CA1042921A - Diarylbutanolamines - Google Patents
DiarylbutanolaminesInfo
- Publication number
- CA1042921A CA1042921A CA249,358A CA249358A CA1042921A CA 1042921 A CA1042921 A CA 1042921A CA 249358 A CA249358 A CA 249358A CA 1042921 A CA1042921 A CA 1042921A
- Authority
- CA
- Canada
- Prior art keywords
- diphenyl
- hydroxybutylamine
- epoxy
- prepared
- preparing
- 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.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 150000001412 amines Chemical class 0.000 claims description 23
- RJFZHRLJWYCZDB-UHFFFAOYSA-N 2-(2,2-diphenylethyl)oxirane Chemical compound C1OC1CC(C=1C=CC=CC=1)C1=CC=CC=C1 RJFZHRLJWYCZDB-UHFFFAOYSA-N 0.000 claims description 20
- -1 N-methyl-4,4-diphenyl-2-hydroxybutylamine Chemical compound 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 5
- OBCILZMINJAKRE-UHFFFAOYSA-N 1-(diethylamino)-4,4-diphenylbutan-2-ol Chemical compound C=1C=CC=CC=1C(CC(O)CN(CC)CC)C1=CC=CC=C1 OBCILZMINJAKRE-UHFFFAOYSA-N 0.000 claims description 4
- LGXAFSFGHKCXJU-UHFFFAOYSA-N 1-(dipropylamino)-4,4-diphenylbutan-2-ol Chemical compound C=1C=CC=CC=1C(CC(O)CN(CCC)CCC)C1=CC=CC=C1 LGXAFSFGHKCXJU-UHFFFAOYSA-N 0.000 claims description 4
- BCAKLLIEFFXSIX-UHFFFAOYSA-N 1-[di(propan-2-yl)amino]-4,4-diphenylbutan-2-ol Chemical compound C=1C=CC=CC=1C(CC(O)CN(C(C)C)C(C)C)C1=CC=CC=C1 BCAKLLIEFFXSIX-UHFFFAOYSA-N 0.000 claims description 4
- OCOJSLDVZSEYJF-UHFFFAOYSA-N 2-[2,2-bis(4-fluorophenyl)ethyl]oxirane Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CC1OC1 OCOJSLDVZSEYJF-UHFFFAOYSA-N 0.000 claims description 4
- DAIZVBCVNQSHLI-UHFFFAOYSA-N 4,4-diphenyl-1-(propan-2-ylamino)butan-2-ol Chemical compound C=1C=CC=CC=1C(CC(O)CNC(C)C)C1=CC=CC=C1 DAIZVBCVNQSHLI-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
- DYEYZGYLFUSJMS-UHFFFAOYSA-N 1-(dimethylamino)-4,4-diphenylbutan-2-ol Chemical compound C=1C=CC=CC=1C(CC(O)CN(C)C)C1=CC=CC=C1 DYEYZGYLFUSJMS-UHFFFAOYSA-N 0.000 claims description 3
- HVXVKKFEWUAQTQ-UHFFFAOYSA-N 1-amino-4,4-diphenylbutan-2-ol Chemical compound C=1C=CC=CC=1C(CC(O)CN)C1=CC=CC=C1 HVXVKKFEWUAQTQ-UHFFFAOYSA-N 0.000 claims description 3
- 229940043279 diisopropylamine Drugs 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Chemical group 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- LXYQMYUTGHOZPE-UHFFFAOYSA-N 1-(ethylamino)-4,4-diphenylbutan-2-ol Chemical compound C=1C=CC=CC=1C(CC(O)CNCC)C1=CC=CC=C1 LXYQMYUTGHOZPE-UHFFFAOYSA-N 0.000 claims 2
- GIAJZJXEBWJHAO-UHFFFAOYSA-N 4,4-diphenyl-1-(propylamino)butan-2-ol Chemical compound C=1C=CC=CC=1C(CC(O)CNCCC)C1=CC=CC=C1 GIAJZJXEBWJHAO-UHFFFAOYSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- YBVSJQSIFMQYEE-UHFFFAOYSA-N 1-(tert-butylamino)-4,4-diphenylbutan-2-ol Chemical compound C=1C=CC=CC=1C(CC(O)CNC(C)(C)C)C1=CC=CC=C1 YBVSJQSIFMQYEE-UHFFFAOYSA-N 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 19
- 238000002360 preparation method Methods 0.000 abstract description 11
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 8
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 5
- 239000012458 free base Substances 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 206010003119 arrhythmia Diseases 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 230000006793 arrhythmia Effects 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003416 antiarrhythmic agent Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 150000002924 oxiranes Chemical class 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 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 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- YKYKDSHUKOVMBU-UHFFFAOYSA-N (2-hydroxy-4,4-diphenylbutyl)-propan-2-ylazanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CC(O)CNC(C)C)C1=CC=CC=C1 YKYKDSHUKOVMBU-UHFFFAOYSA-N 0.000 description 3
- YAYMPFAVJAGSHD-UHFFFAOYSA-N 1-phenylbut-3-enylbenzene Chemical compound C=1C=CC=CC=1C(CC=C)C1=CC=CC=C1 YAYMPFAVJAGSHD-UHFFFAOYSA-N 0.000 description 3
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000008121 dextrose Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- GZRYBYIBLHMWCD-UHFFFAOYSA-N dimethyl(methylidene)-$l^{4}-sulfane Chemical compound CS(C)=C GZRYBYIBLHMWCD-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000009472 formulation Methods 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
- 238000001990 intravenous administration Methods 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- WKKJYBXSVTWCRT-UHFFFAOYSA-N (2-hydroxy-4,4-diphenylbutyl)-dipropylazanium;oxalate Chemical compound [O-]C(=O)C([O-])=O.C=1C=CC=CC=1C(CC(O)C[NH+](CCC)CCC)C1=CC=CC=C1.C=1C=CC=CC=1C(CC(O)C[NH+](CCC)CCC)C1=CC=CC=C1 WKKJYBXSVTWCRT-UHFFFAOYSA-N 0.000 description 2
- KODLUXHSIZOKTG-UHFFFAOYSA-N 1-aminobutan-2-ol Chemical class CCC(O)CN KODLUXHSIZOKTG-UHFFFAOYSA-N 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- FZAARAMCGHWPPC-UHFFFAOYSA-N 4,4-diphenyl-1-piperidin-1-ium-1-ylbutan-2-ol;chloride Chemical compound Cl.C1CCCCN1CC(O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 FZAARAMCGHWPPC-UHFFFAOYSA-N 0.000 description 2
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HMNIFULFGWINMM-UHFFFAOYSA-N [4,4-bis(4-fluorophenyl)-2-hydroxybutyl]-propan-2-ylazanium;chloride Chemical compound [Cl-].C=1C=C(F)C=CC=1C(CC(O)C[NH2+]C(C)C)C1=CC=C(F)C=C1 HMNIFULFGWINMM-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound 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
- 230000033764 rhythmic process Effects 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- MRZWORDLQIWYKI-UHFFFAOYSA-N (2-hydroxy-4,4-diphenylbutyl)-di(propan-2-yl)azanium;oxalate Chemical compound [O-]C(=O)C([O-])=O.C=1C=CC=CC=1C(CC(O)C[NH+](C(C)C)C(C)C)C1=CC=CC=C1.C=1C=CC=CC=1C(CC(O)C[NH+](C(C)C)C(C)C)C1=CC=CC=C1 MRZWORDLQIWYKI-UHFFFAOYSA-N 0.000 description 1
- SDJIWPIJNVCEHL-UHFFFAOYSA-N (2-hydroxy-4,4-diphenylbutyl)-dimethylazanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(CC(O)C[NH+](C)C)C1=CC=CC=C1 SDJIWPIJNVCEHL-UHFFFAOYSA-N 0.000 description 1
- GNVWAYNIXJQDNB-UHFFFAOYSA-N (2-hydroxy-4,4-diphenylbutyl)-methylazanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(CC(O)C[NH2+]C)C1=CC=CC=C1 GNVWAYNIXJQDNB-UHFFFAOYSA-N 0.000 description 1
- ZTYZOQNTUMXWJL-UHFFFAOYSA-N (2-hydroxy-4,4-diphenylbutyl)-propylazanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(CC(O)C[NH2+]CCC)C1=CC=CC=C1 ZTYZOQNTUMXWJL-UHFFFAOYSA-N 0.000 description 1
- DLXIBGQHODXBSB-UHFFFAOYSA-N (2-hydroxy-4,4-diphenylbutyl)-trimethylazanium Chemical compound C=1C=CC=CC=1C(CC(O)C[N+](C)(C)C)C1=CC=CC=C1 DLXIBGQHODXBSB-UHFFFAOYSA-N 0.000 description 1
- KVUGTPLCIQGNNN-UHFFFAOYSA-N (2-hydroxy-4,4-diphenylbutyl)azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(CC(O)C[NH3+])C1=CC=CC=C1 KVUGTPLCIQGNNN-UHFFFAOYSA-N 0.000 description 1
- CQWHVQROMSVLQI-UHFFFAOYSA-N (3-methyl-1-phenylbut-3-enyl)benzene Chemical compound C=1C=CC=CC=1C(CC(=C)C)C1=CC=CC=C1 CQWHVQROMSVLQI-UHFFFAOYSA-N 0.000 description 1
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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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/583,819 US4001328A (en) | 1975-06-04 | 1975-06-04 | Diarylbutanolamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042921A true CA1042921A (en) | 1978-11-21 |
Family
ID=24334692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA249,358A Expired CA1042921A (en) | 1975-06-04 | 1976-04-01 | Diarylbutanolamines |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4001328A (en, 2012) |
| JP (1) | JPS51143651A (en, 2012) |
| AR (1) | AR211122A1 (en, 2012) |
| AT (1) | AT342034B (en, 2012) |
| AU (1) | AU1261376A (en, 2012) |
| BE (1) | BE842484A (en, 2012) |
| CA (1) | CA1042921A (en, 2012) |
| CS (1) | CS191308B2 (en, 2012) |
| DD (1) | DD125200A5 (en, 2012) |
| DE (1) | DE2624783A1 (en, 2012) |
| DK (1) | DK138265B (en, 2012) |
| ES (1) | ES448594A1 (en, 2012) |
| FR (1) | FR2313022A1 (en, 2012) |
| GB (1) | GB1547195A (en, 2012) |
| GR (1) | GR58235B (en, 2012) |
| IL (1) | IL49319A (en, 2012) |
| NL (1) | NL7606043A (en, 2012) |
| PH (1) | PH12074A (en, 2012) |
| PL (1) | PL100181B1 (en, 2012) |
| PT (1) | PT65030B (en, 2012) |
| RO (1) | RO70076A (en, 2012) |
| SE (1) | SE7604781L (en, 2012) |
| ZA (1) | ZA761906B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197313A (en) * | 1979-03-12 | 1980-04-08 | Eli Lilly And Company | Antiarrhythmic method |
| US4277471A (en) * | 1979-03-12 | 1981-07-07 | Eli Lilly And Company | 1,1-Biphenyl-2-yl alkylamines, formulations and antiarrhythmic treatment |
| DE3010152A1 (de) * | 1980-03-17 | 1981-09-24 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Quaternaere 1,1-diphenyl-4-pyrrolidinium-butin-(2)-salze, verfahren zu ihrer herstellung und diese verbindungen enthaltendes arzneimittel |
| US4452745A (en) * | 1981-02-06 | 1984-06-05 | Eli Lilly And Company | 9-Aminoalkylfluorenes |
| DE3373466D1 (de) * | 1982-06-10 | 1987-10-15 | Beecham Wuelfing Gmbh & Co Kg | Amine derivatives |
