AR117576A1 - Derivados de sulfinilaminobenzamida y sulfonilaminobenzamida - Google Patents

Derivados de sulfinilaminobenzamida y sulfonilaminobenzamida

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Publication number
AR117576A1
AR117576A1 ARP190101345A ARP190101345A AR117576A1 AR 117576 A1 AR117576 A1 AR 117576A1 AR P190101345 A ARP190101345 A AR P190101345A AR P190101345 A ARP190101345 A AR P190101345A AR 117576 A1 AR117576 A1 AR 117576A1
Authority
AR
Argentina
Prior art keywords
membered
nr13r13
heterocyclyl
cycloalkyl
heteroalkyl
Prior art date
Application number
ARP190101345A
Other languages
English (en)
Inventor
David Sperandio
Michael Sangi
Casey Lockwood Olen
Gregory Notte
Joshua A Kaplan
Julie Farand
Original Assignee
Gilead Sciences Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc
Publication of AR117576A1 publication Critical patent/AR117576A1/es

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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
    • C07C311/46—Y being a hydrogen or a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, 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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—Thiols, 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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25—Thiols, 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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/382—Heterocyclic compounds having sulfur as a ring hetero atom having six-membered rings, e.g. thioxanthenes
    • 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
    • A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/541—Non-condensed thiazines containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
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    • C07C307/04—Diamides of sulfuric acids
    • C07C307/10—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to carbon atoms of six-membered aromatic rings
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/14—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of rings other than six-membered aromatic rings
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C313/02—Sulfinic acids; Derivatives thereof
    • C07C313/06—Sulfinamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
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    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
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    • C07—ORGANIC CHEMISTRY
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    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
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    • C07C323/10—Thiols, 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 singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, 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 singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/12—Thiols, 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 singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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    • C07C323/23—Thiols, 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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/30—Thiols, 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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
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    • C07C323/31—Thiols, 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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
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    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/60—Heterocyclic 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
