HRP20131174T1 - Derivati pirazola, upotrijebljeni kao antagonisti receptora ccr4 - Google Patents
Derivati pirazola, upotrijebljeni kao antagonisti receptora ccr4 Download PDFInfo
- Publication number
- HRP20131174T1 HRP20131174T1 HRP20131174AT HRP20131174T HRP20131174T1 HR P20131174 T1 HRP20131174 T1 HR P20131174T1 HR P20131174A T HRP20131174A T HR P20131174AT HR P20131174 T HRP20131174 T HR P20131174T HR P20131174 T1 HRP20131174 T1 HR P20131174T1
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- Croatia
- Prior art keywords
- methyl
- amino
- methyloxy
- chloro
- phenyl
- Prior art date
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- 102000004498 CCR4 Receptors Human genes 0.000 title 1
- 108010017317 CCR4 Receptors Proteins 0.000 title 1
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 45
- -1 CF 3 Chemical group 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 16
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 15
- 229910003827 NRaRb Inorganic materials 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 150000004675 formic acid derivatives Chemical class 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 206010010741 Conjunctivitis Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- YTEVTHHGQMUPHC-UHFFFAOYSA-N n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-2-hydroxy-2-methylpropanamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(=O)C(C)(C)O)=C1 YTEVTHHGQMUPHC-UHFFFAOYSA-N 0.000 claims 2
- XFROBWVHVSYXPV-UHFFFAOYSA-N n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-4-methylmorpholine-3-carboxamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)C1COCCN1C XFROBWVHVSYXPV-UHFFFAOYSA-N 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- JEJJUQUUMJJQQX-CQSZACIVSA-N (2R)-N-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-hydroxyindazol-1-yl]methyl]phenyl]methyl]-2-(methylamino)propanamide Chemical compound CN[C@H](C)C(=O)NCc1cccc(Cn2nc(NS(=O)(=O)c3ccc(Cl)s3)c3c(O)cccc23)c1 JEJJUQUUMJJQQX-CQSZACIVSA-N 0.000 claims 1
- FORGMRSGVSYZQR-RXMQYKEDSA-N (2r)-2-amino-4-methylpentanamide Chemical compound CC(C)C[C@@H](N)C(N)=O FORGMRSGVSYZQR-RXMQYKEDSA-N 0.000 claims 1
- SMOUHOKXMPPVCJ-HSZRJFAPSA-N (2r)-2-amino-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-3-methylbutanamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(=O)[C@H](N)C(C)C)=C1 SMOUHOKXMPPVCJ-HSZRJFAPSA-N 0.000 claims 1
- WYXWNKVZQZVCJA-PFEQFJNWSA-N (2r)-2-amino-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]propanamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(=O)[C@@H](C)N)=C1 WYXWNKVZQZVCJA-PFEQFJNWSA-N 0.000 claims 1
- ZCIHPFPJWDAACP-XFULWGLBSA-N (2r)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-2-(methylamino)propanamide;hydrochloride Chemical compound Cl.CN[C@H](C)C(=O)NCC1=CC=CC(CN2C3=CC=CC(OC)=C3C(NS(=O)(=O)C=3SC(Cl)=CC=3)=N2)=C1 ZCIHPFPJWDAACP-XFULWGLBSA-N 0.000 claims 1
- OONZRGJSUJYHAB-AREMUKBSSA-N (2r)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-2-methylpyrrolidine-2-carboxamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@@]1(C)CCCN1 OONZRGJSUJYHAB-AREMUKBSSA-N 0.000 claims 1
- YMLPECCSQYHITL-UNTBIKODSA-N (2r)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]azetidine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@H]1CCN1 YMLPECCSQYHITL-UNTBIKODSA-N 0.000 claims 1
- OVJHSSHYAAFCOP-FSRHSHDFSA-N (2r)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]piperidine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@H]1CCCCN1 OVJHSSHYAAFCOP-FSRHSHDFSA-N 0.000 claims 1
- HOXRLBOCYGYFRT-GMUIIQOCSA-N (2r)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]pyrrolidine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@H]1CCCN1 HOXRLBOCYGYFRT-GMUIIQOCSA-N 0.000 claims 1
- QQRBDVAZANWLSZ-XFULWGLBSA-N (2r)-n-[[4-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-2-(methylamino)propanamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(CNC(=O)[C@@H](C)NC)=CC=C1CN1C2=CC=CC(OC)=C2C(NS(=O)(=O)C=2SC(Cl)=CC=2)=N1 QQRBDVAZANWLSZ-XFULWGLBSA-N 0.000 claims 1
- NDTHOKJMKHZVNC-NTISSMGPSA-N (2s)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-2-(dimethylamino)propanamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(=O)[C@H](C)N(C)C)=C1 NDTHOKJMKHZVNC-NTISSMGPSA-N 0.000 claims 1
- QJSXGCHBKRJQEV-AWEZNQCLSA-N (2s)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-2-hydroxypropanamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(=O)[C@H](C)O)=C1 QJSXGCHBKRJQEV-AWEZNQCLSA-N 0.000 claims 1
- YMLPECCSQYHITL-LMOVPXPDSA-N (2s)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]azetidine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@@H]1CCN1 YMLPECCSQYHITL-LMOVPXPDSA-N 0.000 claims 1
- VOMNVECKPIKEGA-LMOVPXPDSA-N (3S)-N-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-hydroxyindazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide formic acid Chemical compound OC=O.Oc1cccc2n(Cc3cccc(CNC(=O)[C@@H]4COCCN4)c3)nc(NS(=O)(=O)c3ccc(Cl)s3)c12 VOMNVECKPIKEGA-LMOVPXPDSA-N 0.000 claims 1
