NO135632B - - Google Patents
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- Publication number
- NO135632B NO135632B NO4655/72A NO465572A NO135632B NO 135632 B NO135632 B NO 135632B NO 4655/72 A NO4655/72 A NO 4655/72A NO 465572 A NO465572 A NO 465572A NO 135632 B NO135632 B NO 135632B
- Authority
- NO
- Norway
- Prior art keywords
- dione
- indan
- found
- requires
- hydrochloric acid
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 16
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- -1 2-nitroindan-1,3-dione 4,5-dimethoxy-2-nitroindan-1,3-dione 5-methoxy-2-nitroindan- 1,3-dione 4-chloro-2-nitroindane-1,3-dione 5-chloro-2-nitroindane-1,3-dione 5-bromo-2-nitroindane-1,3-dione Chemical compound 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- CJGMVHVKJXBIDT-UHFFFAOYSA-N 2-nitroindene-1,3-dione Chemical compound C1=CC=C2C(=O)C([N+](=O)[O-])C(=O)C2=C1 CJGMVHVKJXBIDT-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-indandione Chemical compound C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 claims description 2
- VDSILRLWKIEHRV-UHFFFAOYSA-N 3-nitro-3h-indene-1,2-dione Chemical class C1=CC=C2C([N+](=O)[O-])C(=O)C(=O)C2=C1 VDSILRLWKIEHRV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 86
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 229910001868 water Inorganic materials 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 18
- 229910000104 sodium hydride Inorganic materials 0.000 description 17
- 238000006396 nitration reaction Methods 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- 239000002480 mineral oil Substances 0.000 description 11
- 235000010446 mineral oil Nutrition 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000006114 decarboxylation reaction Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000003512 Claisen condensation reaction Methods 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- WFFZGYRTVIPBFN-UHFFFAOYSA-N 3h-indene-1,2-dione Chemical compound C1=CC=C2C(=O)C(=O)CC2=C1 WFFZGYRTVIPBFN-UHFFFAOYSA-N 0.000 description 3
- NFKODVOKPAEECO-UHFFFAOYSA-N 4-ethoxyindene-1,3-dione Chemical compound CCOC1=CC=CC2=C1C(=O)CC2=O NFKODVOKPAEECO-UHFFFAOYSA-N 0.000 description 3
- UFFXQKZAZJAMCH-UHFFFAOYSA-N 4-fluoroindene-1,3-dione Chemical compound FC1=CC=CC2=C1C(=O)CC2=O UFFXQKZAZJAMCH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- BMODQQWZCVNPKL-UHFFFAOYSA-N dimethyl 4,5-dimethylbenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC(C)=C(C)C=C1C(=O)OC BMODQQWZCVNPKL-UHFFFAOYSA-N 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- MMNWNJDBJWFNRD-UHFFFAOYSA-N 2-nitro-5-phenylindene-1,3-dione Chemical compound C1=C2C(=O)C([N+](=O)[O-])C(=O)C2=CC=C1C1=CC=CC=C1 MMNWNJDBJWFNRD-UHFFFAOYSA-N 0.000 description 2
- VBXUUFVCIMWMSR-UHFFFAOYSA-N 2-nitrocyclopenta[b]naphthalene-1,3-dione Chemical compound C1=CC=C2C=C(C(C([N+](=O)[O-])C3=O)=O)C3=CC2=C1 VBXUUFVCIMWMSR-UHFFFAOYSA-N 0.000 description 2
- CYUJGLFOZYZGCH-UHFFFAOYSA-N 4,6-dimethyl-2-nitroindene-1,3-dione Chemical compound CC1=CC(C)=CC2=C1C(=O)C([N+]([O-])=O)C2=O CYUJGLFOZYZGCH-UHFFFAOYSA-N 0.000 description 2
- KLUILWQGFBJFNI-UHFFFAOYSA-N 4,6-dimethylindene-1,3-dione Chemical compound CC1=CC(C)=CC2=C1C(=O)CC2=O KLUILWQGFBJFNI-UHFFFAOYSA-N 0.000 description 2
- NFYGSTXIQUVQNX-UHFFFAOYSA-N 4,7-dimethyl-2-nitroindene-1,3-dione Chemical compound CC1=CC=C(C)C2=C1C(=O)C([N+]([O-])=O)C2=O NFYGSTXIQUVQNX-UHFFFAOYSA-N 0.000 description 2
- ALOOMSZBHTWGKM-UHFFFAOYSA-N 4-butoxy-2-nitroindene-1,3-dione Chemical compound CCCCOC1=CC=CC2=C1C(=O)C([N+]([O-])=O)C2=O ALOOMSZBHTWGKM-UHFFFAOYSA-N 0.000 description 2
- SPVXNAPUNWPIPW-UHFFFAOYSA-N 4-fluoro-2-nitroindene-1,3-dione Chemical compound C1=CC(F)=C2C(=O)C([N+](=O)[O-])C(=O)C2=C1 SPVXNAPUNWPIPW-UHFFFAOYSA-N 0.000 description 2
- KWBHLUOJJPXFKB-UHFFFAOYSA-N 4-methoxyindene-1,3-dione Chemical compound COC1=CC=CC2=C1C(=O)CC2=O KWBHLUOJJPXFKB-UHFFFAOYSA-N 0.000 description 2
- HNCUHEFLGUGWOT-UHFFFAOYSA-N 4-phenylindene-1,3-dione Chemical compound O=C1CC(=O)C2=C1C=CC=C2C1=CC=CC=C1 HNCUHEFLGUGWOT-UHFFFAOYSA-N 0.000 description 2
- IVODYRJOJFDUPA-UHFFFAOYSA-N 4-propan-2-yloxyindene-1,3-dione Chemical compound CC(C)OC1=CC=CC2=C1C(=O)CC2=O IVODYRJOJFDUPA-UHFFFAOYSA-N 0.000 description 2
- UBAWCUOJJZYUQQ-UHFFFAOYSA-N 4-propoxyindene-1,3-dione Chemical compound CCCOC1=CC=CC2=C1C(=O)CC2=O UBAWCUOJJZYUQQ-UHFFFAOYSA-N 0.000 description 2
- KMQFWCXRCDQFFQ-UHFFFAOYSA-N 5,6-dimethyl-2-nitroindene-1,3-dione Chemical compound C1=C(C)C(C)=CC2=C1C(=O)C([N+]([O-])=O)C2=O KMQFWCXRCDQFFQ-UHFFFAOYSA-N 0.000 description 2
- PBSZHPXRHKYMEC-UHFFFAOYSA-N 5,6-dimethylindene-1,3-dione Chemical compound C1=C(C)C(C)=CC2=C1C(=O)CC2=O PBSZHPXRHKYMEC-UHFFFAOYSA-N 0.000 description 2
- ADTNQTYUZPHLAS-UHFFFAOYSA-N 5-bromoindene-1,3-dione Chemical compound BrC1=CC=C2C(=O)CC(=O)C2=C1 ADTNQTYUZPHLAS-UHFFFAOYSA-N 0.000 description 2
- RMQQJCQNLSHFHS-UHFFFAOYSA-N 5-methoxy-6-methylindene-1,3-dione Chemical compound C1=C(C)C(OC)=CC2=C1C(=O)CC2=O RMQQJCQNLSHFHS-UHFFFAOYSA-N 0.000 description 2
- OCJFPAUIRWLATM-UHFFFAOYSA-N 5-methyl-2-nitroindene-1,3-dione Chemical compound CC1=CC=C2C(=O)C([N+]([O-])=O)C(=O)C2=C1 OCJFPAUIRWLATM-UHFFFAOYSA-N 0.000 description 2
- OOGJCWRSXJSCJR-UHFFFAOYSA-N 5-methylindene-1,3-dione Chemical compound CC1=CC=C2C(=O)CC(=O)C2=C1 OOGJCWRSXJSCJR-UHFFFAOYSA-N 0.000 description 2
- NNNOEYRPZFYOIS-UHFFFAOYSA-N 5-phenylindene-1,3-dione Chemical compound C=1C=C2C(=O)CC(=O)C2=CC=1C1=CC=CC=C1 NNNOEYRPZFYOIS-UHFFFAOYSA-N 0.000 description 2
- FTGCGMAEGVRUQD-UHFFFAOYSA-N 6-ethyl-4-methoxy-2-nitroindene-1,3-dione Chemical compound COC1=CC(CC)=CC2=C1C(=O)C([N+]([O-])=O)C2=O FTGCGMAEGVRUQD-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- QMNXUENRZFQJOB-UHFFFAOYSA-N cyclopenta[a]naphthalene-1,3-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)CC2=O QMNXUENRZFQJOB-UHFFFAOYSA-N 0.000 description 2
- YAJKDGXVZVCTKQ-UHFFFAOYSA-N cyclopenta[b]naphthalene-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)CC(=O)C3=CC2=C1 YAJKDGXVZVCTKQ-UHFFFAOYSA-N 0.000 description 2
- KKSNRHOMXHCRGF-UHFFFAOYSA-N dimethyl 3-methoxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=CC(OC)=C1C(=O)OC KKSNRHOMXHCRGF-UHFFFAOYSA-N 0.000 description 2
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000013207 serial dilution Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- KPWGMCBYMVBYKG-UHFFFAOYSA-N 2-nitro-4-phenylindene-1,3-dione Chemical compound C=12C(=O)C([N+](=O)[O-])C(=O)C2=CC=CC=1C1=CC=CC=C1 KPWGMCBYMVBYKG-UHFFFAOYSA-N 0.000 description 1
- PVOTZRBMRZWVED-UHFFFAOYSA-N 2-nitro-4-propan-2-yloxyindene-1,3-dione Chemical compound CC(C)OC1=CC=CC2=C1C(=O)C([N+]([O-])=O)C2=O PVOTZRBMRZWVED-UHFFFAOYSA-N 0.000 description 1
- KVMSIBDBCOEQSS-UHFFFAOYSA-N 2-nitro-4-propoxyindene-1,3-dione Chemical compound CCCOC1=CC=CC2=C1C(=O)C([N+]([O-])=O)C2=O KVMSIBDBCOEQSS-UHFFFAOYSA-N 0.000 description 1
- BTRIFCAWWGBIOF-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-nitroindene-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(=O)C([N+](=O)[O-])C2=O BTRIFCAWWGBIOF-UHFFFAOYSA-N 0.000 description 1
- IDLAOWFFKWRNHB-UHFFFAOYSA-N 4,5,6,7-tetrachloroindene-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)CC(=O)C2=C1Cl IDLAOWFFKWRNHB-UHFFFAOYSA-N 0.000 description 1
- WEPCDISQBQXOBE-UHFFFAOYSA-N 4,7-dimethyl-2-benzofuran-1,3-dione Chemical compound CC1=CC=C(C)C2=C1C(=O)OC2=O WEPCDISQBQXOBE-UHFFFAOYSA-N 0.000 description 1
- JMQGMDHERUWPEX-UHFFFAOYSA-N 4,7-dimethylindene-1,3-dione Chemical compound CC1=CC=C(C)C2=C1C(=O)CC2=O JMQGMDHERUWPEX-UHFFFAOYSA-N 0.000 description 1
- NFNVJUIXJQURPE-UHFFFAOYSA-N 4-(2-methylpropoxy)-2-nitroindene-1,3-dione Chemical compound CC(C)COC1=CC=CC2=C1C(=O)C([N+]([O-])=O)C2=O NFNVJUIXJQURPE-UHFFFAOYSA-N 0.000 description 1
- CLZNUZNABAVUBI-UHFFFAOYSA-N 4-(2-methylpropoxy)indene-1,3-dione Chemical compound CC(C)COC1=CC=CC2=C1C(=O)CC2=O CLZNUZNABAVUBI-UHFFFAOYSA-N 0.000 description 1
- SUQVGFUAHDXGSX-UHFFFAOYSA-N 4-bromo-2-nitroindene-1,3-dione Chemical compound C1=CC(Br)=C2C(=O)C([N+](=O)[O-])C(=O)C2=C1 SUQVGFUAHDXGSX-UHFFFAOYSA-N 0.000 description 1
- LFHCXMQLAZEASX-UHFFFAOYSA-N 4-butoxyindene-1,3-dione Chemical compound CCCCOC1=CC=CC2=C1C(=O)CC2=O LFHCXMQLAZEASX-UHFFFAOYSA-N 0.000 description 1
- UDFVVLUZJCUCBS-UHFFFAOYSA-N 4-ethoxy-2-nitroindene-1,3-dione Chemical compound CCOC1=CC=CC2=C1C(=O)C([N+]([O-])=O)C2=O UDFVVLUZJCUCBS-UHFFFAOYSA-N 0.000 description 1
- KPYRXDCLRRZPGB-UHFFFAOYSA-N 4-ethyl-2-nitroindene-1,3-dione Chemical compound CCC1=CC=CC2=C1C(=O)C([N+]([O-])=O)C2=O KPYRXDCLRRZPGB-UHFFFAOYSA-N 0.000 description 1
- PUUUIKQIJFJUSA-UHFFFAOYSA-N 4-ethylindene-1,3-dione Chemical compound CCC1=CC=CC2=C1C(=O)CC2=O PUUUIKQIJFJUSA-UHFFFAOYSA-N 0.000 description 1
- KUMYCNRXVCZWLR-UHFFFAOYSA-N 4-methoxy-2-nitroindene-1,3-dione Chemical compound COC1=CC=CC2=C1C(=O)C([N+]([O-])=O)C2=O KUMYCNRXVCZWLR-UHFFFAOYSA-N 0.000 description 1
- CTSZYBUVLHRTKF-UHFFFAOYSA-N 4-methoxy-6-methyl-2-nitroindene-1,3-dione Chemical compound COC1=CC(C)=CC2=C1C(=O)C([N+]([O-])=O)C2=O CTSZYBUVLHRTKF-UHFFFAOYSA-N 0.000 description 1
- XWQLNYZYNPWSJM-UHFFFAOYSA-N 4-methoxy-6-methylindene-1,3-dione Chemical compound COC1=CC(C)=CC2=C1C(=O)CC2=O XWQLNYZYNPWSJM-UHFFFAOYSA-N 0.000 description 1
- ALGRPRMNTYPWDJ-UHFFFAOYSA-N 4-methoxy-7-methyl-2-benzofuran-1,3-dione Chemical compound COC1=CC=C(C)C2=C1C(=O)OC2=O ALGRPRMNTYPWDJ-UHFFFAOYSA-N 0.000 description 1
- MORUHGIHMXAGPF-UHFFFAOYSA-N 4-methoxy-7-methyl-2-nitroindene-1,3-dione Chemical compound COC1=CC=C(C)C2=C1C(=O)C([N+]([O-])=O)C2=O MORUHGIHMXAGPF-UHFFFAOYSA-N 0.000 description 1
- GFONYYFTZWJJOW-UHFFFAOYSA-N 4-methoxy-7-methylindene-1,3-dione Chemical compound COC1=CC=C(C)C2=C1C(=O)CC2=O GFONYYFTZWJJOW-UHFFFAOYSA-N 0.000 description 1
- BCKVHOUUJMYIAN-UHFFFAOYSA-N 5-bromo-2-benzofuran-1,3-dione Chemical compound BrC1=CC=C2C(=O)OC(=O)C2=C1 BCKVHOUUJMYIAN-UHFFFAOYSA-N 0.000 description 1
- XVMKZAAFVWXIII-UHFFFAOYSA-N 5-fluoro-2-benzofuran-1,3-dione Chemical compound FC1=CC=C2C(=O)OC(=O)C2=C1 XVMKZAAFVWXIII-UHFFFAOYSA-N 0.000 description 1
- CNJKCHIEJVVHSQ-UHFFFAOYSA-N 5-methoxy-6-methyl-2-nitroindene-1,3-dione Chemical compound C1=C(C)C(OC)=CC2=C1C(=O)C([N+]([O-])=O)C2=O CNJKCHIEJVVHSQ-UHFFFAOYSA-N 0.000 description 1
- NUOSRFATOXIEJI-UHFFFAOYSA-N 6-ethyl-4-methoxyindene-1,3-dione Chemical compound COC1=CC(CC)=CC2=C1C(=O)CC2=O NUOSRFATOXIEJI-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- AXICIBPYBONRSP-UHFFFAOYSA-N Anofinic acid Chemical compound C1=C(C(O)=O)C=C2C=CC(C)(C)OC2=C1 AXICIBPYBONRSP-UHFFFAOYSA-N 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001239379 Calophysus macropterus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 241000551547 Dione <red algae> Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
- BPHHNXJPFPEJOF-UHFFFAOYSA-J chembl296966 Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=C(N)C2=C(O)C(N=NC3=CC=C(C=C3OC)C=3C=C(C(=CC=3)N=NC=3C(=C4C(N)=C(C=C(C4=CC=3)S([O-])(=O)=O)S([O-])(=O)=O)O)OC)=CC=C21 BPHHNXJPFPEJOF-UHFFFAOYSA-J 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- VMODTUAZZAIDGU-UHFFFAOYSA-N diethyl 4-methylbenzene-1,2-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C)C=C1C(=O)OCC VMODTUAZZAIDGU-UHFFFAOYSA-N 0.000 description 1
- DEMPTVYXFMKCIA-UHFFFAOYSA-N diethyl naphthalene-1,2-dicarboxylate Chemical compound C1=CC=CC2=C(C(=O)OCC)C(C(=O)OCC)=CC=C21 DEMPTVYXFMKCIA-UHFFFAOYSA-N 0.000 description 1
- UHTTVNLQYKRJIP-UHFFFAOYSA-N dimethyl 2,3-dihydro-1h-indene-4,5-dicarboxylate Chemical compound COC(=O)C1=CC=C2CCCC2=C1C(=O)OC UHTTVNLQYKRJIP-UHFFFAOYSA-N 0.000 description 1
- SRVVCVXNCDLHFO-UHFFFAOYSA-N dimethyl 3-butoxybenzene-1,2-dicarboxylate Chemical compound CCCCOC1=CC=CC(C(=O)OC)=C1C(=O)OC SRVVCVXNCDLHFO-UHFFFAOYSA-N 0.000 description 1
- DKAXMMVRWZGLNQ-UHFFFAOYSA-N dimethyl 3-ethoxybenzene-1,2-dicarboxylate Chemical compound CCOC1=CC=CC(C(=O)OC)=C1C(=O)OC DKAXMMVRWZGLNQ-UHFFFAOYSA-N 0.000 description 1
- XQKLZEQZJYFCGV-UHFFFAOYSA-N dimethyl 3-methoxy-5-methylbenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC(C)=CC(OC)=C1C(=O)OC XQKLZEQZJYFCGV-UHFFFAOYSA-N 0.000 description 1
- LRUDOARPHSTPPU-UHFFFAOYSA-N dimethyl 3-phenylbenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(=O)OC LRUDOARPHSTPPU-UHFFFAOYSA-N 0.000 description 1
- JKJKZHLNKRHCFA-UHFFFAOYSA-N dimethyl 3-propan-2-yloxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=CC(OC(C)C)=C1C(=O)OC JKJKZHLNKRHCFA-UHFFFAOYSA-N 0.000 description 1
- FQOJAKYIPJAQPS-UHFFFAOYSA-N dimethyl 3-propoxybenzene-1,2-dicarboxylate Chemical compound CCCOC1=CC=CC(C(=O)OC)=C1C(=O)OC FQOJAKYIPJAQPS-UHFFFAOYSA-N 0.000 description 1
- PBHDDYJJBJNTLH-UHFFFAOYSA-N dimethyl 4-methoxy-5-methylbenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC(C)=C(OC)C=C1C(=O)OC PBHDDYJJBJNTLH-UHFFFAOYSA-N 0.000 description 1
- MINFPQZYHRBMNP-UHFFFAOYSA-N dimethyl 4-phenylbenzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1C1=CC=CC=C1 MINFPQZYHRBMNP-UHFFFAOYSA-N 0.000 description 1
- JRCHRQNLEBCDGP-UHFFFAOYSA-N dimethyl 5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylate Chemical compound C1CCCC2=C(C(=O)OC)C(C(=O)OC)=CC=C21 JRCHRQNLEBCDGP-UHFFFAOYSA-N 0.000 description 1
- NIQCNGHVCWTJSM-UHFFFAOYSA-N dimethyl benzenedicarboxylate Natural products COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000839 emulsion Substances 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
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- MSKBUVDLWGTLAC-UHFFFAOYSA-N methyl 2-(1,3-dioxoisoindol-2-yl)oxyacetate Chemical compound C1=CC=C2C(=O)N(OCC(=O)OC)C(=O)C2=C1 MSKBUVDLWGTLAC-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 229940066827 pertussis vaccine Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 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
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/38—Unsaturated compounds containing keto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/48—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1330072*[A GB1412291A (en) | 1972-01-25 | 1972-01-25 | 2-nitro-indan-1,3-diones methods for their preparation and anti-allergic compositions containing them |
| GB1330072 | 1972-03-22 | ||
| GB2870772 | 1972-06-20 | ||
| GB4802772 | 1972-10-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135632B true NO135632B (xx) | 1977-01-24 |
| NO135632C NO135632C (xx) | 1977-05-04 |
Family
ID=27447285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4655/72A NO135632C (xx) | 1972-01-25 | 1972-12-15 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3936504A (xx) |
| BE (1) | BE792867A (xx) |
| CA (2) | CA1017757A (xx) |
| CH (1) | CH592603A5 (xx) |
| DE (1) | DE2261568A1 (xx) |
| DK (2) | DK137379B (xx) |
| FR (1) | FR2181661B1 (xx) |
| GB (1) | GB1412291A (xx) |
| NL (1) | NL7217175A (xx) |
| NO (1) | NO135632C (xx) |
| SE (2) | SE401821B (xx) |
-
1972
- 1972-01-25 GB GB1330072*[A patent/GB1412291A/en not_active Expired
- 1972-12-14 SE SE7216376A patent/SE401821B/xx unknown
- 1972-12-15 NO NO4655/72A patent/NO135632C/no unknown
- 1972-12-15 CA CA159,009A patent/CA1017757A/en not_active Expired
- 1972-12-15 BE BE792867D patent/BE792867A/xx unknown
- 1972-12-15 DK DK629972AA patent/DK137379B/da unknown
- 1972-12-15 CH CH1833772A patent/CH592603A5/xx not_active IP Right Cessation
- 1972-12-15 DE DE19722261568 patent/DE2261568A1/de active Pending
- 1972-12-15 NL NL7217175A patent/NL7217175A/xx not_active Application Discontinuation
- 1972-12-21 US US05/317,296 patent/US3936504A/en not_active Expired - Lifetime
-
1973
- 1973-01-10 FR FR7300713A patent/FR2181661B1/fr not_active Expired
-
1976
- 1976-09-17 SE SE7610364A patent/SE7610364L/xx unknown
- 1976-12-09 CA CA267,480A patent/CA1021799A/en not_active Expired
-
1977
- 1977-12-15 DK DK560577A patent/DK560577A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2181661B1 (xx) | 1976-06-25 |
| CA1017757A (en) | 1977-09-20 |
| NL7217175A (xx) | 1973-07-27 |
| US3936504A (en) | 1976-02-03 |
| DK137379C (xx) | 1978-08-07 |
| NO135632C (xx) | 1977-05-04 |
| DK560577A (da) | 1977-12-15 |
| SE401821B (sv) | 1978-05-29 |
| DE2261568A1 (de) | 1973-08-02 |
| SE7610364L (sv) | 1976-09-17 |
| CH592603A5 (xx) | 1977-10-31 |
| CA1021799A (en) | 1977-11-29 |
| BE792867A (fr) | 1973-06-15 |
| GB1412291A (en) | 1975-11-05 |
| FR2181661A1 (xx) | 1973-12-07 |
| DK137379B (da) | 1978-02-27 |
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