DE2207517A1 - Pyridazinone, Verfahren zu ihrer Herstellung und diese Verbindungen ent haltende Arzneipraparate - Google Patents
Pyridazinone, Verfahren zu ihrer Herstellung und diese Verbindungen ent haltende ArzneipraparateInfo
- Publication number
- DE2207517A1 DE2207517A1 DE19722207517 DE2207517A DE2207517A1 DE 2207517 A1 DE2207517 A1 DE 2207517A1 DE 19722207517 DE19722207517 DE 19722207517 DE 2207517 A DE2207517 A DE 2207517A DE 2207517 A1 DE2207517 A1 DE 2207517A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- group
- pyridazinone
- dihydro
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 title claims description 7
- -1 o-Ethoxyphenyl Chemical group 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 28
- 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 claims description 15
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229940014800 succinic anhydride Drugs 0.000 claims description 6
- KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical compound OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- JWBHLQRIGPMEQZ-UHFFFAOYSA-N 3-(4-hexoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NNC(=O)CC1 JWBHLQRIGPMEQZ-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- WZZRJCUYSKKFHO-UHFFFAOYSA-N 2-(n-benzoyl-3,4-dichloroanilino)propanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 WZZRJCUYSKKFHO-UHFFFAOYSA-N 0.000 claims 1
- HZFNOSJNELIYPU-UHFFFAOYSA-N 3-(2-methoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound COC1=CC=CC=C1C1=NNC(=O)CC1 HZFNOSJNELIYPU-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 238000006193 diazotization reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 230000000802 nitrating effect Effects 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical class [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BCICYRSMWMXMRW-UHFFFAOYSA-N 4-(3-amino-4-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(C(=O)CCC(O)=O)C=C1N BCICYRSMWMXMRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical group C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 2
- ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 description 2
- WUYWHIAAQYQKPP-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(F)C=C1 WUYWHIAAQYQKPP-UHFFFAOYSA-N 0.000 description 2
- YVSNXXBSZQLMNJ-UHFFFAOYSA-N 4-hydroxy-5-phenyl-1h-pyridazin-6-one Chemical compound C1=NNC(=O)C(C=2C=CC=CC=2)=C1O YVSNXXBSZQLMNJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 241000243251 Hydra Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- MKGFYMKFBCWNCP-UHFFFAOYSA-N 1,3-diethoxybenzene Chemical compound CCOC1=CC=CC(OCC)=C1 MKGFYMKFBCWNCP-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- BUZZUHJODKQYTF-UHFFFAOYSA-N 1-iodo-3-methylbutane Chemical compound CC(C)CCI BUZZUHJODKQYTF-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- CAHACRQJGINHMY-UHFFFAOYSA-N 3-(2,4-diethoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound CCOC1=CC(OCC)=CC=C1C1=NNC(=O)CC1 CAHACRQJGINHMY-UHFFFAOYSA-N 0.000 description 1
- WJDUPQCKTRWCBP-UHFFFAOYSA-N 3-(2-hexoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound CCCCCCOC1=CC=CC=C1C1=NNC(=O)CC1 WJDUPQCKTRWCBP-UHFFFAOYSA-N 0.000 description 1
