DD149664A5 - Verfahren zur herstellung von 1,1'-biphenyl-2-yl-alkylamin-derivaten - Google Patents
Verfahren zur herstellung von 1,1'-biphenyl-2-yl-alkylamin-derivaten Download PDFInfo
- Publication number
- DD149664A5 DD149664A5 DD80219615A DD21961580A DD149664A5 DD 149664 A5 DD149664 A5 DD 149664A5 DD 80219615 A DD80219615 A DD 80219615A DD 21961580 A DD21961580 A DD 21961580A DD 149664 A5 DD149664 A5 DD 149664A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- formula
- biphenyl
- hydrogen
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000008569 process Effects 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- -1 biphenylyl Chemical group 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 230000009467 reduction Effects 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000007818 Grignard reagent Substances 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 4
- 239000011630 iodine Chemical group 0.000 claims description 4
- 229910052740 iodine Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- ZPJOZHLGBGQIGE-UHFFFAOYSA-N 2-(2-phenylphenyl)-5-(propan-2-ylamino)pentanamide Chemical compound CC(C)NCCCC(C(N)=O)C1=CC=CC=C1C1=CC=CC=C1 ZPJOZHLGBGQIGE-UHFFFAOYSA-N 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
- 101150065749 Churc1 gene Proteins 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 102100038239 Protein Churchill Human genes 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 16
- 206010003119 arrhythmia Diseases 0.000 abstract description 14
- 238000002360 preparation method Methods 0.000 abstract description 13
- 238000010992 reflux Methods 0.000 abstract description 11
- 230000006793 arrhythmia Effects 0.000 abstract description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- CXWCBHHZRPQIBG-UHFFFAOYSA-N 4-(dimethylamino)-1-(4-fluoro-2-phenylphenyl)butan-1-ol Chemical compound CN(C)CCCC(O)C1=CC=C(F)C=C1C1=CC=CC=C1 CXWCBHHZRPQIBG-UHFFFAOYSA-N 0.000 abstract description 3
- HPIMKRCDFOQWLK-UHFFFAOYSA-N 4-fluoro-2-phenylbenzaldehyde Chemical group FC1=CC=C(C=O)C(C=2C=CC=CC=2)=C1 HPIMKRCDFOQWLK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 235000019270 ammonium chloride Nutrition 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- FYJHGWMFZQFNBO-UHFFFAOYSA-N 1-(2-phenylphenyl)-4-(propan-2-ylamino)butan-1-ol Chemical compound CC(C)NCCCC(O)C1=CC=CC=C1C1=CC=CC=C1 FYJHGWMFZQFNBO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 103
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 28
- 238000004458 analytical method Methods 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241000282472 Canis lupus familiaris Species 0.000 description 8
- 239000003416 antiarrhythmic agent Substances 0.000 description 8
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- LCRCBXLHWTVPEQ-UHFFFAOYSA-N 2-phenylbenzaldehyde Chemical compound O=CC1=CC=CC=C1C1=CC=CC=C1 LCRCBXLHWTVPEQ-UHFFFAOYSA-N 0.000 description 7
- 239000012259 ether extract Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000002168 alkylating agent Substances 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 6
- WVYPDPJNPRIPPW-UHFFFAOYSA-N 2-(2-phenylphenyl)acetonitrile Chemical compound N#CCC1=CC=CC=C1C1=CC=CC=C1 WVYPDPJNPRIPPW-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- KOUJWSKHBMHJBI-UHFFFAOYSA-N 2-[2-(2-phenylphenyl)ethyl]oxirane Chemical compound C1OC1CCC1=CC=CC=C1C1=CC=CC=C1 KOUJWSKHBMHJBI-UHFFFAOYSA-N 0.000 description 4
- JOYZWXABRPLEOO-UHFFFAOYSA-N 5-(dimethylamino)-2-(2-phenylphenyl)pentanenitrile Chemical compound CN(C)CCCC(C#N)C1=CC=CC=C1C1=CC=CC=C1 JOYZWXABRPLEOO-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 230000033764 rhythmic process Effects 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012670 alkaline solution 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
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- MRCAAFFMZODJBP-UHFFFAOYSA-N 1-fluoro-3-phenylbenzene Chemical group FC1=CC=CC(C=2C=CC=CC=2)=C1 MRCAAFFMZODJBP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- LJCZKXHOWUNNOP-UHFFFAOYSA-N 3-(dimethylamino)-1-(2-phenylphenyl)propan-1-ol Chemical compound CN(C)CCC(O)C1=CC=CC=C1C1=CC=CC=C1 LJCZKXHOWUNNOP-UHFFFAOYSA-N 0.000 description 2
- OIGANBQJQSPHOI-UHFFFAOYSA-N 3-amino-1-(2-phenylphenyl)propan-1-one Chemical compound NCCC(=O)C1=CC=CC=C1C1=CC=CC=C1 OIGANBQJQSPHOI-UHFFFAOYSA-N 0.000 description 2
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
- MMNGVZMJMJPHDO-UHFFFAOYSA-N 6-chloro-2-(2-phenylphenyl)hexanenitrile Chemical compound ClCCCCC(C#N)C1=CC=CC=C1C1=CC=CC=C1 MMNGVZMJMJPHDO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 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
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 238000009115 maintenance therapy Methods 0.000 description 2
- 239000000155 melt Substances 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
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FDZIAOZYPWAXEM-UHFFFAOYSA-N n,n-dimethyl-4-(2-phenylphenyl)but-3-en-1-amine Chemical compound CN(C)CCC=CC1=CC=CC=C1C1=CC=CC=C1 FDZIAOZYPWAXEM-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 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
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup 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
- 230000009466 transformation Effects 0.000 description 2
- OBAGDHZPZLEISV-TXZACQIRSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-5,14-dihydroxy-3-[(4r,6r)-4-methoxy-6-methyl-5-[(1s,2s,3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxyoxan-2-yl]oxy-8,9,13-trimethyl-17-(5-oxo-2h-furan-3-yl)-2,3,4,6,7,11,12,15,16,17-decahydro-1h-cyclopenta[a]phena Chemical compound C1([C@H]2CC[C@@]3(O)[C@]4(C)CC[C@]5([C@]([C@]4(CC[C@@]32C)C)(C=O)CC[C@@H](C5)OC2C[C@H](C([C@@H](C)O2)O[C@@H]2[C@H]([C@H](O)[C@@H](O)[C@H](CO)C2)O)OC)O)=CC(=O)OC1 OBAGDHZPZLEISV-TXZACQIRSA-N 0.000 description 1
- WSFUIHNEBHEGKR-UHFFFAOYSA-N 1,1'-biphenyl;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1C1=CC=CC=C1 WSFUIHNEBHEGKR-UHFFFAOYSA-N 0.000 description 1
- JPYLTKSQEFJVMI-UHFFFAOYSA-N 1,1'-biphenyl;pyrrolidine Chemical compound C1CCNC1.C1=CC=CC=C1C1=CC=CC=C1 JPYLTKSQEFJVMI-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- XZWYAMYRMMMHKM-UHFFFAOYSA-N 1-(2-phenylphenyl)ethanone Chemical group CC(=O)C1=CC=CC=C1C1=CC=CC=C1 XZWYAMYRMMMHKM-UHFFFAOYSA-N 0.000 description 1
- KXHSDJNTGQMREK-UHFFFAOYSA-N 1-(4-bromo-2-phenylphenyl)-3-[methyl(2-phenylethyl)amino]propan-1-ol Chemical compound C=1C=CC=CC=1CCN(C)CCC(O)C1=CC=C(Br)C=C1C1=CC=CC=C1 KXHSDJNTGQMREK-UHFFFAOYSA-N 0.000 description 1
- BFGIPIDZSPTNHJ-UHFFFAOYSA-N 1-(4-fluoro-2-phenylphenyl)-4-[methyl(propyl)amino]butan-1-ol Chemical compound CCCN(C)CCCC(O)C1=CC=C(F)C=C1C1=CC=CC=C1 BFGIPIDZSPTNHJ-UHFFFAOYSA-N 0.000 description 1
- UETXACJZEUHMGL-UHFFFAOYSA-N 1-[di(propan-2-yl)amino]-4-(2-phenylphenyl)butan-2-ol Chemical compound CC(C)N(C(C)C)CC(O)CCC1=CC=CC=C1C1=CC=CC=C1 UETXACJZEUHMGL-UHFFFAOYSA-N 0.000 description 1
- WZEXBDRUCFODAA-UHFFFAOYSA-N 1-bromo-2-methylbut-2-ene Chemical compound CC=C(C)CBr WZEXBDRUCFODAA-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- IOTSUPCKXFUGPA-UHFFFAOYSA-N 1-but-3-enyl-2-phenylbenzene Chemical compound C=CCCC1=CC=CC=C1C1=CC=CC=C1 IOTSUPCKXFUGPA-UHFFFAOYSA-N 0.000 description 1
- CZHLPWNZCJEPJB-UHFFFAOYSA-N 1-chloro-3-methylbutane Chemical compound CC(C)CCCl CZHLPWNZCJEPJB-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- QRSCZDYKRLEMTG-UHFFFAOYSA-N 2-(2-phenylphenyl)-4-(propan-2-ylamino)butanamide Chemical compound CC(C)NCCC(C(N)=O)C1=CC=CC=C1C1=CC=CC=C1 QRSCZDYKRLEMTG-UHFFFAOYSA-N 0.000 description 1
- ZZLWPWTXDDLGFM-UHFFFAOYSA-N 2-(4-bromo-2-phenylphenyl)-5-[hex-3-enyl(2-phenylethyl)amino]pentanamide Chemical compound C=1C=CC=CC=1CCN(CCC=CCC)CCCC(C(N)=O)C1=CC=C(Br)C=C1C1=CC=CC=C1 ZZLWPWTXDDLGFM-UHFFFAOYSA-N 0.000 description 1
- SFRAIJFILIIWPH-UHFFFAOYSA-N 2-(4-chloro-2-phenylphenyl)-5-(propan-2-ylamino)pentanenitrile Chemical compound CC(C)NCCCC(C#N)C1=CC=C(Cl)C=C1C1=CC=CC=C1 SFRAIJFILIIWPH-UHFFFAOYSA-N 0.000 description 1
- WRQSDKWDLLIYJX-UHFFFAOYSA-N 2-(4-chloro-2-phenylphenyl)-5-[methyl(3-methylbutyl)amino]pentan-2-ol Chemical compound CC(C)CCN(C)CCCC(C)(O)C1=CC=C(Cl)C=C1C1=CC=CC=C1 WRQSDKWDLLIYJX-UHFFFAOYSA-N 0.000 description 1
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical class C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- URKFGTNBWFGZHS-UHFFFAOYSA-N 3-(4-bromo-2-phenylphenyl)-n-methyl-n-(2-phenylethyl)prop-2-en-1-amine Chemical compound C=1C=C(Br)C=C(C=2C=CC=CC=2)C=1C=CCN(C)CCC1=CC=CC=C1 URKFGTNBWFGZHS-UHFFFAOYSA-N 0.000 description 1
- MPJWCMSYXDNQNQ-UHFFFAOYSA-N 3-(4-bromo-2-phenylphenyl)-n-methyl-n-(2-phenylethyl)propan-1-amine Chemical compound C=1C=CC=CC=1CCN(C)CCCC1=CC=C(Br)C=C1C1=CC=CC=C1 MPJWCMSYXDNQNQ-UHFFFAOYSA-N 0.000 description 1
- BCCRGCLVAWAJBP-UHFFFAOYSA-N 3-(dimethylamino)-1-(2-phenylphenyl)propan-1-one Chemical compound CN(C)CCC(=O)C1=CC=CC=C1C1=CC=CC=C1 BCCRGCLVAWAJBP-UHFFFAOYSA-N 0.000 description 1
