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AR108905A1 - Compuestos de indol sustituidos con [1,2,4]triazolo[1,5-a]piridinilo - Google Patents

Compuestos de indol sustituidos con [1,2,4]triazolo[1,5-a]piridinilo

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AR108905A1
AR108905A1 ARP170101788A ARP170101788A AR108905A1 AR 108905 A1 AR108905 A1 AR 108905A1 AR P170101788 A ARP170101788 A AR P170101788A AR P170101788 A ARP170101788 A AR P170101788A AR 108905 A1 AR108905 A1 AR 108905A1
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Argentina
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crxrx
alkyl
fluoroalkyl
hydroxyalkyl
nrx
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ARP170101788A
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Anupama Ramachandra
Subramaya HEDGE
Ramesh Kumar Sistla
Shoshana L Posy
Trevor C Sherwood
Kumar Sreekantha Ratna
Laxman Pasunoori
Christopher P Mussari
John E Macor
Louis J Lombardo
Tasir Shamsul Haque
Dharmpal S Dodd
Alaric J Dyckman
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Bristol Myers Squibb Co
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • 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
    • A61K31/4196—1,2,4-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
    • A61K31/435—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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • 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
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
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    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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
    • C07D471/04—Ortho-condensed systems

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  • Health & Medical Sciences (AREA)
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  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Reivindicación 1: Un compuesto caracterizado por la fórmula (1) o una sal de este, en donde: R¹ es H, Cl, -CN, C₁₋₄ alquilo, C₁₋₃ fluoroalquilo, C₁₋₃ hidroxi-fluoroalquilo, -CRᶻ=CH₂, C₃₋₆ cicloalquilo, -CH₂(C₃₋₆ cicloalquilo), -C(O)O(C₁₋₃ alquilo) o tetrahidropiranilo; cada R² es independientemente