CH547814A - Verfahren zur herstellung neuer pyrido (4,3-c)pyridazine. - Google Patents
Verfahren zur herstellung neuer pyrido (4,3-c)pyridazine.Info
- Publication number
- CH547814A CH547814A CH768371A CH768371A CH547814A CH 547814 A CH547814 A CH 547814A CH 768371 A CH768371 A CH 768371A CH 768371 A CH768371 A CH 768371A CH 547814 A CH547814 A CH 547814A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- pyridazine
- compounds
- tetrahydropyrido
- decomposition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- RGWAZXHUULNXGT-UHFFFAOYSA-N pyrido[4,3-c]pyridazine Chemical compound N1=CC=C2C=NC=CC2=N1 RGWAZXHUULNXGT-UHFFFAOYSA-N 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 238000000354 decomposition reaction Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 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 8
- -1 cyclic amine Chemical class 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- UDABHERMEKWUDP-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-chloro-5,6,7,8-tetrahydropyrido[4,3-c]pyridazine Chemical compound OC(=O)\C=C/C(O)=O.C1NCCC2=C1C=C(Cl)N=N2 UDABHERMEKWUDP-BTJKTKAUSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- FRJIVADTLWHFKU-UHFFFAOYSA-N (2-fluorophenyl)-(3-hydrazinyl-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl)methanone Chemical compound C1CC=2N=NC(NN)=CC=2CN1C(=O)C1=CC=CC=C1F FRJIVADTLWHFKU-UHFFFAOYSA-N 0.000 description 2
- FEFYEUNDAOJDCQ-UHFFFAOYSA-N (3-chloro-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2=CC(Cl)=NN=C2CC1 FEFYEUNDAOJDCQ-UHFFFAOYSA-N 0.000 description 2
- BQXSACKHPWOYLT-UHFFFAOYSA-N (3-chloro-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl)-phenylmethanone Chemical compound C1CC=2N=NC(Cl)=CC=2CN1C(=O)C1=CC=CC=C1 BQXSACKHPWOYLT-UHFFFAOYSA-N 0.000 description 2
- IIIDPTXDTHOYRK-UHFFFAOYSA-N 5,6,7,8-tetrahydropyrido[4,3-c]pyridazin-6-ium-3-olate Chemical compound C1NCCC2=NNC(=O)C=C21 IIIDPTXDTHOYRK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- ALAXZYHFVBSJKZ-UHFFFAOYSA-N endralazine Chemical compound C1CC=2N=NC(NN)=CC=2CN1C(=O)C1=CC=CC=C1 ALAXZYHFVBSJKZ-UHFFFAOYSA-N 0.000 description 2
- LBUWFLGJLUHKJK-UHFFFAOYSA-N ethyl 3-oxo-2,5,7,8-tetrahydropyrido[4,3-c]pyridazine-6-carboxylate Chemical compound N1C(=O)C=C2CN(C(=O)OCC)CCC2=N1 LBUWFLGJLUHKJK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- KOBLUAJLPQOZCT-UHFFFAOYSA-N (2-fluorophenyl)-[3-(2-propan-2-ylidenehydrazinyl)-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl]methanone Chemical compound C1CC=2N=NC(NN=C(C)C)=CC=2CN1C(=O)C1=CC=CC=C1F KOBLUAJLPQOZCT-UHFFFAOYSA-N 0.000 description 1
- ZYGQKGNXOIBXMG-UHFFFAOYSA-N (3-chloro-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl)-(2-fluorophenyl)methanone Chemical compound FC1=CC=CC=C1C(=O)N1CC2=CC(Cl)=NN=C2CC1 ZYGQKGNXOIBXMG-UHFFFAOYSA-N 0.000 description 1
- ZDJYIWZRHCUVIZ-UHFFFAOYSA-N (3-chloro-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1CC2=CC(Cl)=NN=C2CC1 ZDJYIWZRHCUVIZ-UHFFFAOYSA-N 0.000 description 1
- SWAZKOODQFIQQC-UHFFFAOYSA-N (3-hydrazinyl-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1CC2=CC(NN)=NN=C2CC1 SWAZKOODQFIQQC-UHFFFAOYSA-N 0.000 description 1
- MTSBSKMNZFQCLX-UHFFFAOYSA-N (4-chlorophenyl)-(3-hydrazinyl-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl)methanone Chemical compound C1CC=2N=NC(NN)=CC=2CN1C(=O)C1=CC=C(Cl)C=C1 MTSBSKMNZFQCLX-UHFFFAOYSA-N 0.000 description 1
- IQDZKRWPNQRHNY-UHFFFAOYSA-N (4-chlorophenyl)-[3-(2-propan-2-ylidenehydrazinyl)-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl]methanone Chemical compound C1CC=2N=NC(NN=C(C)C)=CC=2CN1C(=O)C1=CC=C(Cl)C=C1 IQDZKRWPNQRHNY-UHFFFAOYSA-N 0.000 description 1
- SYSATALHMMDBPP-BTJKTKAUSA-N (z)-but-2-enedioic acid;pyridazine Chemical compound C1=CC=NN=C1.OC(=O)\C=C/C(O)=O SYSATALHMMDBPP-BTJKTKAUSA-N 0.000 description 1
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- ALJUPDQYZZRFSN-UHFFFAOYSA-N 3-chloro-5,6,7,8-tetrahydropyrido[4,3-c]pyridazine Chemical compound C1NCCC2=C1C=C(Cl)N=N2 ALJUPDQYZZRFSN-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BPDJCKXWRAOWOU-UHFFFAOYSA-N [3-(2-cyclohexylidenehydrazinyl)-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1CC2=CC(NN=C3CCCCC3)=NN=C2CC1 BPDJCKXWRAOWOU-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- QTMIUGYAPDKBKM-UHFFFAOYSA-N ethyl 3-oxo-2,4,4a,5,7,8-hexahydropyrido[4,3-c]pyridazine-6-carboxylate Chemical compound N1C(=O)CC2CN(C(=O)OCC)CCC2=N1 QTMIUGYAPDKBKM-UHFFFAOYSA-N 0.000 description 1
- LUBGFMZTGFXIIN-UHFFFAOYSA-N ethyl 4-oxopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(=O)CC1 LUBGFMZTGFXIIN-UHFFFAOYSA-N 0.000 description 1
- BOBUJEPCIKNLDK-UHFFFAOYSA-N ethyl 4-pyrrolidin-1-yl-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC(N2CCCC2)=C1 BOBUJEPCIKNLDK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- AIUZKHOYNNOAFK-UHFFFAOYSA-N phenyl-[3-(2-propan-2-ylidenehydrazinyl)-7,8-dihydro-5h-pyrido[4,3-c]pyridazin-6-yl]methanone Chemical compound C1CC=2N=NC(NN=C(C)C)=CC=2CN1C(=O)C1=CC=CC=C1 AIUZKHOYNNOAFK-UHFFFAOYSA-N 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH768371A CH547814A (de) | 1971-05-26 | 1971-05-26 | Verfahren zur herstellung neuer pyrido (4,3-c)pyridazine. |
| CH1512171A CH555841A (de) | 1971-05-26 | 1971-10-15 | Verfahren zur herstellung neuer 3-hydrazinopyrido-(4,3c)pyridazine. |
| CH239372A CH561207A5 (en) | 1971-05-26 | 1972-02-19 | 3-(Cyclo)alkylidenehydrazino-6-acyl-pyrido(4,3-c)pyridazines - with antihypertensive activity |
| CH305172A CH560699A5 (enrdf_load_stackoverflow) | 1971-05-26 | 1972-03-02 | |
| FI1245/72A FI55343C (fi) | 1971-05-11 | 1972-05-02 | Foerfarande foer framstaellning av nya, blodtryckssaenkande 3-hydrazinopyrido(4,3-c)pyridazinderivat |
| NO1533/72A NO136251C (no) | 1971-05-11 | 1972-05-02 | Analogifremgangsm}te for fremstilling av terapeutisk aktive pyridazin-derivater. |
| DK217572AA DK139625B (da) | 1971-05-11 | 1972-05-02 | Analogifremgangsmåde til fremstilling af cycloalkan(c)pyridazin- eller pyrido(4,3-c)pyridazinderivater eller syreadditionssalte deraf. |
| SE7205731A SE400557B (sv) | 1971-05-11 | 1972-05-02 | Forfarande for framstellning av nya kondenserade pyridaziner |
| GB4572274A GB1392475A (en) | 1971-05-11 | 1972-05-05 | Hydrazino-pyrimido-pyridazine derivative |
