HRP20100675T1 - Derivati pirazola kao modulatori protein kinaze - Google Patents
Derivati pirazola kao modulatori protein kinaze Download PDFInfo
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- HRP20100675T1 HRP20100675T1 HR20100675T HRP20100675T HRP20100675T1 HR P20100675 T1 HRP20100675 T1 HR P20100675T1 HR 20100675 T HR20100675 T HR 20100675T HR P20100675 T HRP20100675 T HR P20100675T HR P20100675 T1 HRP20100675 T1 HR P20100675T1
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- Prior art keywords
- phenyl
- pyrazol
- group
- chloro
- compound according
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- 102000001253 Protein Kinase Human genes 0.000 title 1
- 108060006633 protein kinase Proteins 0.000 title 1
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 27
- 125000005647 linker group Chemical group 0.000 claims abstract 27
- 125000001424 substituent group Chemical group 0.000 claims abstract 26
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 22
- 239000001257 hydrogen Substances 0.000 claims abstract 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 18
- 125000004429 atom Chemical group 0.000 claims abstract 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 17
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 15
- -1 pyrrolidinocarbonyl Chemical group 0.000 claims abstract 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 10
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 9
- 239000000460 chlorine Substances 0.000 claims abstract 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 9
- 239000011737 fluorine Substances 0.000 claims abstract 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 8
- 150000001204 N-oxides Chemical class 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 239000012453 solvate Substances 0.000 claims abstract 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 6
- 125000004423 acyloxy group Chemical group 0.000 claims abstract 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 5
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000002252 acyl group Chemical group 0.000 claims abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract 4
- 239000001301 oxygen Substances 0.000 claims abstract 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract 4
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 125000004442 acylamino group Chemical group 0.000 claims abstract 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 125000004122 cyclic group Chemical group 0.000 claims abstract 2
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 2
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 150000002431 hydrogen Chemical group 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 150000001721 carbon Chemical group 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 230000002265 prevention Effects 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- IVDLDHJBOWQROZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-methyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNC)C1=CC=C(Cl)C=C1 IVDLDHJBOWQROZ-UHFFFAOYSA-N 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- HWVGILTYGZFGLR-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CN)C1=CC=C(Cl)C=C1 HWVGILTYGZFGLR-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- SSRZUATVJOAMJJ-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)-[4-(1h-pyrazol-4-yl)phenyl]methyl]piperazine Chemical compound C1=C(Cl)C(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)N1CCNCC1 SSRZUATVJOAMJJ-UHFFFAOYSA-N 0.000 claims 2
- MGYPCCQLBPTNML-UHFFFAOYSA-N 1-[(4-chlorophenyl)-[4-(1h-pyrazol-4-yl)phenyl]methyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)N1CCNCC1 MGYPCCQLBPTNML-UHFFFAOYSA-N 0.000 claims 2
- HBYQXDUYJRDECS-UHFFFAOYSA-N 2-[[2-(4-chlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethyl]amino]ethanol Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNCCO)C1=CC=C(Cl)C=C1 HBYQXDUYJRDECS-UHFFFAOYSA-N 0.000 claims 2
- IIRWNGPLJQXWFJ-UHFFFAOYSA-N 2-amino-1-(4-chlorophenyl)-1-[4-(1h-pyrazol-4-yl)phenyl]ethanol Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(O)(CN)C1=CC=C(Cl)C=C1 IIRWNGPLJQXWFJ-UHFFFAOYSA-N 0.000 claims 2
- QLJLUDCLPSRPFI-UHFFFAOYSA-N 3-[[2-(4-chlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethyl]amino]propan-1-ol Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNCCCO)C1=CC=C(Cl)C=C1 QLJLUDCLPSRPFI-UHFFFAOYSA-N 0.000 claims 2
- 102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 claims 2
- 108010049894 Cyclic AMP-Dependent Protein Kinases Proteins 0.000 claims 2
- 206010016935 Follicular thyroid cancer Diseases 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 108091008611 Protein Kinase B Proteins 0.000 claims 2
- 102000005765 Proto-Oncogene Proteins c-akt Human genes 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 201000005787 hematologic cancer Diseases 0.000 claims 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims 2
- BSDJRCSCDXPNOO-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(methylamino)-1-[4-(1h-pyrazol-4-yl)phenyl]ethanol Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(O)(CNC)C1=CC=C(Cl)C=C1 BSDJRCSCDXPNOO-UHFFFAOYSA-N 0.000 claims 1
- YPAHULZLTKIWQR-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethyl]imidazole Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)CN1C=NC=C1 YPAHULZLTKIWQR-UHFFFAOYSA-N 0.000 claims 1
- HLVUQRHDBODCFJ-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)CN1CCNCC1 HLVUQRHDBODCFJ-UHFFFAOYSA-N 0.000 claims 1
- XGMBCVUAPHUSMA-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethyl]piperidine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)CN1CCCCC1 XGMBCVUAPHUSMA-UHFFFAOYSA-N 0.000 claims 1
- FVHKVHULVJSUGS-UHFFFAOYSA-N 1-[3-(4-chlorophenyl)-3-[4-(1h-pyrazol-4-yl)phenyl]propyl]imidazole Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)CCN1C=NC=C1 FVHKVHULVJSUGS-UHFFFAOYSA-N 0.000 claims 1
- YMOIUHMRAZGIKG-UHFFFAOYSA-N 1-[3-phenoxy-3-[4-(1h-pyrazol-4-yl)phenyl]propyl]imidazole Chemical compound C=1C=CC=CC=1OC(C=1C=CC(=CC=1)C1=CNN=C1)CCN1C=CN=C1 YMOIUHMRAZGIKG-UHFFFAOYSA-N 0.000 claims 1
- PVGMKLLGQDLGRJ-UHFFFAOYSA-N 1-methyl-4-[phenyl-[4-(1h-pyrazol-4-yl)phenyl]methyl]-1,4-diazepane Chemical compound C1CN(C)CCCN1C(C=1C=CC(=CC=1)C1=CNN=C1)C1=CC=CC=C1 PVGMKLLGQDLGRJ-UHFFFAOYSA-N 0.000 claims 1
- ALBNOJHFBUICLB-UHFFFAOYSA-N 1-phenyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=CC=CC=1C(N)CC(C=C1)=CC=C1C=1C=NNC=1 ALBNOJHFBUICLB-UHFFFAOYSA-N 0.000 claims 1
- YHDRFTQLBPOIDN-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(CN)C(C=C1)=CC=C1C=1C=NNC=1 YHDRFTQLBPOIDN-UHFFFAOYSA-N 0.000 claims 1
- KTCZKWVYZSCJKV-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C1=C(Cl)C(OC)=CC=C1C(CN)C1=CC=C(C2=CNN=C2)C=C1 KTCZKWVYZSCJKV-UHFFFAOYSA-N 0.000 claims 1
- YVVUEDSXVDPICU-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)-n-methyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(OC)C(Cl)=CC=1C(CNC)C(C=C1)=CC=C1C=1C=NNC=1 YVVUEDSXVDPICU-UHFFFAOYSA-N 0.000 claims 1
- RZQSUNKASWLJQA-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-methyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNC)OC1=CC=CC(Cl)=C1 RZQSUNKASWLJQA-UHFFFAOYSA-N 0.000 claims 1
- JQAPAUAVUKTZPG-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-methyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=CC(Cl)=CC=1C(CNC)C(C=C1)=CC=C1C=1C=NNC=1 JQAPAUAVUKTZPG-UHFFFAOYSA-N 0.000 claims 1
- FSSABRHCBJFDJH-UHFFFAOYSA-N 2-(4-chloro-3-fluorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(Cl)C(F)=CC=1C(CN)C(C=C1)=CC=C1C=1C=NNC=1 FSSABRHCBJFDJH-UHFFFAOYSA-N 0.000 claims 1
- YTIXTVUIMQCOOX-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]acetamide Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(C(=O)N)C1=CC=C(Cl)C=C1 YTIXTVUIMQCOOX-UHFFFAOYSA-N 0.000 claims 1
- OQPBTDKODFFOER-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]morpholine Chemical compound C1=CC(Cl)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)OCCNC1 OQPBTDKODFFOER-UHFFFAOYSA-N 0.000 claims 1
- WJIBOVOTOYHIAY-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-fluoro-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(F)(CN)C1=CC=C(Cl)C=C1 WJIBOVOTOYHIAY-UHFFFAOYSA-N 0.000 claims 1
- KAPLTLJNVKHMLV-UHFFFAOYSA-N 2-(4-chlorophenyl)-n,n-dimethyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CN(C)C)C1=CC=C(Cl)C=C1 KAPLTLJNVKHMLV-UHFFFAOYSA-N 0.000 claims 1
- HGJXGKHMXZTCMI-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(cyclopropylmethyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)CNCC1CC1 HGJXGKHMXZTCMI-UHFFFAOYSA-N 0.000 claims 1
- HBXOAWAFHYIFMJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-ethyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNCC)C1=CC=C(Cl)C=C1 HBXOAWAFHYIFMJ-UHFFFAOYSA-N 0.000 claims 1
- UAALBJPKYVOYRB-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-methyl-2-[4-(1h-pyrazol-4-yl)phenyl]acetamide Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(C(=O)NC)C1=CC=C(Cl)C=C1 UAALBJPKYVOYRB-UHFFFAOYSA-N 0.000 claims 1
- YMBOWJASIPJHPL-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-methyl-2-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(C)(CNC)C1=CC=C(Cl)C=C1 YMBOWJASIPJHPL-UHFFFAOYSA-N 0.000 claims 1
- RQEUDJXTUCAVAA-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNC)C1=CC=C(F)C=C1 RQEUDJXTUCAVAA-UHFFFAOYSA-N 0.000 claims 1
- HNVSGFVICJTHBH-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-methyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNC)C1=CC=C(OC)C=C1 HNVSGFVICJTHBH-UHFFFAOYSA-N 0.000 claims 1
- VTNKIRBLRDIXRQ-UHFFFAOYSA-N 2-(methylamino)-1-(4-nitrophenyl)-1-[4-(1h-pyrazol-4-yl)phenyl]ethanol Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(O)(CNC)C(C=C1)=CC=C1C=1C=NNC=1 VTNKIRBLRDIXRQ-UHFFFAOYSA-N 0.000 claims 1
- XNIAUSRAGOBQDX-UHFFFAOYSA-N 2-[(4-chlorophenyl)-[4-(1h-pyrazol-4-yl)phenyl]methoxy]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(OCCN)C1=CC=C(Cl)C=C1 XNIAUSRAGOBQDX-UHFFFAOYSA-N 0.000 claims 1
- NQEBEJVATHZQHM-UHFFFAOYSA-N 2-[3-(3,5-dimethyl-1h-pyrazol-4-yl)phenyl]-1-phenylethanamine Chemical compound CC1=NNC(C)=C1C1=CC=CC(CC(N)C=2C=CC=CC=2)=C1 NQEBEJVATHZQHM-UHFFFAOYSA-N 0.000 claims 1
- QBUGJWXOVSASPH-UHFFFAOYSA-N 2-[4-(3,5-dimethyl-1h-pyrazol-4-yl)phenyl]-2-phenylethanamine Chemical compound CC1=NNC(C)=C1C1=CC=C(C(CN)C=2C=CC=CC=2)C=C1 QBUGJWXOVSASPH-UHFFFAOYSA-N 0.000 claims 1
- PEVARZMNCRMKAQ-UHFFFAOYSA-N 2-[4-[2-(methylamino)-1-[4-(1h-pyrazol-4-yl)phenyl]ethyl]phenoxy]pyridine-4-carboxamide Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNC)C(C=C1)=CC=C1OC1=CC(C(N)=O)=CC=N1 PEVARZMNCRMKAQ-UHFFFAOYSA-N 0.000 claims 1
- QEHHLNLZIYNHFD-UHFFFAOYSA-N 2-[4-[4-[4-(1h-pyrazol-4-yl)phenyl]piperidin-4-yl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)CCNCC1 QEHHLNLZIYNHFD-UHFFFAOYSA-N 0.000 claims 1
- MWSMBSLUKDQMPK-UHFFFAOYSA-N 2-phenyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CN)C1=CC=CC=C1 MWSMBSLUKDQMPK-UHFFFAOYSA-N 0.000 claims 1
- GCIJUVFCSAIPKY-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(CCN)C(C=C1)=CC=C1C=1C=NNC=1 GCIJUVFCSAIPKY-UHFFFAOYSA-N 0.000 claims 1
- WBUYUGCRHOCOID-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-3-[4-(1h-pyrazol-4-yl)phenyl]propanamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(CC(=O)N)C(C=C1)=CC=C1C=1C=NNC=1 WBUYUGCRHOCOID-UHFFFAOYSA-N 0.000 claims 1
- CSPQEGYWLIIPIZ-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-3-[6-(1h-pyrazol-4-yl)pyridin-3-yl]propan-1-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(CCN)C(C=N1)=CC=C1C=1C=NNC=1 CSPQEGYWLIIPIZ-UHFFFAOYSA-N 0.000 claims 1
- MSRWMOWZENJWHN-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-n-methyl-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C(F)C(F)=CC=1C(CCNC)C(C=C1)=CC=C1C=1C=NNC=1 MSRWMOWZENJWHN-UHFFFAOYSA-N 0.000 claims 1
- FGCYAZQVNZXMNP-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C1=C(Cl)C(OC)=CC=C1C(CCN)C1=CC=C(C2=CNN=C2)C=C1 FGCYAZQVNZXMNP-UHFFFAOYSA-N 0.000 claims 1
- PRHHLNJGKNRDQE-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-n-methyl-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C(OC)C(Cl)=CC=1C(CCNC)C(C=C1)=CC=C1C=1C=NNC=1 PRHHLNJGKNRDQE-UHFFFAOYSA-N 0.000 claims 1
- XTCPRZFKMFVDJF-UHFFFAOYSA-N 3-(3-chlorophenoxy)-n-methyl-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CCNC)OC1=CC=CC(Cl)=C1 XTCPRZFKMFVDJF-UHFFFAOYSA-N 0.000 claims 1
- HEDXUHRIYXUKSI-UHFFFAOYSA-N 3-(3-chlorophenyl)-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=CC(Cl)=CC=1C(CCN)C(C=C1)=CC=C1C=1C=NNC=1 HEDXUHRIYXUKSI-UHFFFAOYSA-N 0.000 claims 1
- BLVZFJHSAUCMFX-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-methyl-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=CC(Cl)=CC=1C(CCNC)C(C=C1)=CC=C1C=1C=NNC=1 BLVZFJHSAUCMFX-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- A61K31/4164—1,3-Diazoles
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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PCT/GB2004/005464 WO2005061463A1 (en) | 2003-12-23 | 2004-12-23 | Pyrazole derivatives as protein kinase modulators |
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- 2004-12-23 WO PCT/GB2004/005464 patent/WO2005061463A1/en active Application Filing
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JP2007516272A (ja) | 2007-06-21 |
NZ547696A (en) | 2009-12-24 |
CA2548374A1 (en) | 2005-07-07 |
US20130005702A1 (en) | 2013-01-03 |
AU2004303602A1 (en) | 2005-07-07 |
US20110144080A1 (en) | 2011-06-16 |
US20140271662A1 (en) | 2014-09-18 |
CY1111493T1 (el) | 2015-08-05 |
US9283226B2 (en) | 2016-03-15 |
AU2004303602B2 (en) | 2008-12-18 |
AU2004303602C1 (en) | 2009-05-28 |
US20160250187A1 (en) | 2016-09-01 |
IL176400A0 (en) | 2006-10-05 |
MXPA06007326A (es) | 2007-01-26 |
KR20060130621A (ko) | 2006-12-19 |
EP1706385B1 (en) | 2010-10-06 |
HK1097543A1 (en) | 2007-06-29 |
IL176400A (en) | 2011-10-31 |
CA2548374C (en) | 2014-05-27 |
EP1706385A1 (en) | 2006-10-04 |
US8691806B2 (en) | 2014-04-08 |
NO20062633L (no) | 2006-07-20 |
US8247576B2 (en) | 2012-08-21 |
PL1706385T3 (pl) | 2011-03-31 |
JP4928949B2 (ja) | 2012-05-09 |
BRPI0418078A (pt) | 2007-04-17 |
WO2005061463A1 (en) | 2005-07-07 |
EP2228369A1 (en) | 2010-09-15 |
KR101164258B1 (ko) | 2012-07-11 |
BRPI0418078A8 (pt) | 2018-01-02 |
UY28946A1 (es) | 2006-01-31 |
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