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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Abstract
Spoj formule (I): (I) ili njegova sol, solvat, tautomer ili N-oksid; naznacen time sto je A zasicena ugljikovodicna vezna skupina koja sadrzi 1 do 7 atoma ugljika, ta vezna skupina ima najvecu duljinu lanca od 5 atoma koji se pruzaju izmedu R1 i NR2R3 i najvecu duljinu lanca od 4 atoma koji se pruzaju izmedu E i NR2R3, gdje jedan od atoma ugljika u veznoj skupini moze po izboru biti zamijenjen atomom kisika ili dusika; i gdje atomi ugljika vezne skupine A mogu po izboru imati jedan ili vise supstituenata izabranih izmedu okso, fluora i hidroksi, uz uvjet da se hidroksilna skupina, kada je prisutna, ne nalazi na α atomu ugljika u odnosu na NR2R3 skupinu i uz uvjet da se okso skupina, kada je prisutna, nalazi na α atomu ugljika u odnosu na NR2R3 skupinu; E je monociklicka ili biciklicka karbociklicka ili heterociklicka skupina pri cemu E nije supstituiran ili ima do 4 supstituenta R8 izabrana izmedu hidroksi, okso (kada E nije aromatski), klor, brom, trifluorometil, cijano, C1-4 hidrokarbiloksi i C1-4 hidrokarbil po izboru supstituiran s C1-2 alkoksi ili hidroksil; R1 je arilna ili heteroarilna skupina koja nije supstituirana ili ima jedan ili vise supstituenata izabranih izmedu hidroksi; C1-4 aciloksi; fluor; klor; brom; trifluorometil; cijano; CONH2; nitro; C1-4 hidrokarbiloksi i C1-4 hidrokarbil od kojih svaki moze po izboru biti supstituiran s C1-2 alkoksi, karboksi ili hidroksi; C1-4 acilamino; benzoilamino; pirolidinokarbonil; piperidinokarbonil; morfolinokarbonil; piperazinokarbonil; petero- i sesteroclane heteroarilne i heteroariloksi skupine sadrze jedan ili dva heteroatoma izabrana izmedu N, O i S; fenil; fenil C1-4 alkil; fenil-C1-4 alkoksi; heteroaril-C1-4 alkil; heteroaril-C1-4 alkoksi i fenoksi, gdje su skupine heteroaril, heteroariloksi, fenil, fenil C1-4 alkil, fenil-C1-4 alkoksi, heteroaril C1-4 alkil, heteroaril-C1-4 alkoksi i fenoksi svaka po izboru supstituirane s 1, 2 ili 3 supstituenta izabrana izmedu C1-2 aciloksi, fluor, klor, brom, trifluorometil, cijano, CONH2, C1-2 hidrokarbiloksi i C1-2 hidrokarbil od kojih je svaki po izboru supstituiran sa metoksi ili hidroksil; R2 i R3 su nezavisno jedan od drugog izabrani izmedu vodika, C1-4 hidrokarbil i C1-4 acil gdje hidrokarbilni i acilni dijelovi mogu po izboru biti supstituirani jednim ili s vise supstituenta izabrana izmedu fluor, hidroksi, amino, metilamino, dimetilamino i metoksi; ili R2 i R3 zajedno s atomom dusika, na koji su vezani, tvore ciklicku skupinu izabranu izmedu imidazolske skupine i zasicene monociklicke heterociklicke skupine s 4-7 clanova prstena i koja po izboru sadrzi drugi heteroatomni clan prstena izabran izmedu O i N; ili jedan od R2 i R3 zajedno s atomom dusika, na koji su vezani, i s jednim ili vise atoma iz vezne skupine A tvore zasicenu monociklicku heterociklicku skupinu s 4-7 clanova prstena i koja po izboru sadrzi drugi heteroatomni clan prstena izabran izmedu O i N; ili NR2R3 i atom ugljika vezne skupine A na koji je spojen, zajedno tvor
Claims (54)
1. Spoj formule (I):
[image]
(I)
ili njegova sol, solvat, tautomer ili N-oksid;
naznačen time što je A zasićena ugljikovodična vezna skupina koja sadrži 1 do 7 atoma ugljika, ta vezna skupina ima najveću duljinu lanca od 5 atoma koji se pružaju između R1 i NR2R3 i najveću duljinu lanca od 4 atoma koji se pružaju između E i NR2R3, gdje jedan od atoma ugljika u veznoj skupini može po izboru biti zamijenjen atomom kisika ili dušika; i gdje atomi ugljika vezne skupine A mogu po izboru imati jedan ili više supstituenata izabranih između okso, fluora i hidroksi, uz uvjet da se hidroksilna skupina, kada je prisutna, ne nalazi na α atomu ugljika u odnosu na NR2R3 skupinu i uz uvjet da se okso skupina, kada je prisutna, nalazi na α atomu ugljika u odnosu na NR2R3 skupinu;
