NO771771L - Fremgangsm}te for fremstilling av nye derivater av dibenzo(de, h)kinolin - Google Patents
Fremgangsm}te for fremstilling av nye derivater av dibenzo(de, h)kinolinInfo
- Publication number
- NO771771L NO771771L NO771771A NO771771A NO771771L NO 771771 L NO771771 L NO 771771L NO 771771 A NO771771 A NO 771771A NO 771771 A NO771771 A NO 771771A NO 771771 L NO771771 L NO 771771L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- symbols
- hydrogen atom
- denotes
- Prior art date
Links
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- 230000036961 partial effect Effects 0.000 claims description 8
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000001914 filtration Methods 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 239000012153 distilled water Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000013078 crystal Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 238000001816 cooling Methods 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- -1 ethanol Chemical compound 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 241000700605 Viruses Species 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- INSNNVNWDYCOBU-UHFFFAOYSA-N 1-azabenzanthrone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=NC=CC2=C1 INSNNVNWDYCOBU-UHFFFAOYSA-N 0.000 description 3
- DCKOIWWWWGUYTD-UHFFFAOYSA-N 10,11-dimethoxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinoline Chemical compound C1CC2=CC=CC=C2C2N1CC1=C2C=C(OC)C(OC)=C1 DCKOIWWWWGUYTD-UHFFFAOYSA-N 0.000 description 3
- BXGDZRKMVQJADW-UHFFFAOYSA-N 4,5-dimethoxy-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one Chemical compound C1=NC(C2=C(C=C(C(=C2)OC)OC)C2=O)=C3C2=CC=CC3=C1 BXGDZRKMVQJADW-UHFFFAOYSA-N 0.000 description 3
- PIWFICNYMFBNJD-UHFFFAOYSA-N 4,5-dimethoxy-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17)-heptaen-8-one Chemical compound O=C1C(C2=3)=CC=CC=3CCN=C2C2=C1C=C(OC)C(OC)=C2 PIWFICNYMFBNJD-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- YMVFYEQDXUWNFJ-UHFFFAOYSA-N ethyl (5,6-dihydro-4h-dibenzo[de,h]quinol-7-yloxy)acetate Chemical compound C12=CC=CC=C2C(OCC(=O)OCC)=C2C3=C1N=CC=C3CCC2 YMVFYEQDXUWNFJ-UHFFFAOYSA-N 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- PVMAYYRJBKHIJA-UHFFFAOYSA-N methyl 2-(3,4-dihydroisoquinolin-1-yl)-4,5-dimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C=C1C1=NCCC2=CC=CC=C12 PVMAYYRJBKHIJA-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MBYLNRRTUYQZAW-UHFFFAOYSA-N 2-(2-phenylethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC1=CC=CC=C1 MBYLNRRTUYQZAW-UHFFFAOYSA-N 0.000 description 2
- ITTMKMBRJJZVNE-UHFFFAOYSA-N 5,6-dimethoxy-2-(2-phenylethyl)isoindole-1,3-dione Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2C(=O)N1CCC1=CC=CC=C1 ITTMKMBRJJZVNE-UHFFFAOYSA-N 0.000 description 2
- WVCHRBVAXLHOGH-UHFFFAOYSA-N 7-hydroxy-5,6-dihydro-4h-dibenzo[de,h]quinoline Chemical compound C12=CC=CC=C2C(O)=C2C3=C1N=CC=C3CCC2 WVCHRBVAXLHOGH-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000430519 Human rhinovirus sp. Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000120 cytopathologic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- ZIXWTPREILQLAC-UHFFFAOYSA-N isoquinolin-8-ol Chemical compound C1=NC=C2C(O)=CC=CC2=C1 ZIXWTPREILQLAC-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NSFIKWRNYAOJET-UHFFFAOYSA-N 12b-hydroxy-10,11-dimethoxy-5,6-dihydroisoindolo[1,2-a]isoquinolin-8-one Chemical compound C1CC2=CC=CC=C2C2(O)N1C(=O)C1=C2C=C(OC)C(OC)=C1 NSFIKWRNYAOJET-UHFFFAOYSA-N 0.000 description 1
- MVDMFDJDEZOXOV-UHFFFAOYSA-N 2-(16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,8,13(17),14-heptaen-8-yloxy)acetic acid Chemical compound C12=CC=CC=C2C(OCC(=O)O)=C2C3=C1N=CC=C3CCC2 MVDMFDJDEZOXOV-UHFFFAOYSA-N 0.000 description 1
- 241000711573 Coronaviridae Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000709661 Enterovirus Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 125000000773 L-serino group Chemical group [H]OC(=O)[C@@]([H])(N([H])*)C([H])([H])O[H] 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- 241001275117 Seres Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000065 noncytotoxic Toxicity 0.000 description 1
- 230000002020 noncytotoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C07D209/49—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (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)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7615379A FR2351656A1 (fr) | 1976-05-21 | 1976-05-21 | Nouveaux derives de la dibenzo(de, h) quinoleine, leur preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO771771L true NO771771L (no) | 1977-11-22 |
Family
ID=9173467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO771771A NO771771L (no) | 1976-05-21 | 1977-05-20 | Fremgangsm}te for fremstilling av nye derivater av dibenzo(de, h)kinolin |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4128650A (fr) |
| JP (1) | JPS52142074A (fr) |
| AU (1) | AU507900B2 (fr) |
| BE (1) | BE854869A (fr) |
| CA (1) | CA1073912A (fr) |
| CH (1) | CH625225A5 (fr) |
| DE (1) | DE2722773A1 (fr) |
| DK (1) | DK217477A (fr) |
| FI (1) | FI771613A (fr) |
| FR (1) | FR2351656A1 (fr) |
| GB (1) | GB1530438A (fr) |
| HU (1) | HU173385B (fr) |
| NL (1) | NL7705337A (fr) |
| NO (1) | NO771771L (fr) |
| SE (1) | SE7705853L (fr) |
| ZA (1) | ZA772986B (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3143876A1 (de) * | 1981-11-05 | 1983-05-11 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue1-furyl-3,4-dihydroisochinoline diese enthaltende arzneimittel sowie verfahren zu deren herstellung und deren verwendung |
| US5298509A (en) * | 1992-09-25 | 1994-03-29 | New York University | Octahydronaphthoquinolizines, and methods of making and using thereof |
| WO1998018764A1 (fr) * | 1996-10-28 | 1998-05-07 | Merck Patent Gmbh | Dihydrobenzoanthracenone, -pyrimidinone ou dihydroanphtoquinolinone |
| DE10345572A1 (de) * | 2003-09-29 | 2005-05-19 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
| US20050113246A1 (en) * | 2003-11-06 | 2005-05-26 | The Procter & Gamble Company | Process of producing an organic catalyst |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2086704A (en) * | 1933-11-29 | 1937-07-13 | Gen Aniline Works Inc | Compounds of the azabenzanthrone series |
| US3717643A (en) * | 1967-05-04 | 1973-02-20 | Sterling Drug Inc | N-substituted-norapomorphines |
| DE1569606C3 (de) * | 1967-09-04 | 1974-12-05 | Bayer Ag, 5090 Leverkusen | Basische Farbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| US3673189A (en) * | 1971-01-05 | 1972-06-27 | American Cyanamid Co | Tetracyclic isoquinoline derivatives |
-
1976
- 1976-05-21 FR FR7615379A patent/FR2351656A1/fr active Granted
-
1977
- 1977-05-13 NL NL7705337A patent/NL7705337A/xx not_active Application Discontinuation
- 1977-05-17 SE SE7705853A patent/SE7705853L/xx unknown
- 1977-05-18 ZA ZA00772986A patent/ZA772986B/xx unknown
- 1977-05-18 JP JP5653777A patent/JPS52142074A/ja active Pending
- 1977-05-18 GB GB20969/77A patent/GB1530438A/en not_active Expired
- 1977-05-18 US US05/798,139 patent/US4128650A/en not_active Expired - Lifetime
- 1977-05-18 AU AU25250/77A patent/AU507900B2/en not_active Expired
- 1977-05-18 DK DK217477A patent/DK217477A/da unknown
- 1977-05-19 HU HU77RO929A patent/HU173385B/hu unknown
- 1977-05-20 DE DE19772722773 patent/DE2722773A1/de not_active Withdrawn
- 1977-05-20 CH CH624277A patent/CH625225A5/fr not_active IP Right Cessation
- 1977-05-20 FI FI771613A patent/FI771613A/fi not_active Application Discontinuation
- 1977-05-20 CA CA278,864A patent/CA1073912A/fr not_active Expired
- 1977-05-20 BE BE177769A patent/BE854869A/fr unknown
- 1977-05-20 NO NO771771A patent/NO771771L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE854869A (fr) | 1977-11-21 |
| HU173385B (hu) | 1979-04-28 |
| GB1530438A (en) | 1978-11-01 |
| FI771613A (fr) | 1977-11-22 |
| DE2722773A1 (de) | 1977-12-08 |
| SE7705853L (sv) | 1977-11-22 |
| DK217477A (da) | 1977-11-22 |
| FR2351656B1 (fr) | 1978-12-15 |
| AU2525077A (en) | 1978-11-23 |
| NL7705337A (nl) | 1977-11-23 |
| ZA772986B (en) | 1978-04-26 |
| AU507900B2 (en) | 1980-02-28 |
| CA1073912A (fr) | 1980-03-18 |
| FR2351656A1 (fr) | 1977-12-16 |
| CH625225A5 (fr) | 1981-09-15 |
| JPS52142074A (en) | 1977-11-26 |
| US4128650A (en) | 1978-12-05 |
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