DE2515548A1 - Quaternaere ammoniumsalze von n-dialkylaminoalkyl-n-(2-indanyl)-anilinen und verfahren zu ihrer herstellung - Google Patents
Quaternaere ammoniumsalze von n-dialkylaminoalkyl-n-(2-indanyl)-anilinen und verfahren zu ihrer herstellungInfo
- Publication number
- DE2515548A1 DE2515548A1 DE19752515548 DE2515548A DE2515548A1 DE 2515548 A1 DE2515548 A1 DE 2515548A1 DE 19752515548 DE19752515548 DE 19752515548 DE 2515548 A DE2515548 A DE 2515548A DE 2515548 A1 DE2515548 A1 DE 2515548A1
- Authority
- DE
- Germany
- Prior art keywords
- indanyl
- hydrogen
- formula
- anilino
- compounds
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- -1 2-INDANYL Chemical class 0.000 title claims description 61
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000003863 ammonium salts Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 34
- 150000003512 tertiary amines Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- WGYKZJWCGVVSQN-UHFFFAOYSA-O propan-1-aminium Chemical compound CCC[NH3+] WGYKZJWCGVVSQN-UHFFFAOYSA-O 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims 1
- 150000001649 bromium compounds Chemical group 0.000 claims 1
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000003839 salts Chemical group 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 206010003119 arrhythmia Diseases 0.000 description 16
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 241000282472 Canis lupus familiaris Species 0.000 description 11
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000006793 arrhythmia Effects 0.000 description 8
- 230000033764 rhythmic process Effects 0.000 description 8
- GQCWHYJQXLHKDD-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-1-yl)aniline Chemical compound NC1=CC=CC=C1C1C2=CC=CC=C2CC1 GQCWHYJQXLHKDD-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 230000002045 lasting effect Effects 0.000 description 3
- 208000010125 myocardial infarction Diseases 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 3
- GIAPQOZCVIEHNY-UHFFFAOYSA-N propylazanium;iodide Chemical compound [I-].CCC[NH3+] GIAPQOZCVIEHNY-UHFFFAOYSA-N 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 229910001923 silver oxide Inorganic materials 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- VTDIWMPYBAVEDY-UHFFFAOYSA-N 1-propylpiperidine Chemical compound CCCN1CCCCC1 VTDIWMPYBAVEDY-UHFFFAOYSA-N 0.000 description 2
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical class C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- SVBXPEXMMWJPIE-UHFFFAOYSA-N acetic acid;propan-1-amine Chemical compound CCC[NH3+].CC([O-])=O SVBXPEXMMWJPIE-UHFFFAOYSA-N 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- CXZFDQPDJLQSLE-UHFFFAOYSA-N benzenesulfonate;ethylazanium Chemical compound CC[NH3+].[O-]S(=O)(=O)C1=CC=CC=C1 CXZFDQPDJLQSLE-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- MVYQJCPZZBFMLF-UHFFFAOYSA-N hydron;propan-1-amine;bromide Chemical compound [Br-].CCC[NH3+] MVYQJCPZZBFMLF-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229960004194 lidocaine Drugs 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 229960005015 local anesthetics Drugs 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- MHVHCDLCLNXADJ-UHFFFAOYSA-N n-phenyl-2,3-dihydro-1h-inden-2-amine Chemical class C1C2=CC=CC=C2CC1NC1=CC=CC=C1 MHVHCDLCLNXADJ-UHFFFAOYSA-N 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 239000002831 pharmacologic agent Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- WNEYXFDRCSFJCU-UHFFFAOYSA-N propan-1-amine;hydrate Chemical compound [OH-].CCC[NH3+] WNEYXFDRCSFJCU-UHFFFAOYSA-N 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical group C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003756 stirring Methods 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CTNPHHZPAJYPFO-PDXBGNJTSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-3-[(2r,4s,5r,6r)-5-[(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2h-furan Chemical compound C1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C=O)CC[C@@H](C[C@@]5(O)CC[C@H]4[C@@]3(O)CC2)O[C@H]2C[C@@H]([C@@H]([C@@H](C)O2)O[C@@H]2[C@H]([C@H](O)[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@H](CO)O2)O)OC)=CC(=O)OC1 CTNPHHZPAJYPFO-PDXBGNJTSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- CFIDFVNAHVRFGT-UHFFFAOYSA-N 2,3-dihydro-1h-inden-2-yl methanesulfonate Chemical compound C1=CC=C2CC(OS(=O)(=O)C)CC2=C1 CFIDFVNAHVRFGT-UHFFFAOYSA-N 0.000 description 1
- RFFWCKSTBQUTEH-UHFFFAOYSA-N 2,3-dihydro-1h-inden-2-ylmethanesulfonic acid Chemical compound C1=CC=C2CC(CS(=O)(=O)O)CC2=C1 RFFWCKSTBQUTEH-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NMILGIZTAZXMTM-UHFFFAOYSA-N 4-propylmorpholine Chemical compound CCCN1CCOCC1 NMILGIZTAZXMTM-UHFFFAOYSA-N 0.000 description 1
- WWRXMKQRGARTAB-UHFFFAOYSA-N 6-iodohex-2-ene Chemical compound CC=CCCCI WWRXMKQRGARTAB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZTHQBROSBNNGPU-UHFFFAOYSA-N Butyl hydrogen sulfate Chemical compound CCCCOS(O)(=O)=O ZTHQBROSBNNGPU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- FHIREUBIEIPPMC-UHFFFAOYSA-N K-Strophanthin-beta Natural products O1C(C)C(OC2C(C(O)C(O)C(CO)O2)O)C(OC)CC1OC(CC1(O)CCC2C3(O)CC4)CCC1(C=O)C2CCC3(C)C4C1=CC(=O)OC1 FHIREUBIEIPPMC-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- WHOLMYAZADNWQS-UHFFFAOYSA-N N-(3-chloropropyl)-N-phenyl-2,3-dihydro-1H-inden-2-amine Chemical compound ClCCCN(C1=CC=CC=C1)C1CC2=CC=CC=C2C1 WHOLMYAZADNWQS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010042434 Sudden death Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical group N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- NZLBHDRPUJLHCE-UHFFFAOYSA-N aprindine Chemical compound C1C2=CC=CC=C2CC1N(CCCN(CC)CC)C1=CC=CC=C1 NZLBHDRPUJLHCE-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- AVPRDNCYNYWMNB-UHFFFAOYSA-N ethanamine;hydrate Chemical compound [OH-].CC[NH3+] AVPRDNCYNYWMNB-UHFFFAOYSA-N 0.000 description 1
- QRMKTNANRJCRCY-UHFFFAOYSA-N ethylammonium acetate Chemical compound CC[NH3+].CC([O-])=O QRMKTNANRJCRCY-UHFFFAOYSA-N 0.000 description 1
- XFYICZOIWSBQSK-UHFFFAOYSA-N ethylazanium;iodide Chemical compound [I-].CC[NH3+] XFYICZOIWSBQSK-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- LYCYHYFONCRQGV-UHFFFAOYSA-N methanesulfonic acid;propan-1-amine Chemical compound CCC[NH3+].CS([O-])(=O)=O LYCYHYFONCRQGV-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- JWAJUTZQGZBKFS-UHFFFAOYSA-N n,n-diethylprop-2-en-1-amine Chemical compound CCN(CC)CC=C JWAJUTZQGZBKFS-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 1
- 229960000244 procainamide Drugs 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US460643A US3917679A (en) | 1974-04-12 | 1974-04-12 | Quaternary ammonium salts of N-dialkylaminoalkyl-N-(2-indanyl)anilines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2515548A1 true DE2515548A1 (de) | 1975-10-23 |
Family
ID=23829512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752515548 Withdrawn DE2515548A1 (de) | 1974-04-12 | 1975-04-09 | Quaternaere ammoniumsalze von n-dialkylaminoalkyl-n-(2-indanyl)-anilinen und verfahren zu ihrer herstellung |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3917679A (en, 2012) |
| JP (1) | JPS50135211A (en, 2012) |
| AR (1) | AR208307A1 (en, 2012) |
| AT (1) | AT342037B (en, 2012) |
| BE (1) | BE827764A (en, 2012) |
| CA (1) | CA1026757A (en, 2012) |
| CH (1) | CH609330A5 (en, 2012) |
| CS (1) | CS199265B2 (en, 2012) |
| DD (1) | DD118612A5 (en, 2012) |
| DE (1) | DE2515548A1 (en, 2012) |
| DK (1) | DK156975A (en, 2012) |
| ES (1) | ES436555A1 (en, 2012) |
| FR (1) | FR2267092B1 (en, 2012) |
| GB (1) | GB1497149A (en, 2012) |
| HU (1) | HU174568B (en, 2012) |
| IE (1) | IE40971B1 (en, 2012) |
| IL (1) | IL47060A (en, 2012) |
| NL (1) | NL7504392A (en, 2012) |
| PL (1) | PL98607B1 (en, 2012) |
| RO (1) | RO75281A (en, 2012) |
| SE (1) | SE7504099L (en, 2012) |
| SU (1) | SU575022A3 (en, 2012) |
| YU (1) | YU90375A (en, 2012) |
| ZA (1) | ZA752333B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5259995A (en) * | 1975-11-12 | 1977-05-17 | Nippon Keibi Hosho Kk | Chemical fire extinguishing method |
| JPS5259996A (en) * | 1975-11-12 | 1977-05-17 | Nippon Keibi Hosho Kk | Chemical fire extinguishing method |
| US4321386A (en) * | 1981-01-28 | 1982-03-23 | Mead Johnson & Company | Quaternary piperidinium halides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1768500A1 (de) * | 1968-05-18 | 1972-01-05 | Degussa | Verfahren zur Herstellung von Alkoxygruppen enthaltenden Aminoketonen II |
| FR127F (en, 2012) * | 1964-03-27 | |||
| US3468951A (en) * | 1965-06-14 | 1969-09-23 | American Hospital Supply Corp | Bis-(alkoxyaryl)alkyl-n-alkenyl-and-alkynyl-amines |
| SE354866B (en, 2012) * | 1968-10-09 | 1973-03-26 | Leo Ab | |
| US3875215A (en) * | 1971-07-19 | 1975-04-01 | Dow Chemical Co | Substituted phenoxyalkyl quaternary ammonium compounds |
-
1974
- 1974-04-12 US US460643A patent/US3917679A/en not_active Expired - Lifetime
-
1975
- 1975-01-01 AR AR258299A patent/AR208307A1/es active
- 1975-04-01 JP JP50040204A patent/JPS50135211A/ja active Pending
- 1975-04-09 IL IL47060A patent/IL47060A/en unknown
- 1975-04-09 SE SE7504099A patent/SE7504099L/xx unknown
- 1975-04-09 DE DE19752515548 patent/DE2515548A1/de not_active Withdrawn
- 1975-04-09 FR FR7511072A patent/FR2267092B1/fr not_active Expired
- 1975-04-09 IE IE802/75A patent/IE40971B1/xx unknown
- 1975-04-09 YU YU00903/76A patent/YU90375A/xx unknown
- 1975-04-09 CA CA224,219A patent/CA1026757A/en not_active Expired
- 1975-04-09 SU SU7502121143A patent/SU575022A3/ru active
- 1975-04-10 GB GB14664/75A patent/GB1497149A/en not_active Expired
- 1975-04-10 BE BE1006586A patent/BE827764A/xx unknown
- 1975-04-10 PL PL1975179520A patent/PL98607B1/pl unknown
- 1975-04-11 NL NL7504392A patent/NL7504392A/xx not_active Application Discontinuation
- 1975-04-11 DK DK156975A patent/DK156975A/da unknown
- 1975-04-11 DD DD185391A patent/DD118612A5/xx unknown
- 1975-04-11 CS CS752529A patent/CS199265B2/cs unknown
- 1975-04-11 CH CH466375A patent/CH609330A5/xx not_active IP Right Cessation
- 1975-04-11 AT AT278475A patent/AT342037B/de not_active IP Right Cessation
- 1975-04-11 ES ES436555A patent/ES436555A1/es not_active Expired
- 1975-04-11 ZA ZA752333A patent/ZA752333B/xx unknown
- 1975-04-11 HU HUEI000612 patent/HU174568B/hu unknown
- 1975-04-12 RO RO7581973A patent/RO75281A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2267092B1 (en, 2012) | 1978-08-04 |
| JPS50135211A (en, 2012) | 1975-10-27 |
| US3917679A (en) | 1975-11-04 |
| HU174568B (hu) | 1980-02-28 |
| ES436555A1 (es) | 1977-04-01 |
| CH609330A5 (en, 2012) | 1979-02-28 |
| IE40971B1 (en) | 1979-09-26 |
| AU7999675A (en) | 1976-10-14 |
| BE827764A (fr) | 1975-10-10 |
| SE7504099L (sv) | 1975-10-13 |
| DD118612A5 (en, 2012) | 1976-03-12 |
| NL7504392A (en, 2012) | 1975-10-14 |
| IL47060A (en) | 1977-12-30 |
| CS199265B2 (en) | 1980-07-31 |
| FR2267092A1 (en, 2012) | 1975-11-07 |
| ZA752333B (en) | 1976-11-24 |
| GB1497149A (en) | 1978-01-05 |
| AR208307A1 (es) | 1976-12-20 |
| RO75281A (ro) | 1980-11-30 |
| IE40971L (en) | 1975-10-12 |
| AT342037B (de) | 1978-03-10 |
| ATA278475A (de) | 1977-07-15 |
| YU90375A (en) | 1982-02-28 |
| CA1026757A (en) | 1978-02-21 |
| DK156975A (da) | 1975-10-13 |
| IL47060A0 (en) | 1975-06-25 |
| SU575022A3 (ru) | 1977-09-30 |
| PL98607B1 (pl) | 1978-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |