HRP20090439T1 - Supstituirani derivati propenil piperazina kao novi inhibitori histonske deacetilaze - Google Patents

Supstituirani derivati propenil piperazina kao novi inhibitori histonske deacetilaze Download PDF

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HRP20090439T1
HRP20090439T1 HR20090439T HRP20090439T HRP20090439T1 HR P20090439 T1 HRP20090439 T1 HR P20090439T1 HR 20090439 T HR20090439 T HR 20090439T HR P20090439 T HRP20090439 T HR P20090439T HR P20090439 T1 HRP20090439 T1 HR P20090439T1
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6alkyl
hydrogen
independently selected
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phenyl
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F.A. Van Brandt Sven
Van Emelen Kristof
R. Angibaud Patrick
F.B. Marconnet-Decrane Laurence
Arts Janine
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    • C07—ORGANIC CHEMISTRY
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    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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    • A—HUMAN NECESSITIES
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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
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Abstract

Spoj formule (I), N-oksidnog oblika, njegove farmaceutski prihvatljive adicijske soli i njegovi stereokemijski izomerni oblici, naznačen time, dasvaki X je nezavisno N ili CH; R1 je fenil, naftalenil ili heterociklil; gdjesvaki od navedenih fenila ili naftalenila je ponekad supstituiran sa jednim ili dva supstituenta svaki nezavisno izabran među halo, C1-6alkila, C1-6alkiloksi, polihaloC1-6alkila, arila, hidroksi, cijano, amino, C1-6alkilkarbonilamino, C1-6alkilsulfonilamino, hidroksikarbonila, C1-6alkiloksikarbonila, hidroksiC1-6alkila, C1-6alkiloksimetila, aminometila, C1-6alkilaminometila, C1-6alkilkarbonilaminometila, C1-6alkilsulfonilaminometila, aminosulfonila, C1-6alkilaminosulfonila ili heterociklila; R2 je vodik, -CH2-R5, trifulorometil, -C(=O)-R6 ili -CH2-NR7R8; gdje svaki R5 je nezavisno izabran iz vodika, hidroksi, C1-6alkoksi, C1-6alkiloksiC1-6alkiloksi, C1-6alkilkarboniloksi, piperazinila, N-metilpiperazinila, morfolinila, tiomorfolinila, imidazolila ili triazolila; svaki R6 je nezavisno izabran među hidroksi, C1-6alkiloksi, amino ili mono- ili di(C1-6alkil)amino, C1-6cikloalkilamino, hidroksiC1-6alkilamino, piperazinila, mono- ili di(C1-6alkil)aminoC1-6alkilamino N-metilpiperazinila, morfolinila ili tiomorfolinila; svaki R7 i R8 su nezavisno izabrani među vodika, C1-6alkila, C1-6alkilkarbonila, C1-6alkilsulfonila ili mono- ili di(C1-4alkil)aminosulfonila; R3 je vodik, hidroksimetil, aminometil ili mono- ili di(C1-6alkil)aminometil; R4 je vodik ili C1-6alkil; aril u gore navedenom je fenil ili naftalenil; gdjesvaki navedeni fenil ili naftalenil je ponekad supstituiran sa jednim ili dva supstituenta svaki neovisno izabran među halo, C1-6alkila, C1-6alkoksi, trifluorometila, cijano ili hidroksikarbonila; igore navedeni heterociklil je furanil, tienil, pirolil, pirolinil, pirolidinil, dioksolil, oksazolil, tiazolil, imidazolil, imidazolidinil, pirazolil, pirazolinil, pirazolidinil, izoksazolil, izotiazolil, oksadiazolil, triazolil, tiadiazolil, piranil, piridinil, piperidinil, dioksanil, morfolinil, ditianil, tiomorfolinil, piradizinil, pirimidinil, pirazinil, piperazinil, triazinil, tritianil, indolizinil, indolil, indolinil, benzofuranil, benzotifenil, indazolil, benzimidazolil, bentatiazolil, purinil, kinolizinil, kinolinil, cinolinil, ftlazinil, kinazolinil, kinoksalinil ili naftiridinil; gdjesvaki navedeni heterocikal je ponekad supstituiran sa jednim ili više supstituenata, te je svaki nezavisno izabran među halo, C1-6alkila, C1-6alkoksi, C1-6alkiloksi, cijano, amino, mono- ili di(C1-4alkil)amino. Patent sadrži još 11 patentnih zahtjeva.

Claims (12)

1. Spoj formule (I), [image] N-oksidnog oblika, njegove farmaceutski prihvatljive adicijske soli i njegovi stereokemijski izomerni oblici, naznačen time, da svaki X je nezavisno N ili CH; R1 je fenil, naftalenil ili heterociklil; gdje svaki od navedenih fenila ili naftalenila je ponekad supstituiran sa jednim ili dva supstituenta svaki nezavisno izabran među halo, C1-6alkila, C1-6alkiloksi, polihaloC1-6alkila, arila, hidroksi, cijano, amino, C1-6alkilkarbonilamino, C1-6alkilsulfonilamino, hidroksikarbonila, C1-6alkiloksikarbonila, hidroksiC1-6alkila, C1-6alkiloksimetila, aminometila, C1-6alkilaminometila, C1-6alkilkarbonilaminometila, C1-6alkilsulfonilaminometila, aminosulfonila, C1-6alkilaminosulfonila ili heterociklila; R2 je vodik, -CH2-R5, trifulorometil, -C(=O)-R6 ili –CH2-NR7R8; gdje svaki R5 je nezavisno izabran iz vodika, hidroksi, C1-6alkoksi, C1-6alkiloksiC1-6alkiloksi, C1-6alkilkarboniloksi, piperazinila, N-metilpiperazinila, morfolinila, tiomorfolinila, imidazolila ili triazolila; svaki R6 je nezavisno izabran među hidroksi, C1-6alkiloksi, amino ili mono- ili di(C1-6alkil)amino, C1-6cikloalkilamino, hidroksiC1-6alkilamino, piperazinila, mono- ili di(C1-6alkil)aminoC1-6alkilamino N-metilpiperazinila, morfolinila ili tiomorfolinila; svaki R7 i R8 su nezavisno izabrani među vodika, C1-6alkila, C1-6alkilkarbonila, C1-6alkilsulfonila ili mono- ili di(C1-4alkil)aminosulfonila; R3 je vodik, hidroksimetil, aminometil ili mono- ili di(C1-6alkil)aminometil; R4 je vodik ili C1-6alkil; aril u gore navedenom je fenil ili naftalenil; gdje svaki navedeni fenil ili naftalenil je ponekad supstituiran sa jednim ili dva supstituenta svaki neovisno izabran među halo, C1-6alkila, C1-6alkoksi, trifluorometila, cijano ili hidroksikarbonila; i gore navedeni heterociklil je furanil, tienil, pirolil, pirolinil, pirolidinil, dioksolil, oksazolil, tiazolil, imidazolil, imidazolidinil, pirazolil, pirazolinil, pirazolidinil, izoksazolil, izotiazolil, oksadiazolil, triazolil, tiadiazolil, piranil, piridinil, piperidinil, dioksanil, morfolinil, ditianil, tiomorfolinil, piradizinil, pirimidinil, pirazinil, piperazinil, triazinil, tritianil, indolizinil, indolil, indolinil, benzofuranil, benzotifenil, indazolil, benzimidazolil, bentatiazolil, purinil, kinolizinil, kinolinil, cinolinil, ftlazinil, kinazolinil, kinoksalinil ili naftiridinil; gdje svaki navedeni heterocikal je ponekad supstituiran sa jednim ili više supstituenata, te je svaki nezavisno izabran među halo, C1-6alkila, C1-6alkoksi, C1-6alkiloksi, cijano, amino, mono- ili di(C1-4alkil)amino.
2. Spoj prema patentnom zahtjevu 1, naznačen time, da svaki X je N; R1 je fenil ili fenil ponekad supstituiran sa halo, C1-6alkil, C1-6alikloksi, polihaloC1-6alkil ili aril; R2 je –CH2-R5 ili –C(=O)-R6; svaki R5 je nezavisno izabran iz vodika, hidroksi, C1-6alkiloksi, C1-6alkiloksiC1-6alkiloksi, C1-6alkilkarboniloksi, N-metilpiperazinila, morfolinila ili imidazolila; svaki R6 je nezavisno izabran iz C1-6alkilamino, C1-6cikloalkilamino, hidroskiC1-6alkilamino, di(C1-6alkil)aminoC1-6alkilamino ili morfolinila; R3 je vodik i R4 je vodik ili C1-6alkil.
3. Spoj prema patentnim zahtjevima1 i 2, naznačen time, da svaki X je N; R1 je fenil ili fenil ponekad supstituiran sa halo; R2 je –CH2-R5; svaki R5 je nezavisno izabran iz vodika, hidroksi, C1-6alkiloksi ili C1-6alkilkarboniloksi; R3 je vodik i R4 je vodik.
4. Spoj prema patentnim zahtjevima 1, 2 i 3, naznačen time, da navedeni spoj je spoj br. 1, spoj br. 8, spoj br. 11, spoj br. 9, spoj br. 33, spoj br. 34, spoj br. 7 ili spoj br. 25. [image]
5. Farmaceutski pripravak, naznačen time, da obuhvaća farmaceutski prihvatljive nosače i kao aktivni sastojak terapeutski učinkovitu količinu spoja prema zahtjevima od 1 do 4.
6. Proces pripremanja farmaceutskog pripravka prema zahtjevu 5, naznačen time, da su farmaceutski prihvatljivi nosači i spoj prema zahtjevima od 1 do 4 dobro izmiješani.
7. Spoj prema bilo kojem od zahtjeva od 1 do 4, naznačen time, da se upotrebljava kao lijek.
8. Upotreba spoja prema bilo kojem od zahtjeva od 1 do 4, naznačena time, da se koristi u proizvodnji lijeka za tretman proliferativnih bolesti.
9. Kombinacija, naznačena time, da sadrži anti-tumorski agens i inhibitor HDAC prema zahtjevima od 1 do 4.
10. Proces za pripremu spoja prema zahtjevu 1, naznačen time, da intermedijer sa formulom (II) reagira sa odgovarajućom kiselinom, a to dovodi do nastanka hidroksamske kiseline sa formulom (I). [image]
11. Spoj sa formulom (V) [image] N-oksidnog oblika, njegove farmaceutski prihvatljive adicijske soli i njegovi stereokemijski izomerni oblici, naznačen time, da svaki X je nezavisno N ili CH; R1 je fenil, naftalenil ili heterociklil; gdje svaki navedeni fenil ili naftalenil je ponekad supstituiran sa jednim ili dva supstituenta svaki nezavisno izabran iz halo, C1-6alkila, C1-6alkiloksi, polihaloC1-6alkila, arila, hidroksi, cijano, amino, C1-6alkilkarbonilamino, C1-6alkilsulfonilamino, hidroksikarbonila, C1-6alkiloksikarbonila, hidroksiC1-6alkila, C1-6alkiloksimetila, aminometila, C1-6alkilaminometila, C1-6alkilkarbonilaminometila, C1-6alkilsulfonilaminometila, aminosulfonila, C1-6alkilaminosulfonila ili heterociklila; R2 je vodik, -CH2-R5, trifluorometil, -C(=O)-R6 ili –CH2-NR7R8; gdje svaki R5 je nezavisno izabran iz vodika, hidroksi, C1-6alkiloksi, C1-6alkiloksiC1-6alkiloksi, C1-6alkilkarboniloksi, piperazinila, N-metilpiperazinila, morfolinila, tiomorfolinila, imidazolila ili triazolila; svaki R6 je nezavisno izabran iz vodika, C1-6alkiloksi, amino ili mono- ili di(C1-6alkil)amino, C1-6cikloalkilamino, hidroksiC1-6alkilamino, piperazinila, mono- ili di(C1-6alkil)aminoC1-6alkilamino N-metilpiperazinila, morfolinila ili tiomorfolinila; svaki od R7 i R8 je nezavisno izabran od vodika, C1-6alkila, C1-6alkilkarbonila, C1-6alkilsulfonila ili mono- ili di(C1-4alkil)aminosulfonila; R3 je vodik, hidroksimetil, aminometil ili mono- ili di(C1-6alkil)aminometil; R4 je vodik ili C1-6alkil; gore navedeni aril je fenil ili naftalenil; gdje svaki navedeni fenil ili naftalenil je ponekad supstituiran sa jednim ili dva supstituenta svaki nezavisno izabran iz halo, C1-6alkila, C1-6alkiloksi, trifluorometila, cijano ili hidroksikarbonila; i gore navedeni heterociklil je furanil, pirolil, pirolinil, pirolidinil, dioksolil, oksazolil, tiazolil, imidazolil, imidazolinil, imidazolidinil, pirazolil, pirazolinil, pirazolidinil, izoksazolil, izotiazolil, oksadiazolil, triazolil, tiadiazolil, piranil, piridinil, piperidinil, dioksanil, morfolinil, diatianil, tiomorfolinil, piridazinil, pirimidinil, pirazinil, piperazinil, tiazinil, tritianil, indolizinil, indolil, indolinil, benzofuranil, benzotiofenil, imidazolil, benzoimidazolil, benztiazolil, purinil, kinolizinil, kinolinil, cinolinil, ftlazinil, kinazolil, kinaksolinil ili naftiridinil; gdje svaki navedeni heterocikal ponekad je supstituiran sa jednim ili dva supstituenta svaki nezavisno izabran iz halo, C1-6alkila, C1-6alkiloksi, cijano, amino ili mono- di(C1-4alkil)amino.
12. Proces za pripremanje spoja prema zahtjevu 11, naznačen time, da obuhvaća a) pretvorbu spoja sa formulom (V), gdje R2 je –CH2OH i R4 je vodik, ovdje označenih kao spojevi sa formulom (V-a), u spojeve sa formulom (V) gdje R2 je različit od –CH2OH, ovdje označenog kao spoja (V-b), preko reakcije koja je poznata u stanju tehnike ili transformiranja funkcionalnih grupa, i [image] b) pripremanje spoja sa formulom (V-a) u jednom koraku uz pomoć reakcije intermedijera sa formulom (VI) sa 1,4-dioksan-2,5-diolom te odgovarajućom boronskom kiselinom (VII), gdje R1 je definiran ranije ili [image] c) pripremanje spoja sa formulom (V-b) uz pomoć reakcije intermedijera sa formulom (VI) sa odgovarajućim ketonom sa formulom (VIII), gdje R1 i R2 su definirani ranije [image] d) pripremanje spoja sa formulom (V), gdje R2 je –COOH ovdje označen kao spojevi sa formulom (V-c) u jednom koraku uz pomoć reakcije intermedijera sa formulom (VI) sa 2-okso-propanskom kiselinom i odgovarajućom boronskom kiselinom sa formulom (VII), gdje R1 je definiran ranije, u odgovarajućem otapalu uz dodatnu pretvorbu u intermedijere sa formulom (V) gdje R2 je –C(=O)-R6, preko reakcija koje su poznate u stanju tehnike ili transformiranjem funkcionalnih grupa [image]
HR20090439T 2004-07-28 2009-08-13 Supstituirani derivati propenil piperazina kao novi inhibitori histonske deacetilaze HRP20090439T1 (hr)

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WO2003076438A1 (en) 2002-03-13 2003-09-18 Janssen Pharmaceutica N.V. Piperazinyl-, piperidinyl- and morpholinyl-derivatives as novel inhibitors of histone deacetylase
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