HRP20170456T1 - Novi kondenzirani derivati pirimidina, namijenjeni inhibiranju aktivnosti tirozinske kinaze - Google Patents

Novi kondenzirani derivati pirimidina, namijenjeni inhibiranju aktivnosti tirozinske kinaze Download PDF

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Publication number
HRP20170456T1
HRP20170456T1 HRP20170456TT HRP20170456T HRP20170456T1 HR P20170456 T1 HRP20170456 T1 HR P20170456T1 HR P20170456T T HRP20170456T T HR P20170456TT HR P20170456 T HRP20170456 T HR P20170456T HR P20170456 T1 HRP20170456 T1 HR P20170456T1
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Croatia
Prior art keywords
6alkyl
image
phenyl
heterocyclic
amino
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HRP20170456TT
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English (en)
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Mi Young Cha
Seok Jong Kang
Mi Ra Kim
Ju Yeon Lee
Ji Young Jeon
Myoung Gi Jo
Eun Joo Kwak
Kwang Ok Lee
Tae Hee Ha
Kwee Hyun Suh
Maeng Sup Kim
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Hanmi Science Co., Ltd.
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Application filed by Hanmi Science Co., Ltd. filed Critical Hanmi Science Co., Ltd.
Publication of HRP20170456T1 publication Critical patent/HRP20170456T1/hr

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    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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    • C07B2200/09—Geometrical isomers

Claims (15)