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Abstract

Se proporciona un compuesto de fórmula (1), en donde los grupos variables se definen en la presente. Reivindicación 1: Un compuesto de fórmula (1), o una sal farmacéuticamente aceptable, estereoisómero, mezclas de estereoisómeros, tautómeros o análogos deuterados de los mismos, en donde: Q se selecciona del grupo que consiste en -S(O)₂-, -S(O)-, -S(O)(NH)-, -S(O)(NR⁸)-; R¹ se selecciona de un grupo que consiste en: alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, -NR¹³R¹³, arilo de 6 - 10 miembros, heteroarilo de 5 - 10 miembros, cicloalquilo C₃₋₁₂ y heterociclilo de 4 - 12 miembros, en donde cada alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, arilo de 6 - 10 miembros, heteroarilo de 5 - 10 miembros, cicloalquilo C₃₋₁₂ y heterociclilo de 4 - 12 miembros están opcionalmente sustituidos adicionalmente con uno o más grupos R¹¹; R¹¹ se selecciona de un grupo que consiste en: hidroxilo, oxo, halo, -CN, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 a 12 miembros, arilo de 6 a 10 miembros, heteroarilo de 5 a 10 miembros, -P(O)R¹⁴R¹⁴, -S(O)(NH)R¹⁴, -S(O)(NR⁸)R¹⁴, -S(O)(NH)NR¹³R¹³, -S(O)(NR⁸)NR¹³R¹³, -SH, -S(O)₀₋₂R¹⁴, -S(O)₁₋₂NR¹³R¹³, -SF₅, -NO₂, -NR¹³R¹³, -NR¹³SO₂R¹⁴, -OS(O)₂R¹⁴, -C(O)OR¹⁴, -C(O)R¹⁴, -NR¹³C(O)OR¹⁴, -NR¹³C(O)NR¹³R¹³, -NR¹³S(O)₂NR¹³R¹³, y -C(O)NR¹³R¹³, en donde cada alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros y heteroarilo de 5 - 10 miembros están opcionalmente sustituidos con uno o más grupos R⁹; cada R⁹ se selecciona independientemente del grupo que consiste en: -H, oxo, -OH, -CN, halo, alquilo C₁₋₆, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros, heteroarilo de 5 - 10 miembros, -NR¹³R¹³, -NR¹³C(O)OR¹⁴, -OS(O)₂R¹⁴, -C(O)OR¹⁴, -S(O)(NH)R¹⁴, -S(O)(NR⁸)R¹⁴, -S(O)(NH)NR¹³R¹³, -S(O)(NR⁸)NR¹³R¹³, -S(O)₀₋₂R¹⁴, -S(O)₁₋₂NR¹³R¹³, -C(O)NR¹³R¹³, -NR¹³SO₂R¹⁴, -C(O)R¹⁴, -NR¹³C(O)NR¹³R¹³, -NR¹³S(O)₂NR¹³R¹³, SF₅ y -NO₂, en donde cada uno de alquilo C₁₋₆, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros, y heteroarilo de 5 - 10 miembros están opcionalmente sustituidos con uno o más grupos R¹⁶; cada R¹³ se selecciona independientemente del grupo que consiste en -H, alquilo C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo C₃₋₆, arilo de 6 - 10 miembros, heterociclilo de 4 - 12 miembros y heteroarilo de 5 - 10 miembros, en donde el alquilo C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 6 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros y heteroarilo de 5 - 10 miembros están opcionalmente sustituidos con uno o más grupos R¹⁵; cada R¹⁴ se selecciona independientemente del grupo que consiste en: alquilo C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo C₃₋₆, arilo de 6 - 10 miembros, heterociclilo de 4 - 12 miembros y heteroarilo de 5 - 10 miembros, en donde el alquilo C₁₋₆, el hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 6 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros y heteroarilo de 5 - 10 miembros están opcionalmente sustituidos con uno o más grupos R¹⁵; cada R¹⁵ se selecciona independientemente de -H, halo, -CN, -OH, oxo, -NO₂, -SF₅, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros, heteroarilo de 5 - 10 miembros, -S(O)(NH)R¹⁶, -S(O)(NR⁸)R¹⁶, -S(O)(NH)NR¹⁶R¹⁶, -S(O)(NR⁸)NR¹⁶R¹⁶, -S(O)₀₋₂R¹⁶, -S(O)₂NH₂, -NH₂, -S(O)NR¹⁶R¹⁶, C(O)R¹⁶, -C(O)NR¹⁶R¹⁶ y C(O)OR¹⁶, en donde cicloalquilo de 3 - 6 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros y heteroarilo de 5 - 10 miembros están opcionalmente sustituidos con uno o más grupos R¹⁶; cada R¹⁶ se selecciona independientemente de