JPH01279872A - イミダゾール誘導体、その製法及び該化合物を含有する精神病薬 - Google Patents
イミダゾール誘導体、その製法及び該化合物を含有する精神病薬Info
- Publication number
- JPH01279872A JPH01279872A JP63313992A JP31399288A JPH01279872A JP H01279872 A JPH01279872 A JP H01279872A JP 63313992 A JP63313992 A JP 63313992A JP 31399288 A JP31399288 A JP 31399288A JP H01279872 A JPH01279872 A JP H01279872A
- Authority
- JP
- Japan
- Prior art keywords
- imidazole
- ethyl
- group
- oxadiazol
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 72
- 150000002460 imidazoles Chemical class 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 208000028017 Psychotic disease Diseases 0.000 title description 3
- 229940079593 drug Drugs 0.000 title description 3
- 239000003814 drug Substances 0.000 title description 3
- 239000002253 acid Substances 0.000 claims abstract description 21
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 150000004292 cyclic ethers Chemical group 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- -1 1-(3,4-dimethoxyphenyl)-imidazole-4-carboxylic acid ethyl ester 1-(3 , 4-dimethoxyphenyl)-4-(3-ethyl-1,2,4-oxadiazole-5- yl)-imidazole Chemical compound 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004185 ester group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical group N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 2
- BENKMEFJDPAUOV-UHFFFAOYSA-N ethyl 1-[3-(5-bromopyridin-2-yl)oxyphenyl]imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=CC=CC(OC=2N=CC(Br)=CC=2)=C1 BENKMEFJDPAUOV-UHFFFAOYSA-N 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- PEGHJBGYWJLUEA-UHFFFAOYSA-N 1-(3-hydroxyphenyl)-5-methylimidazole-4-carbonitrile Chemical compound CC1=C(C#N)N=CN1C1=CC=CC(O)=C1 PEGHJBGYWJLUEA-UHFFFAOYSA-N 0.000 claims 1
- GKXUGESIBCZKPD-UHFFFAOYSA-N 1-(3-phenylmethoxyphenyl)imidazole-4-carbonitrile Chemical compound C1=NC(C#N)=CN1C1=CC=CC(OCC=2C=CC=CC=2)=C1 GKXUGESIBCZKPD-UHFFFAOYSA-N 0.000 claims 1
- ZQWHBVORQBUKDM-UHFFFAOYSA-N 2-[4-(3-ethyl-1,2,4-oxadiazol-5-yl)imidazol-1-yl]benzene-1,3-diol Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C(=CC=CC=2O)O)=N1 ZQWHBVORQBUKDM-UHFFFAOYSA-N 0.000 claims 1
- IIQXIWRMFGIWKD-UHFFFAOYSA-N 3-[1-(3-cyclopentyloxyphenyl)-5-methylimidazol-4-yl]-5-ethyl-1,2,4-oxadiazole Chemical compound O1C(CC)=NC(C2=C(N(C=N2)C=2C=C(OC3CCCC3)C=CC=2)C)=N1 IIQXIWRMFGIWKD-UHFFFAOYSA-N 0.000 claims 1
- NEBVIIRYKOUWOI-UHFFFAOYSA-N 3-[4-(3-ethyl-1,2,4-oxadiazol-5-yl)-5-(methoxymethyl)imidazol-1-yl]phenol Chemical compound CCC1=NOC(C2=C(N(C=N2)C=2C=C(O)C=CC=2)COC)=N1 NEBVIIRYKOUWOI-UHFFFAOYSA-N 0.000 claims 1
- XYSFWTVDLCFKAC-UHFFFAOYSA-N 3-[4-(5-ethyl-1,2,4-oxadiazol-3-yl)-5-methylimidazol-1-yl]phenol Chemical compound O1C(CC)=NC(C2=C(N(C=N2)C=2C=C(O)C=CC=2)C)=N1 XYSFWTVDLCFKAC-UHFFFAOYSA-N 0.000 claims 1
- ISROYRYEUNPACE-UHFFFAOYSA-N 3-ethyl-5-[1-(2-phenylmethoxyphenyl)imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C(=CC=CC=2)OCC=2C=CC=CC=2)=N1 ISROYRYEUNPACE-UHFFFAOYSA-N 0.000 claims 1