1. Spoj formule (I), ili njegova farmaceutski prihvatljiva sol: [image] , naznačen time što, W je O; X je O, NH, S, SO ili SO2; Y je atom vodika, atom halogena, C1-6alkil ili C1-6alkoksi; svaki od A i B je neovisno atom vodika, atom halogena ili di(C1-6alkil)aminometil; Z je aril ili heteroaril s jednim ili više supstituenata, koje se bira iz skupine koju čine: atom vodika, atom halogena, hidroksi, nitro, cijano, C1-6alkil, C1-6alkoksi, C1-6alkilkarbonil, C1-6alkoksikarbonil, di(C1-6alkil)aminoC2-6alkoksikarbonil, amino, C1-6alkilamino, di(C1-6alkil)amino, karbamoil, C1-6alkilkarbamoil, di(C1-6alkil)karbamoil, di(C1-6alkil)aminoC2-6alkilkarbamoil, sulfamoil, C1-6alkilsulfamoil, di(C1-6alkil)sulfamoil, di(C1-6alkil)aminoC2-6alkilsulfamoil, C1-6alkilsulfonil, C1-6alkilsulfinil, di(C1-6alkil)fosfonil, hidroksiC1-6alkil, hidroksikarbonilC1-6alkil, C1-6alkoksiC1-6alkil, C1-6alkilsulfonilC1-6alkil, C1-6alkilsulfinilC1-6alkil, di(C1-6alkil)fosfonilC1-6alkil, hidroksiC2-6alkoksi, C1-6alkoksiC2-6alkoksi, aminoC1-6alkil, C1-6alkilaminoC1-6alkil, di(C1-6alkil)aminoC1-6alkil, di(C1-6alkil)aminoacetil, aminoC2-6alkoksi, C1-6alkilaminoC2-6alkoksi, di(C1-6alkil)aminoC2-6alkoksi, hidroksiC2-6alkilamino, C1-6alkoksiC2-6alkilamino, aminoC2-6alkilamino, C1-6alkilaminoC2-6alkilamino, di(C1-6alkil)aminoC2-6alkilamino, heteroaril, heterocikl, heterociklički oksi, heterociklički tio, heterociklički sulfinil, heterociklički sulfonil, heterociklički sulfamoil, heterociklički C1-6alkil, heterociklički C1-6alkoksi, heterociklički amino, heterociklički C1-6alkilamino, heterociklički aminoC1-6alkil, heterociklički karbonil, heterociklički C1-6alkilkarbonil, heterociklički karbonilC1-6alkil, heterociklički C1-6alkiltio, heterociklički C1-6alkilsulfinil, heterociklički C1-6alkilsulfonil, heterociklički aminokarbonil, heterociklički C1-6alkilaminokarbonil, heterociklički aminokarbonilC1-6alkil, heterociklički karboksamido, te heterociklički C1-6alkilkarboksamido; gdje se aril odnosi na C6-12 ciklički ili biciklički aromatski prsten; gdje se svaki od heteroarila neovisno odnosi na 5- do 12-eročlani ciklički ili biciklički aromatski hetero prsten s jednim ili više N, O ili S; gdje se svaki od heterocikla neovisno odnosi na zasićeni ili djelomično nezasićeni 3- do 12-eročlani ciklički ili biciklički hetero prsten s jednim ili više N, O, S, SO ili SO2, u kojem atom ugljika koji tvori heterocikl izborno ima jedan ili više supstituenata, koje se bira iz skupine koju čine C1-6alkil, hidroksi, hidroksiC1-6alkil, hidroksikarbonil, C1-6alkoksi, amino, C1-6alkilamino, di(C1-6alkil)amino, di(C1-6alkil)aminoC1-6alkil, di(C1-6alkil)aminokarbonil, heterocikl, heterociklički C1-6alkil, te heteroaril, te u kojem, uz uvjet da heterocikl izborno sadrži atom dušika, gdje atom dušika izborno nosi supstituent kojeg se bira iz skupine koju čine atom vodika, C1-6alkil, monohalogenoC1-6alkil, dihalogenoC1-6alkil, trihalogenoC1-6alkil, C3-6cikloalkil, hidroksiC2-6alkil, C1-6alkoksiC2-6alkil, C1-6alkilkarbonil, hidroksiC1-6alkilkarbonil, C1-6alkoksikarbonil, karbamoil, C1-6alkilkarbamoil, di(C1-6alkil)karbamoil, sulfamoil, C1-6alkilsulfamoil, di(C1-6alkil)sulfamoil, C1-6alkilsulfonil, aminoC2-6alkil, C1-6alkilaminoC2-6alkil, di(C1-6alkil)aminoC2-6alkil, di(C1-6alkil)aminoC1-6alkilkarbonil, heterocikl, heterociklički oksi, heterociklički tio, heterociklički sulfinil, heterociklički sulfonil, heterociklički C1-6alkil, heterociklički karbonil, heterociklički C1-6alkilkarbonil, heterociklički C1-6alkilsulfinil, te heterociklički C1-6alkilsulfonil (gdje, kada atom dušika tvori tercijarni amin, taj je izborno u obliku N-oksida); i izborno, C1-6alkil je djelomično nezasićen ili ima C3-6cikloalkilni ostatak, a atom ugljika u heterociklu je u obliku karbonila.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što se Z bira iz skupine koju čine formule Z1 do Z203: [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image]
[image] 3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što se spoj formule (I) bira iz skupine koju čine: N-(3-((2-((4-(4-metilpiperazin-1-il)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((4-(4-izopropilpiperazin-1-il)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((4-morfolinofenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((4-((dimetilamino)metil)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((4-((4-(dimetilamino)piperidin-1-il)metil)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((3-fluor-4-(1-metilpiperazin-4-il)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((4-(2-dimetilamino)etil)amino)-3-fluorfenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((3-fluor-4-((1-metilpiperidin-4-il)amino)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-(2-(3-metoksi-4-(4-metil-piperazin-1-il)fenilamino)furo[3,2-d]pirimidin-4-iloksi)fenil)akrilamid; i N-(3-((2-((4-sulfamoilfenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid.
4. Spoj u skladu s patentnim zahtjevom 3, naznačen time što ga se bira iz skupine koju čine: N-(3-((2-((4-(4-izopropilpiperazin-1-il)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((4-morfolinofenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((4-((dimetilamino)metil)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((4-((4-(dimetilamino)piperidin-1-il)metil)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((3-fluor-4-(1-metilpiperazin-4-il)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((4-(2-dimetilamino)etil)amino)-3-fluorfenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-((2-((3-fluor-4-((1-metilpiperidin-4-il)amino)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid; N-(3-(2-(3-metoksi-4-(4-metil-piperazin-1-il)fenilamino)furo[3,2-d]pirimidin-4-iloksi)fenil)akrilamid; i N-(3-((2-((4-sulfamoilfenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid, ili njihove farmaceutski prihvatljive soli.
