NO124994B - - Google Patents
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- NO124994B NO124994B NO373169A NO373169A NO124994B NO 124994 B NO124994 B NO 124994B NO 373169 A NO373169 A NO 373169A NO 373169 A NO373169 A NO 373169A NO 124994 B NO124994 B NO 124994B
- Authority
- NO
- Norway
- Prior art keywords
- bis
- yloxy
- found
- parts
- analysis
- Prior art date
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- 238000000034 method Methods 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 30
- -1 2-hydroxy-trimethylene Chemical group 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 166
- 238000004458 analytical method Methods 0.000 description 92
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 67
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- 238000002425 crystallisation Methods 0.000 description 53
- 230000008025 crystallization Effects 0.000 description 53
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- 238000002844 melting Methods 0.000 description 33
- 230000008018 melting Effects 0.000 description 33
- 239000002253 acid Substances 0.000 description 30
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 30
- 150000002148 esters Chemical class 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- YPTJKHVBDCRKNF-UHFFFAOYSA-N 2',6'-Dihydroxyacetophenone Chemical compound CC(=O)C1=C(O)C=CC=C1O YPTJKHVBDCRKNF-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 229910001868 water Inorganic materials 0.000 description 19
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 208000006673 asthma Diseases 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- 125000005594 diketone group Chemical class 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000427 antigen Substances 0.000 description 8
- 102000036639 antigens Human genes 0.000 description 8
- 108091007433 antigens Proteins 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical class O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RUOPAUDVYRHXDB-UHFFFAOYSA-N 1-[2-[3-(2-acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]-6-hydroxyphenyl]ethanone Chemical compound CC(=O)C1=C(O)C=CC=C1OCC(O)COC1=CC=CC(O)=C1C(C)=O RUOPAUDVYRHXDB-UHFFFAOYSA-N 0.000 description 4
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229940124630 bronchodilator Drugs 0.000 description 4
- 150000004683 dihydrates Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000004682 monohydrates Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- BVFXPYVNONOIOL-UHFFFAOYSA-N 1-[2-[3-(2-acetyl-3-hydroxyphenoxy)propoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O BVFXPYVNONOIOL-UHFFFAOYSA-N 0.000 description 3
- DHUTWEOFUONKPW-UHFFFAOYSA-N 1-[2-[4-(2-acetyl-3-hydroxyphenoxy)but-2-enoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCC=CCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O DHUTWEOFUONKPW-UHFFFAOYSA-N 0.000 description 3
- SDMVIQZFCIDENA-UHFFFAOYSA-N 1-[4-[5-(2-acetyl-3-hydroxyphenoxy)pentoxy]-2-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCCOC2=CC(=C(C=C2)C(C)=O)O)C=CC=C1O SDMVIQZFCIDENA-UHFFFAOYSA-N 0.000 description 3
- WLDWSGZHNBANIO-UHFFFAOYSA-N 2',5'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC(O)=CC=C1O WLDWSGZHNBANIO-UHFFFAOYSA-N 0.000 description 3
- HNSWSZHQXDJXSS-UHFFFAOYSA-N 5-[3-(2-carboxy-4-oxochromen-5-yl)oxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 HNSWSZHQXDJXSS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 201000009961 allergic asthma Diseases 0.000 description 3
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- AHQTYUNPLZYCOL-UHFFFAOYSA-N 1,4-dioxane;ethanol;hydrate Chemical compound O.CCO.C1COCCO1 AHQTYUNPLZYCOL-UHFFFAOYSA-N 0.000 description 2
- DBHSMAKQPAAGPD-UHFFFAOYSA-N 1-[2-[4-(2-acetyl-3-hydroxyphenoxy)butoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O DBHSMAKQPAAGPD-UHFFFAOYSA-N 0.000 description 2
- MOWNIAOVRQFQEF-UHFFFAOYSA-N 1-[2-[5-(2-acetyl-3-hydroxyphenoxy)pentoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O MOWNIAOVRQFQEF-UHFFFAOYSA-N 0.000 description 2
- XUCAYUZOQRDJRZ-UHFFFAOYSA-N 1-[2-hydroxy-6-(2-hydroxypropoxy)phenyl]ethanone Chemical compound CC(O)COC1=CC=CC(O)=C1C(C)=O XUCAYUZOQRDJRZ-UHFFFAOYSA-N 0.000 description 2
- YKZNLYQRDOZDKJ-UHFFFAOYSA-N 1-[4-[3-(2-acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]-2-hydroxyphenyl]ethanone Chemical compound CC(=O)C1=C(O)C=C(OCC(O)COC2=C(C(C)=O)C(O)=CC=C2)C=C1 YKZNLYQRDOZDKJ-UHFFFAOYSA-N 0.000 description 2
- HEJLFBLJYFSKCE-UHFFFAOYSA-N 2',3'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1O HEJLFBLJYFSKCE-UHFFFAOYSA-N 0.000 description 2
- YIHPBFNJUANWMM-UHFFFAOYSA-N 5-[10-(2-carboxy-4-oxochromen-5-yl)oxydecoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCCCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 YIHPBFNJUANWMM-UHFFFAOYSA-N 0.000 description 2
- LMHNIXHQAJSZRY-UHFFFAOYSA-N 5-[2-(2-carboxy-4-oxochromen-5-yl)oxyethoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 LMHNIXHQAJSZRY-UHFFFAOYSA-N 0.000 description 2
- NQMCHRKBRSYHAM-UHFFFAOYSA-N 5-[3-[4-[3-(2-carboxy-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]butoxy]-2-hydroxypropoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COCCCCOCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 NQMCHRKBRSYHAM-UHFFFAOYSA-N 0.000 description 2
- UXTDVBFZKFGSIM-UHFFFAOYSA-N 5-[4-(2-carboxy-4-oxochromen-5-yl)oxy-2,3-dihydroxybutoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)C(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 UXTDVBFZKFGSIM-UHFFFAOYSA-N 0.000 description 2
- ZSLZPIBPJOBWGH-UHFFFAOYSA-N 5-[4-(2-carboxy-4-oxochromen-5-yl)oxy-3-hydroxybutoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)CCOC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 ZSLZPIBPJOBWGH-UHFFFAOYSA-N 0.000 description 2
- DWCCSURARIZGPH-UHFFFAOYSA-N 5-[4-(2-carboxy-4-oxochromen-5-yl)oxybut-2-enoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC=CCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 DWCCSURARIZGPH-UHFFFAOYSA-N 0.000 description 2
- WOLDEHWWZNMZJV-UHFFFAOYSA-N 5-[4-(2-carboxy-4-oxochromen-5-yl)oxybutoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 WOLDEHWWZNMZJV-UHFFFAOYSA-N 0.000 description 2
- PWAATCXREMPGJZ-UHFFFAOYSA-N 5-[5-(2-carboxy-8-chloro-4-oxochromen-5-yl)oxypentoxy]-8-chloro-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(Cl)=CC=C2OCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=C(Cl)C=C1 PWAATCXREMPGJZ-UHFFFAOYSA-N 0.000 description 2
- QGEKJPVUUYFRQV-UHFFFAOYSA-N 5-[6-(2-carboxy-4-oxochromen-5-yl)oxyhexoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 QGEKJPVUUYFRQV-UHFFFAOYSA-N 0.000 description 2
- UNIVIWZHQOASHG-UHFFFAOYSA-N 5-[9-(2-carboxy-4-oxochromen-5-yl)oxynonoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 UNIVIWZHQOASHG-UHFFFAOYSA-N 0.000 description 2
- NWTNHOSYXTWRQT-UHFFFAOYSA-N 6-[5-(2-carboxy-4-oxochromen-6-yl)oxypentoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=CC(OCCCCCOC=3C=C4C(=O)C=C(OC4=CC=3)C(=O)O)=CC=C21 NWTNHOSYXTWRQT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- FJRXGBBVWWBHMW-UHFFFAOYSA-N O.O.O.O.[Na].[Na] Chemical compound O.O.O.O.[Na].[Na] FJRXGBBVWWBHMW-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 208000024711 extrinsic asthma Diseases 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 201000010659 intrinsic asthma Diseases 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004199 lung function Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- UILPJVPSNHJFIK-UHFFFAOYSA-N p-methoxy-o-hydroxyacetophenone Natural products COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 description 2
- 239000008024 pharmaceutical diluent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 150000004685 tetrahydrates Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 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
- RMXLHIUHKIVPAB-OWOJBTEDSA-N (e)-1,4-dibromobut-2-ene Chemical compound BrC\C=C\CBr RMXLHIUHKIVPAB-OWOJBTEDSA-N 0.000 description 1
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 description 1
- KIHQZLPHVZKELA-UHFFFAOYSA-N 1,3-dibromopropan-2-ol Chemical compound BrCC(O)CBr KIHQZLPHVZKELA-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 description 1
- YDPZWUMQKMLLHC-UHFFFAOYSA-N 1,5-dibromo-3-methylpentane Chemical compound BrCCC(C)CCBr YDPZWUMQKMLLHC-UHFFFAOYSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- WGAXVZXBFBHLMC-UHFFFAOYSA-N 1,9-dibromononane Chemical compound BrCCCCCCCCCBr WGAXVZXBFBHLMC-UHFFFAOYSA-N 0.000 description 1
- UQXOTLVZBQYIMX-UHFFFAOYSA-N 1-[2-(2-ethoxyethoxy)-6-hydroxyphenyl]ethanone Chemical compound CCOCCOC1=CC=CC(O)=C1C(C)=O UQXOTLVZBQYIMX-UHFFFAOYSA-N 0.000 description 1
- HZRXQORWKLUXON-UHFFFAOYSA-N 1-[2-[10-(2-acetyl-3-hydroxyphenoxy)decoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCCCCCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O HZRXQORWKLUXON-UHFFFAOYSA-N 0.000 description 1
- GZBWDCRBDBZYAV-UHFFFAOYSA-N 1-[2-[2-(2-acetyl-3-hydroxyphenoxy)ethoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O GZBWDCRBDBZYAV-UHFFFAOYSA-N 0.000 description 1
- WODXTRFWFHXFBY-UHFFFAOYSA-N 1-[2-[3-[4-[3-(2-acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]butoxy]-2-hydroxypropoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCC(COCCCCOCC(COC2=C(C(=CC=C2)O)C(C)=O)O)O)C=CC=C1O WODXTRFWFHXFBY-UHFFFAOYSA-N 0.000 description 1
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- LIKZBUYMHLONCD-UHFFFAOYSA-N 5-[[2-[(2-carboxy-4-oxochromen-5-yl)oxymethyl]phenyl]methoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC1=CC=CC=C1COC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 LIKZBUYMHLONCD-UHFFFAOYSA-N 0.000 description 1
- ACXFQGHEJCSWBW-UHFFFAOYSA-N 7-[3-(2-carboxy-6-chloro-4-oxochromen-7-yl)oxy-2-hydroxypropoxy]-6-chloro-4-oxochromene-2-carboxylic acid tetrahydrate Chemical compound O.O.O.O.C(=O)(O)C=1OC2=CC(=C(C=C2C(C1)=O)Cl)OCC(COC1=C(C=C2C(C=C(OC2=C1)C(=O)O)=O)Cl)O ACXFQGHEJCSWBW-UHFFFAOYSA-N 0.000 description 1
- MEXWBXSOBBUPBV-UHFFFAOYSA-N 7-[3-(2-carboxy-8-methyl-4-oxochromen-7-yl)oxy-2-hydroxypropoxy]-8-methyl-4-oxochromene-2-carboxylic acid Chemical compound C1=CC(C(C=C(O2)C(O)=O)=O)=C2C(C)=C1OCC(O)COC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1C MEXWBXSOBBUPBV-UHFFFAOYSA-N 0.000 description 1
- OEKDOSRDAIBBJH-UHFFFAOYSA-N 7-[5-(2-carboxy-4-oxochromen-7-yl)oxypentoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C=2C1=CC(OCCCCCOC1=CC=C3C(=O)C=C(OC3=C1)C(=O)O)=CC=2 OEKDOSRDAIBBJH-UHFFFAOYSA-N 0.000 description 1
- OEXYRGYCZKWBTL-UHFFFAOYSA-N 8-[5-(2-carboxy-4-oxochromen-8-yl)oxypentoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(OCCCCCOC=1C=CC=C3C(=O)C=C(OC3=1)C(=O)O)=CC=C2 OEXYRGYCZKWBTL-UHFFFAOYSA-N 0.000 description 1
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- RNAOSXJVLCYCAY-UHFFFAOYSA-N O.C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCCCCCCCCOC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O Chemical compound O.C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCCCCCCCCOC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O RNAOSXJVLCYCAY-UHFFFAOYSA-N 0.000 description 1
- HEUGIDGLFOQMIK-UHFFFAOYSA-N O.C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCCCOC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O Chemical compound O.C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCCCOC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O HEUGIDGLFOQMIK-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
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- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
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- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 description 1
- 238000011340 continuous therapy Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
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- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
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- 150000002118 epoxides Chemical class 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- CJVFJZNWXDFXHF-UHFFFAOYSA-N ethyl 4-oxochromene-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OCC)=CC(=O)C2=C1 CJVFJZNWXDFXHF-UHFFFAOYSA-N 0.000 description 1
- NIQKXCVMUJFKMK-UHFFFAOYSA-N ethyl 5-[8-(2-ethoxycarbonyl-4-oxochromen-5-yl)oxyoctoxy]-4-oxochromene-2-carboxylate Chemical compound C(C)OC(=O)C=1OC2=CC=CC(=C2C(C1)=O)OCCCCCCCCOC1=C2C(C=C(OC2=CC=C1)C(=O)OCC)=O NIQKXCVMUJFKMK-UHFFFAOYSA-N 0.000 description 1
- ZLAPMSVUFSXCNX-UHFFFAOYSA-N ethyl 6-[5-(2-ethoxycarbonyl-4-oxochromen-6-yl)oxypentoxy]-4-oxochromene-2-carboxylate Chemical compound C(C)OC(=O)C=1OC2=CC=C(C=C2C(C1)=O)OCCCCCOC=1C=C2C(C=C(OC2=CC1)C(=O)OCC)=O ZLAPMSVUFSXCNX-UHFFFAOYSA-N 0.000 description 1
- JLIKLEGJFLYMAX-UHFFFAOYSA-N ethyl 7-[3-(2-ethoxycarbonyl-4-oxochromen-7-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylate Chemical compound C(C)OC(=O)C=1OC2=CC(=CC=C2C(C1)=O)OCC(COC1=CC=C2C(C=C(OC2=C1)C(=O)OCC)=O)O JLIKLEGJFLYMAX-UHFFFAOYSA-N 0.000 description 1
- RKIMFICEWCXBCE-UHFFFAOYSA-N ethyl 7-hydroxy-4-oxochromene-2-carboxylate Chemical compound C1=C(O)C=C2OC(C(=O)OCC)=CC(=O)C2=C1 RKIMFICEWCXBCE-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 231100000037 inhalation toxicity test Toxicity 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000004072 lung Anatomy 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical group [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO373169A NO124994B (nl) | 1965-03-25 | 1969-09-18 |
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12626/65A GB1144905A (en) | 1965-03-25 | 1965-03-25 | Substituted bis-(2-carboxy-chromonyl-oxy) derivatives and preparation and pharmaceutical compositions thereof |
| GB5241465 | 1965-12-09 | ||
| GB5374465 | 1965-12-17 | ||
| NO162258A NO124875B (nl) | 1965-03-25 | 1966-03-23 | |
| GB37765/68A GB1144906A (en) | 1965-03-25 | 1968-08-07 | Bis-phenoxy derivatives |
| DE19691918142 DE1918142A1 (de) | 1969-04-10 | 1969-04-10 | Verfahren zur Herstellung von Bischromonverbindungen |
| DE19691920365 DE1920365A1 (de) | 1969-04-22 | 1969-04-22 | Verfahren zur Herstellung von Bis-Chromonen |
| NO373169A NO124994B (nl) | 1965-03-25 | 1969-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124994B true NO124994B (nl) | 1972-07-03 |
Family
ID=27570483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO373169A NO124994B (nl) | 1965-03-25 | 1969-09-18 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO124994B (nl) |
-
1969
- 1969-09-18 NO NO373169A patent/NO124994B/no unknown
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