NO134212B - - Google Patents
Download PDFInfo
- 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
- DQZSTRARXNLNND-UHFFFAOYSA-N 1-n,1-n-dibutylbenzene-1,2,4-triamine Chemical compound CCCCN(CCCC)C1=CC=C(N)C=C1N DQZSTRARXNLNND-UHFFFAOYSA-N 0.000 description 1
- AHABMLPWPUZVOI-UHFFFAOYSA-N 1-n,1-n-diethylbenzene-1,2,4-triamine Chemical compound CCN(CC)C1=CC=C(N)C=C1N AHABMLPWPUZVOI-UHFFFAOYSA-N 0.000 description 1
- KCHNFJBUYMAXKH-UHFFFAOYSA-N 10-chloro-4,6-dioxo-1,9-dihydropyrido[3,2-g]quinoline-2,8-dicarboxylic acid Chemical compound ClC1=C2NC(C(=O)O)=CC(=O)C2=CC2=C1NC(C(O)=O)=CC2=O KCHNFJBUYMAXKH-UHFFFAOYSA-N 0.000 description 1
- GZVVXXLYQIFVCA-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=CC=C1N GZVVXXLYQIFVCA-UHFFFAOYSA-N 0.000 description 1
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- DGICDPQSVNVKIR-UHFFFAOYSA-N 2,4-dinitro-1-octylbenzene Chemical compound CCCCCCCCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O DGICDPQSVNVKIR-UHFFFAOYSA-N 0.000 description 1
- IKIPEUVCMKGZCA-UHFFFAOYSA-N 2,4-dinitro-1-propoxybenzene Chemical compound CCCOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O IKIPEUVCMKGZCA-UHFFFAOYSA-N 0.000 description 1
- YIOJWIJUSHUFKB-UHFFFAOYSA-N 2,4-dinitro-1-propylbenzene Chemical compound CCCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YIOJWIJUSHUFKB-UHFFFAOYSA-N 0.000 description 1
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- SWSUYTXURSMQSX-UHFFFAOYSA-N 2-(2,4-dinitrophenyl)azepane Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1C1NCCCCC1 SWSUYTXURSMQSX-UHFFFAOYSA-N 0.000 description 1
- ZQQOGBKIFPCFMJ-UHFFFAOYSA-N 2-(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C(F)(F)F)=C1 ZQQOGBKIFPCFMJ-UHFFFAOYSA-N 0.000 description 1
- NGULVTOQNLILMZ-UHFFFAOYSA-N 2-bromobenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(Br)=C1 NGULVTOQNLILMZ-UHFFFAOYSA-N 0.000 description 1
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 1
- LKGQTURGJNTDLR-UHFFFAOYSA-N 2-chlorobenzene-1,3-diamine Chemical compound NC1=CC=CC(N)=C1Cl LKGQTURGJNTDLR-UHFFFAOYSA-N 0.000 description 1
- WIXYRHJBVVYZRW-UHFFFAOYSA-N 3,6,9-trimethyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=C(C)C(=O)C2=C1C(C)=CC1=C2NC(C(O)=O)=C(C)C1=O WIXYRHJBVVYZRW-UHFFFAOYSA-N 0.000 description 1
- CMYLSYFQFPRQHM-UHFFFAOYSA-N 4,10-dioxo-6-piperidin-1-yl-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(=O)O)=CC(=O)C(C2=C(C(C=C(N2)C(O)=O)=O)C=2)=C1C=2N1CCCCC1 CMYLSYFQFPRQHM-UHFFFAOYSA-N 0.000 description 1
- OALULMCWRZKKEG-UHFFFAOYSA-N 4,10-dioxo-6-propoxy-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(OCCC)=CC1=C2NC(C(O)=O)=CC1=O OALULMCWRZKKEG-UHFFFAOYSA-N 0.000 description 1
- HLHDKBBKWGRDQE-UHFFFAOYSA-N 4,10-dioxo-6-propyl-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(CCC)=CC1=C2NC(C(O)=O)=CC1=O HLHDKBBKWGRDQE-UHFFFAOYSA-N 0.000 description 1
- YCGSSUNOPFLMHU-UHFFFAOYSA-N 4,10-dioxo-6-propyl-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid tetrahydrate Chemical compound O.O.O.O.C(CC)C=1C=C2C(=CC(=NC2=C2C(=CC(=NC12)C(=O)O)O)C(=O)O)O YCGSSUNOPFLMHU-UHFFFAOYSA-N 0.000 description 1
- VSWLOYIXJMPLNV-UHFFFAOYSA-N 4,5-dimethylbenzene-1,3-diamine Chemical compound CC1=CC(N)=CC(N)=C1C VSWLOYIXJMPLNV-UHFFFAOYSA-N 0.000 description 1
- 150000005051 4,7-phenanthrolines Chemical class 0.000 description 1
- CCUBIWLEWDPZCT-UHFFFAOYSA-N 4-(azepan-2-yl)benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1C1NCCCCC1 CCUBIWLEWDPZCT-UHFFFAOYSA-N 0.000 description 1
- ZWUBBMDHSZDNTA-UHFFFAOYSA-N 4-Chloro-meta-phenylenediamine Chemical compound NC1=CC=C(Cl)C(N)=C1 ZWUBBMDHSZDNTA-UHFFFAOYSA-N 0.000 description 1
- HQDCQNCMUSAKQU-UHFFFAOYSA-N 4-bromobenzene-1,3-diamine Chemical compound NC1=CC=C(Br)C(N)=C1 HQDCQNCMUSAKQU-UHFFFAOYSA-N 0.000 description 1
- GWOGHQQWWPEYCT-UHFFFAOYSA-N 4-butan-2-ylbenzene-1,3-diamine Chemical compound CCC(C)C1=CC=C(N)C=C1N GWOGHQQWWPEYCT-UHFFFAOYSA-N 0.000 description 1
- UJJYQPHAQSUZFP-UHFFFAOYSA-N 4-cyclohexylbenzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1C1CCCCC1 UJJYQPHAQSUZFP-UHFFFAOYSA-N 0.000 description 1
- NQHVJMJEWQQXBS-UHFFFAOYSA-N 4-ethoxybenzene-1,3-diamine Chemical compound CCOC1=CC=C(N)C=C1N NQHVJMJEWQQXBS-UHFFFAOYSA-N 0.000 description 1
- PTMVFRKAMOUORT-UHFFFAOYSA-N 4-ethylbenzene-1,3-diamine Chemical compound CCC1=CC=C(N)C=C1N PTMVFRKAMOUORT-UHFFFAOYSA-N 0.000 description 1
- JKBOHOMWHVBASQ-UHFFFAOYSA-N 4-hexylbenzene-1,3-diamine Chemical compound CCCCCCC1=CC=C(N)C=C1N JKBOHOMWHVBASQ-UHFFFAOYSA-N 0.000 description 1
- 150000004331 4-hydroxyquinolines Chemical class 0.000 description 1
- ABQAWYPFZVJRGM-UHFFFAOYSA-N 4-phenoxybenzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1OC1=CC=CC=C1 ABQAWYPFZVJRGM-UHFFFAOYSA-N 0.000 description 1
- UNBADGOPDIOVNX-UHFFFAOYSA-N 4-piperidin-1-ylbenzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1N1CCCCC1 UNBADGOPDIOVNX-UHFFFAOYSA-N 0.000 description 1
- IPDXWXPSCKSIII-UHFFFAOYSA-N 4-propan-2-ylbenzene-1,3-diamine Chemical compound CC(C)C1=CC=C(N)C=C1N IPDXWXPSCKSIII-UHFFFAOYSA-N 0.000 description 1
- JFQJDZQPICZGJF-UHFFFAOYSA-N 4-tert-butylbenzene-1,3-diamine Chemical compound CC(C)(C)C1=CC=C(N)C=C1N JFQJDZQPICZGJF-UHFFFAOYSA-N 0.000 description 1
- VWTJIEGEYLMQHN-UHFFFAOYSA-N 5,10-dimethyl-4,9-dioxo-1,6-dihydropyrido[2,3-g]quinoline-2,7-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(C)=C1C(=O)C=C(C(O)=O)NC1=C2C VWTJIEGEYLMQHN-UHFFFAOYSA-N 0.000 description 1
- LMFYXZLOUIMKRK-UHFFFAOYSA-N 5,6-dimethyl-1,10-dioxo-4,7-dihydro-4,7-phenanthroline-3,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(C)=C(C)C1=C2C(=O)C=C(C(O)=O)N1 LMFYXZLOUIMKRK-UHFFFAOYSA-N 0.000 description 1
- DAAFHXRQEYCQRY-UHFFFAOYSA-N 5,6-dimethyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(C)=C(C)C1=C2NC(C(O)=O)=CC1=O DAAFHXRQEYCQRY-UHFFFAOYSA-N 0.000 description 1
- WJGOQDMPYGKITM-UHFFFAOYSA-N 5-chloro-1,10-dioxo-4,7-dihydro-4,7-phenanthroline-3,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(Cl)=CC1=C2C(=O)C=C(C(=O)O)N1 WJGOQDMPYGKITM-UHFFFAOYSA-N 0.000 description 1
- ZCZDEAWPJJLPGN-UHFFFAOYSA-N 5-methyl-1,10-dioxo-4,7-dihydro-4,7-phenanthroline-3,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(C)=CC1=C2C(=O)C=C(C(O)=O)N1 ZCZDEAWPJJLPGN-UHFFFAOYSA-N 0.000 description 1
- MYZYZAQWHDUIDX-UHFFFAOYSA-N 6-(azepan-1-yl)-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(=O)O)=CC(=O)C(C2=C(C(C=C(N2)C(O)=O)=O)C=2)=C1C=2N1CCCCCC1 MYZYZAQWHDUIDX-UHFFFAOYSA-N 0.000 description 1
- CVZDMARRKWJQAD-UHFFFAOYSA-N 6-bromo-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound BrC1=CC(C(C=C(N2)C(O)=O)=O)=C2C2=C1NC(C(=O)O)=CC2=O CVZDMARRKWJQAD-UHFFFAOYSA-N 0.000 description 1
- VTTPBWBUXPTNGP-UHFFFAOYSA-N 6-butan-2-yl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound C(C)(CC)C=1C=C2C(=CC(=NC2=C2C(=CC(=NC12)C(=O)O)O)C(=O)O)O VTTPBWBUXPTNGP-UHFFFAOYSA-N 0.000 description 1
- VRVXQBJZZIRSRW-UHFFFAOYSA-N 6-chloro-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound ClC1=CC(C(C=C(N2)C(O)=O)=O)=C2C2=C1NC(C(=O)O)=CC2=O VRVXQBJZZIRSRW-UHFFFAOYSA-N 0.000 description 1
- GYHUPYIPGCTCEX-UHFFFAOYSA-N 6-ethoxy-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(OCC)=CC1=C2NC(C(O)=O)=CC1=O GYHUPYIPGCTCEX-UHFFFAOYSA-N 0.000 description 1
- FYWCGZVZFSJKER-UHFFFAOYSA-N 6-ethyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(CC)=CC1=C2NC(C(O)=O)=CC1=O FYWCGZVZFSJKER-UHFFFAOYSA-N 0.000 description 1
- MWZCYMSZUWCBPM-UHFFFAOYSA-N 6-fluoro-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound FC1=CC(C(C=C(N2)C(O)=O)=O)=C2C2=C1NC(C(=O)O)=CC2=O MWZCYMSZUWCBPM-UHFFFAOYSA-N 0.000 description 1
- VIOINCJGSSGNRC-UHFFFAOYSA-N 6-heptyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(CCCCCCC)=CC1=C2NC(C(O)=O)=CC1=O VIOINCJGSSGNRC-UHFFFAOYSA-N 0.000 description 1
- AYCQUZQPYRMKNQ-UHFFFAOYSA-N 6-hexyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(CCCCCC)=CC1=C2NC(C(O)=O)=CC1=O AYCQUZQPYRMKNQ-UHFFFAOYSA-N 0.000 description 1
- DZHARTIGFVDNIY-UHFFFAOYSA-N 6-methoxy-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(OC)=CC1=C2NC(C(O)=O)=CC1=O DZHARTIGFVDNIY-UHFFFAOYSA-N 0.000 description 1
- KHTITMNSGXVYDK-UHFFFAOYSA-N 6-morpholin-4-yl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(=O)O)=CC(=O)C(C2=C(C(C=C(N2)C(O)=O)=O)C=2)=C1C=2N1CCOCC1 KHTITMNSGXVYDK-UHFFFAOYSA-N 0.000 description 1
- SWIBCPLUCWYJGO-UHFFFAOYSA-N 6-tert-butyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid Chemical compound N1C(C(O)=O)=CC(=O)C2=C1C(C(C)(C)C)=CC1=C2NC(C(O)=O)=CC1=O SWIBCPLUCWYJGO-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 241000588832 Bordetella pertussis Species 0.000 description 1
- RZZPDXZPRHQOCG-OJAKKHQRSA-O CDP-choline(1+) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-O 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 229960000711 alprostadil Drugs 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- JDXYSCUOABNLIR-UHFFFAOYSA-N diethyl 2-oxobutanedioate Chemical compound CCOC(=O)CC(=O)C(=O)OCC JDXYSCUOABNLIR-UHFFFAOYSA-N 0.000 description 1
- NGRAIMFUWGFAEM-UHFFFAOYSA-N diethyl 2-oxopentanedioate Chemical compound CCOC(=O)CCC(=O)C(=O)OCC NGRAIMFUWGFAEM-UHFFFAOYSA-N 0.000 description 1
- WCLNXQPVBPGPCH-UHFFFAOYSA-N diethyl 4,10-dioxo-6-phenoxy-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound N1C(C(=O)OCC)=CC(=O)C(C2=C(C(C=C(N2)C(=O)OCC)=O)C=2)=C1C=2OC1=CC=CC=C1 WCLNXQPVBPGPCH-UHFFFAOYSA-N 0.000 description 1
- LQBYKNSTPBXFIT-UHFFFAOYSA-N diethyl 4,10-dioxo-6-phenoxy-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate hydrate Chemical compound O.C(C)OC(=O)C1=NC2=C3C(=CC(=NC3=C(C=C2C(=C1)O)OC1=CC=CC=C1)C(=O)OCC)O LQBYKNSTPBXFIT-UHFFFAOYSA-N 0.000 description 1
- BLXCIBDEYGHDTH-UHFFFAOYSA-N diethyl 4,10-dioxo-6-propyl-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound N1C(C(=O)OCC)=CC(=O)C2=C1C(CCC)=CC1=C2NC(C(=O)OCC)=CC1=O BLXCIBDEYGHDTH-UHFFFAOYSA-N 0.000 description 1
- SPHXTOXHDAZMPZ-UHFFFAOYSA-N diethyl 6-chloro-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound ClC1=CC(C(C=C(N2)C(=O)OCC)=O)=C2C2=C1NC(C(=O)OCC)=CC2=O SPHXTOXHDAZMPZ-UHFFFAOYSA-N 0.000 description 1
- MUIUBKDJQAGFMG-UHFFFAOYSA-N diethyl 6-ethyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound CCC1=CC(C(C=C(N2)C(=O)OCC)=O)=C2C2=C1NC(C(=O)OCC)=CC2=O MUIUBKDJQAGFMG-UHFFFAOYSA-N 0.000 description 1
- USKXMMZZMZQJSK-UHFFFAOYSA-N diethyl 6-tert-butyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylate Chemical compound CC(C)(C)C1=CC(C(C=C(N2)C(=O)OCC)=O)=C2C2=C1NC(C(=O)OCC)=CC2=O USKXMMZZMZQJSK-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940071094 diethyl oxalacetate Drugs 0.000 description 1
- NGXQWQRPDQPADW-UHFFFAOYSA-N dimethyl 10-chloro-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(Cl)=C21 NGXQWQRPDQPADW-UHFFFAOYSA-N 0.000 description 1
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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 (da) | 1976-05-24 |
NO134212C NO134212C (da) | 1976-09-01 |
Family
ID=27254567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO3633/71A NO134212C (da) | 1970-10-05 | 1971-10-04 |
Country Status (17)
Country | Link |
---|---|
US (1) | US3790577A (da) |
JP (1) | JPS557427B1 (da) |
AU (1) | AU451793B2 (da) |
BE (1) | BE773200A (da) |
CA (1) | CA995670A (da) |
CH (4) | CH583735A5 (da) |
DD (1) | DD98931A5 (da) |
DE (1) | DE2149692A1 (da) |
ES (1) | ES395714A1 (da) |
FR (1) | FR2110216B1 (da) |
HU (1) | HU163114B (da) |
IE (1) | IE35639B1 (da) |
IL (1) | IL37749A (da) |
KE (1) | KE2611A (da) |
NL (1) | NL7113638A (da) |
NO (1) | NO134212C (da) |
SE (1) | SE394678B (da) |
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 (da) * | 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 |
AU4488989A (en) * | 1988-11-15 | 1990-06-12 | Upjohn Company, The | Phenanthrolinedicarboxylate esters, 4-aminoquinoline and isoquinoline derivatives as inhibitors of hiv reverse transcriptase |
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 |
US5057515A (en) * | 1989-07-24 | 1991-10-15 | Eli Lilly And Company | Method for agonizing a dopamine receptor |
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 US US00180233A patent/US3790577A/en not_active Expired - Lifetime
- 1971-09-13 IE IE1159/71A patent/IE35639B1/xx unknown
- 1971-09-13 CA CA122,706A patent/CA995670A/en not_active Expired
- 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 CH264275A patent/CH583735A5/xx not_active IP Right Cessation
- 1971-10-04 CH CH264175A patent/CH579085A5/xx unknown
- 1971-10-04 NO NO3633/71A patent/NO134212C/no unknown
- 1971-10-04 CH CH264075A patent/CH572928A5/xx not_active IP Right Cessation
- 1971-10-04 CH CH1440271A patent/CH572927A5/xx not_active IP Right Cessation
- 1971-10-04 SE SE7112516A patent/SE394678B/xx unknown
- 1971-10-04 FR FR7135693A patent/FR2110216B1/fr not_active Expired
- 1971-10-05 AU AU34195/71A patent/AU451793B2/en not_active Expired
- 1971-10-05 JP JP7824071A patent/JPS557427B1/ja active Pending
- 1971-10-05 ES ES395714A patent/ES395714A1/es not_active Expired
- 1971-10-05 NL NL7113638A patent/NL7113638A/xx unknown
- 1971-10-05 DE DE19712149692 patent/DE2149692A1/de active Pending
-
1976
- 1976-03-15 KE KE2611*UA patent/KE2611A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
KE2611A (en) | 1976-04-15 |
CA995670A (en) | 1976-08-24 |
NL7113638A (da) | 1972-04-07 |
SE394678B (sv) | 1977-07-04 |
BE773200A (fr) | 1972-03-28 |
IE35639B1 (en) | 1976-04-14 |
FR2110216A1 (da) | 1972-06-02 |
NO134212C (da) | 1976-09-01 |
ES395714A1 (es) | 1974-08-16 |
US3790577A (en) | 1974-02-05 |
CH579085A5 (da) | 1976-08-31 |
DD98931A5 (da) | 1973-07-12 |
FR2110216B1 (da) | 1975-04-18 |
HU163114B (da) | 1973-06-28 |
CH572928A5 (da) | 1976-02-27 |
IL37749A (en) | 1974-10-22 |
AU451793B2 (en) | 1974-08-15 |
IE35639L (en) | 1972-04-05 |
AU3419571A (en) | 1973-04-12 |
CH583735A5 (da) | 1977-01-14 |
JPS557427B1 (da) | 1980-02-25 |
CH572927A5 (da) | 1976-02-27 |
DE2149692A1 (de) | 1972-04-06 |
IL37749A0 (en) | 1971-11-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO134212B (da) | ||
US3755340A (en) | Amino derivatives of pyrazolopyridine carboxylic acids and esters | |
Adams et al. | Ultraviolet spectra and structures of the pyrido [1, 2-a] pyrimidones | |
KR880002232B1 (ko) | 퀴놀린 유도체와 그 염의 제조방법 | |
NO170335B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive diazabicykloalkyl-kinolon-karboksylsyrer | |
US3484445A (en) | Derivatives of chromone-2-carboxylic acid | |
NO154522B (no) | Analogifremgangsmaate for fremstilling av terapeutisk virksomme kinolinderivater. | |
EP0104522B1 (en) | New pyrazolo(3,4-b)pyridine derivatives and process for producing them | |
NO151287B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive 9-hydrazono-6,7,8,9-tetrahydro-4h-pyrido(1,2-a)-pyrimidinderivater | |
Althuis et al. | Structure-activity relationships in a series of novel 3, 4-dihydro-4-oxopyrimido [4, 5-b] quinoline-2-carboxylic acid antiallergy agents | |
EP0156559A2 (en) | 8-Substituted guanine derivatives | |
SU416946A3 (ru) | СПОСОБ ПОЛУЧЕНИЯ 1-БЕНЗОТИЕНО-[2,3-йг]-ПИРИМИДИНОВ | |
US4996213A (en) | Derivatives of 4-amino 3-carboxy naphthyridines and their pharmaceutical compositions | |
Suzuki et al. | Synthesis of antimicrobial agents. IV. Synthesis and antimicrobial activities of imidazo [4, 5-b][1, 8] naphthyridine derivatives | |
Hall et al. | Quinoline derivatives as antiallergy agents. 2. Fused-ring quinaldic acids | |
CA1173445A (en) | Quinolone derivatives and their use as pharmaceuticals | |
US4048184A (en) | 6-Phenyl-2H-pyrazolo[3,4-b]pyridines | |
US3873538A (en) | Amino-9,10-dihydro-9,10-dioxo-2-anthroic acids | |
US4192944A (en) | Optionally substituted 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-N-(1H-tetrazol-4-yl)carboxamides and their use as antiallergy agents | |
CA1154766A (en) | Antiallergic nitrogen bridgehead compounds and process for the preparation thereof | |
NO162188B (no) | Analogifremgangsm te for fremstilling av terapeutisk aktive imidazokinoliner. | |
JPS6045199B2 (ja) | 新規なイミダゾベンゾオキサジン及びそれらを含む製薬組成物 | |
US3976651A (en) | 7-Hydroxy-benzo[ij]quinolizine-2-carboxylic acids, intermediates, and a method for their production | |
US3969463A (en) | N-methylene malonate of tetrahydroquinoline and derivatives thereof | |
US3974161A (en) | Fused pyrimidin-4(3H)-ones as antiallergy agents |