JP2005516934A5 - - Google Patents
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- Publication number
- JP2005516934A5 JP2005516934A5 JP2003552720A JP2003552720A JP2005516934A5 JP 2005516934 A5 JP2005516934 A5 JP 2005516934A5 JP 2003552720 A JP2003552720 A JP 2003552720A JP 2003552720 A JP2003552720 A JP 2003552720A JP 2005516934 A5 JP2005516934 A5 JP 2005516934A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- alkyl
- phenyl
- cycloalkyl
- pyridine
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 228
- 125000003118 aryl group Chemical group 0.000 claims 65
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 58
- 229910052736 halogen Inorganic materials 0.000 claims 54
- 150000002367 halogens Chemical class 0.000 claims 54
- 125000001424 substituent group Chemical group 0.000 claims 47
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 46
- 150000001875 compounds Chemical class 0.000 claims 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims 41
- 125000001072 heteroaryl group Chemical group 0.000 claims 37
- 150000003839 salts Chemical class 0.000 claims 24
- 125000003342 alkenyl group Chemical group 0.000 claims 23
- 125000000304 alkynyl group Chemical group 0.000 claims 23
- 239000003814 drug Substances 0.000 claims 15
- 238000004519 manufacturing process Methods 0.000 claims 14
- 230000002265 prevention Effects 0.000 claims 14
- HCUOEKSZWPGJIM-IYNMRSRQSA-N (e,2z)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N\O)\C(N)=O HCUOEKSZWPGJIM-IYNMRSRQSA-N 0.000 claims 12
- -1 —C 3-7 cycloalkyl Chemical group 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- XGJDYRGPTCNKRO-UHFFFAOYSA-N 2-[1-(3-fluorophenyl)pyrazol-4-yl]pyridine Chemical compound FC1=CC=CC(N2N=CC(=C2)C=2N=CC=CC=2)=C1 XGJDYRGPTCNKRO-UHFFFAOYSA-N 0.000 claims 2
- PRERRRRWTXTVFH-UHFFFAOYSA-N 2-[1-(5-bromo-2-methylphenyl)pyrazol-4-yl]-1,3-benzoxazole Chemical compound CC1=CC=C(Br)C=C1N1N=CC(C=2OC3=CC=CC=C3N=2)=C1 PRERRRRWTXTVFH-UHFFFAOYSA-N 0.000 claims 2
- LQROCYQCXGUXNA-UHFFFAOYSA-N 3-(1-pyridin-2-ylpyrazol-3-yl)benzonitrile Chemical compound N#CC1=CC=CC(C2=NN(C=C2)C=2N=CC=CC=2)=C1 LQROCYQCXGUXNA-UHFFFAOYSA-N 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 229960002069 diamorphine Drugs 0.000 claims 2
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 229940044601 receptor agonist Drugs 0.000 claims 2
- 239000000018 receptor agonist Substances 0.000 claims 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 1
- AZCQSLLNCTWOOX-UHFFFAOYSA-N 1-[4-[4-(4-methylquinolin-2-yl)pyrazol-1-yl]phenyl]imidazolidin-2-one Chemical compound N=1C2=CC=CC=C2C(C)=CC=1C(=C1)C=NN1C(C=C1)=CC=C1N1CCNC1=O AZCQSLLNCTWOOX-UHFFFAOYSA-N 0.000 claims 1
- HCQIQZQNRDZGNQ-UHFFFAOYSA-N 1-methyl-3-[4-(4-pyrimidin-4-ylpyrazol-1-yl)phenyl]imidazolidin-2-one Chemical compound O=C1N(C)CCN1C1=CC=C(N2N=CC(=C2)C=2N=CN=CC=2)C=C1 HCQIQZQNRDZGNQ-UHFFFAOYSA-N 0.000 claims 1
- WYAMKHRQXSRODZ-UHFFFAOYSA-N 1-methyl-3-[4-(4-quinolin-2-ylpyrazol-1-yl)phenyl]imidazolidin-2-one Chemical compound O=C1N(C)CCN1C1=CC=C(N2N=CC(=C2)C=2N=C3C=CC=CC3=CC=2)C=C1 WYAMKHRQXSRODZ-UHFFFAOYSA-N 0.000 claims 1
- QAGWIDVRNVVCKE-UHFFFAOYSA-N 1-methyl-3-[4-(4-quinoxalin-2-ylpyrazol-1-yl)phenyl]imidazolidin-2-one Chemical compound O=C1N(C)CCN1C1=CC=C(N2N=CC(=C2)C=2N=C3C=CC=CC3=NC=2)C=C1 QAGWIDVRNVVCKE-UHFFFAOYSA-N 0.000 claims 1
- DGFLPDKYGMWBIX-UHFFFAOYSA-N 1-methyl-3-[4-[4-(4-methylquinolin-2-yl)pyrazol-1-yl]phenyl]imidazolidin-2-one Chemical compound O=C1N(C)CCN1C1=CC=C(N2N=CC(=C2)C=2N=C3C=CC=CC3=C(C)C=2)C=C1 DGFLPDKYGMWBIX-UHFFFAOYSA-N 0.000 claims 1
- OKNXPKMPVBXAKH-UHFFFAOYSA-N 2-(1-naphthalen-1-ylpyrazol-4-yl)pyridine Chemical compound C1=NN(C=2C3=CC=CC=C3C=CC=2)C=C1C1=CC=CC=N1 OKNXPKMPVBXAKH-UHFFFAOYSA-N 0.000 claims 1
- FVLVFEGTAANRQW-UHFFFAOYSA-N 2-(1-naphthalen-2-ylpyrazol-4-yl)-1,3-benzoxazole Chemical compound C1=CC=CC2=CC(N3N=CC(=C3)C=3OC4=CC=CC=C4N=3)=CC=C21 FVLVFEGTAANRQW-UHFFFAOYSA-N 0.000 claims 1
- HUJPTNVCZQRVHZ-UHFFFAOYSA-N 2-(1-naphthalen-2-ylpyrazol-4-yl)pyridine Chemical compound C1=NN(C=2C=C3C=CC=CC3=CC=2)C=C1C1=CC=CC=N1 HUJPTNVCZQRVHZ-UHFFFAOYSA-N 0.000 claims 1
- AJOUJDIOWGIZRL-UHFFFAOYSA-N 2-(1-phenylpyrazol-3-yl)pyridine Chemical compound C1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=N1 AJOUJDIOWGIZRL-UHFFFAOYSA-N 0.000 claims 1
- RKVUMPNIGODVPF-UHFFFAOYSA-N 2-(1-phenylpyrazol-4-yl)-1,3-benzoxazole Chemical compound C1=C(C=2OC3=CC=CC=C3N=2)C=NN1C1=CC=CC=C1 RKVUMPNIGODVPF-UHFFFAOYSA-N 0.000 claims 1
- WXKZWTBZUQXDBS-UHFFFAOYSA-N 2-(1-phenylpyrazol-4-yl)quinoxaline Chemical compound C1=C(C=2N=C3C=CC=CC3=NC=2)C=NN1C1=CC=CC=C1 WXKZWTBZUQXDBS-UHFFFAOYSA-N 0.000 claims 1
- TYHMKJWOGASESG-UHFFFAOYSA-N 2-(1-pyridin-2-ylpyrazol-3-yl)pyridine Chemical compound C1=CN(C=2N=CC=CC=2)N=C1C1=CC=CC=N1 TYHMKJWOGASESG-UHFFFAOYSA-N 0.000 claims 1
- JVCVIEXWXSZFDG-UHFFFAOYSA-N 2-(1-pyridin-2-ylpyrazol-4-yl)-1,3-benzoxazole Chemical compound C1=C(C=2OC3=CC=CC=C3N=2)C=NN1C1=CC=CC=N1 JVCVIEXWXSZFDG-UHFFFAOYSA-N 0.000 claims 1
- NSVSMFPAARLLMH-UHFFFAOYSA-N 2-(1-pyridin-3-ylpyrazol-4-yl)pyridine Chemical compound C1=NN(C=2C=NC=CC=2)C=C1C1=CC=CC=N1 NSVSMFPAARLLMH-UHFFFAOYSA-N 0.000 claims 1
- WEBAMACTWTXRHC-UHFFFAOYSA-N 2-(1-quinolin-6-ylpyrazol-4-yl)quinoxaline Chemical compound N1=CC=CC2=CC(N3N=CC(=C3)C=3N=C4C=CC=CC4=NC=3)=CC=C21 WEBAMACTWTXRHC-UHFFFAOYSA-N 0.000 claims 1
- LWZZBDVBWZSHRQ-UHFFFAOYSA-N 2-(3-pyridin-2-ylpyrazol-1-yl)-5-(trifluoromethyl)pyridine Chemical compound N1=CC(C(F)(F)F)=CC=C1N1N=C(C=2N=CC=CC=2)C=C1 LWZZBDVBWZSHRQ-UHFFFAOYSA-N 0.000 claims 1
- LOACHQITIDPKNZ-UHFFFAOYSA-N 2-(3-pyridin-2-ylpyrazol-1-yl)pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC(N2N=C(C=C2)C=2N=CC=CC=2)=C1 LOACHQITIDPKNZ-UHFFFAOYSA-N 0.000 claims 1
- DHCPDJYATWWMSN-UHFFFAOYSA-N 2-(4-naphthalen-1-ylpyrazol-1-yl)pyridine Chemical compound C1=C(C=2C3=CC=CC=C3C=CC=2)C=NN1C1=CC=CC=N1 DHCPDJYATWWMSN-UHFFFAOYSA-N 0.000 claims 1
- OUIYUXHEXYCKDT-UHFFFAOYSA-N 2-(4-naphthalen-2-ylpyrazol-1-yl)pyridine Chemical compound C1=C(C=2C=C3C=CC=CC3=CC=2)C=NN1C1=CC=CC=N1 OUIYUXHEXYCKDT-UHFFFAOYSA-N 0.000 claims 1
- MGPUTXLFCNIIDB-UHFFFAOYSA-N 2-(4-pyridin-2-ylpyrazol-1-yl)-1,3-benzoxazole Chemical compound C1=NN(C=2OC3=CC=CC=C3N=2)C=C1C1=CC=CC=N1 MGPUTXLFCNIIDB-UHFFFAOYSA-N 0.000 claims 1
- GCURMULFLLASSI-UHFFFAOYSA-N 2-(4-pyrimidin-4-ylpyrazol-1-yl)-1,3-benzoxazole Chemical compound C1=NN(C=2OC3=CC=CC=C3N=2)C=C1C1=CC=NC=N1 GCURMULFLLASSI-UHFFFAOYSA-N 0.000 claims 1
- VOGGFKHGYKLRSP-UHFFFAOYSA-N 2-(4-pyrimidin-4-ylpyrazol-1-yl)quinoline Chemical compound C1=NN(C=2N=C3C=CC=CC3=CC=2)C=C1C1=CC=NC=N1 VOGGFKHGYKLRSP-UHFFFAOYSA-N 0.000 claims 1
- QGXRQCJTGVNIOL-UHFFFAOYSA-N 2-[(4-pyridin-2-ylpyrazol-1-yl)methyl]benzonitrile Chemical compound N#CC1=CC=CC=C1CN1N=CC(C=2N=CC=CC=2)=C1 QGXRQCJTGVNIOL-UHFFFAOYSA-N 0.000 claims 1
- XGKIOTUJMORYMB-UHFFFAOYSA-N 2-[1-(1,3-benzoxazol-2-yl)pyrazol-4-yl]-1,3-benzoxazole Chemical compound C1=CC=C2OC(N3N=CC(=C3)C=3OC4=CC=CC=C4N=3)=NC2=C1 XGKIOTUJMORYMB-UHFFFAOYSA-N 0.000 claims 1
- SFYWQOYENADHNQ-UHFFFAOYSA-N 2-[1-(1h-indazol-5-yl)pyrazol-4-yl]quinoxaline Chemical compound C1=CC2=NNC=C2C=C1N1N=CC(C=2N=C3C=CC=CC3=NC=2)=C1 SFYWQOYENADHNQ-UHFFFAOYSA-N 0.000 claims 1
- CCTGYZJNXLFPCK-UHFFFAOYSA-N 2-[1-(1h-indazol-6-yl)pyrazol-4-yl]quinoxaline Chemical compound C1=C2C=NNC2=CC(N2N=CC(=C2)C=2N=C3C=CC=CC3=NC=2)=C1 CCTGYZJNXLFPCK-UHFFFAOYSA-N 0.000 claims 1
- XNEHRZTXLKVXFE-UHFFFAOYSA-N 2-[1-(2,3,4,5,6-pentafluorophenyl)pyrazol-3-yl]pyridine Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1N1N=C(C=2N=CC=CC=2)C=C1 XNEHRZTXLKVXFE-UHFFFAOYSA-N 0.000 claims 1
- NKYDDENOHDIDDG-UHFFFAOYSA-N 2-[1-(2,3,5,6-tetrafluorophenyl)pyrazol-3-yl]pyridine Chemical compound FC1=CC(F)=C(F)C(N2N=C(C=C2)C=2N=CC=CC=2)=C1F NKYDDENOHDIDDG-UHFFFAOYSA-N 0.000 claims 1
- WAKQIVHDDIYKIV-UHFFFAOYSA-N 2-[1-(2,3,5-trifluorophenyl)pyrazol-3-yl]pyridine Chemical compound FC1=CC(F)=C(F)C(N2N=C(C=C2)C=2N=CC=CC=2)=C1 WAKQIVHDDIYKIV-UHFFFAOYSA-N 0.000 claims 1
- YEVNOZNLPXBQNO-UHFFFAOYSA-N 2-[1-(2,3-dihydro-1h-inden-5-yl)pyrazol-4-yl]quinoxaline Chemical compound C1=CC=CC2=NC(C3=CN(N=C3)C3=CC=C4CCCC4=C3)=CN=C21 YEVNOZNLPXBQNO-UHFFFAOYSA-N 0.000 claims 1
- ZAVCTYLELRPUMV-UHFFFAOYSA-N 2-[1-(2,3-dimethylphenyl)pyrazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(N2N=CC(=C2)C=2N=C3C=CC=CC3=NC=2)=C1C ZAVCTYLELRPUMV-UHFFFAOYSA-N 0.000 claims 1
- QUPZJTDJFCMCJA-UHFFFAOYSA-N 2-[1-(2,4-dichlorophenyl)pyrazol-4-yl]-1,3-benzoxazole Chemical compound ClC1=CC(Cl)=CC=C1N1N=CC(C=2OC3=CC=CC=C3N=2)=C1 QUPZJTDJFCMCJA-UHFFFAOYSA-N 0.000 claims 1
- KBMGFEFAEMCBON-UHFFFAOYSA-N 2-[1-(2,4-difluorophenyl)pyrazol-3-yl]pyridine Chemical compound FC1=CC(F)=CC=C1N1N=C(C=2N=CC=CC=2)C=C1 KBMGFEFAEMCBON-UHFFFAOYSA-N 0.000 claims 1
- VMIUAEVMJRSFRZ-UHFFFAOYSA-N 2-[1-(2,4-dimethylphenyl)pyrazol-4-yl]-1,3-benzoxazole Chemical compound CC1=CC(C)=CC=C1N1N=CC(C=2OC3=CC=CC=C3N=2)=C1 VMIUAEVMJRSFRZ-UHFFFAOYSA-N 0.000 claims 1
- HPAUWVCTOKACAJ-UHFFFAOYSA-N 2-[1-(2,4-dimethylphenyl)pyrazol-4-yl]quinoxaline Chemical compound CC1=CC(C)=CC=C1N1N=CC(C=2N=C3C=CC=CC3=NC=2)=C1 HPAUWVCTOKACAJ-UHFFFAOYSA-N 0.000 claims 1
- ZQDYDXHRWYIYRM-UHFFFAOYSA-N 2-[1-(2,5-dichlorophenyl)pyrazol-4-yl]quinoxaline Chemical compound ClC1=CC=C(Cl)C(N2N=CC(=C2)C=2N=C3C=CC=CC3=NC=2)=C1 ZQDYDXHRWYIYRM-UHFFFAOYSA-N 0.000 claims 1
- XCGFLUXUXAUEDU-UHFFFAOYSA-N 2-[1-(2,5-difluorophenyl)pyrazol-3-yl]pyridine Chemical compound FC1=CC=C(F)C(N2N=C(C=C2)C=2N=CC=CC=2)=C1 XCGFLUXUXAUEDU-UHFFFAOYSA-N 0.000 claims 1
- YCZURQMROUEVNH-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)pyrazol-4-yl]quinoxaline Chemical compound CC1=CC=C(C)C(N2N=CC(=C2)C=2N=C3C=CC=CC3=NC=2)=C1 YCZURQMROUEVNH-UHFFFAOYSA-N 0.000 claims 1
- VAOHZOIDCYFDEN-UHFFFAOYSA-N 2-[1-(2,6-dimethylphenyl)pyrazol-4-yl]-1,3-benzoxazole Chemical compound CC1=CC=CC(C)=C1N1N=CC(C=2OC3=CC=CC=C3N=2)=C1 VAOHZOIDCYFDEN-UHFFFAOYSA-N 0.000 claims 1
- HOYKKRFYORCYEJ-UHFFFAOYSA-N 2-[1-(2,6-dimethylphenyl)pyrazol-4-yl]pyridine Chemical compound CC1=CC=CC(C)=C1N1N=CC(C=2N=CC=CC=2)=C1 HOYKKRFYORCYEJ-UHFFFAOYSA-N 0.000 claims 1
- QWKGWLARLNDIGE-UHFFFAOYSA-N 2-[1-(2,6-dimethylphenyl)pyrazol-4-yl]quinoline Chemical compound CC1=CC=CC(C)=C1N1N=CC(C=2N=C3C=CC=CC3=CC=2)=C1 QWKGWLARLNDIGE-UHFFFAOYSA-N 0.000 claims 1
- IDLFVLGRIXGGKP-UHFFFAOYSA-N 2-[1-(2,6-dimethylphenyl)pyrazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(C)=C1N1N=CC(C=2N=C3C=CC=CC3=NC=2)=C1 IDLFVLGRIXGGKP-UHFFFAOYSA-N 0.000 claims 1
- LKLRCXLOPXQEAW-UHFFFAOYSA-N 2-[1-(2-benzylphenyl)pyrazol-4-yl]pyridine Chemical compound C=1C=CC=C(N2N=CC(=C2)C=2N=CC=CC=2)C=1CC1=CC=CC=C1 LKLRCXLOPXQEAW-UHFFFAOYSA-N 0.000 claims 1
- BCRRWHWWGLXLHN-UHFFFAOYSA-N 2-[1-(2-benzylphenyl)pyrazol-4-yl]quinoxaline Chemical compound C=1C=CC=C(N2N=CC(=C2)C=2N=C3C=CC=CC3=NC=2)C=1CC1=CC=CC=C1 BCRRWHWWGLXLHN-UHFFFAOYSA-N 0.000 claims 1
- APIBBOBQHRAAAI-UHFFFAOYSA-N 2-[1-(2-bromophenyl)pyrazol-4-yl]quinoxaline Chemical compound BrC1=CC=CC=C1N1N=CC(C=2N=C3C=CC=CC3=NC=2)=C1 APIBBOBQHRAAAI-UHFFFAOYSA-N 0.000 claims 1
- LZJQHFZLKPLHFY-UHFFFAOYSA-N 2-[1-(2-butan-2-ylphenyl)pyrazol-4-yl]-1,3-benzoxazole Chemical compound CCC(C)C1=CC=CC=C1N1N=CC(C=2OC3=CC=CC=C3N=2)=C1 LZJQHFZLKPLHFY-UHFFFAOYSA-N 0.000 claims 1
- FRERKSBQFAXBKQ-UHFFFAOYSA-N 2-[1-(2-butan-2-ylphenyl)pyrazol-4-yl]quinoline Chemical compound CCC(C)C1=CC=CC=C1N1N=CC(C=2N=C3C=CC=CC3=CC=2)=C1 FRERKSBQFAXBKQ-UHFFFAOYSA-N 0.000 claims 1
- QXYNGNKDBZVNKV-UHFFFAOYSA-N 2-[1-(2-chlorophenyl)pyrazol-4-yl]quinoxaline Chemical compound ClC1=CC=CC=C1N1N=CC(C=2N=C3C=CC=CC3=NC=2)=C1 QXYNGNKDBZVNKV-UHFFFAOYSA-N 0.000 claims 1
- YUUMMMMOOJQMBV-UHFFFAOYSA-N 2-[1-(2-fluoro-4-methylphenyl)pyrazol-4-yl]-1,3-benzoxazole Chemical compound FC1=CC(C)=CC=C1N1N=CC(C=2OC3=CC=CC=C3N=2)=C1 YUUMMMMOOJQMBV-UHFFFAOYSA-N 0.000 claims 1
- AUEOJYIOCAPFLS-UHFFFAOYSA-N 2-[1-(2-fluoro-4-methylphenyl)pyrazol-4-yl]-4-methylquinoline Chemical compound FC1=CC(C)=CC=C1N1N=CC(C=2N=C3C=CC=CC3=C(C)C=2)=C1 AUEOJYIOCAPFLS-UHFFFAOYSA-N 0.000 claims 1
