NO831614L - 3-amino-6-aryl-1,2,4-triazolo(4,3-b)pyridaziner, deres fremstilling og deres anvendelse - Google Patents
3-amino-6-aryl-1,2,4-triazolo(4,3-b)pyridaziner, deres fremstilling og deres anvendelseInfo
- Publication number
- NO831614L NO831614L NO831614A NO831614A NO831614L NO 831614 L NO831614 L NO 831614L NO 831614 A NO831614 A NO 831614A NO 831614 A NO831614 A NO 831614A NO 831614 L NO831614 L NO 831614L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- carbon atoms
- compound
- groups
- amino
- Prior art date
Links
- 150000004892 pyridazines Chemical class 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- -1 phenoxyphenyl Chemical group 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 239000000460 chlorine Substances 0.000 claims abstract description 15
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 7
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 7
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000004305 biphenyl Substances 0.000 claims abstract description 6
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 239000011737 fluorine Substances 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 3
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 4
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000000949 anxiolytic effect Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims description 2
- 230000001773 anti-convulsant effect Effects 0.000 claims description 2
- 239000002249 anxiolytic agent Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 206010022437 insomnia Diseases 0.000 claims description 2
- 206010003840 Autonomic nervous system imbalance Diseases 0.000 claims 1
- 230000002920 convulsive effect Effects 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 19
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract description 4
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 abstract description 3
- BUTTVUBNXIIXRH-UHFFFAOYSA-N 1-(cyclopropylmethyl)pyrazole-4-carbaldehyde Chemical compound C1=C(C=O)C=NN1CC1CC1 BUTTVUBNXIIXRH-UHFFFAOYSA-N 0.000 abstract description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 abstract description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract description 2
- RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 abstract description 2
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JVANLUCASVHWEW-UHFFFAOYSA-N pyridazine Chemical compound N1=C=C=C=C=N1 JVANLUCASVHWEW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- IXENSJHJYLAODF-UHFFFAOYSA-N 3-bromo-6-(4-methylphenyl)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1=CC(C)=CC=C1C1=NN2C(Br)=NN=C2C=C1 IXENSJHJYLAODF-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- SBBMDEIIUUWPEF-UHFFFAOYSA-N 6-(4-methylphenyl)-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound C1=CC(C)=CC=C1C1=NN2C=NN=C2C=C1 SBBMDEIIUUWPEF-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- UZBFYYNRFGFLGI-UHFFFAOYSA-N [(6-phenylpyridazin-3-yl)amino]thiourea Chemical compound N1=NC(NNC(=S)N)=CC=C1C1=CC=CC=C1 UZBFYYNRFGFLGI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- 230000007306 turnover Effects 0.000 description 2
- 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 1
- ZNGXOKMCRDQBON-UHFFFAOYSA-N (6-phenylpyridazin-3-yl)hydrazine Chemical compound N1=NC(NN)=CC=C1C1=CC=CC=C1 ZNGXOKMCRDQBON-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BUBRFWDEAVIFMV-UHFFFAOYSA-N 3-chloro-6-phenylpyridazine Chemical compound N1=NC(Cl)=CC=C1C1=CC=CC=C1 BUBRFWDEAVIFMV-UHFFFAOYSA-N 0.000 description 1
- YIWADZFLXOZDQQ-UHFFFAOYSA-N 4-(3-amino-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)benzonitrile Chemical compound N=1N2C(N)=NN=C2C=CC=1C1=CC=C(C#N)C=C1 YIWADZFLXOZDQQ-UHFFFAOYSA-N 0.000 description 1
- NESUCTBTEUQLOZ-UHFFFAOYSA-N 6-(1-methylpyrrol-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound CN1C=CC=C1C1=NN2C(N)=NN=C2C=C1 NESUCTBTEUQLOZ-UHFFFAOYSA-N 0.000 description 1
- GRRRNIQVPWPHQS-UHFFFAOYSA-N 6-(1H-pyrrol-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound NC1=NN=C2N1N=C(C=C2)C=1NC=CC=1 GRRRNIQVPWPHQS-UHFFFAOYSA-N 0.000 description 1
- PSCUSLLLANPIAJ-UHFFFAOYSA-N 6-(2-bromophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound N=1N2C(N)=NN=C2C=CC=1C1=CC=CC=C1Br PSCUSLLLANPIAJ-UHFFFAOYSA-N 0.000 description 1
- VTRWYNGBVUXCEG-UHFFFAOYSA-N 6-(2-ethylphenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound CCC1=CC=CC=C1C1=NN2C(N)=NN=C2C=C1 VTRWYNGBVUXCEG-UHFFFAOYSA-N 0.000 description 1
- JTBQVGVMBBFRNF-UHFFFAOYSA-N 6-(2-methylphenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound CC1=CC=CC=C1C1=NN2C(N)=NN=C2C=C1 JTBQVGVMBBFRNF-UHFFFAOYSA-N 0.000 description 1
- PBSVCHYZZQKCCD-UHFFFAOYSA-N 6-(2-nitrophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound N=1N2C(N)=NN=C2C=CC=1C1=CC=CC=C1[N+]([O-])=O PBSVCHYZZQKCCD-UHFFFAOYSA-N 0.000 description 1
- MVALQLWINGFNCC-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound N=1N2C(N)=NN=C2C=CC=1C1=CC=C(Cl)C(Cl)=C1 MVALQLWINGFNCC-UHFFFAOYSA-N 0.000 description 1
- RYFALDHNEPTXIF-UHFFFAOYSA-N 6-(4-aminophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound N=1N2C(N)=NN=C2C=CC=1C1=CC=C(N)C=C1 RYFALDHNEPTXIF-UHFFFAOYSA-N 0.000 description 1
- RHGGVVAPFBYAQX-UHFFFAOYSA-N 6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine;hydrochloride Chemical compound Cl.N=1N2C(N)=NN=C2C=CC=1C1=CC=C(F)C=C1 RHGGVVAPFBYAQX-UHFFFAOYSA-N 0.000 description 1
- OWMAODZSQHQTFC-UHFFFAOYSA-N 6-(4-methylphenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound C1=CC(C)=CC=C1C1=NN2C(N)=NN=C2C=C1 OWMAODZSQHQTFC-UHFFFAOYSA-N 0.000 description 1
- OOAVJMKRMCZRIB-UHFFFAOYSA-N 6-(4-nitrophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound N=1N2C(N)=NN=C2C=CC=1C1=CC=C([N+]([O-])=O)C=C1 OOAVJMKRMCZRIB-UHFFFAOYSA-N 0.000 description 1
- ZTHXWLWNXCCCEA-UHFFFAOYSA-N 6-(4-propylsulfanylphenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound C1=CC(SCCC)=CC=C1C1=NN2C(N)=NN=C2C=C1 ZTHXWLWNXCCCEA-UHFFFAOYSA-N 0.000 description 1
- IZRVHCGGFMGJTB-UHFFFAOYSA-N 6-(5-methylfuran-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound O1C(C)=CC=C1C1=NN2C(N)=NN=C2C=C1 IZRVHCGGFMGJTB-UHFFFAOYSA-N 0.000 description 1
- IWTZBWDZUCQHFQ-UHFFFAOYSA-N 6-[2-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound N=1N2C(N)=NN=C2C=CC=1C1=CC=CC=C1C(F)(F)F IWTZBWDZUCQHFQ-UHFFFAOYSA-N 0.000 description 1
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- BWDKRNKKDDGBRF-UHFFFAOYSA-N 6-pyridin-3-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound N=1N2C(N)=NN=C2C=CC=1C1=CC=CN=C1 BWDKRNKKDDGBRF-UHFFFAOYSA-N 0.000 description 1
