HRP20150450T1 - Spojevi aril triazola sa antitumorskom aktivnošä†u - Google Patents

Spojevi aril triazola sa antitumorskom aktivnošä†u Download PDF

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HRP20150450T1
HRP20150450T1 HRP20150450TT HRP20150450T HRP20150450T1 HR P20150450 T1 HRP20150450 T1 HR P20150450T1 HR P20150450T T HRP20150450T T HR P20150450TT HR P20150450 T HRP20150450 T HR P20150450T HR P20150450 T1 HRP20150450 T1 HR P20150450T1
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phenyl
isopropyl
dihydroxy
ylmethyl
triazole
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Giuseppe Giannini
Walter Cabri
Loredana Vesci
Maria Luisa CERVONI
Claudio Pisano
Maurizio Taddei
Serena FERRINI
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Sigma-Tau Research Switzerland S.A.
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Claims (12)

1. Spoj koji ima opću formulu I [image] gdje, R1 je H, CONR4R5; R5 je H, (C1-C6)-alkil ili (C3-C10)-cikloalkil, pri čemu je svaki izborno supstituiran jednom ili više puta sa OH, OMe, Cl, F; R4 je H, (C1-C4)-alkil ili CH(R11)COR12; ili R4 i R5 uzeti zajedno sa atomom dušika za koji su vezani formiraju tro- do sedmo-člani heterociklus koji izborno sadrži dodatni heteroatom izabran iz grupe koju čine N, O ili S; i gdje je navedeni heterociklus izborno supstituiran jednom ili više puta sa OH, OMe, (C1-C4)-alkilom, izborno supstituiranim fenilom ili benzilom; R11 je bočni lanac prirodne α-aminokiseline; R12 je OH, amino, alkilamino ili dialkilamino; R2 je veza, -NH(CO)-, -N(R7)- ili -N(R7)CH2-; R7 je H, (C1-C4)-alkil ili CO2R8; R8 je (C1-C4)-alkil ili benzil; endociklični simboli [image] su, za svaki pojedinačni spoj, sve dvogube veze ili sve jednogube veze; m je cijeli broj sadržan između 0 i 3; R9 i R10 su međusobno nezavisno (C1-C4)-alkil izborno supstituiran sa OH, cikloalkilom, heterocikloalkilom, OMe, amino, (C1-C6)-alkilamino ili (C1-C6)-dialkilamino; heterocikloalkil izborno supstituiran jednom ili više puta sa alkil, amino, (C1-C6)-alkilamino ili (C1-C6)-dialkilamino; cikloalkil; ili R9 i R10 uzeti zajedno sa atomom dušika za koji su vezani formiraju heterociklični prsten izabran iz grupe koju čine piperidil, pirolidinil, piperazinil ili morfolinil, pri čemu je svaki od njih izborno supstituiran jednom ili više puta sa F, Cl, Br, OH, OMe, amino, (C1-C6)-alkilamino, (C1-C6)-dialkilamino, (C1-C4)-alkil, hidroksialkilom, izborno supstituiranim fenilom ili benzilom; ili imidazol nezasićeni heterociklus; R3 je Cl, Et ili i-Pr; njegovi tautomeri, geometrijski izomeri, njihovi optički aktivni oblici kao što su enantiomeri, diastereomeri i njihovi racematni oblici, kao i njihove farmaceutski prihvatljive soli.
