SU978727A3 - Способ получени производных хинолинкарбоновой кислоты - Google Patents
Способ получени производных хинолинкарбоновой кислоты Download PDFInfo
- Publication number
- SU978727A3 SU978727A3 SU802968349A SU2968349A SU978727A3 SU 978727 A3 SU978727 A3 SU 978727A3 SU 802968349 A SU802968349 A SU 802968349A SU 2968349 A SU2968349 A SU 2968349A SU 978727 A3 SU978727 A3 SU 978727A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mixture
- carboxylic acid
- piperazinyl
- dihydro
- methyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 6
- 239000002253 acid Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title abstract description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 2
- -1 1- piperazinyl Chemical group 0.000 claims abstract description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 241000192125 Firmicutes Species 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 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
- IAKNLKLKKBPMHN-UHFFFAOYSA-N 4h-quinolizine-2-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CCN21 IAKNLKLKKBPMHN-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004280 Sodium formate Substances 0.000 description 3
- ZGRIMGHOFDEZLG-UHFFFAOYSA-N ethyl 8-chloro-6,7-difluoro-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(C)OC(=O)C1=CNC2=C(C(=C(C=C2C1=O)F)F)Cl ZGRIMGHOFDEZLG-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 3
- 235000019254 sodium formate Nutrition 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- ABQYZRZVRIPTPI-UHFFFAOYSA-N miloxacin Chemical compound C1=C2N(OC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 ABQYZRZVRIPTPI-UHFFFAOYSA-N 0.000 description 2
- 229950007835 miloxacin Drugs 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UWPUJVOSEQMMQE-UHFFFAOYSA-N 1-bromo-4,5-difluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=C(F)C=C1Br UWPUJVOSEQMMQE-UHFFFAOYSA-N 0.000 description 1
- UKKFELITTUIEND-UHFFFAOYSA-N 2-chloro-3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1Cl UKKFELITTUIEND-UHFFFAOYSA-N 0.000 description 1
- XISDPHXOJCIPHX-UHFFFAOYSA-N 2-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N=C1N1CCNCC1 XISDPHXOJCIPHX-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 1
- FQTGBHZZNVFFFM-UHFFFAOYSA-N 4h-quinolizine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(C(=O)O)=CCN21 FQTGBHZZNVFFFM-UHFFFAOYSA-N 0.000 description 1
- UQKAMONIMDBCIM-UHFFFAOYSA-N 5,6-difluoro-2-methylquinoline Chemical compound FC1=C(F)C=CC2=NC(C)=CC=C21 UQKAMONIMDBCIM-UHFFFAOYSA-N 0.000 description 1
- SLQILVJIQAIJGP-UHFFFAOYSA-N 8-bromo-5,6-difluoro-2-methyl-1H-quinolin-4-one Chemical compound BrC=1C=C(C(=C2C(=CC(=NC12)C)O)F)F SLQILVJIQAIJGP-UHFFFAOYSA-N 0.000 description 1
- GHHJVASDDBUKCH-UHFFFAOYSA-N 8-chloro-1-ethyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(F)C(Cl)=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 GHHJVASDDBUKCH-UHFFFAOYSA-N 0.000 description 1
- FBQWOQWRZBZQDO-UHFFFAOYSA-N 8-chloro-1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.ClC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 FBQWOQWRZBZQDO-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 240000002329 Inga feuillei Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- SWJBITNFDYHWBU-UHFFFAOYSA-N [I].[I] Chemical compound [I].[I] SWJBITNFDYHWBU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- IMCCZKHIPVEUEI-UHFFFAOYSA-N n,n-difluoroaniline Chemical compound FN(F)C1=CC=CC=C1 IMCCZKHIPVEUEI-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10677679A JPS5630964A (en) | 1979-08-22 | 1979-08-22 | Novel substituted quinolinecarboxylic acid and its preparation |
| BE2/58706A BE884824A (fr) | 1979-08-22 | 1980-08-19 | Derives de l'acide quinoleine-carboxylique et procede pour leur preparation |
| BE2059018 | 1981-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU978727A3 true SU978727A3 (ru) | 1982-11-30 |
Family
ID=27159608
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802968349A SU978727A3 (ru) | 1979-08-22 | 1980-08-21 | Способ получени производных хинолинкарбоновой кислоты |
| SU813254244A SU1015827A3 (ru) | 1979-08-22 | 1981-03-03 | Способ получени производных хинолинкарбоновой кислоты или их гидратов |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813254244A SU1015827A3 (ru) | 1979-08-22 | 1981-03-03 | Способ получени производных хинолинкарбоновой кислоты или их гидратов |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5630964A (fr) |
| AU (1) | AU533141B2 (fr) |
| BE (2) | BE884824A (fr) |
| CA (1) | CA1159454A (fr) |
| CH (1) | CH645641A5 (fr) |
| DE (1) | DE3031767C3 (fr) |
| ES (1) | ES8104233A1 (fr) |
| FR (1) | FR2463771A1 (fr) |
| GB (1) | GB2057440B (fr) |
| HK (1) | HK98486A (fr) |
| HU (1) | HU184817B (fr) |
| IT (1) | IT1132392B (fr) |
| MY (1) | MY8700155A (fr) |
| SE (1) | SE440353B (fr) |
| SG (1) | SG71386G (fr) |
| SU (2) | SU978727A3 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2514937C2 (ru) * | 2008-08-06 | 2014-05-10 | Байомарин Фармасьютикалз Инк. | Дигидропиридофталазиноновые ингибиторы поли(адф-рибоза)полимеразы |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4416884A (en) * | 1978-04-12 | 1983-11-22 | Otsuka Pharmaceutical Co., Ltd. | Piperazinylbenzoheterocyclic compounds |
| NO156828C (no) * | 1980-11-10 | 1987-12-02 | Otsuka Pharma Co Ltd | Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser. |
| JPS57176987A (en) * | 1981-04-24 | 1982-10-30 | Otsuka Pharmaceut Co Ltd | Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7101049A (fr) * | 1970-01-28 | 1971-07-30 | ||
| BE793524A (fr) * | 1971-12-30 | 1973-06-29 | Riker Laboratories Inc | Acides benzoquinolizine-carboxyliques et leurs derives |
| US4156726A (en) * | 1974-12-07 | 1979-05-29 | Fisons Limited | 4-Oxo-2-carboxyl quinoline derivatives used as antiallergic compounds |
| JPS53141286A (en) * | 1977-05-16 | 1978-12-08 | Kyorin Seiyaku Kk | Novel substituted quinolinecarboxylic acid |
| JPS54112877A (en) | 1978-02-20 | 1979-09-04 | Sumitomo Chem Co Ltd | Preparation of 1-substituted-1,4-dihydro-4-oxo-3-pyridine carboxylic acid derivatives |
| DE2914258A1 (de) * | 1978-04-12 | 1979-10-25 | Otsuka Pharma Co Ltd | Piperazinylbenzoheterozyklische verbindungen, verfahren zu deren herstellung und mittel, welche diese enthalten |
| AU553415B2 (en) * | 1983-09-19 | 1986-07-17 | Abbott Japan Co., Ltd. | 6-fluoro-1-4-dihydro-4-oxo-7-substituted piperazinyl- quinoline-3-carboxylic acids |
-
1979
- 1979-08-22 JP JP10677679A patent/JPS5630964A/ja active Pending
-
1980
- 1980-08-04 SE SE8005534A patent/SE440353B/sv not_active IP Right Cessation
- 1980-08-06 AU AU61122/80A patent/AU533141B2/en not_active Expired
- 1980-08-11 IT IT24111/80A patent/IT1132392B/it active
- 1980-08-14 CH CH614680A patent/CH645641A5/de not_active IP Right Cessation
- 1980-08-19 ES ES494352A patent/ES8104233A1/es not_active Expired
- 1980-08-19 BE BE2/58706A patent/BE884824A/fr not_active IP Right Cessation
- 1980-08-21 FR FR8018279A patent/FR2463771A1/fr active Granted
- 1980-08-21 HU HU802072A patent/HU184817B/hu unknown
- 1980-08-21 CA CA000358778A patent/CA1159454A/fr not_active Expired
- 1980-08-21 SU SU802968349A patent/SU978727A3/ru active
- 1980-08-22 GB GB8027372A patent/GB2057440B/en not_active Expired
- 1980-08-22 DE DE3031767A patent/DE3031767C3/de not_active Expired - Lifetime
-
1981
- 1981-02-19 BE BE2/59018A patent/BE887574R/fr not_active IP Right Cessation
- 1981-03-03 SU SU813254244A patent/SU1015827A3/ru active
-
1986
- 1986-09-04 SG SG713/86A patent/SG71386G/en unknown
- 1986-12-18 HK HK984/86A patent/HK98486A/xx not_active IP Right Cessation
-
1987
- 1987-12-30 MY MY155/87A patent/MY8700155A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2514937C2 (ru) * | 2008-08-06 | 2014-05-10 | Байомарин Фармасьютикалз Инк. | Дигидропиридофталазиноновые ингибиторы поли(адф-рибоза)полимеразы |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1132392B (it) | 1986-07-02 |
| DE3031767C2 (fr) | 1994-04-14 |
| SG71386G (en) | 1987-03-27 |
| CA1159454A (fr) | 1983-12-27 |
| DE3031767A1 (de) | 1981-03-26 |
| AU6112280A (en) | 1981-02-26 |
| FR2463771A1 (fr) | 1981-02-27 |
| ES494352A0 (es) | 1981-04-16 |
| MY8700155A (en) | 1987-12-31 |
| HK98486A (en) | 1986-12-24 |
| HU184817B (en) | 1984-10-29 |
| SU1015827A3 (ru) | 1983-04-30 |
| AU533141B2 (en) | 1983-11-03 |
| DE3031767C3 (de) | 1994-04-14 |
| IT8024111A0 (it) | 1980-08-11 |
| GB2057440A (en) | 1981-04-01 |
| BE884824A (fr) | 1980-12-16 |
| JPS5630964A (en) | 1981-03-28 |
| ES8104233A1 (es) | 1981-04-16 |
| BE887574R (fr) | 1981-06-15 |
| FR2463771B1 (fr) | 1983-04-22 |
| GB2057440B (en) | 1983-10-12 |
| SE8005534L (sv) | 1981-02-23 |
| CH645641A5 (de) | 1984-10-15 |
| SE440353B (sv) | 1985-07-29 |
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