halo, -CN, -OH, -NH₂, oxo, -NO₂, -SF₅, alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₆, haloalcoxi C₁₋₆, hidroxialquilo C₁₋₆, tiohaloalquilo, sulfonilalquilo, sulfonilhaloalquilo, sulfonilcicloalquilo, cicloalquilo de 3 - 6 miembros, -C(O)NH₂ y -S(O)₂NH₂; R² se selecciona de un grupo que consiste en: -H, -CN, -F, -Cl, alquilo C₁₋₆, haloalquilo C₁₋₃, heteroalquilo C₁₋₃, alcoxi C₁₋₃ y haloalcoxi C₁₋₃; cada R³ y R⁴ se selecciona independientemente de un grupo que consiste en: -H, halo, -OH, -CN, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 - 12 miembros, heteroarilo de 5 - 10 miembros, -SF₅, -S(O)₀₋₂R¹⁴, -S(O)(NH)R¹⁴, -S(O)(NR⁸)R¹⁴, -S(O)(NH)NR¹³R¹³, -S(O)(NR⁸)NR¹³R¹³, -SH, -NR¹³R¹³, -NR¹³SO₂R¹⁴, -NR¹³S(O)₂NR¹³R¹³, -NR¹³C(O)NR¹³R¹³, -NR¹³C(O)OR¹⁴, trialquilsililo C₁₋₄, -C(O)R¹⁴, -C(O)OR¹⁴, -C(O)NR¹³R¹³, y -NO₂, en donde alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros y heteroarilo de 5 - 10 miembros son opcionalmente sustituidos con uno o más grupos R⁹; R⁵ se selecciona de un grupo que consiste en: -H, -CN, -F, -Cl, alquilo C₁₋₃, haloalquilo C₁₋₃, heteroalquilo C₁₋₃, alcoxi C₁₋₃ y haloalcoxi C₁₋₃; en donde R² y R³, o R³ y R⁴, o R⁴ y R⁵ pueden unirse opcionalmente junto con los átomos a los que están unidos, para formar un cicloalquilo de 5 - 6 miembros, un heterociclilo, fenilo de 5 - 6 miembros, o un heteroarilo de 5 - 6 miembros, cada uno de dichos grupos cíclico se fusionan respectivamente con el fenilo al que están unidos, y cada uno está opcionalmente sustituido con uno o más grupos R⁹; R⁶ se selecciona del grupo que consiste en: anillo carbobicíclico de 5 - 10 miembros, anillo tricíclico de 8 - 10 miembros, anillo heterobicíclico de 6 - 12 miembros y anillo policíclico de 8 - 12 miembros, en donde el anillo carbobicíclico de 5 - 10 miembros, el anillo tricíclico de 8 - 10 miembros, el anillo policíclico de 8 - 12 miembros, o el anillo heterobicíclico de 6 - 12 miembros puede ser fusionado, puenteado o espiro, y en el que el anillo carbobicíclico de 5 - 10 miembros, el anillo tricíclico de 8 - 10 miembros, el anillo heterocíclico de 6 - 12 miembros y el anillo policíclico de 8 - 12 miembros están sustituidos con uno o más R⁷; R⁷ se selecciona del grupo que consiste en: -H, halo, -CN, oxo, -OH, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, trialquilsililo C₁₋₄, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, -S(O)₀₋₂R¹⁴, -S(O)(NH)R¹⁴, -S(O)(NR⁸)R¹⁴, -S(O)(NH)NR¹³R¹³, -S(O)(NR⁸)NR¹³R¹³, -SH, -NR¹³R¹³, -P(O)R¹⁴R¹⁴, -C(O)OH, -C(O)OR¹⁴, -C(O)NR¹³R¹³, -S(O)₂NR¹³R¹³, -C(O)R¹⁴, arilo de 6 - 10 miembros, heteroarilo de 5 - 10 miembros, heterociclilo de 4 - 12 miembros; en donde cada uno de dichos heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros, heteroarilo de 5 - 10 miembros, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, trialquilsililo C₁₋₄, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆ y cicloalquilo de 3 - 12 miembros están opcionalmente sustituidos con uno o más R¹⁵; y n es 1, 2 ó 3; R⁸ es alquilo C₁₋₆, -C(O)R¹⁴, cicloalquilo de 3 - 12 miembros, heteroalquilo C₁₋₆, arilo de 6 - 10 miembros, heteroarilo de 5 - 10 miembros, heterociclilo de 4 - 12 miembros, -C(O)OR¹⁴, -C(O)NR¹³R¹³, y -SO₂R¹⁴, en donde cada uno de alquilo C₁₋₆, -C(O)R¹⁴, cicloalquilo de 3 - 12 miembros, heteroalquilo C₁₋₆, arilo de 6 - 10 miembros, heteroarilo de 5 - 10 miembros, heterociclilo de 4 - 12 miembros está opcionalmente sustituido con halo, -CN, oxo, hidroxilo, alquilo C₁₋₆, alcoxi C₁₋₆, -S(O)₁₋₂R¹⁴, -S(O)₂NR¹³R¹³, -NO₂, -SF₅, haloalquilo C₁₋₆, haloalcoxi C₁₋₆, hidroxialquilo C₁₋₆, -NR¹³R¹³, -C(O)OR¹⁴, heteroalquilo C₁₋₆, cicloalquilo de 3 - 6 miembros opcionalmente sustituido con uno o más R¹⁶, heterociclilo