DK2935269T3 - Terapeutisk aktive pyrazolo-pyrimidin derivater. - Google Patents
Terapeutisk aktive pyrazolo-pyrimidin derivater. Download PDFInfo
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- DK2935269T3 DK2935269T3 DK13814962.0T DK13814962T DK2935269T3 DK 2935269 T3 DK2935269 T3 DK 2935269T3 DK 13814962 T DK13814962 T DK 13814962T DK 2935269 T3 DK2935269 T3 DK 2935269T3
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Claims (13)
1. Forbindelse ifølge formel (IA) eller et farmaceutisk acceptabelt salt eller solvat deraf:
hvor Q repræsenterer en gruppe ifølge formel (Qa), (Qb), (Qc), (Qd) eller (Qe):
hvor stjernen (*) repræsenterer punktet for fastgørelse til resten af molekylet; V repræsenterer -CH2-, -C(CH3)2-, -CH2CH2-, -CH2CH2CH2-, -CH2OCH2-, -CH2SCH2-, -CH2S(O)CH2-, -CH2S(O)2CH2- eller -CH2N(R4)CH2-; W repræsenterer resten af en C3-7-cycloalkyl eller C3-7-heterocycloalkylgruppe; Y repræsenterer en linkergruppe valgt blandt -C(O)-, -C(O)N(R4)- og -C(O)C(O)-; Z repræsenterer hydrogen; eller Z repræsenterer Ci-6-alkyl, C2-6-alkenyl, C3-7-cycloalkyl, C3-7-cycloalkyl(Ci-6)alkyl, C3-7-heterocycloalkyl, C3-7-heterocycloalkyl(Ci-6)alkyl, aryl, aryl(Ci-6)alkyl, heteroaryl eller heteroaryl(Ci-6)alkyl, en hvilken som helst af disse grupper kan eventuelt være substitueret med én, to eller tre substituenter uafhængigt af hinanden valgt blandt halogen, cyano, nitro, Ci-6-alkyl, trifluormethyl, cyano(Ci-6)alkyl, (C3-7)heterocycloalkyl, halo(C3-7)-heterocycloalkyl, (Ci-6)alkyl(C3-7)heterocyctoalkyl, (C2- 6) alkoxycarbonyl(C3-7)heterocycloalkyl, dihalo(C3-7)heterocycloalkyl, (C3- 7) heterocycloalkyl(Ci-6)alkyl, (Ci-6)alkyl-(C3-7)heterocycloalkyl(Ci-6)alkyl, heteroaryl, hydroxy, 0x0, Ci-6-alkoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy, (C3- ?)heterocycloalkoxy, (C2-6)alkoxycarbonyl(C3-7)-heterocycloalkoxy, (C3- 7)heterocycloalkyl(Ci-6)alkoxy, aryloxy, haloaryloxy, (Ci-6)-alkoxyaryloxy, Ci-3-alkylendioxy, dihalo(Ci-3)alkylendioxy, arylcarbonyloxy, C1-6 alkylthio, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, amino, Ci-6-alkylamino, di(Ci-6)alkylamino, di(Ci-6)alkylamino(Ci-6)alkyl, arylamino, C2-6 alkylcarbonylamino, C2-6-alkoxycarbonylamino, Ci-6-alkylsulfonylamino, formyl, C2-6-alkylcarbonyl, C3-6-cycloalkylcarbonyl, C3-6-heterocycloalkylcarbonyl, carboxy, C2-6-alkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, Ci-6-alkylaminocarbonyl, di(Ci-6)alkylaminocarbonyl, aminosulfonyl, Ci-6-alkylaminosulfonyl og di(Ci-6)alkylaminosulfonyl; A1 repræsenterer hydrogen, cyano eller trifluormethyl; eller A1 repræsenterer C1-6-alkyl, eventuelt substitueret med én eller flere substituenter uafhængigt af hinanden valgt blandt fluor, -ORa, trifluoromethoxy, -NRbRc, -CChR0 og -CONRbRc; eller A1 repræsenterer C3-7-cycloalkyl; A2 repræsenterer hydrogen eller Ci-6-alkyl; R12 repræsenterer hydrogen, trifluormethyl eller C1-6 alkyl; R13 repræsenterer hydrogen eller Ci-6-alkyl; R4 repræsenterer hydrogen; eller R4 repræsenterer Ci-6-alkyl, eventuelt substitueret med én eller flere substituenter uafhængigt af hinanden valgt blandt -ORa og -NRbRc; Ra repræsenterer hydrogen; eller Ra repræsenterer Ci-6-alkyl, aryl, aryl(Ci-6)alkyl, heteroaryl eller heteroaryl(Ci-6)alkyl, en hvilken som helst af disse grupper kan eventuelt være substitueret med én eller flere substituenter; Rb og Rc uafhængigt af hinanden repræsenterer hydrogen eller trifluormethyl; eller Ci-6-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl(Ci-6)alkyl, aryl, aryl(Ci-6)alkyl, C3-7-heterocycloalkyl, C3-7-heterocycloalkyl(Ci-6)alkyl, heteroaryl eller heteroaryl(Ci-6)alkyl, en hvilken som helst af disse grupper kan eventuelt være substitueret med én eller flere substituenter; eller Rb og Rc, sammen med nitrogenatomet som de begge er bundet til, repræsenterer azetidin-l-yl, pyrrolidin-l-yl, oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl, isothiazolidin-2-yl, piperidin-l-yl, morpholin-4-yl, thiomorpholin-4-yl, piperazin-l-yl, homopiperidin-l-yl, homomorpholin-4-yl eller homopiperazin-l-yl, en hvilken som helst af disse grupper kan eventuelt være substitueret med én eller flere substituenter; og Rd repræsenterer hydrogen; eller Ci-6-alkyl, C3-7-cycloalkyl, aryl, C3-7-heterocycloalkyl eller heteroaryl, en hvilken som helst af disse grupper kan være eventuelt substitueret med én eller flere substituenter; og de eventuelle substituenter på Ra, Rb, Rc eller Rd, eller på den heterocykliske del -NRbRc, er uafhængigt af hinanden valgt blandt halogen, Ci-6-alkyl, Ci-6-alkoxy, difluoromethoxy, trifluoromethoxy, Ci-6-alkoxy(Ci-6)alkyl, Ci-6-alkylthio, Ci-6-alkylsulphinyl, Ci-6-alkylsulphonyl, hydroxy, hydroxy(Ci-6)alkyl, amino(Ci-6)alkyl, cyano, trifluormethyl, oxo, C2-6-alkylcarbonyl, carboxy, C2-6-alkoxycarbonyl, C2-6-alkylcarbonyloxy, amino, C1-6-alkylamino, di(Ci-6)alkylamino, phenylamino, pyridinylamino, C2-6-alkylcarbonylamino, C2-6- alkylcarbonylamino(Ci-6)alkyl, C2-6-alkoxycarbonylamino, Ci-6-alkylsulphonylamino, aminocarbonyl, Ci-6-alkylaminocarbonyl og di(Ci-6)alkylaminocarbonyl.
2. Forbindelse ifølge krav 1, hvor Q repræsenterer en gruppe ifølge formel (Qa-1), (Qa-2) eller (Qa-3):
hvor stjernen (*) repræsenterer punktet for fastgørelse til resten af molekylet; og Y, Z, A1 og A2 er som defineret ifølge krav 1.
3. Forbindelse ifølge krav 1 eller krav 2 repræsenteret ved formel (IIA) eller et farmaceutisk acceptabelt salt eller solvat deraf:
hvor A11 repræsenterer hydrogen, cyano, Ci-6-alkyl, trifluormethyl, -CH2CF3, -CFkOR3, -CH2CH2ORa, -CH2CO2Rd, -CH2CONRbRc eller C3-7-cycloalkyl; og Z, R12, R13, Ra, Rb, Rc og Rd er som defineret ifølge krav 1.
4. Forbindelse ifølge krav 1 eller krav 2 repræsenteret ved formel (IIB) eller et farmaceutisk acceptabelt salt eller solvat deraf: hvor Z, R12 og R13 er som defineret ifølge krav 1; og A11 er ifølge krav 3.
5. Forbindelse ifølge krav 3 eller krav 4, hvor A11 repræsenterer methyl, ethyl, hydroxymethyl eller hydroxyethyl.
6. Forbindelse ifølge et hvilket som helst af de foregående krav, hvor Z repræsenterer C3-7-cycloalkyl, C3-7-heterocycloalkyl, aryl eller heteroaryl, en hvilken som helst af disse grupper kan eventuelt være substitueret med én, to eller tre substituenter uafhængigt af hinanden valgt blandt halogen, cyano, Ci-6-alkyl, trifluormethyl, (C3-7)heterocycloalkyl, dihalo(C3-7)-heterocycloalkyl, hydroxy, 0x0, Ci-6-alkoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy, Ci-6-alkylsulfonyl, Ci-6-alkylamino og di(Ci-6)alkylamino.
7. Forbindelse ifølge krav 6, hvor Z repræsenterer (methoxy)(methyl)-phenyl, (methyl)(trifluormethoxy)phenyl, (methoxy) (methyl)pyridinyl, (ethyl)-(methoxy)pyridinyl, (ethoxy)(methyl)pyridinyl eller dimethoxypyridinyl.
8. Forbindelse ifølge et hvilket som helst af de foregående krav, hvor R12 repræsenterer hydrogen eller methyl.
9. Forbindelse ifølge et hvilket som helst af de foregående krav, hvor R13 repræsenterer hydrogen eller methyl.
10. Forbindelse ifølge krav 1 valgt blandt det følgende: 6-amino-4-{4-[(4-methoxy-2-methylphenyl)carbamyl]piperazin-l-yl}-l/7- pyrazolo[3,4-t/] pyrimidin; 6-amino-4-{4-[(4-methoxyphenyl)carbamyl]piperazin-l-yl}-l/7-pyrazolo[3,4-t/]- pyrimdin; 6-amino-4-{4-[(4-methoxy-2-methylphenyl)carbamyl]-2-(6)-methylpiperazin-l-yl}- l/7-pyrazolo[3,4-d]pyrimidin; 6-amino-4-{4-[(4-methoxyphenyl)carbamyl]-2-(S)-methylpiperazin-l-yl}-l/7-pyrazolo-[3,4-t/] pyrimidin; 6-amino-4-{4-[(4-methoxy-2-methylphenyl)carbamyl]-2-(S)-methylpiperazin-l-yl}-l-methylpyrazolo[3,4-t/] pyrimidin;
6-amino4-{4-[(4-methoxyphenyl)carbamyl]-2-(S)-methylpiperazin-l-yl}-l-methyl- pyrazolo[3,4-d]pyridin; 6-amino-4-[4-indan-5-ylcarbamyl)-2-(S)-methylpiperazin-l-yl]-l- methylpyrazolo[3,4-t/]pyrimidin; 6-amino-4-(4-{[4-dimethylamino)phenyl]carbamyl}-2-(S)-methylpiperazin-l-yl)-l- methylpyrazolo[3,4-t/]pyrimidin; (3S)-4-(6-amino-l,3-dimethylpyrazolo)[3,4-t/]pyrimidin-4-yl)-/V-[6-(3,3- difluorazetidin-l-yl)-2-methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l,3-dimethylpyrazolo)[3,4-t/]pyrimidin-4-yl)-/V-(4-methoxy-2-methyl-phenyl)-3-methylpiperazin-l-carboxamid; (3S)-4(6-amino-l,3-dimethylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-methoxy-2- methyl-pyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3R)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-(3,3-difluorazetidin- l-yl)-2-methylpyridin-3-yl]-3-(hydroxymethyl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-(3,3)-difluorazetidin- l-yl)-2-methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-methoxy-2- methylpyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3R)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(4-methoxy-2- methylphenyl)-3-methylpiperazin-l-carboxamid; (3S)-4-[6-amino-l-methyl-3-(trifluormethyl)pyrazolo[3,4-t/]pyrimidin-4-yl]-/V-[6- (3,3-difluorazetidin-l-yl)-2-methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-[6-amino-l-methyl-3-trifluormethyl)pyrazolo[3,4-t/]pyrimidin-4-yl]-/V-(6- methoxy-2-methylpyridin-3-yl)-3methylpiperazin-l-carboxamid; (3S)-4-[6-amino-l-methyl-3-(trifluormethyl)pyrazolo[3,4-t/]pyrimidin-4-yl]-/V-(4- methoxy-2-methylphenyl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(2,l,3-benzothiadiazol- 4- yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(l/-/-indazol-7-yl)-3- methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(2,l,3-benzothiadiazol- 5- yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(l/-/-indol-7-yl)-3- methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(l/-/-indol-4-yl)-3- methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(2-methyl-l/-/- benzimidazol-4-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-methyl-/V-(l- methylindazol-7-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-methyl-/V-(4-methyl-l/-/- indazol-7-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-hydroxy-2- methylpyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-methyl-/V-[2-methyl- 6(2,2,2-trifluormethoxy)pyridin-3-yl]piperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(l,2-dimethyl-6- oxopyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-methyl-/V-[2-methyl-6- (methylamino)pyridin-3-yl]piperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[2-(3,3-difluorazetidin- l-yl)-4-methylpyrimidin-5-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[4-(difluoromethoxy)-2- methylphenyl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[2-(dimethylamino)-4- methylpyrimidin-5-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-(azetidin-l-yl)-2- methyl-pyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-(3,3-difluorazetidin- l-yl)-4-methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-(dimethylamino)-2- methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-(dimethylamino)-4- methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-(azetidin-l-yl)-2- methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-(dimethylamino)-4- methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-dimethylamino)-2- methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(4-methoxyphenyl)-3- methylpiperazin-l-carboxamid; [(3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-methylpiperazin-l-yl] (2,3-dihydrobenzofuran-2-yl)methanon; l-[(3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-methylpiperazin-l- yl]-2-phenylethan-l,2-dion; [(3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-methylpiperazin-l-yl] (5-methoxybenzofuran-2-yl)methanon; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-methyl-/V-[2-methyl-4- (trifluormethoxy)phenyl]piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[2-fluor-4- (trifluormethoxy)phenyl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[2-chlor-4- (trifluormethoxy)phenyl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[3-methoxy-5- (trifluormethyl)phenyl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(l-ethyl-l/-/-indazol- 3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6- (difluoromethoxy)-2-methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-ethoxy-5-fluor- pyridin-3-yl)-3-methylpiperidin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(2-chlor-4-fluor-5- methylphenyl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(5-fluor-6-methoxy- pyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-ethoxy-2-methyl- pyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-methyl-/V-[l-methyl-5-(trifluormethyl)-l/-/-indazol-3-yl]piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-fluor-l-methyl- l/-/-indazol-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(5-fluor-l-methyl- l/-/-indazol-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(imidazo[l,2- a]pyrimidin-8-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-methyl-/V-(5-methyl-l,2-oxazol-3-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-methyl-/V-(l-methyl-l/-/-indazol-3-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-cyano-2-methyl- pyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-methyl-/V-[2-methyl-4-(methylsulfonyl)phenyl]piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6- (difluoromethoxy)-4-methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-methoxy-5- methyl-pyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-methoxy-4- methyl-pyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(5-methoxy-2- methylphenyl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(3-c/?/or-4- methylphenyl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(2,5-t//c/7/orphenyl)- 3-methylperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(4-cyano-2- methylphenyl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-(6-methoxy-2- methylpyridin-3-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-ethoxy-2- methylpyridin-3-yl)-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(2,6-dimethoxypyridin- 3-yl)-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-(4-methoxy-2- methylphenyl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-(3,3-difluorazetidin- l-yl)-2-methylpyridin-3-yl]-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methylpyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-[2-methyl-4- (trifluooemethoxy)phenyl]piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-(4-methoxy- 3-methylphenyl)piperazin-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(l,2-benzoxazol-3- yl)-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-(l-methyl- l/-/-indazol-3-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V[6- (difluoromethoxy)-4-methylpyridin-3-yl]-3-ethylpiperazin-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-(6-methoxy- 5-methylpyridin-3-)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[2-methyl-4- (methylsulfonyl)phenyl]piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-(6- methoxy)-4-methylpyridin-3-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-[l-methyl- 5-(trifluormethyl)l/-/-/'ndazol-3-yl]piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpyriiTiidin-4-yl)-3-ethyl-/V-(6-fluor-l-methyl - ndazol-3-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"^]pyrimidin-4-yl)-3-ethyl-/V-(5-fluor-l- methyl-l/-/-indazol-3-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-[6- (difluoromethoxy)-2-methylpyridin-3-yl]-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-3-ethyl-/V- (imidazo[l,2-a]-pyridin-8-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-(6-ethoxy-5-fluor- pyridin-3-yl)-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-(2-chlor-4-fluor-5- methylphenyl)-3-ethylpiperazin-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-3-ethyl-/V-(5-fluor-6- methoxypyridin-3-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpyrimidin-4-yl)-/V-(6-cyano-2- methylpyridin-3-yl)-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-(4-cyano-2- methylphenyl)-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-[4- (difluoromethoxy)-2-methylphenyl]-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-[5-(dimethylamino)- 3-methylpyrazin-2-yl]-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-3-ethyl-/V-(l-methyl- l/-/-indazol-4-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-(2-methoxy-6- methylpyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-3-ethyl-/V-(l-methyl- l/-/-indol-4-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-3-ethyl-/V-l(l-methyl- l/-/-benzotriazol-4-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-(imidazo[l,2- a]pyridin-5-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-(imidazo[l,2- a]pyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-3-ethyl-/V-(l-methyl- l/-/-pyrazolo[4,3-c]pyridin-4-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-(3-choro-5- methoxypyridin-2-yl)-3-methylpiperazin-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4"CGpynmidin-4-yl)-/V-(2-chlor-4- methoxyphenyl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6-methoxy-2- (trifluormethyl)pyridin-3-yl]-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-fluor-l-methyl- l/-/-indazol-4-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(2-ethyl-6- methoxypyridin-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[5-(dimethylamino)- 3- methylpyrazin-2-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-(l-methyl- l/-/-pyrazolo[4,3-c]pyridin-4-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(2-cloro-4- methoxyphenyl)-3-ethylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-(6-fluor-l-methyl-l/-/-indazol-4-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-[6-methoxy- 2-(trifluormethyl)pyridin-3-yl]piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-ethyl-/V-(2-ethyl-6- methoxypyridin-3-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[2-(dimethylamino)- 4- methylpyrimidin-5-yl]3-methylpiperazin-l-carboxamid; 4-(6-amino-l-methylpyrazolo-[3,4-t/]-pyrimidin-4-yl)-3-(2-hydroxyethyl)-/V-[2-methyl-4-trifluormethoxy)phenyl]carboxamid; (3R)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3-(hydroxymethyl)-/V- [2-methyl-4-(trifluormethoxy)phenyl]piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-methoxy-2- methyl-pyridin-3-yl)-3-(propan-2-yl)piperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-methoxy-2- methyl-pyridin-3-yl)-3(2-methylpropyl)piperazin-l-carboxamid; 4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-methoxy-2- methylpyridin-3-yl)-3-(2,2,2-trifluorethyl)piperazin-l-carboxamid; 4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(imidazo[l,2-a]pyridin-8- yl)-3-(2,2,2-trifluorethyl)piperazin-l-carboxamid; (35.55) 4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(l-ethyl-l/-/-indazol-3-yl)-3,5-dimethylpiperazin-carboxamid; (35.55) 4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3,5-dimethyl-/V-(l-methyl-l/-/-indazol-3-yl)piperazin-l-carboxamid; (35.55) 4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[5-(dimethylamino)-3-methylpyrazin-2-yl]-3,5-dimethylpiperazin-l-carboxamid; (35.55) 4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(imidazo[l,2-3]-pyridin-8-yl)-3,5-dimethylpiperazin-l-carboxamid; (35.55) 4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-3,5-dimethyl-/V-[2-methyl-4-(trifluormethoxy)phenyl]piperazin-l-carboxamid; (35.55) 4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-methoxy-2-methylpyridin-3-yl)-3,5-dimethylpiperazin-l-carboxamid; 4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-methoxy-2- methylpyridin-3-yl)-3(trifluormethyl)piperazin-l-carboxamid; 4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(4-methoxy-2- methylphenyl)-3(trifluorethyl)piperazin-l-carboxamid; (3S)-4-(6-amino-l,3-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(6-fluor-l-methyl- l/-/-indazol-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-(5-fluor-l-methyl- l/-/-indazol-3-yl)-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[6- (difluoromethoxy)-2-methylpyridin-3-yl]-3-methylpiperazin-l-carboxamid; (3S)-4-(6-amino-l-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[5-(dimethylamino)- 3-methylpyrazin-2-yl]-3-methylpiperazin-l-carboxamid; og (3S)-4-(6-amino-l,3-methyl-l/-/-pyrazolo[3,4-t/]pyrimidin-4-yl)-/V-[4- (difluoromethoxy)-2-methylphenyl]-3-methylpiperazin-l-carboxamid
11. Forbindelse ifølge formel (IA) ifølge krav 1, eller et farmaceutisk acceptabelt salt eller solvat deraf, til anvendelse i terapi.
12. Forbindelse ifølge formel (IA) ifølge krav 1, eller et farmaceutisk acceptabelt salt eller solvat deraf, til anvendelse i behandlingen og/eller forebyggelsen af et inflammatorisk, autoimmun eller onkologisk lidelse; en viral sygdom eller malaria; eller organ- eller celletransplantatafstødning.
13. Farmaceutisk sammensætning omfattende en forbindelse ifølge formel (IA) ifølge krav 1, eller et farmaceutisk acceptabelt salt eller solvat deraf, i forbindelse med et farmaceutisk acceptabelt bærestof.
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| DE1110649B (de) * | 1957-11-22 | 1961-07-13 | Ciba Geigy | Verfahren zur Herstellung von 1-Isopropyl-pyrazolo[3, 4-d]pyrimidinen |
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