NO134212B - - Google Patents
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- Publication number
- NO134212B NO134212B NO3633/71A NO363371A NO134212B NO 134212 B NO134212 B NO 134212B NO 3633/71 A NO3633/71 A NO 3633/71A NO 363371 A NO363371 A NO 363371A NO 134212 B NO134212 B NO 134212B
- Authority
- NO
- Norway
- Prior art keywords
- radical
- formula
- dihydroxy
- phenanthroline
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 38
- -1 C11-alkyl radical Chemical class 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 20
- 231100000252 nontoxic Toxicity 0.000 claims description 15
- 230000003000 nontoxic effect Effects 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 4
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 3
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
- RAEIRHYFVKEMOH-UHFFFAOYSA-N 4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound C1=CC(C(C=C(N2)C(O)=O)=O)=C2C2=C1NC(C(=O)O)=CC2=O RAEIRHYFVKEMOH-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 150000000475 acetylene derivatives Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- KALHHNYDHPEWLZ-UHFFFAOYSA-N dimethyl 4,9-dioxo-1,6-dihydropyrido[2,3-g]quinoline-2,7-dicarboxylate Chemical compound N1=C(C(=O)OC)C=C(O)C2=CC3=NC(C(=O)OC)=CC(O)=C3C=C21 KALHHNYDHPEWLZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 150000003227 pyridoxines Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 43
- 239000000243 solution Substances 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- 239000007787 solid Substances 0.000 description 19
- 239000007858 starting material Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 13
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- KJVCRAMHOORMSK-UHFFFAOYSA-N 4-butylbenzene-1,3-diamine Chemical compound CCCCC1=CC=C(N)C=C1N KJVCRAMHOORMSK-UHFFFAOYSA-N 0.000 description 7
- AKDKGRYGAUKIPE-UHFFFAOYSA-N 6-methyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(C)=CC1=C2NC(C(O)=O)=CC1=O AKDKGRYGAUKIPE-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 6
- OZKOMUDCMCEDTM-UHFFFAOYSA-N 1,7-phenanthroline Chemical class C1=CC=C2C3=NC=CC=C3C=CC2=N1 OZKOMUDCMCEDTM-UHFFFAOYSA-N 0.000 description 6
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- JDDYUESEKSVVER-UHFFFAOYSA-N diethyl 6-methyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound CC1=CC(C(C=C(N2)C(=O)OCC)=O)=C2C2=C1NC(C(=O)OCC)=CC2=O JDDYUESEKSVVER-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- ZRLMFBOSLNCGQG-UHFFFAOYSA-N 1-butyl-2,4-dinitrobenzene Chemical compound CCCCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O ZRLMFBOSLNCGQG-UHFFFAOYSA-N 0.000 description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 208000006673 asthma Diseases 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 229940093475 2-ethoxyethanol Drugs 0.000 description 3
- UQEWLKOCZFCMBK-UHFFFAOYSA-N 4-heptylbenzene-1,3-diamine Chemical compound CCCCCCCC1=CC=C(N)C=C1N UQEWLKOCZFCMBK-UHFFFAOYSA-N 0.000 description 3
- JCYCUIPSHRUWLN-UHFFFAOYSA-N 4-morpholin-4-ylbenzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1N1CCOCC1 JCYCUIPSHRUWLN-UHFFFAOYSA-N 0.000 description 3
- ZYSBMNFEPNFBGJ-UHFFFAOYSA-N 4-octylbenzene-1,3-diamine Chemical compound CCCCCCCCC1=CC=C(N)C=C1N ZYSBMNFEPNFBGJ-UHFFFAOYSA-N 0.000 description 3
- ZGFLEVSMIQQQAJ-UHFFFAOYSA-N 4-pentylbenzene-1,3-diamine Chemical compound CCCCCC1=CC=C(N)C=C1N ZGFLEVSMIQQQAJ-UHFFFAOYSA-N 0.000 description 3
- FJBQGRKYDQRFQC-UHFFFAOYSA-N 4-propoxybenzene-1,3-diamine Chemical compound CCCOC1=CC=C(N)C=C1N FJBQGRKYDQRFQC-UHFFFAOYSA-N 0.000 description 3
- BQVIONBNDNFCCP-UHFFFAOYSA-N 6-butyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(CCCC)=CC1=C2NC(C(O)=O)=CC1=O BQVIONBNDNFCCP-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- VXWFOIZDEAEGMP-UHFFFAOYSA-N dimethyl 3,6,9-trimethyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound N1C(C(=O)OC)=C(C)C(=O)C=2C1=C1C(=O)C(C)=C(C(=O)OC)NC1=C(C)C=2 VXWFOIZDEAEGMP-UHFFFAOYSA-N 0.000 description 3
- QYKUISHVJGBJIN-UHFFFAOYSA-N dimethyl 5-methyl-1,10-dioxo-4,7-dihydro-4,7-phenanthroline-3,8-dicarboxylate Chemical compound N1C(C(=O)OC)=CC(=O)C2=C1C(C)=CC1=C2C(=O)C=C(C(=O)OC)N1 QYKUISHVJGBJIN-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 150000005042 1,7-phenanthrolines Chemical class 0.000 description 2
- WMDUZUGCLVMSFY-UHFFFAOYSA-N 1-hexyl-2,4-dinitrobenzene Chemical compound CCCCCCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O WMDUZUGCLVMSFY-UHFFFAOYSA-N 0.000 description 2
- BNFNUAHTWUMITD-UHFFFAOYSA-N 1-n-methyl-1-n-phenylbenzene-1,2,4-triamine Chemical compound C=1C=C(N)C=C(N)C=1N(C)C1=CC=CC=C1 BNFNUAHTWUMITD-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- WPIPMTCDVGQGPY-UHFFFAOYSA-N 2,4-dinitro-1-pentylbenzene Chemical compound CCCCCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O WPIPMTCDVGQGPY-UHFFFAOYSA-N 0.000 description 2
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 2
- BFEWBUGYJFNVPG-UHFFFAOYSA-N 4,10-dioxo-6-pentyl-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(CCCCC)=CC1=C2NC(C(O)=O)=CC1=O BFEWBUGYJFNVPG-UHFFFAOYSA-N 0.000 description 2
- QNDFYLBDUWCFJO-UHFFFAOYSA-N 4-fluorobenzene-1,3-diamine Chemical compound NC1=CC=C(F)C(N)=C1 QNDFYLBDUWCFJO-UHFFFAOYSA-N 0.000 description 2
- LMGWHMKXSXDWRB-UHFFFAOYSA-N 4-propylbenzene-1,3-diamine Chemical compound CCCC1=CC=C(N)C=C1N LMGWHMKXSXDWRB-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 2
- PYMOZXBOLWEJLH-UHFFFAOYSA-N dibutyl 6-methyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound CC1=CC(C(C=C(N2)C(=O)OCCCC)=O)=C2C2=C1NC(C(=O)OCCCC)=CC2=O PYMOZXBOLWEJLH-UHFFFAOYSA-N 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- HFHHGELBOIGGNP-UHFFFAOYSA-N dimethyl 10-methyl-4,6-dioxo-1,9-dihydropyrido[3,2-g]quinoline-2,8-dicarboxylate Chemical compound CC1=C2NC(C(=O)OC)=CC(=O)C2=CC2=C1NC(C(=O)OC)=CC2=O HFHHGELBOIGGNP-UHFFFAOYSA-N 0.000 description 2
- OSAFMLCJIGEDFW-UHFFFAOYSA-N dimethyl 4,10-dioxo-6-piperidin-1-yl-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound N1C(C(=O)OC)=CC(=O)C(C2=C(C(C=C(N2)C(=O)OC)=O)C=2)=C1C=2N1CCCCC1 OSAFMLCJIGEDFW-UHFFFAOYSA-N 0.000 description 2
- BDEMRUYEERUEOX-UHFFFAOYSA-N dimethyl 6-bromo-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound BrC1=CC(C(C=C(N2)C(=O)OC)=O)=C2C2=C1NC(C(=O)OC)=CC2=O BDEMRUYEERUEOX-UHFFFAOYSA-N 0.000 description 2
- BPESSNABBRNNIQ-UHFFFAOYSA-N dimethyl 6-butyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound N1C(C(=O)OC)=CC(=O)C2=C1C(CCCC)=CC1=C2NC(C(=O)OC)=CC1=O BPESSNABBRNNIQ-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- SMQWUBPKKHMGCW-UHFFFAOYSA-N 1,10-dioxo-4,7-dihydro-4,7-phenanthroline-3,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C=CC1=C2C(=O)C=C(C(=O)O)N1 SMQWUBPKKHMGCW-UHFFFAOYSA-N 0.000 description 1
- ZLAIXXGQYGFSNM-UHFFFAOYSA-N 1,10-dioxo-5-(trifluoromethyl)-4,7-dihydro-4,7-phenanthroline-3,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(C(F)(F)F)=CC1=C2C(=O)C=C(C(=O)O)N1 ZLAIXXGQYGFSNM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- LBNXAWYDQUGHGX-UHFFFAOYSA-N 1-Phenylheptane Chemical compound CCCCCCCC1=CC=CC=C1 LBNXAWYDQUGHGX-UHFFFAOYSA-N 0.000 description 1
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 1
- IEAAPZFWBYUTFY-UHFFFAOYSA-N 1-heptyl-2,4-dinitrobenzene Chemical compound CCCCCCCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O IEAAPZFWBYUTFY-UHFFFAOYSA-N 0.000 description 1
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- RSBRRRVOPIYVPB-UHFFFAOYSA-N dimethyl 4,9-dioxo-10-(trifluoromethyl)-1,6-dihydropyrido[2,3-g]quinoline-2,7-dicarboxylate Chemical compound N1=C(C(=O)OC)C=C(O)C2=CC3=NC(C(=O)OC)=CC(O)=C3C(C(F)(F)F)=C21 RSBRRRVOPIYVPB-UHFFFAOYSA-N 0.000 description 1
- XHSDSELGWAZDIS-UHFFFAOYSA-N dimethyl 5-bromo-1,10-dioxo-4,7-dihydro-4,7-phenanthroline-3,8-dicarboxylate Chemical compound N1C(C(=O)OC)=CC(=O)C2=C1C(Br)=CC1=C2C(=O)C=C(C(=O)OC)N1 XHSDSELGWAZDIS-UHFFFAOYSA-N 0.000 description 1
- VZLGITOTQLKUGT-UHFFFAOYSA-N dimethyl 5-chloro-1,10-dioxo-4,7-dihydro-4,7-phenanthroline-3,8-dicarboxylate Chemical compound N1C(C(=O)OC)=CC(=O)C2=C1C(Cl)=CC1=C2C(=O)C=C(C(=O)OC)N1 VZLGITOTQLKUGT-UHFFFAOYSA-N 0.000 description 1
- OUOGIRHPOQCORE-UHFFFAOYSA-N dimethyl 6-(diethylamino)-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound N1C(C(=O)OC)=CC(=O)C2=C1C(N(CC)CC)=CC1=C2NC(C(=O)OC)=CC1=O OUOGIRHPOQCORE-UHFFFAOYSA-N 0.000 description 1
- ZLFJMJWYEAOCRN-UHFFFAOYSA-N dipentyl 6-methyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound CC1=CC(C(C=C(N2)C(=O)OCCCCC)=O)=C2C2=C1NC(C(=O)OCCCCC)=CC2=O ZLFJMJWYEAOCRN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940069417 doxy Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- VQUHVWVGRKTIBH-UHFFFAOYSA-N hydron;2-methylbenzene-1,4-diamine;dichloride Chemical compound Cl.Cl.CC1=CC(N)=CC=C1N VQUHVWVGRKTIBH-UHFFFAOYSA-N 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- CYRRWDPFDBUXIP-UHFFFAOYSA-N n,n-dibutyl-2,4-dinitroaniline Chemical compound CCCCN(CCCC)C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O CYRRWDPFDBUXIP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- RFGXNUXNXWMFRQ-UHFFFAOYSA-N pyrido[3,2-g]quinoline Chemical compound N1=CC=CC2=CC3=CC=CN=C3C=C21 RFGXNUXNXWMFRQ-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940048021 sodium diethyl oxalacetate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- JPTKZRPOIUYFTM-UHFFFAOYSA-N sodium;diethyl 2-oxobutanedioate Chemical compound [Na+].CCOC(=O)[CH-]C(=O)C(=O)OCC JPTKZRPOIUYFTM-UHFFFAOYSA-N 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4715170 | 1970-10-05 | ||
| GB5486870 | 1970-11-18 | ||
| GB509671 | 1971-02-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134212B true NO134212B (ko) | 1976-05-24 |
| NO134212C NO134212C (ko) | 1976-09-01 |
Family
ID=27254567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3633/71A NO134212C (ko) | 1970-10-05 | 1971-10-04 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3790577A (ko) |
| JP (1) | JPS557427B1 (ko) |
| AU (1) | AU451793B2 (ko) |
| BE (1) | BE773200A (ko) |
| CA (1) | CA995670A (ko) |
| CH (4) | CH579085A5 (ko) |
| DD (1) | DD98931A5 (ko) |
| DE (1) | DE2149692A1 (ko) |
| ES (1) | ES395714A1 (ko) |
| FR (1) | FR2110216B1 (ko) |
| HU (1) | HU163114B (ko) |
| IE (1) | IE35639B1 (ko) |
| IL (1) | IL37749A (ko) |
| KE (1) | KE2611A (ko) |
| NL (1) | NL7113638A (ko) |
| NO (1) | NO134212C (ko) |
| SE (1) | SE394678B (ko) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1433801A (en) * | 1973-04-16 | 1976-04-28 | Ici Ltd | Pyrido-3,2-g- quinoline derivatives |
| CA984842A (en) * | 1972-02-28 | 1976-03-02 | Charles M. Hall | 1,4,6,9-tetrahydro-4,6-dioxopyrido-(3,2-g)-quinoline-2,8-dicarboxylic acid compounds |
| ZA735221B (en) * | 1972-08-07 | 1974-07-31 | Upjohn Co | Improved dosage regimen |
| CH567557A5 (ko) * | 1972-08-09 | 1975-10-15 | Ciba Geigy Ag | |
| US3838132A (en) * | 1972-09-08 | 1974-09-24 | C Hall | 1,4,7,10-tetrahydro-1,7-dioxoquino(8,7-h)quinoline-3,9-dicarboxylate compounds |
| US3959289A (en) * | 1972-11-06 | 1976-05-25 | The Upjohn Company | Derivatives of 4,6 dioxopyrido[3,2-g]quinoline 2,8 dicarboxylic acid |
| US4156726A (en) * | 1974-12-07 | 1979-05-29 | Fisons Limited | 4-Oxo-2-carboxyl quinoline derivatives used as antiallergic compounds |
| US4126617A (en) * | 1974-12-11 | 1978-11-21 | The Upjohn Company | DI-Tham salt of 10-cl,1,4,6,9 tetrahydro-5-methyl 4,6 dioxopyrido[3,2-g]quinoline-2,8-dicarboxylate |
| GB1487535A (en) * | 1975-05-19 | 1977-10-05 | Ici Ltd | Pyridoquinolines |
| US4123536A (en) * | 1977-12-14 | 1978-10-31 | Warner-Lambert Company | Dialkyl ({[3-(alkoxycarbonyl)-1,4-dihydro-4-oxo-8-quinolinyl]amino}methylene)propanedioates |
| US4297358A (en) * | 1979-01-16 | 1981-10-27 | Ciba-Geigy Corporation | Novel 4,7-phenanthroline derivatives and pharmaceutical compositions containing them and their use |
| US4335130A (en) * | 1981-05-12 | 1982-06-15 | Morton-Norwich Products, Inc. | Antifungal composition |
| JPS629007A (ja) * | 1985-07-04 | 1987-01-17 | Jidosha Kiki Co Ltd | アクチエ−タ |
| WO1990005523A2 (en) * | 1988-11-15 | 1990-05-31 | The Upjohn Company | Phenanthrolinedicarboxylate esters, 4-aminoquinoline and isoquinoline derivatives as inhibitors of hiv reverse transcriptase |