5. Spoj u skladu s patentnim zahtjevom 3, naznačen time što je spoj N-(3-((2-((4-(4-metilpiperazin-1-il)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid, ili njegova farmaceutski prihvatljiva sol.
6. Spoj u skladu s patentnim zahtjevom 3, naznačen time što je spoj N-(3-((2-((4-(4-metilpiperazin-1-il)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid.
7. Spoj u skladu s patentnim zahtjevom 1, naznačen time što se spoj formule (I) bira iz skupine koju čine: [image] i [image] .
8. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I), ili njegovu farmaceutski prihvatljivu sol, u skladu s patentnim zahtjevima 1 do 7 kao aktivni sastojak.
9. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time što je namijenjen upotrebi u terapiji.
10. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time što je namijenjen upotrebi u sprječavanju ili liječenju raka, tumora, upalnih bolesti, autoimunih bolesti ili imunološki izazvanih bolesti.
11. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 10, naznačen time što su rak ili tumori inducirani tirozinskom kinazom vezanom uz receptor čimbenika rasta epiderme (EGFR) ili njezinim mutantom.
12. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 10, naznačen time što su rak, tumori, upalne bolesti, autoimune bolesti ili imunološki izazvane bolesti su izazvani djelovanjem najmanje jedne kinaze, koju se bira iz skupine koju čine Brutonova tirozinska kinaza (BTK), janus kinaza 3 (JAK3), T-stanična kinaza koja inducira interleukin-2 (ITK), kinaza kod limfocita u mirovanju (RLK), te tirozinska kinaza iz koštane srži (BMX).
13. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 10, naznačen time što su rak, tumori, upalne bolesti, autoimune bolesti ili imunološki izazvane bolesti izazvani abnormalno aktiviranim B-limfocitima, T-limfocitima ili obima.
14. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 10, naznačen time što su upalne bolesti, autoimune bolesti ili imunološki izazvane bolesti artritis, reumatoidni artritis, spondiloartropatija, gihtični artritis, osteoartritis, mladalački artritis, druga artritična stanja, lupus, sistemni eritematozni lupus (SLE), bolesti povezane s kožom, psorijaza, egzem, dermatitis, atopični dermatitis, bol, plućni poremećaj, upala pluća, sindrom dišnog distresa kod odraslih (ARDS), plućna sarkoidoza, kronična plućna upalna bolest, kronična opstruktivna plućna bolest (COPD), kardiovaskularna bolest, arterioskleroza, infarkt miokarda, kongestivna srčana insuficijencija, reperfuzijska ozljeda srca, upalna crijevna bolest, Crohnova bolest, ulcerozni kolitis, sindrom iritabilnih crijeva, astma, Sjogrenov sindrom, autoimuna bolest štitnjače, koprivnjača (knidoza), multipla skleroza, skleroderma, odbacivanje presađenog organa, heteroplastični presadak, idiopatska trombocitopenična purpura (ITP), Parkinsonova bolest, Alzheimerova bolest, bolest povezana s dijabetesom, upala, upalna bolest zdjelice, alergijski rinitis, alergijski bronhitis, alergijski sinusitis, leukemija, limfom, B-stanični limfom, T-stanični limfom, mijelom, akutna limfoidna leukemija (ALL), kronična limfoidna leukemija (CLL), akutna mijeloidna leukemija (AML), kronična mijeloidna leukemija (CML), leukemija vlasastih stanica, Hodgkinova bolest, nehodgkinovski limfom, multipli mijelom, mijelodisplastični sindrom (MDS), mijeloproliferativne novotvorine (MPN), limfom difuznih velikih B-stanica ili folikularni limfom.
15. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 10 u sprječavanju ili liječenju upalnih bolesti, autoimunih bolesti ili imunološki izazvanih bolesti koje se bira između artritisa, reumatoidnog artritisa, spondiloartropatije, gihtičnog artritisa, osteoartritisa, mladalačkog artritisa, drugih artritičnih stanja, lupusa, sistemnog eritematoznog lupusa (SLE), bolesti povezanih s kožom, psorijaze, egzema, dermatitisa, atopičnog dermatitisa, boli, plućnog poremećaja, upale pluća, sindroma dišnog distresa kod odraslih (ARDS), plućne sarkoidoze, kronične plućne upalne bolesti, kronične opstruktivne plućne bolesti (COPD), kardiovaskularne bolesti, arterioskleroze, infarkta miokarda, kongestivne srčane insuficijencije, reperfuzijske ozljede srca, upalne crijevne bolesti, Crohnove bolesti, ulceroznog kolitisa, sindroma iritabilnih crijeva, astme, Sjogrenovog sindroma, autoimune bolesti štitnjače, koprivnjače (knidoze), multiple skleroze, skleroderme, odbacivanja presađenog organa, heteroplastičnog presatka, idiopatske trombocitopenične purpure (ITP), Parkinsonove bolesti, Alzheimerove bolesti, bolesti povezane s dijabetesom, upale, upalne bolesti zdjelice, alergijskog rinitisa, alergijskog bronhitisa, alergijskog sinusitisa, leukemije, limfoma, B-staničnog limfoma, T-staničnog limfoma, mijeloma, akutne limfoidne leukemije (ALL), kronične limfoidne leukemije (CLL), akutne mijeloidne leukemije (AML), kronične mijeloidne leukemije (CML), leukemije vlasastih stanica, Hodgkinove bolest, nehodgkinovskog limfoma, multiplog mijeloma, mijelodisplastičnog sindroma (MDS), mijeloproliferativnih novotvorina (MPN), limfoma difuznih velikih B-stanica ili folikularnog limfoma, naznačen time što je spoj N-(3-((2-((4-(4-metilpiperazin-1-il)fenil)amino)furo[3,2-d]pirimidin-4-il)oksi)fenil)akrilamid, ili njegova farmaceutski prihvatljiva sol.
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