NO852809L - Fremgangsmaate for fremstilling av terapeutisk aktive aminofenolderivater. - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive aminofenolderivater.Info
- Publication number
- NO852809L NO852809L NO852809A NO852809A NO852809L NO 852809 L NO852809 L NO 852809L NO 852809 A NO852809 A NO 852809A NO 852809 A NO852809 A NO 852809A NO 852809 L NO852809 L NO 852809L
- Authority
- NO
- Norway
- Prior art keywords
- group
- hydroxy
- phenyl
- compounds
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title claims description 20
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 104
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000006239 protecting group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000009467 reduction Effects 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 230000029936 alkylation Effects 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- XPIXHMAEEIVNNX-UHFFFAOYSA-N N-[2-hydroxy-5-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl]phenyl]methanesulfonamide Chemical compound OC1=C(C=C(C=C1)C(CNCCCCCCOCCCCC1=CC=CC=C1)O)NS(=O)(=O)C XPIXHMAEEIVNNX-UHFFFAOYSA-N 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- XNTYOEKOEUKNGG-UHFFFAOYSA-N N-[2-hydroxy-5-[1-hydroxy-2-[6-(3-phenylpropoxy)hexylamino]ethyl]phenyl]formamide Chemical compound OC1=C(C=C(C=C1)C(CNCCCCCCOCCCC1=CC=CC=C1)O)NC=O XNTYOEKOEUKNGG-UHFFFAOYSA-N 0.000 claims description 3
- FOBDUELNQYHFME-UHFFFAOYSA-N N-[2-hydroxy-5-[1-hydroxy-2-[6-(3-phenylpropoxy)hexylamino]ethyl]phenyl]methanesulfonamide Chemical compound OC1=C(C=C(C=C1)C(CNCCCCCCOCCCC1=CC=CC=C1)O)NS(=O)(=O)C FOBDUELNQYHFME-UHFFFAOYSA-N 0.000 claims description 3
- BOUPQKVLQPSSIW-UHFFFAOYSA-N N-[2-hydroxy-5-[1-hydroxy-2-[6-[4-(4-methylphenyl)butoxy]hexylamino]ethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=C(C=CC(=C1)C(CNCCCCCCOCCCCC1=CC=C(C=C1)C)O)O BOUPQKVLQPSSIW-UHFFFAOYSA-N 0.000 claims description 3
- LMBRLMGOSAREMX-UHFFFAOYSA-N N-[2-hydroxy-5-[1-hydroxy-2-[7-(2-phenylethoxy)heptan-2-ylamino]ethyl]phenyl]methanesulfonamide Chemical compound OC1=C(C=C(C=C1)C(CNC(CCCCCOCCC1=CC=CC=C1)C)O)NS(=O)(=O)C LMBRLMGOSAREMX-UHFFFAOYSA-N 0.000 claims description 3
- NKQYAFNPKXWWGH-UHFFFAOYSA-N N-[5-[2-[6-[4-(4-fluorophenyl)butoxy]hexylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=C(C=CC(=C1)C(CNCCCCCCOCCCCC1=CC=C(C=C1)F)O)O NKQYAFNPKXWWGH-UHFFFAOYSA-N 0.000 claims description 3
- UKPAVESWVYLOMG-UHFFFAOYSA-N [2-hydroxy-5-[1-hydroxy-2-[6-(3-phenylpropoxy)hexylamino]ethyl]phenyl]urea Chemical compound OC1=C(C=C(C=C1)C(CNCCCCCCOCCCC1=CC=CC=C1)O)NC(=O)N UKPAVESWVYLOMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- YOMDTGGKYMPBDZ-UHFFFAOYSA-N N-[2-hydroxy-5-[1-hydroxy-2-[3-(6-phenylhexoxy)propylamino]ethyl]phenyl]methanesulfonamide Chemical compound OC1=C(C=C(C=C1)C(CNCCCOCCCCCCC1=CC=CC=C1)O)NS(=O)(=O)C YOMDTGGKYMPBDZ-UHFFFAOYSA-N 0.000 claims description 2
- GEDBNLYFSFZWGU-UHFFFAOYSA-N [2-hydroxy-5-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl]phenyl]urea Chemical compound OC1=C(C=C(C=C1)C(CNCCCCCCOCCCCC1=CC=CC=C1)O)NC(=O)N GEDBNLYFSFZWGU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 235000013405 beer Nutrition 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
- 239000000543 intermediate Substances 0.000 description 45
- 239000000243 solution Substances 0.000 description 35
- 239000000203 mixture Substances 0.000 description 33
- 239000003921 oil Substances 0.000 description 29
- 235000019198 oils Nutrition 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- -1 hydroxy, methoxy Chemical group 0.000 description 27
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000004809 thin layer chromatography Methods 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- 239000013067 intermediate product Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 238000001665 trituration Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000006071 cream Substances 0.000 description 5
- 238000007429 general method Methods 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000005002 aryl methyl group Chemical group 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 4
- 230000008570 general process Effects 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052987 metal hydride Inorganic materials 0.000 description 4
- 150000004681 metal hydrides Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000004936 stimulating effect Effects 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MSZJJGHZRBKVHQ-UHFFFAOYSA-N n-[5-(2-bromoacetyl)-2-phenylmethoxyphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(C(=O)CBr)=CC=C1OCC1=CC=CC=C1 MSZJJGHZRBKVHQ-UHFFFAOYSA-N 0.000 description 3
- JWLIKZBRVQRFNF-UHFFFAOYSA-N n-benzyl-6-(4-phenylbutoxy)hexan-1-amine Chemical compound C=1C=CC=CC=1CNCCCCCCOCCCCC1=CC=CC=C1 JWLIKZBRVQRFNF-UHFFFAOYSA-N 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910003445 palladium oxide Inorganic materials 0.000 description 3
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 238000011946 reduction process Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 2
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 208000000884 Airway Obstruction Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 125000005283 haloketone group Chemical group 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical class O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
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- 150000003890 succinate salts Chemical class 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07C275/40—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 being further substituted by nitrogen atoms not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848417897A GB8417897D0 (en) | 1984-07-13 | 1984-07-13 | Chemical compounds |
| GB848426200A GB8426200D0 (en) | 1984-10-17 | 1984-10-17 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO852809L true NO852809L (no) | 1986-01-14 |
Family
ID=26287982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO852809A NO852809L (no) | 1984-07-13 | 1985-07-12 | Fremgangsmaate for fremstilling av terapeutisk aktive aminofenolderivater. |
Country Status (19)
| Country | Link |
|---|---|
| AU (1) | AU582369B2 (fr) |
| BE (1) | BE902876A (fr) |
| CH (1) | CH665632A5 (fr) |
| DE (1) | DE3524990A1 (fr) |
| DK (1) | DK319885A (fr) |
| ES (2) | ES8609216A1 (fr) |
| FI (1) | FI852755L (fr) |
| FR (1) | FR2567510B1 (fr) |
| GB (1) | GB2162842B (fr) |
| GR (1) | GR851733B (fr) |
| IL (1) | IL75794A (fr) |
| IT (1) | IT1182061B (fr) |
| LU (1) | LU86002A1 (fr) |
| NL (1) | NL8502012A (fr) |
| NO (1) | NO852809L (fr) |
| NZ (1) | NZ212726A (fr) |
| PH (1) | PH22666A (fr) |
| PT (1) | PT80806B (fr) |
| SE (1) | SE8503466L (fr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8426206D0 (en) * | 1984-10-17 | 1984-11-21 | Glaxo Holdings Ltd | Chemical compounds |
| GB8426200D0 (en) * | 1984-10-17 | 1984-11-21 | Glaxo Holdings Ltd | Chemical compounds |
| GB8525484D0 (en) * | 1985-10-16 | 1985-11-20 | Glaxo Group Ltd | Chemical compounds |
| GB8525483D0 (en) * | 1985-10-16 | 1985-11-20 | Glaxo Group Ltd | Chemical compounds |
| US4937268A (en) * | 1987-03-12 | 1990-06-26 | Glaxo Group Limited | Chemical compounds |
| GB8718938D0 (en) * | 1987-08-11 | 1987-09-16 | Glaxo Group Ltd | Chemical compounds |
| PT89239B (pt) * | 1987-12-18 | 1993-07-30 | Glaxo Group Ltd | Processo para a preparacao de drivados de etanolamina |
| ZA889405B (en) * | 1987-12-18 | 1989-12-27 | Glaxo Group Ltd | Ethanolamine derivatives |
| GB8909273D0 (en) * | 1989-04-24 | 1989-06-07 | Glaxo Group Ltd | Chemical compounds |
| GB0103630D0 (en) * | 2001-02-14 | 2001-03-28 | Glaxo Group Ltd | Chemical compounds |
| ATE365720T1 (de) | 2001-03-08 | 2007-07-15 | Glaxo Group Ltd | Agonisten von beta-adrenorezeptoren |
| JP4143413B2 (ja) | 2001-03-22 | 2008-09-03 | グラクソ グループ リミテッド | β２−アドレナリン受容体アゴニストとしてのホルムアニリド誘導体 |
| ES2316599T3 (es) | 2001-09-14 | 2009-04-16 | Glaxo Group Limited | Derivados de fenetanolamina para el tratamiento de enfermedades respiratorias. |
| GB0217225D0 (en) | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicinal compounds |
| DE60320007T2 (de) | 2002-10-28 | 2009-06-18 | Glaxo Group Ltd., Greenford | Phenthanolamin-Derivate zur Behandlung von Atemwegserkrankungen |
| GB0303396D0 (en) | 2003-02-14 | 2003-03-19 | Glaxo Group Ltd | Medicinal compounds |
| GB0329182D0 (en) | 2003-12-17 | 2004-01-21 | Glaxo Group Ltd | Chemical compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR4290M (fr) * | 1964-06-05 | 1966-07-18 | ||
| GB1531718A (en) * | 1974-11-20 | 1978-11-08 | Pharmacia As | Phenylethanolamines |
| ATE1899T1 (de) * | 1979-06-16 | 1982-12-15 | Beecham Group Plc | Sekundaere amine, ihre herstellung und verwendung in pharmazeutischen zusammensetzungen. |
| LU85856A1 (fr) * | 1984-04-17 | 1986-06-11 | Glaxo Group Ltd | Composes de phenethanolamine |
| GB8426206D0 (en) * | 1984-10-17 | 1984-11-21 | Glaxo Holdings Ltd | Chemical compounds |
-
1985
- 1985-07-12 IL IL75794A patent/IL75794A/xx unknown
- 1985-07-12 AU AU44860/85A patent/AU582369B2/en not_active Ceased
- 1985-07-12 NL NL8502012A patent/NL8502012A/nl not_active Application Discontinuation
- 1985-07-12 FR FR858510729A patent/FR2567510B1/fr not_active Expired
- 1985-07-12 DK DK319885A patent/DK319885A/da not_active Application Discontinuation
- 1985-07-12 LU LU86002A patent/LU86002A1/fr unknown
- 1985-07-12 ES ES545162A patent/ES8609216A1/es not_active Expired
- 1985-07-12 GR GR851733A patent/GR851733B/el unknown
- 1985-07-12 NZ NZ212726A patent/NZ212726A/xx unknown
- 1985-07-12 FI FI852755A patent/FI852755L/fi not_active Application Discontinuation
- 1985-07-12 BE BE0/215339A patent/BE902876A/fr not_active IP Right Cessation
- 1985-07-12 PH PH32520A patent/PH22666A/en unknown
- 1985-07-12 SE SE8503466A patent/SE8503466L/ not_active Application Discontinuation
- 1985-07-12 NO NO852809A patent/NO852809L/no unknown
- 1985-07-12 GB GB08517674A patent/GB2162842B/en not_active Expired
- 1985-07-12 DE DE19853524990 patent/DE3524990A1/de not_active Withdrawn
- 1985-07-12 CH CH3022/85A patent/CH665632A5/fr not_active IP Right Cessation
- 1985-07-12 PT PT80806A patent/PT80806B/pt unknown
- 1985-07-12 IT IT48348/85A patent/IT1182061B/it active
-
1986
- 1986-02-17 ES ES552109A patent/ES8707925A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB8517674D0 (en) | 1985-08-21 |
| ES8609216A1 (es) | 1986-09-01 |
| ES552109A0 (es) | 1987-09-01 |
| PH22666A (en) | 1988-11-14 |
| CH665632A5 (fr) | 1988-05-31 |
| GB2162842B (en) | 1988-01-13 |
| NL8502012A (nl) | 1986-02-03 |
| DK319885A (da) | 1986-01-14 |
| IT8548348A0 (it) | 1985-07-12 |
| SE8503466D0 (sv) | 1985-07-12 |
| IT1182061B (it) | 1987-09-30 |
| AU582369B2 (en) | 1989-03-23 |
| ES8707925A1 (es) | 1987-09-01 |
| SE8503466L (sv) | 1986-01-14 |
| FR2567510A1 (fr) | 1986-01-17 |
| PT80806B (en) | 1987-03-26 |
| IL75794A (en) | 1989-01-31 |
| FI852755A0 (fi) | 1985-07-12 |
| ES545162A0 (es) | 1986-09-01 |
| BE902876A (fr) | 1986-01-13 |
| NZ212726A (en) | 1989-02-24 |
| GR851733B (fr) | 1985-11-26 |
| LU86002A1 (fr) | 1986-08-04 |
| FR2567510B1 (fr) | 1989-02-10 |
| DK319885D0 (da) | 1985-07-12 |
| FI852755L (fi) | 1986-01-14 |
| PT80806A (en) | 1985-08-01 |
| IL75794A0 (en) | 1985-11-29 |
| DE3524990A1 (de) | 1986-01-23 |
| GB2162842A (en) | 1986-02-12 |
| AU4486085A (en) | 1986-01-16 |
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