JP2009545542A5 - - Google Patents
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- JP2009545542A5 JP2009545542A5 JP2009522134A JP2009522134A JP2009545542A5 JP 2009545542 A5 JP2009545542 A5 JP 2009545542A5 JP 2009522134 A JP2009522134 A JP 2009522134A JP 2009522134 A JP2009522134 A JP 2009522134A JP 2009545542 A5 JP2009545542 A5 JP 2009545542A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- alkyl
- het
- aryl
- defined above
- 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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- -1 benzoimidazolyl Chemical group 0.000 claims 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 4
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 4
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 3
- HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical compound C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 claims 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
- HYLJXJSMGIOVIK-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1,5-benzoxazepine Chemical compound O1CCCNC2=CC=CC=C21 HYLJXJSMGIOVIK-UHFFFAOYSA-N 0.000 claims 2
- MZBVNYACSSGXID-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1-benzazepine Chemical compound N1CCCCC2=CC=CC=C21 MZBVNYACSSGXID-UHFFFAOYSA-N 0.000 claims 2
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims 2
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- KVRZARWOKBNZMM-UHFFFAOYSA-N 1,3-dihydro-2-benzothiophene Chemical compound C1=CC=C2CSCC2=C1 KVRZARWOKBNZMM-UHFFFAOYSA-N 0.000 claims 1
- XBEBEBTVWAHHLP-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)-2-(3-imino-1-phenylimidazo[1,5-a]pyridin-2-yl)ethanone Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)CN2C(N3C=CC=CC3=C2C=2C=CC=CC=2)=N)=C1 XBEBEBTVWAHHLP-UHFFFAOYSA-N 0.000 claims 1
- FTECHFRDLMTBMH-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)-2-(3-imino-8-methylimidazo[1,5-a]pyridin-2-yl)ethanone Chemical compound CC1=CC=CN(C2=N)C1=CN2CC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FTECHFRDLMTBMH-UHFFFAOYSA-N 0.000 claims 1
- UURRQTQVWUTBIK-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)-2-(3-iminoimidazo[1,5-a]pyridin-2-yl)ethanone Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)CN2C(N3C=CC=CC3=C2)=N)=C1 UURRQTQVWUTBIK-UHFFFAOYSA-N 0.000 claims 1
- DSWSVIIIXZLNBD-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)-2-[3-imino-7-(trifluoromethyl)imidazo[1,5-a]pyridin-2-yl]ethanone Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)CN2C(N3C=CC(=CC3=C2)C(F)(F)F)=N)=C1 DSWSVIIIXZLNBD-UHFFFAOYSA-N 0.000 claims 1
- UVGUQWGMZQPHPL-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-8-methylimidazo[1,5-a]pyridin-2-yl)ethanone Chemical compound C1=C(C(=O)CN2C(N3C=CC=C(C)C3=C2)=N)C=C(C(C)(C)C)C(OC)=C1N1CCOCC1 UVGUQWGMZQPHPL-UHFFFAOYSA-N 0.000 claims 1
- BJEZKCFCIMRPHH-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-iminoimidazo[1,5-a]pyridin-2-yl)ethanone Chemical compound C1=C(C(=O)CN2C(N3C=CC=CC3=C2)=N)C=C(C(C)(C)C)C(OC)=C1N1CCOCC1 BJEZKCFCIMRPHH-UHFFFAOYSA-N 0.000 claims 1
- UUUJCSVRMDBVHA-UHFFFAOYSA-N 1-[3-(dimethylamino)-5-(pentafluoro-$l^{6}-sulfanyl)phenyl]-2-(3-iminoimidazo[1,5-a]pyridin-2-yl)ethanone Chemical compound FS(F)(F)(F)(F)C1=CC(N(C)C)=CC(C(=O)CN2C(N3C=CC=CC3=C2)=N)=C1 UUUJCSVRMDBVHA-UHFFFAOYSA-N 0.000 claims 1
- WGZLVYLRRKENQU-UHFFFAOYSA-N 1-[3-bromo-4-methoxy-5-(trifluoromethyl)phenyl]-2-(3-iminoimidazo[1,5-a]pyridin-2-yl)ethanone Chemical compound C1=C(C(F)(F)F)C(OC)=C(Br)C=C1C(=O)CN1C(=N)N2C=CC=CC2=C1 WGZLVYLRRKENQU-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- WOHLSTOWRAOMSG-UHFFFAOYSA-N 2,3-dihydro-1,3-benzothiazole Chemical compound C1=CC=C2SCNC2=C1 WOHLSTOWRAOMSG-UHFFFAOYSA-N 0.000 claims 1
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical compound C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 claims 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
- YKWSNLLNDUWKPY-UHFFFAOYSA-N 2-(1-cyclopropyl-3-iminoimidazo[1,5-a]pyridin-2-yl)-1-(3,5-ditert-butyl-4-hydroxyphenyl)ethanone Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(=O)CN2C(N3C=CC=CC3=C2C2CC2)=N)=C1 YKWSNLLNDUWKPY-UHFFFAOYSA-N 0.000 claims 1
- GSPATNBIDGBJLW-UHFFFAOYSA-N 2-(3-iminoimidazo[1,5-a]pyridin-2-yl)-1-[3-(pentafluoro-$l^{6}-sulfanyl)phenyl]ethanone Chemical compound FS(F)(F)(F)(F)C1=CC=CC(C(=O)CN2C(N3C=CC=CC3=C2)=N)=C1 GSPATNBIDGBJLW-UHFFFAOYSA-N 0.000 claims 1
- FBXSGOWPSPFARF-UHFFFAOYSA-N 2-(3-iminoimidazo[1,5-a]pyridin-2-yl)-1-[4-methoxy-3-morpholin-4-yl-5-(trifluoromethyl)phenyl]ethanone Chemical compound C1=C(C(=O)CN2C(N3C=CC=CC3=C2)=N)C=C(C(F)(F)F)C(OC)=C1N1CCOCC1 FBXSGOWPSPFARF-UHFFFAOYSA-N 0.000 claims 1
- QOOQGHXHGAGHKB-UHFFFAOYSA-N 2-[2-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-oxoethyl]-7-chloro-3-imino-n-methylimidazo[1,5-a]pyridine-6-carboxamide Chemical compound C1=C(Cl)C(C(=O)NC)=CN(C2=N)C1=CN2CC(=O)C(C=C(C=1OC)C(C)(C)C)=CC=1N1CCOCC1 QOOQGHXHGAGHKB-UHFFFAOYSA-N 0.000 claims 1
- HQUZGQRPJHEZNC-UHFFFAOYSA-N 2-[2-(8-tert-butyl-4-methyl-2,3-dihydro-1,4-benzoxazin-6-yl)-2-oxoethyl]-7-ethoxy-3-imino-n-methylimidazo[1,5-a]pyridine-6-carboxamide Chemical compound CN1CCOC(C(=C2)C(C)(C)C)=C1C=C2C(=O)CN1C=C2C=C(OCC)C(C(=O)NC)=CN2C1=N HQUZGQRPJHEZNC-UHFFFAOYSA-N 0.000 claims 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
- ADEKJVNFIQUGRR-UHFFFAOYSA-N 4h-pyridin-3-one Chemical compound O=C1CC=CN=C1 ADEKJVNFIQUGRR-UHFFFAOYSA-N 0.000 claims 1
- MUOUEXCMSFEALV-UHFFFAOYSA-N 7-oxabicyclo[4.2.0]octa-1,3,5-triene Chemical compound C1=CC=C2COC2=C1 MUOUEXCMSFEALV-UHFFFAOYSA-N 0.000 claims 1
- URFYYUQDLKBFGM-UHFFFAOYSA-N C1N=CN2C1=CC=CC2=O.FC(C(=O)O)(F)F Chemical compound C1N=CN2C1=CC=CC2=O.FC(C(=O)O)(F)F URFYYUQDLKBFGM-UHFFFAOYSA-N 0.000 claims 1
- ZPMUGXNRYSQPCK-UHFFFAOYSA-N CNC(=O)C=1C=CC=2N(C1)C=NC2.FC(C(=O)O)(F)F Chemical compound CNC(=O)C=1C=CC=2N(C1)C=NC2.FC(C(=O)O)(F)F ZPMUGXNRYSQPCK-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- VFHWCZMTMRVBAN-UHFFFAOYSA-N acetaldehyde hydrobromide Chemical compound Br.CC=O VFHWCZMTMRVBAN-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- 125000002785 azepinyl group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 1
- 239000012964 benzotriazole Substances 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000004623 carbolinyl group Chemical group 0.000 claims 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 125000003838 furazanyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 claims 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
- 125000005438 isoindazolyl group Chemical group 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- FURFAZDJPIDHDQ-UHFFFAOYSA-N methyl 2-[2-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-oxoethyl]-3-iminoimidazo[1,5-a]pyridine-6-carboxylate Chemical compound N=C1N2C=C(C(=O)OC)C=CC2=CN1CC(=O)C(C=C(C=1OC)C(C)(C)C)=CC=1N1CCOCC1 FURFAZDJPIDHDQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 1
- 125000004932 phenoxathinyl group Chemical group 0.000 claims 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims 1
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 claims 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- YYMWVZQRBNARFZ-UHFFFAOYSA-M sodium;2-[2,3-bis(sulfanyl)propoxy]ethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCOCC(S)CS YYMWVZQRBNARFZ-UHFFFAOYSA-M 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 125000002769 thiazolinyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| DE102006036023.0 | 2006-08-02 | ||
| DE102006036023A DE102006036023A1 (de) | 2006-08-02 | 2006-08-02 | Imino-imidazo-pyridinderivate mit antithrombotischer Aktivität |
| PCT/EP2007/006360 WO2008014888A2 (de) | 2006-08-02 | 2007-07-18 | Imino-imidazo-pyridinderivate mit antithrombotischer aktivität |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009545542A JP2009545542A (ja) | 2009-12-24 |
| JP2009545542A5 true JP2009545542A5 (https=) | 2010-09-02 |
| JP5149897B2 JP5149897B2 (ja) | 2013-02-20 |
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| EP (1) | EP2054412B1 (https=) |
| JP (1) | JP5149897B2 (https=) |
| KR (1) | KR20090129981A (https=) |
| CN (1) | CN101495478B (https=) |
| AR (1) | AR062158A1 (https=) |
| AT (1) | ATE450537T1 (https=) |
| AU (1) | AU2007280780B2 (https=) |
| BR (1) | BRPI0714599A2 (https=) |
| CA (1) | CA2663332C (https=) |
| CL (1) | CL2007002240A1 (https=) |
| DE (2) | DE102006036023A1 (https=) |
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| ES (1) | ES2336044T3 (https=) |
| IL (1) | IL196789A (https=) |
| MX (1) | MX2009000408A (https=) |
| MY (1) | MY148611A (https=) |
| NO (1) | NO20090741L (https=) |
| PE (1) | PE20080687A1 (https=) |
| PT (1) | PT2054412E (https=) |
| TW (1) | TWI400240B (https=) |
| WO (1) | WO2008014888A2 (https=) |
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| WO2009097970A1 (de) * | 2008-02-05 | 2009-08-13 | Sanofi-Aventis | Triazolopyridazine als par1-inhibitoren, ihre herstellung und verwendung als arzneimittel |
| CA2903306A1 (en) | 2013-03-15 | 2014-09-18 | Fundacio Institut De Recerca Biomedica (Irb Barcelona) | Method for the diagnosis, prognosis and treatment of metastatic cancer |
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| JPS5124517B1 (https=) | 1971-03-15 | 1976-07-24 | ||
| DE2221796A1 (de) | 1972-05-04 | 1973-11-15 | Kraemer Kg Wilhelm | Batteriebehaelter fuer stabbatterien |
| JPS60161986A (ja) * | 1983-12-24 | 1985-08-23 | Nippon Soda Co Ltd | イミダゾ（１，５−ａ）ピリジン−３−オン誘導体及びその製造方法 |
| US6063847A (en) | 1997-11-25 | 2000-05-16 | Schering Corporation | Thrombin receptor antagonists |
| US7488742B2 (en) | 2000-06-15 | 2009-02-10 | Schering Corporation | Thrombin receptor antagonists |
| US7304078B2 (en) | 2002-04-16 | 2007-12-04 | Schering Corporation | Thrombin receptor antagonists |
| NZ528820A (en) * | 2001-04-19 | 2007-01-26 | Eisai Co Ltd | 2-iminopyrrolidine derivatives |
| EP2444393A1 (en) | 2003-02-19 | 2012-04-25 | Eisai R&D Management Co., Ltd. | Methods for producing cyclic benzamidine derivatives |
| DE10353205A1 (de) | 2003-11-13 | 2005-06-16 | Aventis Pharma Deutschland Gmbh | Ortho-substituierte Pentafluorsulfuranyl-Benzole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als wertvolle Synthese-Zwischenstufen |
| US7317124B2 (en) | 2003-11-13 | 2008-01-08 | Sanofi-Aventis Deutschland Gmbh | Ortho-substituted pentafluorosulfanylbenzenes, process for their preparation and their use as valuable synthetic intermediates |
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2006
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2007
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- 2007-07-18 MY MYPI20090170A patent/MY148611A/en unknown
- 2007-07-18 KR KR1020097002137A patent/KR20090129981A/ko not_active Abandoned
- 2007-07-18 JP JP2009522134A patent/JP5149897B2/ja not_active Expired - Fee Related
- 2007-07-18 WO PCT/EP2007/006360 patent/WO2008014888A2/de not_active Ceased
- 2007-07-18 CN CN2007800279925A patent/CN101495478B/zh not_active Expired - Fee Related
- 2007-07-18 AU AU2007280780A patent/AU2007280780B2/en not_active Ceased
- 2007-07-18 DK DK07765222.0T patent/DK2054412T3/da active
- 2007-07-18 BR BRPI0714599-3A patent/BRPI0714599A2/pt not_active IP Right Cessation
- 2007-07-18 CA CA2663332A patent/CA2663332C/en not_active Expired - Fee Related
- 2007-07-18 EP EP07765222A patent/EP2054412B1/de not_active Not-in-force
- 2007-07-18 DE DE502007002219T patent/DE502007002219D1/de active Active
- 2007-07-18 AT AT07765222T patent/ATE450537T1/de active
- 2007-07-18 MX MX2009000408A patent/MX2009000408A/es active IP Right Grant
- 2007-07-18 PT PT07765222T patent/PT2054412E/pt unknown
- 2007-07-31 AR ARP070103373A patent/AR062158A1/es not_active Application Discontinuation
- 2007-07-31 TW TW096127870A patent/TWI400240B/zh not_active IP Right Cessation
- 2007-07-31 DO DO2007000120A patent/DOP2007000120A/es unknown
- 2007-07-31 PE PE2007000991A patent/PE20080687A1/es not_active Application Discontinuation
- 2007-08-01 CL CL200702240A patent/CL2007002240A1/es unknown
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2009
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- 2009-02-02 US US12/364,124 patent/US7863269B2/en not_active Expired - Fee Related
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