- CMHOWZMKCHMFAY-UHFFFAOYSA-N 3-amino-1-(2-phenylphenyl)propan-1-ol Chemical class NCCC(O)C1=CC=CC=C1C1=CC=CC=C1 CMHOWZMKCHMFAY-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
- NMWSKOLWZZWHPL-UHFFFAOYSA-N 3-chlorobiphenyl Chemical group ClC1=CC=CC(C=2C=CC=CC=2)=C1 NMWSKOLWZZWHPL-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 description 1
- RGCKJSPKMTWLLX-UHFFFAOYSA-N 3-iodopropylbenzene Chemical compound ICCCC1=CC=CC=C1 RGCKJSPKMTWLLX-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FTWYMCSVOSHJPQ-UHFFFAOYSA-N 4-(2-phenylphenyl)pentyl-propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH2+]CCCC(C)C1=CC=CC=C1C1=CC=CC=C1 FTWYMCSVOSHJPQ-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
- RTGGFSACULACFT-UHFFFAOYSA-N 4-(3-methylbutylamino)-1-(2-phenylphenyl)but-2-yn-1-ol Chemical compound CC(C)CCNCC#CC(O)C1=CC=CC=C1C1=CC=CC=C1 RTGGFSACULACFT-UHFFFAOYSA-N 0.000 description 1
- LGVHQWNTXCGPDQ-UHFFFAOYSA-N 4-(3-methylbutylamino)-1-(2-phenylphenyl)butan-1-ol Chemical compound CC(C)CCNCCCC(O)C1=CC=CC=C1C1=CC=CC=C1 LGVHQWNTXCGPDQ-UHFFFAOYSA-N 0.000 description 1
- QXADQTGDAQEHAB-UHFFFAOYSA-N 4-(dibutylamino)-2-(2-phenylphenyl)butanenitrile Chemical compound CCCCN(CCCC)CCC(C#N)C1=CC=CC=C1C1=CC=CC=C1 QXADQTGDAQEHAB-UHFFFAOYSA-N 0.000 description 1
- RLTLNKMOZZCYCJ-UHFFFAOYSA-N 4-[benzyl(2-phenylethyl)amino]-2-(2-phenylphenyl)butanenitrile Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(C#N)CCN(CC=1C=CC=CC=1)CCC1=CC=CC=C1 RLTLNKMOZZCYCJ-UHFFFAOYSA-N 0.000 description 1
- REYMTACOMYLABG-UHFFFAOYSA-N 4-amino-1-(2-phenylphenyl)butan-1-ol Chemical class NCCCC(O)C1=CC=CC=C1C1=CC=CC=C1 REYMTACOMYLABG-UHFFFAOYSA-N 0.000 description 1
- KHYJBLWBMNNRRS-UHFFFAOYSA-N 4-amino-2-(2-phenylphenyl)butanenitrile Chemical compound NCCC(C#N)C1=CC=CC=C1C1=CC=CC=C1 KHYJBLWBMNNRRS-UHFFFAOYSA-N 0.000 description 1
- GBDGONCLNBINAC-UHFFFAOYSA-N 4-chloro-2-phenylbenzaldehyde Chemical compound ClC1=CC=C(C=O)C(C=2C=CC=CC=2)=C1 GBDGONCLNBINAC-UHFFFAOYSA-N 0.000 description 1
- QDSLUQROKPIWTE-UHFFFAOYSA-N 5-(dimethylamino)-2-(2-phenylphenyl)pentanamide Chemical compound CN(C)CCCC(C(N)=O)C1=CC=CC=C1C1=CC=CC=C1 QDSLUQROKPIWTE-UHFFFAOYSA-N 0.000 description 1
- LOARCWQGFGOTCP-UHFFFAOYSA-N 5-(dimethylamino)-2-(2-phenylphenyl)pentanoic acid Chemical compound CN(C)CCCC(C(O)=O)C1=CC=CC=C1C1=CC=CC=C1 LOARCWQGFGOTCP-UHFFFAOYSA-N 0.000 description 1
- UIYILECLPVCEFT-UHFFFAOYSA-N 5-[benzyl(propan-2-yl)amino]-2-(4-chloro-2-phenylphenyl)pentanenitrile Chemical compound C=1C=CC=CC=1CN(C(C)C)CCCC(C#N)C1=CC=C(Cl)C=C1C1=CC=CC=C1 UIYILECLPVCEFT-UHFFFAOYSA-N 0.000 description 1
- WXQZBKQGZJZADT-UHFFFAOYSA-N 5-[di(propan-2-yl)amino]-2-(2-phenylphenyl)pentanamide Chemical compound CC(C)N(C(C)C)CCCC(C(N)=O)C1=CC=CC=C1C1=CC=CC=C1 WXQZBKQGZJZADT-UHFFFAOYSA-N 0.000 description 1
- ZNBAVEPMVYYVSY-UHFFFAOYSA-N 5-amino-2-(2-phenylphenyl)pentanenitrile Chemical compound NCCCC(C#N)C1=CC=CC=C1C1=CC=CC=C1 ZNBAVEPMVYYVSY-UHFFFAOYSA-N 0.000 description 1
- BTZNWKCNDBNWIM-UHFFFAOYSA-N 5-iodopent-2-ene Chemical compound CC=CCCI BTZNWKCNDBNWIM-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VLQBZZYXIIHJIP-UHFFFAOYSA-N CN(C)CCC[Mg] Chemical compound CN(C)CCC[Mg] VLQBZZYXIIHJIP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 240000001879 Digitalis lutea Species 0.000 description 1
- HWBLTYHIEYOAOL-UHFFFAOYSA-N Diisopropyl sulfate Chemical compound CC(C)OS(=O)(=O)OC(C)C HWBLTYHIEYOAOL-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 238000007309 Fischer-Speier esterification reaction Methods 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 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
- UDHWSNPUZBMNQX-UHFFFAOYSA-N [2-hydroxy-4-(2-phenylphenyl)butyl]-propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH2+]CC(O)CCC1=CC=CC=C1C1=CC=CC=C1 UDHWSNPUZBMNQX-UHFFFAOYSA-N 0.000 description 1
- PAAWBWHTJJDHDR-UHFFFAOYSA-N [4-hydroxy-4-(2-phenylphenyl)butyl]-di(propan-2-yl)azanium;chloride Chemical compound [Cl-].CC(C)[NH+](C(C)C)CCCC(O)C1=CC=CC=C1C1=CC=CC=C1 PAAWBWHTJJDHDR-UHFFFAOYSA-N 0.000 description 1
- MHLGRFLUDPEJSA-UHFFFAOYSA-M [4-hydroxy-4-(2-phenylphenyl)butyl]-dimethyl-propan-2-ylazanium;iodide Chemical compound [I-].CC(C)[N+](C)(C)CCCC(O)C1=CC=CC=C1C1=CC=CC=C1 MHLGRFLUDPEJSA-UHFFFAOYSA-M 0.000 description 1
- QCRSZDFJYURUJK-UHFFFAOYSA-N [4-hydroxy-4-(2-phenylphenyl)butyl]-dimethylazanium;chloride Chemical compound [Cl-].C[NH+](C)CCCC(O)C1=CC=CC=C1C1=CC=CC=C1 QCRSZDFJYURUJK-UHFFFAOYSA-N 0.000 description 1
- DQUHCCAEFWTUIR-UHFFFAOYSA-N [4-hydroxy-4-(2-phenylphenyl)butyl]-methyl-propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH+](C)CCCC(O)C1=CC=CC=C1C1=CC=CC=C1 DQUHCCAEFWTUIR-UHFFFAOYSA-N 0.000 description 1
- CQYBTWBRMNLYLB-UHFFFAOYSA-N [Cl-].C1(=C(C=CC=C1)[NH2+]CCCC)C1=CC=CC=C1 Chemical compound [Cl-].C1(=C(C=CC=C1)[NH2+]CCCC)C1=CC=CC=C1 CQYBTWBRMNLYLB-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000005014 aminoalkynyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 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
- 229960004957 aprindine Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003126 arrythmogenic effect Effects 0.000 description 1
- 239000012298 atmosphere 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- YLBIBZCIFHPPKA-UHFFFAOYSA-N but-2-yn-1-amine Chemical compound CC#CCN YLBIBZCIFHPPKA-UHFFFAOYSA-N 0.000 description 1
- MKEXLMVYRUNCQJ-UHFFFAOYSA-N but-3-en-1-amine;hydrochloride Chemical compound [Cl-].[NH3+]CCC=C MKEXLMVYRUNCQJ-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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 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
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- JEEJMQKJTYEELK-UHFFFAOYSA-N dimethyl-[4-(2-phenylphenyl)butyl]azanium;chloride Chemical compound Cl.CN(C)CCCCC1=CC=CC=C1C1=CC=CC=C1 JEEJMQKJTYEELK-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- TWDGDSPUFZAHPR-UHFFFAOYSA-N ethylbenzene;sulfuric acid Chemical compound OS(O)(=O)=O.CCC1=CC=CC=C1 TWDGDSPUFZAHPR-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- UPQNPBHYPACBSK-UHFFFAOYSA-N methylsulfinylmethane;sodium Chemical compound [Na].CS(C)=O UPQNPBHYPACBSK-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- FMJXAYHLEUROOM-UHFFFAOYSA-N n-butyl-2-phenylaniline Chemical compound CCCCNC1=CC=CC=C1C1=CC=CC=C1 FMJXAYHLEUROOM-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- BQMKURIMSKNDLR-UHFFFAOYSA-N n-prop-2-ynylpropan-2-amine Chemical compound CC(C)NCC#C BQMKURIMSKNDLR-UHFFFAOYSA-N 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
- 239000002547 new drug Substances 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- RTWCHRMHGXBETA-UHFFFAOYSA-N prop-1-yn-1-amine Chemical class CC#CN RTWCHRMHGXBETA-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- DMFMZFFIQRMJQZ-UHFFFAOYSA-N pyrrolidin-1-ium;iodide Chemical compound [I-].C1CC[NH2+]C1 DMFMZFFIQRMJQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- CWXOAQXKPAENDI-UHFFFAOYSA-N sodium methylsulfinylmethylide Chemical group [Na+].CS([CH2-])=O CWXOAQXKPAENDI-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SRWFBFUYENBCGF-UHFFFAOYSA-M sodium;chloride;hydrochloride Chemical compound [Na+].Cl.[Cl-] SRWFBFUYENBCGF-UHFFFAOYSA-M 0.000 description 1
- UJTRRNALUYKHQE-UHFFFAOYSA-N sodium;diphenylmethylbenzene Chemical compound [Na+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 UJTRRNALUYKHQE-UHFFFAOYSA-N 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- 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
- C07D295/092—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 with aromatic radicals attached to the chain
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1953479A | 1979-03-12 | 1979-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD149664A5 true DD149664A5 (de) | 1981-07-22 |
Family
ID=21793713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80219615A DD149664A5 (de) | 1979-03-12 | 1980-03-12 | Verfahren zur herstellung von 1,1'-biphenyl-2-yl-alkylamin-derivaten |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP0015776B1 (cs) |
| JP (1) | JPS55127347A (cs) |
| KR (1) | KR840000103B1 (cs) |
| AR (1) | AR228852A1 (cs) |
| AT (1) | AT367395B (cs) |
| AU (1) | AU528060B2 (cs) |
| BE (1) | BE882167A (cs) |
| CA (1) | CA1144926A (cs) |
| CH (1) | CH644094A5 (cs) |
| CS (1) | CS215052B2 (cs) |
| DD (1) | DD149664A5 (cs) |
| DE (1) | DE3060611D1 (cs) |
| DK (1) | DK103480A (cs) |
| ES (6) | ES8105262A1 (cs) |
| FI (1) | FI800736A7 (cs) |
| FR (1) | FR2451363A1 (cs) |
| GB (1) | GB2046256B (cs) |
| GR (1) | GR68036B (cs) |
| HU (1) | HU180334B (cs) |
| IE (1) | IE49552B1 (cs) |
| IL (1) | IL59557A (cs) |
| IT (1) | IT1140773B (cs) |
| LU (1) | LU82237A1 (cs) |
| MX (1) | MX6219E (cs) |
| NZ (1) | NZ193079A (cs) |
| PH (1) | PH14749A (cs) |
| PL (1) | PL121662B1 (cs) |
| PT (1) | PT70928A (cs) |
| RO (1) | RO79906A (cs) |
| SU (2) | SU940645A3 (cs) |
| ZA (1) | ZA801421B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100470454B1 (ko) * | 2002-05-14 | 2005-02-05 | 대한민국 | 돼지 사료공급을 위한 자동조절급이기 |
| EP1768951A4 (en) * | 2004-06-17 | 2011-06-15 | Musc Found For Res Dev | NON-NATURAL AMINO ACIDS |
| EP2511273B8 (en) * | 2011-04-15 | 2019-06-26 | Hivih | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
| EP2821104A1 (en) | 2013-07-05 | 2015-01-07 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES236010A1 (es) * | 1956-06-29 | 1957-12-16 | Lab Pharmaceutica Dr C Janssen | UN PROCEDIMIENTO PARA PREPARAR NUEVOS DERIVADOS PARASIMPATICOLiTICAMENTE ACTIVOS DE ALFAS-DEFENIL PROPANO |
| US3433836A (en) * | 1966-01-14 | 1969-03-18 | Rexall Drug Chemical | Alpha-diaryl alpha,omega-alkylene glycol-dilower-alkylamines |
| GB1475314A (en) * | 1973-11-02 | 1977-06-01 | Cm Ind | Phenyl-propylamine derivatives |
| IL48319A0 (en) * | 1974-10-26 | 1975-12-31 | Merck Patent Gmbh | Araliphatic nitrogen compounds and a process for their preparation |
| GB1523655A (en) * | 1975-02-10 | 1978-09-06 | Armour Pharma | 4-(4-biphenylyl) butylamines and treatment of the animal organism therewith |
-
1980
- 1980-03-09 IL IL59557A patent/IL59557A/xx unknown
- 1980-03-10 CH CH186880A patent/CH644094A5/fr not_active IP Right Cessation
- 1980-03-10 RO RO80100427A patent/RO79906A/ro unknown
- 1980-03-10 GR GR61387A patent/GR68036B/el unknown
- 1980-03-10 CA CA000347365A patent/CA1144926A/en not_active Expired
- 1980-03-10 PT PT70928A patent/PT70928A/pt unknown
- 1980-03-10 AU AU56302/80A patent/AU528060B2/en not_active Ceased
- 1980-03-10 FR FR8005311A patent/FR2451363A1/fr active Granted
- 1980-03-10 NZ NZ193079A patent/NZ193079A/xx unknown
- 1980-03-10 PH PH23743A patent/PH14749A/en unknown
- 1980-03-10 HU HU8080563A patent/HU180334B/hu unknown
- 1980-03-10 LU LU82237A patent/LU82237A1/fr unknown
- 1980-03-11 IT IT20503/80A patent/IT1140773B/it active
- 1980-03-11 GB GB8008170A patent/GB2046256B/en not_active Expired
- 1980-03-11 BE BE1/9747A patent/BE882167A/fr not_active IP Right Cessation
- 1980-03-11 CS CS801665A patent/CS215052B2/cs unknown
- 1980-03-11 AT AT0134580A patent/AT367395B/de not_active IP Right Cessation
- 1980-03-11 IE IE493/80A patent/IE49552B1/en unknown
- 1980-03-11 EP EP80300744A patent/EP0015776B1/en not_active Expired
- 1980-03-11 FI FI800736A patent/FI800736A7/fi not_active Application Discontinuation
- 1980-03-11 ZA ZA00801421A patent/ZA801421B/xx unknown
- 1980-03-11 DK DK103480A patent/DK103480A/da not_active Application Discontinuation
- 1980-03-11 JP JP3256880A patent/JPS55127347A/ja active Pending
- 1980-03-11 PL PL1980222601A patent/PL121662B1/pl unknown
- 1980-03-11 DE DE8080300744T patent/DE3060611D1/de not_active Expired
- 1980-03-12 DD DD80219615A patent/DD149664A5/de unknown
- 1980-03-12 SU SU802892804A patent/SU940645A3/ru active
- 1980-03-12 ES ES489469A patent/ES8105262A1/es not_active Expired
- 1980-03-12 MX MX808706U patent/MX6219E/es unknown
- 1980-03-12 AR AR280280A patent/AR228852A1/es active
- 1980-03-12 KR KR1019800001023A patent/KR840000103B1/ko not_active Expired