- UIEBTBQXIJUUIU-UHFFFAOYSA-N 2-[1-(2-fluoro-4-methylphenyl)pyrazol-4-yl]pyridine Chemical compound FC1=CC(C)=CC=C1N1N=CC(C=2N=CC=CC=2)=C1 UIEBTBQXIJUUIU-UHFFFAOYSA-N 0.000 claims 1
- GROUYELBBXNPQA-UHFFFAOYSA-N 2-[1-(2-fluoro-4-methylphenyl)pyrazol-4-yl]quinoline Chemical compound FC1=CC(C)=CC=C1N1N=CC(C=2N=C3C=CC=CC3=CC=2)=C1 GROUYELBBXNPQA-UHFFFAOYSA-N 0.000 claims 1
- JFCVFEINEJBJMT-UHFFFAOYSA-N 2-[1-(2-fluoro-4-methylphenyl)pyrazol-4-yl]quinoxaline Chemical compound FC1=CC(C)=CC=C1N1N=CC(C=2N=C3C=CC=CC3=NC=2)=C1 JFCVFEINEJBJMT-UHFFFAOYSA-N 0.000 claims 1
- NLGYUAIOCXQGGO-UHFFFAOYSA-N 2-[1-(2-fluorophenyl)pyrazol-4-yl]quinoxaline Chemical compound FC1=CC=CC=C1N1N=CC(C=2N=C3C=CC=CC3=NC=2)=C1 NLGYUAIOCXQGGO-UHFFFAOYSA-N 0.000 claims 1
- TVJKIGPPVKPLKC-UHFFFAOYSA-N 2-[1-(2-methoxy-5-methylphenyl)pyrazol-4-yl]quinoxaline Chemical compound COC1=CC=C(C)C=C1N1N=CC(C=2N=C3C=CC=CC3=NC=2)=C1 TVJKIGPPVKPLKC-UHFFFAOYSA-N 0.000 claims 1
- HPSXOYYIYUIUMY-UHFFFAOYSA-N 2-[1-(2-methyl-5-propan-2-ylphenyl)pyrazol-4-yl]quinoxaline Chemical compound CC(C)C1=CC=C(C)C(N2N=CC(=C2)C=2N=C3C=CC=CC3=NC=2)=C1 HPSXOYYIYUIUMY-UHFFFAOYSA-N 0.000 claims 1
- RSMQDRTWLTVSGX-UHFFFAOYSA-N 2-[1-(2-methylphenyl)pyrazol-4-yl]quinoxaline Chemical compound CC1=CC=CC=C1N1N=CC(C=2N=C3C=CC=CC3=NC=2)=C1 RSMQDRTWLTVSGX-UHFFFAOYSA-N 0.000 claims 1
- ZLUZVJYSIWBTQI-UHFFFAOYSA-N 2-[1-(2-nitrophenyl)pyrazol-4-yl]quinoxaline Chemical compound [O-][N+](=O)C1=CC=CC=C1N1N=CC(C=2N=C3C=CC=CC3=NC=2)=C1 ZLUZVJYSIWBTQI-UHFFFAOYSA-N 0.000 claims 1
- KKZPHFRMXAEGRW-UHFFFAOYSA-N 2-[1-(2-phenylmethoxyphenyl)pyrazol-4-yl]quinoxaline Chemical compound C=1C=CC=C(N2N=CC(=C2)C=2N=C3C=CC=CC3=NC=2)C=1OCC1=CC=CC=C1 KKZPHFRMXAEGRW-UHFFFAOYSA-N 0.000 claims 1
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- 2002-12-13 DE DE60223720T patent/DE60223720T2/de not_active Expired - Lifetime
- 2002-12-13 ES ES02794267T patent/ES2295441T3/es not_active Expired - Lifetime
- 2002-12-13 JP JP2003552720A patent/JP4286146B2/ja not_active Expired - Fee Related
- 2002-12-13 CA CA002469813A patent/CA2469813C/en not_active Expired - Fee Related
- 2002-12-13 EP EP02794267A patent/EP1458383B1/en not_active Expired - Lifetime
- 2002-12-13 US US10/497,122 patent/US7569592B2/en active Active
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