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AR055830A1 - Inhibidores de cxcr2 - Google Patents

Inhibidores de cxcr2

Info

Publication number
AR055830A1
AR055830A1 ARP050105577A ARP050105577A AR055830A1 AR 055830 A1 AR055830 A1 AR 055830A1 AR P050105577 A ARP050105577 A AR P050105577A AR P050105577 A ARP050105577 A AR P050105577A AR 055830 A1 AR055830 A1 AR 055830A1
Authority
AR
Argentina
Prior art keywords
atoms
alkyl
aryl
substituted
independently
Prior art date
Application number
ARP050105577A
Other languages
English (en)
Original Assignee
Sanofi Aventis Deutschland
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 Sanofi Aventis Deutschland filed Critical Sanofi Aventis Deutschland
Publication of AR055830A1 publication Critical patent/AR055830A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/68—One oxygen atom attached in position 4
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Abstract

Reivindicacion 1: Un compuesto de formula (1) en la que X es -CR3=CR4-, -CR5=N-, -N=CR6-, -NR7- o -S-; R3, R4, R5 y R6 son, independientemente entre sí, H, F, Cl, Br, I, alquilo que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, cicloalquilo que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 u 11 átomos de H pueden estar sustituidos con átomos de F, alcoxi que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, -S-alquilo que tiene1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, OH, CN, NO2, NR27R28, C(O)R29, C(O)NR30R31, S(O)oR32, S(O)pNR33R34, arilo, heteroarilo, arilalquilo donde el alquilo tiene 1, 2, 3, o 4 átomos de C o heteroarilalquilo donde el alquilo tiene 1, 2, 3, o 4 átomos de C; R27 es H o alquilo que tiene 1, 2, 3, o 4 átomos de C; R28 es H, alquilo tiene 1, 2, 3, o 4 átomos de C, arilo, C(O)H, C(O)alquilo donde el alquilo tiene 1, 2, 3, o 4 átomos de C o C(O)arilo; R29 es H, OH, alquilo con 1, 2, 3, o 4 átomos de C, alcoxi con 1, 2, 3, o 4 átomos de C o arilo; R30, R31, R33 y R34 son, independientemente entre sí, H, alquilo tiene 1, 2, 3, o 4 átomos de C, o arilo; R32 es OH, alquilo tiene 1, 2, 3, o 4 átomos de C, alcoxi con 1, 2, 3, o 4 átomos de C o arilo; o y p son, independientemente entre sí, 1 o 2; R7 es H, alquilo tiene 1, 2, 3, o 4 átomos de C o C(O)R35; R35 es H, alquilo con 1, 2, 3, o 4 átomos de C o arilo; Y1, Y2, Y3 e Y4 son, independientemente entre sí, -CR8- o N, con la condicion de que al menos dos de Y1, Y2, Y3 e Y4 se definan como -CR8-; R8 es H, F, Cl, Br, I, alquilo que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, cicloalquilo que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 u 11 átomos de H pueden estar sustituidos con átomos de F, alcoxi que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, -S-alquilo que tiene1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, OH, CN, NO2, NR36R37, C(O)R38, C(O)NR39R40, S(O)qR41, S(O)rNR42R43, arilo, heteroarilo, arilalquilo donde el alquilo tiene 1, 2, 3, o 4 átomos de C o heteroarilalquilo donde el alquilo tiene 1, 2, 3, o 4 átomos de C; R36 es H o alquilo que tiene 1, 2, 3, o 4 átomos de C; R37 es H, alquilo tiene 1, 2, 3, o 4 átomos de C, arilo, C(O)H, C(O)alquilo donde el alquilo tiene 1, 2, 3, o 4 átomos de C o C(O)arilo; R38 es H, OH, alquilo con 1, 2, 3, o 4 átomos de C, alcoxi con 1, 2, 3, o 4 átomos de C o arilo; R39, R40, R42 y R43 son, independientemente entre sí, H, alquilo tiene 1, 2, 3, o 4 átomos de C, o arilo; R41 es OH, alquilo tiene 1, 2, 3, o 4 átomos de C, alcoxi con 1, 2, 3, o 4 átomos de C o arilo; q y r son, independientemente entre sí, 1 o 2; A es cicloalquilo que tiene 3, 4, 5, 6, 7 u 8 átomos de C, heterociclo, arilo o heteroarilo; donde el radical cicloalquilo o heterociclo puede condensarse a un radical arilo o heteroarilo y donde el radical cicloalquilo o heterociclo y el radical arilo o heteroarilo opcionalmente condensado están sin sustituir o sustituidos con 1, 2, 3 o 4 radicales seleccionados entre el grupo que consiste en F, Cl, Br, I, OH, CN, NO2, SF5, alquilo que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, cicloalquilo que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 u 11 átomos de H pueden estar sustituidos con átomos de F, alcoxi que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, -S-alquilo que tiene1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, - NR9R10, C(O)R44, C(O)NR45R46, S(O)sR47, S(O)tNR48R49, -(CH2)k-arilo o -(CH2)l-heteroarilo, donde los radicales arilo y heteroarilo pueden estar sustituidos con F, Cl, Br, I, alcoxi que tiene 1, 2, 3 o 4 átomos de C, alquilo que tiene 1, 2, 3, o 4 átomos de C u Oa-(CH2)b-(CF2)c-CF3; R9 es H o alquilo que tiene 1, 2, 3, o 4 átomos de C; R10 es H, alquilo que tiene 1, 2, 3, o 4 átomos de C, arilo, C(O)H, C(O)alquilo que tiene 1, 2, 3, o 4 átomos de C o C(O)arilo; R44 es H, OH, alquilo con 1, 2, 3, o 4 átomos de C, alcoxi con 1, 2, 3, o 4 átomos de C, cicloalquilo que tiene 3, 4, 5 o 6 átomos de C o arilo; R45, R46, R48 y R49 son, independientemente entre sí, H, alquilo tiene 1, 2, 3, o 4 átomos de C, o arilo; R47 es OH, alquilo tiene 1, 2, 3, o 4 átomos de C, alcoxi con 1, 2, 3, o 4 átomos de C o arilo; a es 0 o 1; b, c, k y l son, independientemente entre sí, 0, 1, 2 o 3; s y t son, independientemente entre sí, 1 o 2; donde el radical arilo o heteroarilo puede condensarse a un radical cicloalquilo o heterociclo y donde el radical arilo o heteroarilo y el radical cicloalquilo o heterociclo opcionalmente condensado están sin sustituir o sustituidos con 1, 2, 3, o 4 radicales seleccionados entre el grupo que consiste en F, Cl, Br, I, OH, CN, NO2, SF5, alquilo que tiene1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, cicloalquilo que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 u 11 átomos de H pueden estar sustituidos con átomos de F, alcoxi que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, -S-alquilo que tiene1, 2, 3, 4, 5 o 6 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 o 13 átomos de H pueden estar sustituidos con átomos de F, -NR9R10, C(O)R44, C(O)NR45R46, S(O)sR47, S(O)tNR48R49, -(CH2)k-arilo o -(CH2)l-heteroarilo, donde los radicales arilo y heteroarilo pueden estar sustituidos con F, Cl, Br, I, alcoxi que tiene 1, 2, 3 o 4 átomos de C, alquilo que tiene 1, 2, 3, o 4 átomos de C u Oa-(CH2)b-(CF2)c-CF3; R9 es H o alquilo que tiene 1, 2, 3, o 4 átomos de C; R10 es H, alquilo que tiene 1, 2, 3, o 4 átomos de C, arilo, C(O)H, C(O)alquilo que tiene 1, 2, 3, o 4 átomos de C o C(O)arilo; R44 es H, OH, alquilo con 1, 2, 3, o 4 átomos de C, alcoxi con 1, 2, 3, o 4 átomos de C, cicloalquilo que tiene 3, 4, 5 o 6 átomos de C o arilo; R45, R46, R48 y R49 son, independientemente entre sí, H, alquilo tiene 1, 2, 3, o 4 átomos de C, o arilo; R47 es OH, alquilo tiene 1, 2, 3, o 4 átomos de C, alcoxi con 1, 2, 3, o 4 átomos de C o arilo; a es 0 o 1; b, c, k y l son, independientemente entre sí, 0, 1, 2 o 3; s y t son, independientemente entre sí, 1 o 2; B es -O-C(R11R12)-, -C(R50R51)-O-, -C:::C-, -CR52=CR53-, -C(R13R14)-C(R15R16)-, -NR17-C(R18R19)-, -C(R54R55)-NR56-, -NR20-C(O)- o-C(O)-NR57-; R11; R12, R13, R14, R15, R16, R17, R18, R19, R20, R50, R51, R52, R53, R54, R55, R56 y R57 son, independientemente entre sí, H o alquilo tiene 1, 2, 3, o 4 átomos de C, donde 1, 2, 3, 4, 5, 6, 7, 8 o 9 átomos de H pueden estar sustituidos con átomos de F; D es C(O)OH, C(O)NHR21 o C(=NR58)NHR22; R21 y R22 son, independientemente entre sí, H, -SO2-alquilo que tiene 1, 2, 3, o 4 átomos de C, -SO2-arilo, -C(O)-alquilo donde el alquilo tiene 1, 2, 3, o 4 átomos de C, -C(O)-arilo, -C(O)OR23, -C(O)NR24R25 o -CN; R23 es alquilo que tiene 1, 2, 3, o 4 átomos de C o arilo; R24 y R25 son, independientemente entre sí, H, alquilo que tiene 1, 2, 3, o 4 átomos de C o arilo; R58 es H, OH, CN, alquilo que tiene 1, 2, 3, o 4 átomos de C o alcoxi que tiene 1, 2, 3, o 4 átomos de C o arilo; R1 y R2 son, independientemente entre sí, alquilo que tiene 1, 2, 3, 4, 5 o 6 átomos de C, donde los radicales alquilo están sin sustituir o sustituidos con 1, 2 o 3 radicales seleccionados entre el grupo que consiste en F, Cl, Br, I, -SH, -S-alquilo tiene 1, 2, 3, o 4 átomos de C, -C(O)OH, -C(O)NH2, NH2, -NH-C(=NH)NH2 o -Om-(CH2)n-R26; m es 0 o 1; n es 0, 1 2 o 3; R26 es H, arilo o heteroarilo, donde el radical arilo o heteroarilo está no sustituido o sustituido con F, Cl, Br, I, OH o alquilo que tiene 1, 2, 3 o 4 átomos de C; o R1 y R2 forman, junto con el átomo de C al que están unidos, un anillo de C de 3, 4, 5 o 6 miembros, donde el anillo de C formado puede condensarse a un radical arilo o heteroarilo; donde el anillo de C formado y el radical arilo o heteroarilo condensado pueden estar sin sustituir o sustituidos con 1, 2 o 3 radicales seleccionados entre el grupo que consiste en F, Cl, Br, I o alquilo tiene 1, 2, 3, o 4 átomos de C; y/o una sal farmacéuticamente aceptable y/o un profármaco del mismo.
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