FR2487346A1 - Derives de la 4-oximino-1,2,3,4-tetrahydroquinoleine, leur procede de preparation et leur application therapeutique - Google Patents
Derives de la 4-oximino-1,2,3,4-tetrahydroquinoleine, leur procede de preparation et leur application therapeutique Download PDFInfo
- Publication number
- FR2487346A1 FR2487346A1 FR8114436A FR8114436A FR2487346A1 FR 2487346 A1 FR2487346 A1 FR 2487346A1 FR 8114436 A FR8114436 A FR 8114436A FR 8114436 A FR8114436 A FR 8114436A FR 2487346 A1 FR2487346 A1 FR 2487346A1
- Authority
- FR
- France
- Prior art keywords
- tetrahydroquinoline
- group
- oximino
- formula
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- JRAVZISMXMYFRP-UHFFFAOYSA-N N-(2,3-dihydro-1H-quinolin-4-ylidene)hydroxylamine Chemical class C1=CC=C2C(=NO)CCNC2=C1 JRAVZISMXMYFRP-UHFFFAOYSA-N 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 PHENYL GROUP Chemical group 0.000 claims abstract description 13
- 150000002367 halogens Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 230000001882 diuretic effect Effects 0.000 claims description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 239000002934 diuretic Substances 0.000 claims description 5
- 230000001077 hypotensive effect Effects 0.000 claims description 5
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- ABELRHWKDXLRAR-UHFFFAOYSA-N 1-(6-chloro-4-hydroxyimino-2,3-dihydroquinolin-1-yl)propan-1-one Chemical compound ClC1=CC=C2N(C(=O)CC)CCC(=NO)C2=C1 ABELRHWKDXLRAR-UHFFFAOYSA-N 0.000 claims description 2
- FEGWEZYQHKCBKL-UVTDQMKNSA-N 1-[(4z)-6-fluoro-4-hydroxyimino-2,3-dihydroquinolin-1-yl]propan-1-one Chemical compound FC1=CC=C2N(C(=O)CC)CC\C(=N\O)C2=C1 FEGWEZYQHKCBKL-UVTDQMKNSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 3
- BUWPZNOVIHAWHW-UHFFFAOYSA-N 2,3-dihydro-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CCNC2=C1 BUWPZNOVIHAWHW-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 claims 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000021822 hypotensive Diseases 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- IXZVOELNROZATN-LCYFTJDESA-N methyl (4z)-6-fluoro-4-hydroxyimino-2,3-dihydroquinoline-1-carboxylate Chemical compound FC1=CC=C2N(C(=O)OC)CC\C(=N\O)C2=C1 IXZVOELNROZATN-LCYFTJDESA-N 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- 239000013078 crystal Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000000921 elemental analysis Methods 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000005259 measurement Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 150000002923 oximes Chemical class 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 2
- KRGMMKVSHXVQCM-UHFFFAOYSA-N 3,4-dihydro-2h-quinoline-1-carbonyl chloride Chemical compound C1=CC=C2N(C(=O)Cl)CCCC2=C1 KRGMMKVSHXVQCM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WOYMBVUWQFWVSA-UHFFFAOYSA-N 6-chloro-2,3-dihydro-1h-quinolin-4-one Chemical compound N1CCC(=O)C2=CC(Cl)=CC=C21 WOYMBVUWQFWVSA-UHFFFAOYSA-N 0.000 description 2
- FTSMXKUXNFFCGG-UHFFFAOYSA-N 6-fluoro-2,3-dihydro-1h-quinolin-4-one Chemical compound N1CCC(=O)C2=CC(F)=CC=C21 FTSMXKUXNFFCGG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
- 230000009089 cytolysis Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- QARAXUHORATRQJ-UHFFFAOYSA-N 1,4-dioxane;pyridine Chemical compound C1COCCO1.C1=CC=NC=C1 QARAXUHORATRQJ-UHFFFAOYSA-N 0.000 description 1
- UASXSFXMEXUTGN-UHFFFAOYSA-N 1-(3,4-dihydro-2h-quinolin-1-yl)propan-1-one Chemical compound C1=CC=C2N(C(=O)CC)CCCC2=C1 UASXSFXMEXUTGN-UHFFFAOYSA-N 0.000 description 1
- NXXUQBZRZORLTJ-UVTDQMKNSA-N 1-[(4z)-6-bromo-4-hydroxyimino-2,3-dihydroquinolin-1-yl]propan-1-one Chemical compound BrC1=CC=C2N(C(=O)CC)CC\C(=N\O)C2=C1 NXXUQBZRZORLTJ-UVTDQMKNSA-N 0.000 description 1
- XWPGSXMQSZAQLG-PTNGSMBKSA-N 1-[(4z)-6-chloro-4-hydroxyimino-2,3-dihydroquinolin-1-yl]butan-1-one Chemical compound ClC1=CC=C2N(C(=O)CCC)CC\C(=N\O)C2=C1 XWPGSXMQSZAQLG-PTNGSMBKSA-N 0.000 description 1
- OSKWYOOUNSZDBW-UHFFFAOYSA-N 1-acetyl-6-chloro-2,3-dihydroquinolin-4-one Chemical compound ClC1=CC=C2N(C(=O)C)CCC(=O)C2=C1 OSKWYOOUNSZDBW-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ZAFBGRNWOGKKSP-UHFFFAOYSA-N 3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N)CCCC2=C1 ZAFBGRNWOGKKSP-UHFFFAOYSA-N 0.000 description 1
- KJUKZULKWZBJTH-UHFFFAOYSA-N 6-chloro-4-oxo-2,3-dihydroquinoline-1-carbaldehyde Chemical compound O=CN1CCC(=O)C2=CC(Cl)=CC=C21 KJUKZULKWZBJTH-UHFFFAOYSA-N 0.000 description 1
- XKTRJFHFYUJRFG-UHFFFAOYSA-N 6-chloro-4-oxo-2,3-dihydroquinoline-1-carbonyl chloride Chemical compound ClC1=CC=C2N(C(=O)Cl)CCC(=O)C2=C1 XKTRJFHFYUJRFG-UHFFFAOYSA-N 0.000 description 1
- KCEKQJOLQHOQRE-UHFFFAOYSA-N 6-fluoro-4-hydroxyimino-2,3-dihydroquinoline-1-carbaldehyde Chemical compound C1=C(F)C=C2C(=NO)CCN(C=O)C2=C1 KCEKQJOLQHOQRE-UHFFFAOYSA-N 0.000 description 1
- JDDSAQQFCKTOJF-UHFFFAOYSA-N 6-fluoro-4-oxo-2,3-dihydroquinoline-1-carbonyl chloride Chemical compound ClC(=O)N1CCC(=O)C2=CC(F)=CC=C21 JDDSAQQFCKTOJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 240000006240 Linum usitatissimum Species 0.000 description 1
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007083 alkoxycarbonylation reaction Methods 0.000 description 1
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- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 238000006482 condensation reaction Methods 0.000 description 1
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- 230000018044 dehydration Effects 0.000 description 1
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- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
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- 238000009472 formulation Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- POCUPXSSKQAQRY-UHFFFAOYSA-N hydroxylamine;hydrate Chemical compound O.ON POCUPXSSKQAQRY-UHFFFAOYSA-N 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 235000021027 japanese diet Nutrition 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- MYOLFGKGSLHSOH-LCYFTJDESA-N methyl (4z)-6-bromo-4-hydroxyimino-2,3-dihydroquinoline-1-carboxylate Chemical compound BrC1=CC=C2N(C(=O)OC)CC\C(=N\O)C2=C1 MYOLFGKGSLHSOH-LCYFTJDESA-N 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
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- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- CCVKPWUMYBYHCD-UHFFFAOYSA-N oxolane;pyridine Chemical compound C1CCOC1.C1=CC=NC=C1 CCVKPWUMYBYHCD-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10327280A JPS5728052A (en) | 1980-07-28 | 1980-07-28 | Novel 4-hydroxyimino-1,2,3,4-tetrahydroquinoline derivative |
| JP3991081A JPS57154168A (en) | 1981-03-19 | 1981-03-19 | Novel 4-oximino-1,2,3,4-tetrahydroquinoline derivative |
| JP3991181A JPS57154169A (en) | 1981-03-19 | 1981-03-19 | Novel 4-oximino-1,2,3,4-tetrahydroquinoline derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2487346A1 true FR2487346A1 (fr) | 1982-01-29 |
| FR2487346B1 FR2487346B1 (enrdf_load_stackoverflow) | 1984-12-28 |
Family
ID=27290305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8114436A Granted FR2487346A1 (fr) | 1980-07-28 | 1981-07-24 | Derives de la 4-oximino-1,2,3,4-tetrahydroquinoleine, leur procede de preparation et leur application therapeutique |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE3129718A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2487346A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2092130B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2552430A1 (fr) * | 1983-09-22 | 1985-03-29 | Rhone Poulenc Sante | Procede de preparation de quinolinones-4 |
| EP0243982A1 (en) | 1986-05-02 | 1987-11-04 | Mochida Pharmaceutical Co., Ltd. | 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivative, process for the production thereof, pharmaceutical composition and intermediates |
| US4968680A (en) * | 1987-10-31 | 1990-11-06 | Mochida Pharmaceutical Co., Ltd. | 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives, process for producing them and use thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6160682A (ja) * | 1984-08-30 | 1986-03-28 | Nippon Tokushu Noyaku Seizo Kk | テトラヒドロキノリン−１−イルカルボニルイミダゾ−ル誘導体、その中間体、それらの製法並びに除草又は農園芸用殺菌剤 |
| US8697674B2 (en) | 2004-12-29 | 2014-04-15 | Naturon, Inc. | Xanthurenic acid derivative pharmaceutical compositions and methods related thereto |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3075984A (en) * | 1958-05-09 | 1963-01-29 | Sterling Drug Inc | 1-[(lower-aromatic)-(lower-alkyl)]-4-[(lower-aromatic)-(lower-alkyl) imino]-1, 4-dihydroquinolines and their preparation |
| US3406176A (en) * | 1964-08-24 | 1968-10-15 | Sterling Drug Inc | 7-halo-4-carbamylimino-1, 4-dihydroquinolines |
-
1981
- 1981-07-07 GB GB8120931A patent/GB2092130B/en not_active Expired
- 1981-07-24 FR FR8114436A patent/FR2487346A1/fr active Granted
- 1981-07-28 DE DE19813129718 patent/DE3129718A1/de active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3075984A (en) * | 1958-05-09 | 1963-01-29 | Sterling Drug Inc | 1-[(lower-aromatic)-(lower-alkyl)]-4-[(lower-aromatic)-(lower-alkyl) imino]-1, 4-dihydroquinolines and their preparation |
| US3406176A (en) * | 1964-08-24 | 1968-10-15 | Sterling Drug Inc | 7-halo-4-carbamylimino-1, 4-dihydroquinolines |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2552430A1 (fr) * | 1983-09-22 | 1985-03-29 | Rhone Poulenc Sante | Procede de preparation de quinolinones-4 |
| EP0140748A1 (fr) * | 1983-09-22 | 1985-05-08 | Rhone-Poulenc Sante | Procédé de préparation de quinolinones-4 |
| EP0243982A1 (en) | 1986-05-02 | 1987-11-04 | Mochida Pharmaceutical Co., Ltd. | 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivative, process for the production thereof, pharmaceutical composition and intermediates |
| WO1987006580A1 (en) * | 1986-05-02 | 1987-11-05 | Mochida Pharmaceutical Co., Ltd. | 1-acyl-2,3-dihydro-4(1h)-quinolinone-4-oxime derivatives |
| US4839368A (en) * | 1986-05-02 | 1989-06-13 | Mochida Pharmaceutical Co., Ltd. | 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives |
| US5077410A (en) * | 1986-05-02 | 1991-12-31 | Mochida Pharmaceutical Co., Ltd. | Intermediate compounds of 1-acyl-2,3-dihydro-4(1h)-quinolinone-4-oxime derivatives |
| US4968680A (en) * | 1987-10-31 | 1990-11-06 | Mochida Pharmaceutical Co., Ltd. | 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives, process for producing them and use thereof |
| EP0315115A3 (en) * | 1987-10-31 | 1991-02-27 | Mochida Pharmaceutical Co., Ltd. | 1-acyl-2,3-dihydro-4(1h)-quinolinone-4-oxime derivatives, process for producing them and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2092130A (en) | 1982-08-11 |
| FR2487346B1 (enrdf_load_stackoverflow) | 1984-12-28 |
| DE3129718C2 (enrdf_load_stackoverflow) | 1988-08-18 |
| GB2092130B (en) | 1984-05-10 |
| DE3129718A1 (de) | 1982-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |