CH493463A - Verfahren zur Herstellung von Naphtalinderivaten - Google Patents
Verfahren zur Herstellung von NaphtalinderivatenInfo
- Publication number
- CH493463A CH493463A CH1436263A CH1436263A CH493463A CH 493463 A CH493463 A CH 493463A CH 1436263 A CH1436263 A CH 1436263A CH 1436263 A CH1436263 A CH 1436263A CH 493463 A CH493463 A CH 493463A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- naphthoxy
- carbon atoms
- propanol
- ether
- Prior art date
Links
- 239000000674 adrenergic antagonist Substances 0.000 title abstract 2
- 230000000747 cardiac effect Effects 0.000 title abstract 2
- 230000004064 dysfunction Effects 0.000 title abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title 2
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- -1 hydroxyalkyl radical Chemical class 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 238000001953 recrystallisation Methods 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 238000002844 melting Methods 0.000 claims description 16
- 230000008018 melting Effects 0.000 claims description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 14
- 150000002790 naphthalenes Chemical class 0.000 claims description 14
- 239000005711 Benzoic acid Substances 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 235000010233 benzoic acid Nutrition 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000002244 precipitate Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 7
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000003840 hydrochlorides Chemical class 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- GRDPPSMNRDZCGL-ODZAUARKSA-N (z)-but-2-enedioic acid;propan-2-ol Chemical compound CC(C)O.OC(=O)\C=C/C(O)=O GRDPPSMNRDZCGL-ODZAUARKSA-N 0.000 claims description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 2
- QJQZRLXDLORINA-UHFFFAOYSA-N 2-cyclohexylethanol Chemical compound OCCC1CCCCC1 QJQZRLXDLORINA-UHFFFAOYSA-N 0.000 claims description 2
- RURKHEGTHHTXJT-UHFFFAOYSA-N 2-naphthalen-1-yloxypropanoyl chloride Chemical compound C1=CC=C2C(OC(C)C(Cl)=O)=CC=CC2=C1 RURKHEGTHHTXJT-UHFFFAOYSA-N 0.000 claims description 2
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 claims description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims description 2
- XQVCEJHOJRCOQF-UHFFFAOYSA-N C(C)(C)O.C(CCCCC(=O)O)(=O)O Chemical compound C(C)(C)O.C(CCCCC(=O)O)(=O)O XQVCEJHOJRCOQF-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 2
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000003893 lactate salts Chemical class 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 150000003873 salicylate salts Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- 239000000057 synthetic resin Substances 0.000 claims description 2
- 150000003892 tartrate salts Chemical class 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 4
- 239000004593 Epoxy Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000003891 oxalate salts Chemical class 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HCEHQXSJDJLURS-UHFFFAOYSA-N butan-2-ol;hydrochloride Chemical compound Cl.CCC(C)O HCEHQXSJDJLURS-UHFFFAOYSA-N 0.000 description 4
- 229940075930 picrate Drugs 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000003901 oxalic acid esters Chemical class 0.000 description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- ZOORULWLQVVPOJ-UHFFFAOYSA-N 2-naphthalen-1-yloxyacetyl chloride Chemical compound C1=CC=C2C(OCC(=O)Cl)=CC=CC2=C1 ZOORULWLQVVPOJ-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 description 1
- BHDSGQOSIWVMJW-UHFFFAOYSA-N 1-(2-chloroethoxy)propane Chemical compound CCCOCCCl BHDSGQOSIWVMJW-UHFFFAOYSA-N 0.000 description 1
- RLZQUFPUZJVDLV-UHFFFAOYSA-N 1-chloro-3-methyl-3-naphthalen-1-yloxybutan-2-ol Chemical compound C1=CC=C2C(OC(C)(C)C(O)CCl)=CC=CC2=C1 RLZQUFPUZJVDLV-UHFFFAOYSA-N 0.000 description 1
- SZIHMOBFLHVKTR-UHFFFAOYSA-N 1-chloro-3-naphthalen-1-yloxybutan-2-ol Chemical compound C1=CC=C2C(OC(C)C(O)CCl)=CC=CC2=C1 SZIHMOBFLHVKTR-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- QYYCPWLLBSSFBW-UHFFFAOYSA-N 2-(naphthalen-1-yloxymethyl)oxirane Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1CO1 QYYCPWLLBSSFBW-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- WGXRLJQIXNXFSY-UHFFFAOYSA-N 2-methyl-2-naphthalen-1-yloxypropanoic acid Chemical compound C1=CC=C2C(OC(C)(C)C(O)=O)=CC=CC2=C1 WGXRLJQIXNXFSY-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WWQQMNLUXJUAOD-UHFFFAOYSA-N 3-bromo-1-naphthalen-1-yloxybutan-2-ol Chemical compound C1=CC=C2C(OCC(O)C(Br)C)=CC=CC2=C1 WWQQMNLUXJUAOD-UHFFFAOYSA-N 0.000 description 1
- KBURFWJPNOHKRB-UHFFFAOYSA-N 3-bromo-1-naphthalen-1-yloxybutan-2-one Chemical compound C1=CC=C2C(OCC(=O)C(Br)C)=CC=CC2=C1 KBURFWJPNOHKRB-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- DMVIFYPLIZNLPU-UHFFFAOYSA-N C(C(=O)O)(=O)O.C(CC)O Chemical compound C(C(=O)O)(=O)O.C(CC)O DMVIFYPLIZNLPU-UHFFFAOYSA-N 0.000 description 1
- JIQBIGFTHSCMAT-UHFFFAOYSA-N CCOC(C)=O.OC(=O)C(O)=O Chemical compound CCOC(C)=O.OC(=O)C(O)=O JIQBIGFTHSCMAT-UHFFFAOYSA-N 0.000 description 1
- JXRKYQOHZHUBLY-UHFFFAOYSA-N CO.NCCCCl Chemical compound CO.NCCCCl JXRKYQOHZHUBLY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000003945 chlorohydrins Chemical class 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH740567A CH509971A (de) | 1962-11-23 | 1963-11-22 | Verfahren zur Herstellung von Naphthalinderivaten |
| CH740667A CH512434A (de) | 1962-11-23 | 1963-11-22 | Verfahren zur Herstellung von Naphthalinderivaten |
| CH106668A CH494736A (de) | 1962-11-23 | 1963-11-22 | Verfahren zur Herstellung von Naphthalinderivaten |
| CH1378667A CH506481A (de) | 1963-11-22 | 1967-10-03 | Verfahren zur Herstellung von Naphthalinderivaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB44357/62A GB994918A (en) | 1962-11-23 | 1962-11-23 | Naphthoxy-substituted alkanolamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH493463A true CH493463A (de) | 1970-07-15 |
Family
ID=10432900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1436263A CH493463A (de) | 1962-11-23 | 1963-11-22 | Verfahren zur Herstellung von Naphtalinderivaten |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US3337628A (en, 2012) |
| AT (3) | AT246734B (en, 2012) |
| BE (1) | BE640312A (en, 2012) |
| BR (1) | BR6354781D0 (en, 2012) |
| CH (1) | CH493463A (en, 2012) |
| CY (1) | CY339A (en, 2012) |
| DE (1) | DE1493847A1 (en, 2012) |
| DK (4) | DK109992C (en, 2012) |
| ES (1) | ES293736A1 (en, 2012) |
| FI (1) | FI40904B (en, 2012) |
| GB (1) | GB994918A (en, 2012) |
| MY (1) | MY6600009A (en, 2012) |
| NL (1) | NL300886A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002024619A1 (en) * | 2000-09-25 | 2002-03-28 | Btg International Limited | Amine compounds |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6504268A (en, 2012) * | 1965-04-03 | 1966-10-04 | ||
| US3466325A (en) * | 1965-04-30 | 1969-09-09 | Haessle Ab | 1-(ortho-alkenyl phenoxy) - 2-hydroxy-3-isopropylaminopropanes and the salts thereof |
| US3959359A (en) * | 1968-01-23 | 1976-05-25 | Laboratoires Laroche Navarron | Phenoxyalkylamines, process for their preparation and therapeutical composition containing same |
| US3534084A (en) * | 1968-10-16 | 1970-10-13 | Squibb & Sons Inc | Adamantylamino-naphthyloxypropanols and related compounds |
| SE372762B (en, 2012) * | 1969-05-21 | 1975-01-13 | Haessle Ab | |
| US3961072A (en) * | 1969-12-17 | 1976-06-01 | Pfizer Inc. | Phenoxypropanolamine therapeutic agents |
| US3996284A (en) * | 1971-03-23 | 1976-12-07 | Wijbe Thomas Nauta | Naphthyl and tetrahydronaphthyl di-ethers |
| BE790165A (fr) * | 1971-12-14 | 1973-02-15 | Parke Davis & Co | Nouveaux aminoalcanols et procede pour les preparer |
| DE2354444A1 (de) * | 1973-10-31 | 1975-05-07 | Merck Patent Gmbh | Biphenylylaether und verfahren zu ihrer herstellung |
| US4051186A (en) * | 1974-06-20 | 1977-09-27 | The Regents Of The University Of California | Amino-propranolol |
| US4379167A (en) * | 1974-10-25 | 1983-04-05 | A. H. Robins Company, Inc. | 1-Aryloxy-4-amino-2-butanols and the pharmaceutical use thereof |
| DE2505423A1 (de) * | 1975-02-08 | 1976-08-19 | Merck Patent Gmbh | Biphenylylaether und verfahren zu ihrer herstellung |
| US4071552A (en) * | 1976-05-19 | 1978-01-31 | Ayerst Mckenna And Harrison Ltd. | Aryloxy aminobutanols, their preparation and use thereof |
| US4201866A (en) * | 1977-01-17 | 1980-05-06 | American Home Products Corporation | O-Hemi-succinate of propranolol |
| US4463190A (en) * | 1977-07-05 | 1984-07-31 | A. H. Robins Company, Inc. | 1-Aryloxy-4-amino-2-butanols |
| EP0003664B1 (en) * | 1978-02-08 | 1982-02-17 | Imperial Chemical Industries Plc | Alkanolamine derivatives, process for their preparation and pharmaceutical compositions containing them |
| US4241177A (en) * | 1978-08-28 | 1980-12-23 | Syva Company | Propanolol antigen conjugates and antibodies |
| US4585785A (en) * | 1979-01-09 | 1986-04-29 | A. H. Robins Company, Inc. | Cis and trans-3-aryloxy-4-hydroxypyrrolidines used as anti-arrhythmics |
| RO71464A2 (ro) * | 1979-02-23 | 1981-05-15 | Intreprinderea De Medicamente,Ro | Procedeu pentru fabricarea 1-(1-naftoxi) 3-izopropilamino-2-propanolului |
| US4284648A (en) * | 1979-08-03 | 1981-08-18 | The University Of Kentucky Research Foundation | Nasal administration of propranolol |
| DE3068678D1 (en) * | 1979-08-10 | 1984-08-30 | Sandoz Ag | 3-aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them |
| US4376125A (en) * | 1980-11-05 | 1983-03-08 | University Of Virginia Alumni Patents Foundation | Aminobenzlpropranolol and pharmaceutical preparation thereof |
| US4405642A (en) * | 1980-11-28 | 1983-09-20 | American Hospital Supply Corporation | Method for treatment or prophylaxis of cardiac disorders |
| US4321398A (en) * | 1981-05-07 | 1982-03-23 | Mead Johnson & Company | Thienyl and benzothienyl-tertiary butylaminophenoxypropanols |
| US4402974A (en) * | 1981-06-23 | 1983-09-06 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4369175A (en) | 1981-07-27 | 1983-01-18 | Ciba-Geigy Corporation | Process for the manufacture of prolonged action vincamine preparations, the vincamine preparations so obtained, and medicaments containing them |
| FR2521136A1 (fr) * | 1982-02-05 | 1983-08-12 | Synthelabo | Derives de piperidine, leur preparation et leur application en therapeutique |
| IT1212552B (it) * | 1982-10-20 | 1989-11-30 | Italo Britannica L Manet Ti H | Alcanolaminossi derivati di 3,4-diidro-2h-1.4-benzotiazin-3-one, loro procedimento di produzione e loro utilizzazione farmaceutica |
| US4517188A (en) * | 1983-05-09 | 1985-05-14 | Mead Johnson & Company | 1-Pyrimidinyloxy-3-hetaryl-alkylamino-2-propanols |
| NZ208337A (en) * | 1983-06-10 | 1988-10-28 | Bristol Myers Co | 2-(2-hydroxy-3-((2-(ar-hydroxy-1h-aminopropoxy-yl)ethyl benzonitriles and pharmaceutical compositions |
| DE3330005A1 (de) * | 1983-08-19 | 1985-02-28 | Wolfgang Dr. Graz Lindner | Weinsaeuremonoester von optisch aktiven alkanolaminen, verfahren zu ihrer herstellung und ihre verwendung |
| US4593039A (en) * | 1984-04-02 | 1986-06-03 | Merck & Co., Inc. | 1-aryloxy-3-(substituted aminoalkylamino)-2-propanols |
| US4897355A (en) * | 1985-01-07 | 1990-01-30 | Syntex (U.S.A.) Inc. | N[ω,(ω-1)-dialkyloxy]- and N-[ω,(ω-1)-dialkenyloxy]-alk-1-yl-N,N,N-tetrasubstituted ammonium lipids and uses therefor |
| US5550289A (en) * | 1985-01-07 | 1996-08-27 | Syntex (U.S.A.) Inc. | N-(1,(1-1)-dialkyloxy)-and N-(1,(1-1)-dialkenyloxy alk-1-yl-N-N,N-tetrasubstituted ammonium lipids and uses therefor |
| JPS61210063A (ja) * | 1985-03-14 | 1986-09-18 | Mitsubishi Chem Ind Ltd | アリ−ルスルホン類 |
| US5095151A (en) * | 1985-05-21 | 1992-03-10 | American Home Products Corporation | Preparation of propranolol hydrochloride macrocrystals |
| US4888354A (en) * | 1987-12-21 | 1989-12-19 | Theratech, Inc. | Skin penetration enhancement using free base and acid addition salt combinations of active agents |
| US5013761A (en) * | 1988-06-03 | 1991-05-07 | Eli Lilly And Company | Serotonin antagonists |
| US5387613A (en) * | 1993-07-23 | 1995-02-07 | Ribogene, Inc. | Treatment of tachyarrhythmias of supraventricular origin |
| CA2134038C (en) * | 1994-06-16 | 1997-06-03 | David Taiwai Wong | Potentiation of drug response |
| EP0714663A3 (en) | 1994-11-28 | 1997-01-15 | Lilly Co Eli | Potentiation of drug responses by serotonin 1A receptor antagonists |
| DK0759299T3 (da) * | 1995-08-16 | 2000-08-07 | Lilly Co Eli | Potensering af serotoninrespons |
| US5776985A (en) * | 1995-11-16 | 1998-07-07 | The George Washington University | Fluorinated propranolol and related methods |
| US5967613A (en) * | 1997-08-11 | 1999-10-19 | Piccard Corporation | Wheelchair support and attachment system |
| US7022342B2 (en) | 2002-03-28 | 2006-04-04 | Andrx Corporation, Inc. | Controlled release oral dosage form of beta-adrenergic blocking agents |
| DE60336485D1 (de) | 2002-08-19 | 2011-05-05 | Pfizer | Kombinationstherapie gegen hyperproliferative erkrankungen |
| US20050037063A1 (en) * | 2003-07-21 | 2005-02-17 | Bolton Anthony E. | Combined therapies |
| US20060063803A1 (en) * | 2004-09-23 | 2006-03-23 | Pfizer Inc | 4-Amino substituted-2-substituted-1,2,3,4-tetrahydroquinoline compounds |
| US20060182806A1 (en) * | 2004-11-08 | 2006-08-17 | Mintong Guo | Extended-release propranolol composition |
| RU2433823C2 (ru) * | 2005-01-31 | 2011-11-20 | Милан Лэборетериз, Инк. | Фармацевтическая композиция, содержащая гидроксилированный небиволол |
| GT200600381A (es) | 2005-08-25 | 2007-03-28 | Compuestos organicos | |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
| JP5240586B2 (ja) * | 2007-01-29 | 2013-07-17 | ブイライフ サイエンス テクノロジーズ ピーブイティー リミテッド | 糖尿病性合併症治療用薬学的組成物 |
| US9782488B2 (en) * | 2007-03-12 | 2017-10-10 | Nektar Therapeutics | Oligomer-beta blocker conjugates |
| AU2014255381A1 (en) | 2013-04-17 | 2015-10-08 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| EP2959904A1 (en) | 2014-06-27 | 2015-12-30 | Institut De Recerca Contra La Leucemia Josep Carreras | Methods for treating, diagnosing and prognosing a haematological malignancy |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| WO2018161039A1 (en) | 2017-03-03 | 2018-09-07 | Synovo Gmbh | Novel anti-infective and anti-inflammatory compounds |
| US11382875B2 (en) | 2017-04-07 | 2022-07-12 | Lundquist Institute For Biomedical Innovation At Harbor-Ucla Medical Center | Methods and compositions for modulating β-amyloid/α7-nAChR interactions |
| CN113574055B (zh) | 2019-01-18 | 2024-07-23 | 阿斯利康(瑞典)有限公司 | Pcsk9抑制剂及其使用方法 |
| GB2628566A (en) | 2023-03-29 | 2024-10-02 | Novumgen Ltd | An orally rapidly disintegrating tablet of propranolol and its process of preparation |
| US12172963B1 (en) | 2023-08-28 | 2024-12-24 | King Faisal University | N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide as an antimicrobial compound |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB622297A (en) * | 1946-12-06 | 1949-04-29 | British Drug Houses Ltd | Improvements in or relating to the preparation of basic ethers |
| US3033640A (en) * | 1954-06-16 | 1962-05-08 | Saul & Co | Incorporation of an organic basic compound into cellulose acetate materials |
| FR1198123A (fr) * | 1958-06-02 | 1959-12-04 | Rech S Biolog Soc D | Procédé de préparation d'aryloxy-amino-alcools et de leurs dérivés (sels, esters, ammoniums quaternaires) et produits obtenus par la mise en oeuvre de ce procédé |
| GB1023214A (en) * | 1962-12-17 | 1966-03-23 | Ici Ltd | Carbocyclic hydroxyamines |
| GB1069343A (en) * | 1963-09-10 | 1967-05-17 | Ici Ltd | Propanolamine derivatives |
-
0
- NL NL300886D patent/NL300886A/xx unknown
-
1962
- 1962-11-23 GB GB44357/62A patent/GB994918A/en not_active Expired
-
1963
- 1963-11-12 US US323089A patent/US3337628A/en not_active Expired - Lifetime
- 1963-11-18 DE DE19631493847 patent/DE1493847A1/de active Pending
- 1963-11-20 DK DK542563AA patent/DK109992C/da active
- 1963-11-20 DK DK486665AA patent/DK109784C/da active
- 1963-11-21 ES ES0293736A patent/ES293736A1/es not_active Expired
- 1963-11-22 CH CH1436263A patent/CH493463A/de not_active IP Right Cessation
- 1963-11-22 AT AT187765A patent/AT246734B/de active
- 1963-11-22 AT AT187665A patent/AT244949B/de active
- 1963-11-22 AT AT939263A patent/AT244948B/de active
- 1963-11-22 BE BE640312A patent/BE640312A/xx unknown
- 1963-11-22 FI FI2289/63A patent/FI40904B/fi active
- 1963-11-22 BR BR154781/63A patent/BR6354781D0/pt unknown
-
1965
- 1965-09-22 DK DK486465AA patent/DK111203B/da unknown
- 1965-09-22 DK DK486565AA patent/DK111204B/da unknown
-
1966
- 1966-01-12 CY CY33966A patent/CY339A/xx unknown
- 1966-12-31 MY MY19669A patent/MY6600009A/xx unknown
-
1967
- 1967-06-05 US US643356A patent/US3520919A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002024619A1 (en) * | 2000-09-25 | 2002-03-28 | Btg International Limited | Amine compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| NL300886A (en, 2012) | |
| BE640312A (en, 2012) | 1964-05-22 |
| DK111204B (da) | 1968-07-01 |
| FI40904B (en, 2012) | 1969-03-31 |
| US3520919A (en) | 1970-07-21 |
| DK109992C (da) | 1968-08-19 |
| DE1493847A1 (de) | 1971-07-22 |
| US3337628A (en) | 1967-08-22 |
| AT244948B (de) | 1966-02-10 |
| AT246734B (de) | 1966-05-10 |
| ES293736A1 (es) | 1964-03-01 |
| DK109784C (da) | 1968-07-01 |
| MY6600009A (en) | 1966-12-31 |
| GB994918A (en) | 1965-06-10 |
| CY339A (en) | 1966-01-12 |
| AT244949B (de) | 1966-02-10 |
| DK111203B (da) | 1968-07-01 |
| BR6354781D0 (pt) | 1973-07-12 |
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