JP2007516272A5 - - Google Patents
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- JP2007516272A5 JP2007516272A5 JP2006546339A JP2006546339A JP2007516272A5 JP 2007516272 A5 JP2007516272 A5 JP 2007516272A5 JP 2006546339 A JP2006546339 A JP 2006546339A JP 2006546339 A JP2006546339 A JP 2006546339A JP 2007516272 A5 JP2007516272 A5 JP 2007516272A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyrazol
- group
- chloro
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 24
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 21
- -1 hydroxy, amino, methylamino, dimethylamino Chemical group 0.000 claims 21
- 125000005647 linker group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000004429 atom Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 13
- 229910052731 fluorine Inorganic materials 0.000 claims 13
- 239000011737 fluorine Substances 0.000 claims 13
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 150000001721 carbon Chemical group 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- 239000000460 chlorine Substances 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004423 acyloxy group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 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
- 150000001204 N-oxides Chemical class 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 238000011282 treatment Methods 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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 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
- 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 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 230000006907 apoptotic process Effects 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 2
- 230000004663 cell proliferation Effects 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 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
- 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
- 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
- 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 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
- 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
- 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
- PMSURQYNKZJHOA-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CCN)C1=CC=C(Cl)C=C1 PMSURQYNKZJHOA-UHFFFAOYSA-N 0.000 claims 1
- NZKIKXUXRVDQAK-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-[4-(1h-pyrazol-4-yl)phenyl]propanamide Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CC(=O)N)C1=CC=C(Cl)C=C1 NZKIKXUXRVDQAK-UHFFFAOYSA-N 0.000 claims 1
- MLWHKTLBRHPGGV-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-methyl-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CCNC)C1=CC=C(Cl)C=C1 MLWHKTLBRHPGGV-UHFFFAOYSA-N 0.000 claims 1
- PMQWUCJKVOBNEE-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-methyl-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CCNC)C1=CC=C(F)C=C1 PMQWUCJKVOBNEE-UHFFFAOYSA-N 0.000 claims 1
- DXCGBCQOMLIHOA-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C1=CC(OC)=CC=C1C(CCN)C1=CC=C(C2=CNN=C2)C=C1 DXCGBCQOMLIHOA-UHFFFAOYSA-N 0.000 claims 1
- SAJGJQMGFRPHDO-UHFFFAOYSA-N 3-(4-phenoxyphenyl)-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CCN)C(C=C1)=CC=C1OC1=CC=CC=C1 SAJGJQMGFRPHDO-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- VRICFPVOFWNRLE-UHFFFAOYSA-N 3-phenyl-2-[3-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=CC(C2=CNN=C2)=CC=1C(CN)CC1=CC=CC=C1 VRICFPVOFWNRLE-UHFFFAOYSA-N 0.000 claims 1
- ZJEQGMQJPQNZJK-UHFFFAOYSA-N 3-phenyl-2-[3-(1h-pyrazol-4-yl)phenyl]propanenitrile Chemical compound C=1C=CC(C2=CNN=C2)=CC=1C(C#N)CC1=CC=CC=C1 ZJEQGMQJPQNZJK-UHFFFAOYSA-N 0.000 claims 1
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- USUVTKQVEFVSHN-UHFFFAOYSA-N 4-(2-chloro-3-fluorophenyl)-4-[4-(1h-pyrazol-4-yl)phenyl]piperidine Chemical compound FC1=CC=CC(C2(CCNCC2)C=2C=CC(=CC=2)C2=CNN=C2)=C1Cl USUVTKQVEFVSHN-UHFFFAOYSA-N 0.000 claims 1
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| EP2740731B1 (en) | 2007-06-13 | 2016-03-23 | Incyte Holdings Corporation | Crystalline salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile |
| EP2190811B1 (en) * | 2007-08-20 | 2013-08-07 | Merck Canada Inc. | Renin inhibitors |
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- 2004-12-23 MX MXPA06007326A patent/MXPA06007326A/es active IP Right Grant
- 2004-12-23 JP JP2006546339A patent/JP4928949B2/ja not_active Expired - Fee Related
- 2004-12-23 KR KR1020067014742A patent/KR101164258B1/ko not_active Expired - Fee Related
- 2004-12-23 NZ NZ547696A patent/NZ547696A/en not_active IP Right Cessation
- 2004-12-23 EP EP04806258A patent/EP1706385B1/en not_active Expired - Lifetime
- 2004-12-23 CA CA2548374A patent/CA2548374C/en not_active Expired - Fee Related
- 2004-12-23 AU AU2004303602A patent/AU2004303602C1/en not_active Ceased
- 2004-12-23 PL PL04806258T patent/PL1706385T3/pl unknown
- 2004-12-23 WO PCT/GB2004/005464 patent/WO2005061463A1/en not_active Ceased
- 2004-12-23 BR BRPI0418078A patent/BRPI0418078A8/pt active Search and Examination
- 2004-12-23 HR HR20100675T patent/HRP20100675T1/hr unknown
- 2004-12-23 US US10/596,788 patent/US8247576B2/en not_active Expired - Fee Related
-
2005
- 2005-06-08 UY UY28946A patent/UY28946A1/es not_active Application Discontinuation
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2006
- 2006-06-08 NO NO20062633A patent/NO20062633L/no not_active Application Discontinuation
- 2006-06-19 IL IL176400A patent/IL176400A/en not_active IP Right Cessation
-
2011
- 2011-01-03 CY CY20111100002T patent/CY1111493T1/el unknown
-
2012
- 2012-06-28 US US13/536,174 patent/US8691806B2/en not_active Expired - Fee Related
-
2014
- 2014-02-14 US US14/180,440 patent/US9283226B2/en not_active Expired - Fee Related
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2016
- 2016-01-29 US US15/010,831 patent/US20160250187A1/en not_active Abandoned
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