DD215542A5 - Verfahren zur herstellung von 4-cyano-pyridazinen - Google Patents
Verfahren zur herstellung von 4-cyano-pyridazinenInfo
- Publication number
- DD215542A5 DD215542A5 DD84259679A DD25967984A DD215542A5 DD 215542 A5 DD215542 A5 DD 215542A5 DD 84259679 A DD84259679 A DD 84259679A DD 25967984 A DD25967984 A DD 25967984A DD 215542 A5 DD215542 A5 DD 215542A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- formula
- carbon atoms
- cyano
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 3
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 3
- QXOXHGUPISQLPW-UHFFFAOYSA-N pyridazine-4-carbonitrile Chemical class N#CC1=CC=NN=C1 QXOXHGUPISQLPW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- -1 1,2-propylene group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 241000251730 Chondrichthyes Species 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000002690 malonic acid derivatives Chemical class 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract description 8
- 150000004892 pyridazines Chemical class 0.000 abstract description 8
- 230000000506 psychotropic effect Effects 0.000 abstract description 7
- GAQMHKPMJLFJPC-UHFFFAOYSA-N 3-chloropyridazine-4-carbonitrile Chemical compound ClC1=NN=CC=C1C#N GAQMHKPMJLFJPC-UHFFFAOYSA-N 0.000 abstract description 3
- IIAVVOGGKSJORS-UHFFFAOYSA-N ethyl 6-oxo-1h-pyridazine-5-carboxylate Chemical class CCOC(=O)C1=CC=NNC1=O IIAVVOGGKSJORS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 206010015995 Eyelid ptosis Diseases 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000007912 intraperitoneal administration Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 201000003004 ptosis Diseases 0.000 description 7
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 6
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000006399 behavior Effects 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 6
- 229960003147 reserpine Drugs 0.000 description 6
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- LDMWSLGGVTVJPG-UHFFFAOYSA-N minaprine Chemical group CC1=CC(C=2C=CC=CC=2)=NN=C1NCCN1CCOCC1 LDMWSLGGVTVJPG-UHFFFAOYSA-N 0.000 description 4
- 229960004758 minaprine Drugs 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000000926 neurological effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- VNQGFTBVMCNTRK-UHFFFAOYSA-N 3-(2-morpholin-4-ylethylamino)-6-naphthalen-1-ylpyridazine-4-carbonitrile;dihydrochloride Chemical compound Cl.Cl.N#CC1=CC(C=2C3=CC=CC=C3C=CC=2)=NN=C1NCCN1CCOCC1 VNQGFTBVMCNTRK-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 208000025966 Neurological disease Diseases 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- KRNDIPHOJLIHRI-UHFFFAOYSA-N bazinaprine Chemical compound N#CC1=CC(C=2C=CC=CC=2)=NN=C1NCCN1CCOCC1 KRNDIPHOJLIHRI-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- QPHIGPYPWKZZHV-UHFFFAOYSA-N 1,3-dichloro-1,3-bis(3,4-dihydroxyphenyl)propan-2-one Chemical compound Oc1ccc(cc1O)C(Cl)C(=O)C(Cl)c1ccc(O)c(O)c1 QPHIGPYPWKZZHV-UHFFFAOYSA-N 0.000 description 1
- BOFZOFCSIFMCEB-UHFFFAOYSA-N 1-(2-bromophenyl)-2-phenylethanone Chemical compound BrC1=CC=CC=C1C(=O)CC1=CC=CC=C1 BOFZOFCSIFMCEB-UHFFFAOYSA-N 0.000 description 1
- LLZQFAXTCYDVTR-UHFFFAOYSA-N 2-chloro-1-(1h-indol-3-yl)ethanone Chemical compound C1=CC=C2C(C(=O)CCl)=CNC2=C1 LLZQFAXTCYDVTR-UHFFFAOYSA-N 0.000 description 1
- VYWPPRLJNVHPEU-UHFFFAOYSA-N 2-chloro-1-(2,4-dichlorophenyl)ethanone Chemical compound ClCC(=O)C1=CC=C(Cl)C=C1Cl VYWPPRLJNVHPEU-UHFFFAOYSA-N 0.000 description 1