- NFOUCXIHNXBXPM-UHFFFAOYSA-N 3-ethyl-5-[1-(3-phenoxyphenyl)imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=C(OC=3C=CC=CC=3)C=CC=2)=N1 NFOUCXIHNXBXPM-UHFFFAOYSA-N 0.000 claims 1
- QSUUNVXXUHEGPC-UHFFFAOYSA-N 3-ethyl-5-[1-(3-phenylmethoxyphenyl)imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 QSUUNVXXUHEGPC-UHFFFAOYSA-N 0.000 claims 1
- ILXILAONZCWFFZ-UHFFFAOYSA-N 3-ethyl-5-[1-(3-prop-2-enoxyphenyl)imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=C(OCC=C)C=CC=2)=N1 ILXILAONZCWFFZ-UHFFFAOYSA-N 0.000 claims 1
- UGLLSYSSARAHGX-UHFFFAOYSA-N 3-ethyl-5-[1-(3-propan-2-yloxyphenyl)imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=C(OC(C)C)C=CC=2)=N1 UGLLSYSSARAHGX-UHFFFAOYSA-N 0.000 claims 1
- MPPUIYQBQSCGOY-UHFFFAOYSA-N 3-ethyl-5-[1-(4-phenylmethoxyphenyl)imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 MPPUIYQBQSCGOY-UHFFFAOYSA-N 0.000 claims 1
- RPDLTORMCLJLEA-UHFFFAOYSA-N 3-ethyl-5-[1-[2-(2-phenylethoxy)phenyl]imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C(=CC=CC=2)OCCC=2C=CC=CC=2)=N1 RPDLTORMCLJLEA-UHFFFAOYSA-N 0.000 claims 1
- ZJZOMNLFQBMPPQ-UHFFFAOYSA-N 3-ethyl-5-[1-[3-(2-phenylethoxy)phenyl]imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=C(OCCC=3C=CC=CC=3)C=CC=2)=N1 ZJZOMNLFQBMPPQ-UHFFFAOYSA-N 0.000 claims 1
- NMWYAELNKNAWSD-UHFFFAOYSA-N 3-ethyl-5-[5-(methoxymethyl)-1-(3-methoxyphenyl)imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C2=C(N(C=N2)C=2C=C(OC)C=CC=2)COC)=N1 NMWYAELNKNAWSD-UHFFFAOYSA-N 0.000 claims 1
- MPMIZISLZJSROI-UHFFFAOYSA-N 3-ethyl-5-[5-(methoxymethyl)-1-(3-phenylmethoxyphenyl)imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C2=C(N(C=N2)C=2C=C(OCC=3C=CC=CC=3)C=CC=2)COC)=N1 MPMIZISLZJSROI-UHFFFAOYSA-N 0.000 claims 1
- YDZHIJDJMBCXNL-UHFFFAOYSA-N 3-ethyl-5-[5-(methoxymethyl)-1-[3-(4-nitrophenoxy)phenyl]imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C2=C(N(C=N2)C=2C=C(OC=3C=CC(=CC=3)[N+]([O-])=O)C=CC=2)COC)=N1 YDZHIJDJMBCXNL-UHFFFAOYSA-N 0.000 claims 1
- AAKTVHZXLIQEOS-UHFFFAOYSA-N 3-ethyl-5-[5-methyl-1-(3-phenylmethoxyphenyl)imidazol-4-yl]-1,2,4-oxadiazole Chemical compound CCC1=NOC(C2=C(N(C=N2)C=2C=C(OCC=3C=CC=CC=3)C=CC=2)C)=N1 AAKTVHZXLIQEOS-UHFFFAOYSA-N 0.000 claims 1
- UQWWUKCVDZEKSQ-UHFFFAOYSA-N 4-[3-[4-(3-ethyl-1,2,4-oxadiazol-5-yl)imidazol-1-yl]phenoxy]aniline Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=C(OC=3C=CC(N)=CC=3)C=CC=2)=N1 UQWWUKCVDZEKSQ-UHFFFAOYSA-N 0.000 claims 1
- WMIYCFKZMYQLRJ-UHFFFAOYSA-N 5-[1-(1,3-benzodioxol-5-yl)imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=C3OCOC3=CC=2)=N1 WMIYCFKZMYQLRJ-UHFFFAOYSA-N 0.000 claims 1
- LBKGBASHFSDLKP-UHFFFAOYSA-N 5-[1-(2-chloro-5-methoxyphenyl)imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C(=CC=C(OC)C=2)Cl)=N1 LBKGBASHFSDLKP-UHFFFAOYSA-N 0.000 claims 1
- QSBSJTBWFDBLMP-UHFFFAOYSA-N 5-[1-(3-cyclopentyloxyphenyl)-5-(methoxymethyl)imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C2=C(N(C=N2)C=2C=C(OC3CCCC3)C=CC=2)COC)=N1 QSBSJTBWFDBLMP-UHFFFAOYSA-N 0.000 claims 1
- IBAKJBJNJQKUFZ-UHFFFAOYSA-N 5-[1-(3-ethoxyphenyl)imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCOC1=CC=CC(N2C=C(N=C2)C=2ON=C(CC)N=2)=C1 IBAKJBJNJQKUFZ-UHFFFAOYSA-N 0.000 claims 1
- RSALVMFKYUHZAX-UHFFFAOYSA-N 5-[1-(5-chloro-2-methoxyphenyl)imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C(=CC=C(Cl)C=2)OC)=N1 RSALVMFKYUHZAX-UHFFFAOYSA-N 0.000 claims 1
- NSXSTZMVNNWKPG-UHFFFAOYSA-N 5-[1-(5-chloro-2-phenylmethoxyphenyl)imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C(=CC=C(Cl)C=2)OCC=2C=CC=CC=2)=N1 NSXSTZMVNNWKPG-UHFFFAOYSA-N 0.000 claims 1
- IEPXQNDUDGMPQR-UHFFFAOYSA-N 5-[1-[2,6-bis(phenylmethoxy)phenyl]imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C(=CC=CC=2OCC=2C=CC=CC=2)OCC=2C=CC=CC=2)=N1 IEPXQNDUDGMPQR-UHFFFAOYSA-N 0.000 claims 1
- QOVHXHPFAORTCV-UHFFFAOYSA-N 5-[1-[2-[(4-chlorophenyl)methoxy]phenyl]imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C(=CC=CC=2)OCC=2C=CC(Cl)=CC=2)=N1 QOVHXHPFAORTCV-UHFFFAOYSA-N 0.000 claims 1
- PZIHCULCDPZVOR-UHFFFAOYSA-N 5-[1-[3-(4-chlorophenoxy)phenyl]-5-(methoxymethyl)imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C2=C(N(C=N2)C=2C=C(OC=3C=CC(Cl)=CC=3)C=CC=2)COC)=N1 PZIHCULCDPZVOR-UHFFFAOYSA-N 0.000 claims 1
- ORAMBFYYNAFDNH-UHFFFAOYSA-N 5-[1-[3-(4-chlorophenoxy)phenyl]imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=C(OC=3C=CC(Cl)=CC=3)C=CC=2)=N1 ORAMBFYYNAFDNH-UHFFFAOYSA-N 0.000 claims 1
- ULHMAYUYGOKMHE-UHFFFAOYSA-N 5-[1-[3-[(4-chlorophenyl)methoxy]phenyl]imidazol-4-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=C(OCC=3C=CC(Cl)=CC=3)C=CC=2)=N1 ULHMAYUYGOKMHE-UHFFFAOYSA-N 0.000 claims 1
- KUEKYXIWRSDELZ-UHFFFAOYSA-N 5-[2-[3-(5-bromopyridin-2-yl)oxyphenyl]-1H-imidazol-5-yl]-3-ethyl-1,2,4-oxadiazole Chemical compound BrC=1C=CC(=NC1)OC=1C=C(C=CC1)C=1NC=C(N1)C1=NC(=NO1)CC KUEKYXIWRSDELZ-UHFFFAOYSA-N 0.000 claims 1
- UZUNQNYCGUATQO-UHFFFAOYSA-N 5-ethyl-3-[5-methyl-1-(3-phenoxyphenyl)imidazol-4-yl]-1,2,4-oxadiazole Chemical compound O1C(CC)=NC(C2=C(N(C=N2)C=2C=C(OC=3C=CC=CC=3)C=CC=2)C)=N1 UZUNQNYCGUATQO-UHFFFAOYSA-N 0.000 claims 1
- MICMDBVRKOUTNH-UHFFFAOYSA-N 5-methyl-1-(3-phenoxyphenyl)imidazole-4-carbonitrile Chemical compound CC1=C(C#N)N=CN1C1=CC=CC(OC=2C=CC=CC=2)=C1 MICMDBVRKOUTNH-UHFFFAOYSA-N 0.000 claims 1
- 206010011703 Cyanosis Diseases 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- IGYRDNPJDPUHOA-UHFFFAOYSA-N ethyl 1-(2,6-dihydroxyphenyl)imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=C(O)C=CC=C1O IGYRDNPJDPUHOA-UHFFFAOYSA-N 0.000 claims 1
- ZQJOQQXBWIHMBP-UHFFFAOYSA-N ethyl 1-(3-cyclopentyloxyphenyl)imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=CC=CC(OC2CCCC2)=C1 ZQJOQQXBWIHMBP-UHFFFAOYSA-N 0.000 claims 1
- CSVHDBWJCYXUHS-UHFFFAOYSA-N ethyl 1-(3-hydroxyphenyl)imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=CC=CC(O)=C1 CSVHDBWJCYXUHS-UHFFFAOYSA-N 0.000 claims 1
- NCDOYNBLKBYGFU-UHFFFAOYSA-N ethyl 1-(3-methoxyphenyl)imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=CC=CC(OC)=C1 NCDOYNBLKBYGFU-UHFFFAOYSA-N 0.000 claims 1
- XNAVRNCANZAWGA-UHFFFAOYSA-N ethyl 1-(3-prop-2-enoxyphenyl)imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=CC=CC(OCC=C)=C1 XNAVRNCANZAWGA-UHFFFAOYSA-N 0.000 claims 1
- FKHCEBWPOLBNGR-UHFFFAOYSA-N ethyl 1-(3-propan-2-yloxyphenyl)imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=CC=CC(OC(C)C)=C1 FKHCEBWPOLBNGR-UHFFFAOYSA-N 0.000 claims 1
- FAFDNWLNRBPIQA-UHFFFAOYSA-N ethyl 1-(4-methoxyphenyl)imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=CC=C(OC)C=C1 FAFDNWLNRBPIQA-UHFFFAOYSA-N 0.000 claims 1
- HHNMIWKJVPSQNR-UHFFFAOYSA-N ethyl 1-(4-phenoxyphenyl)imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C(C=C1)=CC=C1OC1=CC=CC=C1 HHNMIWKJVPSQNR-UHFFFAOYSA-N 0.000 claims 1
- PHJSCMQOKSLNBQ-UHFFFAOYSA-N ethyl 1-[2,6-bis(phenylmethoxy)phenyl]imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C(C(=CC=C1)OCC=2C=CC=CC=2)=C1OCC1=CC=CC=C1 PHJSCMQOKSLNBQ-UHFFFAOYSA-N 0.000 claims 1
- FRRWXLAWTGXABV-UHFFFAOYSA-N ethyl 1-[3-(4-aminophenoxy)phenyl]imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=CC=CC(OC=2C=CC(N)=CC=2)=C1 FRRWXLAWTGXABV-UHFFFAOYSA-N 0.000 claims 1
- HOAWFNHMEUKPSM-UHFFFAOYSA-N ethyl 1-[3-(4-chlorophenoxy)phenyl]imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=CC=CC(OC=2C=CC(Cl)=CC=2)=C1 HOAWFNHMEUKPSM-UHFFFAOYSA-N 0.000 claims 1
- ZHARLMDZESJMOY-UHFFFAOYSA-N ethyl 1-[3-(4-nitrophenoxy)phenyl]imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OCC)=CN1C1=CC=CC(OC=2C=CC(=CC=2)[N+]([O-])=O)=C1 ZHARLMDZESJMOY-UHFFFAOYSA-N 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- HZZCRKFWXILUJL-UHFFFAOYSA-N propan-2-yl 1-(3-cyclopentyloxyphenyl)imidazole-4-carboxylate Chemical compound C1=NC(C(=O)OC(C)C)=CN1C1=CC=CC(OC2CCCC2)=C1 HZZCRKFWXILUJL-UHFFFAOYSA-N 0.000 claims 1
- LTIXFXYUUCETLX-UHFFFAOYSA-N propan-2-yl 1-(3-methoxyphenyl)imidazole-4-carboxylate Chemical compound COC1=CC=CC(N2C=C(N=C2)C(=O)OC(C)C)=C1 LTIXFXYUUCETLX-UHFFFAOYSA-N 0.000 claims 1
- 239000003196 psychodysleptic agent Substances 0.000 claims 1
- 150000003567 thiocyanates Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 230000002936 tranquilizing effect Effects 0.000 abstract description 3
- KCKWJZUKMXUCBK-UHFFFAOYSA-N 3-[4-(3-ethyl-1,2,4-oxadiazol-5-yl)imidazol-1-yl]phenol Chemical compound CCC1=NOC(C=2N=CN(C=2)C=2C=C(O)C=CC=2)=N1 KCKWJZUKMXUCBK-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000000164 antipsychotic agent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 229940125725 tranquilizer Drugs 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 92
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 238000002844 melting Methods 0.000 description 35
- 230000008018 melting Effects 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000010626 work up procedure Methods 0.000 description 15
- 238000004587 chromatography analysis Methods 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
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- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
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- 238000007045 Balz-Schiemann reaction Methods 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DXDNEDKSDWKHCO-UHFFFAOYSA-N CN(C)C=O.c1c[nH]cn1 Chemical compound CN(C)C=O.c1c[nH]cn1 DXDNEDKSDWKHCO-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
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- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical group CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
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- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 150000007928 imidazolide derivatives Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- OINDCHZMTRULBK-UHFFFAOYSA-N n'-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-n,n-dimethylmethanimidamide Chemical compound CCC1=NOC(CN=CN(C)C)=N1 OINDCHZMTRULBK-UHFFFAOYSA-N 0.000 description 1
- GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical compound C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3742716.4 | 1987-12-14 | ||
| DE19873742716 DE3742716A1 (de) | 1987-12-14 | 1987-12-14 | Imidazolderivate ii |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01279872A true JPH01279872A (ja) | 1989-11-10 |
Family
ID=6342780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63313992A Pending JPH01279872A (ja) | 1987-12-14 | 1988-12-14 | イミダゾール誘導体、その製法及び該化合物を含有する精神病薬 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5179111A (enExample) |
| EP (1) | EP0323799B1 (enExample) |
| JP (1) | JPH01279872A (enExample) |
| AT (1) | ATE82285T1 (enExample) |
| CA (1) | CA1330341C (enExample) |
| DE (2) | DE3742716A1 (enExample) |
| ES (1) | ES2052768T3 (enExample) |
| GR (1) | GR3006948T3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999038829A1 (en) * | 1998-01-28 | 1999-08-05 | Shionogi & Co., Ltd. | Novel tricyclic compound |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3824658A1 (de) * | 1988-07-15 | 1990-01-18 | Schering Ag | N-hetaryl-imidazolderivate |
| AU6157190A (en) * | 1989-08-19 | 1991-04-03 | Boehringer Ingelheim International Gmbh | Substituted n-heterocycles, their preparation and their use |
| DE4112451A1 (de) * | 1991-04-12 | 1992-10-15 | Schering Ag | Isoxazolylimidazolderivate, verfahren zu deren herstellung und deren verwendung in arzneimitteln |
| US5502072A (en) * | 1993-11-26 | 1996-03-26 | Pfizer Inc. | Substituted oxindoles |
| DE4432391A1 (de) * | 1994-09-02 | 1996-03-07 | Schering Ag | Neues Verfahren zur Herstellung von I-Phenyl-imidazolderivaten |
| WO2007042545A1 (en) * | 2005-10-14 | 2007-04-19 | Neurosearch A/S | Imidazole derivatives and their use for modulating the gaba-a receptor complex |
| EP1940829A2 (en) * | 2005-10-14 | 2008-07-09 | NeuroSearch A/S | Imidazole derivatives and their use for modulating the gabaa receptor complex |
| EP1940801A2 (en) * | 2005-10-14 | 2008-07-09 | NeuroSearch A/S | Imidazole derivatives and their use for modulating the gaba-a receptor complex |
| AU2015319834A1 (en) | 2014-09-25 | 2017-04-20 | University Of Notre Dame Du Lac | Non-beta lactam antibiotics |
| WO2018049404A1 (en) | 2016-09-12 | 2018-03-15 | University Of Notre Dame Du Lac | Compounds for the treatment of clostridium difficile infection |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3444918A1 (de) * | 1984-12-08 | 1986-06-12 | Hoechst Ag, 6230 Frankfurt | 1-phenyl-imidazol-5-carbonsaeure-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren |
| US4771051A (en) * | 1985-05-17 | 1988-09-13 | A/S Ferrosan | 3-substituted-4,5-dihydro-5-oxo imidazoquinazolines, their preparation, and their use in treating benzodiazepin receptor-related ailments |
| US4852132A (en) * | 1985-08-30 | 1989-07-25 | Yokogawa Medical Systems | Method of collecting data for x-ray tomograph |
| DE3627155A1 (de) * | 1986-08-11 | 1988-02-18 | Schering Ag | Imidazol-derivate |
| EP0284277A1 (en) * | 1987-03-21 | 1988-09-28 | AgrEvo UK Limited | Cyanoimidazole fungicides |
-
1987
- 1987-12-14 DE DE19873742716 patent/DE3742716A1/de not_active Withdrawn
-
1988
- 1988-12-13 CA CA000585771A patent/CA1330341C/en not_active Expired - Fee Related
- 1988-12-14 AT AT88730278T patent/ATE82285T1/de not_active IP Right Cessation
- 1988-12-14 ES ES88730278T patent/ES2052768T3/es not_active Expired - Lifetime
- 1988-12-14 JP JP63313992A patent/JPH01279872A/ja active Pending
- 1988-12-14 US US07/284,223 patent/US5179111A/en not_active Expired - Fee Related
- 1988-12-14 EP EP88730278A patent/EP0323799B1/de not_active Expired - Lifetime
- 1988-12-14 DE DE8888730278T patent/DE3875945D1/de not_active Expired - Lifetime
-
1993
- 1993-01-29 GR GR920402866T patent/GR3006948T3/el unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999038829A1 (en) * | 1998-01-28 | 1999-08-05 | Shionogi & Co., Ltd. | Novel tricyclic compound |
| US6562817B1 (en) | 1998-01-28 | 2003-05-13 | Shionogi & Co., Ltd. | Tricyclic compound |
| JP3929700B2 (ja) * | 1998-01-28 | 2007-06-13 | 塩野義製薬株式会社 | 新規三環式化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3875945D1 (de) | 1992-12-17 |
| DE3742716A1 (de) | 1989-06-22 |
| ATE82285T1 (de) | 1992-11-15 |
| EP0323799B1 (de) | 1992-11-11 |
| CA1330341C (en) | 1994-06-21 |
| US5179111A (en) | 1993-01-12 |
| EP0323799A1 (de) | 1989-07-12 |
| GR3006948T3 (enExample) | 1993-06-30 |
| ES2052768T3 (es) | 1994-07-16 |
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