AR110412A1 - Inhibidores de la cyp11a1 - Google Patents

Inhibidores de la cyp11a1

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Publication number
AR110412A1
AR110412A1 ARP170103609A ARP170103609A AR110412A1 AR 110412 A1 AR110412 A1 AR 110412A1 AR P170103609 A ARP170103609 A AR P170103609A AR P170103609 A ARP170103609 A AR P170103609A AR 110412 A1 AR110412 A1 AR 110412A1
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AR
Argentina
Prior art keywords
alkyl
methyl
pyran
isoquinolinyl
dihydro
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ARP170103609A
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English (en)
Inventor
Gerd Wohlfahrt
Matti Vaismaa
Eija Tiainen
Petteri Rummakko
Pekka Pietikinen
Mikko Passiniemi
Mikko Mkel
Belle David Din
Original Assignee
Orion Corp
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Publication of AR110412A1 publication Critical patent/AR110412A1/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
    • A61K31/40—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
    • A61K31/4035—Isoindoles, e.g. phthalimide
    • 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
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non 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
    • A61K31/435—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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine 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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene
    • 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
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D405/14—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 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
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D417/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • 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
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

Los compuestos de fórmula (1) poseen actividad como inhibidores de la citocromo P450 monooxigenasa 11A1 (CYP11A1). Los compuestos son útiles como medicamentos en el tratamiento de enfermedades y condiciones dependientes de un receptor esteroide, particularmente el receptor de andrógeno, tal como el cáncer de próstata. Reivindicación 1: Un compuesto caracterizado porque es de fórmula (1), donde el anillo B es un anillo monocíclico o bicíclico de 4 - 10 miembros que contiene 0 - 4 heteroátomos seleccionados en forma independiente entre N, O ó S; el anillo A es cualquiera de los grupos de fórmulas (2), (3), (4) y (5); L se encuentra ausente, es -CH₂-, -CH₂-CH₂- o -CH₂-CH₂-CH₂-, o en caso de que el anillo A sea el resto de fórmula (2), L también puede ser -C(O)-CH₂-; R¹ es hidrógeno, C₁₋₇ alquilo, C₁₋₇ alcoxi, halógeno, ciano, nitro, halo-C₁₋₇ alquilo, halo-C₁₋₇ alcoxi o C₁₋₇ alquiltio; R² es hidrógeno, C₁₋₇ alquilo, halógeno, hidroxi, halo-C₁₋₇ alquilo, nitro, halo-C₁₋₇ alcoxi o tiol; o R¹ y R² junto con los átomos de carbono a los cuales se encuentran unidos forman un anillo 1,3 fioxol fusionado; R³ es hidrógeno, halógeno, nitro, ciano, oxo, C₁₋₇ alquilo, C₂₋₇ alquenilo, C₃₋₇ cicloalquilo, hidroxi-C₃₋₇ cicloalquilo, C₁₋₇ alcoxi, hidroxi-C₁₋₇ alquilo, halo-C₁₋₇ alquilo, ciano-C₁₋₇ alquilo, C₁₋₇ alcoxi-C₁₋₇ alquilo, C₁₋₇ alquiltio, aminocarbonilo-C₂₋₇ alquenilo, halo-C₁₋₇ alquiltio, C₁₋₇ alcoxicarbonilo-C₁₋₇ alquilo, C₁₋₇ alcoxicarbonilo-C₂₋₇ alquenilo, =NSO₂R²⁰, -S(O)-C₁₋₇ alquilo, -S(O)(NR¹⁴)(R²²), -S(NR¹⁵)(C₁₋₇ alquilo), -C(S)NR¹⁸R¹⁹, -D-C(O)-NR⁶R⁷, -C(O)R⁸, -D-NR⁹R¹⁰, -SO₂R¹¹, carbociclilo de 3 - 10 miembros opcionalmente sustituido, C₁₋₇ alquilo-carbociclilo de 3 - 10 miembros opcionalmente sustituido, heterociclilo de 4 - 10 miembros opcionalmente sustituido o C₁₋₇ alquilo-heterociclilo de 4 - 10 miembros opcionalmente sustituido; R⁴ es hidrógeno, halógeno, hidroxi, C₁₋₇ alquilo, halo-C₁₋₇ alquilo u oxo; R⁵ es hidrógeno, halógeno o C₁₋₇ alquilo; R⁶ es hidrógeno, C₁₋₇ alquilo, C₂₋₇ alquenilo, C₃₋₇ cicloalquilo, hidroxi-C₁₋₇ alquilo, ciano-C₁₋₇ alquilo, -C₁₋₇ alquil-O-C(O)-C₁₋₇ alquilo o heterociclilo de 4 - 10 miembros opcionalmente sustituido; R⁸ es hidrógeno, C₁₋₇ alquilo, C₂₋₇ alquenilo, C₃₋₇ cicloalquilo, C₁₋₇ alcoxi, halo-C₁₋₇ alquilo, C₁₋₇ alcoxi-C₁₋₇ alquilo, C₁₋₇ alquilcarbonilo, C₁₋₇ alcoxicarbonilo, -C₁₋₇ alquil-O-C(O)-C₁₋₇ alquilo, -C₁₋₇ alquil-SO₂(C₁₋₇ alquilo), -N=S(O)(C₁₋₇ alquil)(C₁₋₇ alquilo) o heterociclilo de 4 - 10 miembros opcionalmente sustituido; R⁹ es hidrógeno, C₁₋₇ alquilo, C₃₋₇ cicloalquilo, C₁₋₇ alquilcarbonilo, -SO₂(C₁₋₇ alquilo) o -SO₂(C₃₋₇ cicloalquilo); R¹¹ es C₁₋₇ alquilo, C₂₋₇ alquenilo, C₃₋₇ cicloalquilo, halo-C₁₋₇ alquilo, ciano-C₁₋₇ alquilo, C₁₋₇ alcoxi-C₁₋₇ alquilo, -NR¹²R¹³, carbociclilo de 3 - 10 miembros opcionalmente sustituido o heterociclilo de 4 - 10 miembros opcionalmente sustituido; R¹² es hidrógeno, C₁₋₇ alquilo, hidroxi-C₁₋₇ alquilo, ciano-C₁₋₇ alquilo, C₁₋₇ alcoxi, C₁₋₇ alcoxi-C₁₋₇ alquilo o C₁₋₇ alquilcarbonilo; R⁷, R¹⁰, R¹³, R¹⁸, y R¹⁹ son, en forma independiente, hidrógeno, C₁₋₇ alquilo o C₃₋₇ cicloalquilo; R¹⁴ es hidrógeno, C₁₋₇ alquilo, C₁₋₇ alquilcarbonilo o -SO₂R²¹; R¹⁵ es hidrógeno, C₁₋₇ alquilo, C₃₋₇ cicloalquilo, C₁₋₇ alquilcarbonilo, -SO₂R¹⁷; R¹⁷ es C₁₋₇ alquilo o un carbociclilo de 3 - 10 miembros opcionalmente sustituido; R²⁰ y R²¹ son, en forma independiente, C₁₋₇ alquilo, C₃₋₇ cicloalquilo o carbociclilo de 3 - 10 miembros opcionalmente sustituido; R²² es C₁₋₇ alquilo o C₃₋₇ cicloalquilo; R²³ es hidrógeno u oxo; R²⁴ es hidrógeno o C₁₋₇ alquilo; D se encuentra ausente, es C₁₋₇ alquilo o C₂₋₇ alquenilo; donde el sustituyente opcional en cada caso se selecciona entre 1 - 3 sustituyentes seleccionados en forma independiente entre C₁₋₇ alquilo, halógeno, hidroxi, C₁₋₇ alcoxi, C₁₋₇ alcoxi-C₁₋₇ alquilo, C₁₋₇ alcoxicarbonilo u oxo; y donde el grupo heterociclilo en cada caso tiene 1 - 4 heteroátomos seleccionados en forma independiente entre N, O y S; o una sal aceptable farmacéuticamente del mismo; con la condición de que el compuesto no sea 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[(2,5-dimetilfenil)metoxi]-4H-piran-4-ona; 5-[(2,4-diclorofenil)metoxi]-2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-4H-piran-4-ona; 5-[(3-clorofenil)metoxi]-2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[(4-metilfenil)metoxi]-4H-piran-4-ona; 5-[(3,4-diclorofenil)metoxi]-2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[(3-fluorofenil)metoxi]-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-(1-naftalenilmetoxi)-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[[3-(trifluorometil)fenil]metoxi]-4H-piran-4-ona; 5-[(2-clorofenil)metoxi]-2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-4H-piran-4-ona; 5-[(2-cloro-6-fluorofenil)metoxi]-2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-4H-piran-4-ona; 5-[(4-clorofenil)metoxi]-2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-4H-piran-4-ona; 5-[(4-bromofenil)metoxi]-2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[(2-fluorofenil)metoxi]-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[(2-metilfenil)metoxi]-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-(fenilmetoxi)-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[[4-(trifluorometil)fenil]metoxi]-4H-piran-4-ona; 4-(((6-((3,4-dihidroisoquinolin-2(1H)-il)metil)-4-oxo-4H-piran-3-il)oxi)metil)benzoato de metilo; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[(4-fluorofenil)metoxi]-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[(3,5-dimetoxifenil)metoxi]-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[(3-nitrofenil)metoxi]-4H-piran-4-ona; 5-(((6-((3,4-dihidroisoquinolin-2(1H)-il)metil)-4-oxo-4H-piran-3-il)oxi)metil)furan-2-carboxilato de metilo; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-(2-feniletoxi)-4H-piran-4-ona; 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[(3-metilfenil)metoxi]-4H-piran-4-ona; o 2-[(3,4-dihidro-2(1H)-isoquinolinil)metil]-5-[(4-nitrofenil)metoxi]-4H-piran-4-ona.
ARP170103609A 2016-12-22 2017-12-20 Inhibidores de la cyp11a1 AR110412A1 (es)

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Publication number Priority date Publication date Assignee Title
AR110412A1 (es) * 2016-12-22 2019-03-27 Orion Corp Inhibidores de la cyp11a1
JP2023525137A (ja) 2020-05-14 2023-06-14 オリオン コーポレーション Ｃｙｐ１１ａ１阻害剤
CA3200556A1 (en) 2020-12-01 2021-11-30 David Din Belle 2,3-dihydro-4h-benzo[b][1,4]oxazin-4-yl)(5-(phenyl)-pyridin-3-yl)methanone derivatives and similar compounds as cyp11a1 inhibitors for the treatment of prostate cancer
AR124985A1 (es) 2021-03-01 2023-05-24 Orion Corp Nuevas formas de sal de un inhibidor de cyp11a1 estructurado en 4h-piran-4-ona
EP4301732A1 (en) 2021-03-01 2024-01-10 Orion Corporation Process for the preparation of a cyp11a1 inhibitor and intermediates thereof
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