- IEAVANINUGTOTB-ALAWQYECSA-N (3r)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-(1-hydroxyethyl)indazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide;formic acid Chemical compound OC=O.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(C(O)C)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@H]1COCCN1 IEAVANINUGTOTB-ALAWQYECSA-N 0.000 claims 1
- VGUBWOBIVNWEBV-VEIFNGETSA-N (3r)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-(2-hydroxypropan-2-yl)indazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide;formic acid Chemical compound OC=O.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(C(C)(O)C)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@H]1COCCN1 VGUBWOBIVNWEBV-VEIFNGETSA-N 0.000 claims 1
- FQIHUDSDZFBNPZ-GMUIIQOCSA-N (3r)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide;hydrochloride Chemical compound Cl.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@H]1COCCN1 FQIHUDSDZFBNPZ-GMUIIQOCSA-N 0.000 claims 1
- AKTRFRDCQLWUNG-GOSISDBHSA-N (3r)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-5-fluoro-4-methoxyindazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=C(F)C=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@H]1COCCN1 AKTRFRDCQLWUNG-GOSISDBHSA-N 0.000 claims 1
- GWZKMKFTPDGWLG-GOSISDBHSA-N (3r)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-6-fluoro-4-methoxyindazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC(F)=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@H]1COCCN1 GWZKMKFTPDGWLG-GOSISDBHSA-N 0.000 claims 1
- HRCZYPGLPBYVRS-HXUWFJFHSA-N (3r)-n-[[3-[[4-methoxy-3-[(5-methylthiophen-2-yl)sulfonylamino]indazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide Chemical compound N1=C(NS(=O)(=O)C=2SC(C)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@H]1COCCN1 HRCZYPGLPBYVRS-HXUWFJFHSA-N 0.000 claims 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 claims 1
- IEAVANINUGTOTB-NEXUVNJBSA-N (3s)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-(1-hydroxyethyl)indazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide;formic acid Chemical compound OC=O.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(C(O)C)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@@H]1COCCN1 IEAVANINUGTOTB-NEXUVNJBSA-N 0.000 claims 1
- DNZAESLDVXHPAD-FQEVSTJZSA-N (3s)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-(2-hydroxypropan-2-yl)indazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(C(C)(O)C)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@@H]1COCCN1 DNZAESLDVXHPAD-FQEVSTJZSA-N 0.000 claims 1
- FQIHUDSDZFBNPZ-FERBBOLQSA-N (3s)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide;hydrochloride Chemical compound Cl.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@@H]1COCCN1 FQIHUDSDZFBNPZ-FERBBOLQSA-N 0.000 claims 1
- AKTRFRDCQLWUNG-SFHVURJKSA-N (3s)-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-5-fluoro-4-methoxyindazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=C(F)C=CC=2N1CC(C=1)=CC=CC=1CNC(=O)[C@@H]1COCCN1 AKTRFRDCQLWUNG-SFHVURJKSA-N 0.000 claims 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 claims 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 claims 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 claims 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 claims 1
- YULQCZINNSWVGN-UHFFFAOYSA-N 1-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-3-ethylurea Chemical compound CCNC(=O)NCC1=CC=CC(CN2C3=CC=CC(OC)=C3C(NS(=O)(=O)C=3SC(Cl)=CC=3)=N2)=C1 YULQCZINNSWVGN-UHFFFAOYSA-N 0.000 claims 1
- IVGOASIEVSAFSO-UHFFFAOYSA-N 1-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-3-propan-2-ylurea Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(=O)NC(C)C)=C1 IVGOASIEVSAFSO-UHFFFAOYSA-N 0.000 claims 1
- ATKNJNGMWIURST-UHFFFAOYSA-N 1-amino-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]cyclobutane-1-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)C1(N)CCC1 ATKNJNGMWIURST-UHFFFAOYSA-N 0.000 claims 1
- GJYQDYUONNSQKP-UHFFFAOYSA-N 1-amino-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]cyclopropane-1-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=1)=CC=CC=1CNC(=O)C1(N)CC1 GJYQDYUONNSQKP-UHFFFAOYSA-N 0.000 claims 1
- CPPPQWJPPSCELE-UHFFFAOYSA-N 1-tert-butyl-3-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]urea Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(=O)NC(C)(C)C)=C1 CPPPQWJPPSCELE-UHFFFAOYSA-N 0.000 claims 1
- PMGKTGDJGAKWJE-UHFFFAOYSA-N 2-[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]-n-methylacetamide Chemical compound CNC(=O)CC1=CC=CC(CN2C3=CC=CC(OC)=C3C(NS(=O)(=O)C=3SC(Cl)=CC=3)=N2)=C1 PMGKTGDJGAKWJE-UHFFFAOYSA-N 0.000 claims 1
- SIBHOWSWIFTOMQ-UHFFFAOYSA-N 2-amino-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-2-methylpropanamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(=O)C(C)(C)N)=C1 SIBHOWSWIFTOMQ-UHFFFAOYSA-N 0.000 claims 1
- SYQFEVWTSNDPCN-UHFFFAOYSA-N 2-amino-n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]acetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(=O)CN)=C1 SYQFEVWTSNDPCN-UHFFFAOYSA-N 0.000 claims 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 claims 1
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- BTSOAFGYNROARI-UHFFFAOYSA-N n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-6-fluoro-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-2-hydroxy-2-methylpropanamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC(F)=CC=2N1CC1=CC=CC(CNC(=O)C(C)(C)O)=C1 BTSOAFGYNROARI-UHFFFAOYSA-N 0.000 claims 1
- DVRDXNNYTRMDGD-UHFFFAOYSA-N n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-6-fluoro-4-methoxyindazol-1-yl]methyl]phenyl]methyl]-4-methylmorpholine-3-carboxamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC(F)=CC=2N1CC(C=1)=CC=CC=1CNC(=O)C1COCCN1C DVRDXNNYTRMDGD-UHFFFAOYSA-N 0.000 claims 1
- GBCHVZPQMAAJPG-UHFFFAOYSA-N n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-6-fluoro-4-methoxyindazol-1-yl]methyl]phenyl]methyl]acetamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC(F)=CC=2N1CC1=CC=CC(CNC(C)=O)=C1 GBCHVZPQMAAJPG-UHFFFAOYSA-N 0.000 claims 1
- ZHPAIQLXCBMDSK-UHFFFAOYSA-N n-[[3-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-7-fluoro-4-methoxyindazol-1-yl]methyl]phenyl]methyl]acetamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=C(F)C=2N1CC1=CC=CC(CNC(C)=O)=C1 ZHPAIQLXCBMDSK-UHFFFAOYSA-N 0.000 claims 1
- VWJNBZCPVKZXCI-UHFFFAOYSA-N n-[[3-[[4-chloro-3-[(5-chlorothiophen-2-yl)sulfonylamino]indazol-1-yl]methyl]phenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=CC(CN2C3=CC=CC(Cl)=C3C(NS(=O)(=O)C=3SC(Cl)=CC=3)=N2)=C1 VWJNBZCPVKZXCI-UHFFFAOYSA-N 0.000 claims 1
- QAQRYSYEHHNVQU-UHFFFAOYSA-N n-[[3-[[4-methoxy-3-(thiophen-2-ylsulfonylamino)indazol-1-yl]methyl]phenyl]methyl]acetamide Chemical compound N1=C(NS(=O)(=O)C=2SC=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(C)=O)=C1 QAQRYSYEHHNVQU-UHFFFAOYSA-N 0.000 claims 1
- SLSOGGUMXMARFH-UHFFFAOYSA-N n-[[3-[[4-methoxy-3-[(5-methylthiophen-2-yl)sulfonylamino]indazol-1-yl]methyl]phenyl]methyl]acetamide Chemical compound N1=C(NS(=O)(=O)C=2SC(C)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=CC(CNC(C)=O)=C1 SLSOGGUMXMARFH-UHFFFAOYSA-N 0.000 claims 1
- SZTZWHBQSDZDGV-UHFFFAOYSA-N n-[[4-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]acetamide Chemical compound N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC1=CC=C(CNC(C)=O)C=C1 SZTZWHBQSDZDGV-UHFFFAOYSA-N 0.000 claims 1
- SLTQMZJSZOLLCM-UHFFFAOYSA-N n-[[4-[[3-[(5-chlorothiophen-2-yl)sulfonylamino]-4-methoxyindazol-1-yl]methyl]phenyl]methyl]morpholine-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(NS(=O)(=O)C=2SC(Cl)=CC=2)C=2C(OC)=CC=CC=2N1CC(C=C1)=CC=C1CNC(=O)C1COCCN1 SLTQMZJSZOLLCM-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 230000001717 pathogenic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000001932 seasonal effect Effects 0.000 claims 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 claims 1
- 230000008313 sensitization Effects 0.000 claims 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 208000001319 vasomotor rhinitis Diseases 0.000 claims 1
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Claims (16)
1. Spoj formule (I), ili njegova sol
[image]
,
naznačen time što
R1 se bira iz skupine koju čine (1), (2), (3) (4) i (5)
(1) skupina formule (a)
[image]
,
gdje se A bira iz skupine koju čine (i), (ii), (iii), (iv), (v), (vi), (vii) i (viii)
(i) vodik;
(ii) C1-6alkil, izborno supstituiran s jednom ili više skupina -NRaRb, -ORc, -C(O)NRaRb, -C(O)ORc, heterociklilnih, fenilnih ili heteroarilnih skupine;
(iii) C3-7cikloalkil, izborno supstituiran sa skupinom -C(O)ORc ili -NRaRb;
(iv) heterociklil, izborno supstituiran s jednim ili više C1-6alkila;
(v) heteroaril, izborno supstituiran s jednim ili više halogena ili C1-6alkila;
(vi) -NRaRb;
(vii) fenil, supstituiran sa skupinom -(CH2)pC(O)OH, gdje je p 0, 1, 2 ili 3; ili
(viii) -(CH2)7C(O)OH;
(2) skupina formule (b)
[image]
,
gdje je B C1-6alkil;
(3) -C(O)NRaRb ili -CH2C(O)NRaRb;
(4) -S(O)2NRaRb;
Ra, Rb i Rc su neovisno vodik ili C1-6alkil;
R2 je halogen, C1-6alkil, CF3, hidroksi ili C1-6alkoksi;
R3 je halogen, CF3, hidroksi, C1-6alkoksi, CRdReOH ili CHF2; gdje su Rd i Re neovisno vodik ili metil;
R4 je vodik, halogen, C1-6alkil ili CF3;
R5 i R6 su neovisno vodik, halogen ili C1-6alkil; i
n je 0 ili 1.
2. Spoj u skladu s patentnim zahtjevom 1, ili njegova sol, naznačen time što
R1 se bira iz skupine koju čine (1), (2), (3) (4) i (5)
(1) skupina formule (a)
[image]
,
gdje se A bira iz skupine koju čine (i), (ii), (iii), (iv), (v) i (vi):
(i) vodik;
(ii) C1-6alkil, izborno supstituiran s jednom ili više skupina -NRaRb, -ORc, C(O)NRaRb, -C(O)ORc, heterociklilnih, fenilnih ili heteroarilnih skupina;
(iii) C3-7cikloalkil, izborno supstituiran sa skupinom -NRaRb;
(iv) heterociklil, izborno supstituiran s jednim ili više C1-6alkila;
(v) heteroaril, izborno supstituiran s jednim ili više halogena ili C1-6alkila;
(vi) -NRaRb;
(2) skupina formule (b)
[image]
,
gdje je B C1-6alkil;
(3) -C(O)NRaRb;
(4) -S(O)2NRaRb;
(5) C1-6alkoksi, izborno supstituiran s NRaRb;
Ra, Rb i Rc su neovisno vodik ili C1-6alkil;
R2 je halogen, C1-6alkil, CF3, hidroksi ili C1-6alkoksi;
R3 je halogen, CF3, hidroksil, C1-8alkoksi, CH2OH ili CHF2;
R4 je vodik, halogen, C1-6alkil ili CF3;
R5 i R6 su neovisno vodik, halogen ili C1-6alkil; i
n je 0 ili 1.
3. Spoj u skladu s patentnim zahtjevom 1 ili patentni zahtjev 2, naznačen time što je spoj formule (Ia) ili njegova sol
[image]
,
gdje su R1 i R3 definirani kao u patentnom zahtjevu 1 ili patentnom zahtjevu 2.
4. Spoj u skladu s bilo koji od patentnih zahtjeva 1-3, ili njegova sol, naznačen time što je R1 skupina formule (a)
[image]
.
5. Spoj u skladu s patentnim zahtjevom 4, ili njegova sol, naznačen time što je A C1-6alkil.
6. Spoj u skladu s patentnim zahtjevom 4, ili njegova sol, naznačen time što je A C1-6alkil, supstituiran s jednim ili više -NRaRb, -ORc, -C(O)NRaRb, -C(O)ORc, pirolidinila, fenila ili imidazolila.
7. Spoj u skladu s patentnim zahtjevom 4, ili njegova sol, naznačen time što je A heterociklil, kojeg se bira iz skupine koju čine pirolidinil, piperidinil i morfolinil.
8. Spoj u skladu s patentnim zahtjevom 4, ili njegova sol, naznačen time što je A heteroaril, kojeg se bira iz skupine koju čine furil, imidazolil, pirazolil i oksazolil.
9. Spoj u skladu s bilo koji od patentnih zahtjeva 1-8, ili njegova sol, naznačen time što je R3 metoksi.
10. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je bilo koji od Primjera 1-166 (nabrojanih niže) ili njihovih soli:
Primjer 1
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]acetamid
Primjer 2
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]propanamid
Primjer 3
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-metilpropanamid
Primjer 4
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2,2-dimetilpropanamid
Primjer 5
5-klor-N-[1-({3-[(formilamino)metil]fenil}metil)-4-(metiloksi)-1H-indazol-3-il]-2-tiofensulfonamid
Primjer 6
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-3-morfolinkarboksamid-trifluoracetat
Primjer 7
(3R)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-3-morfolinkarboksamid-hidroklorid
Primjer 8
(3S)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-3-morfolinkarboksamid-hidroklorid
Primjer 9
trifluoracetatna sol (2R)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-piperidinkarboksamida
Primjer 10
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N2-metil-d-alaninamid-hidroklorid
Primjer 11
3-amino-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2,2-dimetilpropanamid-hidroklorid
Primjer 12
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N2-metilglicinamid-hidroklorid
Primjer 13
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-metil-d-prolinamid
Primjer 14
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-metil-2-piperidinkarboksamid
Primjer 15
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-(metilamino)ciklopropankarboksamid-hidroklorid
Primjer 16
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-piperazinkarboksamid-hidroklorid
Primjer 17
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N2-metil-1-alaninamid-trifluoracetat
Primjer 18
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-alaninamid-trifluoracetat
Primjer 19
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-d-alaninamid-trifluoracetat
Primjer 20
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]glicinamid-trifluoracetat
Primjer 21
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]propandiamid
Primjer 22
N4-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N1-metil-1-aspartamid-trifluoracetat
Primjer 23
metil-N4-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]asparaginat-trifluoracetat
Primjer 24
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-(2-pirolidinil)acetamid-trifluoracetat
Primjer 25
3-amino-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]butanamid-trifluoracetat
Primjer 26
3-amino-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-metilpropanamid-trifluoracetat
Primjer 27
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-metil-1-prolinamid-trifluoracetat
Primjer 28
(4S)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-4-fluor-1-prolinamid-trifluoracetat
Primjer 29
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N3-metil-β-alaninamid-trifluoracetat
Primjer 30
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-(metiloksi)acetamid
Primjer 31
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N2,N2-dimetilalaninamid-trifluoracetat
Primjer 32
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-hidroksiacetamid
Primjer 33
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil}metil]-1H-pirazol-4-karboksamid
Primjer 34
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N2,N2,2-trimetilalaninamid-trifluoracetat
Primjer 35
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]tetrahidro-3-furankarboksamid
Primjer 36
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N2-metil-N2-[2-(metiloksi)etil]glicinamid-trifluoracetat
Primjer 37
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-hidroksipropanamid
Primjer 38
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1,3-oksazol-5-karboksamid
Primjer 39
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-metil-1-prolinamid-trifluoracetat
Primjer 40
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-metil-d-prolinamid-trifluoracetat
Primjer 41
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-3-furankarboksamid
Primjer 42
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-metil-2-piperidinkarboksamid-trifluoracetat
Primjer 43
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]tetrahidro-2H-piran-4-karboksamid
Primjer 44
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-histidinamid
Primjer 45
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-d-leucinamid
Primjer 46
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-d-aloizoleucinamid
Primjer 47
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-fenilalaninamid
Primjer 48
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-d-valinamid
Primjer 49
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-lizinamid
Primjer 50
(2R)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-azetidinkarboksamid-trifluoracetat
Primjer 51
(2S)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-piperidinkarboksamid-trifluoracetat
Primjer 52
(4R)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-4-fluor-1-prolinamid-trifluoracetat
Primjer 53
N-[1-{[3,4-bis(metiloksi)fenil]metil}-4-(metiloksi)-1H-indazol-3-il]-5-klor-2-tiofensulfonamid
Primjer 54
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-O-metilserinamid-trifluoracetat
