NO134462B - - Google Patents
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- Publication number
- NO134462B NO134462B NO4359/70A NO435970A NO134462B NO 134462 B NO134462 B NO 134462B NO 4359/70 A NO4359/70 A NO 4359/70A NO 435970 A NO435970 A NO 435970A NO 134462 B NO134462 B NO 134462B
- Authority
- NO
- Norway
- Prior art keywords
- melting point
- acid
- benzoyl
- acrylic acid
- hydroxycrotonic
- Prior art date
Links
- 239000000446 fuel Substances 0.000 claims 7
- 238000005253 cladding Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 140
- 230000008018 melting Effects 0.000 description 140
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- 150000003946 cyclohexylamines Chemical class 0.000 description 38
- 239000000243 solution Substances 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 24
- 150000002780 morpholines Chemical class 0.000 description 23
- 239000002253 acid Substances 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 19
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000012362 glacial acetic acid Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 11
- -1 nitro, amino, acetylamino, cyan, carbethoxy, methoxy, methylthio, methylsulfinyl Chemical group 0.000 description 11
- TYLDGEVEWDNUTE-ZHACJKMWSA-N (e)-4-hydroxy-4-(4-phenylphenyl)but-2-enoic acid Chemical compound C1=CC(C(\C=C\C(O)=O)O)=CC=C1C1=CC=CC=C1 TYLDGEVEWDNUTE-ZHACJKMWSA-N 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- KFQGOLUWWNZVAS-UHFFFAOYSA-N 4-oxo-4-(4-phenylphenyl)but-2-enoic acid Chemical compound C1=CC(C(=O)C=CC(=O)O)=CC=C1C1=CC=CC=C1 KFQGOLUWWNZVAS-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- 238000001816 cooling Methods 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000000954 anitussive effect Effects 0.000 description 5
- 230000001741 anti-phlogistic effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- RPUDDDLBKGPCAX-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound ClC1=C(C=CC(=C1)Cl)C1=CC=C(C(=O)C=CC(=O)O)C=C1 RPUDDDLBKGPCAX-UHFFFAOYSA-N 0.000 description 3
- YNMZUUYLKMTVQI-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound ClC1=C(C=CC=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 YNMZUUYLKMTVQI-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- XRAVYESZTUBEBU-UHFFFAOYSA-N cyclohexane;propan-2-ol Chemical compound CC(C)O.C1CCCCC1 XRAVYESZTUBEBU-UHFFFAOYSA-N 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RTWLEDIMOQVWDF-IHWYPQMZSA-N (z)-2-hydroxybut-2-enoic acid Chemical class C\C=C(/O)C(O)=O RTWLEDIMOQVWDF-IHWYPQMZSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HNLLCWHRCMJZGB-UHFFFAOYSA-N 1-(3-chloro-4-phenylphenyl)ethanone Chemical compound ClC1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 HNLLCWHRCMJZGB-UHFFFAOYSA-N 0.000 description 2
- QMIUQUBECDHYTN-UHFFFAOYSA-N 4-[3-nitro-4-(4-nitrophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C1=C(C=C(C(=O)C=CC(=O)O)C=C1)[N+](=O)[O-] QMIUQUBECDHYTN-UHFFFAOYSA-N 0.000 description 2
- OUSFIMXENNVNHQ-UHFFFAOYSA-N 4-[4-(2,4-difluorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound FC1=C(C=CC(=C1)F)C1=CC=C(C(=O)C=CC(=O)O)C=C1 OUSFIMXENNVNHQ-UHFFFAOYSA-N 0.000 description 2
- JAVBMOXHZRGPOT-UHFFFAOYSA-N 4-[4-(2-acetamidophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C(C)(=O)NC1=C(C=CC=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 JAVBMOXHZRGPOT-UHFFFAOYSA-N 0.000 description 2
- CGTJIFLHMXDOJD-UHFFFAOYSA-N 4-[4-(2-bromophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound BrC1=C(C=CC=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 CGTJIFLHMXDOJD-UHFFFAOYSA-N 0.000 description 2
- OUTSWRKBWYEWDA-UHFFFAOYSA-N 4-[4-(2-ethoxycarbonylphenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C(=O)(OCC)C1=C(C=CC=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 OUTSWRKBWYEWDA-UHFFFAOYSA-N 0.000 description 2
- CYPQRTFAWYCOQE-UHFFFAOYSA-N 4-[4-(2-fluorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C1=CC(C(=O)C=CC(=O)O)=CC=C1C1=CC=CC=C1F CYPQRTFAWYCOQE-UHFFFAOYSA-N 0.000 description 2
- KKYCCTILMAJAIA-UHFFFAOYSA-N 4-[4-(2-nitrophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 KKYCCTILMAJAIA-UHFFFAOYSA-N 0.000 description 2
- YJTCFWPLBIQMSF-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound ClC=1C=C(C=CC1Cl)C1=CC=C(C(=O)C=CC(=O)O)C=C1 YJTCFWPLBIQMSF-UHFFFAOYSA-N 0.000 description 2
- WZWKTOBSTCAOKM-UHFFFAOYSA-N 4-[4-(3,4-difluorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound FC=1C=C(C=CC1F)C1=CC=C(C(=O)C=CC(=O)O)C=C1 WZWKTOBSTCAOKM-UHFFFAOYSA-N 0.000 description 2
- WKERNLFOUOVZGH-UHFFFAOYSA-N 4-[4-(4-bromophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C1=CC(C(=O)C=CC(=O)O)=CC=C1C1=CC=C(Br)C=C1 WKERNLFOUOVZGH-UHFFFAOYSA-N 0.000 description 2
- PRLVZDMNDNDWDZ-UHFFFAOYSA-N 4-[4-(4-chloro-2-cyanophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound ClC1=CC(=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1)C#N PRLVZDMNDNDWDZ-UHFFFAOYSA-N 0.000 description 2
- QUKAFTFAJMLAMV-UHFFFAOYSA-N 4-[4-(4-chloro-2-fluorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound FC1=C(C=CC(=C1)Cl)C1=CC=C(C(=O)C=CC(=O)O)C=C1 QUKAFTFAJMLAMV-UHFFFAOYSA-N 0.000 description 2
- YXGBLOUADOOFPP-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C1=CC(C(=O)C=CC(=O)O)=CC=C1C1=CC=C(Cl)C=C1 YXGBLOUADOOFPP-UHFFFAOYSA-N 0.000 description 2
- JAMGITPHGTWIGR-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C1=CC(C(=O)C=CC(=O)O)=CC=C1C1=CC=C(F)C=C1 JAMGITPHGTWIGR-UHFFFAOYSA-N 0.000 description 2
- VGEBLZGDXAECLY-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound COC1=CC=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 VGEBLZGDXAECLY-UHFFFAOYSA-N 0.000 description 2
- VVNGTUPHESEYMG-UHFFFAOYSA-N 4-[4-(4-methylsulfanylphenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound CSC1=CC=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 VVNGTUPHESEYMG-UHFFFAOYSA-N 0.000 description 2
- CYLMYJNGOXNZFU-UHFFFAOYSA-N 4-[4-[4-(dimethylcarbamoyl)phenyl]phenyl]-4-oxobut-2-enoic acid Chemical compound CN(C(=O)C1=CC=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1)C CYLMYJNGOXNZFU-UHFFFAOYSA-N 0.000 description 2
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LUKLHGJGFNDQKP-UHFFFAOYSA-N C(C)(=O)NC1=C(C=C(C=C1)Cl)C1=CC=C(C(=O)C=CC(=O)O)C=C1 Chemical compound C(C)(=O)NC1=C(C=C(C=C1)Cl)C1=CC=C(C(=O)C=CC(=O)O)C=C1 LUKLHGJGFNDQKP-UHFFFAOYSA-N 0.000 description 2
- HWVGDTJBHPHIAU-UHFFFAOYSA-N CS(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 Chemical compound CS(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 HWVGDTJBHPHIAU-UHFFFAOYSA-N 0.000 description 2
- TULKFWMTGIYYCT-UHFFFAOYSA-N ClC1=C(C=CC(=C1)F)C1=CC=C(C(=O)C=CC(=O)O)C=C1 Chemical compound ClC1=C(C=CC(=C1)F)C1=CC=C(C(=O)C=CC(=O)O)C=C1 TULKFWMTGIYYCT-UHFFFAOYSA-N 0.000 description 2
- JYQAOTSRQOVUJR-UHFFFAOYSA-N ClC1=C(C=CC=C1Cl)C1=CC=C(C(=O)C=CC(=O)O)C=C1 Chemical compound ClC1=C(C=CC=C1Cl)C1=CC=C(C(=O)C=CC(=O)O)C=C1 JYQAOTSRQOVUJR-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 2
- ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- WSFUIHNEBHEGKR-UHFFFAOYSA-N 1,1'-biphenyl;propan-2-one Chemical class CC(C)=O.C1=CC=CC=C1C1=CC=CC=C1 WSFUIHNEBHEGKR-UHFFFAOYSA-N 0.000 description 1
- VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 1
- VGVXDPRCTIRHOO-UHFFFAOYSA-N 1-(4-amino-3-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C(Cl)=C1 VGVXDPRCTIRHOO-UHFFFAOYSA-N 0.000 description 1
- MTZQSMJVDMLVAV-UHFFFAOYSA-N 1-[4-(2-nitrophenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1[N+]([O-])=O MTZQSMJVDMLVAV-UHFFFAOYSA-N 0.000 description 1
- KLECYOQFQXJYBC-UHFFFAOYSA-N 1-fluoro-2-phenylbenzene Chemical group FC1=CC=CC=C1C1=CC=CC=C1 KLECYOQFQXJYBC-UHFFFAOYSA-N 0.000 description 1
- LXINKRZIJMGCDO-UHFFFAOYSA-N 1-methylsulfanyl-4-phenylbenzene Chemical group C1=CC(SC)=CC=C1C1=CC=CC=C1 LXINKRZIJMGCDO-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical class CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- QZGKXJMNIDWPCN-UHFFFAOYSA-N 2-(4-phenylbenzoyl)prop-2-enoic acid Chemical compound C1(=CC=CC=C1)C1=CC=C(C(=O)C(C(=O)O)=C)C=C1 QZGKXJMNIDWPCN-UHFFFAOYSA-N 0.000 description 1
- QYRDWARBHMCOAG-UHFFFAOYSA-N 2-amino-5-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C=C1C#N QYRDWARBHMCOAG-UHFFFAOYSA-N 0.000 description 1
- RMLONKOSXWOCTC-UHFFFAOYSA-N 4-(2-chloro-4-phenylphenyl)-4-oxobut-2-enoic acid Chemical compound ClC1=C(C(=O)C=CC(=O)O)C=CC(=C1)C1=CC=CC=C1 RMLONKOSXWOCTC-UHFFFAOYSA-N 0.000 description 1
- AAFUDJVNMPTGFJ-UHFFFAOYSA-N 4-(3-chloro-4-phenylphenyl)-4-oxobut-2-enoic acid Chemical compound ClC1=CC(C(=O)C=CC(=O)O)=CC=C1C1=CC=CC=C1 AAFUDJVNMPTGFJ-UHFFFAOYSA-N 0.000 description 1
- IWYDSSXLRFFEIB-UHFFFAOYSA-N 4-[4-(2,5-dichlorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound ClC1=C(C=C(C=C1)Cl)C1=CC=C(C(=O)C=CC(=O)O)C=C1 IWYDSSXLRFFEIB-UHFFFAOYSA-N 0.000 description 1
- GFZZUEPJSWYHEU-UHFFFAOYSA-N 4-[4-(2-carbamoylphenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound NC(=O)C1=C(C=CC=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 GFZZUEPJSWYHEU-UHFFFAOYSA-N 0.000 description 1
- OYVJMPYWEVONFE-UHFFFAOYSA-N 4-[4-(4-acetamidophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C(C)(=O)NC1=CC=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 OYVJMPYWEVONFE-UHFFFAOYSA-N 0.000 description 1
- ZLVPLWSKCHVXGO-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound CC1=C(C=CC(=C1)Cl)C1=CC=C(C(=O)C=CC(=O)O)C=C1 ZLVPLWSKCHVXGO-UHFFFAOYSA-N 0.000 description 1
- YZCBGYJGQUTIIV-UHFFFAOYSA-N 4-[4-(4-chloro-2-nitrophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound ClC1=CC(=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1)[N+](=O)[O-] YZCBGYJGQUTIIV-UHFFFAOYSA-N 0.000 description 1
- UEMYVCOHALNBSP-UHFFFAOYSA-N 4-[4-(4-cyanophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C(#N)C1=CC=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 UEMYVCOHALNBSP-UHFFFAOYSA-N 0.000 description 1
- YDFBFMOQKDSVLV-UHFFFAOYSA-N 4-[4-(4-ethoxycarbonylphenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C(=O)(OCC)C1=CC=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 YDFBFMOQKDSVLV-UHFFFAOYSA-N 0.000 description 1
- VSHOYLJPEZJZTM-UHFFFAOYSA-N 4-[4-(4-methylsulfonylphenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound CS(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 VSHOYLJPEZJZTM-UHFFFAOYSA-N 0.000 description 1
- UYTHJMODQFQZLZ-UHFFFAOYSA-N 4-[4-(4-nitrophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 UYTHJMODQFQZLZ-UHFFFAOYSA-N 0.000 description 1
- HVALFIXHCODMDD-UHFFFAOYSA-N 4-[4-[4-(2-methylpropanoyl)phenyl]phenyl]-4-oxobut-2-enoic acid Chemical compound C(C(C)C)(=O)C1=CC=C(C=C1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 HVALFIXHCODMDD-UHFFFAOYSA-N 0.000 description 1
- CLJZUMXTHGAZOX-UHFFFAOYSA-N 5-chloro-2-phenylbenzonitrile Chemical group N#CC1=CC(Cl)=CC=C1C1=CC=CC=C1 CLJZUMXTHGAZOX-UHFFFAOYSA-N 0.000 description 1
- LGXVUZMDOISZTR-UHFFFAOYSA-N CS(=O)(=O)C=1C=C(C=CC=1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 LGXVUZMDOISZTR-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical class CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- ZDUMOIVDVRFGAQ-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC=C(C(=O)C=CC(=O)O)C=C1 ZDUMOIVDVRFGAQ-UHFFFAOYSA-N 0.000 description 1
- KSZVHVUMUSIKTC-UHFFFAOYSA-N acetic acid;propan-2-one Chemical compound CC(C)=O.CC(O)=O KSZVHVUMUSIKTC-UHFFFAOYSA-N 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- YGHZFEDRNBFOCJ-UHFFFAOYSA-N cyclohexane;propan-1-ol Chemical compound CCCO.C1CCCCC1 YGHZFEDRNBFOCJ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229940032007 methylethyl ketone Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002023 wood 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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19691957750 DE1957750A1 (de) | 1969-11-17 | 1969-11-17 | Neue Hydroxycrotonsaeuren |
DE19702047805 DE2047805A1 (en) | 1970-09-29 | 1970-09-29 | Substd hydroxy crotonic acids |
DE19702047804 DE2047804A1 (en) | 1970-09-29 | 1970-09-29 | Substd hydroxy crotonic acids |
DE19702047802 DE2047802A1 (en) | 1970-09-29 | 1970-09-29 | Substd hydroxy crotonic acids |
DE19702047803 DE2047803A1 (en) | 1970-09-29 | 1970-09-29 | Substd hydroxy crotonic acids |
Publications (2)
Publication Number | Publication Date |
---|---|
NO134462B true NO134462B (zh) | 1976-07-05 |
NO134462C NO134462C (zh) | 1976-10-13 |
Family
ID=27510074
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO4359/70A NO134462C (zh) | 1969-11-17 | 1970-11-16 |
Country Status (18)
Country | Link |
---|---|
US (1) | US3655743A (zh) |
JP (1) | JPS4948311B1 (zh) |
AT (1) | AT303018B (zh) |
BE (1) | BE759053A (zh) |
BG (1) | BG20561A3 (zh) |
CA (1) | CA984408A (zh) |
CH (1) | CH537895A (zh) |
CS (1) | CS178073B2 (zh) |
DK (1) | DK126644B (zh) |
FI (1) | FI52334C (zh) |
FR (1) | FR2073368B1 (zh) |
GB (1) | GB1322370A (zh) |
IE (1) | IE34744B1 (zh) |
IL (1) | IL35656A (zh) |
NL (1) | NL7016745A (zh) |
NO (1) | NO134462C (zh) |
SE (1) | SE360649B (zh) |
SU (1) | SU474134A3 (zh) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2205732A1 (de) * | 1972-02-08 | 1973-08-16 | Thomae Gmbh Dr K | Neue 4-(4-biphenylyl)-butensaeurederivate |
US4070484A (en) * | 1973-01-18 | 1978-01-24 | Kissei Pharmaceutical Co., Ltd. | Antiallergic composition containing aromatic carboxylic amide derivatives and method of using the same |
GB1498903A (en) * | 1974-03-25 | 1978-01-25 | Fabre Sa Pierre | Aromatic keto-acids and their derivatives |
US4096338A (en) * | 1974-07-27 | 1978-06-20 | Nisshin Flour Milling Co., Ltd. | Butenoic and pyruvic acid derivatives |
US4151302A (en) * | 1975-06-28 | 1979-04-24 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Araliphatic dihalogen compounds composition and method of use |
FR2332279A1 (fr) * | 1975-11-19 | 1977-06-17 | Nativelle Sa Ets | Procede d'oxydation des alcaloides du quinquina |
US4239912A (en) * | 1978-12-08 | 1980-12-16 | American Cyanamid Company | Process for resolving DL-Mandelic acid with novel 2-benzylamino-1-butanols |
DE3909378A1 (de) * | 1989-03-22 | 1990-09-27 | Bayer Ag | Substituierte biphenyle |
GB2349880A (en) | 1999-05-10 | 2000-11-15 | Secr Defence | (Thio)morpholinium salts having SHG activity |
WO2007096647A2 (en) * | 2006-02-27 | 2007-08-30 | Sterix Limited | Diaryl compounds as non-steroidal inhibitors of 17-beta hydroxysteroid dehydrogenase and/or steroid sulphatase for the treatment of oestrogen-related diseases such as hormone dependent breast cancer |
-
0
- BE BE759053D patent/BE759053A/xx unknown
-
1970
- 1970-10-26 FI FI702874A patent/FI52334C/fi active
- 1970-11-09 BG BG16005A patent/BG20561A3/xx unknown
- 1970-11-10 DK DK570770AA patent/DK126644B/da unknown
- 1970-11-12 US US88983A patent/US3655743A/en not_active Expired - Lifetime
- 1970-11-12 CH CH1678070A patent/CH537895A/de not_active IP Right Cessation
- 1970-11-13 SU SU1490935A patent/SU474134A3/ru active
- 1970-11-16 JP JP45100955A patent/JPS4948311B1/ja active Pending
- 1970-11-16 NO NO4359/70A patent/NO134462C/no unknown
- 1970-11-16 NL NL7016745A patent/NL7016745A/xx unknown
- 1970-11-16 GB GB5447470A patent/GB1322370A/en not_active Expired
- 1970-11-16 CS CS7726A patent/CS178073B2/cs unknown
- 1970-11-16 IL IL35656A patent/IL35656A/xx unknown
- 1970-11-16 SE SE15497/70A patent/SE360649B/xx unknown
- 1970-11-17 FR FR7041115A patent/FR2073368B1/fr not_active Expired
- 1970-11-17 CA CA098,303A patent/CA984408A/en not_active Expired
- 1970-11-17 IE IE1481/70A patent/IE34744B1/xx unknown
- 1970-11-17 AT AT1036770A patent/AT303018B/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
BG20561A3 (zh) | 1975-12-05 |
IL35656A0 (en) | 1971-01-28 |
SU474134A3 (ru) | 1975-06-14 |
US3655743A (en) | 1972-04-11 |
BE759053A (fr) | 1971-05-17 |
CA984408A (en) | 1976-02-24 |
FI52334C (fi) | 1977-08-10 |
NL7016745A (zh) | 1971-05-19 |
SE360649B (zh) | 1973-10-01 |
AT303018B (de) | 1972-11-10 |
IE34744B1 (en) | 1975-08-06 |
FR2073368A1 (zh) | 1971-10-01 |
CS178073B2 (zh) | 1977-08-31 |
CH537895A (de) | 1973-06-15 |
DK126644B (da) | 1973-08-06 |
GB1322370A (en) | 1973-07-04 |
IL35656A (en) | 1974-03-14 |
FR2073368B1 (zh) | 1974-10-11 |
FI52334B (zh) | 1977-05-02 |
NO134462C (zh) | 1976-10-13 |
IE34744L (en) | 1971-05-17 |
JPS4948311B1 (zh) | 1974-12-20 |
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