HRP20120105T1 - Aminoheterociklički spojevi - Google Patents

Aminoheterociklički spojevi Download PDF

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HRP20120105T1
HRP20120105T1 HR20120105T HRP20120105T HRP20120105T1 HR P20120105 T1 HRP20120105 T1 HR P20120105T1 HR 20120105 T HR20120105 T HR 20120105T HR P20120105 T HRP20120105 T HR P20120105T HR P20120105 T1 HRP20120105 T1 HR P20120105T1
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methyl
pyrazolo
dihydro
pyrimidin
tetrahydro
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HR20120105T
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Robert Verhoest Patrick
Proulx-Lafrance Caroline
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Pfizer Inc.
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    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • 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

Abstract

Spoj Formule (I), ili njegova farmaceutski prihvatljiva sol, naznačen time što: R se bira iz skupine koju čine (C1-C6)alkil, (C2-C6)alkenil, (C2-C6)alkinil, (C3-C8)cikloalkil, heterocikloalkil, aril, te heteroaril, od kojih svaki može biti izborno supstituiran s jednim do tri supstituenta, gdje se te supstituente neovisno bira iz skupine koju čine (C1-C4)alkil, (C1-C4)alkoksi, halogen, te (C1-C4)halogenalkil; R1 se bira iz skupine koju čine vodik, (C1-C4)alkil, (C2-C4)alkenil, (C2-C4)alkinil, (C1-C4)halogenalkil, te ciklopropil; R2 se bira iz skupine koju čine (C1-C6)alkil, (C2-C6)alkenil, (C2-C6)alkinil, (C1-C6)halogenalkil, heteroaril selected iz skupine koju čine piridinil, piridazinil, pirimidinil, te pirazinil, te ER5, gdje heteroaril može biti izborno supstituiran s jednim do tri supstituenta, koje se neovisno bira iz skupine koju čine (C1-C4)alkil i (C1-C4)

Claims (16)

