NO750864L - - Google Patents
Info
- Publication number
- NO750864L NO750864L NO750864A NO750864A NO750864L NO 750864 L NO750864 L NO 750864L NO 750864 A NO750864 A NO 750864A NO 750864 A NO750864 A NO 750864A NO 750864 L NO750864 L NO 750864L
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- nitrocoumarin
- added
- room temperature
- product
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000006396 nitration reaction Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 239000006187 pill Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- 239000000725 suspension Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 238000001914 filtration Methods 0.000 description 33
- 239000000047 product Substances 0.000 description 33
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 239000011734 sodium Substances 0.000 description 17
- -1 aralkoxy Chemical group 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 13
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 230000004044 response Effects 0.000 description 6
- NZQAQAUWFHMVEM-UHFFFAOYSA-N 4-hydroxy-3-nitrochromen-2-one Chemical compound C1=CC=CC2=C1OC(=O)C([N+]([O-])=O)=C2O NZQAQAUWFHMVEM-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- YTCVPEZECJYZRK-UHFFFAOYSA-N 3-nitrochromen-2-one Chemical class C1=CC=C2OC(=O)C([N+](=O)[O-])=CC2=C1 YTCVPEZECJYZRK-UHFFFAOYSA-N 0.000 description 3
- CEVVPXAFAUWIMW-UHFFFAOYSA-N 4-hydroxy-3,6-dinitrochromen-2-one Chemical compound C1=CC([N+]([O-])=O)=CC2=C1OC(=O)C([N+]([O-])=O)=C2O CEVVPXAFAUWIMW-UHFFFAOYSA-N 0.000 description 3
- VOBWYJZFRGXBFE-UHFFFAOYSA-N 4-hydroxy-3-nitro-7-propoxychromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=CC(OCCC)=CC=C21 VOBWYJZFRGXBFE-UHFFFAOYSA-N 0.000 description 3
- WOZQGVWTWZLETB-UHFFFAOYSA-N 4-hydroxy-6,7-dimethyl-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(C)C(C)=C2 WOZQGVWTWZLETB-UHFFFAOYSA-N 0.000 description 3
- CPMOVDXRQYGPSF-UHFFFAOYSA-N 4-hydroxy-6-methoxy-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=CC(OC)=CC=C21 CPMOVDXRQYGPSF-UHFFFAOYSA-N 0.000 description 3
- XANZFICLJFFUKG-UHFFFAOYSA-N 4-hydroxy-7-methoxy-3-nitrochromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=CC(OC)=CC=C21 XANZFICLJFFUKG-UHFFFAOYSA-N 0.000 description 3
- QFTOEJKXJKAMNK-UHFFFAOYSA-N 6,7-diethyl-4-hydroxy-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(CC)C(CC)=C2 QFTOEJKXJKAMNK-UHFFFAOYSA-N 0.000 description 3
- UBDIXRVYJPYHNO-UHFFFAOYSA-N 6-chloro-4-hydroxy-3-nitrochromen-2-one Chemical compound C1=CC(Cl)=CC2=C1OC(=O)C([N+]([O-])=O)=C2O UBDIXRVYJPYHNO-UHFFFAOYSA-N 0.000 description 3
- ZLDUKGHXYIMWJP-UHFFFAOYSA-N 7-bromo-4-hydroxy-3-nitrochromen-2-one Chemical compound C1=C(Br)C=CC2=C1OC(=O)C([N+]([O-])=O)=C2O ZLDUKGHXYIMWJP-UHFFFAOYSA-N 0.000 description 3