- SOGLGKRIVMZMSK-UHFFFAOYSA-N 2-chloro-1-(2-chlorophenyl)ethanone Chemical compound ClCC(=O)C1=CC=CC=C1Cl SOGLGKRIVMZMSK-UHFFFAOYSA-N 0.000 description 1
- QBUAMGNEUKWLRO-UHFFFAOYSA-N 2-chloro-1-(2-methylphenyl)ethanone Chemical compound CC1=CC=CC=C1C(=O)CCl QBUAMGNEUKWLRO-UHFFFAOYSA-N 0.000 description 1
- BYTZWANJVUAPNO-UHFFFAOYSA-N 2-chloro-1-(3,4-dichlorophenyl)ethanone Chemical compound ClCC(=O)C1=CC=C(Cl)C(Cl)=C1 BYTZWANJVUAPNO-UHFFFAOYSA-N 0.000 description 1
- AVUVSYIYUADCKE-UHFFFAOYSA-N 2-chloro-1-(3-chlorophenyl)ethanone Chemical compound ClCC(=O)C1=CC=CC(Cl)=C1 AVUVSYIYUADCKE-UHFFFAOYSA-N 0.000 description 1
- NEONXKZDDPNEQP-UHFFFAOYSA-N 2-chloro-1-(3-methylphenyl)ethanone Chemical compound CC1=CC=CC(C(=O)CCl)=C1 NEONXKZDDPNEQP-UHFFFAOYSA-N 0.000 description 1
- PPPIAEPDQPCIIM-UHFFFAOYSA-N 2-chloro-1-(4-hydroxyphenyl)ethanone Chemical compound OC1=CC=C(C(=O)CCl)C=C1 PPPIAEPDQPCIIM-UHFFFAOYSA-N 0.000 description 1
- MCRINSAETDOKDE-UHFFFAOYSA-N 2-chloro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CCl)C=C1 MCRINSAETDOKDE-UHFFFAOYSA-N 0.000 description 1
- AXIVKGQGCMDXMM-UHFFFAOYSA-N 2-chloro-1-(4-methylsulfonylphenyl)ethanone Chemical compound CS(=O)(=O)C1=CC=C(C(=O)CCl)C=C1 AXIVKGQGCMDXMM-UHFFFAOYSA-N 0.000 description 1
- YKLMHYUFNDAZAG-UHFFFAOYSA-N 2-chloro-1-(4-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=C(C(=O)CCl)C=C1 YKLMHYUFNDAZAG-UHFFFAOYSA-N 0.000 description 1
- CPEDVBNSZUDGFO-UHFFFAOYSA-N 2-chloro-1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)CCl)=C1 CPEDVBNSZUDGFO-UHFFFAOYSA-N 0.000 description 1
- VBXNXBARORLRRI-UHFFFAOYSA-N 2-chloro-1-[4-(trifluoromethyl)phenyl]ethanone Chemical compound FC(F)(F)C1=CC=C(C(=O)CCl)C=C1 VBXNXBARORLRRI-UHFFFAOYSA-N 0.000 description 1
- XQRGPXLSPCQVBC-UHFFFAOYSA-N 2-chloro-1-cyclohexylethanone Chemical compound ClCC(=O)C1CCCCC1 XQRGPXLSPCQVBC-UHFFFAOYSA-N 0.000 description 1
- LZFSTAOZPAMORU-UHFFFAOYSA-N 2-chloro-1-cyclooctylethanone Chemical compound ClCC(=O)C1CCCCCCC1 LZFSTAOZPAMORU-UHFFFAOYSA-N 0.000 description 1
- ZXWAHROJUXWVCU-UHFFFAOYSA-N 2-chloro-1-cyclopropylethanone Chemical compound ClCC(=O)C1CC1 ZXWAHROJUXWVCU-UHFFFAOYSA-N 0.000 description 1
- NYJAUILLKSDBMH-UHFFFAOYSA-N 2-chloro-1-naphthalen-2-ylethanone Chemical compound C1=CC=CC2=CC(C(=O)CCl)=CC=C21 NYJAUILLKSDBMH-UHFFFAOYSA-N 0.000 description 1
- KHOWLHQEABZKNA-UHFFFAOYSA-N 2-chloro-1-thiophen-2-ylethanone Chemical compound ClCC(=O)C1=CC=CS1 KHOWLHQEABZKNA-UHFFFAOYSA-N 0.000 description 1
- DUVRDRIDUGKOHS-UHFFFAOYSA-N 2-chloro-1-thiophen-3-ylethanone Chemical compound ClCC(=O)C=1C=CSC=1 DUVRDRIDUGKOHS-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- DAOWEVLVOUMCEY-UHFFFAOYSA-N 3-chloro-1-(4-methylphenyl)propan-1-one Chemical compound CC1=CC=C(C(=O)CCCl)C=C1 DAOWEVLVOUMCEY-UHFFFAOYSA-N 0.000 description 1
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical class ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- LDHNCFIXYHXVDN-UHFFFAOYSA-N 4-(2-chloroacetyl)benzonitrile Chemical compound ClCC(=O)C1=CC=C(C#N)C=C1 LDHNCFIXYHXVDN-UHFFFAOYSA-N 0.000 description 1
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 206010020651 Hyperkinesia Diseases 0.000 description 1
- 208000000269 Hyperkinesis Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical compound CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 1
- BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DMWVWHSVGRDNCJ-UHFFFAOYSA-N [2-(2-chloroacetyl)phenyl] acetate Chemical compound ClCC(=O)C1=C(C=CC=C1)OC(C)=O DMWVWHSVGRDNCJ-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- NMPVEAUIHMEAQP-UHFFFAOYSA-N alpha-bromo-acetaldehyde Natural products BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 201000003104 endogenous depression Diseases 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003447 ipsilateral effect Effects 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001107 psychogenic effect Effects 0.000 description 1
- 239000003368 psychostimulant agent Substances 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- C07D413/02—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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
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 Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8301366A FR2540115B1 (fr) | 1983-01-28 | 1983-01-28 | Derive de la pyridazine ayant une action psychotrope, son mode de preparation et les medicaments en contenant |
| FR8318433A FR2555178B1 (fr) | 1983-11-18 | 1983-11-18 | Derives cyanes de la pyridazine ayant une action psychotrope, leur mode de preparation et les medicaments en contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD215542A5 true DD215542A5 (de) | 1984-11-14 |
Family
ID=26223263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84259679A DD215542A5 (de) | 1983-01-28 | 1984-01-27 | Verfahren zur herstellung von 4-cyano-pyridazinen |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US4565814A (cs) |
| EP (1) | EP0116494B1 (cs) |
| KR (1) | KR910000639B1 (cs) |
| AU (1) | AU566352B2 (cs) |
| CA (1) | CA1218655A (cs) |
| CS (1) | CS274405B2 (cs) |
| DD (1) | DD215542A5 (cs) |
| DE (1) | DE3469026D1 (cs) |
| DK (3) | DK159969C (cs) |
| ES (1) | ES529108A0 (cs) |
| FI (1) | FI77453C (cs) |
| GR (1) | GR81682B (cs) |
| HU (1) | HU192975B (cs) |
| IE (1) | IE56750B1 (cs) |
| IL (1) | IL70755A (cs) |
| MA (1) | MA20019A1 (cs) |
| NO (1) | NO840329L (cs) |
| NZ (1) | NZ206957A (cs) |
| OA (1) | OA07645A (cs) |
| PH (1) | PH21476A (cs) |
| PL (1) | PL143994B1 (cs) |
| PT (1) | PT77994B (cs) |
| SG (1) | SG9389G (cs) |
| SU (1) | SU1274623A3 (cs) |
| YU (1) | YU14184A (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2540113A1 (fr) * | 1983-01-27 | 1984-08-03 | Sanofi Sa | Acides derives de la pyridazine actifs sur le systeme nerveux central |
| PT82753B (pt) * | 1985-06-14 | 1988-12-15 | Lilly Co Eli | Processo para a preparacao de piridazinas uteis como fungicidas |
| US5106973A (en) * | 1987-11-23 | 1992-04-21 | Janssen Pharmaceutica N.V. | Pyridzainamine derivatives |
| DK1112743T3 (da) * | 1998-08-20 | 2007-11-26 | Toyama Chemical Co Ltd | Nitrogenholdige heterocykliske carboxamidderivater eller salte deraf som antivirale midler |
| ES2339738T3 (es) | 1999-01-22 | 2010-05-25 | Elan Pharmaceuticals, Inc. | Derivados de acilo los cuales tratan trastornos relacionados con vla-4. |
| TW200307671A (en) | 2002-05-24 | 2003-12-16 | Elan Pharm Inc | Heteroaryl compounds which inhibit leukocyte adhesion mediated by α 4 integrins |
| TWI281470B (en) | 2002-05-24 | 2007-05-21 | Elan Pharm Inc | Heterocyclic compounds which inhibit leukocyte adhesion mediated by alpha4 integrins |
| AU2005260102A1 (en) * | 2004-05-08 | 2006-01-12 | Novartis International Pharmaceutical Ltd. | 3-aryl-5,6-disubstituted pyridazines |
| EP1741709A1 (en) * | 2005-06-28 | 2007-01-10 | Sanofi-Aventis Deutschland GmbH | Heteroaryl-substituted amides comprising a saturated linker group, and their use as pharmaceuticals |