| US5057515A (en) * | 1989-07-24 | 1991-10-15 | Eli Lilly And Company | Method for agonizing a dopamine receptor |
| US4939259A (en) * | 1989-07-24 | 1990-07-03 | Eli Lilly And Company | 2-oxo-pyrido[2,3-g]quinoline derivatives |
| US5006525A (en) * | 1989-07-24 | 1991-04-09 | Eli Lilly And Company | Dopamine agonists method |
| US4977149A (en) * | 1989-07-24 | 1990-12-11 | Eli Lilly And Company | Pyridoquinoline dopamine agonists, compositions and use |
| US5416090A (en) * | 1991-01-31 | 1995-05-16 | Eli Lilly And Company | Method of treating inflammation |
| US5994365A (en) * | 1997-02-25 | 1999-11-30 | Diazans Limited | Substituted diazaanthracene compounds having pharmaceutical utility |
| KR20100000121A (ko) * | 2008-06-24 | 2010-01-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
-
1971
- 1971-09-13 CA CA122,706A patent/CA995670A/en not_active Expired
- 1971-09-13 US US00180233A patent/US3790577A/en not_active Expired - Lifetime
- 1971-09-13 IE IE1159/71A patent/IE35639B1/xx unknown
- 1971-09-17 IL IL37749A patent/IL37749A/en unknown
- 1971-09-17 HU HUIE477A patent/HU163114B/hu unknown
- 1971-09-28 BE BE773200A patent/BE773200A/xx unknown
- 1971-10-04 DD DD158103A patent/DD98931A5/xx unknown
- 1971-10-04 CH CH264175A patent/CH579085A5/xx unknown
- 1971-10-04 NO NO3633/71A patent/NO134212C/no unknown
- 1971-10-04 FR FR7135693A patent/FR2110216B1/fr not_active Expired
- 1971-10-04 CH CH1440271A patent/CH572927A5/xx not_active IP Right Cessation
- 1971-10-04 CH CH264275A patent/CH583735A5/xx not_active IP Right Cessation
- 1971-10-04 SE SE7112516A patent/SE394678B/xx unknown
- 1971-10-04 CH CH264075A patent/CH572928A5/xx not_active IP Right Cessation
- 1971-10-05 AU AU34195/71A patent/AU451793B2/en not_active Expired
- 1971-10-05 DE DE19712149692 patent/DE2149692A1/de active Pending
- 1971-10-05 JP JP7824071A patent/JPS557427B1/ja active Pending
- 1971-10-05 NL NL7113638A patent/NL7113638A/xx unknown
- 1971-10-05 ES ES395714A patent/ES395714A1/es not_active Expired
-
1976
- 1976-03-15 KE KE2611*UA patent/KE2611A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH572928A5 (ko) | 1976-02-27 |
| CH579085A5 (ko) | 1976-08-31 |
| KE2611A (en) | 1976-04-15 |
| BE773200A (fr) | 1972-03-28 |
| IE35639L (en) | 1972-04-05 |
| IL37749A (en) | 1974-10-22 |
| CH572927A5 (ko) | 1976-02-27 |
| NL7113638A (ko) | 1972-04-07 |
| AU3419571A (en) | 1973-04-12 |
| FR2110216B1 (ko) | 1975-04-18 |
| SE394678B (sv) | 1977-07-04 |
| ES395714A1 (es) | 1974-08-16 |
| US3790577A (en) | 1974-02-05 |
| DE2149692A1 (de) | 1972-04-06 |
| IL37749A0 (en) | 1971-11-29 |
| NO134212C (ko) | 1976-09-01 |
| CA995670A (en) | 1976-08-24 |
| AU451793B2 (en) | 1974-08-15 |
| FR2110216A1 (ko) | 1972-06-02 |
| DD98931A5 (ko) | 1973-07-12 |
| IE35639B1 (en) | 1976-04-14 |
| JPS557427B1 (ko) | 1980-02-25 |
| HU163114B (ko) | 1973-06-28 |
| CH583735A5 (ko) | 1977-01-14 |
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