HRP20230248T1 - Spojevi korisni za liječenje preranog starenja, te naročito progerije - Google Patents
Spojevi korisni za liječenje preranog starenja, te naročito progerije Download PDFInfo
- Publication number
- HRP20230248T1 HRP20230248T1 HRP20230248TT HRP20230248T HRP20230248T1 HR P20230248 T1 HRP20230248 T1 HR P20230248T1 HR P20230248T T HRP20230248T T HR P20230248TT HR P20230248 T HRP20230248 T HR P20230248T HR P20230248 T1 HRP20230248 T1 HR P20230248T1
- Authority
- HR
- Croatia
- Prior art keywords
- group
- amine
- quinolin
- hydrogen atom
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 26
- 206010063493 Premature ageing Diseases 0.000 title claims 5
- 208000032038 Premature aging Diseases 0.000 title claims 5
- 208000025500 Hutchinson-Gilford progeria syndrome Diseases 0.000 title 1
- 208000007932 Progeria Diseases 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 134
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 78
- 125000005843 halogen group Chemical group 0.000 claims 31
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 16
- -1 -COOR1 group Chemical group 0.000 claims 13
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 230000001575 pathological effect Effects 0.000 claims 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- PLFPWCLLFOJLBI-UHFFFAOYSA-N 2-(quinolin-3-ylamino)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(NC=2C=C3C=CC=CC3=NC=2)=C1 PLFPWCLLFOJLBI-UHFFFAOYSA-N 0.000 claims 2
- GKQWGUCKPKFKBV-UHFFFAOYSA-N 2-n-quinolin-3-ylpyridine-2,3-diamine Chemical compound NC1=CC=CN=C1NC1=CN=C(C=CC=C2)C2=C1 GKQWGUCKPKFKBV-UHFFFAOYSA-N 0.000 claims 2
- JKWLLRXHEBZOLZ-UHFFFAOYSA-N 4-methoxy-n-(4-methylpyridin-2-yl)quinolin-7-amine Chemical compound C=1C=C2C(OC)=CC=NC2=CC=1NC1=CC(C)=CC=N1 JKWLLRXHEBZOLZ-UHFFFAOYSA-N 0.000 claims 2
- GAWOGCFTXVIYQT-UHFFFAOYSA-N 4-methoxy-n-pyridin-2-ylquinolin-7-amine Chemical compound C=1C=C2C(OC)=CC=NC2=CC=1NC1=CC=CC=N1 GAWOGCFTXVIYQT-UHFFFAOYSA-N 0.000 claims 2
- NZGKKWIIQVXUKY-UHFFFAOYSA-N 4-methyl-n-pyrimidin-2-ylquinolin-2-amine Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=NC=CC=N1 NZGKKWIIQVXUKY-UHFFFAOYSA-N 0.000 claims 2
- FNRTZPDQMOKWEO-UHFFFAOYSA-N 4-n,4-n-dimethyl-7-n-(4-methylpyridin-2-yl)quinoline-4,7-diamine Chemical compound C=1C=C2C(N(C)C)=CC=NC2=CC=1NC1=CC(C)=CC=N1 FNRTZPDQMOKWEO-UHFFFAOYSA-N 0.000 claims 2
- YKAUOMYYVJQVGG-UHFFFAOYSA-N 6-(quinoxalin-2-ylamino)pyridine-3-carbonitrile Chemical compound N1=CC(C#N)=CC=C1NC1=CN=C(C=CC=C2)C2=N1 YKAUOMYYVJQVGG-UHFFFAOYSA-N 0.000 claims 2
- HPJXFVDJZJVWKH-UHFFFAOYSA-N 6-chloro-n-(4-methylpyridin-2-yl)quinoxalin-2-amine Chemical compound CC1=CC=NC(NC=2N=C3C=CC(Cl)=CC3=NC=2)=C1 HPJXFVDJZJVWKH-UHFFFAOYSA-N 0.000 claims 2
- TVDAFLMOGGSQRO-UHFFFAOYSA-N 8-chloro-n-pyridin-4-ylquinolin-2-amine Chemical compound N1=C2C(Cl)=CC=CC2=CC=C1NC1=CC=NC=C1 TVDAFLMOGGSQRO-UHFFFAOYSA-N 0.000 claims 2
- BYMRPDIGYDXSRD-UHFFFAOYSA-N 8-chloro-n-pyrimidin-2-ylquinolin-2-amine Chemical compound N1=C2C(Cl)=CC=CC2=CC=C1NC1=NC=CC=N1 BYMRPDIGYDXSRD-UHFFFAOYSA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- FJWIHTNNFSITSP-UHFFFAOYSA-N [2-(quinoxalin-2-ylamino)pyridin-4-yl]methanol Chemical compound OCC1=CC=NC(NC=2N=C3C=CC=CC3=NC=2)=C1 FJWIHTNNFSITSP-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- CUOAGPLCYXTZFB-UHFFFAOYSA-N n-(3,5-dichloro-4-methylpyridin-2-yl)quinoxalin-2-amine Chemical compound CC1=C(Cl)C=NC(NC=2N=C3C=CC=CC3=NC=2)=C1Cl CUOAGPLCYXTZFB-UHFFFAOYSA-N 0.000 claims 2
- LSRLBKXWOIDDGO-UHFFFAOYSA-N n-(3-methoxypyridin-2-yl)quinolin-3-amine Chemical compound COC1=CC=CN=C1NC1=CN=C(C=CC=C2)C2=C1 LSRLBKXWOIDDGO-UHFFFAOYSA-N 0.000 claims 2
- MXQIQAXLTPMUGA-UHFFFAOYSA-N n-(3-methoxypyridin-2-yl)quinolin-6-amine Chemical compound COC1=CC=CN=C1NC1=CC=C(N=CC=C2)C2=C1 MXQIQAXLTPMUGA-UHFFFAOYSA-N 0.000 claims 2
- XXDPXWRBTKQMSI-UHFFFAOYSA-N n-(3-nitropyridin-2-yl)quinolin-3-amine Chemical compound [O-][N+](=O)C1=CC=CN=C1NC1=CN=C(C=CC=C2)C2=C1 XXDPXWRBTKQMSI-UHFFFAOYSA-N 0.000 claims 2
- JZVGQBIINWZGJR-UHFFFAOYSA-N n-(4,6-dimethylpyridin-2-yl)quinoxalin-2-amine Chemical compound CC1=CC(C)=NC(NC=2N=C3C=CC=CC3=NC=2)=C1 JZVGQBIINWZGJR-UHFFFAOYSA-N 0.000 claims 2
- JNSCAEPZOZUIHU-UHFFFAOYSA-N n-(4-ethylpyridin-2-yl)quinoxalin-2-amine Chemical compound CCC1=CC=NC(NC=2N=C3C=CC=CC3=NC=2)=C1 JNSCAEPZOZUIHU-UHFFFAOYSA-N 0.000 claims 2
- VXECRKRPJRAULJ-UHFFFAOYSA-N n-(4-methyl-3-nitropyridin-2-yl)quinoxalin-2-amine Chemical compound CC1=CC=NC(NC=2N=C3C=CC=CC3=NC=2)=C1[N+]([O-])=O VXECRKRPJRAULJ-UHFFFAOYSA-N 0.000 claims 2
- FZVLZGBHFVRNLB-UHFFFAOYSA-N n-(4-methyl-5-nitropyridin-2-yl)quinoxalin-2-amine Chemical compound C1=C([N+]([O-])=O)C(C)=CC(NC=2N=C3C=CC=CC3=NC=2)=N1 FZVLZGBHFVRNLB-UHFFFAOYSA-N 0.000 claims 2
- YPHGFGYLPUODNV-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)-3-(trifluoromethyl)quinoxalin-2-amine Chemical compound CC1=CC=NC(NC=2C(=NC3=CC=CC=C3N=2)C(F)(F)F)=C1 YPHGFGYLPUODNV-UHFFFAOYSA-N 0.000 claims 2
- GSPMGXUDYBBILM-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)-4-morpholin-4-ylquinolin-7-amine Chemical compound CC1=CC=NC(NC=2C=C3N=CC=C(C3=CC=2)N2CCOCC2)=C1 GSPMGXUDYBBILM-UHFFFAOYSA-N 0.000 claims 2
- BSHNAVOQNSIGLC-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)quinoxalin-2-amine Chemical compound CC1=CC=NC(NC=2N=C3C=CC=CC3=NC=2)=C1 BSHNAVOQNSIGLC-UHFFFAOYSA-N 0.000 claims 2
- BLOLQFVGPGAZBB-UHFFFAOYSA-N n-(5-bromo-4-methylpyridin-2-yl)quinoxalin-2-amine Chemical compound C1=C(Br)C(C)=CC(NC=2N=C3C=CC=CC3=NC=2)=N1 BLOLQFVGPGAZBB-UHFFFAOYSA-N 0.000 claims 2
- JXNPYZYQNALESK-UHFFFAOYSA-N n-(5-methylpyridin-2-yl)quinolin-3-amine Chemical compound N1=CC(C)=CC=C1NC1=CN=C(C=CC=C2)C2=C1 JXNPYZYQNALESK-UHFFFAOYSA-N 0.000 claims 2
- UIARFWFFSUIOQX-UHFFFAOYSA-N n-(5-methylpyridin-2-yl)quinolin-6-amine Chemical compound N1=CC(C)=CC=C1NC1=CC=C(N=CC=C2)C2=C1 UIARFWFFSUIOQX-UHFFFAOYSA-N 0.000 claims 2
- VVCCKEKCVGLSKU-UHFFFAOYSA-N n-(5-nitropyridin-2-yl)quinolin-3-amine Chemical compound N1=CC([N+](=O)[O-])=CC=C1NC1=CN=C(C=CC=C2)C2=C1 VVCCKEKCVGLSKU-UHFFFAOYSA-N 0.000 claims 2
- PKWLZRUXTBCYEG-UHFFFAOYSA-N n-(6-methylpyridin-2-yl)quinolin-3-amine Chemical compound CC1=CC=CC(NC=2C=C3C=CC=CC3=NC=2)=N1 PKWLZRUXTBCYEG-UHFFFAOYSA-N 0.000 claims 2
- GQBMESGTPZAJPD-UHFFFAOYSA-N n-(6-methylpyridin-2-yl)quinolin-6-amine Chemical compound CC1=CC=CC(NC=2C=C3C=CC=NC3=CC=2)=N1 GQBMESGTPZAJPD-UHFFFAOYSA-N 0.000 claims 2
- RCLQZXYDLVWBFO-UHFFFAOYSA-N n-(6-methylpyridin-2-yl)quinoxalin-2-amine Chemical compound CC1=CC=CC(NC=2N=C3C=CC=CC3=NC=2)=N1 RCLQZXYDLVWBFO-UHFFFAOYSA-N 0.000 claims 2
- DIHJTBLMXALNBS-UHFFFAOYSA-N n-[2-(trifluoromethoxy)phenyl]quinoxalin-2-amine Chemical compound FC(F)(F)OC1=CC=CC=C1NC1=CN=C(C=CC=C2)C2=N1 DIHJTBLMXALNBS-UHFFFAOYSA-N 0.000 claims 2
- IJZNNUVDSNDKDH-UHFFFAOYSA-N n-[2-methyl-4-(trifluoromethoxy)phenyl]quinoxalin-2-amine Chemical compound CC1=CC(OC(F)(F)F)=CC=C1NC1=CN=C(C=CC=C2)C2=N1 IJZNNUVDSNDKDH-UHFFFAOYSA-N 0.000 claims 2
- BXOAUNVKKPBHQR-UHFFFAOYSA-N n-[3-(trifluoromethoxy)phenyl]quinoxalin-2-amine Chemical compound FC(F)(F)OC1=CC=CC(NC=2N=C3C=CC=CC3=NC=2)=C1 BXOAUNVKKPBHQR-UHFFFAOYSA-N 0.000 claims 2
- KYQIWVOWNUXADS-UHFFFAOYSA-N n-[4-(trifluoromethoxy)phenyl]quinoxalin-2-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CN=C(C=CC=C2)C2=N1 KYQIWVOWNUXADS-UHFFFAOYSA-N 0.000 claims 2
- JPVBCHHROCTOAY-UHFFFAOYSA-N n-[5-(trifluoromethyl)pyridin-2-yl]quinolin-3-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1NC1=CN=C(C=CC=C2)C2=C1 JPVBCHHROCTOAY-UHFFFAOYSA-N 0.000 claims 2
- UWRDSNDFPLLAEN-UHFFFAOYSA-N n-[5-(trifluoromethyl)pyridin-2-yl]quinolin-6-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1NC1=CC=C(N=CC=C2)C2=C1 UWRDSNDFPLLAEN-UHFFFAOYSA-N 0.000 claims 2
- DGRWWQSIXMNUFG-UHFFFAOYSA-N n-pyridin-2-ylquinoxalin-2-amine Chemical compound C=1N=C2C=CC=CC2=NC=1NC1=CC=CC=N1 DGRWWQSIXMNUFG-UHFFFAOYSA-N 0.000 claims 2
- VIOGBDYTMPSFOP-UHFFFAOYSA-N n-pyrimidin-2-ylquinolin-2-amine Chemical compound C=1C=C2C=CC=CC2=NC=1NC1=NC=CC=N1 VIOGBDYTMPSFOP-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- YFSKNMVMVDRGQL-UHFFFAOYSA-N 1-n-(6-chloroquinolin-2-yl)-4-n,4-n-dimethylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=C(C=C(Cl)C=C2)C2=N1 YFSKNMVMVDRGQL-UHFFFAOYSA-N 0.000 claims 1
- KROFVRIRTYNLBH-UHFFFAOYSA-N 1-n-(8-chloroquinolin-2-yl)-4-(trifluoromethoxy)benzene-1,2-diamine Chemical compound NC1=CC(OC(F)(F)F)=CC=C1NC1=CC=C(C=CC=C2Cl)C2=N1 KROFVRIRTYNLBH-UHFFFAOYSA-N 0.000 claims 1
- SJQBOAPYEWHLJK-UHFFFAOYSA-N 1-n-(8-chloroquinolin-2-yl)-4-n,4-n-dimethylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=C(C=CC=C2Cl)C2=N1 SJQBOAPYEWHLJK-UHFFFAOYSA-N 0.000 claims 1
- AGJXIRGBYDQMRP-UHFFFAOYSA-N 2-(quinolin-2-ylamino)pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC(NC=2N=C3C=CC=CC3=CC=2)=C1 AGJXIRGBYDQMRP-UHFFFAOYSA-N 0.000 claims 1
- FXWXPPMZBPDNTC-UHFFFAOYSA-N 2-(quinolin-2-ylamino)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(NC=2N=C3C=CC=CC3=CC=2)=C1 FXWXPPMZBPDNTC-UHFFFAOYSA-N 0.000 claims 1
- JXMJKMAWRLFXAP-UHFFFAOYSA-N 2-[(4-methylquinolin-2-yl)amino]pyridine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=NC=CC=C1C#N JXMJKMAWRLFXAP-UHFFFAOYSA-N 0.000 claims 1
- BKJDCCJYCUPNRL-UHFFFAOYSA-N 2-[(8-chloroquinolin-2-yl)amino]pyridin-3-ol Chemical compound OC1=CC=CN=C1NC1=CC=C(C=CC=C2Cl)C2=N1 BKJDCCJYCUPNRL-UHFFFAOYSA-N 0.000 claims 1
- UBKNQKFAALWYST-UHFFFAOYSA-N 2-[(8-chloroquinolin-2-yl)amino]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=C(C=CC=C2Cl)C2=N1 UBKNQKFAALWYST-UHFFFAOYSA-N 0.000 claims 1
- SXYZJVGUCCEKGQ-UHFFFAOYSA-N 2-[(8-chloroquinolin-2-yl)amino]pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(NC=2N=C3C(Cl)=CC=CC3=CC=2)=C1 SXYZJVGUCCEKGQ-UHFFFAOYSA-N 0.000 claims 1
- YFKLMAPHIMPQJI-UHFFFAOYSA-N 2-n-(4-methylpyridin-2-yl)quinoline-2,5-diamine Chemical compound CC1=CC=NC(NC=2N=C3C=CC=C(N)C3=CC=2)=C1 YFKLMAPHIMPQJI-UHFFFAOYSA-N 0.000 claims 1
- LQYGHYLIGWZTLP-UHFFFAOYSA-N 2-n-(4-methylpyridin-2-yl)quinoline-2,8-diamine Chemical compound CC1=CC=NC(NC=2N=C3C(N)=CC=CC3=CC=2)=C1 LQYGHYLIGWZTLP-UHFFFAOYSA-N 0.000 claims 1
- VGWOMTPTPCNRSD-UHFFFAOYSA-N 2-n-(8-chloroquinolin-2-yl)-4-methylpyridine-2,3-diamine Chemical compound CC1=CC=NC(NC=2N=C3C(Cl)=CC=CC3=CC=2)=C1N VGWOMTPTPCNRSD-UHFFFAOYSA-N 0.000 claims 1
- YRKSELLNQXQCRF-UHFFFAOYSA-N 3-methyl-n-(4-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=NC(NC=2C(=CC3=CC=CC=C3N=2)C)=C1 YRKSELLNQXQCRF-UHFFFAOYSA-N 0.000 claims 1
- WTXUYUSDSQGBAN-UHFFFAOYSA-N 3-methyl-n-(6-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=CC(NC=2C(=CC3=CC=CC=C3N=2)C)=N1 WTXUYUSDSQGBAN-UHFFFAOYSA-N 0.000 claims 1
- HLZQAAVXDMDYFS-UHFFFAOYSA-N 3-methyl-n-[2-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=CC=C1OC(F)(F)F HLZQAAVXDMDYFS-UHFFFAOYSA-N 0.000 claims 1
- FQULGNZYLGGSSU-UHFFFAOYSA-N 3-methyl-n-[2-methyl-4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound CC1=CC(OC(F)(F)F)=CC=C1NC1=NC2=CC=CC=C2C=C1C FQULGNZYLGGSSU-UHFFFAOYSA-N 0.000 claims 1
- VGMBGEVZRWQBOM-UHFFFAOYSA-N 3-methyl-n-[3-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=CC(OC(F)(F)F)=C1 VGMBGEVZRWQBOM-UHFFFAOYSA-N 0.000 claims 1
- FWXKBWUMNDDJHT-UHFFFAOYSA-N 3-methyl-n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=C(OC(F)(F)F)C=C1 FWXKBWUMNDDJHT-UHFFFAOYSA-N 0.000 claims 1
- RUIHEVIZDKFBBX-UHFFFAOYSA-N 3-methyl-n-[5-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=C(C(F)(F)F)C=N1 RUIHEVIZDKFBBX-UHFFFAOYSA-N 0.000 claims 1
- BFRIMUUKUWOPBW-UHFFFAOYSA-N 3-methyl-n-pyrazin-2-ylquinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CN=CC=N1 BFRIMUUKUWOPBW-UHFFFAOYSA-N 0.000 claims 1
- PJKUHBGZFLHCNB-UHFFFAOYSA-N 3-methyl-n-pyridin-2-ylquinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=CC=N1 PJKUHBGZFLHCNB-UHFFFAOYSA-N 0.000 claims 1
- PFFGMKJSHDWGGT-UHFFFAOYSA-N 4-methoxy-n-[4-(trifluoromethoxy)phenyl]quinolin-7-amine Chemical compound C=1C=C2C(OC)=CC=NC2=CC=1NC1=CC=C(OC(F)(F)F)C=C1 PFFGMKJSHDWGGT-UHFFFAOYSA-N 0.000 claims 1
- KQHZIQRXEWLDJA-UHFFFAOYSA-N 4-methyl-n-(4-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=NC(NC=2N=C3C=CC=CC3=C(C)C=2)=C1 KQHZIQRXEWLDJA-UHFFFAOYSA-N 0.000 claims 1
- GHJMOXJEERLACS-UHFFFAOYSA-N 4-methyl-n-(5-nitropyridin-2-yl)quinolin-2-amine Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=CC=C([N+]([O-])=O)C=N1 GHJMOXJEERLACS-UHFFFAOYSA-N 0.000 claims 1
- BICKHJDFQUBMDX-UHFFFAOYSA-N 4-methyl-n-(6-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=CC(NC=2N=C3C=CC=CC3=C(C)C=2)=N1 BICKHJDFQUBMDX-UHFFFAOYSA-N 0.000 claims 1
- OCEOPRHNGQCGSQ-UHFFFAOYSA-N 4-methyl-n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=CC=C(OC(F)(F)F)C=C1 OCEOPRHNGQCGSQ-UHFFFAOYSA-N 0.000 claims 1
- WZMXBKQUZOMDOY-UHFFFAOYSA-N 4-methyl-n-pyrazin-2-ylquinolin-2-amine Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=CN=CC=N1 WZMXBKQUZOMDOY-UHFFFAOYSA-N 0.000 claims 1
- ADHHGODRRRVYSR-UHFFFAOYSA-N 4-methyl-n-pyridin-2-ylquinolin-2-amine Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=CC=CC=N1 ADHHGODRRRVYSR-UHFFFAOYSA-N 0.000 claims 1
- HTXYLYNDCJUKPB-UHFFFAOYSA-N 4-morpholin-4-yl-n-[4-(trifluoromethoxy)phenyl]quinolin-7-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CC=C(C(=CC=N2)N3CCOCC3)C2=C1 HTXYLYNDCJUKPB-UHFFFAOYSA-N 0.000 claims 1
- YMWJCWKLKHOUSB-UHFFFAOYSA-N 4-n,4-n-dimethyl-1-n-(3-methylquinolin-2-yl)benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC2=CC=CC=C2C=C1C YMWJCWKLKHOUSB-UHFFFAOYSA-N 0.000 claims 1
- OWEYRQNNNZFLKZ-UHFFFAOYSA-N 4-n,4-n-dimethyl-7-n-[4-(trifluoromethoxy)phenyl]quinoline-4,7-diamine Chemical compound C=1C=C2C(N(C)C)=CC=NC2=CC=1NC1=CC=C(OC(F)(F)F)C=C1 OWEYRQNNNZFLKZ-UHFFFAOYSA-N 0.000 claims 1
- LHEPULDUSUAMAY-UHFFFAOYSA-N 6-(quinolin-2-ylamino)pyridine-3-carbonitrile Chemical compound N1=CC(C#N)=CC=C1NC1=CC=C(C=CC=C2)C2=N1 LHEPULDUSUAMAY-UHFFFAOYSA-N 0.000 claims 1
- VZZOWEGAADNEDX-UHFFFAOYSA-N 6-[(3-methylquinolin-2-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=C(C#N)C=N1 VZZOWEGAADNEDX-UHFFFAOYSA-N 0.000 claims 1
- YZUSLURXWJRRKQ-UHFFFAOYSA-N 6-[(4-methylquinolin-2-yl)amino]pyridine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=CC=C(C#N)C=N1 YZUSLURXWJRRKQ-UHFFFAOYSA-N 0.000 claims 1
- HYQKEYKCHFZSNV-UHFFFAOYSA-N 6-[(8-chloroquinolin-2-yl)amino]-2-methylpyridine-3-carbonitrile Chemical compound C1=C(C#N)C(C)=NC(NC=2N=C3C(Cl)=CC=CC3=CC=2)=C1 HYQKEYKCHFZSNV-UHFFFAOYSA-N 0.000 claims 1
- NQUSIBMZMQGZJP-UHFFFAOYSA-N 6-[(8-chloroquinolin-2-yl)amino]pyridine-3-carbonitrile Chemical compound N1=C2C(Cl)=CC=CC2=CC=C1NC1=CC=C(C#N)C=N1 NQUSIBMZMQGZJP-UHFFFAOYSA-N 0.000 claims 1
- YGTLRZXTQCCYGE-UHFFFAOYSA-N 6-chloro-n-(4-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=NC(NC=2N=C3C=CC(Cl)=CC3=CC=2)=C1 YGTLRZXTQCCYGE-UHFFFAOYSA-N 0.000 claims 1
- FDBFJLXCAOZZFL-UHFFFAOYSA-N 6-chloro-n-(5-fluoropyridin-2-yl)quinolin-2-amine Chemical compound N1=CC(F)=CC=C1NC1=CC=C(C=C(Cl)C=C2)C2=N1 FDBFJLXCAOZZFL-UHFFFAOYSA-N 0.000 claims 1
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- URFTWAYRGCNQTE-UHFFFAOYSA-N n-(5-nitropyridin-2-yl)quinolin-2-amine Chemical compound N1=CC([N+](=O)[O-])=CC=C1NC1=CC=C(C=CC=C2)C2=N1 URFTWAYRGCNQTE-UHFFFAOYSA-N 0.000 claims 1
- VSXGLAGXFHRXQM-UHFFFAOYSA-N n-(6-ethylpyridin-2-yl)-3-methylquinolin-2-amine Chemical compound CCC1=CC=CC(NC=2C(=CC3=CC=CC=C3N=2)C)=N1 VSXGLAGXFHRXQM-UHFFFAOYSA-N 0.000 claims 1
- ZTKSVFASFFNDNT-UHFFFAOYSA-N n-(6-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=CC(NC=2N=C3C=CC=CC3=CC=2)=N1 ZTKSVFASFFNDNT-UHFFFAOYSA-N 0.000 claims 1
- NOFXAEONSDUIOM-UHFFFAOYSA-N n-[2-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound FC(F)(F)OC1=CC=CC=C1NC1=CC=C(C=CC=C2)C2=N1 NOFXAEONSDUIOM-UHFFFAOYSA-N 0.000 claims 1
- OXMZVGXPQMUGTF-UHFFFAOYSA-N n-[2-methyl-4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound CC1=CC(OC(F)(F)F)=CC=C1NC1=CC=C(C=CC=C2)C2=N1 OXMZVGXPQMUGTF-UHFFFAOYSA-N 0.000 claims 1
- NVOIOZMCFMHTMV-UHFFFAOYSA-N n-[3-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound FC(F)(F)OC1=CC=CC(NC=2N=C3C=CC=CC3=CC=2)=C1 NVOIOZMCFMHTMV-UHFFFAOYSA-N 0.000 claims 1
- BCTMSDUZMDOITG-UHFFFAOYSA-N n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CC=C(C=CC=C2)C2=N1 BCTMSDUZMDOITG-UHFFFAOYSA-N 0.000 claims 1
- IFKURQMAQPEGBY-UHFFFAOYSA-N n-[4-(trifluoromethoxy)phenyl]quinolin-3-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CN=C(C=CC=C2)C2=C1 IFKURQMAQPEGBY-UHFFFAOYSA-N 0.000 claims 1
- FMVVRHSNCORERJ-UHFFFAOYSA-N n-[5-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1NC1=CC=C(C=CC=C2)C2=N1 FMVVRHSNCORERJ-UHFFFAOYSA-N 0.000 claims 1
- DJQMBIOZCUXCGM-UHFFFAOYSA-N n-[6-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine Chemical compound FC(F)(F)C1=CC=CC(NC=2N=C3C=CC=CC3=CC=2)=N1 DJQMBIOZCUXCGM-UHFFFAOYSA-N 0.000 claims 1
- BEEMTSFIVSXCQT-UHFFFAOYSA-N n-naphthalen-2-ylpyridin-2-amine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=N1 BEEMTSFIVSXCQT-UHFFFAOYSA-N 0.000 claims 1
- UQECIBDLOFNABS-UHFFFAOYSA-N n-pyrazin-2-ylquinolin-2-amine Chemical compound C=1C=C2C=CC=CC2=NC=1NC1=CN=CC=N1 UQECIBDLOFNABS-UHFFFAOYSA-N 0.000 claims 1
- UFMKHVYZRJLHMM-UHFFFAOYSA-N n-pyrazin-2-ylquinolin-3-amine Chemical compound C=1N=C2C=CC=CC2=CC=1NC1=CN=CC=N1 UFMKHVYZRJLHMM-UHFFFAOYSA-N 0.000 claims 1
- NRBSSBDWCJDZTE-UHFFFAOYSA-N n-pyrazin-2-ylquinolin-6-amine Chemical compound C=1C=C2N=CC=CC2=CC=1NC1=CN=CC=N1 NRBSSBDWCJDZTE-UHFFFAOYSA-N 0.000 claims 1
- YQZNQAOPVNOFQW-UHFFFAOYSA-N n-pyridin-2-ylquinolin-3-amine Chemical compound C=1N=C2C=CC=CC2=CC=1NC1=CC=CC=N1 YQZNQAOPVNOFQW-UHFFFAOYSA-N 0.000 claims 1
- BTMYCMDJXRGRLY-UHFFFAOYSA-N n-pyridin-3-ylquinolin-3-amine Chemical compound C=1N=C2C=CC=CC2=CC=1NC1=CC=CN=C1 BTMYCMDJXRGRLY-UHFFFAOYSA-N 0.000 claims 1
- PZGCDTSZRXPXBJ-UHFFFAOYSA-N n-pyridin-4-ylquinolin-2-amine Chemical compound C=1C=C2C=CC=CC2=NC=1NC1=CC=NC=C1 PZGCDTSZRXPXBJ-UHFFFAOYSA-N 0.000 claims 1
- YYFITUYWFOTKBO-UHFFFAOYSA-N n-pyridin-4-ylquinolin-3-amine Chemical compound C=1N=C2C=CC=CC2=CC=1NC1=CC=NC=C1 YYFITUYWFOTKBO-UHFFFAOYSA-N 0.000 claims 1
- QDEITQFFEKGMCH-UHFFFAOYSA-N n-pyrimidin-2-ylquinoxalin-2-amine Chemical compound C=1N=C2C=CC=CC2=NC=1NC1=NC=CC=N1 QDEITQFFEKGMCH-UHFFFAOYSA-N 0.000 claims 1
- 229940125268 obefazimod Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
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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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P35/00—Antineoplastic agents
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
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- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (10)
1. Spoj s formulom (I):
[image]
naznačen time što:
[image]
predstavlja aromatski prsten pri čemu V je C ili N i kada V je N, V je u orto, meta ili para položaju prema Z, tj. tvori piridazinsku, pirimidinsku ili pirazinsku skupinu,
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabrana između skupine -CN, hidroksilne skupine, skupine -COOR1 , skupine (C1-C3)fluoralkil, skupine (C1-C3)fluoralkoksi, -NO2 skupine, -NR1R2 skupine, (C1-C4)alkoksi skupine, fenoksi skupine i skupine (C1-C3)alkil, navedeni alkil je izborno mono-supstituiran s hidroksilnom skupinom,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
n je 1, 2 ili 3,
n' je 1 ili 2,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil, hidroksilne skupine, -COOR1 skupine, -NO2 skupine, -NR1R2 skupine, skupine morfolinil ili morfolino skupine, N-metilpiperazinil skupine, (C1-C3)fluoralkil skupine, (C1-C4)alkoksi skupine i -CN skupine,
R" je vodikov atom ili skupina (C1-C4)alkil,
- Z je N, V je C, Y je N, X je C, T je C, U je C i W je C,
- Z je C, V je C, Y je N, X je C, T je C, U je C i W je C,
- Z je N, V je C, Y je C, X je N, T je C, U je C i W je C,
- Z je N, V je C, Y je C, X je C, T je C, U je C i W je N,
- Z je N, V je N i u para položaju je prema Z, Y je N, X je C, T je C, U je C i W je C
- Z je C, V je N i u para položaju je prema Z, Y je C, X je N, T je C, U je C i W je C,
- Z je C, V je N i u meta položaju je prema Z i u para položaju je prema vezi povezanoj s NR", Y je N, X je C, T je C, U je C i W je C,
- Z je C, V je N i je u meta položaju prema Z i je u para položaju prema vezi povezanoj s NR", Y je C, X je N, T je C, U je C i W je C,
- Z je C, V je C, Y je C, X je N, T je C, U je C i W je C,
- Z je C, V je C, Y je N, X je N, T je C, U je C i W je C,
- Z je N, V je N i u meta položaju je prema Z i u orto položaju prema vezi povezanoj s NR", Y je N, X je C, T je C, U je C i W je C,
- Z je N, V je N i u para položaju je prema Z, Y je C, X je C, T je C, U je C i W je N,
- Z je N, V je N i u para položaju je prema Z, Y je C, X je N, T je C, U je C i W je C,
- Z je N, V je C, Y je N, X je N, T je C, U je C i W je C,
- Z je N, V je N i u meta položaju je prema Z i u orto položaju je prema vezi povezanoj s NR", Y je N, X je N, T je C, U je C i W je C,
- Z je C, V je C, Y je C, X je C, T je N, U je C i W je C, ili
- Z je N, V je C, Y je C, X je C, T je N, U je C i W je C,
ili bilo koja od njegovih farmaceutski prihvatljivih soli,
za upotrebu kao sredstvo za prevenciju, inhibiciju ili liječenje patoloških stanja povezanih s preranim starenjem.
2. Spoj s formulom (I) prema zahtjevu 1, naznačen time što alternativno:
- Z je N, V je C, Y je N, X je C, T je C, U je C i W je C,
- Z je C, V je C, Y je N, X je C, T je C, U je C i W je C,
- Z je N, V je C, Y je C, X je N, T je C, U je C i W je C,
- Z je N, V je C, Y je C, X je C, T je C, U je C i W je N,
- Z je N, V je N i u para položaju je prema Z, Y je N, X je C, T je C, U je C i W je C,
- Z je C, V je C, Y je C, X je N, T je C, U je C i W je C,
- Z je C, V je C, Y je N, X je N, T je C, U je C i W je C,
- Z je N, V je N i u meta položaju je prema Z i u orto položaju je prema vezi povezanoj s NR", Y je N, X je C, T je C, U je C i W je C,
- Z je N, V je C, Y je N, X je N, T je C, U je C i W je C,
- Z je N, V je N i u meta položaju je prema Z i u orto položaju je prema vezi povezanoj s NR", Y je N, X je N, T je C, U je C i W je C, ili
- Z je N, V je C, Y je C, X je C, T je N, U je C i W je C,
za upotrebu kao sredstvo za prevenciju, inhibiciju ili liječenje patoloških stanja povezanih s preranim starenjem.
3. Spoj s formulom (I) prema bilo kojem od prethodnih zahtjeva, za upotrebu kao sredstvo za prevenciju, inhibiciju ili liječenje patoloških stanja povezanih s preranim starenjem, koji je alternativno izabran između: (1)
[image]
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, -CN skupine, hidroksilne skupine, -COOR1 skupine, skupine (C1-C3)fluoralkil, -NO2 skupine, -NR1R2 skupine i (C1-C3)alkoksi skupine,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil, skupine -NO2 , (C1-C3)alkoksi skupine i -NR1R2 skupine,
R1 i R2 su vodikov atom ili skupina (C1-C3)alkil,
[image]
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, skupine -NR1R2 , (C1-C3)fluoralkoksi skupine, -NO2 skupine, fenoksi skupine i (C1-C4)alkoksi skupine,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i poželjno je 1 ili 2,
n' je kako je definirano u zahtjevu 1 i poželjno je 1,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil i (C1-C4)alkoksi skupine,
[image]
pri čemu:
R neovisno predstavlja vodikov atom ili skupinu odabranu između skupine (C1-C3)alkil, skupine (C1-C3)fluoralkil, -NR1R2 skupine, -COOR1 skupine, -NO2 skupine i (C1-C3)alkoksi skupine,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
[image]
pri čemu:
R neovisno predstavlja vodikov atom ili skupinu odabranu između skupine (C1-C3)alkil, skupine (C1-C3)fluoralkil i skupine (C1-C3)alkoksi,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom,
[image]
pri čemu:
R predstavlja vodikov atom,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil i skupine (C1-C3)alkoksi,
[image]
pri čemu:
R predstavlja vodikov atom,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom,
[image]
pri čemu:
R predstavlja vodikov atom,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom ili halogeni atom,
[image]
pri čemu:
R predstavlja vodikov atom,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom,
[image]
pri čemu:
R neovisno predstavlja vodikov atom ili skupinu odabranu između skupine (C1-C3)fluoralkoksi i skupine (C1-C3)alkoksi,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom,
[image]
pri čemu:
R neovisno predstavlja vodikov atom ili skupinu odabranu između skupine (C1-C3)fluoralkoksi i skupine (C1-C3)alkil,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom,
[image]
pri čemu:
R predstavlja vodikov atom,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom, halogeni atom ili skupina (C1-C3)alkil,
[image]
pri čemu:
R predstavlja vodikov atom,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom,
[image]
pri čemu:
R predstavlja vodikov atom,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom,
[image]
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između, -NO2 skupine, -CN skupine i skupine (C1-C3)alkil, navedeni alkil je izborno mono-supstituiran s hidroksilnom skupinom,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom, halogeni atom ili skupina (C1-C3)fluoralkil,
[image]
pri čemu:
R predstavlja vodikov atom,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom,
[image]
pri čemu:
R neovisno predstavlja vodikov atom, skupinu (C1-C3)alkoksi ili skupinu (C1-C3)fluoralkoksi,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom ili skupina odabrana između -NR1R2 skupine, N-metilpiperazinil skupine, (C1-C3)alkoksi skupine i morfolino skupine,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
[image]
pri čemu:
R neovisno predstavlja vodikov atom ili skupinu (C1-C3)alkil,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
R' je vodikov atom ili skupina odabrana između -NR1R2 skupine, morfolino skupine i (C1-C3)alkoksi skupine,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil, (18)
ili jedna od njegovih farmaceutski prihvatljivih soli.
4. Spoj s formulom (I) prema bilo kojem od prethodnih zahtjeva, za upotrebu kao sredstvo za prevenciju, inhibiciju ili liječenje patoloških stanja povezanih s preranim starenjem, koji je alternativno izabran između:
[image]
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, -CN skupine, -COOR1 skupine, skupine (C1-C3)fluoralkil, - NO2 skupine i skupine (C1-C3)alkoksi,
R1 je vodikov atom ili skupina (C1-C3)alkil,
R" je kako je definirano u zahtjevu 1 i poželjnije je vodikov atom,
n je kako je definirano u zahtjevu 1 i poželjnije je 1,
n' je kako je definirano u zahtjevu 1,
R' je vodikov atom, halogeni atom ili skupina (C1-C3)alkil,
[image]
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, skupine (C1-C3)fluoralkoksi i fenoksi skupine,
R1 je vodikov atom ili skupina (C1-C3)alkil,
R" je kako je definirano u zahtjevu 1 i poželjnije je vodikov atom,
n je kako je definirano u zahtjevu 1 i poželjnije je 1,
n' je kako je definirano u zahtjevu 1,
R' je vodikov atom,
[image]
pri čemu:
R neovisno predstavlja vodikov atom ili skupinu odabranu između skupine (C1-C3)alkil, -NO2 skupine i (C1-C3)alkoksi skupine,
R" je kako je definirano u zahtjevu 1 i poželjnije je vodikov atom,
n je kako je definirano u zahtjevu 1 i poželjnije je 1,
n' je kako je definirano u zahtjevu 1,
R' je vodikov atom,
[image]
pri čemu:
R predstavlja vodikov atom,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n je kako je definirano u zahtjevu 1 i pogodno je 1,
n' je kako je definirano u zahtjevu 1,
R' je vodikov atom ili halogeni atom,
[image]
pri čemu:
R neovisno predstavlja vodikov atom ili (C1-C3)alkoksi skupinu,
R" je kako je gore definirano i pogodno je vodikov atom,
n je kako je gore definirano i pogodno je 1,
n' je kako je gore definirano i pogodno je 1,
R' je vodikov atom,
[image]
pri čemu:
R neovisno predstavlja vodikov atom ili skupinu odabranu između skupine (C1-C3)fluoralkoksi i skupine (C1-C3)alkil,
R" je kako je definirano u zahtjevu 1 i poželjnije je vodikov atom,
n je kako je definirano u zahtjevu 1 i poželjnije je 2,
n' je kako je definirano u zahtjevu 1,
R' je vodikov atom,
[image]
pri čemu:
R predstavlja vodikov atom,
R" je kako je definirano u zahtjevu 1 i poželjnije je vodikov atom,
n je kako je definirano u zahtjevu 1 i poželjnije je 1,
n' je kako je definirano u zahtjevu 1,
R' je vodikov atom,
[image]
pri čemu:
R neovisno predstavlja vodikov atom ili skupinu odabranu između skupine (C1-C3)alkil i -CN skupine,
R" je kako je definirano u zahtjevu 1 i poželjnije je vodikov atom,
n je kako je definirano u zahtjevu 1 i poželjnije je 1,
n' je kako je definirano u zahtjevu 1 i poželjnije je 1,
R' je vodikov atom, (9)
ili jedna od njegovih farmaceutski prihvatljivih soli.
5. Spoj s formulom (I) prema bilo kojem od zahtjeva 1 do 3, koji je alternativno izabran između,
(1) spoja s formulom (Ig) kako je definiran u zahtjevu 3
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, -CN skupine, hidroksilne skupine, -COOR1 skupine, skupine (C1-C3)fluoralkil, skupine (C1-C3)fluoralkoksi, -NO2 skupine, -NR1R2 skupine, i skupine (C1-C3)alkoksi,
n je 1 ili 2,
n' je 1 ili 2,
R' je vodikov atom ili skupina odabrana između skupine (C1-C3)alkil, halogenog atoma, hidroksilne skupine, -COOR1 skupine, -NO2 skupine, -NR1R2 skupine, skupine (C1-C3)alkoksi i -CN skupine,
R" je vodikov atom ili skupina (C1-C4)alkil,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
pod uvjetom da R i R' nisu istovremeno vodikov atom,
i kada n i n' su 1 i R je vodikov atom tada R' nije -COOH skupina,
ili bilo koja od njegovih farmaceutski prihvatljivih soli,
(2) spoja s formulom (Ic) kako je definiran u zahtjevu 3
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, -CN skupine, hidroksilne skupine, -COOR1 skupine, skupine (C1-C3)fluoralkil, -NO2 skupine, -NR1R2 skupine i skupine (C1-C3)alkoksi,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
n je 1 ili 2, i ponajprije 1,
n' je 1 ili 2,
R" je kako je definiran u formuli (Ic) u zahtjevu 3,
R' je vodikov atom ili skupina odabrana između skupine (C1-C3)alkil, -NO2 skupine, -NR1R2 skupine i skupine (C1-C3)alkoksi,
pod uvjetom da
R i R' nisu istovremeno vodikov atom,
R nije atom broma kada R' je vodikov atom,
ili jedna od njegovih farmaceutski prihvatljivih soli,
(3) spoja s formulom (Id) kako je definiran u zahtjevu 3
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, -CN skupine, hidroksilne skupine, -COOR1 skupine, skupine (C1-C3)fluoralkil, skupine (C1-C3)fluoralkoksi, -NO2 skupine i -NR1R2 skupine,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
n je 1 ili 2, i ponajprije 1,
n' je 1 ili 2,
R" je kako je definiran u formuli (I) u zahtjevu 1 i pogodno je vodikov atom,
R' je vodikov atom ili skupina odabrana između skupine (C1-C3)alkil, -NO2 skupine, -NR1R2 skupine i skupine (C1-C3)alkoksi,
pod uvjetom da kada R' je vodikov atom, R je različit od -NO2 skupine, -NH2 skupine ili -COOH skupine,
ili jedna od njegovih farmaceutski prihvatljivih soli,
(4) spoja s formulom (Ii')
[image]
pri čemu:
R3 je skupina (C1-C3)fluoralkil ili skupina (C1-C3)alkil,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil, hidroksilne skupine, -COOR1 skupine, -NO2 skupine, -NR1R2 skupine, skupine (C1-C3)alkoksi i -CN skupine,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
pod uvjetom da
kada R' je vodikov atom, R3 nije metilna skupina ili trifluorometilna skupina
ili jedna od njegovih farmaceutski prihvatljivih soli.
6. Spoj s formulom (I) prema bilo kojem od zahtjeva 1 do 3, koji je alternativno izabran između,
(1) spoja s formulom (Ik) kako je definiran u zahtjevu 3
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, -CN skupine, hidroksilne skupine, -COOR1 skupine, skupine (C1-C3)fluoralkil, skupine (C1-C3)fluoralkoksi, -NO2 skupine, -NR1R2 skupine i skupine (C1-C3)alkoksi,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
n je 1 ili 2, i pogodno je 1,
n' je 1 ili 2,
R" je kako je definiran u formuli (Ik) u zahtjevu 3,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil, hidroksilne skupine, -COOR1 skupine, -NO2 skupine, -NR1R2 skupine, skupine (C1-C3)alkoksi i -CN skupine,
ili jedna od njegovih farmaceutski prihvatljivih soli,
(2) spoja s formulom (Io) kako je definiran u zahtjevu 3
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, -CN skupine, hidroksilne skupine, -COOR1 skupine, skupine (C1-C3)fluoralkil, skupine (C1-C3)fluoralkoksi, -NO2 skupine, -NR1R2 skupine i skupine (C1-C3)alkoksi,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
n je 1, 2 ili 3,
n' je 1 ili 2,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil, hidroksilne skupine, -COOR1 skupine, -NO2 skupine, -NR1R2 skupine, skupine (C1-C3)alkoksi i -CN skupine,
R" je vodikov atom ili skupina (C1-C4)alkil,
pod uvjetom da
kada R je vodikov atom i n' je 1, R' nije hidroksilna skupina,
ili jedna od njegovih farmaceutski prihvatljivih soli,
(3) spoja s formulom (Ij')
[image]
pri čemu:
R4 je skupina (C1-C3)fluoralkil ili skupina (C1-C3)alkil,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil, hidroksilne skupine, -COOR1 skupine, -NO2 skupine, -NR1R2 skupine, skupine (C1-C3)alkoksi i -CN skupine,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
pod uvjetom da
kada R' je vodikov atom, R4 nije metilna skupina
ili jedna od njegovih farmaceutski prihvatljivih soli,
(4) spoja s formulom (Ij")
[image]
pri čemu:
R4 je skupina (C1-C3)fluoralkil ili skupina (C1-C3)alkil,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil, hidroksilne skupine, -COOR1 skupine, -NO2 skupine, -NR1R2 skupine, skupine (C1-C3)alkoksi i -CN skupine,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
ili jedna od njegovih farmaceutski prihvatljivih soli,
(5) spoja s formulom (Ij‴)
[image]
pri čemu:
R4 je skupina (C1-C3)fluoralkil ili skupina (C1-C3)alkil,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil, hidroksilne skupine, -NO2 skupine, -NR1R2 skupine, skupine (C1-C3)alkoksi i -CN skupine,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
R" je kako je definirano u zahtjevu 1 i pogodno je vodikov atom,
n' je kako je definirano u zahtjevu 1 i pogodno je 1,
pod uvjetom da
kada R' je klorov atom ili vodikov atom, R4 nije etilna skupina ili metilna skupina,
kada R' je metilna skupina ili tertio-butilna skupina, R4 nije metil skupina,
ili jedna od njegovih farmaceutski prihvatljivih soli.
7. Spoj s formulom (I) prema bilo kojem od zahtjeva 1 do 3, koji je alternativno izabran između,
(1) spoja s formulom (Ip) kako je definiran u zahtjevu 3
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, -CN skupine, hidroksilne skupine, -COOR1 skupine, skupine (C1-C3)fluoralkil, skupine (C1-C3)fluoralkoksi, -NO2 skupine, -NR1R2 skupine i skupine (C1-C3)alkoksi,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
n je 1 ili 2, i ponajprije 1,
n' je 1 ili 2,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil, hidroksilne skupine, -COOR1 skupine, -NO2 skupine, -NR1R2 skupine, skupine (C1-C3)alkoksi i -CN skupine,
R" je vodikov atom ili skupina (C1-C4)alkil,
pod uvjetom da
pri čemu R i R' nisu istovremeno vodikov atom,
kada n i n' su 2 tada R i R' nisu istovremeno metilna skupina,
ili jedna od njegovih farmaceutski prihvatljivih soli,
(2) spoja s formulom (Ir) kako je definiran u zahtjevu 3
pri čemu:
R neovisno predstavlja vodikov atom, halogeni atom ili skupinu odabranu između skupine (C1-C3)alkil, -CN skupine, hidroksilne skupine, -COOR1 skupine, skupine (C1-C3)fluoralkil, skupine (C1-C3)fluoralkoksi, -NO2 skupine, -NR1R2 skupine i skupine (C1-C3)alkoksi,
R1 i R2 su neovisno vodikov atom ili skupina (C1-C3)alkil,
n je 1 ili 2, i ponajprije 1,
n' je 1 ili 2,
R' je vodikov atom, halogeni atom ili skupina odabrana između skupine (C1-C3)alkil, hidroksilne skupine, -COOR1 skupine, -NO2 skupine, -NR1R2 skupine, skupine (C1-C3)alkoksi i -CN skupine,
R" je vodikov atom ili skupina (C1-C4)alkil,
ili jedna od njegovih farmaceutski prihvatljivih soli.
8. Spoj za upotrebu u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što je navedeni spoj odabran između slijedećih spojeva:
- (1) (8-Klor-kinolin-2-il)-piridin-2-il-amin
- (2) 2-(Kinolin-2-ilamino)-izonikotinska kiselina
- (3) (4-Metil-piridin-2-il)-kinolin-2-il-amin
- (4) Piridin-2-il-kinolin-2-il-amin
- (5) 2-(8-Klor-kinolin-2-ilamino)-izonikotinska kiselina
- (6) (8-Klor-kinolin-2-il)-(4-metil-piridin-2-il)-amin
- (7) 6-(Kinolin-2-ilamino)-nikotinonitril
- (8) Kinolin-2-il-(4-trifluormetoksi-fenil)-amin
- (9) Piridin-2-il-kinolin-3-il-amin
- (10) (3-Metoksi-piridin-2-il)-kinolin-3-il-amin
- (11) Kinolin-3-il-(5-trifluormetil-piridin-2-il)-amin
- (12) (5-Nitro-piridin-2-il)-kinolin-3-il-amin
- (13) (5-Metil-piridin-2-il)-kinolin-3-il-amin
- (14) 2-(Kinolin-3-ilamino)-izonikotinska kiselina
- (15) Kinolin-6-il-(5-trifluormetil-piridin-2-il)-amin
- (16) (6-Metil-piridin-2-il)-kinolin-6-il-amin
- (17) N-(6-metilpiridin-2-il)kinolin-2-amin
- (18) 8-klor-N-(6-metilpiridin-2-il)kinolin-2-amin
- (19) 4-metil-N-(piridin-2-il)kinolin-2-amin
- (20) 4-metil-N-(4-metilpiridin-2-il)kinolin-2-amin
- (21) 3-metil-N-(4-metilpiridin-2-il)kinolin-2-amin
- (22) 3-metil-N-(piridin-2-il)kinolin-2-amin
- (23) 6-((4-metilkinolin-2-il)amino)nikotinonitril
- (24) 6-((3-metilkinolin-2-il)amino)nikotinonitril
- (25) 6-klor-N-(4-metilpiridin-2-il)kinolin-2-amin
- (26) 6-klor-N-(6-metilpiridin-2-il)kinolin-2-amin
- (27) 4-metil-N-(5-nitropiridin-2-il)kinolin-2-amin
- (28) N-(3-nitropiridin-2-il)kinolin-2-amin
- (29) 8-klor-N-(3-nitropiridin-2-il)kinolin-2-amin
- (30) 2-((4-metilkinolin-2-il)amino)nikotinonitril
- (31) N-(3-metilpiridin-2-il)kinolin-2-amin
- (32) N-(5-metilpiridin-2-il)kinolin-2-amin
- (33) 2-(kinolin-2-ilamino)izonikotinonitril
- (34) N-(5-(trifluormetil)piridin-2-il)kinolin-2-amin
- (35) 8-klor-N-(3-metilpiridin-2-il)kinolin-2-amin
- (36) 8-klor-N-(5-metilpiridin-2-il)kinolin-2-amin
- (37) 8-klor-N-(5-(trifluormetil)piridin-2-il)kinolin-2-amin
- (38) N-(3-metoksipiridin-2-il)kinolin-2-amin
- (39) N-(5-nitropiridin-2-il)kinolin-2-amin
- (40) 6-((8-klorkinolin-2-il)amino)nikotinonitril
- (41) N-(5-fluorpiridin-2-il)kinolin-2-amin
- (42) N-(6-(trifluormetil)piridin-2-il)kinolin-2-amin
- (43) 8-klor-N-(5-fluorpiridin-2-il)kinolin-2-amin
- (44) 2-((8-klorkinolin-2-il)amino)nikotinska kiselina
- (45) 4-metil-N-(6-metilpiridin-2-il)kinolin-2-amin
- (46) 3-metil-N-(6-metilpiridin-2-il)kinolin-2-amin
- (47) 5-cyano-2-(kinolin-2-ilamino)piridin-1-ij klorid
- (48) 2-((8-klorkinolin-2-il)amino)-4-metilpiridin-1-ij klorid
- (49) 8-klor-N-(4-etilpiridin-2-il)kinolin-2-amin
- (50) 8-klor-N-(6-etilpiridin-2-il)kinolin-2-amin
- (51) 8-klor-N-(4,6-dimetilpiridin-2-il)kinolin-2-amin
- (52) 6-((8-klorkinolin-2-il)amino)-2-metilnikotinonitril
- (53) 8-klor-N-(4-klorpiridin-2-il)kinolin-2-amin
- (54) 8-metil-N-(4-metilpiridin-2-il)kinolin-2-amin
- (55) N-(5-bromo-4-metilpiridin-2-il)-8-klorkinolin-2-amin
- (56) 8-klor-N-(3-etil-6-metilpiridin-2-il)kinolin-2-amin
- (57) 8-fluor-N-(4-metilpiridin-2-il)kinolin-2-amin
- (58) 8-bromo-N-(4-metilpiridin-2-il)kinolin-2-amin
- (59) metil 6-(kinolin-2-ilamino)nikotinat
- (60) metil 6-[(8-klorkinolin-2-il)amino]piridin-3-karboksilat
- (61) metil 6-[(3-metilkinolin-2-il)amino]piridin-3-karboksilat
- (62) metil 2-[(8-klorkinolin-2-il)amino]piridin-3-karboksilat
- (63) 8-metoksi-N-(4-metilpiridin-2-il)kinolin-2-amin
- (64) N-(4-metilpiridin-2-il)-5-nitrokinolin-2-amin
- (65) 2-N-(4-metilpiridin-2-il)kinolin-2,8-diamin
- (66) N-(4-metilpiridin-2-il)-5-aminokinolin-2-amin
- (67) metil 6-[(4-metilkinolin-2-il)amino]piridin-3-karboksilat
- (68) 8-klor-N-[4-(trifluormetil)piridin-2-il]kinolin-2-amin
- (69) 2-[(8-klorkinolin-2-il)amino]piridin-3-ol
- (70) 8-klor-N-[6-(trifluormetil)piridin-2-il]kinolin-2-amin
- (71) 6-klor-N-(5-fluorpiridin-2-il)kinolin-2-amin
- (72) N-(6-etilpiridin-2-il)-3-metilkinolin-2-amin
- (73) N-(5-fluorpiridin-2-il)-3-metilkinolin-2-amin
- (74) 3-metil-N-[5-(trifluormetil)piridin-2-il]kinolin-2-amin
- (75) 4-N-(8-klorkinolin-2-il)-1-N,1-N-dimetilbenzen-1,4-diamin
- (76) N-(4-metoksifenil)kinolin-2-amin
- (77) 8-klor-N-(4-metoksifenil)kinolin-2-amin
- (78) 4-metil-N-[4-(trifluormetoksi)fenil]kinolin-2-amin
- (79) N-(4-metoksifenil)-3-metilkinolin-2-amin
- (80) 3-metil-N-[4-(trifluormetoksi)fenil]kinolin-2-amin
- (81) 1-N,1-N-dimetil-4-N-(3 -metilkinolin-2-il)benzen-1,4-diamin
- (82) N-[2-metil-4-(trifluormetoksi)fenil]kinolin-2-amin
- (83) N-[3-(trifluormetoksi)fenil]kinolin-2-amin
- (84) N-[2-(trifluormetoksi)fenil]kinolin-2-amin
- (85) N-(4-nitrofenil)kinolin-2-amin
- (86) N-(3-fluorfenil)kinolin-2-amin
- (87) 8-klor-N-[3-(trifluormetoksi)fenil]kinolin-2-amin
- (88) 8-klor-N-(3-fluorfenil)kinolin-2-amin
- (89) 2-{[4-(trifluormetoksi)fenil]amino}kinolin-1-ij klorid
- (90) 8-klor-N-[4-(trifluormetoksi)fenil]kinolin-2-amin
- (91) 3-metil-N-[2-metil-4-(trifluormetoksi)fenil]kinolin-2-amin
- (92) 3-metil-N-[3-(trifluormetoksi)fenil]kinolin-2-amin
- (93) 3-metil-N-[2-(trifluormetoksi)fenil]kinolin-2-amin
- (94) 8-klor-N-[2-metil-4-(trifluormetoksi)fenil]kinolin-2-amin
- (95) 3-metil-2-{[4-(trifluormetoksi)fenil]amino}kinolin-1-ij klorid
- (96) 6-klor-N-(4-(trifluormetoksi)fenil)kinolin-2-amin
- (97) 4-metil-2-{[4-(trifluormetoksi)fenil]amino}kinolin-1-ij klorid
- (98) 8-bromo-N-[4-(trifluormetoksi)fenil]kinolin-2-amin
- (99) 8-fluor-N-[4-(trifluormetoksi)fenil]kinolin-2-amin
- (100) 8-metil-N-[4-(trifluormetoksi)fenil]kinolin-2-amin
- (101) N-(4-butoksifenil)-8-klorkinolin-2-amin
- (102) N-(4-fenoksifenil)kinolin-2-amin
- (103) 8-metoksi-N-[4-(trifluormetoksi)fenil]kinolin-2-amin
- (104) 8-klor-N-[3-klor-4-(trifluormetoksi)fenil]kinolin-2-amin
- (105) N-(6-metilpiridin-2-il)kinolin-3-amin
- (106) N-(3-nitropiridin-2-il)kinolin-3-amin
- (107) N-(5-metilpiridin-2-il)kinolin-6-amin
- (108) N-(3-metoksipiridin-2-il)kinolin-6-amin
- (109) 6-klor-N-(pirazin-2-il)kinolin-2-amin
- (110) 8-bromo-N-(pirazin-2-il)kinolin-2-amin
- (111) 8-metil-N-(pirazin-2-il)kinolin-2-amin
- (112) 8-klor-N-(pirazin-2-il)kinolin-2-amin
- (113) N-(pirazin-2-il)kinolin-2-amin
- (114) 4-metil-N-(pirazin-2-il)kinolin-2-amin
- (115) 3-metil-N-(pirazin-2-il)kinolin-2-amin
- (116) 8-fluor-N-(pirazin-2-il)kinolin-2-amin
- (117) 8-metoksi-N-(pirazin-2-il)kinolin-2-amin
- (118) N-(piridin-3-il)kinolin-3-amin
- (119) 8-klor-N-(piridin-4-il)kinolin-2-amin
- (120) N-(piridin-4-il)kinolin-2-amin
- (121) N-(piridin-4-il)kinolin-3-amin
- (122) N-[4-(trifluormetoksi)fenil]kinolin-3-amin
- (123) N-(4-metoksifenil)kinolin-3-amin
- (124) N-[4-(trifluormetoksi)fenil]kinoksalin-2-amin
- (125) N-[2-metil-4-(trifluormetoksi)fenil]kinoksalin-2-amin
- (126) N-[3-(trifluormetoksi)fenil]kinoksalin-2-amin
- (127) N-[2-(trifluormetoksi)fenil]kinoksalin-2-amin
- (128) N-(pirimidin-2-il)kinolin-2-amin
- (129) 8-klor-N-(pirimidin-2-il)kinolin-2-amin
- (130) 4-metil-N-(pirimidin-2-il)kinolin-2-amin
- (131) N-(pirazin-2-il)kinolin-6-amin
- (132) N-(pirazin-2-il)kinolin-3-amin
- (133) 6-metil-N-(naftalen-2-il)piridin-2-amin
- (134) N-(naftalen-2-il)piridin-2-amin
- (135) N-(piridin-2-il)kinoksalin-2-amin
- (136) N-(4-metilpiridin-2-il)kinoksalin-2-amin
- (137) 6-(kinoksalin-2-ilamino)piridin-3-karbonitril
- (138) N-(6-metilpiridin-2-il)kinoksalin-2-amin
- (139) N-(4-metilpiridin-2-il)-3-(trifluormetil)kinoksalin-2-amin
- (140) N-(3,5-diklor-4-metilpiridin-2-il)kinoksalin-2-amin
- (141) N-(4-metil-3-nitropiridin-2-il)kinoksalin-2-amin
- (142) N-(pirimidin-2-il)kinoksalin-2-amin
- (143) 4-N,4-N-dimetil-7-N-[4-(trifluormetoksi)fenil]kinolin-4,7-diamin
- (144) 4-(morfolin-4-il)-N-[4-(trifluormetoksi)fenil]kinolin-7-amin
- (145) 4-metoksi-N-(piridin-2-il)kinolin-7-amin
- (146) 4-metoksi-N-(4-metilpiridin-2-il)kinolin-7-amin
- (147) 4-N,4-N-dimetil-7-N-(4-metilpiridin-2-il)kinolin-4,7-diamin
- (150) N-(4-metilpiridin-2-il)-8-nitrokinolin-2-amin
- (151) 6-klor-N-(6-etilpiridin-2-il)kinolin-2-amin
- (152) 6-klor-N-(5-metilpiridin-2-il)kinolin-2-amin
- (153) 6-klor-N-[5-(trifluormetil)piridin-2-il]kinolin-2-amin
- (154) N2-(8-klorkinolin-2-il)-4-metilpiridin-2,3-diamin
- (155) N-(4-butoksifenil)-3-metilkinolin-2-amin
- (156) 4-N-(6-klorkinolin-2-il)-1-N,1-N-dimetilbenzen-1,4-diamin
- (157) 8-klor-N-(3-klor-4-metoksifenil)kinolin-2-amin
- (158) N1-(8-klorkinolin-2-il)-4-(trifluormetoksi)benzen-1,2-diamin
- (159) N-(3-aminopiridin-2-il)kinolin-3-amin
- (160) 6-klor-N-(4-metilpiridin-2-il)kinoksalin-2-amin
- (161) N-(4-etilpiridin-2-il)kinoksalin-2-amin
- (162) N-(5-bromo-4-metilpiridin-2-il)kinoksalin-2-amin
- (163) N-(4,6-dimetilpiridin-2-il)kinoksalin-2-amin
- (164) [2-(kinoksalin-2-ilamino)piridin-4-il]metanol
- (165) N-(4-metil-5-nitropiridin-2-il)kinoksalin-2-amin
- (166) N-(4-metoksifenil)-4-(4-metilpiperazin-1-il)kinolin-7-amin
- (167) 4-metoksi-N-[4-(trifluormetoksi)fenil]kinolin-7-amin
- (168) N-(4-metilpiridin-2-il)-4-(morfolin-4-il)kinolin-7-amin
- i njihove farmaceutski prihvatljive soli.
9. Spoj prema bilo kojem od zahtjeva 5, 6, i 7, naznačen time što je navedeni spoj odabran između spojeva:
- (10) (3-Metoksi-piridin-2-il)-kinolin-3-il-amin
- (11) Kinolin-3-il-(5-trifluormetil-piridin-2-il)-amin
- (12) (5-Nitro-piridin-2-il)-kinolin-3-il-amin
- (13) (5-Metil-piridin-2-il)-kinolin-3-il-amin
- (14) 2-(Kinolin-3-ilamino)-izonikotinska kiselina
- (15) Kinolin-6-il-(5-trifluormetil-piridin-2-il)-amin
- (16) (6-Metil-piridin-2-il)-kinolin-6-il-amin
- (105) N-(6-metilpiridin-2-il)kinolin-3-amin
- (106) N-(3-nitropiridin-2-il)kinolin-3-amin
- (107) N-(5-metilpiridin-2-il)kinolin-6-amin
- (108) N-(3-metoksipiridin-2-il)kinolin-6-amin
- (119) 8-klor-N-(piridin-4-il)kinolin-2-amin
- (124) N-[4-(trifluormetoksi)fenil]kinoksalin-2-amin
- (125) N-[2-metil-4-(trifluormetoksi)fenil]kinoksalin-2-amin
- (126) N-[3-(trifluormetoksi)fenil]kinoksalin-2-amin
- (127) N-[2-(trifluormetoksi)fenil]kinoksalin-2-amin
- (128) N-(pirimidin-2-il)kinolin-2-amin
- (129) 8-klor-N-(pirimidin-2-il)kinolin-2-amin
- (130) 4-metil-N-(pirimidin-2-il)kinolin-2-amin
- (135) N-(piridin-2-il)kinoksalin-2-amin
- (136) N-(4-metilpiridin-2-il)kinoksalin-2-amin
- (137) 6-(kinoksalin-2-ilamino)piridin-3-karbonitril
- (138) N-(6-metilpiridin-2-il)kinoksalin-2-amin
- (139) N-(4-metilpiridin-2-il)-3-(trifluormetil)kinoksalin-2-amin
- (140) N-(3,5-diklor-4-metilpiridin-2-il)kinoksalin-2-amin
- (141) N-(4-metil-3-nitropiridin-2-il)kinoksalin-2-amin
- (145) 4-metoksi-N-(piridin-2-il)kinolin-7-amin
- (146) 4-metoksi-N-(4-metilpiridin-2-il)kinolin-7-amin
- (147) 4-N,4-N-dimetil-7-N-(4-metilpiridin-2-il)kinolin-4,7-diamin
- (159) N-(3-aminopiridin-2-il)kinolin-3-amin
- (160) 6-klor-N-(4-metilpiridin-2-il)kinoksalin-2-amin
- (161) N-(4-etilpiridin-2-il)kinoksalin-2-amin
- (162) N-(5-bromo-4-metilpiridin-2-il)kinoksalin-2-amin
- (163) N-(4,6-dimetilpiridin-2-il)kinoksalin-2-amin
- (164) [2-(kinoksalin-2-ilamino)piridin-4-il]metanol
- (165) N-(4-metil-5-nitropiridin-2-il)kinoksalin-2-amin, i
- (168) N-(4-metilpiridin-2-il)-4-(morfolin-4-il)kinolin-7-amin
kao i njihove farmaceutski prihvatljive soli, kao što su hidroklorid, hidrobromid, tartrat, fumarat, citrat, trifluoracetat, askorbat, triflat, mezilat, tozilat, format, acetat i malat.
10. Farmaceutski pripravak naznačen time što sadrži najmanje jedan spoj kako je definiran u bilo kojem od zahtjeva 5, 6, 7 i 9.
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EP20090305540 EP2266972A1 (en) | 2009-06-12 | 2009-06-12 | New chemical molecules that inhibit the splicing mechanism for treating diseases resulting from splicing anomalies |
EP09162630A EP2261214A1 (en) | 2009-06-12 | 2009-06-12 | Compounds useful to treat premature aging and in particular progeria |
PCT/IB2010/052652 WO2010143170A2 (en) | 2009-06-12 | 2010-06-14 | Compounds useful for treating premature aging and in particular progeria |
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HRP20230143TT HRP20230143T1 (hr) | 2009-06-12 | 2010-06-14 | Nove kemijske molekule koje inhibiraju mehanizam prekrajanja za liječenje bolesti koje su posljedica defekata prekrajanja |
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