CH617178A5 - Process for the preparation of novel N-substituted 1,1-diphenyl-4-aminobutanes - Google Patents

Process for the preparation of novel N-substituted 1,1-diphenyl-4-aminobutanes Download PDF

Info

Publication number: CH617178A5
Authority: CH; Switzerland
Prior art keywords: diphenyl; preparation; chlorobutane; phenyl; ethyl alcohol
Prior art date: 1974-12-24

Application number

CH1674675A

Other languages

German (de)

English (en)

Inventor

Bryan Barnet Molloy

Original Assignee

Lilly Co Eli

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.)

1974-12-24

Filing date

1975-12-23

Publication date

1980-05-14

1975-12-23 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1980-05-14 Publication of CH617178A5 publication Critical patent/CH617178A5/de

Links

238000002360 preparation method Methods 0.000 title claims description 13
238000000034 method Methods 0.000 title claims description 11
-1 N-substituted 1,1-diphenyl-4-aminobutanes Chemical class 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 11
235000019441 ethanol Nutrition 0.000 claims description 7
239000002168 alkylating agent Substances 0.000 claims description 6
229940100198 alkylating agent Drugs 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
150000003512 tertiary amines Chemical class 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
SZFDQMKAGLCYPA-UHFFFAOYSA-N 1-phenylbutylbenzene Chemical class C=1C=CC=CC=1C(CCC)C1=CC=CC=C1 SZFDQMKAGLCYPA-UHFFFAOYSA-N 0.000 claims description 3
DGLUAEDLHDOMGZ-UHFFFAOYSA-N 4,4-diphenyl-n-propylbutan-1-amine Chemical compound C=1C=CC=CC=1C(CCCNCCC)C1=CC=CC=C1 DGLUAEDLHDOMGZ-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
XFJKINZMXDNUFF-UHFFFAOYSA-N 4,4-diphenyl-n,n-di(propan-2-yl)butan-1-amine Chemical compound C=1C=CC=CC=1C(CCCN(C(C)C)C(C)C)C1=CC=CC=C1 XFJKINZMXDNUFF-UHFFFAOYSA-N 0.000 claims description 2
AFIZMZOXTJHRRS-UHFFFAOYSA-N 4,4-diphenyl-n-propan-2-ylbutan-1-amine Chemical compound C=1C=CC=CC=1C(CCCNC(C)C)C1=CC=CC=C1 AFIZMZOXTJHRRS-UHFFFAOYSA-N 0.000 claims description 2
ZGLKLPLIOSWYRB-UHFFFAOYSA-N n,n-dibutyl-4,4-diphenylbutan-1-amine Chemical compound C=1C=CC=CC=1C(CCCN(CCCC)CCCC)C1=CC=CC=C1 ZGLKLPLIOSWYRB-UHFFFAOYSA-N 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
NSTSGBQUBLGFCK-UHFFFAOYSA-N n-tert-butyl-4,4-diphenylbutan-1-amine Chemical compound C=1C=CC=CC=1C(CCCNC(C)(C)C)C1=CC=CC=C1 NSTSGBQUBLGFCK-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 3
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims 2
229940043279 diisopropylamine Drugs 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
235000002639 sodium chloride Nutrition 0.000 description 11
206010003119 arrhythmia Diseases 0.000 description 9
MAAQGZFMFXQVOG-UHFFFAOYSA-N 4,4-diphenylbutan-1-amine Chemical class C=1C=CC=CC=1C(CCCN)C1=CC=CC=C1 MAAQGZFMFXQVOG-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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 6
238000004458 analytical method Methods 0.000 description 5
239000003416 antiarrhythmic agent Substances 0.000 description 5
239000002253 acid Substances 0.000 description 4
REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 4
229960000244 procainamide Drugs 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
KISZTEOELCMZPY-UHFFFAOYSA-N 3,3-diphenylpropylamine Chemical class C=1C=CC=CC=1C(CCN)C1=CC=CC=C1 KISZTEOELCMZPY-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000006793 arrhythmia Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
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 3
239000003085 diluting agent Substances 0.000 description 3
229960001404 quinidine Drugs 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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 2
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
230000002921 anti-spasmodic effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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 2
239000000969 carrier Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000008121 dextrose Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
229960004194 lidocaine Drugs 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000000376 reactant Substances 0.000 description 2
206010047302 ventricular tachycardia Diseases 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
JLNYNSOPLYOWFA-UHFFFAOYSA-N (4-chloro-1-phenylbutyl)benzene Chemical compound C=1C=CC=CC=1C(CCCCl)C1=CC=CC=C1 JLNYNSOPLYOWFA-UHFFFAOYSA-N 0.000 description 1
BTUGGGLMQBJCBN-UHFFFAOYSA-N 1-iodo-2-methylpropane Chemical compound CC(C)CI BTUGGGLMQBJCBN-UHFFFAOYSA-N 0.000 description 1
SGHZJRPNPDELFN-UHFFFAOYSA-N 1-n-(2,3-dihydro-1h-inden-2-yl)-2-n,2-n-diethyl-1-n-phenylpropane-1,2-diamine Chemical compound C1C2=CC=CC=C2CC1N(CC(C)N(CC)CC)C1=CC=CC=C1 SGHZJRPNPDELFN-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
METDARXMBAVAMO-UHFFFAOYSA-N 4,4-diphenyl-n-propan-2-ylbutan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCCNC(C)C)C1=CC=CC=C1 METDARXMBAVAMO-UHFFFAOYSA-N 0.000 description 1
UCMCLRBGUKHFCE-UHFFFAOYSA-N 4,4-diphenylbutyl-di(propan-2-yl)azanium;acetate Chemical compound CC([O-])=O.C=1C=CC=CC=1C(CCC[NH+](C(C)C)C(C)C)C1=CC=CC=C1 UCMCLRBGUKHFCE-UHFFFAOYSA-N 0.000 description 1
YROSALVSXNXBQV-UHFFFAOYSA-N 4,4-diphenylbutyl-di(propan-2-yl)azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCCN(C(C)C)C(C)C)C1=CC=CC=C1 YROSALVSXNXBQV-UHFFFAOYSA-N 0.000 description 1
DSHTXTSWOKCZQK-UHFFFAOYSA-N 4,4-diphenylbutyl-methyl-di(propan-2-yl)azanium Chemical compound C=1C=CC=CC=1C(CCC[N+](C)(C(C)C)C(C)C)C1=CC=CC=C1 DSHTXTSWOKCZQK-UHFFFAOYSA-N 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
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
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 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
208000010201 Exanthema Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
229940035674 anesthetics Drugs 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940124575 antispasmodic agent Drugs 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000037396 body weight Effects 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
201000005884 exanthem Diseases 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
230000002600 fibrillogenic effect Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
UPFUYTJILWRHIS-UHFFFAOYSA-N n-butyl-4,4-diphenylbutan-1-amine Chemical compound C=1C=CC=CC=1C(CCCNCCCC)C1=CC=CC=C1 UPFUYTJILWRHIS-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
206010037844 rash Diseases 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
208000003663 ventricular fibrillation Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton

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)

CH1674675A 1974-12-24 1975-12-23 Process for the preparation of novel N-substituted 1,1-diphenyl-4-aminobutanes CH617178A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US53628474A	1974-12-24	1974-12-24

Publications (1)

Publication Number	Publication Date
CH617178A5 true CH617178A5 (en)	1980-05-14

Family

ID=24137881

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1674675A CH617178A5 (en)	1974-12-24	1975-12-23	Process for the preparation of novel N-substituted 1,1-diphenyl-4-aminobutanes

Country Status (10)

Country	Link
JP (1)	JPS5188949A (fr)
BE (1)	BE837042A (fr)
CA (1)	CA1065342A (fr)
CH (1)	CH617178A5 (fr)
DE (1)	DE2557182A1 (fr)
FR (1)	FR2295740A1 (fr)
GB (1)	GB1530807A (fr)
IE (1)	IE42028B1 (fr)
IL (1)	IL48378A (fr)
NL (1)	NL7514675A (fr)

1975
- 1975-10-24 CA CA238,295A patent/CA1065342A/fr not_active Expired
- 1975-10-24 IE IE2324/75A patent/IE42028B1/en unknown
- 1975-10-29 IL IL48378A patent/IL48378A/xx unknown
- 1975-12-16 NL NL7514675A patent/NL7514675A/xx not_active Application Discontinuation
- 1975-12-18 GB GB51966/75A patent/GB1530807A/en not_active Expired
- 1975-12-18 DE DE19752557182 patent/DE2557182A1/de not_active Withdrawn
- 1975-12-22 JP JP50153912A patent/JPS5188949A/ja active Pending
- 1975-12-23 CH CH1674675A patent/CH617178A5/de not_active IP Right Cessation
- 1975-12-23 BE BE1007104A patent/BE837042A/fr unknown
- 1975-12-24 FR FR7539715A patent/FR2295740A1/fr active Granted

Also Published As

Publication number	Publication date
FR2295740B1 (fr)	1980-05-16
JPS5188949A (en)	1976-08-04
IE42028B1 (en)	1980-05-21
IE42028L (en)	1976-06-24
GB1530807A (en)	1978-11-01
IL48378A (en)	1978-09-29
BE837042A (fr)	1976-06-23
CA1065342A (fr)	1979-10-30
IL48378A0 (en)	1975-12-31
FR2295740A1 (fr)	1976-07-23
DE2557182A1 (de)	1976-07-01
NL7514675A (nl)	1976-06-28

Legal Events

Date	Code	Title	Description
1983-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2500110C2 (fr)	1987-06-11
DE2305092C2 (fr)	1987-10-01
DE1593579B1 (de)	1972-02-03	Hydroxy-cyclohexylamine,deren physiologisch vertraeglichen Saeureadditionssalze und Verfahren zu ihrer Herstellung
DE2640972A1 (de)	1977-04-14	Aminoaethanolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2720545C3 (de)	1980-09-11	Derivate des 2,4-Diamino-6,7-dimethoxychinazolins, ihre Herstellung und pharmazeutische Mittel
DE1911464C3 (de)	1975-10-09	3,4-Dihydroisochinoline, Verfahren zu ihrer Herstellung und Arzneimittel
EP0553384B1 (fr)	1995-03-29	Acétylsalicyloyl carnitine et procédé pour sa préparation
US4034011A (en)	1977-07-05	1,1-Diphenyl-4-(substituted-amino)butanes
DE2314335A1 (de)	1973-10-11	Neue amide der apovincaminsaeure, deren salze, herstellung und medikamente, die diese enthalten
CH617178A5 (en)	1980-05-14	Process for the preparation of novel N-substituted 1,1-diphenyl-4-aminobutanes
DE2305870A1 (de)	1973-08-23	Amide, verfahren zu deren herstellung und sie enthaltende pharmazeutische mittel
DE2618223C2 (fr)	1989-08-17
DE2605824C3 (de)	1981-04-23	N-Acylaniline, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen
CH641167A5 (en)	1984-02-15	N-Cyano-N'-(2-((4-methyl-5-imidazolyl)-methylthio)ethyl)-N''-alkyny l guanidines
AT278785B (de)	1970-02-10	Verfahren zur Herstellung von neuen Piperidinderivaten und ihren Salzen
DE3043446C2 (fr)	1989-01-05
DE2360475B2 (de)	1980-03-06	Arzneimittel zur Behandlung von Herzrhytmusstörungen
AT278790B (de)	1970-02-10	Verfahren zur Herstellung von neuen Piperidinderivaten und ihren Salzen
DE2701417A1 (de)	1977-07-28	Pharmazeutische zubereitungen enthaltend sandwicin, isosandwicin oder neue derivate davon, diese neuen derivate und verfahren zu ihrer herstellung
DE2638849A1 (de)	1977-03-17	Aminosaeureester, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2515548A1 (de)	1975-10-23	Quaternaere ammoniumsalze von n-dialkylaminoalkyl-n-(2-indanyl)-anilinen und verfahren zu ihrer herstellung
AT350526B (de)	1979-06-11	Verfahren zur herstellung von neuen 2-amino-1- phenylaethanolen -(1) und von deren salzen
DE2221281A1 (de)	1972-11-16	Pyrazolderivate und Verfahren zu ihrer Herstellung
AT281023B (de)	1970-05-11	Verfahren zur Herstellung von neuen Piperidinderivaten und ihren Salzen
DE2003353B2 (de)	1979-02-01	Phenylisopropylaminoäthanol-Derivate, deren Herstellungsverfahren und Arzneimittel auf deren Basis