E je monociklička ili biciklička karbociklička ili heterociklička skupina pri čemu E nije supstituiran ili ima do 4 supstituenta R8 izabrana između hidroksi, okso (kada E nije aromatski), klor, brom, trifluorometil, cijano, C1-4 hidrokarbiloksi i C1-4 hidrokarbil po izboru supstituiran s C1-2 alkoksi ili hidroksil;
R1 je arilna ili heteroarilna skupina koja nije supstituirana ili ima jedan ili više supstituenata izabranih između hidroksi; C1-4 aciloksi; fluor; klor; brom; trifluorometil; cijano; CONH2; nitro; C1-4 hidrokarbiloksi i C1-4 hidrokarbil od kojih svaki može po izboru biti supstituiran s C1-2 alkoksi, karboksi ili hidroksi; C1-4 acilamino; benzoilamino; pirolidinokarbonil; piperidinokarbonil; morfolinokarbonil; piperazinokarbonil; petero- i šesteročlane heteroarilne i heteroariloksi skupine sadrže jedan ili dva heteroatoma izabrana između N, O i S; fenil; fenilC1-4 alkil; fenil-C1-4 alkoksi; heteroaril-C1-4 alkil; heteroaril-C1-4 alkoksi i fenoksi, gdje su skupine heteroaril, heteroariloksi, fenil, fenilC1-4 alkil, fenil-C1-4 alkoksi, heteroarilC1-4 alkil, heteroaril-C1-4 alkoksi i fenoksi svaka po izboru supstituirane s 1, 2 ili 3 supstituenta izabrana između C1-2 aciloksi, fluor, klor, brom, trifluorometil, cijano, CONH2, C1-2 hidrokarbiloksi i C1-2 hidrokarbil od kojih je svaki po izboru supstituiran sa metoksi ili hidroksil;
R2 i R3 su nezavisno jedan od drugog izabrani između vodika, C1-4 hidrokarbil i C1-4 acil gdje hidrokarbilni i acilni dijelovi mogu po izboru biti supstituirani jednim ili s više supstituenta izabrana između fluor, hidroksi, amino, metilamino, dimetilamino i metoksi;
ili R2 i R3 zajedno s atomom dušika, na koji su vezani, tvore cikličku skupinu izabranu između imidazolske skupine i zasićene monocikličke heterocikličke skupine s 4-7 članova prstena i koja po izboru sadrži drugi heteroatomni član prstena izabran između O i N;
ili jedan od R2 i R3 zajedno s atomom dušika, na koji su vezani, i s jednim ili više atoma iz vezne skupine A tvore zasićenu monocikličku heterocikličku skupinu s 4-7 članova prstena i koja po izboru sadrži drugi heteroatomni član prstena izabran između O i N;
ili NR2R3 i atom ugljika vezne skupine A na koji je spojen, zajedno tvore cijano skupinu;
R4 je izabran između vodika, halogena, C1-5 zasićenog hidrokarbila, C1-5 zasićenog hidrokarbiloksi, cijano, i CF3; i
R5 je izabran između vodika, halogena, C1-5 zasićenog hidrokarbila, C1-5 zasićenog hidrokarbiloksi, cijano, CONH2, CONHR9, CF3, NH2, NHCOR9 ili NHCONHR9;
R9 je skupina R9a ili (CH2)R9a, pri čemu je R9a monociklička ili biciklička skupina koja može biti karbociklička ili heterociklička;
karbociklička skupina ili heterociklička skupina R9a je po izboru supstituirana jednim ili više supstituenata izabrana između halogena, hidroksi, trifluorometil, cijano, nitro, karboksi, amino, mono- ili di-C1-4 hidrokarbilamino; skupina Ra-Rb gdje je Ra veza, O, CO, X1C(X2), C(X2)X1, X1C(X2)X1, S, SO, SO2, NRc, SO2NRc ili NRcSO2; i Rb je izabran između vodika, heterocikličke skupine s 3 do 12 članova prstena, i C1-8 hidrokarbilne skupine po izboru supstituirane jednim ili više supstituenta izabrana između hidroksi, okso, halogen, cijano, nitro, karboksi, amino, mono- ili di-C14 hidrokarbilamino, karbocikličke i heterocikličke skupine imaju od 3 do 12 članova prstena i gdje jedan ili više atoma ugljika C1-8 hidrokarbilne skupine mogu po izboru biti zamijenjeni s O, S, SO, SO2, NRc, X1C(X2), C(X2)X1 ili X1C(X2)X1;
Rc je izabran između vodika i C1-4 hidrokarbila; i
X1 je O, S ili NRc i X2je =O, =S ili =NRc.
2. Spoj prema zahtjevu 1 formule (Ia):
[image]
(Ia)
ili njegova sol, solvat, tautomer ili N-oksid;
naznačen time što je A zasićena ugljikovodična vezna skupina koja sadrži 1 do 7 atoma ugljika, ta vezna skupina ima najveću duljinu lanca od 5 atoma koji se pružaju između R1 i NR2R3 i najveću duljinu lanca od 4 atoma koji se pružaju između E i NR2R3, gdje jedan od atoma ugljika u veznoj skupini može po izboru biti zamijenjen atomom kisika ili dušika; i gdje atomi ugljika vezne skupine A mogu po izboru imati jedan ili više supstituenata izabranih između okso, fluora i hidroksi, uz uvjet da se hidroksilna skupina, kada je prisutna, ne nalazi na α atomu ugljika u odnosu na NR2R3 skupinu i uz uvjet da se okso skupina, kada je prisutna, nalazi na α atomu ugljika u odnosu na NR2R3 skupinu;
E je monociklička ili biciklička karbociklička ili heterociklička skupina pri čemu E nije supstituiran ili ima do 4 supstituenta R8 kako je definirano u zahtjevu 1;
R1 je aril ili heteroarilna skupina koja nije supstituirana ili je supstituirana kako je definirano u zahtjevu 1
R2 i R3 su nezavisno jedan od drugog izabrani između vodika, C1-4 hidrokarbil i C1-4 acil;
ili R2 i R3 zajedno s atomom dušika, na koji su vezani, tvore zasićenu monocikličku heterocikličku skupinu s 4-7 članova prstena i koja po izboru sadrži drugi heteroatomni član prstena izabran između O i N;
ili jedan od R2 i R3 zajedno s atomom dušika, na koji su vezani, i s jednim ili više atoma iz vezne skupine A tvore zasićenu monocikličku heterocikličku skupinu s 4-7 članova prstena i koja po izboru sadrži drugi heteroatomni član prstena izabran između O i N;
ili NR2R3 i atom ugljika vezne skupine A na koji je spojen, zajedno tvore cijano skupinu;
R4 je izabran između vodika, halogena, C1-5 zasićenog hidrokarbila, cijano i CF3; i
R5 je izabran između vodika, halogena, C1-5 zasićenog hidrokarbila, cijano, CONH2, CONHR9,CF3, NH2, NHCOR9 ili NHCONHR9;
R9 je fenil ili benzil od kojih svaki po izboru može biti supstituiran jednim ili više supstituenta izabrana između halogena, hidroksi, trifluorometil, cijano, nitro, karboksi, amino, mono- ili di-C1-4 hidrokarbilamino; skupina Ra-Rb gdje je Ra veza, O, CO, X1C(X2), C(X2)X1, X1C(X2)X1, S, SO, SO2, NRc, SO2NRc ili NRcSO2; i Rb je izabran između vodika, heterocikličke skupine s 3 do 12 članova prstena, i C1-8 hidrokarbilne skupine po izboru supstituirane jednim ili više supstituenta izabrana između hidroksi, okso, halogen, cijano, nitro, karboksi, amino, mono- ili di-C14 hidrokarbilamino, karbocikličke i heterocikličke skupine imaju od 3 do 12 članova prstena i gdje jedan ili više atoma ugljika C1-8 hidrokarbilne skupine mogu po izboru biti zamijenjeni s O, S, SO, SO2, NRc, X1C(X2), C(X2)X1 ili X1C(X2)X1;
Rc je izabran između vodika i C1-4 hidrokarbila; i
X1 je O, S ili NRc i X2 je =O, =S ili =NRc.
Spoj prema zahtjevu 1 ili 2, naznačen time što je A zasićena ugljikovodična vezna skupina koja sadrži 1 do 7 atoma ugljika, ta vezna skupina ima najveću duljinu lanca od 5 atoma koji se pružaju između R1 i NR2R3 i najveću duljinu lanca od 4 atoma koji se pružaju između E i NR2R3, gdje jedan od atoma ugljika u veznoj skupini može po izboru biti zamijenjen atomom kisika ili dušika; i gdje atomi ugljika vezne skupine A mogu po izboru imati jedan ili više supstituenata izabranih između fluora i hidroksi, uz uvjet da se hidroksilna skupina, kada je prisutna, ne nalazi na α atomu ugljika u odnosu na NR2R3; i
R5 je izabran između vodika, halogena, C1-5 zasićenog hidrokarbila, cijano, CONH2, CF3, NH2, NHCOR9 i NHCONHR9.
3. Spoj prema bilo kojem od zahtjeva 1 do 3, naznačen time što vezna skupina A ima najveću duljinu lanca od 3 atoma koji se pružaju između R1 i NR2R3.
4. Spoj prema zahtjevu 4, naznačen time što vezna skupina A ima najveću duljinu lanca od 2 atoma koji se pružaju između R1 i NR2R3.
5. Spoj prema bilo kojem od zahtjeva 1 do 5, naznačen time što vezna skupina A ima najveću duljinu lanca od 3 atoma koji se pružaju između E i NR2R3.
6. Spoj prema zahtjevu 6, naznačen time što vezna skupina A ima duljinu lanca od 2 ili 3 atoma koji se pružaju između R1 i NR2R3 i duljinu lanca od 2 ili 3 atoma koji se pružaju između E i NR2R3.
7. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što je atom vezne skupine koji je povezan izravno na skupinu E atom ugljika i vezna skupina A ima u potpunosti ugljični kostur.
8. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time što je dio R1-A-NR2R3 spoja predstavljen formulom R1(G)k-(CH2)m-W-Ob-(CH2)n-(CR6R7)p-NR2R3 gdje G je NH, NMe ili O; W je spojen na skupinu E i izabran je između (CH2)j-CR20, (CH2)j-N i (NH)j-CH; b je 0 ili 1, j je 0 ili 1, k je 0 ili 1, m je 0 ili 1, n je 0, 1, 2, ili 3 i p su 0 ili 1; zbroj b i k je 0 ili 1; zbroj j, k, m, n i p ne prelazi 4; R6 i R7 su isti ili različiti i izabrani su između metil i etil, ili CR6R7 tvori ciklopropil; i R20 je izabran između vodika, metila, hidroksi i fluora.
9. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time što je dio R1-A-NR2R3 predstavljen formulom R1(G)k-(CH2)m-X-(CH2)n-(CR6R7)p-NR2R3 gdje G je NH, NMe ili O; X je spojen na skupinu E i izabran između (CH2)j-CH, (CH2)j-N i (NH)j-CH; j je 0 ili 1, k je 0 ili 1, m je 0 ili 1, n je 0, 1, 2, ili 3 i p je 0 ili 1, i zbroj j, k, m, n i p ne prelazi 4; i R6 i R7 su isti ili različiti i izabrani su između metil i etil, ili CR6R7 tvori ciklopropil.
10. Spoj prema zahtjevu 10, naznačen time što (i) k je 0, m je 0 ili 1, n je 0, 1, 2 ili 3 i p je 0; ili (ii) k je 0, m je 0 ili 1, n je 0, 1 ili 2 i p je 1.
11. Spoj prema zahtjevu 10, naznačen time što (i) X je (CH2)j-CH, k je 1, m je 0, n je 0, 1,2 ili 3 i p je 0; ili (ii) X je (CH2)j-CH, k je 1, m je 0, n je 0, 1 ili 2 i p je 1.
12. Spoj prema zahtjevu 10 ili 12, naznačen time što (i) j je 0; ili (ii) j je 1; ili (iii) CR6R7 je C(CH3)2.
13. Spoj prema zahtjevu 10, naznačen time što je dio R1-A-NR2R3 spoja predstavljen formulom R1X-(CH2)n-NR2R3 gdje je X spojen na skupinu E i to je skupina CH, i n je 2.
14. Spoj prema zahtjevu 1 ili 2, naznačen time što je R1-A(E)-NR2R3 izabran između skupina A1 do A11 u nastavku:
[image]
15. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što je E monociklička skupina.
16. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što je E arilna ili heteroarilna skupina od kojih je svaka nesupstituirana ili supstituirana sa do 4 supstituenta R8 kako je definirano u zahtjevu 1.
17. Spoj prema zahtjevu 17, naznačen time što je izabran između po izboru supstituiranog fenila, tiofena, furana, pirimidina i piridina, od kojih je svaki nesupstituiran ili supstituiran sa do 4 supstituenta R8 kako je definirano u zahtjevu 1.
18. Spoj prema zahtjevu 18, naznačen time što je E fenil koji nije supstituiran ili može biti supstituiran sa do 4 supstituenta R8 kako je definirano u zahtjevu 1.
19. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što su skupina A i pirazol spojeni na skupinu E u meta ili para položaju; tj. A i pirazol nisu spojeni na susjedne članove prstena skupine.
20. Spoj prema zahtjevu 20, naznačen time što je E izabran između 1,4-fenilen, 1,3-fenilen, 2,5-piridilen i 2,4-piridilen, 1,4-piperazinil, i 1,4-piperazonil, od koji je svaki nesupstituiran ili supstituirana sa do 4 supstituenta R8 kako je definirano u zahtjevu 1.
21. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što E ima 0-3 supstituenta.
