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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Families Citing this family (93)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2048142A3 (en) * | 2001-04-26 | 2009-04-22 | Eisai R&D Management Co., Ltd. | Nitrogen-containing condensed cyclic compound having a pyrazolyl group as a substituent group and pharmaceutical composition thereof |
| EP1485093B1 (en) * | 2002-03-12 | 2010-11-03 | Merck Sharp & Dohme Corp. | Di-aryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| JP2006522128A (ja) * | 2003-04-03 | 2006-09-28 | メルク エンド カムパニー インコーポレーテッド | 代謝調節型グルタミン酸受容体−５のモジュレーターとしての４環イミダゾール誘導体 |
| EP1613614A2 (en) * | 2003-04-03 | 2006-01-11 | Merck & Co., Inc. | Di-aryl substituted pyrazole modulators of metabotropic glutamate receptor-5 |
| CN1845915A (zh) * | 2003-09-02 | 2006-10-11 | 默克公司 | 作为亲代谢谷氨酸受体－5的调节剂的联吡啶胺和醚类化合物 |
| EP1715867A4 (en) * | 2004-02-12 | 2009-04-15 | Merck & Co Inc | BIPYRIDYLAMIDE AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5 |
| WO2005080356A1 (en) * | 2004-02-18 | 2005-09-01 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonits |
| AU2005219791B2 (en) * | 2004-03-05 | 2011-06-09 | Msd K.K. | Diaryl-substituted five-membered heterocycle derivative |
| CA2560510C (en) | 2004-03-18 | 2009-10-13 | Pfizer Inc. | N-(1-arylpyrazol-4yl) sulfonamides and their use as parasiticides |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| JP2008515992A (ja) | 2004-10-13 | 2008-05-15 | ピーティーシー セラピューティクス，インコーポレーテッド | 体細胞変異に起因する疾患の阻止／治療用医薬を製造するための規定化合物の使用 |
| DE102008020113A1 (de) | 2008-04-23 | 2009-10-29 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dihydropyrazolone und ihre Verwendung |
| BRPI0517423A (pt) * | 2004-12-27 | 2008-10-07 | Astrazeneca Ab | composto, composição farmacêutica, método para o tratamento ou prevenção de distúrbios neurológicos e psiquiátricos associados com disfunção do glutamato em um animal, e, uso em um composto |
| TW200639163A (en) * | 2005-02-04 | 2006-11-16 | Genentech Inc | RAF inhibitor compounds and methods |
| CA2601098C (en) * | 2005-03-16 | 2011-07-05 | Aventis Pharmaceuticals Inc. | Dipyrazoles as central nervous system agents |
| DE102005019712A1 (de) | 2005-04-28 | 2006-11-09 | Bayer Healthcare Ag | Dipyridyl-dihydropyrazolone und ihre Verwendung |
| WO2006129193A2 (en) * | 2005-05-27 | 2006-12-07 | Pfizer Products Inc. | Combination of a cannabinoid-1- receptor-antagonist and a microsomal triglyceride transfer protein inhibitor for treating obesity or mainataining weight loss |
| EP2275096A3 (en) | 2005-08-26 | 2011-07-13 | Braincells, Inc. | Neurogenesis via modulation of the muscarinic receptors |
| EP2258357A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| WO2007047978A2 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| EP2314289A1 (en) | 2005-10-31 | 2011-04-27 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US7951824B2 (en) * | 2006-02-17 | 2011-05-31 | Hoffman-La Roche Inc. | 4-aryl-pyridine-2-carboxyamide derivatives |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| CA2643199A1 (en) * | 2006-03-08 | 2007-09-13 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| US7678808B2 (en) | 2006-05-09 | 2010-03-16 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
| EP2021000A2 (en) | 2006-05-09 | 2009-02-11 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US20100009983A1 (en) * | 2006-05-09 | 2010-01-14 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| WO2008030651A1 (en) * | 2006-09-08 | 2008-03-13 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| EP2066355A2 (en) * | 2006-09-19 | 2009-06-10 | Braincells, Inc. | Combination comprising a peroxisome proliferator activated receptor agent and a second neurogenic agent for treating a nervous system disorder, increasing neurodifferentiation and increasing neurogenesis |
| DE102006050513A1 (de) | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substitiuierte Dihydropyrazolone und ihre Verwendung |
| DE102006050516A1 (de) | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substituierte Dihydropyrazolone und ihre Verwendung |
| DE102006050515A1 (de) | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substituierte Dipyridiyl-dihydropyrazolone und ihre Verwendung |
| WO2008141731A2 (en) | 2007-05-18 | 2008-11-27 | Bayer Healthcare Ag | Inhibitors of hypoxia inducible factor (hif) useful for treating hyper-proliferative disorders and diseases associated with angiogenesis |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| WO2008151257A2 (en) | 2007-06-04 | 2008-12-11 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| WO2009028543A1 (ja) * | 2007-08-30 | 2009-03-05 | Takeda Pharmaceutical Company Limited | 置換ピラゾール誘導体 |
| ES2627848T3 (es) | 2008-06-04 | 2017-07-31 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| BRPI0916576A2 (pt) | 2008-08-04 | 2017-06-27 | Chdi Inc | pelo menos uma entidade química, composição farmacêutica, e, método para tratar uma condição ou distúrbio. |
| US20100120778A1 (en) * | 2008-11-07 | 2010-05-13 | Wyeth | Quinoxaline-based lxr modulators |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| CN102573478B (zh) * | 2009-10-12 | 2015-12-16 | 拜尔农作物科学股份公司 | 作为杀虫剂的1-(吡啶-3-基)-吡唑和1-(嘧啶-5-基)-吡唑 |
| GB201007286D0 (en) | 2010-04-30 | 2010-06-16 | Astex Therapeutics Ltd | New compounds |
| US9090632B2 (en) * | 2010-08-31 | 2015-07-28 | Vanderbilt University | Bicyclic oxazole and thiazole compounds and their use as allosteric modulators of mGluR5 receptors |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| DE102010044131A1 (de) | 2010-11-18 | 2012-05-24 | Bayer Schering Pharma Aktiengesellschaft | Substituiertes Natrium-1H-pyrazol-5-olat |
| GB201020179D0 (en) | 2010-11-29 | 2011-01-12 | Astex Therapeutics Ltd | New compounds |
| EP2651405A2 (en) * | 2010-12-14 | 2013-10-23 | Electrophoretics Limited | Casein kinase 1 (ck1 ) inhibitors |
| WO2013033068A1 (en) | 2011-08-30 | 2013-03-07 | Stephen Martin Courtney | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| SG2014012926A (en) | 2011-08-30 | 2014-06-27 | Chdi Foundation Inc | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| UA111754C2 (uk) | 2011-10-06 | 2016-06-10 | Байєр Фарма Акцієнгезелльшафт | Заміщені бензиліндазоли для застосування як інгібіторів bub1-кінази для лікування гіперпроліферативних захворювань |
| GB201118656D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118652D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118675D0 (en) | 2011-10-28 | 2011-12-14 | Astex Therapeutics Ltd | New compounds |
| GB201118654D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| US8822464B2 (en) | 2011-11-28 | 2014-09-02 | Boehringer Ingelheim International Gmbh | N-aryl-piperazine derivatives and their use as positive allosteric modulators of mGluR5 receptors |
| US8741892B2 (en) | 2011-12-05 | 2014-06-03 | Boehringer Ingelheim International Gmbh | Compounds |
| US8642774B2 (en) | 2011-12-08 | 2014-02-04 | Boehringer Ingelheim International Gmbh | Compounds |
| US8846948B2 (en) | 2011-12-13 | 2014-09-30 | Boehringer Ingelheim International Gmbh | Compounds |
| US8796467B2 (en) | 2011-12-13 | 2014-08-05 | Boehringer Ingelheim International Gmbh | Compounds |
| US8716277B2 (en) | 2011-12-14 | 2014-05-06 | Boehringer Ingelheim International Gmbh | Substituted imidazole compounds useful as positive allosteric modulators of mGlu5 receptor activity |
| US8883789B2 (en) | 2011-12-14 | 2014-11-11 | Boehringer Ingelheim International Gmbh | Piperazine derivatives and their use as positive allosteric modulators of mGluR5 receptors |
| US8937176B2 (en) | 2011-12-14 | 2015-01-20 | Boehringer Ingelheim International Gmbh | Compounds |
| CN104125957B (zh) | 2011-12-21 | 2016-05-25 | 拜耳知识产权有限责任公司 | 取代的苄基吡唑 |
| US8889677B2 (en) | 2012-01-17 | 2014-11-18 | Boehringer Ingellheim International GmbH | Substituted triazoles useful as mGlu5 receptor modulators |
| GB201209613D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| GB201209609D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| US20150284380A1 (en) * | 2012-10-31 | 2015-10-08 | Bayer Cropscience Ag | Novel heterocyclic compounds as pest control agents |
| EP2968439A2 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| GB201307577D0 (en) | 2013-04-26 | 2013-06-12 | Astex Therapeutics Ltd | New compounds |
| PL3004138T3 (pl) | 2013-06-05 | 2024-07-29 | Bausch Health Ireland Limited | Ultra-oczyszczeni agoniści peptydowi cyklazy guanylanowej C, sposób ich uzyskiwania i ich zastosowanie |
| GB201312800D0 (en) * | 2013-07-17 | 2013-08-28 | Heptares Therapeutics Ltd | mGlu5 modulators |
| BR112016022056B1 (pt) | 2014-03-26 | 2023-04-11 | Astex Therapeutics Limited | Combinação, composição farmacêutica, uso de uma combinação ou uma composição farmacêutica, e, produto farmacêutico |
| JO3512B1 (ar) | 2014-03-26 | 2020-07-05 | Astex Therapeutics Ltd | مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز |
| US10736900B2 (en) | 2014-03-26 | 2020-08-11 | Astex Therapeutics Ltd | Combinations of an FGFR inhibitor and an IGF1R inhibitor |
| WO2015161014A1 (en) * | 2014-04-17 | 2015-10-22 | Merck Sharp & Dohme Corp. | Heterocyclic cgrp receptor antagonists |
| TN2016000542A1 (en) | 2014-06-03 | 2018-04-04 | Idorsia Pharmaceuticals Ltd | Pyrazole compounds and their use as t-type calcium channel blockers |
| MX372995B (es) | 2014-07-17 | 2020-04-13 | Chdi Foundation Inc | Metodos y composiciones para el tratamiento de trastornos relacionados con vih. |
| ES2693052T3 (es) | 2014-09-15 | 2018-12-07 | Idorsia Pharmaceuticals Ltd | Compuestos de triazol como bloqueantes de los canales de calcio de tipo T |
| WO2016042084A1 (en) | 2014-09-19 | 2016-03-24 | Bayer Pharma Aktiengesellschaft | Benzyl substituted indazoles as bub1 inhibitors |
| TWI719960B (zh) | 2015-02-10 | 2021-03-01 | 英商阿斯迪克治療公司 | 新穎組成物 |
| US10478494B2 (en) | 2015-04-03 | 2019-11-19 | Astex Therapeutics Ltd | FGFR/PD-1 combination therapy for the treatment of cancer |
| WO2016202935A1 (en) | 2015-06-19 | 2016-12-22 | Bayer Pharma Aktiengesellschaft | Glucose transport inhibitors |
| HUE050567T2 (hu) | 2015-09-23 | 2020-12-28 | Janssen Pharmaceutica Nv | Triciklusos heterociklusok rák kezelésére |
| WO2017050865A1 (en) | 2015-09-23 | 2017-03-30 | Janssen Pharmaceutica Nv | Bi-heteroaryl substituted 1,4-benzodiazepines and uses thereof for the treatment of cancer |
| HRP20220463T1 (hr) | 2016-12-16 | 2022-05-27 | Idorsia Pharmaceuticals Ltd | Farmaceutska kombinacija koja sadrži blokator kalcijevih kanala t-tipa |
| WO2018141961A1 (en) | 2017-02-06 | 2018-08-09 | Idorsia Pharmaceuticals Ltd | A novel process for the synthesis of 1-aryl-1-trifluoromethylcyclopropanes |
| EP3823614A4 (en) | 2018-07-18 | 2022-03-30 | Arcus Biosciences, Inc. | SOLID FORMS OF AN AZOLOPYRIMIDINE COMPOUND |
| JP2024506858A (ja) | 2021-02-02 | 2024-02-15 | リミナル・バイオサイエンシーズ・リミテッド | Ｇｐｒ８４アンタゴニストおよびその使用 |
| KR20230153387A (ko) | 2021-02-02 | 2023-11-06 | 리미널 바이오사이언시스 리미티드 | Gpr84 길항제 및 이의 용도 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2833779A (en) * | 1956-10-29 | 1958-05-06 | American Cyanamid Co | Substituted pyrazoles |
| US5859215A (en) * | 1995-10-25 | 1999-01-12 | Wallac Oy | Biospecific binding reactants labelled with luminescent lanthanide chelates and their use |
| US6660753B2 (en) * | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| ATE307129T1 (de) * | 1999-08-19 | 2005-11-15 | Nps Pharma Inc | Heteropolycyclische verbindungen und ihre verwendung als antagonisten von metabotropen glutamatrezeptoren |
| CA2462289C (en) * | 2001-10-04 | 2010-02-23 | Nicholas D. Cosford | Heteroaryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| AU2002365892A1 (en) * | 2001-11-30 | 2003-06-17 | Merck & Co., Inc. | Metabotropic glutamate receptor-5 modulators |
| EP1458708B1 (en) * | 2001-12-18 | 2007-09-26 | Merck & Co., Inc. | Heteroaryl substituted triazole modulators of metabotropic glutamate receptor-5 |
| JP4357965B2 (ja) * | 2001-12-21 | 2009-11-04 | メルク エンド カムパニー インコーポレーテッド | メタボトロピックグルタミン酸受容体−５のヘテロアリール置換ピロールモジュレーター |
| EP1485093B1 (en) * | 2002-03-12 | 2010-11-03 | Merck Sharp & Dohme Corp. | Di-aryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| EP1613614A2 (en) * | 2003-04-03 | 2006-01-11 | Merck & Co., Inc. | Di-aryl substituted pyrazole modulators of metabotropic glutamate receptor-5 |
| JP2006522128A (ja) * | 2003-04-03 | 2006-09-28 | メルク エンド カムパニー インコーポレーテッド | 代謝調節型グルタミン酸受容体−５のモジュレーターとしての４環イミダゾール誘導体 |
| CN100537564C (zh) * | 2003-04-04 | 2009-09-09 | 麦克公司 | 代谢型谷氨酸受体-5的二芳基取代三唑调节剂 |
| EP1613265A4 (en) * | 2003-04-04 | 2007-02-14 | Merck & Co Inc | DI-ARYL-SUBSTITUTED PYRROL MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5 |
| CN1845915A (zh) * | 2003-09-02 | 2006-10-11 | 默克公司 | 作为亲代谢谷氨酸受体－5的调节剂的联吡啶胺和醚类化合物 |
| US20060189661A1 (en) * | 2003-11-03 | 2006-08-24 | Wagenen Bradford V | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| EP1715867A4 (en) | 2004-02-12 | 2009-04-15 | Merck & Co Inc | BIPYRIDYLAMIDE AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5 |
| WO2007070563A2 (en) * | 2005-12-13 | 2007-06-21 | Harkness Pharmaceuticals, Inc. | Stable solid forms of enterostatin |
-
2002
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