- JDWCNSLLTCFOFR-UHFFFAOYSA-N 6-pyridin-4-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-amine Chemical compound N=1N2C(N)=NN=C2C=CC=1C1=CC=NC=C1 JDWCNSLLTCFOFR-UHFFFAOYSA-N 0.000 description 1
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
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- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- MHGGAHUZDJJPHB-UHFFFAOYSA-N [6-(4-fluorophenyl)pyridazin-3-yl]hydrazine Chemical compound N1=NC(NN)=CC=C1C1=CC=C(F)C=C1 MHGGAHUZDJJPHB-UHFFFAOYSA-N 0.000 description 1
- MORPXDYMWBGQNW-UHFFFAOYSA-N [6-(4-methylphenyl)pyridazin-3-yl]hydrazine Chemical compound C1=CC(C)=CC=C1C1=CC=C(NN)N=N1 MORPXDYMWBGQNW-UHFFFAOYSA-N 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 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
- 239000011976 maleic acid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- MTHMVLLKCNMJQL-UHFFFAOYSA-N oxalonitrile hydrobromide Chemical compound Br.N#CC#N MTHMVLLKCNMJQL-UHFFFAOYSA-N 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- C07D237/20—Nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823217325 DE3217325A1 (de) | 1982-05-08 | 1982-05-08 | 3-amino-6-aryl-1,2,4-triazolo(4,3-b)-pyridazine, ihre herstellung und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO831614L true NO831614L (no) | 1983-11-09 |
Family
ID=6163075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO831614A NO831614L (no) | 1982-05-08 | 1983-05-06 | 3-amino-6-aryl-1,2,4-triazolo(4,3-b)pyridaziner, deres fremstilling og deres anvendelse |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0094038B1 (es) |
| JP (1) | JPS58203992A (es) |
| KR (1) | KR840004753A (es) |
| AT (1) | ATE24728T1 (es) |
| AU (1) | AU1434383A (es) |
| CA (1) | CA1201122A (es) |
| DE (2) | DE3217325A1 (es) |
| DK (1) | DK204783A (es) |
| ES (4) | ES8405800A1 (es) |
| FI (1) | FI831548L (es) |
| GR (1) | GR79281B (es) |
| HU (1) | HU189277B (es) |
| IE (1) | IE55096B1 (es) |
| IL (1) | IL68611A0 (es) |
| MA (1) | MA19791A1 (es) |
| NO (1) | NO831614L (es) |
| NZ (1) | NZ204153A (es) |
| PT (1) | PT76654B (es) |
| ZA (1) | ZA833239B (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3311753A1 (de) * | 1983-03-31 | 1984-10-04 | Hoechst Ag, 6230 Frankfurt | Substituierte 6-aryl-1,2,4-triazolo(4,3-b)pyridazine - ihre herstellung und verwendung - |
| FR2562071B1 (fr) * | 1984-03-30 | 1986-12-19 | Sanofi Sa | Triazolo(4,3-b)pyridazines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US4654343A (en) * | 1985-10-31 | 1987-03-31 | American Cyanamid Company | N-substituted-N[3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]alkanamides, carbamates and ureas |
| WO2006050359A2 (en) | 2004-11-02 | 2006-05-11 | Northwestern University | Pyridazine compounds and methods |
| ES2543813T3 (es) | 2004-11-02 | 2015-08-24 | Northwestern University | Compuestos de piridazina para el tratamiento de enfermedades inflamatorias |
| WO2007127375A2 (en) | 2006-04-28 | 2007-11-08 | Northwestern University | Formulations containing pyridazine compounds for treating neuroinflammatory diseases |
| WO2007127474A2 (en) | 2006-04-28 | 2007-11-08 | Northwestern University | Compositions and treatments using pyridazine compounds and cholinesterase inhibitors |
| EP2131839A2 (en) * | 2007-03-02 | 2009-12-16 | Northwestern University | Compositions comprising derivatives of 3-phenylpyridazine for treating seizure-related disorders |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL128809C (es) * | 1966-06-18 | |||
| US3708484A (en) * | 1970-10-16 | 1973-01-02 | Sandoz Ag | Amino and substituted amino-s-triazolo-(4,3-b)-pyridazines |
| DE2113438A1 (de) * | 1971-03-19 | 1972-09-21 | Boehringer Mannheim Gmbh | Nitrofuryl-triazolo[4,3-b]pyridazinderivate |
| CA1080712A (en) * | 1976-09-22 | 1980-07-01 | Jay D. Albright | Hypotensive agents |
| US4260756A (en) * | 1979-11-15 | 1981-04-07 | American Cyanamid Company | 6- And 8-heteroaryl-1,2,4-triazolo[4,3-b]pyridazines |
-
1982
- 1982-05-08 DE DE19823217325 patent/DE3217325A1/de not_active Withdrawn
-
1983
- 1983-05-04 GR GR71294A patent/GR79281B/el unknown
- 1983-05-05 FI FI831548A patent/FI831548L/fi not_active Application Discontinuation
- 1983-05-05 AT AT83104427T patent/ATE24728T1/de not_active IP Right Cessation
- 1983-05-05 DE DE8383104427T patent/DE3368931D1/de not_active Expired
- 1983-05-05 EP EP83104427A patent/EP0094038B1/de not_active Expired
- 1983-05-06 IL IL68611A patent/IL68611A0/xx unknown
- 1983-05-06 AU AU14343/83A patent/AU1434383A/en not_active Abandoned
- 1983-05-06 IE IE1043/83A patent/IE55096B1/en unknown
- 1983-05-06 PT PT76654A patent/PT76654B/pt unknown
- 1983-05-06 DK DK204783A patent/DK204783A/da not_active Application Discontinuation
- 1983-05-06 MA MA20012A patent/MA19791A1/fr unknown
- 1983-05-06 ES ES522144A patent/ES8405800A1/es not_active Expired
- 1983-05-06 NZ NZ204153A patent/NZ204153A/en unknown
- 1983-05-06 CA CA000427630A patent/CA1201122A/en not_active Expired
- 1983-05-06 JP JP58078423A patent/JPS58203992A/ja active Pending
- 1983-05-06 NO NO831614A patent/NO831614L/no unknown
- 1983-05-06 KR KR1019830001924A patent/KR840004753A/ko not_active Application Discontinuation
- 1983-05-06 HU HU831579A patent/HU189277B/hu unknown
- 1983-05-06 ZA ZA833239A patent/ZA833239B/xx unknown
-
1984
- 1984-03-15 ES ES530639A patent/ES530639A0/es active Granted
- 1984-03-15 ES ES530638A patent/ES530638A0/es active Granted
- 1984-03-15 ES ES530640A patent/ES8501400A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1201122A (en) | 1986-02-25 |
| GR79281B (es) | 1984-10-22 |
| AU1434383A (en) | 1983-11-10 |
| ZA833239B (en) | 1984-01-25 |
| ES530640A0 (es) | 1984-11-16 |
| IL68611A0 (en) | 1983-09-30 |
| IE55096B1 (en) | 1990-05-23 |
| ES8501399A1 (es) | 1984-11-16 |
| DK204783D0 (da) | 1983-05-06 |
| KR840004753A (ko) | 1984-10-24 |
| DE3217325A1 (de) | 1983-11-10 |
| NZ204153A (en) | 1985-04-30 |
| PT76654B (de) | 1986-01-28 |
| ES522144A0 (es) | 1984-06-16 |
| ES8501398A1 (es) | 1984-11-16 |
| DE3368931D1 (en) | 1987-02-12 |
| ES530639A0 (es) | 1984-11-16 |
| FI831548A0 (fi) | 1983-05-05 |
| EP0094038B1 (de) | 1987-01-07 |
| IE831043L (en) | 1983-11-08 |
| DK204783A (da) | 1983-11-09 |
| MA19791A1 (fr) | 1983-12-31 |
| FI831548L (fi) | 1983-11-09 |
| ES8405800A1 (es) | 1984-06-16 |
| ATE24728T1 (de) | 1987-01-15 |
| ES530638A0 (es) | 1984-11-16 |
| ES8501400A1 (es) | 1984-11-16 |
| HU189277B (en) | 1986-06-30 |
| PT76654A (de) | 1983-06-01 |
| JPS58203992A (ja) | 1983-11-28 |
| EP0094038A1 (de) | 1983-11-16 |
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