- VYEMEVURJOXQDM-UHFFFAOYSA-N 3-(2-hydroxy-5-methoxyphenyl)-4,5-dihydro-1H-pyridazin-6-one Chemical compound COC1=CC=C(O)C(C=2CCC(=O)NN=2)=C1 VYEMEVURJOXQDM-UHFFFAOYSA-N 0.000 description 1
- YKMXRRMBFZMVAV-UHFFFAOYSA-N 3-(2-methoxy-4-methylphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound COC1=CC(C)=CC=C1C1=NNC(=O)CC1 YKMXRRMBFZMVAV-UHFFFAOYSA-N 0.000 description 1
- UDOJZSYUEOOMPR-UHFFFAOYSA-N 3-(2-propoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound CCCOC1=CC=CC=C1C1=NNC(=O)CC1 UDOJZSYUEOOMPR-UHFFFAOYSA-N 0.000 description 1
- JGXSPVNGIXCGFI-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NNC(=O)CC1 JGXSPVNGIXCGFI-UHFFFAOYSA-N 0.000 description 1
- IPNCBWQSIIAJGO-UHFFFAOYSA-N 3-(3-methoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound COC1=CC=CC(C=2CCC(=O)NN=2)=C1 IPNCBWQSIIAJGO-UHFFFAOYSA-N 0.000 description 1
- UCBSDEIESXJXND-UHFFFAOYSA-N 3-(4-butoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(OCCCC)=CC=C1C1=NNC(=O)CC1 UCBSDEIESXJXND-UHFFFAOYSA-N 0.000 description 1
- BIVIRYQCHHUVDX-UHFFFAOYSA-N 3-(4-cyclohexylphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C=2C=CC(=CC=2)C2CCCCC2)=N1 BIVIRYQCHHUVDX-UHFFFAOYSA-N 0.000 description 1
- CKONBUGAZNEEMK-UHFFFAOYSA-N 3-(4-fluorophenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(F)=CC=C1C1=NNC(=O)CC1 CKONBUGAZNEEMK-UHFFFAOYSA-N 0.000 description 1
- MTICNKXBSUMQLM-UHFFFAOYSA-N 3-(4-heptoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(OCCCCCCC)=CC=C1C1=NNC(=O)CC1 MTICNKXBSUMQLM-UHFFFAOYSA-N 0.000 description 1
- UMQOILNLVDGCQM-UHFFFAOYSA-N 3-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyridazin-6-one Chemical compound C1=C(O)C(OC)=CC(C=2CCC(=O)NN=2)=C1 UMQOILNLVDGCQM-UHFFFAOYSA-N 0.000 description 1
- FUCSFIGFMXFWKH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyridazin-6-one Chemical compound C1=CC(O)=CC=C1C1=NNC(=O)CC1 FUCSFIGFMXFWKH-UHFFFAOYSA-N 0.000 description 1
- MDNFOMPBXKCSSU-UHFFFAOYSA-N 3-(4-phenoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 MDNFOMPBXKCSSU-UHFFFAOYSA-N 0.000 description 1
- JECPTYOLILQNAT-UHFFFAOYSA-N 3-(4-propoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(OCCC)=CC=C1C1=NNC(=O)CC1 JECPTYOLILQNAT-UHFFFAOYSA-N 0.000 description 1
- FTKQAIHBOSYKDN-UHFFFAOYSA-N 4-(2,4-diethoxyphenyl)-4-oxobutanoic acid Chemical compound CCOC1=CC=C(C(=O)CCC(O)=O)C(OCC)=C1 FTKQAIHBOSYKDN-UHFFFAOYSA-N 0.000 description 1
- AFDKBUGRHMPMDP-UHFFFAOYSA-N 4-(3-acetamido-4-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(C(=O)CCC(O)=O)C=C1NC(C)=O AFDKBUGRHMPMDP-UHFFFAOYSA-N 0.000 description 1
- QENTYZPVWYNRLA-UHFFFAOYSA-N 4-(4-cyclohexyloxyphenyl)-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OC1CCCCC1 QENTYZPVWYNRLA-UHFFFAOYSA-N 0.000 description 1
- SCEKMLIWHCMDAB-UHFFFAOYSA-N 4-(4-cyclopentylphenyl)-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1CCCC1 SCEKMLIWHCMDAB-UHFFFAOYSA-N 0.000 description 1
- MITUCWWQUUFNNX-UHFFFAOYSA-N 4-(4-hydroxy-3-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC(C(=O)CCC(O)=O)=CC=C1O MITUCWWQUUFNNX-UHFFFAOYSA-N 0.000 description 1
- QKDLXQWEBIYZSS-UHFFFAOYSA-N 4-(4-hydroxyphenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(O)C=C1 QKDLXQWEBIYZSS-UHFFFAOYSA-N 0.000 description 1
