HRP20120327T1 - Supstituirani indolil alkil amino derivati kao novi inhibitori histonske deacetilaze - Google Patents

Supstituirani indolil alkil amino derivati kao novi inhibitori histonske deacetilaze Download PDF

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HRP20120327T1
HRP20120327T1 HRP20120327TT HRP20120327T HRP20120327T1 HR P20120327 T1 HRP20120327 T1 HR P20120327T1 HR P20120327T T HRP20120327T T HR P20120327TT HR P20120327 T HRP20120327 T HR P20120327T HR P20120327 T1 HRP20120327 T1 HR P20120327T1
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Gustaaf Celine Verdonck Marc
Ren� Angibaud Patrick
Roux Bruno
No�lle Constance Pilatte Isabelle
Ten Holte Peter
Arts Janine
Van Emelen Kristof
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Janssen Pharmaceutica Nv
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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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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    • A61P35/02—Antineoplastic agents specific for leukemia
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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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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Abstract

Spoj formule (I), njegovi N-oksidni oblici, farmaceutski prihvatljive adicijske soli i stereokemijski izomerni oblici, naznačen time dasvaki n je cijeli broj sa vrijednosti 0, 1 ili 2 i kada n je 0 tada je namjeravana direktna veza; svaki m je cijeli broj sa vrijednosti 1 ili 2; svaki X je nezavisno N ili CH; svaki Y je nezavisno O, S, ili NR4; pri čemusvaki R4 je vodik, C1-6alkil, C1-6alkiloksiC1-6alkil, C3-6cikloalkil, C3-6cikloalkilmetil, fenilC1-6alkil, -C(=O)-CHR5R6 ili -S(=O)2-N(CH3)2; pri čemusvaki R5 i R6 je nezavisno vodik, amino, C1-6alkil ili aminoC1-6alkil; ikada Y je NR4 i R2 je na 7-položaju indolila tada R2 i R4 zajedno mogu formirati dvovalentni radikal -(CH2)2- (a-1), ili -(CH2)3- (a-2); R1 je vodik, C1-6alkil, hidroksiC1-6alkil, C1-6alkilsulfonil, C1-6alkilkarbonil ili mono- ili di(C1-6alkil)aminosulfonil; R2 je vodik, hidroksi, amino, halo, C1-6alkil, cijano, C2-6alkenil, polihaloC1-6alkil, nitro, fenil, C1-6alkilkarbonil, hidroksikarbonil, C1-6alkilkarbonilamino, C1-6alkiloksi, ili mono- ili di(C1-6alkil)amino; R3 je vodik, C1-6alkil, ili C1-6alkiloksi; tekada su R2 i R3 na susjednim atomima ugljika, oni mogu formirati dvovalentni radikal -O-CH2-O-.Patent sadrži još 11 patentnih zahtjeva.

Claims (12)

1. Spoj formule (I), [image] njegovi N-oksidni oblici, farmaceutski prihvatljive adicijske soli i stereokemijski izomerni oblici, naznačen time da svaki n je cijeli broj sa vrijednosti 0, 1 ili 2 i kada n je 0 tada je namjeravana direktna veza; svaki m je cijeli broj sa vrijednosti 1 ili 2; svaki X je nezavisno N ili CH; svaki Y je nezavisno O, S, ili NR4; pri čemu svaki R4 je vodik, C1-6alkil, C1-6alkiloksiC1-6alkil, C3-6cikloalkil, C3-6cikloalkilmetil, fenilC1-6alkil, -C(=O)-CHR5R6 ili -S(=O)2-N(CH3)2; pri čemu svaki R5 i R6 je nezavisno vodik, amino, C1-6alkil ili aminoC1-6alkil; i kada Y je NR4 i R2 je na 7-položaju indolila tada R2 i R4 zajedno mogu formirati dvovalentni radikal -(CH2)2- (a-1), ili -(CH2)3- (a-2); R1 je vodik, C1-6alkil, hidroksiC1-6alkil, C1-6alkilsulfonil, C1-6alkilkarbonil ili mono- ili di(C1-6alkil)aminosulfonil; R2 je vodik, hidroksi, amino, halo, C1-6alkil, cijano, C2-6alkenil, polihaloC1-6alkil, nitro, fenil, C1-6alkilkarbonil, hidroksikarbonil, C1-6alkilkarbonilamino, C1-6alkiloksi, ili mono- ili di(C1-6alkil)amino; R3 je vodik, C1-6alkil, ili C1-6alkiloksi; te kada su R2 i R3 na susjednim atomima ugljika, oni mogu formirati dvovalentni radikal -O-CH2-O-.
2. Spoj prema zahtjevu 1 naznačen time da svaki n je cijeli broj sa vrijednosti 0 ili 1; svaki R4 je vodik, C1-6alkil, C1-6alkiloksiC1-6alkil, C3-6cikloalkil ili fenilC1-6alkil; R1 je vodik, C1-6alkil, hidroksiC1-6alkil, C1-6alkilkarbonil ili C1-6alkilsulfonil; te R2 je vodik, halo, C1-6alkil, cijano, nitro, polihaloC1-6alkil ili C1-6alkiloksi.
3. Spoj prema zahtjevu 1 i 2 naznačen time da gdje svaki n je cijeli broj sa vrijednosti 1; svaki m je cijeli broj sa vrijednosti 1; svaki X je nezavisno N; svaki Y je nezavisno NR4; svaki R4 je C1-6alkil; R1 je vodik; R2 je vodik ili halo; te R3 je vodik.
4. Spoj prema zahtjevu 1, 2 i 3 naznačen time da navedeni spoj je spoj br.1a, spoj br.30, spoj br.39 i spoj br.50. [image]
5. Farmaceutski pripravak naznačen time da sadrži farmaceutski prihvatljive nosače i kao aktivni sastojak terapeutski učinkovitu količinu spoja prema zahtjevu 1 do 4.
6. Postupak za dobivanje farmaceutskog pripravka prema zahtjevu 5 naznačen time da su blisko pomiješani farmaceutski prihvatljivi nosači i spoj prema zahtjevu 1 do 4.
7. Spoj prema bilo kojem od zahtjeva 1 do 4 naznačen time da je za uporabu kao lijek.
8. Uporaba spoja prema bilo kojem od zahtjeva 1 do 4 naznačena time da je za proizvodnju lijeka za liječenje proliferativnih bolesti.
9. Kombinacija naznačena time da sadrži anti-kancerozno sredstvo i HDAC inhibitor prema bilo kojem od zahtjeva 1 do 4.
10. Postupak za dobivanje spoja prema zahtjevu 1, naznačen time da sadrži a) reakciju intermedijera formule (II), pri čemu Q je tetrahidropiraniloksiaminokarbonil, ovdje se naziva kao intermedijer formule (II-a), sa odgovarajućom kiselinom, kao što je na primjer, trifluoro octena kiselina, koja dovodi do hidroksamske kiseline sa formulom (I). [image] b) reakciju intermedijera formule (II), pri čemu Q je C1-2alkiloksikarbonil, ovdje se naziva kao intermedijeri formule (II-c), sa hidroksilaminom, u prisutnosti baze i u odgovarajućem otapalu uz dobivanje hidroksamske kiseline sa formulom (I) [image]
11. Spoj formule (II), [image] njegovi N-oksidni oblici, farmaceutski prihvatljive adicijske soli i stereokemijski izomerni oblici, naznačen time da je svaki n je cijeli broj sa vrijednosti 0, 1 ili 2 i kada n je 0 tada je namjeravana direktna veza; svaki m je cijeli broj sa vrijednosti 1 ili 2; svaki X je nezavisno N ili CH; svaki Y je nezavisno O, S, ili NR4; pri čemu svaki R4 je vodik, C1-6alkil, C1-6alkiloksiC1-6alkil, C3-6cikloalkil, C3-6cikloalkilmetil, fenilC1-6alkil, -C(=O)-CHR5R6 ili -S(=O)2-N(CH3)2; pri čemu svaki R5 i R6 je nezavisno vodik, amino, C1-6alkil ili aminoC1-6alkil; i kada Y je NR4 i R2 je na 7-položaju indolila tada R2 i R4 zajedno mogu formirati dvovalentni radikal -(CH2)2- (a-1), ili -(CH2)3- (a-2); R1 je vodik, C1-6alkil, hidroksiC1-6alkil, C1-6alkilsulfonil, C1-6alkilkarbonil ili mono- ili di(C1-6alkil)aminosulfonil; R2 je vodik, hidroksi, amino, halo, C1-6alkil, cijano, C2-6alkenil, polihaloC1-6alkil, nitro, fenil, C1-6alkilkarbonil, hidroksikarbonil, C1-6alkilkarbonilamino, C1-6alkiloksi ili mono- ili di(C1-6alkil)amino; R3 je vodik, C1-6alkil, ili C1-6alkiloksi; kada su R2 i R3 na susjednim atomima ugljika, oni mogu formirati dvovalentni radikal -O-CH2-O-; i Q je C1-2alkiloksikarbonil, hidroksikarbonil ili tetrahidropiraniloksiaminokarbonil.
12. Postupak za dobivanje spoja prema zahtjevu 11, naznačen time da sadrži a) reakciju spoja formule (II), pri čemu Q je hidroksikarbonil, ovdje se naziva spojevi formule (II-b), sa intermedijerom formule (III) u prisutnosti odgovarajućih reagensa kao što su N'-(etilkarbonimidoil)-N,N-dimetil-1,3-propandiamin, monohidroklorid (EDC) i 1-hidroksi-1H-benzotriazol (HOBT) sa formiranjem spoja formule (II-a), [image] b) reakciju intermedijera formule (VI) sa odgovarajućim karboksaldehidom formule (V), pri čemu t je cijeli broj sa vrijednosti 0 ili 1, te kada t je 0 tada je namjeravana direktna veza, u prisutnosti odgovarajućeg reagensa, uz formiranje spoja formule (II-a), [image] c) reakciju spoja formule (II), pri čemu Q je metil- ili etiloksikarbonil (C1-2alkil), ovdje se naziva spojevi formule (II-c), sa odgovarajućom kiselom otopinom ili bazičnom otopinom, što rezultira formiranjem spoja formule (II-b), [image] d) reakciju etil estera karboksilne kiseline formule (IV) sa odgovarajućim karboksaldehidom formule (V), u prisutnosti odgovarajućeg reagensa, uz formiranje spoja formule (II-c), [image] e) reakciju intermedijera formule (XIV) sa odgovarajućim intermedijerom formule (XV), u prisutnosti odgovarajućeg reagensa, u pogodnom otapalu, uz formiranje spoja formule (II-c), [image] f) reakciju intermedijera formule (X) sa intermedijerom formule (XI) pri čemu W je odgovarajuća odlazna skupina kao, na primjer, halo, npr. fluoro, kloro, bromo ili jodo, ili sulfoniloksi radikal kao metilsulfoniloksi, uz formiranje spoja formule (II-c), ili [image] g) reakciju intermedijera formule (XII) sa intermedijerom formule (XIII), pri čemu W je odgovarajuća odlazna skupina kako je gore opisano, uz formiranje spoja formule (II-c). [image]
HRP20120327TT 2004-07-28 2012-04-13 Supstituirani indolil alkil amino derivati kao novi inhibitori histonske deacetilaze HRP20120327T1 (hr)

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PCT/EP2005/053612 WO2006010750A1 (en) 2004-07-28 2005-07-25 Substituted indolyl alkyl amino derivatives as novel inhibitors of histone deacetylase

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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
ATE396971T1 (de) 2002-03-13 2008-06-15 Janssen Pharmaceutica Nv Sulfonylaminoderivate als neue inhibitoren von histondeacetylase
WO2003075929A1 (en) 2002-03-13 2003-09-18 Janssen Pharmaceutica N.V. Inhibitors of histone deacetylase
MY147767A (en) 2004-06-16 2013-01-31 Janssen Pharmaceutica Nv Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders
EA010652B1 (ru) 2004-07-28 2008-10-30 Янссен Фармацевтика Н.В. Замещенные индолильные алкиламинопроизводные в качестве новых ингибиторов гистондеацетилазы
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