| GB2106072A GB1392474A (en) | 1971-05-11 | 1972-05-05 | Hydrazinopyridazine derivatives |
| US00251035A US3838125A (en) | 1971-05-11 | 1972-05-08 | 6-substituted-5,6,7,8-tetrahydro-3-hydrazino(substituted hydrazino)pyrido(4,3-c)pyridazines |
| BE783219A BE783219A (fr) | 1971-05-11 | 1972-05-09 | Nouveaux composes heterocycliques, leur preparation et leur applicationcomme medicaments |
| PL1972155270A PL81827B1 (enrdf_load_stackoverflow) | 1971-05-11 | 1972-05-09 | |
| IE617/72A IE36710B1 (en) | 1971-05-11 | 1972-05-09 | Hydrazinopyridazine derivatives |
| DD162838A DD97418A5 (enrdf_load_stackoverflow) | 1971-05-11 | 1972-05-09 | |
| IL39392A IL39392A (en) | 1971-05-11 | 1972-05-09 | Aminopyridazine derivatives their preparation and pharmaceutical compositions containing them |
| HUSA2354A HU168682B (enrdf_load_stackoverflow) | 1971-05-11 | 1972-05-09 | |
| AU42135/72A AU472726B2 (en) | 1971-05-11 | 1972-05-10 | Aminopyridazine derivatives and their preparation |
| CA141,760A CA943542A (en) | 1971-05-11 | 1972-05-10 | Aminopyridazine derivatives |
| JP47046266A JPS5750791B1 (enrdf_load_stackoverflow) | 1971-05-11 | 1972-05-10 | |
| NLAANVRAGE7206477,A NL176565C (nl) | 1971-05-11 | 1972-05-12 | Werkwijze voor het bereiden of vervaardigen van een farmaceutisch preparaat met hypotensieve werking alsmede werkwijze voor het bereiden van verbindingen geschikt voor toepassing bij voornoemde werkwijze. |
| SU1993887A SU493968A3 (ru) | 1971-05-11 | 1974-02-06 | Способ получени конденсированных производных пиридазина |
| US05/485,578 US3954754A (en) | 1971-05-11 | 1974-07-03 | 3-Hydrazino-cycloalkyl[c]pyridazines |
| AT709074A ATA709074A (de) | 1971-05-11 | 1974-09-02 | Verfahren zur herstellung neuer pyridazinderivate |
| US06/029,892 US4478837A (en) | 1971-05-11 | 1979-04-13 | 3-Hydrazino cycloalkyl[c]pyridazines as antihypertensive agents |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH768371A CH547814A (de) | 1971-05-26 | 1971-05-26 | Verfahren zur herstellung neuer pyrido (4,3-c)pyridazine. |
| CH239372A CH561207A5 (en) | 1971-05-26 | 1972-02-19 | 3-(Cyclo)alkylidenehydrazino-6-acyl-pyrido(4,3-c)pyridazines - with antihypertensive activity |
| CH277972A CH560214A5 (en) | 1972-02-28 | 1972-02-28 | 6-Substd.-3-substd. hydrazinopyrido(4,3-c) - pyridazines - as antihypertensives, obtd. from corresp 3-halopyrido (4,3-c)pyridazines and hydrazine hydrate |
| CH286372A CH560215A5 (enrdf_load_stackoverflow) | 1972-02-28 | 1972-02-29 | |
| CH305172A CH560699A5 (enrdf_load_stackoverflow) | 1971-05-26 | 1972-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH547814A true CH547814A (de) | 1974-04-11 |
Family
ID=33102462
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH768371A CH547814A (de) | 1971-05-11 | 1971-05-26 | Verfahren zur herstellung neuer pyrido (4,3-c)pyridazine. |
| CH305172A CH560699A5 (enrdf_load_stackoverflow) | 1971-05-26 | 1972-03-02 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH305172A CH560699A5 (enrdf_load_stackoverflow) | 1971-05-26 | 1972-03-02 |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH547814A (enrdf_load_stackoverflow) |
-
1971
- 1971-05-26 CH CH768371A patent/CH547814A/de not_active IP Right Cessation
-
1972
- 1972-03-02 CH CH305172A patent/CH560699A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH560699A5 (enrdf_load_stackoverflow) | 1975-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT390257B (de) | Verfahren zur herstellung neuer imidazo(4,5-b)chinolin-derivate | |
| CH622261A5 (enrdf_load_stackoverflow) | ||
| DD161210A5 (de) | Verfahren zur herstellung neuer 3-substituierter beta-carboline | |
| DE2854115C2 (enrdf_load_stackoverflow) | ||
| DE2851028A1 (de) | Neue indolo eckige klammer auf 2.3-a eckige klammer zu chinolizidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitung | |
| DD289529A5 (de) | Verfahren zur herstellung heterozyklischer verbindungen | |
| DD202563A5 (de) | Verfahren zur herstellung von 1,5-diphenylpyrazolin-3-on-verbindungen | |
| EP0180833B1 (de) | 4-Oxo-pyrido[2,3]pyrimidin-Derivate, Verfahren zur deren Herstellung und diese ethaltende Arzneimittel | |
| CH547814A (de) | Verfahren zur herstellung neuer pyrido (4,3-c)pyridazine. | |
| DE2221808C2 (de) | Hydrazinopyridazin-Derivate, deren Säureadditionssalze, Verfahren zu deren Herstellung und Heilmittel | |
| DE2521920A1 (de) | Neue derivate von 1h-triazolo(4,5-c) pyridin-7-carbonsaeuren und -saeureestern | |
| DE2059164A1 (de) | Verfahren zur Herstellung von 4-Amino-6,7,8-trialkoxychinazolinen | |
| CH559748A5 (en) | Antihypertensive 3-hydrazinopyrido (4,3-c) py-ridazines - prepd. from corresp. 3-halopyrido(4,3-c)pyridazines and hydrazine hydrate | |
| CH641800A5 (de) | Pyrido-pyrimidine, verfahren zu ihrer herstellung und die diese verbindungen enthaltenden arzneimittel. | |
| CH561211A5 (en) | Antihypertensive 3-hydrazino pyrido(4,3-c)pyridazines - prepd. by reacting corresp 3-halo cpd. with hydrazines | |
| CH560214A5 (en) | 6-Substd.-3-substd. hydrazinopyrido(4,3-c) - pyridazines - as antihypertensives, obtd. from corresp 3-halopyrido (4,3-c)pyridazines and hydrazine hydrate | |
| CH555841A (de) | Verfahren zur herstellung neuer 3-hydrazinopyrido-(4,3c)pyridazine. | |
| CH551433A (de) | Verfahren zur herstellung neuer 3-hydrazino-5,6,7,8-tetrahydropyrido (4,3-c)pyridazin-derivate. | |
| CH553201A (de) | Verfahren zur herstellung neuer pyrido (4,3-c)pyridazinderivate. | |
| CH547813A (de) | Verfahren zur herstellung neuer pyrido (4,3-c)pyridazine. | |
| AT250338B (de) | Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen | |
| CH561186A5 (en) | Bicyclic 3-(cyclo)alkylidenehydrazino-pyridazine derivs - with antihypertensive activity | |
| CH561207A5 (en) | 3-(Cyclo)alkylidenehydrazino-6-acyl-pyrido(4,3-c)pyridazines - with antihypertensive activity | |
| DE3017560A1 (de) | 9-amino-6,7-dihydro-4h-pyrido eckige klammer auf 1,2-a eckige klammer zu pyrimidin-4-on-derivate, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische kompositionen | |
| CH565797A5 (en) | Antihypertensive pyridazine derivs - 3-hydrazino cycloalka(c)pyridazines and pyrido(4,3-c)pyridazines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |