AR089701A1 - ARILAMIDE DERIVATIVES THAT HAVE ANTIANDROGENIC PROPERTIES - Google Patents

ARILAMIDE DERIVATIVES THAT HAVE ANTIANDROGENIC PROPERTIES

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Publication number
AR089701A1
AR089701A1 ARP130100089A ARP130100089A AR089701A1 AR 089701 A1 AR089701 A1 AR 089701A1 AR P130100089 A ARP130100089 A AR P130100089A AR P130100089 A ARP130100089 A AR P130100089A AR 089701 A1 AR089701 A1 AR 089701A1
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AR
Argentina
Prior art keywords
ring
alkyl
group
substituted
alkoxy
Prior art date
Application number
ARP130100089A
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Spanish (es)
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Medeia Therapeutics Ltd
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Publication date
Application filed by Medeia Therapeutics Ltd filed Critical Medeia Therapeutics Ltd
Publication of AR089701A1 publication Critical patent/AR089701A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • C07C255/49Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/60Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/08Drugs for disorders of the urinary system of the prostate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/44Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/61Halogen atoms or nitro radicals

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Compuestos con efectos anticancerígenos. Reivindicación 1: Un derivado de arilamida que tiene la fórmula (1) o un estereoisómero o sal farmacéuticamente aceptable del mismo; en donde A se selecciona del grupo que consta de H, halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, perhaloalquilo C₁₋₂, hidroxihaloalquilo C₁₋₆, aminoalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, perhaloalcoxi C₁₋₂, alcoxi C₁₋₂-alquenilo C₁₋₆, alquilsulfonilo C₁₋₆, arilsulfonilo, y NHR, en donde R es H o alquilo C₁₋₆; arilamida, alquilamida C₁₋₆, arilsulfonamida, alquilsulfonamida C₁₋₆, y arilo; R y R cada uno de modo independiente se selecciona del grupo que consta de H y alquilo C₁₋₆; z es un número entero de 0 a 3; RA es un sistema de anillo mono o bicíclico, aromático o heteroaromático que tiene 6 a 10 átomos en el anillo, por lo cual dicho sistema de anillo mono o bicíclico comprende 0 a 2 ó 0 a 4 átomos nitrógeno en el anillo, respectivamente, y los otros átomos en el anillo son átomos de carbono, dicho sistema de anillo no está sustituido o está sustituido una o más veces, y donde dichos sustituyentes pueden estar localizados en cualquier ubicación apropiada y están representados por RA; cada RA se selecciona de modo independiente del grupo que consta de halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, perhaloalquilo C₁₋₂, hidroxi, alcoxi C₁₋₆, NO₂, CN, C(O)R, COOR, CONHR, NR₂, NHCOR, NHCOCF₃, NHCONHR, NHCOOR, OCONHR, donde cada R es de modo independiente hidrógeno o alquilo C₁₋₆, y (CH₂)ₙCHO, donde n es un número entero de 0 - 6; o cuando RA es un anillo monocíclico, dos RA adyacentes pueden estar unidos conjuntamente para formar un puente sustituido o no sustituido; RB es un sistema de anillo aromático o heteroaromático que tiene 6 átomos en el anillo que comprende 0 a 2 átomos de nitrógeno en el anillo, mientras que los otros átomos en el anillo son átomos de carbono, dicho sistema de anillo está sustituido una o más veces, y donde dichos sustituyentes pueden estar localizados en cualquier ubicación apropiada y están representados por RB; cada RB se selecciona de modo independiente del grupo que consta de halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, perhaloalquilo C₁₋₂, hidroxi, alcoxi C₁₋₆, NO₂, CN, C(O)R, COOR, CONHR, NR₂, NHCOR, NHCOCF₃, NHCONHR, NHCOOR, OCONHR, SR, S(O)R, SO₂R, y NHCSCH₃, donde R es tal como se definió anteriormente; o dos RB adyacentes pueden formar con los átomos de carbono, a los cuales están unidos, un anillo sustituido o no sustituido alifático o heteroalifático, aromático o heteroaromático; X se selecciona del grupo que consta de O, S, S(O), SO₂, y NR, donde R se selecciona del grupo que consta de H, alquilo C₁₋₆, y COR, donde R es tal como se definió anteriormente; o cuando z es 0, luego X puede ser N y formar junto con RC un anillo heterocíclico seleccionado del grupo que consta de morfolina, 1,2,4-triazol, imidazol y imidazol N-sustituido; y RC, cuando no forma un anillo con X tal como se definió anteriormente, se selecciona del grupo que consta de H, alquilo C₁₋₆, alquenilo C₂₋₆, cicloalquilo C₃₋₄, haloalquilo C₁₋₆, perhaloalquilo C₁₋₂, haloalquenilo C₂₋₆, CN-alquilo C₁₋₆, alcoxi C₁₋₆, y un arilo, heteroarilo, anillo alifático o heteroalifático, de 5 - 7 miembros, sistemas de anillos que están opcionalmente sustituidos con uno o más sustituyentes, y donde dichos sustituyentes pueden estar situados en cualquier ubicación adecuada y representados por RC, cada RC se selecciona de modo independiente del grupo que consta de halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, perhaloalquilo C₁₋₂, hidroxi, alcoxi C₁₋₆, NO₂, CN, C(O)R, COOR, CONHR, NR₂, NHCOR, NHCOCF₃, NHCONHR, NHCOOR, OCONHR, NHSO₂R, SR, S(O)R, SO₂R, y NHCSCH₃, donde R es tal como se definió anteriormente.Compounds with anticancer effects. Claim 1: An arylamide derivative having the formula (1) or a stereoisomer or pharmaceutically acceptable salt thereof; wherein A is selected from the group consisting of H, halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₂ perhaloalkyl, C₁₋₆ hydroxyhaloalkyl, C₁₋₆ aminoalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, perhaloalkoxy C₁₋₂, C₁₋₂-Cque-alkenyl alkoxy, C₁₋₆ alkylsulfonyl, arylsulfonyl, and NHR, wherein R is H or C₁₋₆ alkyl; arylamide, C₁₋₆ alkylamide, arylsulfonamide, C₁₋₆ alkylsulfonamide, and aryl; R and R each independently is selected from the group consisting of H and C₁₋₆ alkyl; z is an integer from 0 to 3; RA is a mono or bicyclic, aromatic or heteroaromatic ring system having 6 to 10 ring atoms, whereby said mono or bicyclic ring system comprises 0 to 2 or 0 to 4 nitrogen atoms in the ring, respectively, and the other atoms in the ring are carbon atoms, said ring system is not substituted or substituted one or more times, and where said substituents can be located at any appropriate location and are represented by RA; each RA is independently selected from the group consisting of halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₂ perhaloalkyl, hydroxy, C₁₋₆ alkoxy, NO₂, CN, C (O) R, COOR, CONHR, NR₂, NHCOR, NHCOCF₃, NHCONHR, NHCOOR, OCONHR, where each R is independently hydrogen or C₁₋₆ alkyl, and (CH₂) ₙCHO, where n is an integer from 0-6; or when RA is a monocyclic ring, two adjacent RAs can be joined together to form a substituted or unsubstituted bridge; RB is an aromatic or heteroaromatic ring system having 6 atoms in the ring comprising 0 to 2 nitrogen atoms in the ring, while the other atoms in the ring are carbon atoms, said ring system is substituted one or more times, and where said substituents may be located at any appropriate location and are represented by RB; each RB is independently selected from the group consisting of halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₂ perhaloalkyl, hydroxy, C₁₋₆ alkoxy, NO₂, CN, C (O) R, COOR, CONHR, NR₂, NHCOR, NHCOCF₃, NHCONHR, NHCOOR, OCONHR, SR, S (O) R, SO₂R, and NHCSCH₃, where R is as defined above; or two adjacent RBs can form with the carbon atoms, to which they are attached, an aliphatic or heteroaliphatic, aromatic or heteroaromatic substituted or unsubstituted ring; X is selected from the group consisting of O, S, S (O), SO₂, and NR, where R is selected from the group consisting of H, C₁₋₆ alkyl, and COR, where R is as defined above; or when z is 0, then X can be N and together with RC form a heterocyclic ring selected from the group consisting of morpholine, 1,2,4-triazole, imidazole and N-substituted imidazole; and RC, when it does not form a ring with X as defined above, is selected from the group consisting of H, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₃₋₄ cycloalkyl, C₁₋₆ haloalkyl, C₁₋₂ perhaloalkyl, C₂₋₆ haloalkenyl, CN-C₁₋₆ alkyl, C₁₋₆ alkoxy, and a 5-7 membered aliphatic or heteroaliphatic ring, ring systems that are optionally substituted with one or more substituents, and wherein said Substituents may be located at any suitable location and represented by RC, each RC is independently selected from the group consisting of halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₂ perhaloalkyl, hydroxy, C₁₋₆ alkoxy, NO₂ , CN, C (O) R, COOR, CONHR, NR₂, NHCOR, NHCOCF₃, NHCONHR, NHCOOR, OCONHR, NHSO₂R, SR, S (O) R, SO₂R, and NHCSCH₃, where R is as defined above.

ARP130100089A 2012-01-13 2013-01-11 ARILAMIDE DERIVATIVES THAT HAVE ANTIANDROGENIC PROPERTIES AR089701A1 (en)

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WO2023011596A1 (en) * 2021-08-05 2023-02-09 中国药科大学 Amide compound and use thereof

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU88769I2 (en) 1982-07-23 1996-11-05 Zeneca Ltd Bicalutamide and its pharmaceutically acceptable salts and esters (Casodex (R))
TW200306819A (en) * 2002-01-25 2003-12-01 Vertex Pharma Indazole compounds useful as protein kinase inhibitors
US7625923B2 (en) 2004-03-04 2009-12-01 Bristol-Myers Squibb Company Bicyclic modulators of androgen receptor function
TW200812962A (en) 2006-07-12 2008-03-16 Astrazeneca Ab New compounds I/418
US20090156614A1 (en) 2006-07-19 2009-06-18 Dalton James T Selective androgen receptor modulators, analogs and derivatives thereof and uses thereof
US8450344B2 (en) * 2008-07-25 2013-05-28 Aerie Pharmaceuticals, Inc. Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds
ITBO20090078A1 (en) 2009-02-13 2010-08-14 Consiglio Nazionale Ricerche COMPOUNDS FOR TREATING TUMOR TO THE PROSTATE AND PROCEDURES FOR THEIR SYNTHESIS
EP2424853B1 (en) 2009-04-10 2018-09-19 Istituto Scientifico Romagnolo Per Lo Studio E La Cura Dei Tumori (I.R.S.T.) S.R.L. Non-steroidal compounds for androgen receptor modulation, processes for the preparation and uses thereof
ES2834451T3 (en) * 2009-05-01 2021-06-17 Aerie Pharmaceuticals Inc Dual Mechanism Inhibitors for Treating Diseases

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