de 4 - 12 miembros opcionalmente sustituido con uno o más R¹⁶, arilo de 6 - 10 miembros opcionalmente sustituido con uno o más R¹⁶, heteroarilo de 5 - 10 miembros opcionalmente sustituido con uno o más R¹⁶; sujeto a las condiciones que (i) cuando R⁶ es un anillo carbocíclico C₈₋₁₂, y tanto R³ como R⁷ son H, entonces R⁴ se selecciona del grupo que consiste en: cicloalquilo C₇₋₁₂, alquenilo C₂₋₆, alquinilo C₂₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, heterociclilo de 4 miembros, heterociclilo de 7 miembros, heterociclilo monocíclico de 7 - 12 miembros, -SF₅, -NR¹³R¹³, -NR¹³C(O)OR¹⁴, -NR¹³SO₂R¹⁴, -NR¹³S(O)₂NR¹³R¹³, -NR¹³C(O)NR¹³R¹³, trialquilsililo C₁₋₄, -C(O)R¹⁴, -C(O)OR¹⁴, -C(O)NR¹³R¹³, -S(O)₀₋₂R¹⁴, -S(O)(NH)R¹⁴, -S(O)(NR⁸)R¹⁴, -S(O)(NH)NR¹³R¹³, -S(O)(NR⁸)NR¹³R¹³, -SH y -NO₂, en donde cicloalquilo C₇₋₁₂, alquenilo C₂₋₆, alquinilo C₂₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, heterociclilo de 4 miembros, heterociclilo de 7 miembros y heterociclilo monocíclico de 7 - 12 miembros están opcionalmente sustituidos con uno o más R⁹; el heterociclilo de 5 - 6 miembros está opcionalmente sustituido con R¹⁷; y el heterociclilo bicíclico de 8 - 10 miembros está opcionalmente sustituido con uno o más R¹⁸; (ii) cuando R⁶ es un anillo heterobicíclico de 8 - 10 miembros, R³ es H y R⁷ es -H, halo, ciano, oxo, -OH, alcoxi C₁₋₄, alquilo C₁₋₄ o halo-alquilo C₁₋₄, entonces R⁴ se selecciona del grupo que consiste en: cicloalquilo C₇₋₁₂, alquenilo C₂₋₆, alquinilo C₂₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, heterociclilo de 4 miembros, heterociclilo de 7 miembros, heterociclilo monocíclico de 7 - 12 miembros, -SF₅, -NR¹³R¹³, -NR¹³C(O)OR¹⁴, -NR¹³SO₂R¹⁴, -NR¹³S(O)₂NR¹³R¹³, -NR¹³C(O)NR¹³R¹³, trialquilsililo C₁₋₄, -C(O)R¹⁴, -C(O)OR¹⁴, -C(O)NR¹³R¹³, -S(O)₀₋₂R¹⁴, -S(O)(NH)R¹⁴, -S(O)(NR⁸)R¹⁴, -S(O)(NH)NR¹³R¹³, -S(O)(NR⁸)NR¹³R¹³, -SH, y -NO₂, en donde cicloalquilo C₇₋₁₂, alquenilo C₂₋₆, alquinilo C₂₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, heterociclilo de 4 miembros, heterociclilo de 7 miembros y heterociclilo monocíclico de 7 - 12 miembros están opcionalmente sustituidos con uno o más R⁹; el heterociclilo de 5 - 6 miembros está opcionalmente sustituido con R¹⁷, y el heterociclilo bicíclico de 8 - 10 miembros está opcionalmente sustituido con uno o más R¹⁸; (iii) cuando R⁶ es un anillo carbocíclico C₆₋₇, y R⁷ es H o metilo, entonces R³ se selecciona del grupo que consiste en: halo, -CN, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros, heteroarilo de 5 - 10 miembros, -SF₅, -S(O)₀₋₂R¹⁴, -S(O)(NH)R¹⁴, -S(O)(NR⁸)R¹⁴, -S(O)(NH)NR¹³R¹³, -S(O)(NR⁸)NR¹³R¹³, -SH, -NR¹³R¹³, -NR¹³SO₂R¹⁴, -NR¹³S(O)₂NR¹³R¹³, -NR¹³C(O)NR¹³R¹³, -NR¹³C(O)OR¹⁴, trialquilsililo C₁₋₄, -C(O)R¹⁴, -C(O)OR¹⁴, -C(O)NR¹³R¹³, y -NO₂, en donde alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros y heteroarilo de 5 - 10 miembros son opcionalmente sustituido con uno o más grupos R⁹; en donde R¹⁷ se selecciona de -OH, oxo, -CN, alquenilo C₂₋₆, alquinilo C₂₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 - 12 miembros, arilo de 6 - 10 miembros, heteroarilo de 5 - 10 miembros, -S(O)₀₋₂R¹⁴, -NR¹³SO₂R¹⁴, -NR¹³S(O)₂NR¹³R¹³, -NR¹³C(O)NR¹³R¹³, -NR¹³C(O)OR¹⁴, -C(O)R¹⁴, -C(O)OR¹⁴ y -C(O)NR¹³R¹³; y en donde R¹⁸ se selecciona de alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, hidroxialquilo C₁₋₆, heteroalquilo C₁₋₆, cicloalquilo de 3 - 12 miembros, heterociclilo de 4 - 12 miembros, arilo de 10 miembros, heteroarilo de 5 - 10 miembros, -S(O)₀₋₂R¹⁴, -NR¹³R¹³, -NR¹³SO₂R¹⁴, -NR¹³S(O)₂NR¹³R¹³, -NR¹³C(O)NR¹³R¹³, -NR¹³C(O)OR¹⁴, -C(O)R¹⁴, -C(O)OR¹⁴ y -C(O)NR¹³R¹³.
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