JP2008546751A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008546751A5 JP2008546751A5 JP2008517587A JP2008517587A JP2008546751A5 JP 2008546751 A5 JP2008546751 A5 JP 2008546751A5 JP 2008517587 A JP2008517587 A JP 2008517587A JP 2008517587 A JP2008517587 A JP 2008517587A JP 2008546751 A5 JP2008546751 A5 JP 2008546751A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyrazol
- chloro
- methyl
- group
- 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.)
- Pending
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims 14
- 201000010099 disease Diseases 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 13
- 239000011435 rock Substances 0.000 claims 13
- 108091000080 Phosphotransferase Proteins 0.000 claims 12
- 125000005647 linker group Chemical group 0.000 claims 12
- 102000020233 phosphotransferase Human genes 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 206010028980 Neoplasm Diseases 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 230000005764 inhibitory process Effects 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- -1 hydroxy, amino, methylamino, dimethylamino Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 230000002265 prevention Effects 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 208000024891 symptom Diseases 0.000 claims 6
- 206010027476 Metastases Diseases 0.000 claims 5
- 102000001253 Protein Kinase Human genes 0.000 claims 5
- 230000009401 metastasis Effects 0.000 claims 5
- 108060006633 protein kinase Proteins 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 230000009545 invasion Effects 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 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
- 125000002252 acyl group Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 230000035772 mutation Effects 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 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
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 206010064912 Malignant transformation Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 238000003745 diagnosis Methods 0.000 claims 2
- 230000006806 disease prevention Effects 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 102000034356 gene-regulatory proteins Human genes 0.000 claims 2
- 108091006104 gene-regulatory proteins Proteins 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000036212 malign transformation Effects 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000009467 reduction Effects 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 2
- 238000012216 screening Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 230000002792 vascular Effects 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
- 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
- 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
- GNOJHSRNZXLFFX-UHFFFAOYSA-N 3-phenyl-2-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CN)CC1=CC=CC=C1 GNOJHSRNZXLFFX-UHFFFAOYSA-N 0.000 claims 1
- 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
- MHPPVGSDNKCZMG-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-[4-(1h-pyrazol-4-yl)phenyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)CCNCC1 MHPPVGSDNKCZMG-UHFFFAOYSA-N 0.000 claims 1
- YLEMKLICYJNLDA-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenyl)-4-[4-(1h-pyrazol-4-yl)phenyl]piperidine Chemical compound C1=C(Cl)C(F)=CC(C2(CCNCC2)C=2C=CC(=CC=2)C2=CNN=C2)=C1 YLEMKLICYJNLDA-UHFFFAOYSA-N 0.000 claims 1
- JBBMHGJGPVSWOO-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-methyl-4-[4-(1h-pyrazol-4-yl)phenyl]piperidine Chemical compound C1CN(C)CCC1(C=1C=CC(=CC=1)C1=CNN=C1)C1=CC=C(Cl)C=C1 JBBMHGJGPVSWOO-UHFFFAOYSA-N 0.000 claims 1
- GVBDZLGRVUJEFW-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-[4-(5-methyl-1h-pyrazol-4-yl)phenyl]piperidine Chemical compound CC1=NNC=C1C1=CC=C(C2(CCNCC2)C=2C=CC(Cl)=CC=2)C=C1 GVBDZLGRVUJEFW-UHFFFAOYSA-N 0.000 claims 1
- PYVKMDJDKCKVJO-UHFFFAOYSA-N 4-(4-methoxyphenyl)-4-[4-(1h-pyrazol-4-yl)phenyl]piperidine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)CCNCC1 PYVKMDJDKCKVJO-UHFFFAOYSA-N 0.000 claims 1
- HGHCXFKOUIZYGF-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethyl]morpholine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)CN1CCOCC1 HGHCXFKOUIZYGF-UHFFFAOYSA-N 0.000 claims 1
- PAJNBJLDVKJXNX-UHFFFAOYSA-N 4-[3-(methylamino)-1-[4-(1h-pyrazol-4-yl)phenyl]propyl]phenol Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CCNC)C1=CC=C(O)C=C1 PAJNBJLDVKJXNX-UHFFFAOYSA-N 0.000 claims 1
- WZTPTWWAPVMONU-UHFFFAOYSA-N 4-[4-(2-methoxyethoxy)phenyl]-4-[4-(1h-pyrazol-4-yl)phenyl]piperidine Chemical compound C1=CC(OCCOC)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)CCNCC1 WZTPTWWAPVMONU-UHFFFAOYSA-N 0.000 claims 1
- IQTMZQRPCUSIKL-UHFFFAOYSA-N 4-[4-(3,5-dimethyl-1h-pyrazol-4-yl)phenyl]-4-phenylpiperidine Chemical compound CC1=NNC(C)=C1C1=CC=C(C2(CCNCC2)C=2C=CC=CC=2)C=C1 IQTMZQRPCUSIKL-UHFFFAOYSA-N 0.000 claims 1
- JDQHJOPZQIJCEA-UHFFFAOYSA-N 4-[4-(3-methoxypropoxy)phenyl]-4-[4-(1h-pyrazol-4-yl)phenyl]piperidine Chemical compound C1=CC(OCCCOC)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)CCNCC1 JDQHJOPZQIJCEA-UHFFFAOYSA-N 0.000 claims 1
- HLBRXOVHXRAVBQ-UHFFFAOYSA-N 4-[4-[1-(4-chlorophenyl)-2-pyrrolidin-1-ylethyl]phenyl]-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)CN1CCCC1 HLBRXOVHXRAVBQ-UHFFFAOYSA-N 0.000 claims 1
- JJMWTFLOALEUFK-UHFFFAOYSA-N 4-[4-[1-(4-chlorophenyl)-3-pyrrolidin-1-ylpropyl]phenyl]-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)CCN1CCCC1 JJMWTFLOALEUFK-UHFFFAOYSA-N 0.000 claims 1
- LMQVASLLHRUDEK-UHFFFAOYSA-N 4-[4-[2-(azetidin-1-yl)-1-(4-chlorophenoxy)ethyl]phenyl]-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1OC(C=1C=CC(=CC=1)C1=CNN=C1)CN1CCC1 LMQVASLLHRUDEK-UHFFFAOYSA-N 0.000 claims 1
- GXIKHGUANWIUPY-UHFFFAOYSA-N 4-[4-[2-(azetidin-1-yl)-1-(4-chlorophenyl)ethyl]phenyl]-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)CN1CCC1 GXIKHGUANWIUPY-UHFFFAOYSA-N 0.000 claims 1
- PEEKZDAJUZOSLT-UHFFFAOYSA-N 4-[4-[3-(azetidin-1-yl)-1-(4-chlorophenyl)propyl]phenyl]-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(=CC=1)C1=CNN=C1)CCN1CCC1 PEEKZDAJUZOSLT-UHFFFAOYSA-N 0.000 claims 1
- VBIDRMWBZZTFRK-UHFFFAOYSA-N 4-[4-[4-(1h-pyrazol-4-yl)phenyl]piperidin-4-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)CCNCC1 VBIDRMWBZZTFRK-UHFFFAOYSA-N 0.000 claims 1
- PBNKBTUXTSOMLR-UHFFFAOYSA-N 4-[4-[4-(1h-pyrazol-4-yl)phenyl]piperidin-4-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)CCNCC1 PBNKBTUXTSOMLR-UHFFFAOYSA-N 0.000 claims 1
