-12-28 JP JP2020535997A patent/JP7344878B2/ja active Active
- 2018-12-28 EP EP18840000.6A patent/EP3732167A2/en not_active Withdrawn
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- 2018-12-28 CN CN202310936668.6A patent/CN117126152A/zh active Pending
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2020
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2022
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2023
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