HRP20120835T1 - (3-aril-piperazin-1-il) derivati 6,7-dialkoksikinazolina, 6,7-dialkoksiftalazina i 6,7-dialkoksiizokinolina - Google Patents

(3-aril-piperazin-1-il) derivati 6,7-dialkoksikinazolina, 6,7-dialkoksiftalazina i 6,7-dialkoksiizokinolina Download PDF

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HRP20120835T1
HRP20120835T1 HRP20120835TT HRP20120835T HRP20120835T1 HR P20120835 T1 HRP20120835 T1 HR P20120835T1 HR P20120835T T HRP20120835T T HR P20120835TT HR P20120835 T HRP20120835 T HR P20120835T HR P20120835 T1 HRP20120835 T1 HR P20120835T1
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piperazin
quinazoline
dimethoxy
alkyl
disorder
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HRP20120835TT
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Jan Kehler
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H. Lundbeck A/S
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Claims (15)

1. Spoj strukture I [image] gdje • Q je NH • A i B se izabiru nezavisno između CH i N uz uvjet da A i B nisu oba N u isto vrijeme • R1 i R2 su nezavisno C1-C4 alkil • R3, R4, R5, R6 i R7 se nezavisno izabiru između: H, (C1-C6) alkil, (C1-C6) alkoksi, halogen, halo(C1-C6)alkil, (C1-C6)hidroksialkil, (C1-C6)alkoksi(C1-C6)alkil, (C3-C6)hidroksicikloalkil, (C3-C8)cikloalkoksi, (C1-C6)alkoksi(C3-C8)cikloalkil, heterocikloalkil, hidroksiheterocikloalkil, i (C1-C6)alkoksi-heterocikloalkil, gdje svaki (C3-C8)cikloalkil ili heterocikloalkil može nezavisno biti supstituiran s jednim do tri (C1-C6)alkil; -NR8R9 skupina, gdje su R8 i R9 nezavisno izabrani između vodika, C1-C6 alkil, halo(C1-C6)alkil, (C3-C8)cikloalkil, heterocikloalkil; 6-7-eročlani alifatski heterocikl: [image] gdje n je 1 ili 2 i Z je kisik ili NR10, gdje R10 je vodik ili (C1-C6) alkil, ili keton, sulfon, ester, amid, sulfonski ester ili sulfonamid, izabran između [image] ili [image] gdje Y je vodik ili (C1-C6) alkil i X je izabran između: • (C1-C6) alkil skupina nesupstituirana ili supstituirana jednim ili više halogena, • -O-(C1-C6) alkil nesupstituiran ili supstituiran jednim ili više halogena, • -NR11R12 skupina, gdje su R11 i R12 nezavisno izabrani između vodika, C1-C6 alkil, halo(C1-C6)alkil, (C3-C8)cikloalkil, heterocikloalkil, ili • 6-7-eročlani alifatski heterocikl: [image] gdje n je 1 ili 2; i W je kisik ili NR13, gdje R13 je vodik ili (C1-C6) alkil, ili ο R4, R5 i R6 su nezavisno nitro, ili ο dva susjedna supstituenta izabrana između R3, R4, R5, R6 i R7 mogu zajedno s atomima ugljika za koji su spojeni formirati 5-7-eročlani, zasićeni ili nezasićeni prsten koji sadrži ugljik i po izboru jedan ili dva heteroatoma izabrana između N, O ili S, i po izboru je supstituiran skupinom (C1-C6) alkoksi. Preostala tri supstituenta izabrana između R3, R4, R5, R6 i R7, koji nisu dio prstena, nezavisno su izabrana kako je gore navedeno ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema zahtjevu 1 gdje A=N i B=CH, ili gdje A=CH i B=CH, ili gdje A=CH i B=N, i gdje su Q, R1, R2, R3, R4, R5, R6 i R7 kako je definirano u Zahtjevu 1.
3. Spoj prema bilo kojem od prethodnih zahtjeva gdje su R1 i R2 nezavisno C1-C2 alkil.
4. Spoj prema bilo kojem od prethodnih zahtjeva gdje je R3 izabran između H, (C1-C6) alkoksi ili halogena.
5. Spoj prema bilo kojem od prethodnih zahtjeva gdje je R4 izabran između H, (C1-C6) alkoksi, halogen ili nitro.
6. Spoj prema bilo kojem od prethodnih zahtjeva gdje je R5 izabran između o vodik, (C1-C6) alkil, (C1-C6) alkoksi, halogen, halo(C1-C6)alkil, nitro, ili o -NR8R9 skupina, gdje su R8 i R9 nezavisno izabrani između vodika, C1-C6 alkil, halo(C1-C6)akil, (C3-C8)cikloalkil, heterocikloalkil, ili o 6-7-eročlani aliftaski heterocikl: [image] - gdje n je 1 ili 2 i Z je kisik ili NR10, gdje je R10 vodik ili (C1-C6) alkil.
7. Spoj prema bilo kojem od prethodnih zahtjeva gdje je R6 izabran između H, (C1-C6) alkoksi, halogen ili nitro.
8. Spoj prema bilo kojem od prethodnih zahtjeva gdje je R7 izabran između H, (C1-C6) alkoksi ili halogen.
9. Spoj prema bilo kojem od prethodnih zahtjeva gdje dva susjedna supstituenta izabrana između R3, R4, R5, R6 i R7 zajedno s atomima ugljika za koji su spojeni formiraju 5-7-eročlani, zasićeni ili nezasićeni prsten koji po izboru sadrži jedan ili dva heteroatoma izabrana između N, O ili S.
10. Spoj prema zahtjevu 1, gdje je spoj izabran između 6,7-Dimetoksi-4-(3-(3-metoksifenil)-piperazin-1-il)-kinazolin; 6,7-Dimetoksi-4-((R)-3-(3-metoksifenil)-piperazin-1-il)-kinazolin; 6,7-Dimetoksi-4-((S)-3-(3-metoksifenil)-piperazin-1-il)-kinazolin; 6,7-Dimetoksi-4-((R)-3-fenilpiperazin-1-il)-kinazolin; 6,7-Dimetoksi-4-((S)-3-fenil-piperazin-1-il)-kinazolin; 4-[3-(3,4,5-trimetoksifenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(2-metoksifenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(4-dimetilaminofenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(3,4-metilendioksifenil)-piperazin-1-il]-6,7-dimetoksikinazolin; 4-[3-(2,5-diklorofenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(4-metilfenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(4-fluorofenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(4-etilfenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(4-metoksifenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(4-klorofenil)-piperazin-1-il]-6,7-dimetoksikinazolin; 4-[3-(3-klorofenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(3-nitrofenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(4-nitrofenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 6,7-Dimetoksi-4-(3-naftalen-2-il-piperazin-1-il)-kinazolin; 6,7-Dimetoksi-4-(3-naftalen-1-il-piperazin-1-il)-kinazolin; 4-[3-(3,5-dimetoksifenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(2,5-dimetoksifenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(4-trifluorometilfenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(2,4-diklorofenil)-piperazin-1-il]-6,7-dimetoksikinazolin; 4-[3-(3-bromofenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; 4-[3-(4-bromofenil)-piperazin-1-il]-6,7-dimetoksikinazolin; 6,7-Dimetoksi-4-(3-(6-metoksi-naftalen-2-il)-piperazin-1-il)-kinazolin; 6,7-Dimetoksi-4-[3-(4-morfolin-4-il-fenil)-piperazin-1-il]-kinazolin; 4-[3-(2,4-dikloro-5-fluorofenil)-piperazin-1-il]-6,7-dimetoksi-kinazolin; ili njegova farmaceutski prihvatljiva sol.
11. Postupak pripreme spojeva Formule I prema zahtjevu 1 koji obuhvaća reakciju spoja Formule II: [image] u kojem je L odlazeća skupina izabrana između Cl, Br, I, OSO2CF3, i A, B, R1 i R2 su kako je definirano u zahtjevu 1; sa spojem Formule III: [image] ili u obliku slobodne baze ili njezine adicijske soli; gdje Q, R3, R4, R5, R6 i R7 su kako je definirano u zahtjevu 1; ili čisto ili u inertnom otapalu ili smjesi otapala, pri temperaturi između 0 do oko , po izboru u prisutnosti baze, po izboru paladij katalizatora, nakon čega slijedi dorada i izolacija proizvoda Formule I, ili u obliku slobodne baze ili njezine kisele adicijske soli.
12. Postupak prema zahtjevu 12 gdje se paladij katalizator formira in situ miješanjem izvora paladija (II) kao što je Pd(OAc)2 ili Pd2(dba)3 s bisfosfin ligandom kao što je BINAP (2,2’-bis(difenilfosfino)-1,1’-binaftil), u reakcijskom otapalu.
13. Farmaceutska smjesa koja sadrži terapijski učinkovitu količinu spoja iz zahtjeva 1 i farmaceutski prihvatljiv nosač ili punilo.
14. Spoj prema bilo kojem od zahtjeva 1 do 11 ili njegova farmaceutski prihvatljiva kisela adicijska sol za uporabu u liječenju neurodegenerativnog ili psihijatrijskog poremećaja, gdje je neurodegenerativni poremećaj izabran iz grupe koja obuhvaća Alzheimerovu bolest, multi-infarktnu demenciju, alkoholnu demenciju ili drugu vrstu demencije povezanu s drogom, demenciju povezanu s intrakranijalnim tumorima ili traumom mozga, demenciju povezanu s Huntingtonovom bolesti ili Parkinsonovom bolesti, ili demenciju povezanu s AIDS-om; amnestički poremećaj; post-traumatski stres poremećaj; mentalnu retardaciju; poremećaj učenja, na primjer poremećaj čitanja, matematički poremećaj ili poremećaj u pisanju; poemećaj nedostatka pažnje/hiperaktivnost; i kognitivno opadanje povezano sa starenjem, i psihijatrijski poremećaj je izabran iz grupe koja obuhvaća shizofreniju, na primjer paranoidnog, dezorganiziranog, katatoničkog, nediferenciranog ili rezidualnog tipa; shizofreniformni poremećaj; shizoafektivni poremećaj, na primjer deluzijskog tipa ili depresivnog tipa; deluzijski poremećaj; psihotični poremećaj induciran supstancama, na primjer alkoholom, amfetaminom, kanabisom, kokainom, halucinogenima, inhalantima, opioidima ili fenciklidinom; poremećaj osobnosti paranoidnog tipa; i poremećaj osobnosti shizoidnog tipa;
15. Spoj prema bilo kojem od zahtjeva 1-11, ili njegova farmaceutski prihvatljiva kisela adicijska sol, za uporabu kao lijek.
HRP20120835TT 2006-07-10 2012-10-16 (3-aril-piperazin-1-il) derivati 6,7-dialkoksikinazolina, 6,7-dialkoksiftalazina i 6,7-dialkoksiizokinolina HRP20120835T1 (hr)