- AOJCEFPPEOPJAD-UHFFFAOYSA-N 4-[4-[4-(1h-pyrazol-4-yl)phenyl]piperidin-4-yl]phenol Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)CCNCC1 AOJCEFPPEOPJAD-UHFFFAOYSA-N 0.000 claims 1
- DEUZQAZONXREGN-UHFFFAOYSA-N 4-[4-[4-(1h-pyrazol-4-yl)phenyl]piperidin-4-yl]pyridine Chemical group C1CNCCC1(C=1C=CC(=CC=1)C1=CNN=C1)C1=CC=NC=C1 DEUZQAZONXREGN-UHFFFAOYSA-N 0.000 claims 1
- HQMWZYTXIFWKPY-UHFFFAOYSA-N 4-[4-[4-(4-chlorophenyl)piperidin-4-yl]phenyl]-1h-pyrazole-5-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1(C=2C=CC(=CC=2)C=2C(=NNC=2)C#N)CCNCC1 HQMWZYTXIFWKPY-UHFFFAOYSA-N 0.000 claims 1
- LKFDJWGYWDCRPC-UHFFFAOYSA-N 4-phenyl-4-[4-(1h-pyrazol-4-yl)phenyl]piperidine Chemical compound C1CNCCC1(C=1C=CC(=CC=1)C1=CNN=C1)C1=CC=CC=C1 LKFDJWGYWDCRPC-UHFFFAOYSA-N 0.000 claims 1
- LZMOSYUFVYJEPY-UHFFFAOYSA-N AT7867 Chemical compound C1=CC(Cl)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)CCNCC1 LZMOSYUFVYJEPY-UHFFFAOYSA-N 0.000 claims 1
- 102000036365 BRCA1 Human genes 0.000 claims 1
- 108700020463 BRCA1 Proteins 0.000 claims 1
- 101150072950 BRCA1 gene Proteins 0.000 claims 1
- 102000052609 BRCA2 Human genes 0.000 claims 1
- 108700020462 BRCA2 Proteins 0.000 claims 1
- 101150008921 Brca2 gene Proteins 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 108010092160 Dactinomycin Proteins 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 102000009465 Growth Factor Receptors Human genes 0.000 claims 1
- 108010009202 Growth Factor Receptors Proteins 0.000 claims 1
- 206010021118 Hypotonia Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 206010023421 Kidney fibrosis Diseases 0.000 claims 1
- 206010061309 Neoplasm progression Diseases 0.000 claims 1
- 206010034764 Peutz-Jeghers syndrome Diseases 0.000 claims 1
- 102100026715 Serine/threonine-protein kinase STK11 Human genes 0.000 claims 1
- 101710181599 Serine/threonine-protein kinase STK11 Proteins 0.000 claims 1
- 206010064390 Tumour invasion Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 229910052891 actinolite Inorganic materials 0.000 claims 1
- 229930183665 actinomycin Natural products 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 230000033228 biological regulation Effects 0.000 claims 1
- 230000017531 blood circulation Effects 0.000 claims 1
- 230000009400 cancer invasion Effects 0.000 claims 1
- 230000021164 cell adhesion Effects 0.000 claims 1
- 230000010261 cell growth Effects 0.000 claims 1
- 230000012292 cell migration Effects 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 210000000349 chromosome Anatomy 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 230000008602 contraction Effects 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 230000003436 cytoskeletal effect Effects 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- DFDZKFAFULTKDV-UHFFFAOYSA-N methyl 2-[4-[4-[4-(1h-pyrazol-4-yl)phenyl]piperidin-4-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1C1(C=2C=CC(=CC=2)C2=CNN=C2)CCNCC1 DFDZKFAFULTKDV-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 230000036640 muscle relaxation Effects 0.000 claims 1
- 230000005996 muscular dysfunction Effects 0.000 claims 1
- 230000001878 mycolytic effect Effects 0.000 claims 1
