JPS5912113B2 - エタノ−ルアミン誘導体又はその酸付加塩の製法 - Google Patents
エタノ−ルアミン誘導体又はその酸付加塩の製法Info
- Publication number
- JPS5912113B2 JPS5912113B2 JP49071243A JP7124374A JPS5912113B2 JP S5912113 B2 JPS5912113 B2 JP S5912113B2 JP 49071243 A JP49071243 A JP 49071243A JP 7124374 A JP7124374 A JP 7124374A JP S5912113 B2 JPS5912113 B2 JP S5912113B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- carbon atoms
- hydrogen atom
- halogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002169 ethanolamines Chemical class 0.000 title claims description 50
- 239000002253 acid Substances 0.000 title claims description 41
- 150000003839 salts Chemical class 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 65
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000006239 protecting group Chemical group 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 21
- -1 sulfonyloxy Chemical group 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 230000007062 hydrolysis Effects 0.000 claims description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 239000012458 free base Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- 239000000243 solution Substances 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 22
- 239000007858 starting material Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 229960001317 isoprenaline Drugs 0.000 description 12
- 239000012279 sodium borohydride Substances 0.000 description 12
- 229910000033 sodium borohydride Inorganic materials 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- 230000036772 blood pressure Effects 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 208000001871 Tachycardia Diseases 0.000 description 8
- 230000006794 tachycardia Effects 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 241000282326 Felis catus Species 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 239000002024 ethyl acetate extract Substances 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001728 carbonyl compounds Chemical class 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- CPJOTJVGGVYFEF-UHFFFAOYSA-N n-[2-[(2-hydroxy-2-phenylethyl)amino]propyl]-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(O)CNC(C)CNC(=O)CC1=CC=CC=C1 CPJOTJVGGVYFEF-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- JYDHZOIDIWUHDB-UHFFFAOYSA-N 1-(4-phenylpiperidin-4-yl)ethanone;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(C(=O)C)CCNCC1 JYDHZOIDIWUHDB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000009079 Bronchial Spasm Diseases 0.000 description 3
- 208000014181 Bronchial disease Diseases 0.000 description 3
- 206010006482 Bronchospasm Diseases 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 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
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- QZUOKPUQPUDFNS-UHFFFAOYSA-N n-(2-oxopropyl)-2-phenylacetamide Chemical compound CC(=O)CNC(=O)CC1=CC=CC=C1 QZUOKPUQPUDFNS-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- IKVWGJPHXMYGBM-KOLCDFICSA-N (1r)-2-[[(2r)-1-aminopropan-2-yl]amino]-1-phenylethanol Chemical compound NC[C@@H](C)NC[C@H](O)C1=CC=CC=C1 IKVWGJPHXMYGBM-KOLCDFICSA-N 0.000 description 2
- 125000004814 1,1-dimethylethylene group Chemical group [H]C([H])([H])C([*:1])(C([H])([H])[H])C([H])([H])[*:2] 0.000 description 2
- IKVWGJPHXMYGBM-UHFFFAOYSA-N 2-(1-aminopropan-2-ylamino)-1-phenylethanol Chemical compound NCC(C)NCC(O)C1=CC=CC=C1 IKVWGJPHXMYGBM-UHFFFAOYSA-N 0.000 description 2
- FNUGIRFCLRJTGL-UHFFFAOYSA-N 2-(2-aminoethylamino)-1-phenylethanol Chemical compound NCCNCC(O)C1=CC=CC=C1 FNUGIRFCLRJTGL-UHFFFAOYSA-N 0.000 description 2
- ZXAQPQMRUHGIQN-UHFFFAOYSA-N 2-[2-aminopropyl(benzyl)amino]-1-phenylethanol Chemical compound C=1C=CC=CC=1CN(CC(N)C)CC(O)C1=CC=CC=C1 ZXAQPQMRUHGIQN-UHFFFAOYSA-N 0.000 description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-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
- 241000699670 Mus sp. Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000001800 adrenalinergic effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229940047889 isobutyramide Drugs 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- ZIMOHSZCIYGHAR-UHFFFAOYSA-N n-(2-aminoethyl)-2-phenylacetamide Chemical compound NCCNC(=O)CC1=CC=CC=C1 ZIMOHSZCIYGHAR-UHFFFAOYSA-N 0.000 description 2
- WHCBCOGNYOBFIL-UHFFFAOYSA-N n-(2-aminopropyl)-2-phenylacetamide Chemical compound CC(N)CNC(=O)CC1=CC=CC=C1 WHCBCOGNYOBFIL-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 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
- 229940125723 sedative agent Drugs 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MPWKJKJYJHDFLV-KJFJCRTCSA-N (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-2-ol Chemical compound C1CC(O)[C@@]2([H])CC[C@]1([H])N2C MPWKJKJYJHDFLV-KJFJCRTCSA-N 0.000 description 1
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- GESCCEANKMFMEN-UHFFFAOYSA-N n-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]-2-phenoxyacetamide Chemical compound C=1C=CC=CC=1C(O)CNCCNC(=O)COC1=CC=CC=C1 GESCCEANKMFMEN-UHFFFAOYSA-N 0.000 description 1
- VBIHXJQDOUPCHR-UHFFFAOYSA-N n-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(O)CNCCNC(=O)CC1=CC=CC=C1 VBIHXJQDOUPCHR-UHFFFAOYSA-N 0.000 description 1
- UCVVIXVUWIKDCF-UHFFFAOYSA-N n-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]-3-methylbutanamide Chemical compound CC(C)CC(=O)NCCNCC(O)C1=CC=CC=C1 UCVVIXVUWIKDCF-UHFFFAOYSA-N 0.000 description 1
- XDFFVHXTBRAEAI-UHFFFAOYSA-N n-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]propanamide Chemical compound CCC(=O)NCCNCC(O)C1=CC=CC=C1 XDFFVHXTBRAEAI-UHFFFAOYSA-N 0.000 description 1
- NZHOGLCCTGSHLZ-UHFFFAOYSA-N n-[2-[[2-hydroxy-2-(4-methoxyphenyl)ethyl]amino]ethyl]-2-methylpropanamide Chemical compound COC1=CC=C(C(O)CNCCNC(=O)C(C)C)C=C1 NZHOGLCCTGSHLZ-UHFFFAOYSA-N 0.000 description 1
- FPPPCWZMGMMOGW-UHFFFAOYSA-N n-[2-[[2-hydroxy-2-(4-methylphenyl)ethyl]amino]ethyl]propanamide Chemical compound CCC(=O)NCCNCC(O)C1=CC=C(C)C=C1 FPPPCWZMGMMOGW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- HZJCOPSKQTYHCD-UHFFFAOYSA-N oxalic acid;2,2,2-trifluoro-n-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetamide Chemical compound OC(=O)C(O)=O.FC(F)(F)C(=O)NCCNCC(O)C1=CC=CC=C1 HZJCOPSKQTYHCD-UHFFFAOYSA-N 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- QXSAKPUBHTZHKW-UHFFFAOYSA-N para-hydroxybenzamide Natural products NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
- 229960001999 phentolamine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
- 229960001032 trihexyphenidyl Drugs 0.000 description 1
- NFMWFGXCDDYTEG-UHFFFAOYSA-N trimagnesium;diborate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]B([O-])[O-].[O-]B([O-])[O-] NFMWFGXCDDYTEG-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2967973A GB1460593A (en) | 1973-06-22 | 1973-06-22 | Ethanolamine derivatives |
| GB2967973 | 1973-06-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5032138A JPS5032138A (en, 2012) | 1975-03-28 |
| JPS5912113B2 true JPS5912113B2 (ja) | 1984-03-21 |
Family
ID=10295371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49071243A Expired JPS5912113B2 (ja) | 1973-06-22 | 1974-06-21 | エタノ−ルアミン誘導体又はその酸付加塩の製法 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3944611A (en, 2012) |
| JP (1) | JPS5912113B2 (en, 2012) |
| BE (1) | BE816519A (en, 2012) |
| CA (1) | CA1028342A (en, 2012) |
| CH (1) | CH599119A5 (en, 2012) |
| DE (1) | DE2430237C2 (en, 2012) |
| DK (1) | DK141048B (en, 2012) |
| EG (1) | EG11299A (en, 2012) |
| ES (1) | ES427573A1 (en, 2012) |
| FI (1) | FI62529C (en, 2012) |
| FR (1) | FR2233991B1 (en, 2012) |
| GB (1) | GB1460593A (en, 2012) |
| IE (1) | IE39306B1 (en, 2012) |
| IL (1) | IL45054A (en, 2012) |
| LU (1) | LU70358A1 (en, 2012) |
| MW (1) | MW2574A1 (en, 2012) |
| NL (1) | NL178965C (en, 2012) |
| NO (1) | NO742136L (en, 2012) |
| SE (1) | SE417199B (en, 2012) |
| ZA (1) | ZA743686B (en, 2012) |
| ZM (1) | ZM9974A1 (en, 2012) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038313A (en) * | 1970-01-08 | 1977-07-26 | Ciba-Geigy Corporation | Cycloalkylureido phenoxy propanolamines |
| US4117157A (en) * | 1973-06-22 | 1978-09-26 | Imperial Chemical Industries Limited | Ethanolamine derivatives having β-adrenergic blocking activity |
| US4034112A (en) * | 1973-06-22 | 1977-07-05 | Imperial Chemical Industries Limited | Ethanolamine derivatives having β-adrenergic blocking activity |
| US4211724A (en) * | 1973-08-06 | 1980-07-08 | Hoffman-La Roche Inc. | 16-Substituted prostaglandins |
| US4041075A (en) * | 1973-12-12 | 1977-08-09 | Imperial Chemical Industries Limited | Phenoxy-alkanolamine derivatives |
| AT334385B (de) * | 1973-12-20 | 1976-01-10 | Chemie Linz Ag | Verfahren zur herstellung von neuen phenoxypropylaminderivaten und deren salzen |
| US4141987A (en) * | 1974-06-05 | 1979-02-27 | Imperial Chemical Industries Limited | 1-Aryloxy-3-thenamidoalkylamino-2-propanol derivatives |
| GB1521471A (en) * | 1974-06-05 | 1978-08-16 | Randall & Son Ltd J | Token-deposit locks |
| US4145363A (en) * | 1975-02-05 | 1979-03-20 | Yamanouchi Pharmaceutical Co., Ltd. | 4-Carbamoylamino-α-aminomethylbenzyl alcohol derivatives |
| JPS5260487A (en) * | 1975-11-14 | 1977-05-18 | Kajima Corp | Pipe cutting apparatus |
| GB1508208A (en) * | 1975-12-05 | 1978-04-19 | Ici Ltd | Amide derivatives |
| GB1509300A (en) * | 1975-12-05 | 1978-05-04 | Ici Ltd | Ethanolamine derivatives |
| US4115409A (en) * | 1975-12-05 | 1978-09-19 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| IE45991B1 (en) * | 1976-12-16 | 1983-01-26 | Ici Ltd | Esters of hydroxy amino amides |
| US4127674A (en) * | 1977-03-21 | 1978-11-28 | Allergan Pharmaceuticals, Inc. | Method of treatment for glaucoma |
| US4172150A (en) * | 1977-05-23 | 1979-10-23 | Imperial Chemical Industries Limited | Cardiac stimulants |
| EP0000809B1 (en) * | 1977-08-16 | 1982-04-14 | Imperial Chemical Industries Plc | Anti-inflammatory 1-phenylethanolamine derivatives, pharmaceutical compositions thereof and processes for their manufacture |
| US4219561A (en) * | 1977-09-22 | 1980-08-26 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| US4163053A (en) * | 1977-12-27 | 1979-07-31 | Schering Corporation | Anti-hypertensive 5-[2-(substituted anilinoalkylamino)-1-hydroxyalkyl]salicylamides |
| ATE798T1 (de) * | 1978-06-15 | 1982-04-15 | Imperial Chemical Industries Plc | Entzuendungshemmende 1-phe nyl-2-aminoaethanol-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen zur oertlichen anwendung. |
| ZA802552B (en) * | 1979-05-21 | 1981-04-29 | Ici Ltd | 1-phenyl-2-aminoethanol derivatives |
| JPS6043493B2 (ja) * | 1981-10-09 | 1985-09-28 | 新日本製鐵株式会社 | 鋼管矢板の切断方法および切断装置 |
| JPS5931314A (ja) * | 1982-08-13 | 1984-02-20 | Nippon Steel Corp | 鋼管矢板の切断装置 |
| US4943591A (en) * | 1984-10-17 | 1990-07-24 | Glaxo Group Limited | Dichloroaniline derivatives |
| GB8607313D0 (en) * | 1986-03-25 | 1986-04-30 | Ici Plc | Pharmaceutical compositions |
| JPH0673771B2 (ja) * | 1989-05-29 | 1994-09-21 | 科学技術庁原子力局長 | 管切断装置 |
| US5171753A (en) * | 1991-05-15 | 1992-12-15 | A. H. Robins Company, Incorporated | Derivatives of 2-amino-1-phenylethanol having antiulcer activity |
| WO1994008945A1 (de) * | 1992-10-16 | 1994-04-28 | Byk Nederland Bv | Substituierte ethanolaminester |
| CN1984876A (zh) * | 2004-06-03 | 2007-06-20 | 施万制药 | 二胺类β2肾上腺素能受体激动剂 |
| GB0417802D0 (en) * | 2004-08-10 | 2004-09-15 | Novartis Ag | Organic compounds |
| US8115031B2 (en) * | 2007-11-09 | 2012-02-14 | Yates Charles R | Anti-inflammatory quinic acid derivatives for oral administration |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1269775A (en) * | 1968-07-18 | 1972-04-06 | Ici Ltd | Alkanolamine derivatives |
-
1973
- 1973-06-22 GB GB2967973A patent/GB1460593A/en not_active Expired
-
1974
- 1974-06-07 IE IE1203/74A patent/IE39306B1/xx unknown
- 1974-06-10 ZA ZA00743686A patent/ZA743686B/xx unknown
- 1974-06-12 NO NO742136A patent/NO742136L/no unknown
- 1974-06-13 US US05/479,174 patent/US3944611A/en not_active Expired - Lifetime
- 1974-06-18 BE BE145584A patent/BE816519A/xx not_active IP Right Cessation
- 1974-06-18 IL IL45054A patent/IL45054A/en unknown
- 1974-06-18 MW MW25/74A patent/MW2574A1/xx unknown
- 1974-06-19 SE SE7408101A patent/SE417199B/xx not_active IP Right Cessation
- 1974-06-19 LU LU70358A patent/LU70358A1/xx unknown
- 1974-06-20 NL NLAANVRAGE7408261,A patent/NL178965C/xx not_active IP Right Cessation
- 1974-06-20 FI FI1893/74A patent/FI62529C/fi active
- 1974-06-21 CH CH857974A patent/CH599119A5/xx not_active IP Right Cessation
- 1974-06-21 ZM ZM99/74A patent/ZM9974A1/xx unknown
- 1974-06-21 FR FR7421707A patent/FR2233991B1/fr not_active Expired
- 1974-06-21 JP JP49071243A patent/JPS5912113B2/ja not_active Expired
- 1974-06-21 DK DK334874AA patent/DK141048B/da not_active IP Right Cessation
- 1974-06-21 CA CA203,094A patent/CA1028342A/en not_active Expired
- 1974-06-22 ES ES427573A patent/ES427573A1/es not_active Expired
- 1974-06-22 EG EG238/74A patent/EG11299A/xx active
- 1974-06-24 DE DE2430237A patent/DE2430237C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| LU70358A1 (en, 2012) | 1974-10-17 |
| ZM9974A1 (en) | 1976-04-21 |
| IE39306B1 (en) | 1978-09-13 |
| FI189374A7 (en, 2012) | 1974-12-23 |
| ZA743686B (en) | 1975-06-25 |
| ES427573A1 (es) | 1976-12-16 |
| DE2430237A1 (de) | 1975-01-16 |
| FI62529B (fi) | 1982-09-30 |
| NO742136L (en, 2012) | 1975-01-20 |
| SE7408101L (en, 2012) | 1974-12-23 |
| SE417199B (sv) | 1981-03-02 |
| CA1028342A (en) | 1978-03-21 |
| DK141048C (en, 2012) | 1980-06-23 |
| GB1460593A (en) | 1977-01-06 |
| DE2430237C2 (de) | 1984-11-22 |
| BE816519A (fr) | 1974-12-18 |
| IL45054A0 (en) | 1974-09-10 |
| AU7013774A (en) | 1975-12-18 |
| MW2574A1 (en) | 1976-03-10 |
| EG11299A (en) | 1977-01-31 |
| FI62529C (fi) | 1983-01-10 |
| CH599119A5 (en, 2012) | 1978-05-12 |
| JPS5032138A (en, 2012) | 1975-03-28 |
| FR2233991A1 (en, 2012) | 1975-01-17 |
| FR2233991B1 (en, 2012) | 1978-07-21 |
| NL7408261A (en, 2012) | 1974-12-24 |
| US3944611A (en) | 1976-03-16 |
| DK334874A (en, 2012) | 1975-02-17 |
| IL45054A (en) | 1977-10-31 |
| NL178965C (nl) | 1986-06-16 |
| DK141048B (da) | 1979-12-31 |
| IE39306L (en) | 1974-12-22 |
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