- 1980-11-27 ES ES497207A patent/ES8201526A1/es not_active Expired
- 1980-11-27 ES ES497209A patent/ES497209A0/es active Granted
- 1980-11-27 ES ES497210A patent/ES8201529A1/es not_active Expired
- 1980-11-27 ES ES497206A patent/ES8201525A1/es not_active Expired
- 1980-11-27 ES ES497208A patent/ES8201527A1/es not_active Expired
-
1981
- 1981-01-14 SU SU813229052A patent/SU1022655A3/ru active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69003397T2 (de) | Cyclische Aminverbindungen und ihre Verwendung. | |
| DE1443599A1 (de) | Ungesaettigte Amine | |
| DE2047658C3 (de) | 2-Styryl- und 2-Phenyläthinylbenzylaminderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE1593901B2 (de) | Basisch substituierte benzofurane oder indole und verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel | |
| AT368131B (de) | Verfahren zur herstellung von neuen 9-aminoalkyl- fluorenen und von deren salzen | |
| EP0033156B1 (de) | 1-Phenyl-2-cyclohexen-1-alkylamin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE2044172C3 (de) | Pyrrolderivate, ein Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE4027052C2 (cs) | ||
| DE2623314C2 (de) | 1-Aryloxy-2-Hydroxy-3-aminopropane, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DD149664A5 (de) | Verfahren zur herstellung von 1,1'-biphenyl-2-yl-alkylamin-derivaten | |
| CH650249A5 (de) | Basische oximaether, solche enthaltende pharmazeutische praeparate und verfahren zur herstellung derselben. | |
| AT389872B (de) | Verfahren zur herstellung von neuen substituierten 2-phenylmethylen-1aminoalkyloximinocycloalkanen und deren saeureadditionssalzen | |
| DE2540552A1 (de) | Cycloalkylderivate von 1-aryloxy-3- amino-2-propanolen | |
| DE2833892A1 (de) | 12h-dibenzo eckige klammer auf d,g eckige klammer zu eckige klammer auf 1,3,6 eckige klammer zu dioxazocinderivate, solche enthaltende arzneimittel und verfahren zur herstellung derselben | |
| EP0152556A1 (de) | Aminopropanolderivate von substituierten 2-Hydroxy-propiophenonen, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel | |
| DE2919495C2 (cs) | ||
| DD144764A5 (de) | Verfahren zur herstellung von r-n-(2-phenyl-2-hydroxyethyl)-3-phenylpropylaminen | |
| DE3027338C2 (de) | Isochinolinderivate, ihre Salze, Verfahren zu ihrer Herstellung und therapeutische Zubereitung | |
| DE1095283B (de) | Verfahren zur Herstellung von Phenthiazinderivaten | |
| DE1593392C3 (de) | Neue vom 9,10-Äthano-9,10-dihydroanthracen abgeleitete Aminoäther und deren Salze sowie Verfahren zu ihrer Herstellung | |
| DE2704794C3 (de) | Aminopropanolderivate des 4-Hydroxy-l^-benzisothiazols | |
| WO2002016308A1 (de) | Phenyl- und phenylalkyl-substituierte ethanolamine und ethylendiamine | |
| CH643536A5 (de) | Alkanolaminderivate. | |
| DE1593901C3 (de) | Basisch substituierte Benzofurane oder Indole und Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel | |
| AT238181B (de) | Verfahren zur Herstellung neuer Pyrrolidinverbindungen |