- RUGFXXKVNXNFGY-UHFFFAOYSA-N n,n-dimethyl-2,2-bis[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CN(C)C)C(C=C1)=CC=C1C=1C=NNC=1 RUGFXXKVNXNFGY-UHFFFAOYSA-N 0.000 claims 1
- PJCLMNOZUMMYTJ-UHFFFAOYSA-N n,n-dimethyl-2-phenyl-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CN(C)C)C1=CC=CC=C1 PJCLMNOZUMMYTJ-UHFFFAOYSA-N 0.000 claims 1
- KMBPALGRPXPTJC-UHFFFAOYSA-N n,n-dimethyl-3-[4-(1h-pyrazol-4-yl)phenyl]-3-pyridin-2-ylpropan-1-amine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C(C=C1)=CC=C1C=1C=NNC=1 KMBPALGRPXPTJC-UHFFFAOYSA-N 0.000 claims 1
- YCAFDYGANIWYNW-UHFFFAOYSA-N n,n-dimethyl-4-[3-(methylamino)-1-[4-(1h-pyrazol-4-yl)phenyl]propyl]aniline Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CCNC)C1=CC=C(N(C)C)C=C1 YCAFDYGANIWYNW-UHFFFAOYSA-N 0.000 claims 1
- RLUISSQWDGXBRY-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethyl]propan-2-amine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNC(C)C)C1=CC=C(Cl)C=C1 RLUISSQWDGXBRY-UHFFFAOYSA-N 0.000 claims 1
- JTSLALYXYSRPGW-UHFFFAOYSA-N n-[5-(4-cyanophenyl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C1=C2)=CNC1=NC=C2C1=CC=C(C#N)C=C1 JTSLALYXYSRPGW-UHFFFAOYSA-N 0.000 claims 1
- IGGFWLLVYRWCCO-UHFFFAOYSA-N n-methyl-2,2-bis[4-(1h-pyrazol-4-yl)phenyl]acetamide Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(C(=O)NC)C(C=C1)=CC=C1C=1C=NNC=1 IGGFWLLVYRWCCO-UHFFFAOYSA-N 0.000 claims 1
- BOLSKJHQKNEEIZ-UHFFFAOYSA-N n-methyl-2,2-bis[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNC)C(C=C1)=CC=C1C=1C=NNC=1 BOLSKJHQKNEEIZ-UHFFFAOYSA-N 0.000 claims 1
- AVMYSWGHPQZPKK-UHFFFAOYSA-N n-methyl-2-(4-pyrazin-2-yloxyphenyl)-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNC)C(C=C1)=CC=C1OC1=CN=CC=N1 AVMYSWGHPQZPKK-UHFFFAOYSA-N 0.000 claims 1
- DKDQKBGMSVFFGE-UHFFFAOYSA-N n-methyl-2-[4-(1h-pyrazol-4-yl)phenyl]-2-(4-pyridin-3-ylphenyl)ethanamine Chemical compound C=1C=C(C=2C=NC=CC=2)C=CC=1C(CNC)C(C=C1)=CC=C1C=1C=NNC=1 DKDQKBGMSVFFGE-UHFFFAOYSA-N 0.000 claims 1
- WRTRCQJKGMMJCS-UHFFFAOYSA-N n-methyl-2-phenoxy-2-[4-(1h-pyrazol-4-yl)phenyl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)C=CC=1C(CNC)OC1=CC=CC=C1 WRTRCQJKGMMJCS-UHFFFAOYSA-N 0.000 claims 1
- PGDUARZFLYYKNP-UHFFFAOYSA-N n-methyl-2-phenyl-2-[6-(1h-pyrazol-4-yl)pyridin-3-yl]ethanamine Chemical compound C=1C=C(C2=CNN=C2)N=CC=1C(CNC)C1=CC=CC=C1 PGDUARZFLYYKNP-UHFFFAOYSA-N 0.000 claims 1
- GSCXAIQOLGKSEW-UHFFFAOYSA-N n-methyl-3-naphthalen-2-yl-3-[4-(1h-pyrazol-4-yl)phenyl]propan-1-amine Chemical compound C=1C=C2C=CC=CC2=CC=1C(CCNC)C(C=C1)=CC=C1C=1C=NNC=1 GSCXAIQOLGKSEW-UHFFFAOYSA-N 0.000 claims 1
- 230000001537 neural effect Effects 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- 230000002018 overexpression Effects 0.000 claims 1
- 244000052769 pathogen Species 0.000 claims 1
- 230000001717 pathogenic effect Effects 0.000 claims 1
- 210000001147 pulmonary artery Anatomy 0.000 claims 1
- 230000008707 rearrangement Effects 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 230000011664 signaling Effects 0.000 claims 1
- 210000002460 smooth muscle Anatomy 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 208000037816 tissue injury Diseases 0.000 claims 1
- 230000017423 tissue regeneration Effects 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 claims 1
- 230000005751 tumor progression Effects 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69300205P | 2005-06-22 | 2005-06-22 | |
