NO126271B - - Google Patents
Download PDFInfo
- Publication number
- NO126271B NO126271B NO00921/69A NO92169A NO126271B NO 126271 B NO126271 B NO 126271B NO 00921/69 A NO00921/69 A NO 00921/69A NO 92169 A NO92169 A NO 92169A NO 126271 B NO126271 B NO 126271B
- Authority
- NO
- Norway
- Prior art keywords
- dihydro
- isoquinoline
- symbols
- carbon atoms
- group containing
- Prior art date
Links
- -1 4-methyl-1-piperazinyl group Chemical group 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 239000000155 melt Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 8
- 241000700198 Cavia Species 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- RPMSUIMQCCQJDX-UHFFFAOYSA-N 1-methylsulfanyl-3,4-dihydroisoquinoline Chemical compound C1=CC=C2C(SC)=NCCC2=C1 RPMSUIMQCCQJDX-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 206010011224 Cough Diseases 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- GHYFLDWHIVKQLS-UHFFFAOYSA-N 4-(2-isothiocyanatoethyl)-1,2-dimethoxybenzene Chemical compound COC1=CC=C(CCN=C=S)C=C1OC GHYFLDWHIVKQLS-UHFFFAOYSA-N 0.000 description 3
- RUJANMWNNIAIFJ-UHFFFAOYSA-N 5-(2-isothiocyanatoethyl)-1,3-benzodioxole Chemical compound S=C=NCCC1=CC=C2OCOC2=C1 RUJANMWNNIAIFJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 229940071870 hydroiodic acid Drugs 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JNFLSJUGIONDMJ-UHFFFAOYSA-N 2-n,2-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)C(C)CN JNFLSJUGIONDMJ-UHFFFAOYSA-N 0.000 description 2
- RGUABPVONIGVAT-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propan-1-amine Chemical compound CN1CCN(CCCN)CC1 RGUABPVONIGVAT-UHFFFAOYSA-N 0.000 description 2
- LCSXOYGFJQKCFI-UHFFFAOYSA-N 6,7-dimethoxy-1-methylsulfanyl-3,4-dihydroisoquinoline Chemical compound C1CN=C(SC)C2=C1C=C(OC)C(OC)=C2 LCSXOYGFJQKCFI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000000954 anitussive effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 206010061592 cardiac fibrillation Diseases 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002600 fibrillogenic effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- ZGZHNQPTNCGKHS-UHFFFAOYSA-N 1-n,1-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)CC(C)N ZGZHNQPTNCGKHS-UHFFFAOYSA-N 0.000 description 1
- XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 1
- MUBURCRSQQCPFF-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)ethanamine;hypochlorous acid Chemical compound ClO.NCCC1=CC=C2OCOC2=C1 MUBURCRSQQCPFF-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- KFCJKQZKHMRYQF-UHFFFAOYSA-N 3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NCCC2=C1 KFCJKQZKHMRYQF-UHFFFAOYSA-N 0.000 description 1
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 1
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 1
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 1
- 208000031872 Body Remains Diseases 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 244000166550 Strophanthus gratus Species 0.000 description 1
- 244000105017 Vicia sativa Species 0.000 description 1
- 229940039750 aconitine Drugs 0.000 description 1
- STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001217 buttock Anatomy 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 230000007681 cardiovascular toxicity Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000005452 ethyl sulfates Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000002485 inorganic esters Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RRIRDPSOCUCGBV-UHFFFAOYSA-N methylenedioxyphenethylamine Chemical compound NCCC1=CC=C2OCOC2=C1 RRIRDPSOCUCGBV-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WLDFBDNWPZFNJD-UHFFFAOYSA-N n-(3,4-dihydroisoquinolin-1-yl)-n',n'-diethylethane-1,2-diamine Chemical compound C1=CC=C2C(NCCN(CC)CC)=NCCC2=C1 WLDFBDNWPZFNJD-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 229960003343 ouabain Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBADVBNRRHVIAO-UHFFFAOYSA-N phenylsulfanol Chemical class OSC1=CC=CC=C1 NBADVBNRRHVIAO-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000036279 refractory period Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/22—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C331/24—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/52—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR142607 | 1968-03-06 | ||
| FR6900907A FR2028672A6 (pl) | 1968-03-06 | 1969-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126271B true NO126271B (pl) | 1973-01-15 |
Family
ID=26181857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00921/69A NO126271B (pl) | 1968-03-06 | 1969-03-05 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3644366A (pl) |
| AT (3) | AT289120B (pl) |
| BE (1) | BE729413A (pl) |
| CH (1) | CH513862A (pl) |
| DE (1) | DE1911464C3 (pl) |
| DK (1) | DK131373B (pl) |
| ES (1) | ES364451A1 (pl) |
| FI (1) | FI48588C (pl) |
| FR (1) | FR2028672A6 (pl) |
| GB (1) | GB1264485A (pl) |
| IE (1) | IE32656B1 (pl) |
| IL (1) | IL31735A (pl) |
| NL (1) | NL146049B (pl) |
| NO (1) | NO126271B (pl) |
| SE (1) | SE352890B (pl) |
| YU (1) | YU33785B (pl) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1279533B (de) * | 1965-07-06 | 1968-10-03 | Henkel & Cie Gmbh | Ausschuettverschluss fuer Faltschachteln |
| SE347969B (pl) * | 1969-01-25 | 1972-08-21 | Tanabe Seiyaku Co | |
| FR2081572B1 (pl) * | 1970-03-12 | 1973-04-06 | Rhone Poulenc Sa | |
| FR2119989B1 (pl) * | 1970-12-29 | 1975-10-10 | Fujisawa Pharmaceutical Co | |
| GB1379111A (en) * | 1972-04-13 | 1975-01-02 | Aspro Nicholas Ltd | Preparation of fused-ring pyridine and pyrazine derivatives |
| DE2438965A1 (de) * | 1974-08-14 | 1976-02-26 | Hoechst Ag | Basisch substituierte 3,4-dihydro2h-isochinolin-1-thione und verfahren zu ihrer herstellung |
| IT1054655B (it) * | 1975-08-27 | 1981-11-30 | Lepetit Spa | Derivati condensati del l isochinolina |
| ES8100016A1 (es) * | 1978-07-18 | 1980-04-01 | Hoechst Ag | Procedimiento para la preparacion de nuevos derivados de 1-(4-aminopiperidino)-3,4-dihidroisoquinoleina. |
| DE3518693A1 (de) * | 1985-05-24 | 1986-11-27 | Henkel KGaA, 4000 Düsseldorf | Faltschachtel mit als dosierbehaelter ausgebildetem verschluss |
| US5177075A (en) * | 1988-08-19 | 1993-01-05 | Warner-Lambert Company | Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process |
| EP0355750B1 (en) * | 1988-08-19 | 1995-01-25 | Warner-Lambert Company | Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process |
| GB8908229D0 (en) * | 1989-04-12 | 1989-05-24 | Smithkline Beckman Intercredit | Compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2700040A (en) * | 1951-05-21 | 1955-01-18 | Smith Kline French Lab | Aminoalkylaminoisoquinolines |
| GB973911A (en) * | 1962-06-04 | 1964-11-04 | Ici Ltd | Dihydroisoquinoline derivatives |
-
1969
- 1969-01-20 FR FR6900907A patent/FR2028672A6/fr not_active Expired
- 1969-02-26 NL NL696902996A patent/NL146049B/xx unknown
- 1969-02-27 FI FI690615A patent/FI48588C/fi active
- 1969-03-04 IL IL31735A patent/IL31735A/en unknown
- 1969-03-05 SE SE03041/69A patent/SE352890B/xx unknown
- 1969-03-05 BE BE729413D patent/BE729413A/xx unknown
- 1969-03-05 US US804672A patent/US3644366A/en not_active Expired - Lifetime
- 1969-03-05 CH CH334669A patent/CH513862A/fr not_active IP Right Cessation
- 1969-03-05 GB GB1264485D patent/GB1264485A/en not_active Expired
- 1969-03-05 IE IE286/69A patent/IE32656B1/xx unknown
- 1969-03-05 NO NO00921/69A patent/NO126271B/no unknown
- 1969-03-05 DK DK121869AA patent/DK131373B/da unknown
- 1969-03-06 YU YU550/69A patent/YU33785B/xx unknown
- 1969-03-06 ES ES364451A patent/ES364451A1/es not_active Expired
- 1969-03-06 AT AT386570A patent/AT289120B/de not_active IP Right Cessation
- 1969-03-06 DE DE1911464A patent/DE1911464C3/de not_active Expired
- 1969-03-06 AT AT386670A patent/AT289121B/de not_active IP Right Cessation
- 1969-03-06 AT AT222469A patent/AT289118B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE729413A (pl) | 1969-09-05 |
| IL31735A (en) | 1973-01-30 |
| ES364451A1 (es) | 1971-02-01 |
| DK131373B (da) | 1975-07-07 |
| DE1911464B2 (de) | 1975-02-27 |
| YU55069A (en) | 1977-10-31 |
| GB1264485A (pl) | 1972-02-23 |
| SE352890B (pl) | 1973-01-15 |
| FI48588C (fi) | 1974-11-11 |
| IE32656L (en) | 1969-09-06 |
| NL6902996A (pl) | 1969-09-09 |
| DK131373C (pl) | 1975-12-01 |
| DE1911464C3 (de) | 1975-10-09 |
| IE32656B1 (en) | 1973-10-17 |
| NL146049B (nl) | 1975-06-16 |
| US3644366A (en) | 1972-02-22 |
| YU33785B (en) | 1978-05-15 |
| AT289120B (de) | 1971-04-13 |
| AT289121B (de) | 1971-04-13 |
| CH513862A (fr) | 1971-10-15 |
| FI48588B (pl) | 1974-07-31 |
| DE1911464A1 (de) | 1971-06-16 |
| AT289118B (de) | 1971-04-13 |
| FR2028672A6 (pl) | 1970-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2716146B2 (ja) | 縮合インドール誘導体およびその製造方法 | |
| US3682930A (en) | 4(1-alkyl-4-piperidylidine)-4h-benzo {84,5{9 {0 cyclohepta {8 1,2{14 6{9 | |
| EP0110372B1 (de) | 1-Phenylisochinolinderivate und Verfahren zu ihrer Herstellung, diese Verbindung enthaltende pharmazeutische Präparate und deren Anwendung | |
| DE1795183B1 (de) | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate und Arzneimittel | |
| US3272707A (en) | Pharmaceutical compositions and methods for their use | |
| NO126271B (pl) | ||
| IE56836B1 (en) | Novel pharmaceutically active 1,2,3,4,4a,5,10,10a-octahydrobenzo(g)quinoline derivatives | |
| US3759924A (en) | 1-amino-3(or4)-phenyl-3,4-dehydroisoquinolines | |
| DE3023626A1 (de) | 1,9-dihydroxyoctahydrobenzo eckige klammer auf c eckige klammer zu chinoline und 1-hydroxyhexahydrobenzo eckige klammer auf c eckige klammer zu chinolin-9 (8h)- one als antiemetika | |
| Tullar et al. | Benzomorphans. Optically active and trans isomers | |
| CH637956A5 (de) | In 11-stellung substituierte 5,11-dihydro-6h-pyrido-(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. | |
| DE69232484T2 (de) | Hydroisochinolinderivate | |
| CH629782A5 (de) | Verfahren zur herstellung von 4-hydroxy-aporphinderivaten. | |
| DE3028001A1 (de) | Neue, in 5-stellung substituierte 5,10-dihydro-11h-dibenzo (b,e)(1,4) diazepin-11-one, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel | |
| CH637653A5 (de) | In 11-stellung substituierte 5,11-dihydro-6h-pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. | |
| NO140348B (no) | Analogifremgangsmaate til fremstilling av nye terapeutisk aktive 3-(amino-2-hydroksypropoksy)-isoindolin-1-on-forbindelser | |
| NZ205513A (en) | Isoquinoline-4-carboxylic acid derivatives and pharmaceutical compositions containing such | |
| DE2629887A1 (de) | Arzneimittel mit die peripheren dopamin-rezeptoren stimulierender, die nierengefaesse erweiternder, diuretischer und das parkinsonsyndrom lindernder wirkung | |
| EP0201085A2 (en) | 6-Phenyl-1,2,3,4,4a,5,6,10b-octahydrobenz(h) isoquinolines | |
| Cohen et al. | Antiplasmodial action and chemical constitution Part I. Cinchona alkaloidal derivatives and allied substances | |
| US3422110A (en) | Ergot alkaloids methylated in the 10a'-position | |
| CA2045413A1 (en) | Tricyclic antipsychotic agents | |
| US4764517A (en) | 8α-(N,N-diethylsulfamoylamino)-6-n-propyl ergoline useful as a prolactin secretion inhibitor, anti-parkinson, anti-depressant agent | |
| US3549644A (en) | 2,3,4,4a,5,6,8,9,13b,13c - decahydro-1h-dibenzo (a,h)quinolizines and process for their production | |
| US3466290A (en) | 9,10-dihydro-4h-benzo(4,5)cyclohepta(1,2-b)thiophene ethers |