- QICAYWSYAZMUKR-UHFFFAOYSA-N 4-oxo-4-(2-propoxyphenyl)butanoic acid Chemical compound CCCOC1=CC=CC=C1C(=O)CCC(O)=O QICAYWSYAZMUKR-UHFFFAOYSA-N 0.000 description 1
- ZPGMILRNERWUIG-UHFFFAOYSA-N 4-oxo-4-(4-piperidin-1-ylphenyl)butanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1N1CCCCC1 ZPGMILRNERWUIG-UHFFFAOYSA-N 0.000 description 1
- XYZVSEPTKOAAPV-UHFFFAOYSA-N 4-oxo-4-(4-propoxyphenyl)butanoic acid Chemical compound CCCOC1=CC=C(C(=O)CCC(O)=O)C=C1 XYZVSEPTKOAAPV-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- DIGVGLBAADTVFW-UHFFFAOYSA-N OC1=CC(C)=CC=C1C1=NNC(=O)CC1 Chemical compound OC1=CC(C)=CC=C1C1=NNC(=O)CC1 DIGVGLBAADTVFW-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- CYKLGTUKGYURDP-UHFFFAOYSA-L copper;hydrogen sulfate;hydroxide Chemical compound O.[Cu+2].[O-]S([O-])(=O)=O CYKLGTUKGYURDP-UHFFFAOYSA-L 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- OSAOIDIGMBDXED-UHFFFAOYSA-N cyclohexyloxybenzene Chemical compound C1CCCCC1OC1=CC=CC=C1 OSAOIDIGMBDXED-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UROYYJZSTVLYKU-UHFFFAOYSA-N hydrazine;prop-2-enoic acid Chemical compound [NH3+]N.[O-]C(=O)C=C UROYYJZSTVLYKU-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- WVLOAJPINXKMAW-UHFFFAOYSA-N methyl 4-(4-fluorophenyl)-4-oxobutanoate Chemical compound COC(=O)CCC(=O)C1=CC=C(F)C=C1 WVLOAJPINXKMAW-UHFFFAOYSA-N 0.000 description 1
- VMGCRNNKDBFNLI-UHFFFAOYSA-N methyl 4-(4-methoxyphenyl)-4-oxobutanoate Chemical compound COC(=O)CCC(=O)C1=CC=C(OC)C=C1 VMGCRNNKDBFNLI-UHFFFAOYSA-N 0.000 description 1
- ARSJCTQJRGZKFW-UHFFFAOYSA-N n-[2-methoxy-5-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]acetamide Chemical compound C1=C(NC(C)=O)C(OC)=CC=C1C1=NNC(=O)CC1 ARSJCTQJRGZKFW-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- VUNXBQRNMNVUMV-UHFFFAOYSA-N phenyl(piperazin-1-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCNCC1 VUNXBQRNMNVUMV-UHFFFAOYSA-N 0.000 description 1
- RGVBYMSUVGONHN-UHFFFAOYSA-N piperazin-2-ylidenemethanone Chemical compound O=C=C1CNCCN1 RGVBYMSUVGONHN-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Earth Drilling (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB508271A GB1383906A (en) | 1971-02-22 | 1971-02-22 | Pyridazinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2207517A1 true DE2207517A1 (de) | 1972-12-14 |
Family
ID=9789426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722207517 Pending DE2207517A1 (de) | 1971-02-22 | 1972-02-17 | Pyridazinone, Verfahren zu ihrer Herstellung und diese Verbindungen ent haltende Arzneipraparate |
Country Status (15)
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3975388A (en) * | 1971-02-22 | 1976-08-17 | Bdh Pharmaceuticals Limited | Pyridazinones |
| DE2640806A1 (de) * | 1975-09-11 | 1977-03-24 | Sankyo Co | Landwirtschaftliche fungizide zusammensetzungen und pyridazinon-derivate |
| EP0010156A1 (de) * | 1978-10-19 | 1980-04-30 | MERCK PATENT GmbH | 6-Arylpyridazin-3-one, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung |
| US4271163A (en) | 1978-12-16 | 1981-06-02 | Basf Aktiengesellschaft | Novel 3,4-diaza-bicyclo[4.1.0]hept-2-en-5-ones, their preparation, and therapeutic agents containing these compounds |
| EP0059688A1 (de) * | 1981-03-04 | 1982-09-08 | Ciba-Geigy Ag | Pyridazinone, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen und deren Verwendung |