halo, -CN, -OH, -NO₂⁺, C₁₋₃ alquilo, C₁₋₂ fluoroalquilo, C₁₋₂ cianoalquilo, C₁₋₃ hidroxialquilo, C₁₋₃ aminoalquilo, -O(CH₂)₁₋₂OH, -(CH₂)₀₋₄O(C₁₋₄ alquilo), C₁₋₃ fluoroalcoxi, -(CH₂)₁₋₄O(C₁₋₃ alquilo), -O(CH₂)₁₋₂OC(O)(C₁₋₃ alquilo), -O(CH₂)₁₋₂NRˣRˣ, -C(O)O(C₁₋₃ alquilo), -C(O)NRʸRʸ, -NRʸRʸ, -NRʸ(C₁₋₃ fluoroalquilo), -NRʸ(C₁₋₄ hidroxialquilo), -NRˣCH₂(fenilo), -NRˣS(O)₂(C₃₋₆ cicloalquilo), -NRXC(O)(C₁₋₃ alquilo), -NRX(CH₂-ciclopropilo), C₃₋₆ cicloalquilo, morfolinilo, dioxotiomorfolinilo, metilpiperidinilo, metilpiperazinilo, amino-oxadiazolilo, imidazolilo, triazolilo o -C(O)(tiazolilo); R³ es: (a) -L¹-A; o (b) H, C₁₋₆ alquilo, C₁₋₃ fluoroalquilo, C₁₋₃ cianoalquilo, C₁₋₆ hidroxialquilo, C₁₋₃ hidroxi-fluoroalquilo, -CRˣRˣCRˣ(OH)CRˣ=CRˣRˣ, -C=N(NRˣRˣ), -(CRˣRˣ)₁₋₄O(C₁₋₃ alquilo), -(CRˣRˣ)₁₋₄O(CRˣRˣ)₁₋₃O(C₁₋₃ alquilo), -CH₂CH(OH)CH₂O(C₁₋₃ alquilo), -(CRˣRˣ)₁₋₃S(C₁₋₃ alquilo), -(CH₂)₁₋₃C₍O₎OC₍CH₃)₃, -(CRˣRˣ)₀₋₃NRˣRʸ, -(CRˣRˣ)₀₋₃NRˣ(C₁₋₄ hidroxialquilo), -CH₂CH(OH)CH₂NRˣRʸ, -C(O)H, -C(O)(C₁₋₆ alquilo), -C(O)(C₁₋₄ hidroxialquilo), -C(O)(C₁₋₃ fluoroalquilo), -C(O)(C₁₋₃ cloroalquilo), -C(O)(C₁₋₃ cianoalquilo), -(CRˣRˣ)₀₋₃C₍O₎OH, ₋C₍O₎₍CH₂)₀₋₂O(C₁₋₄ alquilo), -C(O)(CRˣRˣ)₀₋₂O(CRˣRˣ)₁₋₂O(C₁₋₃ alquilo), -C(O)(CRˣRˣ)₀₋₂O(CRˣRˣ)₁₋₂NRʸRʸ, -C(O)CRˣRˣS(O)₂(C₁₋₃ alquilo), -C(O)CRˣRˣNRˣS(O)₂(C₁₋₃ alquilo), -C(O)CRˣRˣOC(O)(C₁₋₃ alquilo), -C(O)(CRˣRˣ)₀₋₃NRʸRʸ, -C(O)(CRˣRˣ)₀₋₁NRˣ(C₁₋₃ cianoalquilo), -C(O)(CRˣRˣ)₀₋₂NRʸ(C₁₋₆ hidroxialquilo), -C(O)(CRˣRˣ)₀₋₂NRˣ(C₁₋₃ fluoroalquilo), -C(O)(CRˣRˣ)₀₋₁NRˣ(C₁₋₅ hidroxi-fluoroalquilo), -C(O)(CRˣRˣ)₀₋₁NRˣ(CH₂)₁₋₂O(C₁₋₃ hidroxialquilo), -C(O)(CRˣRˣ)₀₋₂NRˣ(CH₂)₁₋₂NRˣC(O)(C₁₋₂ alquilo), -C(O)(CRˣRˣ)₀₋₂NRˣ((CRˣRˣ)₁₋₂O(C₁₋₂ alquilo)), -C(O)(CRˣRˣ)₀₋₂N((CRˣRˣ)₁₋₂O(C₁₋₂ alquilo))₂, -C(O)(CRˣRˣ)₀₋₂NRˣ(CRˣRˣ)₁₋₃NRˣRˣ, -C(O)CRˣ(NH₂)(CRˣRˣ)₁₋₄NRˣRˣ, -C(O)CRˣ(NH₂)(CRˣRˣ)₁₋₄NRˣC(O)NRˣRˣ, -C(O)(CRˣRˣ)₀₋₃NRˣ(CH₂)₀₋₁C₍O₎₍C₁₋₃ alquilo), -C(O)(CRˣRˣ)₀₋₃N((CH₂)₀₋₁C₍O₎₍C₁₋₃ alquilo))₂, -C(O)(CRˣRˣ)₀₋₁NRˣ(CH₂)₀₋₁C₍O₎₍C₁₋₃ cianoalquilo), -C(O)(CRˣRˣ)₀₋₂NRˣ(CH₂)₁₋₂C₍O₎NRʸRʸ -C(O)(CRˣRˣ)₁₋₃C₍O₎NRʸRʸ, -C(O)(CRˣRˣ)₁₋₃S(O)₂NRʸRʸ, -C(O)(CRˣRˣ)₀₋₂NRˣ(CHRʸ(CH₂OH)), -(CRˣRˣ)₁₋₂C₍O₎NRʸRʸ, -CH(CN)C(O)NRʸRʸ, -(CRˣRˣ)₁₋₂C₍O₎NRʸ(C₁₋₃ fluoroalquilo), -(CRˣRˣ)₁₋₂C₍O₎NRʸ(C₁₋₄ hidroxialquilo), -(CRˣRˣ)₁₋₂C₍O₎NRʸ(C₁₋₃ cianoalquilo), -(CRˣRˣ)₁₋₂C₍O₎NRˣ(CH₂)₁₋₂O(C₁₋₃ alquilo), -(CRˣRˣ)₁₋₂C₍O₎NRˣCH(C₁₋₄ alquilo)(C₁₋₃ hidroxialquilo), -(CRˣRˣ)₁₋₂C₍O₎NRˣCH(C₁₋₃ hidroxialquilo)(C₃₋₆ cicloalquilo), -(CH₂)₁₋₂C₍O₎NRˣ(CH₂)₁₋₂C₍O₎NRˣRˣ, -(CH₂)₁₋₂C₍O₎NRˣ(CH₂)₁₋₂S(C₁₋₃ alquilo), -(CH₂)₁₋₂C₍O₎NRˣ(CH₂)₁₋₂S(O)₂OH, -(CH₂)₁₋₂C₍O₎NRˣ(CH₂)₁₋₂NRˣC(O)(C₁₋₃ alquilo), -(CH₂)₁₋₂C₍O₎NRˣ(CH₂)₁₋₃NRˣRˣ, -(CH₂)₁₋₂C₍O₎N₍CH₂CH₃)(CH₂)₁₋₃NRˣRˣ, -(CRˣRˣ)₀₋₃S(O)₂(C₁₋₄ alquilo), -(CH₂)₀₋₂S(O)₂(C₁₋₃ fluoroalquilo), -(CRˣRˣ)₀₋₂S(O)₂NRʸRʸ, -(CRˣRˣ)₀₋₂NRˣS(O)₂(C₁₋₃ alquilo), -C(O)C(O)OH, -C(O)C(O)NRʸRʸ o -C(O)C(O)NRʸ(CRˣRˣ)₁₋₂NRʸRʸ; L¹ es un enlace, -(CRˣRˣ)₁₋₂-, -(CRˣRˣ)₁₋₂CRˣ(OH)-, -(CRˣRˣ)₁₋₂O-, -CRˣRˣC(O)-, -(CRˣRˣ)₂NRˣ(CRˣRˣ)₀₋₁-, -CRˣRˣC(O)NRˣ(CRˣRˣ)₀₋₄-, -C(O)(CRˣRˣ)₀₋₃-, -C(O)(CRˣRˣ)₀₋₂NRˣ(CRˣRˣ)₀₋₂-, -C(O)(CRˣRˣ)₀₋₂N(C₁₋₂ hidroxialquilo)(CRˣRˣ)₀₋₂-, -C(O)(CRˣRˣ)₀₋₂NRˣ(CRˣRˣ)₁₋₂CRˣ(OH)-, -C(O)(CRˣRˣ)₁₋₂C₍O₎NRˣ-, -(CRˣRˣ)₀₋₂C₍O₎NRˣ(CRˣRˣ)₁₋₂CRˣ(OH)-, -(CRˣRˣ)₀₋₂C₍O₎N₍C₁₋₂ hidroxialquilo)(CRˣRˣ)₁₋₂-, -C(O)(CRˣRˣ)₀₋₁O-, -C(O)(CRˣRˣ)₁₋₂NHS(O)₂-, -C(O)CRˣ(NH₂)CRˣRˣ-, -C(O)C(O)(CRˣRˣ)₀₋₂-, -C(O)NRˣ(CRˣRˣ)₁₋₂- o -S(O)₂-; A es 2-oxa-6-azaspiro[3,3]heptanilo, 4-oxaspiro[2.5]octanilo, 7-azaspiro[3.5]nonanilo, 8-azabiciclo[3.2.1]octanilo, 8-oxa-3-azabiciclo[3.2.1]octanilo, 9-azabiciclo[3.3.1]nonanilo, adamantanilo, azepanilo, azetidinilo, C₃₋₆ cicloalquilo, diazepanilo, dihidroinonilo, dihidropirimidinonilo, dioxanilo, dioxidotiadiazinanilo, dioxidotiazolidinilo, dioxidotiomorfolinilo, dioxoisotiazolidinilo, dioxidotiazinanilo, dioxotetrahidrotiofenilo, dioxotetrahidrotiopiranilo, dioxotiomorfolinilo, furanilo, imidazolilo, imidazolidinonilo, indolilo, isoquinolinilo, isoxazolilo, morfolinilo, morflinonilo, naftalenilo, octahidrociclopenta[b]piranilo, octahidropirrolo[3,4-b]piridinilo, oxazolidinonilo, oxadiazolilo, oxazolilo, oxetanilo, fenilo, piperidinilo, piperidinonilo, piperazinilo, piperazinonilo, pirazinilo, pirazolilo, piridazinilo, piridazinonilo, piridinonilo, piridinilo, pirimidinilo, pirrolidinonilo, pirrolidinilo, pirrolilo, quinolinilo, quinolizinonilo, tetrahidrofuranilo, tetrahidropiranilo, tetrahidrotiopiranilo, tetrazolilo, tiadiazolilo, tiazolilo, triazolonilo o triazolilo, cada uno sustituido con -L²-Rᵃ y 0 a 4 Rᵇ; L² es un enlace o -CRˣRˣ-; Rᵃ es: (a) H, F, Cl, -CN, -OH, C₁₋₆ alquilo, C₁₋₃ fluoroalquilo, C₁₋₅ hidroxialquilo, -(CH₂)₀₋₄O(C₁₋₃ alquilo), -(CRˣRˣ)₁₋₃S(C₁₋₃ alquilo), -(CRˣRˣ)₁₋₃NHC(O)O(C₁₋₄ alquilo), -(CRˣRˣ)₁₋₃NRʸRʸ, -(CRˣRˣ)₁₋₃C₍O₎NRʸRʸ, -O(C₁₋₃ fluoroalquilo), -S(O)₂NRˣRˣ, -O(CRˣRˣ)₁₋₃NRˣRˣ, -NHS(O)₂(C₁₋₃ alquilo), -NRˣRˣ, -NRˣ(C₁₋₄ alquilo), -NRˣC(O)(C₁₋₄ alquilo), -(CRˣRˣ)₀₋₃C₍O₎OH, ₋C₍O₎₍C₁₋₅ alquilo), -C(O)(C₁₋₃ fluoroalquilo), -C(O)O(C₁₋₄ alquilo), -C(O)NH(C₁₋₃ cianoalquilo), -C(O)NRʸRʸ, -C(O)NRˣCH₂C(O)NRˣRˣ o -C(O)NRˣCH₂CH₂NHC(O)(C₁₋₃ alquilo); (b) C₃₋₆ cicloalquilo o -C(O)NH(C₃₋₆ cicloalquilo), en donde cada cicloalquilo se sustituye con 0 a 2 sustituyentes seleccionados independientemente de -OH, C₁₋₃ alquilo, C₁₋₃ hidroxialquilo, C₁₋₃ fluoroalquilo y -C(O)O(C₁₋₃ alquilo); o (c) A¹, -CH₂A¹, -C(O)A¹, -NRˣA¹ o -C(O)NRˣA¹, en donde A¹ es furanilo, imidazolilo, indolilo, isoxazolilo, morfolinilo, octahidropirrolo[3,4-c]pirrolilo, oxazolilo, oxetanilo, fenilo, piperazinilo, piperidinilo, pirazolilo, piridinilo, pirimidinilo, pirrolidinilo, pirrolilo, tetrahidrofuranilo, tetrahidropiranilo, tiadiazolilo, tiazolilo, tiofenilo o triazolilo, cada uno sustituido con 0 a 3 sustituyentes seleccionados independientemente de -OH, C₁₋₃ alquilo, C₁₋₃ hidroxialquilo, -C(O)(C₁₋₂ alquilo), -C(O)O(C₁₋₃ alquilo), -NRˣRˣ, fenilo, trifluorometil-fenilo, -CH₂(bromofenilo) y -CH₂CH₂(pirrolidinilo); cada Rᵇ es independientemente F, -OH, -CH₃, -CF₃ o OCH₃; cada Rˣ es independientemente H o -CH₃; cada Rʸ es independientemente H o C₁₋₆ alquilo; Rᶻ es H, C₁₋₂ alquilo o C₁₋₂ fluoroalquilo; cada R⁴ es independientemente F, -OH, C₁₋₂ alquilo o -OCH₃; o dos R⁴ unidos al mismo átomo de carbono forman =O; o en donde, cuando m es al menos 2, dos R⁴, cada uno unido a un átomo de carbono diferente adyacente al átomo de nitrógeno en el anillo de piperidinilo, pueden formar un puente -CH₂CH₂-; cada R⁵ es independientemente F, Cl, -CN, C₁₋₂ alquilo, C₁₋₂ fluoroalquilo o -OCH₃; m es 0, 1, 2, 3 ó 4; n es 0, 1 ó 2; y p es 0, 1, 2, 3 ó 4.
ARP170101788A 2016-06-29 2017-06-28 Compuestos de indol sustituidos con [1,2,4]triazolo[1,5-a]piridinilo AR108905A1 (es)

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