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US81985506P 2006-07-10 2006-07-10
DKPA200600951 2006-07-10
PCT/DK2007/000351 WO2008006372A1 (en) 2006-07-10 2007-07-10 (3-aryl-piperazin-1-yl), (2-aryl-morpholin-4-yl) and (2-aryl- thiomorpholin-4-yl) derivatives of 6,7-dialkoxyquinazoline, 6,7- dialkoxyphtalazine and 6,7-dialkoxyisoquinoline

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US (1) US8492394B2 (hr)
EP (1) EP2057153B1 (hr)
JP (1) JP2009542732A (hr)
CN (1) CN101495476A (hr)
CY (1) CY1113314T1 (hr)
DK (1) DK2057153T3 (hr)
ES (1) ES2392553T3 (hr)
HR (1) HRP20120835T1 (hr)
PL (1) PL2057153T3 (hr)
PT (1) PT2057153E (hr)
RS (1) RS52562B (hr)
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WO (1) WO2008006372A1 (hr)

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US8492394B2 (en) 2013-07-23
RS52562B (en) 2013-04-30
SI2057153T1 (sl) 2012-12-31
EP2057153B1 (en) 2012-09-12
CN101495476A (zh) 2009-07-29
CY1113314T1 (el) 2016-04-13
DK2057153T3 (da) 2012-10-15
US20110098286A1 (en) 2011-04-28
EP2057153A1 (en) 2009-05-13
ES2392553T3 (es) 2012-12-11

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