| US4528371A (en) * | 1982-06-24 | 1985-07-09 | Smith Kline & French Laboratories Limited | Process for preparing 6-(2-hydroxyphenyl)-3-pyridazinone |
| EP0172141A1 (de) * | 1984-08-17 | 1986-02-19 | Ciba-Geigy Ag | Substituierte Pyridazinone, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen und deren Verwendung |
| EP0180542A3 (en) * | 1984-10-23 | 1987-04-08 | Ciba-Geigy Ag | alkyl substituted pyridazinones, processes for producing them, pharmaceutical preparations containing these compounds, and the use thereof |
| EP0327800A3 (en) * | 1988-02-12 | 1990-04-11 | Heumann Pharma Gmbh & Co | 6-phenyldihydro-3(2h)-pyridazinones, process for their preparation and medicines containing these compounds |
| EP0339208B1 (de) * | 1988-04-26 | 1996-02-07 | HEUMANN PHARMA GMBH & CO | 6-Oxo-pyridazinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1488330A (en) * | 1973-12-19 | 1977-10-12 | Smith Kline French Lab | Dihydropyridazinones |
| US4011321A (en) * | 1973-12-19 | 1977-03-08 | Smith Kline & French Laboratories Limited | Pharmaceutical compositions and methods of inhibiting β-adrenergic receptors |
| DE3130252A1 (de) * | 1981-07-31 | 1983-02-17 | A. Nattermann & Cie GmbH, 5000 Köln | 6-(5-((omega)-(1-imidazolyl)-alkyl)-thien-2-yl)-3-oxo-2,3,4,5-tetrahydro-pyridazine und deren saeureadditionssalze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3130251A1 (de) * | 1981-07-31 | 1983-02-17 | A. Nattermann & Cie GmbH, 5000 Köln | 6-(4-((omega)-(1-imidazolyl)-alkyl)-phenyl)-3-oxo -2,3,4,5-tetrahydro-pyridazine und deren saeureadditionssalze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| HU190412B (en) * | 1981-09-17 | 1986-09-29 | Warner-Lambert Co,Us | Process for producing substituted 4,5-dihiydro-6-bracket-substituted-bracket closed-phenyl-3-bracket-2h-bracket closed-pyridazinones and 6-bracket-substituted-bracket closed-phenyl-3-bracket-2h-bracket closed-pyridazinones |
| JPS6193169A (ja) * | 1984-10-12 | 1986-05-12 | Sankyo Co Ltd | ピリダジノン誘導体及びその製法 |
| JO2972B1 (en) | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
| AU2008258549B2 (en) | 2007-06-08 | 2013-11-14 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
| CA2687918C (en) | 2007-06-08 | 2016-11-08 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
| JP5385263B2 (ja) | 2007-06-08 | 2014-01-08 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ピペリジン／ピペラジン誘導体 |
| PE20140572A1 (es) | 2008-06-05 | 2014-05-16 | Janssen Pharmaceutica Nv | Combinaciones de drogas que comprenden un inhibidor de dgat y un agonista de ppar |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670043C3 (de) * | 1966-01-07 | 1975-05-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 3-(Aminophenyl)-pyridazon-(6)-derivaten |
-
1971
- 1971-02-22 GB GB508271A patent/GB1383906A/en not_active Expired
-
1972
- 1972-02-04 IE IE138/72A patent/IE36062B1/xx unknown
- 1972-02-07 IL IL38705A patent/IL38705A/en unknown
- 1972-02-07 ZA ZA720784A patent/ZA72784B/xx unknown
- 1972-02-11 AU AU38911/72A patent/AU465740B2/en not_active Expired
- 1972-02-15 CA CA134,888A patent/CA987322A/en not_active Expired
- 1972-02-15 BE BE779390A patent/BE779390A/xx unknown
- 1972-02-17 DE DE19722207517 patent/DE2207517A1/de active Pending
- 1972-02-17 ES ES399863A patent/ES399863A1/es not_active Expired
- 1972-02-21 FR FR7205751A patent/FR2126247B1/fr not_active Expired
- 1972-02-21 NO NO520/72A patent/NO136045C/no unknown
- 1972-02-21 SE SE7202096A patent/SE405599B/xx unknown
- 1972-02-21 AT AT138072A patent/AT313289B/de not_active IP Right Cessation
- 1972-02-22 NL NL7202336A patent/NL7202336A/xx not_active Application Discontinuation
- 1972-02-22 CH CH250172A patent/CH573921A5/xx not_active IP Right Cessation
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3975388A (en) * | 1971-02-22 | 1976-08-17 | Bdh Pharmaceuticals Limited | Pyridazinones |
| DE2640806A1 (de) * | 1975-09-11 | 1977-03-24 | Sankyo Co | Landwirtschaftliche fungizide zusammensetzungen und pyridazinon-derivate |
| EP0010156A1 (de) * | 1978-10-19 | 1980-04-30 | MERCK PATENT GmbH | 6-Arylpyridazin-3-one, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung |
| US4271163A (en) | 1978-12-16 | 1981-06-02 | Basf Aktiengesellschaft | Novel 3,4-diaza-bicyclo[4.1.0]hept-2-en-5-ones, their preparation, and therapeutic agents containing these compounds |
| EP0059688A1 (de) * | 1981-03-04 | 1982-09-08 | Ciba-Geigy Ag | Pyridazinone, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen und deren Verwendung |
| US4613599A (en) * | 1981-03-04 | 1986-09-23 | Ciba-Geigy Corporation | Method of treating thrombotic disease with pyridazinones |
| US4528371A (en) * | 1982-06-24 | 1985-07-09 | Smith Kline & French Laboratories Limited | Process for preparing 6-(2-hydroxyphenyl)-3-pyridazinone |
| EP0172141A1 (de) * | 1984-08-17 | 1986-02-19 | Ciba-Geigy Ag | Substituierte Pyridazinone, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen und deren Verwendung |
| EP0180542A3 (en) * | 1984-10-23 | 1987-04-08 | Ciba-Geigy Ag | alkyl substituted pyridazinones, processes for producing them, pharmaceutical preparations containing these compounds, and the use thereof |
| EP0327800A3 (en) * | 1988-02-12 | 1990-04-11 | Heumann Pharma Gmbh & Co | 6-phenyldihydro-3(2h)-pyridazinones, process for their preparation and medicines containing these compounds |
| US4954501A (en) * | 1988-02-12 | 1990-09-04 | Heumann Pharma Gmbh & Co. | Piperazine substituted 6-phenyldihydro-3(2H)-pyridazinones, and pharmaceutical preparations containing these |
| EP0339208B1 (de) * | 1988-04-26 | 1996-02-07 | HEUMANN PHARMA GMBH & CO | 6-Oxo-pyridazinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7202336A (enrdf_load_stackoverflow) | 1972-08-24 |
| AU3891172A (en) | 1973-08-16 |
| ZA72784B (en) | 1972-10-25 |
| IE36062B1 (en) | 1976-08-04 |
| GB1383906A (en) | 1974-02-12 |
| IL38705A (en) | 1976-08-31 |
| FR2126247B1 (enrdf_load_stackoverflow) | 1975-08-01 |
| ES399863A1 (es) | 1975-06-16 |
| IE36062L (en) | 1972-08-22 |
| AU465740B2 (en) | 1975-10-09 |
| IL38705A0 (en) | 1972-04-27 |
| CA987322A (en) | 1976-04-13 |
| BE779390A (fr) | 1972-08-16 |
| AT313289B (de) | 1974-02-11 |
| NO136045B (enrdf_load_stackoverflow) | 1977-04-04 |
| FR2126247A1 (enrdf_load_stackoverflow) | 1972-10-06 |
| NO136045C (no) | 1977-07-13 |
| SE405599B (sv) | 1978-12-18 |
| CH573921A5 (enrdf_load_stackoverflow) | 1976-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |