DE2647041C2 - 3-Aminomethylen-6,7-dimethoxy-2- methyl-4-oxo-1,2,3,4-tetrahydro-1-chinolincarbonsäureäthylester - Google Patents
3-Aminomethylen-6,7-dimethoxy-2- methyl-4-oxo-1,2,3,4-tetrahydro-1-chinolincarbonsäureäthylesterInfo
- Publication number
- DE2647041C2 DE2647041C2 DE2647041A DE2647041A DE2647041C2 DE 2647041 C2 DE2647041 C2 DE 2647041C2 DE 2647041 A DE2647041 A DE 2647041A DE 2647041 A DE2647041 A DE 2647041A DE 2647041 C2 DE2647041 C2 DE 2647041C2
- Authority
- DE
- Germany
- Prior art keywords
- dimethoxy
- methyl
- oxo
- tetrahydro
- aminomethylene
- 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
- 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 title claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- 230000008018 melting Effects 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- -1 alkyl acetoacetate Chemical compound 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000282412 Homo Species 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000000202 analgesic effect Effects 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 230000035939 shock Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 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 5
- 241000700159 Rattus Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- HQONJNNQULEVQJ-UHFFFAOYSA-N 6,7-dimethoxy-2-methyl-2,3-dihydro-1h-quinolin-4-one Chemical compound N1C(C)CC(=O)C2=C1C=C(OC)C(OC)=C2 HQONJNNQULEVQJ-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 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 4
- 238000000034 method Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 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 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 238000000746 purification Methods 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 230000009191 jumping Effects 0.000 description 2
- OSHMUXCQPAEJLB-UHFFFAOYSA-N methyl 4-oxo-2,3-dihydroquinoline-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)CCC(=O)C2=C1 OSHMUXCQPAEJLB-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification 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
- 230000035945 sensitivity Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- 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 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010028347 Muscle twitching Diseases 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 208000000114 Pain Threshold Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 229920002472 Starch Polymers 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MBHFIOOFCDTZMD-UHFFFAOYSA-N ethyl 3-(3,4-dimethoxyanilino)but-2-enoate Chemical compound CCOC(=O)C=C(C)NC1=CC=C(OC)C(OC)=C1 MBHFIOOFCDTZMD-UHFFFAOYSA-N 0.000 description 1
- PVELCDFGBLEXRI-UHFFFAOYSA-N ethyl 3-(3,4-dimethoxyanilino)butanoate Chemical compound CCOC(=O)CC(C)NC1=CC=C(OC)C(OC)=C1 PVELCDFGBLEXRI-UHFFFAOYSA-N 0.000 description 1
- VMQCBLAYEOHDGR-UHFFFAOYSA-N ethyl 6,7-dimethoxy-2-methyl-3-[(1-naphthalen-1-ylethylamino)methylidene]-4-oxo-2h-quinoline-1-carboxylate Chemical compound O=C1C2=CC(OC)=C(OC)C=C2N(C(=O)OCC)C(C)C1=CNC(C)C1=CC=CC2=CC=CC=C12 VMQCBLAYEOHDGR-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase 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
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing 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)
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 (2)
| Publication Number | Publication Date |
|---|---|
| DE2647041A1 DE2647041A1 (de) | 1977-05-05 |
| DE2647041C2 true DE2647041C2 (de) | 1982-07-01 |
Family
ID=24520388
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2647041A Expired DE2647041C2 (de) | 1975-11-04 | 1976-10-19 | 3-Aminomethylen-6,7-dimethoxy-2- methyl-4-oxo-1,2,3,4-tetrahydro-1-chinolincarbonsäureäthylester |
| DE2659932A Expired DE2659932C2 (de) | 1975-11-04 | 1976-10-19 | Racemischer 3-Hydroxymethylen-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-chinolincarbonsäureäthylester |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2659932A Expired DE2659932C2 (de) | 1975-11-04 | 1976-10-19 | Racemischer 3-Hydroxymethylen-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-chinolincarbonsäureäthylester |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3978064A (show.php) |
| JP (1) | JPS5262281A (show.php) |
| BE (1) | BE847874A (show.php) |
| CA (1) | CA1071199A (show.php) |
| DE (2) | DE2647041C2 (show.php) |
| DK (1) | DK490076A (show.php) |
| ES (1) | ES452889A1 (show.php) |
| FR (2) | FR2330398A1 (show.php) |
| GB (2) | GB1515060A (show.php) |
| IE (1) | IE43736B1 (show.php) |
| LU (1) | LU76098A1 (show.php) |
| NL (1) | NL164034C (show.php) |
| SE (1) | SE431205B (show.php) |
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 (show.php) * | ||||
| 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 (show.php) | 1980-03-17 |
| GB1515059A (en) | 1978-06-21 |
| NL164034C (nl) | 1980-11-17 |
| DE2659932C2 (de) | 1982-05-19 |
| SE7612141L (sv) | 1977-07-08 |
| CA1071199A (en) | 1980-02-05 |
| DE2647041A1 (de) | 1977-05-05 |
| LU76098A1 (show.php) | 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 (show.php) | 1980-11-21 |
| IE43736B1 (en) | 1981-05-20 |
| US3978064A (en) | 1976-08-31 |
| SE431205B (sv) | 1984-01-23 |
| NL164034B (nl) | 1980-06-16 |
| FR2330398B1 (show.php) | 1979-08-17 |
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