IL26843A - Bis(3,4-dihydroisoquinol-1-ylium)alkane salts with pharmacological activity - Google Patents

Bis(3,4-dihydroisoquinol-1-ylium)alkane salts with pharmacological activity

Info

Publication number: IL26843A
Authority: IL; Israel
Prior art keywords: bis; salt; compound; octane; dihydroisoquinol
Prior art date: 1965-11-15

Application number

IL26843A

Other languages

English (en)

Original Assignee

Wellcome Found

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1965-11-15

Filing date

1966-11-11

Publication date

1970-11-30

1966-11-11 Application filed by Wellcome Found filed Critical Wellcome Found

1970-11-30 Publication of IL26843A publication Critical patent/IL26843A/en

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
229960000583 acetic acid Drugs 0.000 description 18
239000002585 base Substances 0.000 description 17
210000003205 muscle Anatomy 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
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
229960004592 isopropanol Drugs 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 7
229960004373 acetylcholine Drugs 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
238000009835 boiling Methods 0.000 description 7
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 7
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
230000009471 action Effects 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000012528 membrane Substances 0.000 description 6
230000008569 process Effects 0.000 description 6
JFJZZMVDLULRGK-URLMMPGGSA-O tubocurarine Chemical compound C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CCN3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 JFJZZMVDLULRGK-URLMMPGGSA-O 0.000 description 6
229960001844 tubocurarine Drugs 0.000 description 6
241000283973 Oryctolagus cuniculus Species 0.000 description 5
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
230000005540 biological transmission Effects 0.000 description 5
230000036772 blood pressure Effects 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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
239000007864 aqueous solution Substances 0.000 description 4
239000012458 free base Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
210000005036 nerve Anatomy 0.000 description 4
230000002182 neurohumoral effect Effects 0.000 description 4
239000000842 neuromuscular blocking agent Substances 0.000 description 4
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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000002567 autonomic effect Effects 0.000 description 3
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
239000001273 butane Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
230000002860 competitive effect Effects 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
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
239000007788 liquid Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
230000007383 nerve stimulation Effects 0.000 description 3
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
239000002244 precipitate Substances 0.000 description 3
210000002027 skeletal muscle Anatomy 0.000 description 3
229910021653 sulphate ion Inorganic materials 0.000 description 3
210000000225 synapse Anatomy 0.000 description 3
230000000980 vagolytic effect Effects 0.000 description 3
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
IKBPSPXDWSOMJJ-UHFFFAOYSA-N 1-(3-ethoxyphenyl)-2-methylpropan-2-ol Chemical compound CCOC1=CC=CC(CC(C)(C)O)=C1 IKBPSPXDWSOMJJ-UHFFFAOYSA-N 0.000 description 2
JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 2
WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
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108010053652 Butyrylcholinesterase Proteins 0.000 description 2
XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
102100032404 Cholinesterase Human genes 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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241000282414 Homo sapiens Species 0.000 description 2
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YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000002981 blocking agent Substances 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
229960001231 choline Drugs 0.000 description 2
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229960001760 dimethyl sulfoxide Drugs 0.000 description 2
229960003748 edrophonium Drugs 0.000 description 2
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230000000574 ganglionic effect Effects 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
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230000004118 muscle contraction Effects 0.000 description 2
230000036963 noncompetitive effect Effects 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
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238000011084 recovery Methods 0.000 description 2
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ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
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229910000104 sodium hydride Inorganic materials 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
230000001515 vagal effect Effects 0.000 description 2
WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
OQYNFBPKTVQOKO-UHFFFAOYSA-N 1,1-dichlorooctane Chemical compound CCCCCCCC(Cl)Cl OQYNFBPKTVQOKO-UHFFFAOYSA-N 0.000 description 1
MMLNTSKEWFKJQF-UHFFFAOYSA-N 1,2-dimethoxy-3-(2-nitroprop-1-enyl)benzene Chemical compound COC1=CC=CC(C=C(C)[N+]([O-])=O)=C1OC MMLNTSKEWFKJQF-UHFFFAOYSA-N 0.000 description 1
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
PBSGUUZLCSVFEC-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-methylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=C2OCOC2=C1 PBSGUUZLCSVFEC-UHFFFAOYSA-N 0.000 description 1
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HVYXNVQLRUJLAO-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-2-methylpropan-2-ol Chemical compound COC1=CC=C(CC(C)(C)O)C=C1OC HVYXNVQLRUJLAO-UHFFFAOYSA-N 0.000 description 1
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RMMRRRLPDBJBQL-UHFFFAOYSA-N 1-(3-methoxyphenyl)propan-2-one Chemical compound COC1=CC=CC(CC(C)=O)=C1 RMMRRRLPDBJBQL-UHFFFAOYSA-N 0.000 description 1
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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
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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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)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (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)

IL26843A 1965-11-15 1966-11-11 Bis(3,4-dihydroisoquinol-1-ylium)alkane salts with pharmacological activity IL26843A (en)

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 (th)
AT (1)	AT268284B (th)
BE (1)	BE689694A (th)
BR (1)	BR6684567D0 (th)
CH (1)	CH484137A (th)
DE (1)	DE1620739A1 (th)
ES (1)	ES333336A1 (th)
FR (1)	FR6266M (th)
GB (1)	GB1125619A (th)
IL (1)	IL26843A (th)
LU (1)	LU52362A1 (th)
MC (1)	MC624A1 (th)
NL (1)	NL6616080A (th)
SE (1)	SE325572B (th)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
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
CA1125287A (en) *	1978-07-21	1982-06-08	John J. Savarese	Bis isoquinolinium compositions and methods of use
US4235906A (en) *	1978-07-21	1980-11-25	Massachusetts General Hospital	Bis-isoquinolinium compounds, compositions and methods of use
DE3360926D1 (en) *	1982-06-16	1985-11-07	Ciba Geigy Ag	Hydroquinone ethers and a process for preparing them
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
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
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

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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 ES ES0333336A patent/ES333336A1/es not_active Expired
- 1966-11-14 BR BR184567/66A patent/BR6684567D0/pt unknown
- 1966-11-14 BE BE689694D patent/BE689694A/xx unknown
- 1966-11-15 SE SE15594/66A patent/SE325572B/xx unknown
- 1966-11-15 MC MC656A patent/MC624A1/fr unknown
- 1966-11-15 DE DE19661620739 patent/DE1620739A1/de active Pending
- 1966-11-15 NL NL6616080A patent/NL6616080A/xx unknown
- 1966-11-15 LU LU52362D patent/LU52362A1/xx unknown
- 1966-11-15 CH CH1638366A patent/CH484137A/de not_active IP Right Cessation
- 1966-11-15 AT AT1054866A patent/AT268284B/de active
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
GB1125619A (en)	1968-08-28
AT268284B (de)	1969-02-10
FR6266M (th)	1968-08-26
CH484137A (de)	1970-01-15
DE1620739A1 (de)	1970-09-24
BE689694A (th)	1967-05-16
ES333336A1 (es)	1967-08-01
NL6616080A (th)	1967-05-16
US3491099A (en)	1970-01-20
BR6684567D0 (pt)	1973-12-18
SE325572B (th)	1970-07-06
MC624A1 (fr)	1967-07-04
LU52362A1 (th)	1967-05-17

Publication	Publication Date	Title
FI71120C (fi)	1986-11-24	Foerfarande foer framstaellning av anagetiskt anvaendbara 1,9-dihydroxioktahydrofenantrener
JPS6043342B2 (ja)	1985-09-27	イソキノリニウム化合物
US3912740A (en)	1975-10-14	Method for the preparation of oxygenated benzo{8 c{9 phenanthridine compounds
US3272707A (en)	1966-09-13	Pharmaceutical compositions and methods for their use
CH643736A5 (de)	1984-06-29	Pharmazeutische zubereitungen, enthaltend imidazolderivate oder deren salze.
DE2437610A1 (de)	1976-02-26	Neue 5,9-beta-disubstituierte 2-tetrahydrofurfuryl-6,7-benzomorphane, deren saeureadditionssalze, ihre verwendung als arzneimittel und verfahren zu deren herstellung
US3763183A (en)	1973-10-02	1,2,3,10,11,11a-hexahydro-5h-pyrrolo (2,1-c)(1,4)benzodiazepines
US3491099A (en)	1970-01-20	Polymethylene-bis-isoquinolinium compounds
WO1989002740A1 (en)	1989-04-06	4-aminopyridine derivatives
DE2062001A1 (de)	1971-07-15	Isochinolin Derivate
CH645371A5 (de)	1984-09-28	Isochromane, isothiochromane, 2-benzoxepine und 2-benzothiepine.
Sobotka et al.	1965	Azasteroids. V. The Direct Conversion of 1-(Carboethoxymethyl)-1, 2, 3, 4-tetrahydroisoquinolines and Cyclic Ketones into Benzo [a] cycloalkano [f] quinolizinones. An Example of Enamine Acylation by an Ester Function1, 2
DE1445845A1 (de)	1969-02-06	Neue Benzomorphane und Verfahren zu ihrer Herstellung
DE69004702T2 (de)	1994-06-09	Aminoalkoxyphenyl-Derivate, Verfahren zu ihrer Herstellung und diese Derivate enhaltende Zusammensetzungen.
US3256289A (en)	1966-06-14	Carbocyclic substituted piperidyl dioxanes
CH618162A5 (th)	1980-07-15
DD143254A5 (de)	1980-08-13	Verfahren zur herstellung von tetrahydroisochinolin-derivaten
US3860600A (en)	1975-01-14	Octahydropyrrido{8 2,1-c{9 {8 1,4{9 benzodiazepines
US3732212A (en)	1973-05-08	1,2,3,10,11,11a-hexahydro-5h-pyrrolo(2,1-c)(1,4)benzodiazepine-5,11-diones
DE3854991T2 (de)	1996-07-18	Cyclische Amine und pharmakologische Verbindungen
Cannon et al.	1984	Conformationally restricted congeners of dopamine derived from octahydrobenzo [g] quinoline and octahydrobenzo [f] quinoline
DE2722383C2 (th)	1990-06-07
US3497517A (en)	1970-02-24	1,3,4,9b-tetrahydro-2h-indeno(1,2-c) pyridines
WO1990001025A1 (en)	1990-02-08	Enamine quaternary compounds, methods of making and their use as muscle relaxants
US3796715A (en)	1974-03-12	8-alkoxy-3,4-dihydroisoquinolines