22. Spoj prema zahtjevu 22, naznačen time što E ima 0-2 supstituenta.
23. Spoj prema zahtjevu 23, naznačen time što E ima 0 ili 1 supstituent.
24. Spoj prema zahtjevu 24, naznačen time što E nije supstituiran.
25. Spoj prema zahtjevu 19, naznačen time što ima formulu (II):
[image]
(II)
pri čemu je skupina A spojena u meta ili para položaju prstena benzena i q je 0-4.
26. Spoj prema zahtjevu 26, naznačen time što q je 0, 1 ili 2
27. Spoj prema zahtjevu 27, naznačen time što q je 0 ili 1.
28. Spoj prema zahtjevu 28, naznačen time što q je 0.
29. Spoj prema zahtjevu 19, naznačen time što ima formulu (III):
[image]
(III)
gdje je A’ ostatak skupine A i R1 do R5 su kako je defnirano u bilo kojem od prethodnih zahtjeva.
30. Spoj prema zahtjevu 19, naznačen time što ima formulu (IV):
[image]
(IV)
gdje z je 0, 1 ili 2, R20 je izabran između vodika, metila, hidroksi i fluora, uz uvjet da kada je z jednako 0, R20 nije hidroksi.
31. Spoj prema zahtjevu 19, naznačen time što ima formulu (V):
[image]
(V)
gdje je R3 izabran između vodika i C1-4 hidrokarbila.
32. Spoj prema zahtjevu 32, naznačen time što R3 je vodik.
33. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što je R1 izabran između fenil, naftil, tienil, furan, pirimidin i piridin, od kojih svaki može po izboru biti supstituiran kako je definirano u zahtjevu 1.
34. Spoj prema zahtjevu 26, naznačen time što je R1 fenil.
35. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što R1 nije supstituiran ili je supstituiran sa do 5 supstituenta izabrana između hidroksi, C1-4 aciloksi, fluor, klor, brom, trifluorometil, cijano, C1-4 hidrokarbiloksi i C1-4 hidrokarbil po izboru supstituiran s C1-2 alkoksi ili hidroksi.
36. Spoj prema zahtjevu 36, naznačen time što skupina R1 ima jedan ili dva supstituenta izabrana između fluor, klor, trifluorometil, metil i metoksi.
37. Spoj prema zahtjevu 37, naznačen time što je R1 mono-klorofenil ili diklorofenil skupina.
38. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što je R4 izabran između vodika i metila.
39. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što je R5 izabran između vodika, metila i cijano.
40. Spoj prema zahtjevu 40, naznačen time što je R5 vodik ili metil.
41. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što su R2 i R3 nezavisno jedan od drugoga izabrani između vodika, C1-4 hidrokarbil i C1-4 acil
42. Spoj prema zahtjevu 42, naznačen time što su R2 i R3 nezavisno jedan od drugoga izabrani između vodika i metila.
43. Spoj prema zahtjevu 43, naznačen time što su oba R2i R3 vodik.
44. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što ima molekulsku težinu manju od 525.
45. Spoj prema zahtjevu 1 formule (I), naznačen time što je:
2-fenil-2-[4-(1H-pirazol-4-il)-fenil]-etilamin;
3-fenil-2-[3-(1H-pirazol-4-il)-fenil]-propionitril;
2-[4-(3,5-dimetil-1H-pirazol-4-il)-fenil]-2-fenil-etilamin;
2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etilamin;
2-[3-(3,5-dimetil-1H-pirazol-4-il)-fenil]-1-fenil-etilamin;
3-fenil-2-[3-(1H-pirazol-4-il)-fenil]-propilamin;
3-fenil-2-[4-(1H-pirazol-4-il)-fenil]-propilamin;
{3-(4-kloro-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propil}-metil-amin;
{3-(3,4-difluoro-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propil}-metil-amin;
{3-(3-kloro-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propil}-metil-amin;
3-(4-kloro-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propionamid;
3-(4-kloro-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propilamin;
3-(3,4-dikloro-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propilamin;
4-(4-kloro-fenil)-4-[4-(1H-pirazol-4-il)-fenil]-piperidin;
4-(4-metoksi-fenil)-4-[4-(1H-pirazol-4-il)-fenil]-piperidin;
4-(4-kloro-fenil)-1-metil-4-[4-(1H-pirazol-4-il)-fenil]-piperidin;
4-fenil-4-[4-(1H-pirazol-4-il)-fenil]-piperidin;
4-[4-(3,5-dimetil-1H-pirazol-4-il)-fenil]-4-fenil-piperidin;
dimetil-{3-[4-(1H-pirazol-4-il)-fenil]-3-piridin-2-il-propil}-amin;
{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-dimetil-amin;
{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-metil-amin;
{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-metil-amin (R);
{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-metil-amin (S);
4-{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-morfolin;
4-{4-[1-(4-kloro-fenil)-2-pirolidin-1-il-etil]-fenil}-1H-pirazol;
{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-izopropil-amin;
dimetil-{2-fenil-2-[4-(1H-pirazol-4-il)-fenil]-etil}-amin;
{2,2-bis-[4-(1H-pirazol-4-il)-fenil]-etil}-dimetil-amin;
{2,2-bis-[4-(1H-pirazol-4-il)-fenil]-etil}-metil-amin;
2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etilamin (R);
2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etilamin (S);
2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-acetamid;
1-{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-piperazin;
1-{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-piperidin;
4-{4-[2-azetidin-1-il-1-(4-kloro-fenil)-etil]-fenil}-1H-pirazol;
1-fenil-2-[4-(1H-pirazol-4-il)-fenil]-etilamin;
2-(4-kloro-fenil)-N-metil-2-[4-(1H-pirazol-4-il)-fenil]-acetamid;
N-metil-2,2-bis-[4-(1H-pirazol-4-il)-fenil]-acetamid;
{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-metil-amin;
{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-etil-amin;
4-{4-[1-(4-kloro-fenil)-2-imidazol-1-il-etil]-fenil}-1H-pirazol;
metil-{2-(4-fenoksi-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-amin;
{2-(4-metoksi-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-metil-amin;
metil-{2-[4-(pirazin-2-iloksi)-fenil]-2-[4-(1H-pirazol-4-il)-fenil]-etil}-amin;
metil-{2-fenoksi-2-[4-(1H-pirazol-4-il)-fenil]-etil}-amin;
2-{(4-kloro-fenil)-[4-(1H-pirazol-4-il)-fenil]-metoksi}-etilamin;
4-{4-[1-(4-kloro-fenil)-3-pirolidin-1-il-propil]-fenil}-1H-pirazol;
4-{4-[3-azetidin-1-il-1-(4-kloro-fenil)-propil]-fenil}-1H-pirazol;
metil-{3-naftalen-2-il-3-[4-(1H-pirazol-4-il)-fenil]-propil}-amin;
{3-(4-fluoro-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propil}-metil-amin;
4-{4-[4-(4-kloro-fenil)-piperidin-4-il]-fenil}-1H-pirazol-3-karbonitril;
3-(4-fenoksi-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propilamin;
1-{(4-kloro-fenil)-[4-(1H-pirazol-4-il)-fenil]-metil}-piperazin;
1-metil-4-{fenil-[4-(1H-pirazol-4-il)-fenil]-metil}-[1,4]diazepan;
{3-(3-kloro-fenoksi)-3-[4-(1H-pirazol-4-il)-fenil]-propil}-metil-amin;
metil-{2-fenil-2-[6-(1H-pirazol-4-il)-piridin-3-il]-etil}-amin;
4-{4-[1-(4-kloro-fenil)-3-imidazol-1-il-propil]-fenil}-1H-pirazol;
4-[4-(3-imidazol-1-il-1-fenoksi-propil)-fenil]-1H-pirazol;
4-{4-[4-(1H-pirazol-4-il)-fenil]-piperidin-4-il}-fenol;
1-{(4-kloro-fenil)-[4-(1H-pirazol-4-il)-fenil]-metil}-piperazin;
{2-(4-fluoro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-metil-amin;
{2-(3-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-metil-amin;
4-[4-(2-metoksi-etoksi)-fenil]-4-[4-(1H-pirazol-4-il)-fenil]-piperidin;
4-[4-(3-metoksi-propoksi)-fenil]-4-[4-(1H-pirazol-4-il)-fenil]-piperidin;
3-(3,4-dikloro-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propionamid;
2-(4-{2-metilamino-1-[4-(1H-pirazol-4-il)-fenil]-etil}-fenoksi)-izonikotinamid;
{2-(3-kloro-fenoksi)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-metil-amin;
3-{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etilamino}-propan-1-ol;
2-{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etilamino}-etanol;
3-{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etilamino}-propan-1-ol;
2-{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etilamino}-etanol;
{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-ciklopropilmetil-amin;
metil-[2-[4-(1H-pirazol-4-il)-fenil]-2-(4-piridin-3-il-fenil)-etil]-amin;
4-{3-metilamino-1-[4-(1H-pirazol-4-il)-fenil]-propil}-fenol;
3-(4-metoksi-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propilamin;
4-(4-kloro-fenil)-4-[4-(3-metil-1H-pirazol-4-il)-fenil]-piperidin;
2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-morfolin;
(4-{4-[4-(1H-pirazol-4-il)-fenil]-piperidin-4-il}-fenoksi)-octena kiselina;
4-{4-[4-(1H-pirazol-4-il)-fenil]-piperidin-4-il}-benzonitril;
{2-(4-kloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-propil}-metil-amin;
1-(4-kloro-fenil)-2-metilamino-1-[4-(1H-pirazol-4-il)-fenil]-etanol;
2-amino-1-(4-kloro-fenil)-1-[4-(1H-pirazol-4-il)-fenil]-etanol;
4-(3,4-dikloro-fenil)-4-[4-(1H-pirazol-4-il)-fenil]-piperidin;
4-(3-kloro-4-metoksi-fenil)-4-[4-(1H-pirazol-4-il)-fenil]-piperidin;
4-(4-kloro-3-fluoro-fenil)-4-[4-(1H-pirazol-4-il)-fenil]-piperidin;
4-[4-(1H-pirazol-4-il)-fenil]-1,2,3,4,5,6-hexahidro-[4,4']bipiridinil;
3-(3-kloro-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propilamin;
2-metilamino-1-(4-nitro-fenil)-1-[4-(1H-pirazol-4-il)-fenil]-etanol;
2-(3-kloro-4-metoksi-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etilamin;
2-(4-kloro-fenil)-2-fluoro-2-[4-(1H-pirazol-4-il)-fenil]-etilamin;
3-(3,4-dikloro-fenil)-3-[6-(1H-pirazol-4-il)-piridin-3-il]-propilamin;
2-(4-kloro-3-fluoro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etilamin;
4-(2-kloro-3-fluoro-fenil)-4-[4-(1H-pirazol-4-il)-fenil]-piperidin;
1-{(3,4-dikloro-fenil)-[4-(1H-pirazol-4-il)-fenil]-metil}-piperazin;
2-(3,4-dikloro-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etilamin;
{2-(3-kloro-4-metoksi-fenil)-2-[4-(1H-pirazol-4-il)-fenil]-etil}-metil-amin;
4-{4-[2-azetidin-1-il-1-(4-kloro-fenoksi)-etil]-fenil}-1H-pirazol;
3-(3-kloro-4-metoksi-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propilamin;
{3-(3-kloro-4-metoksi-fenil)-3-[4-(1H-pirazol-4-il)-fenil]-propil}-metil-amin;
1-{(3,4-dikloro-fenil)-[4-(1H-pirazol-4-il)-fenil]-metil}-piperazin; ili
C-(4-kloro-fenil)-C-[4-(1H-pirazol-4-il)-fenil]-metilamin;
i njihove soli, solvati, tautomeri i N-oksidi.
46. Spoj prema zahtjevu 46, naznačen time što je 2-amino-1-(4-kloro-fenil)-1-[4-(1H-pirazol-4-il)-fenil]-etanol ili njegova sol, solvat, tautomer ili N-oksid.
47. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time što je u obliku soli, solvata, estera ili N-oksida.
48. Spoj kako je definiran u bilo kojem od zahtjeva 1 do 48, naznačen time što se koristi u medicini.
49. Spoj kako je definiran u bilo kojem od zahtjeva 1 do 48, naznačen time što se koristi za (a) prevenciju ili liječenje bolesti ili stanja posredovanog protein kinazom B; ili (b) za prevenciju ili liječenje bolesti ili stanja posredovanog protein kinazom A.
50. Spoj kako je definiran u bilo kojem od zahtjeva 1 do 48, naznačen time što se koristi za prevenciju ili liječenje bolesti ili stanja izabranih iz skupine karcinoma mjehura, dojke, kolona, bubrega, epiderme, jetre, pluća, jednjaka, žučnog mjehura, jajnika, gušterače, želuca, grlića maternice, endometrija, štitnjače, prostate ili kože, hematopoetskih tumora limfoidne linije, hematopoetskih tumora mijeloične linije, folikularnog karcinoma štitnjače, tumora mezenhimskog porijekla, tumora središnjeg ili perifernog živčanog sustava, melanoma, seminoma, teratokarcinoma, osteosarkoma, xeroderma pigmentosum, keratoksantoma, folikularnog karcinoma štitnjače ili Kaposijevog sarkoma.
51. Spoj kako je definiran u bilo kojem od zahtjeva 1 do 48, naznačen time što se koristi za prevenciju ili liječenje bolesti ili stanja izabranih iz skupine raka dojke, raka jajnika, raka kolona, raka prostate, raka jednjaka, skvamoznog karcinoma i karcinoma ne-malih stanica pluća.
52. Uporaba spoja kako je definiran u bilo kojem od zahtjeva 1 do 48, naznačena time što se radi o uporabi za:
(a) proizvodnju lijeka za prevenciju ili liječenje bolesti ili stanja posredovanog protein kinazom B; ili
(b) proizvodnju lijeka za prevenciju ili liječenje bolesti ili stanja posredovanog protein kinazom A; ili
(c) proizvodnju lijeka za prevenciju ili liječenje bolesti ili stanja koje proizlazi iz abnormalnog rasta stanica;
(d) proizvodnju lijeka za prevenciju ili liječenje bolesti kod koje postoji poremećaj proliferacije, apoptoze ili diferencijacije.
53. Farmaceutska smjesa, naznačena time što sadrži novi spoj kako je definiran u bilo kojem od zahtjeva 1 do 48 i farmaceutski prihvatljiv nosač.
54. Postupak pripreme spoja formule (I) kako je definiran u bilo kojem od zahtjeva 1 do 48, naznačen time što obuhvaća:
(a) reakciju spoja formule (X) sa spojem formule (XI) ili njegovim N-zaštićenim derivatom:
[image]
u prisutnosti paladijevog katalizatora i baze, gdje su A, E, i R1 do R5 kako su definirani u bilo kojem od zahtjeva 1 do 48, jedna od skupina X i Y je izabrana između klora, broma, joda i trifluorometansulfonata, a druga od skupina X i Y je boronat ester ili ostatak boronske kiseline;
(b) reduktivnu aminaciju spoja formule (XXXVI):
[image]
(XXXVI)
s HNR2R3 u prisutnosti reducensa; i po izboru
(c) pretvorbu jednog spoja formule (I) u drugi spoj formule (I).
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-
2004
- 2004-12-23 NZ NZ547696A patent/NZ547696A/en not_active IP Right Cessation
- 2004-12-23 PL PL04806258T patent/PL1706385T3/pl unknown
- 2004-12-23 BR BRPI0418078A patent/BRPI0418078A8/pt active Search and Examination
- 2004-12-23 JP JP2006546339A patent/JP4928949B2/ja not_active Expired - Fee Related
- 2004-12-23 EP EP10168024A patent/EP2228369A1/en not_active Withdrawn
- 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 EP EP04806258A patent/EP1706385B1/en active Active
- 2004-12-23 MX MXPA06007326A patent/MXPA06007326A/es active IP Right Grant
- 2004-12-23 WO PCT/GB2004/005464 patent/WO2005061463A1/en active Application Filing
- 2004-12-23 KR KR1020067014742A patent/KR101164258B1/ko not_active IP Right Cessation
- 2004-12-23 US US10/596,788 patent/US8247576B2/en not_active Expired - Fee Related
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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
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2007
- 2007-04-03 HK HK07103603.6A patent/HK1097543A1/xx not_active IP Right Cessation
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2010
- 2010-12-07 HR HR20100675T patent/HRP20100675T1/hr unknown
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2011
- 2011-01-03 CY CY20111100002T patent/CY1111493T1/el unknown
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2012
- 2012-06-28 US US13/536,174 patent/US8691806B2/en not_active Expired - Fee Related
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2014
- 2014-02-14 US US14/180,440 patent/US9283226B2/en not_active Expired - Fee Related
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Also Published As
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IL176400A (en) | 2011-10-31 |
WO2005061463A1 (en) | 2005-07-07 |
KR20060130621A (ko) | 2006-12-19 |
HK1097543A1 (en) | 2007-06-29 |
US9283226B2 (en) | 2016-03-15 |
AU2004303602C1 (en) | 2009-05-28 |
EP1706385B1 (en) | 2010-10-06 |
US20160250187A1 (en) | 2016-09-01 |
JP2007516272A (ja) | 2007-06-21 |
US8247576B2 (en) | 2012-08-21 |
NO20062633L (no) | 2006-07-20 |
UY28946A1 (es) | 2006-01-31 |
CY1111493T1 (el) | 2015-08-05 |
US20110144080A1 (en) | 2011-06-16 |
EP1706385A1 (en) | 2006-10-04 |
BRPI0418078A (pt) | 2007-04-17 |
BRPI0418078A8 (pt) | 2018-01-02 |
EP2228369A1 (en) | 2010-09-15 |
MXPA06007326A (es) | 2007-01-26 |
CA2548374A1 (en) | 2005-07-07 |
US20140271662A1 (en) | 2014-09-18 |
US20130005702A1 (en) | 2013-01-03 |
NZ547696A (en) | 2009-12-24 |
KR101164258B1 (ko) | 2012-07-11 |
PL1706385T3 (pl) | 2011-03-31 |
US8691806B2 (en) | 2014-04-08 |
JP4928949B2 (ja) | 2012-05-09 |
IL176400A0 (en) | 2006-10-05 |
AU2004303602B2 (en) | 2008-12-18 |
AU2004303602A1 (en) | 2005-07-07 |
CA2548374C (en) | 2014-05-27 |
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