CA1071199A - 3-aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters - Google Patents
3-aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid estersInfo
- Publication number
- CA1071199A CA1071199A CA263,850A CA263850A CA1071199A CA 1071199 A CA1071199 A CA 1071199A CA 263850 A CA263850 A CA 263850A CA 1071199 A CA1071199 A CA 1071199A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- oxo
- dimethoxy
- tetrahydro
- group
- 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.)
- Expired
Links
- IIUGXBAMFMNXKK-UHFFFAOYSA-N 3-(aminomethylidene)-6,7-dimethoxy-2-methyl-4-oxo-2h-quinoline-1-carboxylic acid Chemical class OC(=O)N1C(C)C(=CN)C(=O)C2=C1C=C(OC)C(OC)=C2 IIUGXBAMFMNXKK-UHFFFAOYSA-N 0.000 title description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
- -1 mono-substituted 2-ethyl Chemical group 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 abstract description 11
- 150000002148 esters Chemical class 0.000 abstract description 5
- BBESKHDUURDXBF-UHFFFAOYSA-N ethyl 3-(aminomethylidene)-6,7-dimethoxy-2-methyl-4-oxo-2h-quinoline-1-carboxylate Chemical compound COC1=C(OC)C=C2N(C(=O)OCC)C(C)C(=CN)C(=O)C2=C1 BBESKHDUURDXBF-UHFFFAOYSA-N 0.000 abstract description 2
- LVDGCCRBQWLJBX-UHFFFAOYSA-N 3-hydroxy-6,7-dimethoxy-2-methyl-5-methylidene-4-oxo-3,4a-dihydro-2h-quinoline-1-carboxylic acid Chemical compound O=C1C(O)C(C)N(C(O)=O)C2=CC(OC)=C(OC)C(=C)C21 LVDGCCRBQWLJBX-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
- 125000004494 ethyl ester group Chemical group 0.000 description 39
- 239000000243 solution Substances 0.000 description 34
- 239000000047 product Substances 0.000 description 31
- 239000000203 mixture Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
- 239000010410 layer Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 229960003390 magnesium sulfate Drugs 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- MALUFRPCQWHCJQ-UHFFFAOYSA-N 3-(3,4-dimethoxyanilino)butanoic acid Chemical compound COC1=CC=C(NC(C)CC(O)=O)C=C1OC MALUFRPCQWHCJQ-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
- 239000005695 Ammonium acetate Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229940043376 ammonium acetate Drugs 0.000 description 6
- 235000019257 ammonium acetate Nutrition 0.000 description 6
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 6
- MAKGHZBCNKOQFF-UHFFFAOYSA-N ethyl 3-(hydroxymethylidene)-6,7-dimethoxy-2-methyl-4-oxo-2h-quinoline-1-carboxylate Chemical compound COC1=C(OC)C=C2N(C(=O)OCC)C(C)C(=CO)C(=O)C2=C1 MAKGHZBCNKOQFF-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- UYRZHYDGAOZANL-UHFFFAOYSA-N 3-(hydroxymethylidene)-6,7-dimethoxy-2-methyl-4-oxo-2h-quinoline-1-carboxylic acid Chemical compound OC(=O)N1C(C)C(=CO)C(=O)C2=C1C=C(OC)C(OC)=C2 UYRZHYDGAOZANL-UHFFFAOYSA-N 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 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 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 5
- 229960000443 hydrochloric acid Drugs 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical class ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000036647 reaction Effects 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- LGDHZCLREKIGKJ-UHFFFAOYSA-N 3,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C=C1OC LGDHZCLREKIGKJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
- LDWIIYVEWIRGMA-UHFFFAOYSA-N benzyl 6,7-dimethoxy-2-methyl-4-oxo-2,3-dihydroquinoline-1-carboxylate Chemical compound CC1CC(=O)C=2C=C(OC)C(OC)=CC=2N1C(=O)OCC1=CC=CC=C1 LDWIIYVEWIRGMA-UHFFFAOYSA-N 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 230000002301 combined effect Effects 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 1
- GPZTZPMRXFAUNE-UHFFFAOYSA-N 3-(dimethylaminomethylidene)-6,7-dimethoxy-2-methyl-4-oxo-2h-quinoline-1-carboxylic acid Chemical compound OC(=O)N1C(C)C(=CN(C)C)C(=O)C2=C1C=C(OC)C(OC)=C2 GPZTZPMRXFAUNE-UHFFFAOYSA-N 0.000 description 1
- NKOOGKDIFYEYTD-UHFFFAOYSA-N 3-[(benzylamino)methylidene]-6,7-dimethoxy-2-methyl-4-oxo-2h-quinoline-1-carboxylic acid Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2N(C(O)=O)C(C)C1=CNCC1=CC=CC=C1 NKOOGKDIFYEYTD-UHFFFAOYSA-N 0.000 description 1
- CJULYTQCTPLIHS-UHFFFAOYSA-N 3-[[3-(dimethylamino)butylamino]methylidene]-6,7-dimethoxy-2-methyl-4-oxo-2h-quinoline-1-carboxylic acid Chemical compound OC(=O)N1C(C)C(=CNCCC(C)N(C)C)C(=O)C2=C1C=C(OC)C(OC)=C2 CJULYTQCTPLIHS-UHFFFAOYSA-N 0.000 description 1
- UQRYHDWSCGXLGV-UHFFFAOYSA-N 6,7-dimethoxy-2-methyl-3-(methylaminomethylidene)-4-oxo-2h-quinoline-1-carboxylic acid Chemical compound COC1=C(OC)C=C2C(=O)C(=CNC)C(C)N(C(O)=O)C2=C1 UQRYHDWSCGXLGV-UHFFFAOYSA-N 0.000 description 1
- ATMBXBRHCPWCAW-UHFFFAOYSA-N 6,7-dimethoxy-2-methyl-3-[(2-methylbutan-2-ylamino)methylidene]-4-oxo-2h-quinoline-1-carboxylic acid Chemical compound COC1=C(OC)C=C2C(=O)C(=CNC(C)(C)CC)C(C)N(C(O)=O)C2=C1 ATMBXBRHCPWCAW-UHFFFAOYSA-N 0.000 description 1
- FJRPPXDFMSLKEB-UHFFFAOYSA-N 6,7-dimethoxy-2-methyl-4-oxo-2,3-dihydroquinoline-1-carboxylic acid Chemical compound OC(=O)N1C(C)CC(=O)C2=C1C=C(OC)C(OC)=C2 FJRPPXDFMSLKEB-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010013710 Drug interaction Diseases 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 206010029216 Nervousness Diseases 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- YLYXGUOCICLSGX-UHFFFAOYSA-N O=C1CCN(C2=CC=CC=C12)C(=O)O Chemical compound O=C1CCN(C2=CC=CC=C12)C(=O)O YLYXGUOCICLSGX-UHFFFAOYSA-N 0.000 description 1
- 208000000114 Pain Threshold Diseases 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- BIWTUMIDYGEZHH-UHFFFAOYSA-N ethyl 6,7-dimethoxy-2-methyl-4-oxo-2,3-dihydroquinoline-1-carboxylate Chemical compound COC1=C(OC)C=C2N(C(=O)OCC)C(C)CC(=O)C2=C1 BIWTUMIDYGEZHH-UHFFFAOYSA-N 0.000 description 1
- QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GCOWZPRIMFGIDQ-UHFFFAOYSA-N n',n'-dimethylbutane-1,4-diamine Chemical compound CN(C)CCCCN GCOWZPRIMFGIDQ-UHFFFAOYSA-N 0.000 description 1
- 230000001379 nervous effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA327,817A CA1066284A (en) | 1975-11-04 | 1979-05-17 | Process for preparing 3 hydroxy methylene 6,7 dimethoxy-2-methyl-4-oxo 1,2,3,4 tetrahydro 1 quinoline carboxylic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/628,808 US3978064A (en) | 1975-11-04 | 1975-11-04 | 3-Aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters and intermediates leading thereto |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1071199A true CA1071199A (en) | 1980-02-05 |
Family
ID=24520388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA263,850A Expired CA1071199A (en) | 1975-11-04 | 1976-10-21 | 3-aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3978064A (en:Method) |
| JP (1) | JPS5262281A (en:Method) |
| BE (1) | BE847874A (en:Method) |
| CA (1) | CA1071199A (en:Method) |
| DE (2) | DE2647041C2 (en:Method) |
| DK (1) | DK490076A (en:Method) |
| ES (1) | ES452889A1 (en:Method) |
| FR (2) | FR2330398A1 (en:Method) |
| GB (2) | GB1515060A (en:Method) |
| IE (1) | IE43736B1 (en:Method) |
| LU (1) | LU76098A1 (en:Method) |
| NL (1) | NL164034C (en:Method) |
| SE (1) | SE431205B (en:Method) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4260764A (en) * | 1976-12-22 | 1981-04-07 | Pfizer Inc. | 9-Hydroxyoctahydrobenzo [C] quinolines and intermediates therefor |
| US4176191A (en) * | 1977-09-06 | 1979-11-27 | Abbott Laboratories | Aminomethylene oxindoles |
| US4389531A (en) * | 1980-06-12 | 1983-06-21 | Eastman Kodak Company | Preparation of N-substituted anilines |
| US5250691A (en) * | 1991-09-09 | 1993-10-05 | E. R. Squibb & Sons, Inc. | Heteroaryl derivatives of monocyclic beta-lactam antibiotics |
| US8974386B2 (en) | 1998-04-30 | 2015-03-10 | Abbott Diabetes Care Inc. | Analyte monitoring device and methods of use |
| US9066695B2 (en) | 1998-04-30 | 2015-06-30 | Abbott Diabetes Care Inc. | Analyte monitoring device and methods of use |
| US6175752B1 (en) | 1998-04-30 | 2001-01-16 | Therasense, Inc. | Analyte monitoring device and methods of use |
| US8465425B2 (en) | 1998-04-30 | 2013-06-18 | Abbott Diabetes Care Inc. | Analyte monitoring device and methods of use |
| US8226891B2 (en) | 2006-03-31 | 2012-07-24 | Abbott Diabetes Care Inc. | Analyte monitoring devices and methods therefor |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD70880A (en:Method) * | ||||
| US2421693A (en) * | 1944-09-16 | 1947-06-03 | Gen Aniline & Film Corp | Imidazolone color formers |
| US3347856A (en) * | 1965-02-08 | 1967-10-17 | Robins Co Inc A H | 1-lower-alkyl-3-pyrrolidyl nu-loweralkyl- and lower-cycloalkyl-nu-arylcarbamate antispasmodics and antidepressives |
| US3455929A (en) * | 1966-08-15 | 1969-07-15 | Bristol Myers Co | Esters of 1,4-dihydroquinoline-n-carboxylic acids and thione acids |
| AR205807A1 (es) * | 1973-12-26 | 1976-06-07 | Pfizer | Pocedimiento para la preparacion de un nuevo alquil-6, 7-dialcoxi - 2 - metil - 4 - oxotetrahidroquinolina y sus derivados 1-carboxilatos |
-
1975
- 1975-11-04 US US05/628,808 patent/US3978064A/en not_active Expired - Lifetime
-
1976
- 1976-08-13 IE IE1803/76A patent/IE43736B1/en unknown
- 1976-10-15 GB GB1110/78A patent/GB1515060A/en not_active Expired
- 1976-10-15 GB GB43038/76A patent/GB1515059A/en not_active Expired
- 1976-10-19 DE DE2647041A patent/DE2647041C2/de not_active Expired
- 1976-10-19 DE DE2659932A patent/DE2659932C2/de not_active Expired
- 1976-10-21 CA CA263,850A patent/CA1071199A/en not_active Expired
- 1976-10-29 DK DK490076A patent/DK490076A/da not_active Application Discontinuation
- 1976-10-29 FR FR7632866A patent/FR2330398A1/fr active Granted
- 1976-10-29 NL NL7612031.A patent/NL164034C/xx not_active IP Right Cessation
- 1976-10-29 BE BE1007730A patent/BE847874A/xx not_active IP Right Cessation
- 1976-10-29 LU LU76098A patent/LU76098A1/xx unknown
- 1976-10-30 ES ES452889A patent/ES452889A1/es not_active Expired
- 1976-11-01 SE SE7612141A patent/SE431205B/xx unknown
- 1976-11-01 JP JP51131561A patent/JPS5262281A/ja active Granted
-
1977
- 1977-04-07 FR FR7710594A patent/FR2338262A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL7612031A (nl) | 1977-05-06 |
| JPS5510583B2 (en:Method) | 1980-03-17 |
| GB1515059A (en) | 1978-06-21 |
| NL164034C (nl) | 1980-11-17 |
| DE2647041C2 (de) | 1982-07-01 |
| DE2659932C2 (de) | 1982-05-19 |
| SE7612141L (sv) | 1977-07-08 |
| DE2647041A1 (de) | 1977-05-05 |
| LU76098A1 (en:Method) | 1977-05-31 |
| IE43736L (en) | 1977-05-04 |
| BE847874A (fr) | 1977-04-29 |
| FR2330398A1 (fr) | 1977-06-03 |
| ES452889A1 (es) | 1977-12-16 |
| JPS5262281A (en) | 1977-05-23 |
| FR2338262A1 (fr) | 1977-08-12 |
| GB1515060A (en) | 1978-06-21 |
| DK490076A (da) | 1977-05-05 |
| FR2338262B1 (en:Method) | 1980-11-21 |
| IE43736B1 (en) | 1981-05-20 |
| US3978064A (en) | 1976-08-31 |
| SE431205B (sv) | 1984-01-23 |
| NL164034B (nl) | 1980-06-16 |
| FR2330398B1 (en:Method) | 1979-08-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0346208B1 (fr) | Amino-4 quinoléines et naphtyridines, leur procédé de préparation et leur application comme médicaments | |
| CA1242193A (en) | 1-benzyl-aminoalkyl-pyrrolidinones and the acid addition salts thereof, processes for preparing them and pharmaceutical compositions | |
| DD209622A5 (de) | Verfahren zur herstellung von 1,4-dihydropyridinen | |
| LU84099A1 (fr) | Nouveaux derives piperidino,piperazino et homopiperazino,n-substitues par un groupe heterocyclique aromatique,leur procede de preparation et leur application en therapeutique | |
| JPS5989625A (ja) | 芳香族置換環状アミジン止瀉剤 | |
| CA1071199A (en) | 3-aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters | |
| EP1254139B1 (fr) | Derives de 4-heteroaryl-1,4-diazabicyclo 3.2.2]nonane, leur preparation et leur application en therapeutique | |
| US4963558A (en) | Pyrazolo-[3,4-g]isoquinoline derivatives useful to treat CNS disorders | |
| EP0151539A2 (en) | Benzobicyclic lactam acids, their derivatives, an intermediate in the preparation thereof and processes for the production thereof | |
| KR890000864B1 (ko) | 6,7-디히드로-5,8-디메틸-9-플루오로-1-옥소-1H,5H-벤조[ij]퀴놀리진- 2-카르복실산, 그 유도체 및 제조방법 | |
| DD149071A5 (de) | Herstellung 2-substituierter trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu indole | |
| Pierson et al. | Design and synthesis of propranolol analogs as serotonergic agents | |
| US4013662A (en) | Alkyl and benzyl 6,7-dialkoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylates | |
| FI73999C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara piperazinyl-imidazo/4,5-b/- och -/4,5-c/ pyridiner samt mellanprodukt anvaendbar vid det. | |
| EP0119779A1 (en) | 8-Alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acids | |
| GB2120662A (en) | New azepinoindoles, their production and pharmaceutical compositions containing them | |
| JPS5967270A (ja) | イソキノリン誘導体の製法 | |
| EP0178201B1 (fr) | Dérivés de furo [3,2-c]pyridines, leur préparation et leur application en thérapeutique | |
| FR2645743A1 (fr) | Compositions therapeutiques a base de derives di-substitues des n,n(prime)-ditrimethoxybenzoyle piperazines | |
| JPH0543576A (ja) | ２０，２１−ジノルエブルナメニンの新規の誘導体、それらの製造方法及び得られる新規の中間体、それらの薬剤としての使用並びにそれらを含有する組成物 | |
| EP0035820B1 (en) | Novel quinoline derivatives, pharmaceutical compositions containing such compounds, and method for the preparation of these compounds | |
| US4442106A (en) | Quinoline derivatives, pharmaceutical compositions containing such compounds, and methods of treating cardiovascular conditions with them | |
| US4018758A (en) | 3-Aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters and intermediates leading thereto | |
| CA1301171C (en) | 1,12b-disubstituted octahydroindolo ¬2,3-a| quinolizine derivatives, process for their preparation and pharmaceutical compositions containing them | |
| CA1329597C (en) | Derivatives of tetrahydropyrido[1,2-a]indole |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |