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AR082080A1 - Compuestos derivados de acido acetico-2-quinolinicos como compuestos antivirales anti hiv - Google Patents

Compuestos derivados de acido acetico-2-quinolinicos como compuestos antivirales anti hiv

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Publication number
AR082080A1
AR082080A1 ARP110102377A ARP110102377A AR082080A1 AR 082080 A1 AR082080 A1 AR 082080A1 AR P110102377 A ARP110102377 A AR P110102377A AR P110102377 A ARP110102377 A AR P110102377A AR 082080 A1 AR082080 A1 AR 082080A1
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AR
Argentina
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alkyl
carbocycle
groups
alkenyl
heterocycle
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ARP110102377A
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Gilead Sciences Inc
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Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc
Publication of AR082080A1 publication Critical patent/AR082080A1/es

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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • 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
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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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    • 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
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    • 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
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    • 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
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    • 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
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Reivindicación 1: Un compuesto de la fórmula (1) en donde G1 es N, G2 es CR8, y el enlace punteado es un enlace doble; o G1 es CR5, G2 es N, y el enlace punteado es un enlace doble; o G1 es CR5, G2 es NR13, el enlace punteado es un enlace simple, y R7 es un grupo oxo (=O); o G1 es CR5, G2 es NR13, el enlace punteado es un enlace simple, y R7 y R13 junto con los átomos a los que están unidos forman un heteroarilo, en donde el heteroarilo está opcionalmente sustituido con uno o más grupos Z1; R1 es R1a o R1b; R2 es R2a o R2b; R3 es R3a o R3b; R3’ es R3a’ o R3b’; R4 es R4a o R4b; R5 es R5a o R5b; R6 es R6a o R6b; R7 es R7a o R7b; R8 es R8a o R8b; R13 es R13a o R13b; R1a se selecciona de: a) H, halo, alquilo C1-6 y haloalquilo C1-6; b) alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, nitro, ciano, arilo, heterociclo y heteroarilo; c) -C(=O)-R11, -C(=O)-O-R11, -O-R11, -S-R11, -S(O)-R11, -SO2-R11, -alquil C1-6-R11, -alquil C1-6-C(=O)-R11, -alquil C1-6-C(=O)-O-R11, -alquil C1-6-O-R11, -alquil C1-6-S-R11, -alquil C1-6-S(O)-R11 y -alquil C1-6-SO2-R11, en donde cada R11 es independientemente seleccionado de H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, cicloalquilo C3-7, arilo, heterociclo y heteroarilo; y d) -N(R9)R10, -C(=O)-N(R9)R10, -O-C(=O)-N(R9)R10, -SO2-N(R9)R10, -alquil C1-6-N(R9)R10, -alquil C1-6-C(=O)-N(R9)R10, -alquil C1-6-O-C(=O)-N(R9)R10 y -alquil C1-6-SO2-N(R9)R10, en donde cada R9 es independientemente seleccionado de H, alquilo C1-6 y cicloalquilo C3-7, y cada R10 es independientemente seleccionado de R11, -alquil C1-6-R11, -SO2-R11, -C(=O)-R11, -C(=O)OR11 y -C(=O)N(R9)R11, en donde cada R11 es independientemente seleccionado de H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, cicloalquilo C3-7, arilo, heterociclo y heteroarilo; y en donde cualquier arilo, heterociclo o heteroarilo de R1a está opcionalmente sustituido con uno o más grupos Z10; R1b se selecciona de: a) -alquil C1-6-O-alquil C1-6-carbociclo C3-7, -alquil C1-6-S-alquil C1-6-carbociclo C3-7, -alquil C1-6-S(O)-alquil C1-6-carbociclo C3-7, -alquil C1-6-SO2-alquil C1-6-carbociclo C3-7, -alquil C1-6-SO2-alquil C1-6-Z13, -C(O)-alquil C1-6-Z13, -O-alquil C1-6-Z13, -S-alquil C1-6-Z13, -S(O)-alquil C1-6-Z13, -SO2-alquil C1-6-Z13, -alquil C1-6-Z14, -alquil C1-6-C(O)-alquil C1-6-Z13, -alquil C1-6-C(O)-O-alquil C1-6-Z13, -alquil C1-6-O-alquil C1-6-Z13, -alquil C1-6-S-alquil C1-6-Z13, -alquenil C2-6-haloalquilo C1-6, -alquinil C2-6-haloalquilo C1-6, -halocarbociclo C3-7, -NRaSO2NRcRd, -NRaSO2O-carbociclo C3-7, -NRaSO2O-arilo, -alquenil C2-6-carbociclo C3-7, -alquenil C2-6-arilo, -alquenil C2-6-heteroarilo, -alquenil C2-6-heterociclo, -alquinil C2-6-carbociclo C3-7, -alquinil C2-6-arilo, -alquinil C2-6-heteroarilo, -alquinil C2-6-heterociclo, -carbociclo C3-7-Z1 y -haloalquil C1-6-Z3, en donde cualquier alquilo C1-6, haloalquilo C1-6, carbociclo C3-7, halocarbociclo C3-7, alquenilo C2-6, alquinilo C2-6, arilo, heterociclo y heteroarilo, ya sea solo o como parte de un grupo, está opcionalmente sustituido con uno o más grupos Z1; b) carbociclo bicíclico espiro, carbociclo bicíclico fusionado y carbociclo bicíclico puenteado, en donde cualquier carbociclo bicíclico espiro, carbociclo bicíclico fusionado y carbociclo bicíclico puenteado está opcionalmente sustituido con uno o más grupos Z1, en donde dos grupos Z1 juntos con el átomo o átomos al que están unidos opcionalmente forman un carbociclo C3-7 o heterociclo, en donde el carbociclo C3-7 o heterociclo está opcionalmente sustituido con uno o más grupos Z1; c) alquilo C1-6, en donde alquilo C1-6 está sustituido con uno más grupos Z2 y opcionalmente sustituido con uno o más grupos Z1; d) -X-alquilo C1-6, -X-haloalquilo C1-6, -X-alquenilo C2-6, -X-alquinilo C2-6 y -X-carbociclo C3-7, en donde cualquier -X-alquilo C1-6, -X-haloalquilo C1-6 está sustituido con uno o más grupos Z3 y opcionalmente sustituidos con uno o más grupos Z1, y en donde -X-alquenilo C2-6, -X-alquinilo C2-6 y -X-carbociclo C3-7 está sustituido con uno o más grupos Z4 y opcionalmente sustituidos con uno o más grupos Z1; e) arilo, heteroarilo, heterociclo, -X-arilo, -X-heteroarilo y -X-heterociclo; en donde cualquier arilo heteroarilo y heterociclo, ya sea solo o como una parte de un grupo, está sustituido con uno o más grupos Z5 y opcionalmente sustituidos con un o más grupos Z1; f) haloalquilo C1-6, carbociclo C3-7, alquenilo C2-6, y alquinilo C2-6, en donde haloalquilo C1-6, carbociclo C3-7, alquenilo C2-6 y alquinilo C2-6 están cada uno sustituidos con uno o más grupos Z6 y opcionalmente sustituidos con uno o más grupos Z1; y g) -NReRf, -C(O)NReRf, -OC(O)NReRf, -SO2NReRf, -alquil C1-6-NReRf, -alquil C1-6C(O)-NReRf, -alquil C1-6-O-C(O)-NReRf y -alquil C1-6-SO2NReRf, en donde cada cualquier alquilo C1-6, como parte de un grupo, está opcionalmente sustituido con uno o más grupos Z1; R2a se selecciona de: a) H, alquilo C1-6 y -O-alquilo C1-6; b) alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, cicloalquilo C3-7, arilo, heterociclo, heteroarilo, halo, nitro y ciano; c) -C(=O)-R11, -C(=O)-O-R11, -S-R11, -S(O)-R11, -SO2-R11, -alquil C1-6-R11, -alquil C1-6-C(=O)-R11, -alquil C1-6-C(=O)-O-R11, -alquil C1-6-O-R11, -alquil C1-6-S-R11, -alquil C1-6-S(O)-R11 y -alquil C1-6-SO2-R11, en donde cada R11 está independientemente seleccionado de H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, cicloalquilo C3-7, arilo, y heterociclo y heteroarilo; en donde cada R11 está independientemente seleccionado de H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, cicloalquilo C3-7, arilo y heterociclo y heteroarilo, en donde arilo, heterociclo y heteroarilo están cada uno opcionalmente sustituidos con uno o más grupos Z11; d) -OH, -O-alquenilo C2-6, -O-alquinilo C2-6, -O-haloalquilo C1-6, -O-cicloalquilo C3-7, -O-arilo, -O-heterociclo y -O-heteroarilo; e) -N(R9)R10, -C(=O)-N(R9)R10, -O-C(=O)-N(R9)R10, -SO2-N(R9)R10, -alquil C1-6-N(R9)R10, -alquil C1-6-C(=O)-N(R9)R10, -alquil C1-6-O-C(=O)-N(R9)R10 y -alquil C1-6-SO2-N(R9)R10, en donde cada R9 es independientemente seleccionado de H, alquilo C1-6 y cicloalquilo C3-7, y cada R10 es independientemente seleccionado de R11, -alquil C1-6-R11, -SO2-R11, -C(=O)-R11, -C(=O)OR11 y -C(=O)N(R9)R11, en donde cada R11 es independientemente seleccionado de H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, cicloalquilo C3-7, arilo, heterociclo y heteroarilo; R2b se selecciona de: a) -alquil C1-6-O-alquil C1-6-carbociclo C3-7, -alquil C1-6-S-alquil C1-6-carbociclo C3-7, -alquil C1-6-S(O)-alquil C1-6-carbociclo C3-7, -alquil C1-6-SO2-alquil C1-6-carbociclo C3-7, -alquenil C2-6-haloalquilo C1-6, -alquinil C2-6-haloalquilo C1-6, -alquil C1-6-SO2-alquil C1-6-Z13, -C(O)-alquil C1-6-Z13, -O-alquil C1-6-Z13, -S-alquil C1-6-Z13, -S(O)-alquil C1-6-Z13, -SO2-alquil C1-6-Z13, -alquil C1-6-Z14, -alquil C1-6-C(O)-alquil C1-6-Z13, -alquil C1-6-C(O)-O-alquil C1-6-Z13, -alquil C1-6-O-alquil C1-6-Z13, -alquil C1-6-S-alquil C1-6-Z13 , -halocarbociclo C3-7, -NRaSO2NRcRd, -NRaSO2O-carbociclo C3-7, -NRaSO2O-arilo, -alquenil C2-6-carbociclo C3-7, -alquenil C2-6-arilo, -alquenil C2-6-heteroarilo, -alquenil C2-6-heterociclo, -alquinil C2-6-carbociclo C3-7, -alquinil C2-6-arilo, -alquinil C2-6-heteroarilo, -alquinil C2-6-heterociclo, -carbociclo C3-7-Z1 y -haloalquilo C1-6-Z3, en donde cualquier alquilo C1-6, -haloalquilo C1-6, carbociclo C3-7, halocarbociclo C3-7, alquenilo C2-6, alquinilo C2-6, arilo, heterociclo y heteroarilo, ya sea solo o como parte de un grupo, está opcionalmente sustituido con uno o más grupos Z1; b) carbociclo bicíclico espiro, carbociclo bicíclico fusionado y carbociclo bicíclico puenteado, en donde cualquier carbociclo bicíclico espiro, carbociclo bicíclico fusionado y carbociclo bicíclico puenteado está opcionalmente sustituido con uno o más grupos Z1, y en donde dos grupos Z1 juntos con el átomo o átomos al que están unidos opcionalmente forman un carbociclo C3-7 o heterociclo, en donde el carbociclo C3-7 o heterociclo está opcionalmente sustituido con uno o más grupos Z1; c) alquilo C1-6, en donde alquilo C1-6 está sustituido con uno más grupos Z2 y opcionalmente sustituido con uno o más grupos Z1; d) -X-alquilo C1-6, -X-haloalquilo C1-6, -X-alquenilo C2-6, -X-alquinilo C2-6 y -X-carbociclo C3-7, en donde cualquier -X-alquilo C1-6, -X-haloalquilo C1-6 está sustituido con uno o más grupos Z3 y opcionalmente sustituidos con uno o más grupos Z1, y en donde cualquier -X-alquenilo C2-6, -X-alquinilo C2-6 y -X-carbociclo C3-7 está sustituido con uno o más grupos Z4 y opcionalmente sustituido con uno o más grupos Z1; e) arilo, heteroarilo, heterociclo, -X-arilo, -X-heteroarilo y -X-heterociclo; en donde cualquier arilo heteroarilo y heterociclo, ya sea solo o como parte de un grupo, está sustituido con uno o más grupos Z5 y opcionalmente sustituidos con un o más grupos Z1; f) haloalquilo C1-6, carbociclo C3-7, alquenilo C2-6, y alquinilo C2-6, en donde haloalquilo C1-6, carbociclo C3-7, alquenilo C2-6 y alquinilo C2-6 están cada uno sustituidos con uno o más grupos Z6 y opcionalmente sustituidos con uno o más grupos Z1; y g) -NReRf, -C(O)NReRf, -OC(O)NReRf, -SO2NReRf, -alquil C1-6-NReRf, -alquil C1-6C(O)-NReRf, -alquil C1-6-O-C(O)-NReRf y -alquil C1-6-SO2NReRf, en donde cada alquilo C1-6 está opcionalmente sustituido con uno o más grupos Z1; R3a es alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6, -alquil C1-6-cicloalquilo C3-7, -alquil C1-6-arilo, -alquil C1-6-heterociclo, -alquil C1-6-heteroarilo, -O-alquilo C1-6, -O-haloalquilo C1-6, -O-alquenilo C2-6, -O-alquinilo C2-6, -O-cicloalquilo C3-7, -O-arilo, -O-alquil C1-6-cicloalquilo C3-7, -O-alquil C1-6-arilo, -O-alquil C1-6-heterociclo o –O-alquil C1-6-heteroarilo, en donde cualquier alquilo C1-6, haloalquilo C1-6, alquenilo C2-6 o alquinilo C2-6 de R3a, ya solo o como un grupo, está opcionalmente sustituido con uno o más grupos seleccionados de O-alqui
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ECSP13012418A (es) 2013-03-28
PT2588455T (pt) 2018-06-29
JP2015180696A (ja) 2015-10-15
US20130210801A1 (en) 2013-08-15
JP2013533885A (ja) 2013-08-29
PE20130525A1 (es) 2013-05-05
ES2669793T3 (es) 2018-05-29
CO6660514A2 (es) 2013-04-30
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BR112012033689A2 (pt) 2019-09-24
CA2802492A1 (en) 2012-01-05
AP2013006707A0 (en) 2013-02-28
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US9296758B2 (en) 2016-03-29
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