CO5261499A1 - Inhibidores de neuraminidasas - Google Patents

Inhibidores de neuraminidasas

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Publication number
CO5261499A1
CO5261499A1 CO00079306A CO00079306A CO5261499A1 CO 5261499 A1 CO5261499 A1 CO 5261499A1 CO 00079306 A CO00079306 A CO 00079306A CO 00079306 A CO00079306 A CO 00079306A CO 5261499 A1 CO5261499 A1 CO 5261499A1
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Colombia
Prior art keywords
alkyl
alkenyl
cycloalkenyl
cycloalkyl
heterocyclic
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CO00079306A
Other languages
English (en)
Inventor
Clarence J Maring
Gu Yu-Gui
Chen Hui-Ju
Chen Yuanwei
David A Degoey
William J Fiosi
Vincent L Giranda
David J Grampovnik
M Kati Warren
Dale J Kempf
L Kennedy April
Larry L Klein
Allan C Krueger
Lin Zhen
Darold L Madigan
Keith F Mcdaniel
Steven W Muchmore
D Stewart Kent
Vincent S Stoll
Sun Minghua
P Tu Noah
Frank L Wagenaar
Gary T Wang
Wang Sheldon
Paul E Wiedeman
Xu Yibo
C Yeung Ming
Zhao Chen
Hanessian Steohen
Bayrakdarian Malken
Luo Xuehong
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Abbott Lab
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Application filed by Abbott Lab filed Critical Abbott Lab
Publication of CO5261499A1 publication Critical patent/CO5261499A1/es

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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
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    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
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    • 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
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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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    • C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms

Abstract

Un compuesto enriquecido enantioméricamente CARACTERIZADO PORQUE tiene la estereoquímica absoluta de la fórmula: <EMI FILE="00079306_1" ID="1" IMF=JPEG >o una sal, un éster o una prodroga aceptable para uso farmacéutico de los mismosdonde R1 se selecciona del grupo formado por (a) -CO2H, (b) -CH2CO2H, (c) -SO3H, (d) -CH2SO3H, (e) -SO2H, (f) -CH2SO2H, (g) -PO3H2, (h) -CH2PO3H2, (i) -PO2H, o) -CH2PO2H, (k) tetrazolilo, (l) -CH2-tetrazolilo, (m) -C(=O)-NH-S(O)2-R11, (n) -CH2C(=O)-NH-S(O)2-R11, (o) -SO2N(T-R11)R12 y (p) -CH2SO2N(T-R11)R12donde T se selecciona del grupo formado por (i) un enlace, (ii) -C(=O)-, (iii) -C(=O)O-, (iv) -C(=O)S-, (v) -C(O)NR36, (vi) -C(=S)O-, (vii) -C(=S)S- y (viii) -C(=S)NR36-,R11 se selecciona del grupo formado por(i) C1-C12-alquilo, (ii) C2-C12 -alquenilo, (iii) cicloalquilo, (iv) (cicloalquil)alquilo, (v) (cicloalquil)alquenilo, (vi) cicloalquenilo, (vii) (cicloalquenil)alquilo, (viii) (cicloalquenil)alquenilo, (ix) arilo, (x) (aril)alquilo, (xi) (aril)alquenilo, (xii) heterocíclico, (xiii) alquilo(heterocíclico) y (xiv) alquenilo(heterocíclico); y R12 y R36 se selecionan independiente entre sí, del grupo formado - 2 -(i) hidrógeno, (ii) C1-C12-alquilo, (iii) C1-C12-alquenilo, (iv) cicloalquilo (v) (cicloalquil)alquilo, (vi) (cicloalquil)alquenilo, (vii) cicloalquenilo, (viii) (cicloalquenil)alquilo, (ix) (cicloalquenil)alquenilo, (x) arilo, (xi) (aril)alquilo, (xii) (aril)alquenilo, (xiii) heterocíclico, (xiv) alquilo (heterocíclico) y (xv) alquenilo(heterocíclico)X se selecciona del grupo formado por (a -C(=O)-N(R*)-, (b)-N(R*)-C(=O)-, (c)-C(=S)-N(R*)-, (d) -N(R*)-C(=S)-, (e)-N(R*)-SO2-, y M -SO2-N(R*)-, donde R* es hidrógeno, C1-C3-alquilo inferior o ciclopropilo, R2 se selecciona del grupo formado por (a) hidrógeno, (b) C1-C6-alquilo, (C) C2-C6-alquenilo, (d) C3C6 cicloalquilo, (e) C5-C6-cicloalquenilo, (f) halo-C1-C6-alquilo y (g) halo-C2-C6-alquenilo; o R2-X es <EMI FILE="00079306_2" ID="2" IMF=JPEG >donde Y1 es -CH2-, -O-, -S- o -NH- e Y2 es -C(=O)- o -C(Raa)(Rbb), donde Raa y Rbb se seleccionan, independientemente entre sí, del grupo formado por hidrógeno, C1-C3-alquilo inferior, hidroximetilo, 1 -hidroxietilo, 2-hidroxietilo, aminometilo, 1-aminoetilo, 2-aminoetilo, tiolmetilo, 1-tioletilo, 2-tioletilo, metoximetilo, N-metilaminometilo y metiltiometilo; R3 y R4 se seleccionan, independientemente entre sí, del grupo formado por (a) hidrógeno, (b) cicloalquilo, (c) cicloalquenilo, (d) heterocíclico, (e) arilo y (f) -Z-R14 donde Z es (i) -C(R37a)(R37b)-, (ii)-C(R47)=C(R48)-, (iii)-C=C-, (iv) -C(=O)-(v) -C(=S)-, (vi) -C(=NR15)-, (vii) -C(R37a)(OR37c)-, (viii) -C(R37a)(SR37c)-, (ix) -C(R37a)(N(R37b)(R37c))-, (x) -C(R37a)(R37b)-O-, (xi) -C(R37a)(R37b)-N(R37c)-, (xii) -C(R37a)(R37b)-N(O)(R37c), (xiii) -C(R37a)(R37b)-N(OH)-, (xiv) -C(R37a)(R37b)-S-, (xv) -C(R37a)(R37b)-S(O), (xvi) -C(R37a)(R37b)-S(O)2-, (xvii) -C(R37a)(R37b)-C(=O)-, (xviii) -C(R37a)(R37b)-C(=S)-, (xix) -C(R37a)(R37b)-C(=NR15)-, (xx) -C(R37a)(OR37c)-C(=O)-, (xxi) -C(R37a)(SR37b)-C(=O)-, (xxii) -C(R37a)(R37c)-C(=S)-, (xxiii) -C(R37a)(SR37c)-C(=S)-, (xxiv) -C(=O)-C(R37a)(OR37c)-, (xxv) -C(=O)-C(R37a)(SR37c)-, (xxvi) -C(=S)-C(R37a)(OR37c)-, (xxvii) -C(=S)-C(R37a)(SR37c)-, (xxviii) -C(R37a)(OR37c)-C(R37a)(OR37c)-, (xxix)-C(R37a)(SR37c)-C(R37a)(OR37c)-, (xxx) -C(R37a)(OR37c)-C(R37a)(SR37c)-, (xxxi) -C(R37a)(SR37c)-C(R37a)(SR37c)-, (xxxii) -C(=O)-C(=O)-, (xxxiii) -C(=S)-C(=S)-, (xxxiv) -C(=O)-O-, (xxxv) -C(=O)-S-, (xxxvi) -C(=S)-O-, (xxxvii) -C(=S)-S-, (xxxviii) -C(=O)-N(R37a)- (xxxix) -C(=S)-N(R37a)-, (xI) -C(R37a)(R37b)-C(=O)-N(R37a)-, (xli) -C(R37a)(R37b)-C(=S)-N(R37a)-, (xlii) -C(R37a (R37b)-C(=O)-O-, (xliii) -C(R37a)(R37b)-C(=O)-S-, (xliv) -C(R37a)(R37b)-C(=S)-O, (xlv) -C(R37a)(R37b)-C(=S)-S-, (xlvi) -C(37a)(R37b)N(R37b)-C(=O)-, (xlvii) -C(R37a)(R37b)-N(R37b)-C(=S)-, (xlviii) -C(R37a)(R37b)-O-C(=O)- (xlix) -C(R37a)(R37b)-S-C(=O)-, (l) -C(R37a)(R37b)-O-C(=S)-, (li) -C(R37a)(R37b)-S-C(=S)-, (Iii) -C(R37a)(R37b)-N(R37b)-C(=O)-N(R37a)-, (Iiii) -C(R37a)(R37b)-N(R37b)-C(=S)-N(R37a)-, (liv) -C(R37a)(R37b)-N(R37b)-C(=O)-O-, (Iv) -C(R37a) (R37b)-N(R37b)-C(=O)-S-, (Ivi) -C(R37a)(R37b)-N(R37b)-C(=S)-O-, (lvii) -C(R37a)(R37b)-N(R37b)-C(=S)-S-, (lviii) -C(R37a)(R37b)-O-C(=O)-N(R37a)-, (lix) -C(R37a)(R37b)-S-C(=O)-N(R37a)-, (Ix) -C(R37a)(R37b)-O-C(=S)-N(R37a)-, (Ixi) -C(R37a)(R37b)-S-C(=S)-N(R37a)-, (Ixii) -C(R37a)(R37b)-O-C(=O)-O-, (Ixiii) -C(R37a)(R37b)-S-C(=O)-O-, (Ixiv) -C(R37a)(R37b)-O-C(=O)-S-, (Ixv) -C(R37a)(R37b)-S-C(=O)-S-, (Ixvi) -C(R37a)(R37b)-O-C(=S)-O-, (Ixvii) -C(R37a)(R37b)-S-C(=S)-O-, (lxviii) -C(R37a)(R37b)-O-C(=S)-S-, (Ixix) -C(R37a)(R37b)-S-C(=S)-S- o (Ixx) -C(R37a)(R37b)-C(R37a)(OR37c); R14 es (i) hidrógeno, (ii) C1-CI2-alquilo, (iii) haloalquilo, (iv) hidroxialquilo, (v) alquilo tiol-sustituido, (vi) alquilo R37c-O-sustituido, (vii) alquilo R37c-S-sustituido, (viii) aminoalquilo, (ix) alquilo (R37C)NH-sustituido, (x) alquilo (R37a)(R37c)N- sustituido, (xi) alquilo R37aO-(O=)C-sustituido, (xii) alquilo R37a-S-(O=)C sustituido, (xiii) alquilo R37aO-(S=)C-sustituido, (xiv)alquilo R37a-S-(S=)C sustituido, (xv) alquilo (R37aO)2-P(=O)-sustituido, (xvi) cianoalquilo, (xvi)C1-C12- alquenilo, (xviii) haloalquenilo, (xix) C2-C12-alquinilo, (xx) cicloalquilo, (xxi) (cicloalquil)alquilo, (xxii) (cicloalquil)alquenilo, (xxiii) (cicloalquil)alquinilo, (xxiv) cicloalquenilo (xxv) (cicloalquenil) alquilo, (xxvi) - 3 -(cicloalquenil)alquenilo, (xxvii) (cicloalquenil)alquinilo, (xxviii) arilo, (xxix) (aril) alquilo, (xxx) (aril)alquenilo, (xxxi) (aril)alquinilo, (xxxii) heterocíclico, (xxxiii) alquilo (heterocíclico), (xxxiv) alquenilo(heterocíclico) o (xxxv) (heterocíclico)alquinilo, con la condición que R14 es distinto de hidrógeno cuando Z es -C(R37a)(R37b)-N(R37b)-C(=O)-(O)-, -C(R37a)(R37b)-N(R37b)-C(=S)-O-, -C(R37a)(R37b)-N(R37b)-C(=O)-O-, -C(R37a)(R37b)-N(R37b)-C(=S)-S-, -C(R37a)(R37b)-O-C(=O)-O-, -C(R37a)(R37b)-O-C(=S)-O-, -C(R37a)(R37b)-S-C(=O)-O-, -C(R37a)(R37b)-S-C(=S)-O-, -C(R37a)(R37b)-O-C(=O)-S-, -C(R37a)(R37b)-O-C(=S)-S-, C(R37a)(R37b)-S-C(=O)S o -C(R37a)R37b)-S-C(=S)-S-; R37a, R37b y R47 y R48 se seleccionan en cada aparición, independientemente entre sí, del grupo formado por (i) hidrógeno, (ii) C1-C12-alquilo, (iii) haloalquilo, (iv) hidroxialquilo, (v) alcoxialquilo, (vi) C2-C12-alquenilo, (vii) haloalquenilo, (viii) C2-C12-alquinilo, (ix) cicloalquilo, (x) (cicloalquil)alquilo, (xi) (cicloalquil)alquenilo, (xii) (cicloalquil)alquinilo, (xiii) cicloalquenilo, (xiv) (cicloalquenil) alquilo, (xv) (cicloalquenil)alquenilo, (xvi) (cicloalquenil)alquinilo, (xvii) arilo, (xviii) (aril)alquilo, (xix) (aril)alquenilo, (xx)(aril)alquinilo, (xxi)heterocíclico, (xxii) alquilo(heterocíclico), (xxiii) alquenilo(heterocíclico) y (xxiv) alquinilo(heterocíclico), R37c se selecciona en cada aparición, independientemente, del grupo formado por (i) hidrógeno, (ii) C1-C12-alquilo, (iii) haloalquilo, (iv) C2-C12-alquenilo, (v) haloalquenilo, (vi) C2-C12-alquinilo, (vii) cicloalquilo, (viii) (cicloalquil)alquilo, (ix) (cicloalquil)alquenilo, (x) (cicloalquil) alquinilo, (xi) cicloalquenilo, (xii) (cicloalquenil)alquilo, (xiii) (cicloalquenil)alquenilo, (xiv) (cicloalquenil)alquinilo, (xv) arilo, (xvi) (aril)alquilo, (xvii) (aril)alquenilo, (xviii) (aril)alquinilo, (xix) heterocíclico, (xx) alquilo(heterocíclico), (xxi) alquenilo(heterocíclico), (xxii) alquinilo (heterocíclico), (xxiii)-O(=O)-R14, (xxiv)-C(=S)-R, (xxv)-S(O)2-R14 y (xxvi) hidroxialquilo; o cuando Z es -C(R37a)(R37b)-N(R37c)-, entonces cuando N(R37c) y R14 se toman juntos constituyen un grupo azido; o cuando Z es -C(R37a)(R37b)-N(O)(R37c)-, entonces cuando N(O)(R37c) y R14 se toman juntos constituyen un anillo heterocíclico de 3-7 miembros N-oxidado que posee por lo menos un átomo de nitrógeno en el anillo N-oxidado, o cuando Z es -C(R37a)(OR37b)-, -C(R37a)(SR37c)-o- -C(R37a)(N(R37b)(R37c))-, entonces R37a, R14 y el átomo de carbono al que están unidos cuando se toman juntos forman un anillo ciclopentilo, ciclopentenilo, ciclohexilo o ciclohexenilo o entonces OR37c o SR37c o N(R37c) y R14 y el átomo de carbono al que están unidos cuando se toman juntos forman un anillo heterocíclico que contiene un átomo de O, S o N, respectivamente, y contiene entre 4 y 8 átomos del anillo; R15 se selecciona del grupo formado por (i) hidrógeno, (ii) hidroxi, (iii) amino, (iv) C1-C12-alquilo, (v) haloalquilo, (vi) C2-C12-alquenilo (vii) haloalquenilo, (viii) cicloalquilo (ix) (cicloalquil)alquilo, (x) (cicloalquil)alquenilo, (xi) cicloalquenilo, (xii) (cicloalquenil)alquilo, (xiii) (cicloalquenil)aIquenilo, (xiv) arilo, (xv) (aril)alquilo, (xvi)(aril)alquenilo, (xvii) heterocíclico, (xviii) alquilo(heterocíclico) y (xix) alquenilo(heterocíclico), o R3 y R4 tomados juntos, con el átomo al cual están unidos, forman un anillo carbocíclico o heterocíclico que posee de 3 a 8 átomos en el anillo, R5 se selecciona del grupo formado por (a) hidrógeno, (b) -CH(R38)2, (c) -O-R40, (d) C2-C4-alquinilo, (e) ciclopropilo, (f) ciclobutilo, (g) -C(=Q1)-R17 y (h) -N(R19)2 donde Q1 es O, S o N(R18); R17 y R18 se seleccionan Independientemente, en cada aparición, del grupo formado por hidrógeno, metilo y etilo; R19, R38 y R40 se seleccionan independientemente, en cada aparición, del grupo formado por (i) hidrógeno (ii) C1-C12-alquilo, (iii) haloalquilo, (iv) C2-C12-alquenilo, (v) haloalquenilo, (vi) cicloalquilo, (vii) (cicloalquil)alquilo, (viii) (cicloalquil)alquenilo, (ix) cicloalquenilo, (x) (cicloalquenil)alquilo, (xi) (cicloalquenil)alquenilo, (xii) arilo, (xiii) (aril)alquilo (xiv) (aril)alquenilo, (xv) heterocíclico, (xvi) alquilo(heterocíclico) y (xvii) alquenilo(heterocíclico);Y se selecciona del grupo formado por - 4 -(a) hidrógeno, (b) C1-C5-alquilo, (c) C1-C5-haloalquilo, (d) C2-C5-alquenilo, (e) C2-C5-haloalquenilo, (f) C2-C5-alquinilo, (g) C3-C5-cicloalquilo, (h C3-C5-cicloalquil-C1-a-C3-alquilo, (i) C5-cicloalquenilo, (j) C5-cicloalquenil-C1-a-C3-alquilo, (k) C5-cicloa
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MXPA02003971A (es) 2003-01-28
JP2003513889A (ja) 2003-04-15
WO2001028996A2 (en) 2001-04-26
KR20020047250A (ko) 2002-06-21
BR0010555A (pt) 2003-09-23
AU1076001A (en) 2001-04-30
CA2388859A1 (en) 2001-04-26
AR026173A1 (es) 2003-01-29
US6455571B1 (en) 2002-09-24
CN1450990A (zh) 2003-10-22
US20040097471A1 (en) 2004-05-20
EP1358154A2 (en) 2003-11-05

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