| US69296105P | 2005-06-22 | 2005-06-22 | |
| PCT/GB2006/002276 WO2006136821A1 (en) | 2005-06-22 | 2006-06-21 | Pharmaceutical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008546751A JP2008546751A (ja) | 2008-12-25 |
| JP2008546751A5 true JP2008546751A5 (enExample) | 2009-08-06 |
Family
ID=37027831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008517587A Pending JP2008546751A (ja) | 2005-06-22 | 2006-06-21 | 医薬組成物 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8343953B2 (enExample) |
| EP (1) | EP1902032A1 (enExample) |
| JP (1) | JP2008546751A (enExample) |
| WO (1) | WO2006136821A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2228369A1 (en) | 2003-12-23 | 2010-09-15 | Astex Therapeutics Ltd. | Pyrazole derivatives as protein kinase modulators |
| WO2009025957A1 (en) * | 2007-08-22 | 2009-02-26 | Takeda Pharmaceuticals Company Limited | Erythropoietin receptor peptide formulations and uses |
| US8343953B2 (en) | 2005-06-22 | 2013-01-01 | Astex Therapeutics Limited | Pharmaceutical compounds |
| WO2006136837A2 (en) | 2005-06-23 | 2006-12-28 | Astex Therapeutics Limited | Pharmaceutical combinations comprising pyrazole derivatives as protein kinase modulators |
| GB0704932D0 (en) * | 2007-03-14 | 2007-04-25 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| WO2009005460A1 (en) * | 2007-06-29 | 2009-01-08 | Astrazeneca Ab | Small molecule inhibitors of navl.7 sodium channels for the treatment of pain disorders |
| ES2548578T3 (es) * | 2007-12-27 | 2015-10-19 | Kissei Pharmaceutical Co., Ltd. | Monosebacato de un derivado de pirazol |
| US20170157038A1 (en) * | 2008-11-13 | 2017-06-08 | Gholam A. Peyman | Ophthalmic drug delivery method |
| KR101699991B1 (ko) | 2009-02-11 | 2017-01-26 | 메르크 파텐트 게엠베하 | 신규의 아미노 아자헤테로시클릭 카르복사미드 |
| ES2654332T3 (es) | 2009-08-07 | 2018-02-13 | Merck Patent Gmbh | Nuevos compuestos azaheterocíclicos |
| US9586938B2 (en) | 2010-07-29 | 2017-03-07 | Merck Patent Gmbh | Cyclic amine azaheterocyclic carboxamides |
| UA110113C2 (xx) | 2010-07-29 | 2015-11-25 | Біциклічні азагетероциклічні карбоксаміди | |
| EA023821B1 (ru) | 2010-11-24 | 2016-07-29 | Мерк Патент Гмбх | Хиназолинкарбоксамидазетидины, их применение в лечении гиперпролиферативных заболеваний и содержащие их композиции |
| HRP20171554T1 (hr) | 2011-09-12 | 2017-11-17 | Merck Patent Gmbh | Novi imidazol amini kao modulatori aktivnosti kinaze |
| ES2646759T3 (es) | 2011-09-12 | 2017-12-15 | Merck Patent Gmbh | Derivados de aminopirimidina para uso como moduladores de la actividad de la quinasa |
| JP6105594B2 (ja) | 2011-09-30 | 2017-03-29 | エンドゥ ファーマシューティカルズ，インコーポレイティド | 癌処置用ｃｙｐ１７阻害剤としてのイミダゾール誘導体 |
| JP6130383B2 (ja) | 2011-09-30 | 2017-05-17 | エンドゥ ファーマシューティカルズ，インコーポレイティド | ピリジン誘導体 |
| WO2013096194A1 (en) | 2011-12-22 | 2013-06-27 | Merck Patent Gmbh | Novel heterocyclic carboxamides as modulators of kinase activity |
| AR093511A1 (es) | 2012-11-16 | 2015-06-10 | Merck Patent Gmbh | Derivados de imidazol-piperidinilo como moduladores de la actividad de cinasas |
| AR093512A1 (es) | 2012-11-16 | 2015-06-10 | Merck Patent Gmbh | Derivados heterociclicos como moduladores de la actividad de cinasas |
| EA033655B1 (ru) | 2012-11-29 | 2019-11-13 | Merck Patent Gmbh | Производные азахиназолин карбоксамида |
| MX370448B (es) | 2013-03-11 | 2019-12-13 | Merck Patent Gmbh | Derivados de 6- [4- (1h-imidazol-2-il) piperidin-1-il] pirimidin-4-amina como moduladores de la actividad de cinasa. |
| NZ725361A (en) | 2014-04-03 | 2022-09-30 | Merck Patent Gmbh | Combinations of cancer therapeutics |
| JP7234201B2 (ja) * | 2017-07-12 | 2023-03-07 | ブリストル－マイヤーズ スクイブ カンパニー | 心不全の治療のためのｒｏｃｋの５員アミノヘテロ環および５，６－または６，６員二環式アミノヘテロ環の阻害剤 |
| IL302951A (en) | 2020-11-16 | 2023-07-01 | Merck Patent Gmbh | Kinase inhibitor combinations for cancer treatment |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990009381A1 (en) | 1989-02-08 | 1990-08-23 | Abbott Laboratories | 4-hydroxythiazoles as 5-lipoxygenase inhibitors |
| US5049570A (en) | 1990-01-23 | 1991-09-17 | Du Pont Merck Pharmaceutical Company | Pyridylphenyl nitrogen heterocycle-substituted carbinols and derivatives thereof with anti-inflammatory activity |
| FR2707295A1 (fr) | 1993-06-07 | 1995-01-13 | Rhone Poulenc Agrochimie | Fongicides pyrazoles substitués en position 3 par un hétérocycle. |
| US6756388B1 (en) | 1993-10-12 | 2004-06-29 | Pfizer Inc. | Benzothiophenes and related compounds as estrogen agonists |
| US5532356A (en) * | 1995-06-06 | 1996-07-02 | The Dupont Merck Pharmaceutical Company | Method for preparing N,N'-disubstituted cyclic ureas |
| GB9512961D0 (en) * | 1995-06-26 | 1995-08-30 | Pfizer Ltd | Antifungal agents |
| CA2249645A1 (en) | 1996-04-03 | 1997-10-09 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| GB2339298B (en) * | 1996-04-30 | 2000-05-10 | Eastman Kodak Co | Use of pyrazolone image dye-forming couplers for enhancing light stability |
| AR008789A1 (es) | 1996-07-31 | 2000-02-23 | Bayer Corp | Piridinas y bifenilos substituidos |
| AU5522498A (en) | 1996-12-13 | 1998-07-03 | Merck & Co., Inc. | Substituted aryl piperazines as modulators of chemokine receptor activity |
| US6020357A (en) * | 1996-12-23 | 2000-02-01 | Dupont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
| GB9700555D0 (en) * | 1997-01-13 | 1997-03-05 | Merck Sharp & Dohme | Therapeutic agents |
| US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| AU751139B2 (en) | 1997-10-13 | 2002-08-08 | Astellas Pharma Inc. | Amide derivative |
| CN1289248A (zh) | 1998-01-29 | 2001-03-28 | 维洛药品公司 | 治疗或预防肺病毒感染及有关疾病的化合物、组合物和方法 |
| GB9804734D0 (en) * | 1998-03-05 | 1998-04-29 | Pfizer Ltd | Compounds |
| DE69935335T2 (de) | 1998-08-07 | 2007-11-22 | Novartis Vaccines and Diagnostics, Inc., Emeryville | Pyrazole als modulatoren des östrogenrezeptors |
| HN1999000149A (es) | 1998-09-09 | 2000-01-12 | Pfizer Prod Inc | Derivados de 4,4-biarilpiperidina |
| US6503905B1 (en) | 1998-12-29 | 2003-01-07 | Pfizer Inc | 3,3-biarylpiperidine and 2,2-biarylmorpholine derivatives |
| WO2000066562A1 (en) | 1999-05-03 | 2000-11-09 | Dr. Reddy's Research Foundation | Pyrazoles having antiinflammatory activity |
| EP1185530A1 (en) | 1999-05-14 | 2002-03-13 | Neurocrine Biosciences, Inc. | Imidazo- and pyrrolo[1,2-a]pyrimid-4-ones as gonadotropin-releasing hormone receptor antagonists |
| CZ2002961A3 (cs) | 1999-09-17 | 2002-08-14 | Millennium Pharmaceuticals, Inc. | Benzamidy a příbuzné sloučeniny pro inhibici faktoru Xa |
| US6632815B2 (en) * | 1999-09-17 | 2003-10-14 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| AU781880B2 (en) | 1999-09-17 | 2005-06-16 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| US7393842B2 (en) * | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| US6455525B1 (en) | 1999-11-04 | 2002-09-24 | Cephalon, Inc. | Heterocyclic substituted pyrazolones |
| WO2001064642A2 (en) | 2000-02-29 | 2001-09-07 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| IL136458A0 (en) | 2000-05-30 | 2001-06-14 | Peptor Ltd | Protein kinase inhibitors |
| US6511994B2 (en) | 2000-10-11 | 2003-01-28 | Merck & Co., Inc. | Modulators of CCR5 chemokine receptor activity |
| JP2004538266A (ja) | 2001-04-27 | 2004-12-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | ピラゾール由来のキナーゼインヒビター |
| US6750239B2 (en) * | 2001-08-03 | 2004-06-15 | Vertex Pharmaceuticals Incorporated | Pyrazole-derived kinase inhibitors and uses thereof |
| FR2830192B1 (fr) | 2001-09-28 | 2004-08-20 | Oreal | Composition tinctoriale comprenant une base d'oxydation du type diaminopyrazole et un coupleur pyrazolo-azole |
| WO2003048081A2 (en) | 2001-12-04 | 2003-06-12 | Bristol-Myers Squibb Company | Glycinamides as factor xa inhibitors |
| US7998986B2 (en) | 2001-12-21 | 2011-08-16 | Exelixis Patent Company Llc | Modulators of LXR |
| AP1822A (en) | 2002-02-14 | 2008-01-30 | Pharmacia Corp | Substituted pyridinones as modulators of P38 MAP kinase. |
| MXPA04009040A (es) | 2002-03-20 | 2005-01-25 | Metabolex Inc | Acidos fenilaceticos sustituidos. |
| EP1492477B1 (en) | 2002-04-08 | 2016-04-13 | Boston Scientific Scimed, Inc. | Satiation devices and methods |
| AU2003223708A1 (en) | 2002-04-23 | 2003-11-10 | Axys Pharmaceuticals, Inc. | Novel phenyl derivatives as inducers of apoptosis |
| EP1542997B1 (en) | 2002-07-24 | 2012-02-29 | Dermira (Canada), Inc. | Pyrazolylbenzothiazole derivatives and their use as therapeutic agents |
| MXPA05002983A (es) * | 2002-09-18 | 2005-06-22 | Univ Missouri | Analogos de opiato selectivos del receptor opioide d. |
| DK1569696T3 (da) * | 2002-11-21 | 2010-11-15 | Bayhill Therapeutics Inc | Fremgangsmåder og immunmodulatoriske nukleinsyrepræparater til forebyggelse og behandling af sygdomme |
| US7135575B2 (en) * | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| CN102584813B (zh) | 2003-05-14 | 2016-07-06 | Ngc药物公司 | 化合物及其在调节淀粉样蛋白β中的用途 |
| EP1644365A2 (en) | 2003-07-02 | 2006-04-12 | Biofocus Discovery Ltd | Pyrazine and pyridine derivatives as rho kinase inhibitors |
| EP2256106B1 (en) | 2003-07-22 | 2015-05-06 | Astex Therapeutics Limited | 3,4-disubstituted 1H-pyrazole compounds and their use as cyclin dependent kinases (CDK) and glycogen synthase kinase-3 (GSK-3) modulators |
| TWI344961B (en) * | 2003-10-15 | 2011-07-11 | Ube Industries | Novel indazole derivative |
| WO2005048953A2 (en) | 2003-11-13 | 2005-06-02 | Ambit Biosciences Corporation | Amide derivatives as kinase modulators |
| EP1692112A4 (en) | 2003-12-08 | 2008-09-24 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS, AND METHODS |
| EP2228369A1 (en) * | 2003-12-23 | 2010-09-15 | Astex Therapeutics Ltd. | Pyrazole derivatives as protein kinase modulators |
| WO2005117909A2 (en) | 2004-04-23 | 2005-12-15 | Exelixis, Inc. | Kinase modulators and methods of use |
| UY29177A1 (es) | 2004-10-25 | 2006-05-31 | Astex Therapeutics Ltd | Derivados sustituidos de purina, purinona y deazapurina, composiciones que los contienen métodos para su preparación y sus usos |
| AU2005322085B2 (en) | 2004-12-28 | 2012-07-19 | Exelixis, Inc. | [1H-pyrazolo[3, 4-d]pyrimidin-4-yl]-piperidine or -piperazine compounds as serine-threonine kinase modulators (p70S6K, Atk1 and Atk2) for the treatment of immunological, inflammatory and proliferative diseases |
| US7423043B2 (en) | 2005-02-18 | 2008-09-09 | Lexicon Pharmaceuticals, Inc. | 4-Piperidin-1-yl-7H-pyrrolo[2,3-d]pyrimidine compounds |
| EP1919875A2 (en) | 2005-06-21 | 2008-05-14 | Astex Therapeutics Limited | Pyrazole derivatives and their use as pka and pkb modulators |
| UY29610A1 (es) | 2005-06-21 | 2007-01-31 | Cancer Rec Tech Ltd | Aril-alquilaminas y heteroaril-alquilaminas como inhibidores de la quinasa proteínica |
| GB2427406A (en) | 2005-06-21 | 2006-12-27 | Astex Technology Ltd | Silicon-containing PKB/PKA kinase inhibitors |
| WO2006136823A1 (en) | 2005-06-21 | 2006-12-28 | Astex Therapeutics Limited | Heterocyclic containing amines as kinase b inhibitors |
| US8343953B2 (en) | 2005-06-22 | 2013-01-01 | Astex Therapeutics Limited | Pharmaceutical compounds |
| WO2006136837A2 (en) | 2005-06-23 | 2006-12-28 | Astex Therapeutics Limited | Pharmaceutical combinations comprising pyrazole derivatives as protein kinase modulators |
| GB0704932D0 (en) | 2007-03-14 | 2007-04-25 | Astex Therapeutics Ltd | Pharmaceutical compounds |
-
2006
- 2006-06-21 US US11/993,831 patent/US8343953B2/en not_active Expired - Fee Related
- 2006-06-21 EP EP06755582A patent/EP1902032A1/en not_active Withdrawn
- 2006-06-21 JP JP2008517587A patent/JP2008546751A/ja active Pending
- 2006-06-21 WO PCT/GB2006/002276 patent/WO2006136821A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20100675T1 (hr) | Derivati pirazola kao modulatori protein kinaze | |
| JP2007516272A5 (enExample) | ||
| JP5966014B2 (ja) | 新規トリフルオロメチル−オキサジアゾール誘導体および疾患の処置におけるその使用 | |
| JP6170040B2 (ja) | ピルフェニドン及び選択された患者における抗線維化療法 | |
| US20130150385A1 (en) | Cancer therapy using a combination of a hsp90 inhibitory compounds and a egfr inhibitor | |
| US20140045908A1 (en) | Hsp90 inhibitory compounds in treating jak/stat signaling-mediated cancers | |
| DK2799427T3 (en) | Therapeutic compounds | |
| JP2007520520A5 (enExample) | ||
| JP2016534124A5 (enExample) | ||
| US20250235452A1 (en) | Methods of treating fibrosis | |
| JP2010505832A5 (enExample) | ||
| JP2007523182A5 (enExample) | ||
| JP2008546836A (ja) | 新規な用途 | |
| NZ515374A (en) | Remedies or prophylactics for diseases in association with chemokines | |
| JP2016506964A5 (ja) | ナトリウムチャネルの調節剤としてのキノリンおよびキノキサリンアミド | |
| JP2004523535A5 (enExample) | ||
| US12605377B2 (en) | Methods of treating fibrosis | |
| JP2007530690A5 (enExample) | ||
| JP2019525948A5 (enExample) | ||
| JP2019534310A5 (enExample) | ||
| JP2008546754A5 (enExample) | ||
| JP2004524279A5 (enExample) | ||
| WO2024182483A1 (en) | Methods of treating fibrosis | |
| JP2007521313A5 (enExample) | ||
| TW201026684A (en) | Phosphodiesterase type III (PDE III) inhibitors or Ca2+ -sensitizing agents for the treatment of hypertrophic cardiomyopathy |