2. Spoj prema patentnom zahtjevu 1, gdje R1 je CONR4R5.
3. Spoj prema patentnom zahtjevu 1 koji je izabran iz grupe koju čine 4-izopropil-6-[5-(4-(morfolin-4-ilmetil-fenil)-[1,2,3]-triazol-1-il)benzen-1,3-diol; 4-{5-[4-(3-hidroksi-piperidin-1-ilmetil)-fenil]-[1,2,3]triazol-1-il}-6-izopropil-benzen-1,3-diol; 4-{5-[4-(4-benzil-piperazin-1-ilmetil)-fenil]-[1,2,3]triazol-1-il}-6-izopropil-benzen-1,3-diol; 4-izopropil-6-{5-[4-(4-fenil-piperazin-1-ilmetil)-fenil]-[1,2,3]triazol-1-il}-benzen-1,3-diol; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid (R,S)-1-(2,4-dihidroksi-5-izopropil-fenil)-5-[4-(3-hidroksi-piperidin-1-ilmetil)-fenil]-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-{[etil-(2-hidroksi-etil)-amino]-metil}-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-{4-[2-(2-hidroksi-etil)-piperidin-1-ilmetil]-fenil}-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-piperidin-1-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 5-(4-dietilaminometil-fenil)-1-(2,4-dihidroksi-5-izopropil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropilfenil)-5-[4-(4-metil-piperazin-1-ilmetil)-fenil]-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-piperazin-1-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-[4-(4-dimetilamino-piperidin-1-ilmetil)-fenil]-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-{4-[(2-morphohn-4-il-etilamino)-metil]-fenil}-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 5-{4-[(cikloheksilmetil-amino)-metil]-fenil}-1-(2,4-dihidroksi-5-izopropil-fenil)-1H-1,2,3]triazol-4-karboksilne kiseline; etilamid 5-(4-cikloheksilaminometil-fenil)-1-(2,4-dihidroksi-5-izopropil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 5-{4-[(2-Dietilamino-etilamino)-metil]-fenil}-1-(2,4-dihidroksi-5-izopropil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 5-{4-[(3-dietilamino-propilamino)-metil]-fenil}-1-(2,4-dihidroksi-5-izopropil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-{4-[(1-metil-piperidin-4-ilamino)-metil]-fenil}-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-[4-((S)-3-dimetilaminopirolidin-1-ilmetil)-fenil]-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-pirolidin-1-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-imidazol-1-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; 4-izopropil-6-[5-(4-morfolin-4-il-fenilamino)-[1,2,3]triazol-1-il]-benzen-1,3-diol; 4-izopropil-6-[5-(4-morfolin-4-il-benzilamino)-[1,2,3]triazol-1-il]-benzen-1,3-diol; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-il-fenilamino)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-il-benzilamino)-1H-[1,2,3]triazol-4-karboksilne kiseline; heksilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; ciklopentilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; cikloheksilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; [1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-ilmetil-fenil)-1H-[1,2,3]triazol-4-il]-morfolin-4-il-metanon; (S)-2-{[1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-ilmetil-fenil)-1H-[1,2,3]triazol-4-karbonil]-amino}-3-metil-maslačna kiselina; 4-izopropil-6-[5-(4-pirolidin-1-ilmetil-fenil)-[1,2,3]triazol-1-il]-benzen-1,3-diol; 4-izopropil-6-[5-(4-izoksazolidin-2-ilmetil-fenil)-[1,2,3]triazol-1-il]-benzen-1,3-diol; etilamid 1-(2,4-dihidroksi-5-izopropilfenil)-5-(4-izoksazolidin-2-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-[4-(4-fenil-piperazin-1-ilmetil)-fenil]-1H-[1,2,3]triazol-4-karboksilne kiseline; 4-[5-(4-{[Etil-(2-hidroksi-etil)-amino]-metil}-fenil)-[1,2,3]triazol-1-il]-6-izopropil-benzen-1,3-diol; 4-(5-{4-[2-(2-Hidroksi-etil)-piperidin-1-ilmetil]-fenil}-[1,2,3]triazol-1-il)-6-izopropil-benzen-1,3-diol; 4-izopropil-6-[5-(4-piperidin-1-ilmetil-fenil)-[1,2,3]triazol-1-il]-benzen-1,3-diol; 4-[5-(4-dietilaminometil-fenil)-[1,2,3]triazol-1-il]-6-izopropil-benzen-l,3-diol; N-[3-(2,4-dihidroksi-5-izopropil-fenil)-3H-[1,2,3]triazol-4-il]-4-morfolin-4-il-benzamid; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-il-benzoilamino)-1H-[1,2,3]triazol-4-karboksilne kiseline; N-[3-(2,4-dihidroksi-5-izopropil-fenil)-3H-[1,2,3]triazol-4-il]-4-piperidin-1-il-benzamid; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-piperidin-1-il-benzoilamino)-1H-[1,2,3]triazol-4-karboksilne kiseline; N-[3-(2,4-dihidroksi-5-izopropilfenil)-3H-[1,2,3]triazol-4-il]-4-(3-hidroksi-piperidin-1-il)-benzamid; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-[4-(3-hidroksi-piperidin-1-il)-benzoilamino]-1H-[1,2,3]triazol-4-karboksilne kiseline; N-[3-(2,4-dihidroksi-5-izopropil-fenil)-3H-[1,2,3]triazol-4-il]-4-morfolin-4-ilmetil-benzamid; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-ilmetil-benzoilamino)-1H-[1,2,3]triazol-4-karboksilne kiseline; [3-(2,4-dihidroksi-5-izopropil-fenil)-3H-[1,2,3]triazol-4-il]-amid 4-morfolin-4-ilmetil-cikloheksankarboksilne kiseline; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-[(4-morfolin-4-ilmetil-cikloheksankarbonil)-amino]-1H-[1,2,3]triazol-4-karboksilne kiseline; 4-izopropil-6-{5-[4-(4-metil-piperazin-1-ilmetil)-fenil]-[1,2,3]triazol-1-il}-benzen-1,3-diol; 4-izopropil-6-[5-(4-morfolin-4-ilmetilfenil)-[1,2,3]triazol-1-il]-benzen-1,3-diol; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-morfolin-4-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; etilamid 5-[4-(4-benzil-piperazin-1-ilmetil)-fenil]-1-(2,4-dihidroksi-5-izopropil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline; N-[3-(2,4-dihidroksi-5-izopropil-fenil)-3H-[1,2,3]triazol-4-il]-4-pirolidin-1-il-benzamid; etilamid 1-(2,4-dihidroksi-5-izopropil-fenil)-5-(4-pirolidin-1-il-benzoilamino)-1H-[1,2,3]triazol-4-karboksilne kiseline i (2-hloro-etil)-amid 1-(2,4-dihidroksi-5-izopropilfenil)-5-(4-morfolin-4-ilmetil-fenil)-1H-[1,2,3]triazol-4-karboksilne kiseline.
4. Spoj prema bilo kojem od patentnih zahtjeva 1-3 za uporabu kao lijek.
5. Spoj prema patentnom zahtjevu 4, gdje je lijek koristan za tretman patološkog stanja za koje bi modulacija aktivnosti Hsp90 rezultirala u poboljšanju zdravlja pacijenta.
6. Spoj prema patentnom zahtjevu 5 gdje je patološko stanje neurodegenerativna bolest, inflamatorna bolest, bolest kancer, autoimuna bolest, cerebralna iskemija ili parazitemija uključujući malariju.
7. Spoj prema patentnom zahtjevu 6, pri čemu, neurodegenerativna bolest je Parkinsonova bolest, Hantingtonova bolest, Alzheimerova bolest, demencija sa Luisovim tijelima, amiotrofna lateralna skleroza, spinalna i bulbarna muskularna atrofija ili spinocerebelarna ataksija.
8. Spoj prema patentnom zahtjevu 6, pri čemu, bolest kancer je kancer dojke, pankreasa, pluća, pleure, debelog crijeva, peritoneuma, kože, lica i vrata, bubrega, bešike, mozga, prostate, grlića materice, jajnika, očiju i bolest kancer je leukemija ili metastatski kancer.
9. Farmaceutska kompozicija koja sadrži najmanje jedan spoj prema patentnim zahtjevima 1-3 kao aktivni sastojak u smjesama sa najmanje jednim farmaceutski prihvatljivim prenositeljem i/ili ekscipientom.
10. Postupak za sintezu spoja formule I gdje R1 je -CONR4R5, R2 je veza, i m = 1, koji sadrži reakciju spoja formule II [image] gdje R3 je kao što je definiran u patentnom zahtjevu 1, sa spojem formule III [image] u polarnom aprotonskom otapalu u neutralnoj atmosferi i u prisustvu katalizatora na bazi rutenija.
11. Postupak za sintetiziranje spoja formule I gdje R1 je CONR4R5, R2 je -N(R7)- ili -N(R7)CH2-, koji sadrži reakciju spoja formule II kao što je definirano u patentnom zahtjevu 10, sa spojem formule IV [image] Formula IV gdje R9 i R10 imaju značenje definirano u patentnom zahtjevu 1 i R2 je -N(R7)- ili -N(R7)CH2-, u polarnom aprotonskom otapalu u neutralnoj atmosferi i u prisustvu katalizatora na bazi rutenija.
12. Postupak za pripremu farmaceutske kompozicije prema patentnom zahtjevu 9, koji sadrži miješanje najmanje jednog spoja prema patentnim zahtjevima 1-3 sa najmanje jednim farmaceutski prihvatljivim prenositeljem i/ili ekscipientom.
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