1. Spoj Formule (I), [image] ili njegova farmaceutski prihvatljiva sol, naznačen time što: R se bira iz skupine koju čine (C1-C6)alkil, (C2-C6)alkenil, (C2-C6)alkinil, (C3-C8)cikloalkil, heterocikloalkil, aril, te heteroaril, od kojih svaki može biti izborno supstituiran s jednim do tri supstituenta, gdje se te supstituente neovisno bira iz skupine koju čine (C1-C4)alkil, (C1-C4)alkoksi, halogen, te (C1-C4)halogenalkil; R1 se bira iz skupine koju čine vodik, (C1-C4)alkil, (C2-C4)alkenil, (C2-C4)alkinil, (C1-C4)halogenalkil, te ciklopropil; R2 se bira iz skupine koju čine (C1-C6)alkil, (C2-C6)alkenil, (C2-C6)alkinil, (C1-C6)halogenalkil, heteroaril selected iz skupine koju čine piridinil, piridazinil, pirimidinil, te pirazinil, te ER5, gdje heteroaril može biti izborno supstituiran s jednim do tri supstituenta, koje se neovisno bira iz skupine koju čine (C1-C4)alkil i (C1-C4)halogenalkil; R3 se bira iz skupine koju čine vodik, (C1-C4)alkil, (C2-C4)alkenil, (C2-C4)alkinil, (C3-C6) cikloalkil, te (C1-C4)halogenalkil; E se bira iz skupine koju čine -CH2-, -CH2CH2-, -CH2CH2CH2-, te -C(O)-; R5 se bira iz skupine koju čine (C3-C8)cikloalkil, heterocikloalkil, aril, ariloksi, te heteroaril, od kojih bilo koji može biti izborno supstituiran s jednim do tri supstituenta, gdje se takve supstituente neovisno bira iz skupine koju čine (C1-C4)alkil, (C2-C4)alkenil, (C2-C4)alkinil, (C1-C4)hidroksialkil, (C1-C4)halogenalkil, (C1-C4)alkoksi, (C1-C4)halogenalkoksi, (C3-C8)cikloalkil, halogen, cijano, fenil, morfolinil, (C1-C4)alkilamino, pirazolil, triazolil, te imidazolil.
2. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što: R se bira iz skupine koju čine etil, izopropil, trifluoretil, ciklobutil, ciklopentil, difluorcikloheksil, metoksifenil, tetrahidro-2H-tiopiran-4-il, te tetrahidro-2H-piran-4-il; R1 je vodik ili metil; R2 je metil, trifluoretil, trifluorbutil, pirimidinil, trifluormetilpirimidinil ili ER5; R3 je metil, etil, izopropil, trifluormetil, trifluoretil ili ciklopropil; E je -CH2- ili -C(O)-; R5 se bira iz skupine koju čine supstituirani ili nesupstituirani ciklopentil, morfolinil, fenil, naftil, benziloksi, pirimidinil, piridinil, kinolinil, kinoksalinil, pirazinil, pirazolil, benzimidazolil, cinolinil, naftidrinil, pirido[2,3-b]pirazinil, imidazo[4,5-c]piridinil, benzotiadiazolil, tetrahidropirazolo[1,5-a]piridinil, dihidrobenzodioksinil, imidazolil, dihidrobenzofuranil, triazolil, oksazolil, izoksazolil, benzodioksinil, tiazolil, imidazo[1,2-a]piridinil, tetrahidrobenzotiazolil, dihidrobenzoksazinil, tetrahidropiranil, tetrahidropirazolo[1,5-a]azepinil, te dihidropirolo[1,2-b]pirazolil.
3. Spoj u skladu s patentnim zahtjevom 2, ili njegova farmaceutski prihvatljiva sol, naznačen time što: R se bira iz skupine koju čine izopropil, ciklobutil, ciklopentil, te tetrahidro-2H-piranil; R1 je vodik; R2 je ER5; R3 je metil ili etil; E je -CH2-; i R5 se bira iz skupine koju čine fenil, pirimidin-2-il, piridin-2-il, pirazin-2-il, te 5-metilpirazin-2-il.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz skupine koju čine: 6-[(3S,4S)1-benzil-4-metilpirolidin-3-il]-1-ciklopentil-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-ciklopentil-6-[(3S,4S)-4-metil-1-(kinoksalin-6-ilmetil)pirolidin-3-il]-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-ciklopentil-6-{(3S,4S)-4-metil-1-[(5-metilpirazin-2-il)metil]pirolidin-3-il}-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-ciklopentil-6-{(3S,4S)-1-[(1,3-dimetil-1H-pirazol)-5-il)metil]-4-metilpirolidin-3-il}-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-ciklopentil-6-[(3S,4S)-4-metil-1-(4,5,6,7-tetrahidropirazolo[1,5-a]piridin-3-ilmetil)pirolidin-3-il]-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-ciklopentil-6-{(3S,4S)-4-metil-1-[(1-metil-1H-benzimidazol-2-il)metil]pirolidin-3-il}-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(cinolin-3-ilmetil)-4-metilpirolidin-3-il]-1-ciklopentil-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-ciklopentil-6-{(3S,4S)-4-metil-1-[(2-metilpirimidin-4-il)metil]pirolidin-3-il}-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; i 1-ciklopentil-6-((3S,4S)-1-{[2-(dimetilamino)pirimidin-4-il]metil}-4-metilpirolidin-3-il]-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; ili njihove farmaceutski prihvatljive soli.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz skupine koju čine: 6-[(3S,4S)-1-benzil-4-etilpirolidin-3-il]-1-izopropil-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-benzil-4-metilpirolidin-3-il]-1-izopropil-1,5-dihidro-4H-pirazoio[3,4-d]pirimidin-4-on; 1-izopropil-6-[(3S,4S)-4-metil-1-(kinoksalin-6-ilmetil)pirolidin-3-il]-1,5-dihyor-4H-pirazolo[3,4-d]pirimidin-4-on; 1-izopropil-6-((3S,4S)-4-metil-1-(kinolin-3-ilmetil)pirolidin-3-il]-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-izopropil-6-[(3S,4S)-4-metil-1-(kinoksalin-6-ilmetil)pirolidin-3-il]-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-izopropil-6-[(3S,4S)-4-metil-1-(kinolin-3-ilmetil)pirolidin-3-il]-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-izopropil-6-{(3S,4S)-4-metil-1-[(2-metilpirimidin-5-il)metil}pirolidin-3-il}-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-izopropil-6-{(3S,4S)-1-[(6-metoksipiridin-3-il)metil]-4-metilpirolidin-3-il}-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-izopropil-6-{(3S,4S)-4-metil-1-[(5-metilpirazin-2-il)metil]pirolidin-3-il}-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-izopropil-6-[(3S,4S)-4-metil-1-(1,5-naftiridin-4-ilmetil)pirolidin-3-il]-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-izopropil-6-[(3S,4S)-4-metil-1-(1,8-naftiridin-4-ilmetil)pirolidin-3-il]-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 1-izopropil-6-[(3S,4S)-4-metil-1-(kinolin-4-ilmetil)pirolidin-3-il]-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; i 1-izopropil-6-[(3S,4S)-4-metil-1-(pirido[2,3-b]pirazin-8-ilmetil)pirolidin-3-il]-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; ili njihove farmaceutski prihvatljive soli.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz skupine koju čine: 6-((3S,4S)-1-benzil-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-4-metil-1-[(2-metilpirimidin-5-il)metil]pirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-4-metil-1-[(5-metilpirazin-2-il)metil]pirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-1-[(6-metoksipiridin-3-il)metil]-4-metilpirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-4-metil-1-(kinolin-3-ilmetil)pirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-4-metil-1-[(2-metilpirimidin-4-il)metil]pirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-((3S,4S)-4-metil-1-[(6-metilpiridin-3-il)metil]pirolidin-3-il)-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-4-metil-1-{[6-(trifluormetil)piridin-3-il]metil}pirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-4-metil-1-[(1-metil-1H-imidazo[4,5-c]piridin-2-il)metil]pirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-1-[(1,3-dimetil-1H-pirazol-5-il)metil]-4-metilpirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(2,1,3-benzotiadiazol-5-ilmetil)-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-4-metil-1-(kinoksalin-2-ilmetil)pirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-4-metil-1-(kinolin-4-ilmetil)pirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-4-metil-1-(piridin-2-ilmetil)pirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-benzil-4-metilpirolidin-3-il]-3-metil-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(3-fluorbenzil)-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(3,5-difluorbenzil)-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-4-metil-1-[4-(trifluormetil)benzil]pirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 3-metil-6-[(3S,4S)-4-metil-1-(piridin-3-ilmetil)pirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 3-metil-6-((3S,4S)-4-metil-1-[(2-metilpirimidin-5-il)metil]pirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-1-[(6-metoksipiridin-3-il)metil]-4-metilpirolidin-3-il}-3-metil-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-((3S,4S)-4-metil-1-((6-metilpiridin-2-il)metil]pirolidin-3-il)-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(4-fluorbenzil)-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-benzil-4-etilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(2-fluorbenzil)-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-4-metil-1-[2-(trifluormetil)benzil]pirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(2,4-difluorbenzil)-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(4-metoksibenzil)-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-benzil-4-metilpirolidin-3-il]-1-(tetrahidro-2H-tiopiran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(2-metoksibenzil)-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(3-metoksibenzil)-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-4-metil-1-[3-(trifluormetil)benzil]pirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-1-(2,6-difluorbenzil)-4-metilpirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-((3S,4S)-4-etil-1-[(5-metilpirazin-2-il)metil]pirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-{(3S,4S)-4-etil-1-[(6-metoksipiridin-3-il)metil]pirolidin-3-il}-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-4-etil-1-(piridin-2-ilmetil)pirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-((3S,4S)-4-etil-1-(kinoksalin-2-ilkarbonil)pirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 6-[(3S,4S)-4-metil-1-(pirimidin-2-ilmetil)pirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on; 2-({(3S,4S)-3-etil-4-[4-okso-1-(tetrahidro-2H-piran-4-il)-4,5-dihidro-1H-pirazolo[3,4-d]pirimidin-6-il]pirolidin-1-il}metil)benzonitril; 3-({(3S,4S)-3-etil-4-[4-okso-1-(tetrahidro-2H-piran-4-il)-4,5-dihidro-1H-pirazolo[3,4-d]pirimidin-6-il]pirolidin-1-il}metil)benzonitril; i 4-({(3S,4S)-3-etil-4-[4-okso-1-(tetrahidro-2H-piran-4-il)-4,5-dihidro-1H-pirazolo[3,4-d]pirimidin-6-il]pirolidin-1-il}metil)benzonitril; ili njihove farmaceutski prihvatljive soli.
7. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 6-[(3S,4S)-4-metil-1-(pirimidin-2-ilmetil)pirolidin-3-il]-1-(tetrahidro-2H-piran-4-il)-1,5-dihidro-4H-pirazolo[3,4-d]pirimidin-4-on, ili njegove farmaceutski prihvatljive soli.
8. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1-7, ili njegovu farmaceutski prihvatljivu sol, i farmaceutski prihvatljiv vehikulum, podlogu ili razrjeđivač.
9. Pripravak u skladu s patentnim zahtjevom 8, naznačen time što dodatno sadrži drugo farmaceutsko sredstvo.
10. Pripravak u skladu s patentnim zahtjevom 9, naznačen time što drugo farmaceutsko sredstvo se bira iz skupine koju čine donepezil, galantamin, memantine, rivastigmin, te takrin.
11. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-7, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u inhibiranju PDE9 kod sisavca kojem je potrebno takvo inhibiranje.
12. Spoj u skladu s bilo kojim u skladu s patentnim zahtjevom 1-7, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u liječenju neurodegenerativne bolesti kod sisavca kojem je potrebno takvo liječenje.
13. Spoj namijenjen upotrebi u liječenju neurodegenerativne bolesti u skladu s patentnim zahtjevom 12, naznačen time što je neurodegenerativna bolest Alzheimerova bolest.
14. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-7, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u poticanju neurorestoracije kod sisavca kojem je potrebna takva neurorestoracija (obnavljanje živčanog tkiva).
15. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-7, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u poboljšavanju kognitivnih poremećaja kod sisavca kojem je potrebno takvo poboljšanje.
16. Spoj namijenjen upotrebi u skladu s bilo kojim od patentnih zahtjeva 11-15, naznačen time što je sisavac čovjek.
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