| DE3444837A1 (de) * | 1984-12-08 | 1986-06-12 | Basf Ag, 6700 Ludwigshafen | 10,11-dihydro-5h-dibenzo(a,d)cycloheptadien- derivate, ihre herstellung und verwendung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3395146A (en) * | 1965-02-11 | 1968-07-30 | Warner Lambert Pharmaceutical | 4-substituted-2-benzhydryl-2-butanol derivatives |
| US3433836A (en) * | 1966-01-14 | 1969-03-18 | Rexall Drug Chemical | Alpha-diaryl alpha,omega-alkylene glycol-dilower-alkylamines |
-
1975
- 1975-06-04 US US05/583,819 patent/US4001328A/en not_active Expired - Lifetime
-
1976
- 1976-03-29 GR GR50427A patent/GR58235B/el unknown
- 1976-03-30 ZA ZA761906A patent/ZA761906B/xx unknown
- 1976-03-31 IL IL49319A patent/IL49319A/xx unknown
- 1976-03-31 DK DK152676AA patent/DK138265B/da not_active IP Right Cessation
- 1976-04-01 CA CA249,358A patent/CA1042921A/en not_active Expired
- 1976-04-02 AU AU12613/76A patent/AU1261376A/en not_active Expired
- 1976-04-21 PT PT65030A patent/PT65030B/pt unknown
- 1976-04-23 PH PH18359A patent/PH12074A/en unknown
- 1976-04-26 SE SE7604781*7A patent/SE7604781L/xx unknown
- 1976-04-30 AR AR263170A patent/AR211122A1/es active
- 1976-05-27 JP JP51062197A patent/JPS51143651A/ja active Pending
- 1976-05-28 GB GB22229/76A patent/GB1547195A/en not_active Expired
- 1976-05-31 RO RO7686310A patent/RO70076A/ro unknown
- 1976-06-01 FR FR7616470A patent/FR2313022A1/fr active Granted
- 1976-06-01 CS CS763642A patent/CS191308B2/cs unknown
- 1976-06-02 DE DE19762624783 patent/DE2624783A1/de not_active Withdrawn
- 1976-06-02 AT AT404376A patent/AT342034B/de not_active IP Right Cessation
- 1976-06-02 BE BE1007423A patent/BE842484A/xx unknown
- 1976-06-03 NL NL7606043A patent/NL7606043A/xx not_active Application Discontinuation
- 1976-06-03 PL PL1976190095A patent/PL100181B1/pl unknown
- 1976-06-04 DD DD193189A patent/DD125200A5/xx unknown
- 1976-06-04 ES ES448594A patent/ES448594A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AR211122A1 (es) | 1977-10-31 |
| PT65030B (en) | 1977-09-12 |
| BE842484A (fr) | 1976-12-02 |
| SE7604781L (sv) | 1976-12-05 |
| DE2624783A1 (de) | 1976-12-16 |
| IL49319A (en) | 1979-07-25 |
| GR58235B (en) | 1977-08-31 |
| CS191308B2 (en) | 1979-06-29 |
| RO70076A (ro) | 1982-09-09 |
| JPS51143651A (en) | 1976-12-10 |
| US4001328A (en) | 1977-01-04 |
| DK138265C (en, 2012) | 1979-01-15 |
| DK152676A (en, 2012) | 1976-12-05 |
| ES448594A1 (es) | 1977-07-16 |
| IL49319A0 (en) | 1976-05-31 |
| DD125200A5 (en, 2012) | 1977-04-06 |
| GB1547195A (en) | 1979-06-06 |
| DK138265B (da) | 1978-08-07 |
| FR2313022A1 (fr) | 1976-12-31 |
| NL7606043A (nl) | 1976-12-07 |
| AU1261376A (en) | 1977-10-06 |
| PL100181B1 (pl) | 1978-09-30 |
| FR2313022B1 (en, 2012) | 1978-11-17 |
| PT65030A (en) | 1976-05-01 |
| PH12074A (en) | 1978-10-30 |
| ATA404376A (de) | 1977-07-15 |
| ZA761906B (en) | 1977-11-30 |
| AT342034B (de) | 1978-03-10 |
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