Primjer 55
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-9-il]metil}fenil)metil]-4,4-difluor-d-prolinamid-trifluoracetat
Primjer 56
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N2,2-dimetilalaninamid-formijat
Primjer 57
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-hidroksi-2-metilpropanamid
Primjer 58
5-klor-N-{4-(metiloksi)-1-[(3-{[(metilsulfonil)amino]metil}fenil)metil]-1H-indazol-3-il}-2-tiofensulfonamid
Primjer 59
N-[1-[(3-{[(aminokarbonil)amino]metil}fenil)metil]-4-(metiloksi)-1H-indazol-3-il]-5-klor-2-tiofensulfonamid
Primjer 60
5-klor-N-[1-({3-[({[(1,1-dimetiletil)amino]karbonil}amino)metil]fenil}metil)-4-(metiloksi)-1H-indazol-3-il]-2-tiofensulfonamid
Primjer 61
5-klor-N-[1-({3-[({[(1-metiletil)amino]karbonil}amino)metil]fenil}metil)-4-(metiloksi)-1H-indazol-3-il]-2-tiofensulfonamid
Primjer 62
N-[1-{[4-(aminosulfonil)fenil]metil}-4-(metiloksi)-1H-indazol-3-il]-5-klor-2-tiofensulfonamid
Primjer 63
2-(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)-N-metilacetamid
Primjer 64
3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}benzamid
Primjer 65
3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}-N-[2-(dimetilamino)etil]benzamid
Primjer 66
3-[(4-(metiloksi)-3-{[(5-metil-2-tienil)sulfonil]amino}-1H-indazol-1-il)metil]benzamid
Primjer 67
3-{[3-{[(5-brom-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}benzamid
Primjer 68
3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-7-fluor-4-(metiloksi)-1H-indazol-1-il]metil}benzamid
Primjer 69
3-[(3-{[(5-klor-2-tienil)sulfonil]amino}-7-fluor-4-hidroksi-1H-indazol-1-il)metil]benzamid
Primjer 70
3-[(3-{[(5-klor-2-tienil)sulfonil]amino}-4-hidroksi-1H-indazol-1-il)metil]benzamid
Primjer 71
sol N1-({3-[(3-{[(5-klor-2-tienil)sulfonil]amino}-4-hidroksi-1H-indazol-1-il)metil]fenil}metil)-N2-metil-d-alaninamida s mravljom kiselinom
Primjer 72
N-({3-[(3-{[(5-klor-2-tienil)sulfonil]amino}-4-hidroksi-1H-indazol-1-il)metil]fenil}metil)acetamid
Primjer 73
formijatna sol N-({3-[(3-{[(5-klor-2-tienil)sulfonil]amino}-4-hidroksi-1H-indazol-1-il}metil]fenil}metil)-3-morfolinkarboksamida
Primjer 74
5-klor-N-[1-[(3-{[2-(dimetilamino)etil]oksi}fenil)metil]-4-(metiloksi)-1H-indazol-3-il]-2-tiofensulfonamid
Primjer 75
5-klor-N-[1-[(4-{[2-(dimetilamino)etil]oksi}fenil)metil]-4-(metiloksi)-1H-indazol-3-il]-2-tiofensulfonamid
Primjer 76
5-klor-N-[1-{[4-{[2-(dimetilamino)etil]oksi}-3-(metiloksi)fenil]metil}-4-(metiloksi)-1H-indazol-3-il]-2-tiofensulfonamid
Primjer 77
N-[1-{[3-(aminosulfonil)fenil]metil}-4-(metiloksi)-1H-indazol-3-il]-5-klor-2-tiofensulfonamid
Primjer 78
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil}metil]-β-alaninamid-trifluoracetat
Primjer 79
formijatna sol N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-glutamamida
Primjer 80
N4-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-asparagin-trifluoracetat
Primjer 81
1,1-dimetiletil-N4-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-asparaginat-trifluoracetat
Primjer 82
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-d-prolinamid-trifluoracetat
Primjer 83
1-amino-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]ciklobutankarboksamid-trifluoracetat
Primjer 84
1-amino-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]ciklopropankarboksamid-trifluoracetat
Primjer 85
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N2-metilglicinamid-trifluoracetat
Primjer 86
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N2,N2-dimetilglicinamid-trifluoracetat
Primjer 87
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-3-(metiloksi)propanamid
Primjer 88
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1H-pirol-3-karboksamid
Primjer 89
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]tetrahidro-2-furankarboksamid
Primjer 90
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1,3-oksazol-4-karboksamid
Primjer 91
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1H-pirazol-3-karboksamid
Primjer 92
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1H-pirol-2-karboksamid
Primjer 93
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1H-imidazol-2-karboksamid
Primjer 94
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1H-imidazol-4-karboksamid
Primjer 95
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-furankarboksamid
Primjer 96
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-4-metil-3-morfolinkarboksamid
Primjer 97
N-[(4-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]acetamid
Primjer 98
N-[(4-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-3-morfolinkarboksamid-trifluoracetat
Primjer 99
N1-[(4-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-N2-metil-d-alaninamid-trifluoracetat
Primjer 100
3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}-N-metilbenzamid
Primjer 101
3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}-N,N-dimetilbenzamid
Primjer 102
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-serinamid
Primjer 103
4-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}benzamid
Primjer 104
5-klor-N-(4-(metiloksi)-1-{[4-(metiloksi)fenil]metil}-1H-indazol-3-il)-2-tiofensulfonamid
Primjer 105
5-klor-N-(4-(metiloksi)-1-{[2-(metiloksi)fenil]metil}-1H-indazol-3-il)-2-tiofensulfonamid
Primjer 106
5-klor-N-[1-({3-[(metilamino)sulfonil]fenil}metil)-4-(metiloksi)-1H-indazol-3-il]-2-tiofensulfonamid
Primjer 107
5-klor-N-[1-({3-[(dimetilamino)sulfonil]fenil}metil)-4-(metiloksi)-1H-indazol-3-il]-2-tiofensulfonamid
Primjer 108
3-({4-(metiloksi)-3-[(2-tienilsulfonil)amino]-1H-indazol-1-il}metil)benzamid
Primjer 109
3-{[3-{[(4,5-diklor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}benzamid
Primjer 110
5-klor-N-[1-{[3-{[2-(dimetilamino)etil]oksi}-4-(metiloksi)fenil]metil}-4-(metiloksi)-1H-indazol-3-il]-2-tiofensulfonamid
Primjer 111
formijatna sol (3R)-N-({3-[(3-{[(5-klor-2-tienil)sulfonil]amino}-4-hidroksi-1H-indazol-1-il)metil]fenil}metil)-3-morfolinkarboksamida
Primjer 112
formijatna sol N1-({3-[(3-{[(5-klor-2-tienil)sulfonil]amino}-4-hidroksi-1H-indazol-1-il)metil]fenil}metil)-N2-metilglicinamida
Primjer 113
5-klor-N-[1-{[3-({[(etilamino)karbonil]amino}metil)fenil]metil}-4-(metiloksi)-1H-indazol-3-il]-2-tiofensulfonamid
Primjer 114
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-triptofanamid
Primjer 115
formijatna sol N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-d-alotreoninamida
Primjer 116
N-{[3-({4-(metiloksi)-3-[(2-tienilsulfonil)amino]-1H-indazol-1-il}metil)fenil]metil}acetamid
Primjer 117
4-[(4-(metiloksi)-3-{[(5-metil-2-tienil)sulfonil]amino}-1H-indazol-1-il}metil]benzamid
Primjer 118
N-[1-{[3,4-bis(metiloksi)fenil]metil}-4-(metiloksi)-1H-indazol-3-il]-5-metil-2-tiofensulfonamid
Primjer 119
N-({3-[(4-(metiloksi)-3-{[(5-metil-2-tienil)sulfonil]amino}-1H-indazol-1-il)metil]fenil}metil)acetamid
Primjer 120
(3R)-N-({4-[(4-(metiloksi)-3-{[(5-metil-2-tienil)sulfonil]amino}-1H-indazol-1-il)metil]fenil}metil)-3-morfolinkarboksamid-trifluoracetat
Primjer 121
N-({3-[(3-{[(5-klor-2-tienil)sulfonil]amino}-4-fluor-1H-indazol-1-il)metil]fenil}metil)acetamid
Primjer 122
N-({3-[(4-klor-3-{[(5-klor-2-tienil)sulfonil]amino}-1H-indazol-1-il}metil]fenil}metil)acetamid
Primjer 123
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-4-metil-3-morfolinkarboksamid
Primjeri 124 i 125
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-4-metil-3-morfolinkarboksamid, Enantiomer 1 (Primjer 124) i Enantiomer 2 (Primjer 125)
Primjer 126
(2S)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-hidroksipropanamid (S-enantiomer Primjera 37)
Primjer 127
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-metilalaninamid
Primjer 128
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-7-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]acetamid
Primjer 129
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-6-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]acetamid
Primjer 130
3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-6-fluor-4-(metiloksi)-1H-indazol-1-il]metil}benzamid
Primjer 131
(3R)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-6-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-3-morfolinkarboksamid
Primjer 132
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-6-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-hidroksi-2-metilpropanamid
Primjer 133
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-6-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-4-metil-3-morfolinkarboksamid
Primjer 134
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-5-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]acetamid
Primjer 135
(3S)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-5-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-3-morfolinkarboksamid
Primjer 136
(3R)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-5-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-3-morfolinkarboksamid
Primjer 137
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-5-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-hidroksi-2-metilpropanamid
Primjer 138
4-{[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]amino}-4-oksobutanska kiselina
Primjer 139
5-{[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]amino}-5-oksopentanska kiselina
Primjer 140
6-{[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]amino)-6-oksoheksanska kiselina
Primjer 141
3-{{[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]amino}karbonil)benzojeva kiselina
Primjer 142
4-({[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]amino}karbonil)benzojeva kiselina
Primjer 143
trans-4-({[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]amino}karbonil)cikloheksankarboksilna kiselina
Primjer 144
8-{[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]amino}-8-oksooktanska kiselina
Primjer 145
9-{[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]amino}-9-oksononanska kiselina
Primjer 146
2-({[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]amino}karbonil)benzojeva kiselina
Primjer 147
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(difluormetil)-1H-indazol-1-il]metil}fenil)metil]acetamid
Primjer 148
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(hidroksimetil)-1H-indazol-1-il]metil}fenil)metil]acetamid
Primjer 149
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(1-hidroksietil)-1H-indazol-1-il]metil}fenil)metil]acetamid
Primjer 150
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(1-hidroksi-1-metiletil)-1H-indazol-1-il]metil}fenil)metil]
Primjer 151
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(1-hidroksietil)-1H-indazol-1-il]metil}fenil}metil]-2-hidroksi-2-metilpropanamid
Primjer 152
formijatna sol (3R)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(1-hidroksietil)-1H-indazol-1-il]metil}fenil)metil]-3-morfolinkarboksamida
Primjer 153
formijatna sol (3S)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(1-hidroksietil)-1H-indazol-1-il]metil}fenil}metil]-3-morfolinkarboksamida
Primjer 154
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(1-hidroksi-1-metiletil)-1H-indazol-1-il]metil}fenil)metil]-2-hidroksi-2-metilpropanamid
Primjer 155
formijatna sol (3R)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(1-hidroksi-1-metiletil)-1H-indazol-1-il]metil}fenil)metil]-3-morfolinkarboksamida
Primjer 156
(3S)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(1-hidroksi-1-metiletil)-1H-indazol-1-il]metil}fenil)metil]-3-morfolinkarboksamid
Primjer 157
N1-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-d-serinamid-trifluoracetat
Primjer 158
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-1-prolinamid-trifluoracetat
Primjer 159
(2S)-N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-azetidinkarboksamid-trifluoracetat
Primjer 160
(3R)-N-({3-[(4-(metiloksi)-3-{[(5-metil-2-tienil)sulfonil]amino}-1H-indazol-1-il)metil]fenil}metil)-3-morfolinkarboksamid
Primjer 161
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-5-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-4-metil-3-morfolinkarboksamid, Enantiomer 1
Primjer 162
N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-5-fluor-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-4-metil-3-morfolinkarboksamid, Enantiomer 2
Primjer 163
4-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}-N,N-dietilbenzamid
Primjer 164
5-klor-N-(4-(metiloksi)-1-{[3-(metiloksi)fenil]metil}-1H-indazol-3-il)-2-tiofensulfonamid
Primjer 165
N-[1-{[3-fluor-4-(metiloksi)fenil]metil}-4-(metiloksi)-1H-indazol-3-il]-5-metil-2-tiofensulfonamid
Primjer 166
formijatna sol (3S)-N-({3-[(3-{[(5-klor-2-tienil)sulfonil]amino}-4-hidroksi-1H-indazol-1-il)metil]fenil}metil)-3-morfolinkarboksamida.
11. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je N-[(3-{[3-{[(5-klor-2-tienil)sulfonil]amino}-4-(metiloksi)-1H-indazol-1-il]metil}fenil)metil]-2-hidroksi-2-metilpropanamid
[image]
.
12. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo koji od patentnih zahtjeva 1-11, ili njegovu farmaceutski prihvatljivu sol, i jedan ili više farmaceutski prihvatljivih podloga, razrjeđivača i pomoćnih tvari.
13. Kombinacijski farmaceutski proizvod, naznačen time što sadrži spoj formule (I), ili njegovu farmaceutski prihvatljivu sol, u skladu s bilo koji od patentnih zahtjeva 1-11, uz jedno ili više drugih terapijski aktivnih sredstava.
14. Spoj u skladu s bilo koji od patentnih zahtjeva 1-11, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u terapiji.
15. Spoj u skladu s bilo koji od patentnih zahtjeva 1-11, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u liječenje astme, kronična opstruktivne plućne bolesti (COPD), uključujući kronični bronhitis i emfizem, idiopatske fibroze pluća, atopičnog ili kontaktnog dermatitisa, koprivnjače, alergijskog rinitisa (sezonskog ili cjelogodišnjeg), vazomotornog rinitisa, polipa u nosu, alergijskog konjunktivitisa, proljetnog konjunktivitisa, profesionalnog konjunktivitisa, infektivnog konjunktivitisa, eozinofilnih sindroma, eozinofilnog granuloma, psorijaze, reumatoidnog artritisa, ulceroznog kolitisa, Crohnove bolesti, tromboze, reperfuzijske ozljede miokarda i mozga, kroničnog glomerulonefritisa, sepse, sindroma respiratornog distresa kod odraslih, multiple skleroze, poremećaja pamćenja (uključujući Alzheimerovu bolest), boli i raka, alergijske bronhopulmonalne aspergiloze, alergijskog gljivičnog sinusitisa, teške astme uz senzibilizaciju na gljivice i bolesti koje uključuju patogenu ulogu gljivica, uključujući invaziju ili kolonizaciju (poput invazivne aspergiloze, aspergiloma ili kandidijaze).
16. Spoj, ili njegova farmaceutski prihvatljiva sol, namijenjen upotrebi u skladu s patentnim zahtjevom 15, naznačen time što je namijenjen liječenju astme.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| US15570209P | 2009-02-26 | 2009-02-26 | |
| PCT/EP2010/052307 WO2010097395A1 (en) | 2009-02-26 | 2010-02-24 | Pyrazole derivatives used as ccr4 receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20131174T1 true HRP20131174T1 (hr) | 2014-01-17 |
Family
ID=42110309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20131174AT HRP20131174T1 (hr) | 2009-02-26 | 2013-12-10 | Derivati pirazola, upotrijebljeni kao antagonisti receptora ccr4 |
Country Status (31)
| Country | Link |
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| US (3) | US8304446B2 (hr) |
| EP (1) | EP2401270B1 (hr) |
| JP (1) | JP5520969B2 (hr) |
| KR (1) | KR20110128896A (hr) |
| CN (1) | CN102388039B (hr) |
| AR (1) | AR075594A1 (hr) |
| AU (2) | AU2010217629A1 (hr) |
| BR (1) | BRPI1013396A2 (hr) |
| CA (1) | CA2753337A1 (hr) |
| CL (1) | CL2011002103A1 (hr) |
| CO (1) | CO6420342A2 (hr) |
| DK (1) | DK2401270T3 (hr) |
| DO (1) | DOP2011000272A (hr) |
| EA (1) | EA021740B1 (hr) |
| ES (1) | ES2439773T3 (hr) |
| HK (1) | HK1159621A1 (hr) |
| HR (1) | HRP20131174T1 (hr) |
| IL (1) | IL214655A0 (hr) |
| MA (1) | MA33132B1 (hr) |
| MX (1) | MX2011008972A (hr) |
| NZ (1) | NZ594641A (hr) |
| PE (1) | PE20120307A1 (hr) |
| PL (1) | PL2401270T3 (hr) |
| PT (1) | PT2401270E (hr) |
| RS (1) | RS53133B (hr) |
| SG (1) | SG173768A1 (hr) |
| SI (1) | SI2401270T1 (hr) |
| SM (1) | SMT201400001B (hr) |
| TW (1) | TW201041879A (hr) |
| UY (1) | UY32464A (hr) |
| WO (1) | WO2010097395A1 (hr) |
Families Citing this family (16)
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| KR20100055456A (ko) | 2007-08-31 | 2010-05-26 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 다환식 화합물 |
| EP2401277A1 (en) | 2009-02-26 | 2012-01-04 | Eisai R&D Management Co., Ltd. | Salt of tetrahydrotriazolopyridine derivative and crystal thereof |
| CA2753696A1 (en) | 2009-02-26 | 2010-09-02 | Noritaka Kitazawa | Nitrogen-containing fused heterocyclic compounds and their use as beta amyloid production inhibitors |
| US8729260B2 (en) * | 2010-05-19 | 2014-05-20 | Savior Lifetec Corporation | Process for the preparation of carbapenem using cabapenem intermediates and recovery of cabapenem |
| WO2012025473A1 (en) * | 2010-08-24 | 2012-03-01 | Glaxo Group Limited | Cc.chemokine receptor 4 antagonists |
| WO2015127125A1 (en) * | 2014-02-20 | 2015-08-27 | Cornell University | Compounds and methods for inhibiting fascin |
| US10179787B2 (en) * | 2016-07-29 | 2019-01-15 | Flx Bio, Inc. | Chemokine receptor modulators and uses thereof |
| WO2018049271A1 (en) | 2016-09-09 | 2018-03-15 | Flx Bio, Inc. | Chemokine receptor modulators and uses thereof |
| JOP20190192A1 (ar) * | 2017-03-01 | 2019-08-08 | Glaxosmithkline Ip No 2 Ltd | مشتقات بيرازول بوصفها مثبطات برومودومين |
| WO2018187509A1 (en) | 2017-04-04 | 2018-10-11 | Flx Bio, Inc. | Heterocyclic compounds as chemokine receptor modulators |
| KR102615821B1 (ko) * | 2017-04-11 | 2023-12-21 | 선샤인 레이크 파르마 컴퍼니 리미티드 | 불소-치환된 인다졸 화합물 및 이의 용도 |
| JP2021502345A (ja) | 2017-11-06 | 2021-01-28 | ラプト・セラピューティクス・インコーポレイテッド | 抗がん剤 |
| CN110028501B (zh) | 2018-01-12 | 2022-02-22 | 迈德欣国际有限公司 | 化合物及其制备方法和用途 |
| RU2020128176A (ru) | 2018-01-26 | 2022-03-02 | Рапт Терапьютикс, Инк. | Модуляторы рецепторов хемокинов и их применение |
| CN113893220A (zh) * | 2020-07-07 | 2022-01-07 | 迈德欣国际有限公司 | 鼻粘膜给药剂型和其应用 |
| US20230322741A1 (en) | 2022-04-06 | 2023-10-12 | Rapt Therapeutics, Inc. | Chemokine receptor modulators and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| MXPA05005554A (es) * | 2002-12-12 | 2005-07-26 | Aventis Pharma Sa | Derivados de aminoindazol y su utilizacion como inhibidores de quinasas. |
| FR2848554A1 (fr) * | 2002-12-12 | 2004-06-18 | Aventis Pharma Sa | Nouveaux derives d'aminoindazoles a titre de medicaments et compositions pharmaceutiques les renfermant |
| SE0301650D0 (sv) * | 2003-06-04 | 2003-06-04 | Astrazeneca Ab | Novel compounds |
| US20080194557A1 (en) * | 2007-01-18 | 2008-08-14 | Joseph Barbosa | Methods and compositions for the treatment of pain, inflammation and cancer |
-
2010
- 2010-02-24 MA MA34179A patent/MA33132B1/fr unknown
- 2010-02-24 MX MX2011008972A patent/MX2011008972A/es active IP Right Grant
- 2010-02-24 US US12/711,283 patent/US8304446B2/en not_active Expired - Fee Related
- 2010-02-24 BR BRPI1013396A patent/BRPI1013396A2/pt not_active IP Right Cessation
- 2010-02-24 AR ARP100100532A patent/AR075594A1/es not_active Application Discontinuation
- 2010-02-24 UY UY0001032464A patent/UY32464A/es not_active Application Discontinuation
- 2010-02-24 KR KR1020117022518A patent/KR20110128896A/ko not_active Application Discontinuation
- 2010-02-24 AU AU2010217629A patent/AU2010217629A1/en not_active Abandoned
- 2010-02-24 CN CN201080016319.3A patent/CN102388039B/zh not_active Expired - Fee Related
- 2010-02-24 ES ES10705594.9T patent/ES2439773T3/es active Active
- 2010-02-24 PT PT107055949T patent/PT2401270E/pt unknown
- 2010-02-24 NZ NZ594641A patent/NZ594641A/xx not_active IP Right Cessation
- 2010-02-24 TW TW099105340A patent/TW201041879A/zh unknown
- 2010-02-24 SG SG2011059813A patent/SG173768A1/en unknown
- 2010-02-24 PL PL10705594T patent/PL2401270T3/pl unknown
- 2010-02-24 RS RS20130585A patent/RS53133B/en unknown
- 2010-02-24 DK DK10705594.9T patent/DK2401270T3/da active
- 2010-02-24 JP JP2011551485A patent/JP5520969B2/ja not_active Expired - Fee Related
- 2010-02-24 WO PCT/EP2010/052307 patent/WO2010097395A1/en active Application Filing
- 2010-02-24 CA CA2753337A patent/CA2753337A1/en not_active Abandoned
- 2010-02-24 SI SI201030466T patent/SI2401270T1/sl unknown
- 2010-02-24 EP EP10705594.9A patent/EP2401270B1/en active Active
- 2010-02-24 PE PE2011001557A patent/PE20120307A1/es not_active Application Discontinuation
- 2010-02-24 US US13/202,139 patent/US8357716B2/en not_active Expired - Fee Related
- 2010-02-24 EA EA201190142A patent/EA021740B1/ru not_active IP Right Cessation
-
2011
- 2011-08-15 IL IL214655A patent/IL214655A0/en unknown
- 2011-08-25 DO DO2011000272A patent/DOP2011000272A/es unknown
- 2011-08-26 CL CL2011002103A patent/CL2011002103A1/es unknown
- 2011-08-26 CO CO11109505A patent/CO6420342A2/es active IP Right Grant
-
2012
- 2012-01-04 HK HK12100042.4A patent/HK1159621A1/xx not_active IP Right Cessation
- 2012-10-02 US US13/633,382 patent/US8507543B2/en not_active Expired - Fee Related
-
2013
- 2013-12-10 HR HRP20131174AT patent/HRP20131174T1/hr unknown
-
2014
- 2014-01-03 SM SM201400001T patent/SMT201400001B/xx unknown
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2016
- 2016-06-02 AU AU2016203684A patent/AU2016203684A1/en not_active Abandoned
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