IL26843A - Bis(3,4-dihydroisoquinol-1-ylium)alkane salts with pharmacological activity - Google Patents
Bis(3,4-dihydroisoquinol-1-ylium)alkane salts with pharmacological activityInfo
- Publication number
- IL26843A IL26843A IL26843A IL2684366A IL26843A IL 26843 A IL26843 A IL 26843A IL 26843 A IL26843 A IL 26843A IL 2684366 A IL2684366 A IL 2684366A IL 26843 A IL26843 A IL 26843A
- Authority
- IL
- Israel
- Prior art keywords
- bis
- salt
- compound
- octane
- dihydroisoquinol
- Prior art date
Links
- 230000000144 pharmacologic effect Effects 0.000 title description 2
- FTDGQUCYABTDSV-UHFFFAOYSA-N 1,2-didehydro-3,4-dihydroisoquinolin-2-ium Chemical class C1=CC=C2C#[N+]CCC2=C1 FTDGQUCYABTDSV-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- -1 ethylenedioxy group Chemical group 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000005649 metathesis reaction Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 70
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 49
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 44
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 23
- 238000010992 reflux Methods 0.000 description 19
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- 239000002585 base Substances 0.000 description 17
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000012362 glacial acetic acid Substances 0.000 description 14
- 206010033799 Paralysis Diseases 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- DFJYZCUIKPGCSG-UHFFFAOYSA-N decanedinitrile Chemical compound N#CCCCCCCCCC#N DFJYZCUIKPGCSG-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 9
- 239000001117 sulphuric acid Substances 0.000 description 9
- 235000011149 sulphuric acid Nutrition 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 229910021529 ammonia Inorganic materials 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
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- ICLWTJIMXVISSR-UHFFFAOYSA-N gallamine Chemical compound CCN(CC)CCOC1=CC=CC(OCCN(CC)CC)=C1OCCN(CC)CC ICLWTJIMXVISSR-UHFFFAOYSA-N 0.000 description 5
- 229960003054 gallamine Drugs 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 230000002232 neuromuscular Effects 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- AXOIZCJOOAYSMI-UHFFFAOYSA-N succinylcholine Chemical compound C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C AXOIZCJOOAYSMI-UHFFFAOYSA-N 0.000 description 5
- 230000002889 sympathetic effect Effects 0.000 description 5
- BZEQNFVPYDJAOS-UHFFFAOYSA-N 1-(3-methoxyphenyl)-2-methylpropan-2-ol Chemical compound COC1=CC=CC(CC(C)(C)O)=C1 BZEQNFVPYDJAOS-UHFFFAOYSA-N 0.000 description 4
- 241000282693 Cercopithecidae Species 0.000 description 4
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- 241000282326 Felis catus Species 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
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- 239000012458 free base Substances 0.000 description 4
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229940120904 succinylcholine chloride Drugs 0.000 description 4
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- 206010029315 Neuromuscular blockade Diseases 0.000 description 3
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
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- 230000002567 autonomic effect Effects 0.000 description 3
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- 238000002347 injection Methods 0.000 description 3
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
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- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 3
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 3
- 230000002688 persistence Effects 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- UMYZWICEDUEWIM-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-one Chemical compound COC1=CC=C(CC(C)=O)C=C1OC UMYZWICEDUEWIM-UHFFFAOYSA-N 0.000 description 2
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- CYRFLEMTQNARBO-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-2-methylpropan-1-amine Chemical compound COC1=CC=C(C(C)(C)CN)C=C1OC CYRFLEMTQNARBO-UHFFFAOYSA-N 0.000 description 1
- ASLSUMISAQDOOB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1OC ASLSUMISAQDOOB-UHFFFAOYSA-N 0.000 description 1
- QZMGMXBYJZVAJN-UHFFFAOYSA-N 3-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1 QZMGMXBYJZVAJN-UHFFFAOYSA-N 0.000 description 1
- LHWIZYOSZOQHOY-UHFFFAOYSA-N 5-(2-nitrobut-1-enyl)-1,3-benzodioxole Chemical compound CCC([N+]([O-])=O)=CC1=CC=C2OCOC2=C1 LHWIZYOSZOQHOY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- 206010048964 Carotid artery occlusion Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000003914 Cholinesterases Human genes 0.000 description 1
- 108090000322 Cholinesterases Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 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 1
- 206010050031 Muscle strain Diseases 0.000 description 1
- 208000033952 Paralysis flaccid Diseases 0.000 description 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Chemical class C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 1
- 238000006434 Ritter amidation reaction Methods 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N Sec-butyl alcohol Natural products CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 206010041415 Spastic paralysis Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 230000003504 ach effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- 229940075522 antidotes Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 208000008784 apnea Diseases 0.000 description 1
- 230000037424 autonomic function Effects 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- YXXPNGIZHZHBTQ-UHFFFAOYSA-N butan-2-ol Chemical compound CC[C](C)O YXXPNGIZHZHBTQ-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229940048961 cholinesterase Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229950000405 decamethonium Drugs 0.000 description 1
- VDBXLXRWMYNMHL-UHFFFAOYSA-N decanediamide Chemical compound NC(=O)CCCCCCCCC(N)=O VDBXLXRWMYNMHL-UHFFFAOYSA-N 0.000 description 1
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 208000028331 flaccid paralysis Diseases 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 229960002362 neostigmine Drugs 0.000 description 1
- LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical class [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 210000000715 neuromuscular junction Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 210000000826 nictitating membrane Anatomy 0.000 description 1
- HQYYEEBKIWTFKS-UHFFFAOYSA-N octane dihydroiodide Chemical compound I.I.CCCCCCCC HQYYEEBKIWTFKS-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001734 parasympathetic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229960001697 physostigmine Drugs 0.000 description 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical class C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036584 pressor response Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 210000003497 sciatic nerve Anatomy 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229940032712 succinylcholine Drugs 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- HLXQFVXURMXRPU-UHFFFAOYSA-L trimethyl-[10-(trimethylazaniumyl)decyl]azanium;dibromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C HLXQFVXURMXRPU-UHFFFAOYSA-L 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Classifications
-
- 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
- C07D221/20—Spiro-condensed ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/10—Quaternary compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB48507/65A GB1125619A (en) | 1965-11-15 | 1965-11-15 | Derivatives of bis-isoquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL26843A true IL26843A (en) | 1970-11-30 |
Family
ID=10448871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL26843A IL26843A (en) | 1965-11-15 | 1966-11-11 | Bis(3,4-dihydroisoquinol-1-ylium)alkane salts with pharmacological activity |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3491099A (en, 2012) |
| AT (1) | AT268284B (en, 2012) |
| BE (1) | BE689694A (en, 2012) |
| BR (1) | BR6684567D0 (en, 2012) |
| CH (1) | CH484137A (en, 2012) |
| DE (1) | DE1620739A1 (en, 2012) |
| ES (1) | ES333336A1 (en, 2012) |
| FR (1) | FR6266M (en, 2012) |
| GB (1) | GB1125619A (en, 2012) |
| IL (1) | IL26843A (en, 2012) |
| LU (1) | LU52362A1 (en, 2012) |
| MC (1) | MC624A1 (en, 2012) |
| NL (1) | NL6616080A (en, 2012) |
| SE (1) | SE325572B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3979394A (en) * | 1970-12-11 | 1976-09-07 | Agfa-Gevaert N.V. | Duplo quinoline compounds |
| US3932418A (en) * | 1971-11-10 | 1976-01-13 | Agfa-Gevaert N.V. | Electrophotographic material |
| AU506657B2 (en) * | 1975-12-10 | 1980-01-17 | Wellcome Foundation Limited, The | Isoquinoline derivatives |
| US4235906A (en) * | 1978-07-21 | 1980-11-25 | Massachusetts General Hospital | Bis-isoquinolinium compounds, compositions and methods of use |
| CA1125287A (en) * | 1978-07-21 | 1982-06-08 | John J. Savarese | Bis isoquinolinium compositions and methods of use |
| EP0098241B1 (de) * | 1982-06-16 | 1985-10-02 | Ciba-Geigy Ag | Hydrochinonäther und ein Verfahren zu deren Herstellung |
| FR3046169B1 (fr) | 2015-12-23 | 2022-05-20 | Oreal | Utilisation de sels de dihydroisoquinolinium pour le traitement des matieres keratiniques, compositions et procedes de mise en oeuvre |
| FR3046170B1 (fr) | 2015-12-23 | 2020-02-07 | L'oreal | Utilisation de derives de dihydroisoquinolinium double pour le traitement des matieres keratiniques, compositions et procedes de mise en oeuvre |
| FR3046168B1 (fr) | 2015-12-23 | 2019-11-01 | L'oreal | Utilisation de sels de dihydroisoquinolinium substitue pour le traitement des matieres keratiniques, compositions et procedes de mise en oeuvre |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2662083A (en) * | 1950-10-24 | 1953-12-08 | Allen & Hanburys Ltd | Heterocyclic polymethylene-bisquaternary ammonium salts and process for preparing same |
| US2659728A (en) * | 1951-07-05 | 1953-11-17 | Smith Kline & Freneh Lab | Bis-hydroxytetrahydroiso-quinolyl-alkanes |
| US2744901A (en) * | 1951-07-30 | 1956-05-08 | Smith Kline French Lab | Bis-tetrahydro-1-isoquinolyl quaternary ammonium salts |
| US3138600A (en) * | 1959-05-25 | 1964-06-23 | Miles Lab | Bis (tetrahydroisoquinolyl) alkanes |
-
1965
- 1965-11-15 GB GB48507/65A patent/GB1125619A/en not_active Expired
-
1966
- 1966-11-11 IL IL26843A patent/IL26843A/en unknown
- 1966-11-14 BE BE689694D patent/BE689694A/xx unknown
- 1966-11-14 ES ES0333336A patent/ES333336A1/es not_active Expired
- 1966-11-14 BR BR184567/66A patent/BR6684567D0/pt unknown
- 1966-11-15 NL NL6616080A patent/NL6616080A/xx unknown
- 1966-11-15 CH CH1638366A patent/CH484137A/de not_active IP Right Cessation
- 1966-11-15 AT AT1054866A patent/AT268284B/de active
- 1966-11-15 DE DE19661620739 patent/DE1620739A1/de active Pending
- 1966-11-15 MC MC656A patent/MC624A1/xx unknown
- 1966-11-15 SE SE15594/66A patent/SE325572B/xx unknown
- 1966-11-15 LU LU52362D patent/LU52362A1/xx unknown
-
1967
- 1967-02-14 FR FR94816A patent/FR6266M/fr not_active Expired
-
1969
- 1969-03-20 US US809007A patent/US3491099A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620739A1 (de) | 1970-09-24 |
| LU52362A1 (en, 2012) | 1967-05-17 |
| US3491099A (en) | 1970-01-20 |
| ES333336A1 (es) | 1967-08-01 |
| MC624A1 (fr) | 1967-07-04 |
| FR6266M (en, 2012) | 1968-08-26 |
| BE689694A (en, 2012) | 1967-05-16 |
| CH484137A (de) | 1970-01-15 |
| NL6616080A (en, 2012) | 1967-05-16 |
| BR6684567D0 (pt) | 1973-12-18 |
| AT268284B (de) | 1969-02-10 |
| GB1125619A (en) | 1968-08-28 |
| SE325572B (en, 2012) | 1970-07-06 |
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