| AU2006297180A1 (en) | 2005-09-29 | 2007-04-12 | Elan Pharmaceuticals, Inc. | Carbamate compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| EP1940826B1 (en) | 2005-09-29 | 2010-12-29 | Elan Pharmaceuticals Inc. | Pyrimidinyl amide compounds which inhibit leukocyte adhesion mediated by vla-4 |
| EA017110B1 (ru) | 2006-02-27 | 2012-09-28 | Элан Фамэсьютикэлс, Инк. | ПИРИМИДИНИЛСУЛЬФОНАМИДНЫЕ СОЕДИНЕНИЯ (ВАРИАНТЫ), СПОСОБ ПОЛУЧЕНИЯ ПИРИМИДИНИЛСУЛЬФОНАМИДНЫХ СОЕДИНЕНИЙ (ВАРИАНТЫ), ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБ ЛЕЧЕНИЯ ЗАБОЛЕВАНИЯ, ОПОСРЕДОВАННОГО ИНТЕГРИНОМ α4, СПОСОБ СНИЖЕНИЯ И/ИЛИ ПРЕДУПРЕЖДЕНИЯ ВОСПАЛИТЕЛЬНОГО КОМПОНЕНТА ЗАБОЛЕВАНИЯ ИЛИ АУТОИММУННОГО ОТВЕТА |
| SG10201401836RA (en) | 2009-04-27 | 2014-10-30 | Elan Pharm Inc | Pyridinone antagonists of alpha-4 integrins |
| EP2560488B1 (en) | 2010-04-23 | 2015-10-28 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1345880A (en) * | 1971-06-18 | 1974-02-06 | Cepbepe | Pyridazine derivatives |
| FR2510998B1 (fr) * | 1981-08-07 | 1986-01-10 | Sanofi Sa | Nouveaux derives amines de la pyridazine, leur procede de preparation et les medicaments, a action desinhibitrice, qui en comportent |
| FR2510997A1 (fr) * | 1981-08-10 | 1983-02-11 | Sanofi Sa | Nouveaux derives de la methyl-4 phenyl-6 pyridazine, procede pour leur preparation et medicaments actifs sur le systeme nerveux central en contenant |
| FR2539739B1 (fr) * | 1983-01-24 | 1985-11-22 | Sanofi Sa | Nouveaux derives de la naphtyl pyridazine actifs sur le systeme nerveux central, procede de preparation de ces derives et medicaments en contenant |
-
1984
- 1984-01-18 US US06/571,696 patent/US4565814A/en not_active Expired - Fee Related
- 1984-01-18 CA CA000445482A patent/CA1218655A/en not_active Expired
- 1984-01-20 DK DK025984A patent/DK159969C/da not_active IP Right Cessation
- 1984-01-20 PH PH30136A patent/PH21476A/en unknown
- 1984-01-23 GR GR73586A patent/GR81682B/el unknown
- 1984-01-23 PT PT77994A patent/PT77994B/pt not_active IP Right Cessation
- 1984-01-23 IE IE148/84A patent/IE56750B1/en not_active IP Right Cessation
- 1984-01-23 IL IL70755A patent/IL70755A/xx unknown
- 1984-01-24 AU AU23728/84A patent/AU566352B2/en not_active Ceased
- 1984-01-24 ES ES529108A patent/ES529108A0/es active Granted
- 1984-01-25 DE DE8484400157T patent/DE3469026D1/de not_active Expired
- 1984-01-25 EP EP84400157A patent/EP0116494B1/fr not_active Expired
- 1984-01-26 OA OA58217A patent/OA07645A/xx unknown
- 1984-01-26 MA MA20240A patent/MA20019A1/fr unknown
- 1984-01-27 DD DD84259679A patent/DD215542A5/de not_active IP Right Cessation
- 1984-01-27 PL PL1984245932A patent/PL143994B1/pl unknown
- 1984-01-27 CS CS61484A patent/CS274405B2/cs unknown
- 1984-01-27 YU YU00141/84A patent/YU14184A/xx unknown
- 1984-01-27 NZ NZ206957A patent/NZ206957A/en unknown
- 1984-01-27 HU HU84378A patent/HU192975B/hu not_active IP Right Cessation
- 1984-01-27 NO NO840329A patent/NO840329L/no unknown
- 1984-01-27 FI FI840349A patent/FI77453C/fi not_active IP Right Cessation
- 1984-01-27 SU SU843697653A patent/SU1274623A3/ru active
- 1984-01-28 KR KR1019840000387A patent/KR910000639B1/ko not_active Expired
-
1985
- 1985-05-20 US US06/735,580 patent/US4631280A/en not_active Expired - Fee Related
-
1989
- 1989-02-14 SG SG93/89A patent/SG9389G/en unknown
- 1989-12-08 DK DK621689A patent/DK162219C/da not_active IP Right Cessation
- 1989-12-08 DK DK621589A patent/DK162218C/da not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
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| ENJ | Ceased due to non-payment of renewal fee |