- WLXORWBDJTUCLG-UHFFFAOYSA-N 7-chloro-4-hydroxy-3-nitrochromen-2-one Chemical compound C1=C(Cl)C=CC2=C1OC(=O)C([N+]([O-])=O)=C2O WLXORWBDJTUCLG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- DXMGZEOFDYHIIO-UHFFFAOYSA-N 4-hydroxy-3-nitro-6,7-dipropylchromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(CCC)C(CCC)=C2 DXMGZEOFDYHIIO-UHFFFAOYSA-N 0.000 description 2
- OERMPGGFPDGNOZ-UHFFFAOYSA-N 4-hydroxy-5-methoxy-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=CC=C2OC OERMPGGFPDGNOZ-UHFFFAOYSA-N 0.000 description 2
- KUALEWXMXRPRRL-UHFFFAOYSA-N 4-hydroxy-6-methyl-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=CC(C)=CC=C21 KUALEWXMXRPRRL-UHFFFAOYSA-N 0.000 description 2
- AUWQRFLQKOBFJT-UHFFFAOYSA-N 4-hydroxy-7-methoxy-6-methyl-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(OC)C(C)=C2 AUWQRFLQKOBFJT-UHFFFAOYSA-N 0.000 description 2
- RASGTZZGBPNBLH-UHFFFAOYSA-N 6-bromo-4-hydroxy-3-nitrochromen-2-one Chemical compound C1=CC(Br)=CC2=C1OC(=O)C([N+]([O-])=O)=C2O RASGTZZGBPNBLH-UHFFFAOYSA-N 0.000 description 2
- CLSXJCRBXDOZJP-UHFFFAOYSA-N 6-ethyl-4-hydroxy-7-methyl-3-nitrochromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=C1C=C(CC)C(C)=C2 CLSXJCRBXDOZJP-UHFFFAOYSA-N 0.000 description 2
- LVZTYKPCDIGFBZ-UHFFFAOYSA-N 7-ethoxy-6-ethyl-4-hydroxy-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(OCC)C(CC)=C2 LVZTYKPCDIGFBZ-UHFFFAOYSA-N 0.000 description 2
- WTAQDUQFXNCDKR-UHFFFAOYSA-N 7-ethyl-4-hydroxy-6-methyl-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(CC)C(C)=C2 WTAQDUQFXNCDKR-UHFFFAOYSA-N 0.000 description 2
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
- GOLCXWYRSKYTSP-UHFFFAOYSA-N Arsenious Acid Chemical compound O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 206010039083 rhinitis Diseases 0.000 description 2
- 238000013207 serial dilution Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical class CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 1
- XCLCBQOPVFPFBN-UHFFFAOYSA-N 4,7-dihydroxy-3,6,8-trinitrochromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=C([N+]([O-])=O)C(O)=C([N+]([O-])=O)C=C21 XCLCBQOPVFPFBN-UHFFFAOYSA-N 0.000 description 1
- SARRSDARCKJMPK-UHFFFAOYSA-N 4,7-dihydroxy-3,6-dinitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(O)C([N+]([O-])=O)=C2 SARRSDARCKJMPK-UHFFFAOYSA-N 0.000 description 1
- KKQAFZBJICXPRU-UHFFFAOYSA-N 4,7-dihydroxy-3,8-dinitrochromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=C([N+]([O-])=O)C(O)=CC=C21 KKQAFZBJICXPRU-UHFFFAOYSA-N 0.000 description 1
- UIBQLWQIGFZIID-UHFFFAOYSA-N 4,7-dihydroxy-3-nitrochromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=CC(O)=CC=C21 UIBQLWQIGFZIID-UHFFFAOYSA-N 0.000 description 1
- KICKNBIKUUIDSK-UHFFFAOYSA-N 4,7-dihydroxychromen-2-one;hydrate Chemical compound O.OC1=CC(=O)OC2=CC(O)=CC=C21 KICKNBIKUUIDSK-UHFFFAOYSA-N 0.000 description 1
- WVVNGXKQLLKZPP-UHFFFAOYSA-N 4-hydroxy-3,6-dinitrochromen-2-one;sodium Chemical compound [Na].C1=CC([N+]([O-])=O)=CC2=C1OC(=O)C([N+]([O-])=O)=C2O WVVNGXKQLLKZPP-UHFFFAOYSA-N 0.000 description 1
- QHIPEHKKGLLQRF-UHFFFAOYSA-N 4-hydroxy-3-nitro-7-propoxychromen-2-one;sodium Chemical compound [Na].OC1=C([N+]([O-])=O)C(=O)OC2=CC(OCCC)=CC=C21 QHIPEHKKGLLQRF-UHFFFAOYSA-N 0.000 description 1
- SKASSVARNXDRMC-UHFFFAOYSA-N 4-hydroxy-5,6,7-trimethylchromen-2-one Chemical compound O1C(=O)C=C(O)C2=C1C=C(C)C(C)=C2C SKASSVARNXDRMC-UHFFFAOYSA-N 0.000 description 1
- LFFCJEOKCYTBDD-UHFFFAOYSA-N 4-hydroxy-5-methoxychromen-2-one Chemical compound O1C(=O)C=C(O)C2=C1C=CC=C2OC LFFCJEOKCYTBDD-UHFFFAOYSA-N 0.000 description 1
- JOQLOWVQNWMIRK-UHFFFAOYSA-N 4-hydroxy-5-methyl-3-nitro-7-propan-2-ylchromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=CC(C(C)C)=CC(C)=C21 JOQLOWVQNWMIRK-UHFFFAOYSA-N 0.000 description 1
- NDOVCKMKZPJBBE-UHFFFAOYSA-N 4-hydroxy-5-methyl-3-nitro-8-propan-2-ylchromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=C1C(C)=CC=C2C(C)C NDOVCKMKZPJBBE-UHFFFAOYSA-N 0.000 description 1
- AYHZQBMBPNZPEY-UHFFFAOYSA-N 4-hydroxy-6,7-dimethylchromen-2-one Chemical compound O1C(=O)C=C(O)C2=C1C=C(C)C(C)=C2 AYHZQBMBPNZPEY-UHFFFAOYSA-N 0.000 description 1
- CIBMJDFTKNIHKQ-UHFFFAOYSA-N 4-hydroxy-6,7-dipropylchromen-2-one Chemical compound O1C(=O)C=C(O)C2=C1C=C(CCC)C(CCC)=C2 CIBMJDFTKNIHKQ-UHFFFAOYSA-N 0.000 description 1
- OIJLCRLAKRHBBN-UHFFFAOYSA-N 4-hydroxy-6,8-dimethyl-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=CC(C)=CC(C)=C21 OIJLCRLAKRHBBN-UHFFFAOYSA-N 0.000 description 1
- HVHIQQVTLCUBKA-UHFFFAOYSA-N 4-hydroxy-6,8-dimethylchromen-2-one Chemical compound O1C(=O)C=C(O)C2=CC(C)=CC(C)=C21 HVHIQQVTLCUBKA-UHFFFAOYSA-N 0.000 description 1
- KNVVAFLWWDZVRA-UHFFFAOYSA-N 4-hydroxy-6-methoxy-3-nitrochromen-2-one;sodium Chemical compound [Na].O1C(=O)C([N+]([O-])=O)=C(O)C2=CC(OC)=CC=C21 KNVVAFLWWDZVRA-UHFFFAOYSA-N 0.000 description 1
- KFXXRRQBVLINPH-UHFFFAOYSA-N 4-hydroxy-6-methoxychromen-2-one Chemical compound O1C(=O)C=C(O)C2=CC(OC)=CC=C21 KFXXRRQBVLINPH-UHFFFAOYSA-N 0.000 description 1
- WIRGBZBGYNIZIB-UHFFFAOYSA-N 4-hydroxy-6-methylchromen-2-one Chemical compound O1C(=O)C=C(O)C2=CC(C)=CC=C21 WIRGBZBGYNIZIB-UHFFFAOYSA-N 0.000 description 1
- OCVAZEDQAFICLI-UHFFFAOYSA-N 4-hydroxy-6-phenylmethoxychromen-2-one Chemical compound C=1C=2C(O)=CC(=O)OC=2C=CC=1OCC1=CC=CC=C1 OCVAZEDQAFICLI-UHFFFAOYSA-N 0.000 description 1
- DZGDYAJCQWPAKE-UHFFFAOYSA-N 4-hydroxy-7,8-dimethylchromen-2-one Chemical compound OC1=CC(=O)OC2=C(C)C(C)=CC=C21 DZGDYAJCQWPAKE-UHFFFAOYSA-N 0.000 description 1
- NDQQBUKSTAUBFI-UHFFFAOYSA-N 4-hydroxy-7-methoxy-3-nitro-6-propylchromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=C1C=C(CCC)C(OC)=C2 NDQQBUKSTAUBFI-UHFFFAOYSA-N 0.000 description 1
- LERYPVGFHJAHPU-UHFFFAOYSA-N 4-hydroxy-7-methoxy-6-methylchromen-2-one Chemical compound O1C(=O)C=C(O)C2=C1C=C(OC)C(C)=C2 LERYPVGFHJAHPU-UHFFFAOYSA-N 0.000 description 1
- BVEGTNLQOFTOIF-UHFFFAOYSA-N 4-hydroxy-7-methoxy-6-propylchromen-2-one Chemical compound OC1=CC(=O)OC2=C1C=C(CCC)C(OC)=C2 BVEGTNLQOFTOIF-UHFFFAOYSA-N 0.000 description 1
- GZKYQBNTSOFWPM-UHFFFAOYSA-N 4-hydroxy-7-methoxy-8-methyl-3-nitrochromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=C(C)C(OC)=CC=C21 GZKYQBNTSOFWPM-UHFFFAOYSA-N 0.000 description 1
- ZPPACLOAXPSWDB-UHFFFAOYSA-N 4-hydroxy-7-methoxy-8-methylchromen-2-one Chemical compound OC1=CC(=O)OC2=C(C)C(OC)=CC=C21 ZPPACLOAXPSWDB-UHFFFAOYSA-N 0.000 description 1
- MJBHLQMPKBMZSF-UHFFFAOYSA-N 4-hydroxy-7-methoxychromen-2-one Chemical compound OC1=CC(=O)OC2=CC(OC)=CC=C21 MJBHLQMPKBMZSF-UHFFFAOYSA-N 0.000 description 1
- USOPQJDZCBCFJG-UHFFFAOYSA-N 4-hydroxy-7-propoxychromen-2-one Chemical compound OC1=CC(=O)OC2=CC(OCCC)=CC=C21 USOPQJDZCBCFJG-UHFFFAOYSA-N 0.000 description 1
- NFFPEZYDUVHXIU-UHFFFAOYSA-N 4-hydroxy-8-methyl-3-nitrochromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=C1C=CC=C2C NFFPEZYDUVHXIU-UHFFFAOYSA-N 0.000 description 1
- SWTGXRICOTZSFY-UHFFFAOYSA-N 4-hydroxy-8-methylchromen-2-one Chemical compound OC1=CC(=O)OC2=C1C=CC=C2C SWTGXRICOTZSFY-UHFFFAOYSA-N 0.000 description 1
- JRSYUHVXYISMOU-UHFFFAOYSA-N 6,7-diethyl-4-hydroxychromen-2-one Chemical compound O1C(=O)C=C(O)C2=C1C=C(CC)C(CC)=C2 JRSYUHVXYISMOU-UHFFFAOYSA-N 0.000 description 1
- JPYQLNZLTJDRNL-UHFFFAOYSA-N 6-bromo-4-hydroxy-3-nitrochromen-2-one;sodium Chemical compound [Na].C1=CC(Br)=CC2=C1OC(=O)C([N+]([O-])=O)=C2O JPYQLNZLTJDRNL-UHFFFAOYSA-N 0.000 description 1
- KNMCTCABMSGXGR-UHFFFAOYSA-N 6-bromo-4-hydroxychromen-2-one Chemical compound C1=CC(Br)=CC2=C1OC(=O)C=C2O KNMCTCABMSGXGR-UHFFFAOYSA-N 0.000 description 1
- AMBONCRHFJSJLA-UHFFFAOYSA-N 6-chloro-4-hydroxy-3-nitrochromen-2-one;sodium Chemical compound [Na].C1=CC(Cl)=CC2=C1OC(=O)C([N+]([O-])=O)=C2O AMBONCRHFJSJLA-UHFFFAOYSA-N 0.000 description 1
- HUMZENGQNOATEQ-UHFFFAOYSA-N 6-chloro-4-hydroxycoumarin Chemical compound C1=CC(Cl)=CC2=C1OC(=O)C=C2O HUMZENGQNOATEQ-UHFFFAOYSA-N 0.000 description 1
- UAADZDHLBGXZJC-UHFFFAOYSA-N 6-ethyl-4-hydroxy-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=CC(CC)=CC=C21 UAADZDHLBGXZJC-UHFFFAOYSA-N 0.000 description 1
- DBVBKQLWSBTXLT-UHFFFAOYSA-N 6-ethyl-4-hydroxy-7-methoxy-3-nitrochromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=C1C=C(CC)C(OC)=C2 DBVBKQLWSBTXLT-UHFFFAOYSA-N 0.000 description 1
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- JYULRNGSVREOJU-UHFFFAOYSA-N 6-ethyl-4-hydroxychromen-2-one Chemical compound O1C(=O)C=C(O)C2=CC(CC)=CC=C21 JYULRNGSVREOJU-UHFFFAOYSA-N 0.000 description 1
- CFULEYDXZUKVNB-UHFFFAOYSA-N 7-bromo-4-hydroxy-3-nitrochromen-2-one;sodium Chemical compound [Na].C1=C(Br)C=CC2=C1OC(=O)C([N+]([O-])=O)=C2O CFULEYDXZUKVNB-UHFFFAOYSA-N 0.000 description 1
- UJWIUPBUKQLTTJ-UHFFFAOYSA-N 7-bromo-4-hydroxychromen-2-one Chemical compound C1=C(Br)C=CC2=C1OC(=O)C=C2O UJWIUPBUKQLTTJ-UHFFFAOYSA-N 0.000 description 1
- KXMUNKPRHFHESS-UHFFFAOYSA-N 7-chloro-4-hydroxy-3-nitrochromen-2-one;sodium Chemical compound [Na].C1=C(Cl)C=CC2=C1OC(=O)C([N+]([O-])=O)=C2O KXMUNKPRHFHESS-UHFFFAOYSA-N 0.000 description 1
- PKVBFOLFCIJRRE-UHFFFAOYSA-N 7-chloro-4-hydroxychromen-2-one Chemical compound C1=C(Cl)C=CC2=C1OC(=O)C=C2O PKVBFOLFCIJRRE-UHFFFAOYSA-N 0.000 description 1
- WRIWCTGCJAGBPC-UHFFFAOYSA-N 7-ethoxy-4-hydroxy-3-nitrochromen-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=CC(OCC)=CC=C21 WRIWCTGCJAGBPC-UHFFFAOYSA-N 0.000 description 1
- WPWHOFJXRHXQGD-UHFFFAOYSA-N 7-ethoxy-4-hydroxy-6-methyl-3-nitrochromen-2-one Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(OCC)C(C)=C2 WPWHOFJXRHXQGD-UHFFFAOYSA-N 0.000 description 1
- FCKZDVZDHOBNSC-UHFFFAOYSA-N 7-ethoxy-4-hydroxy-6-methylchromen-2-one Chemical compound O1C(=O)C=C(O)C2=C1C=C(OCC)C(C)=C2 FCKZDVZDHOBNSC-UHFFFAOYSA-N 0.000 description 1
- BPWIJZQVCZRWTJ-UHFFFAOYSA-N 7-ethoxy-4-hydroxychromen-2-one Chemical compound OC1=CC(=O)OC2=CC(OCC)=CC=C21 BPWIJZQVCZRWTJ-UHFFFAOYSA-N 0.000 description 1
- DVSUEIITDYMTFB-UHFFFAOYSA-N 7-ethyl-4-hydroxy-6-methylchromen-2-one Chemical compound O1C(=O)C=C(O)C2=C1C=C(CC)C(C)=C2 DVSUEIITDYMTFB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 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
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- XJYDDRXKAGBCBK-UHFFFAOYSA-N N-(4-hydroxy-3-nitro-2-oxochromen-7-yl)acetamide Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=CC(NC(=O)C)=CC=C21 XJYDDRXKAGBCBK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 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
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 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
- 244000309464 bull Species 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 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
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960001340 histamine Drugs 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
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 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
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 229940066827 pertussis vaccine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004076 pyridyl group Chemical group 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1887673A GB1432809A (en) | 1973-04-19 | 1973-04-19 | Coumarin derivatives |
| NO741385 | 1974-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO750864L true NO750864L (el) | 1974-10-22 |
Family
ID=26253659
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO750863A NO750863L (el) | 1973-04-19 | 1975-03-13 | |
| NO750864A NO750864L (el) | 1973-04-19 | 1975-03-13 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO750863A NO750863L (el) | 1973-04-19 | 1975-03-13 |
Country Status (1)
| Country | Link |
|---|---|
| NO (2) | NO750863L (el) |
-
1975
- 1975-03-13 NO NO750863A patent/NO750863L/no unknown
- 1975-03-13 NO NO750864A patent/NO750864L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO750863L (el) | 1974-10-22 |
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