SE408794B - Forfarande for framstellning av nya (fenoxi- eller naftyloxi-)propanolamin-derivat med farmakologiska egenskaper - Google Patents

Forfarande for framstellning av nya (fenoxi- eller naftyloxi-)propanolamin-derivat med farmakologiska egenskaper

Info

Publication number: SE408794B
Authority: SE; Sweden
Prior art keywords: radical; hydrogen; hydrogen atom; carbon atoms; ethyl acetate
Prior art date: 1972-12-15

Application number

SE7316863A

Other languages

English (en)

Swedish (sv)

Inventor

L H Smith

Original Assignee

Ici Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1972-12-15

Filing date

1973-12-13

Publication date

1979-07-09

1973-12-13 Application filed by Ici Ltd filed Critical Ici Ltd

1979-07-09 Publication of SE408794B publication Critical patent/SE408794B/sv

Links

238000000034 method Methods 0.000 title claims description 44
238000002360 preparation method Methods 0.000 title claims description 5
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 title claims description 3
230000000144 pharmacologic effect Effects 0.000 title 1
150000003152 propanolamines Chemical class 0.000 title 1
-1 alkylene radical Chemical class 0.000 claims description 186
239000000203 mixture Substances 0.000 claims description 105
150000001875 compounds Chemical class 0.000 claims description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
239000007858 starting material Substances 0.000 claims description 44
229910052739 hydrogen Inorganic materials 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 38
125000004432 carbon atom Chemical group C* 0.000 claims description 37
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
150000003254 radicals Chemical class 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 25
125000006239 protecting group Chemical group 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 21
150000001412 amines Chemical class 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 12
239000012458 free base Substances 0.000 claims description 10
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
238000007327 hydrogenolysis reaction Methods 0.000 claims description 7
150000001728 carbonyl compounds Chemical class 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
239000000460 chlorine Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
239000002243 precursor Substances 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
125000005277 alkyl imino group Chemical group 0.000 claims description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
125000005702 oxyalkylene group Chemical group 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
239000007789 gas Substances 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 286
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 207
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 112
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 58
230000008018 melting Effects 0.000 description 58
238000002844 melting Methods 0.000 description 58
239000000243 solution Substances 0.000 description 46
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
238000002425 crystallisation Methods 0.000 description 36
230000008025 crystallization Effects 0.000 description 36
239000002904 solvent Substances 0.000 description 36
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 35
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 28
229960004592 isopropanol Drugs 0.000 description 27
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
239000007787 solid Substances 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
238000000354 decomposition reaction Methods 0.000 description 19
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 18
239000000706 filtrate Substances 0.000 description 17
238000010992 reflux Methods 0.000 description 17
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 16
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
235000006408 oxalic acid Nutrition 0.000 description 13
239000003208 petroleum Substances 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
239000000284 extract Substances 0.000 description 11
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
239000003085 diluting agent Substances 0.000 description 9
229960001317 isoprenaline Drugs 0.000 description 9
239000002585 base Substances 0.000 description 8
230000000903 blocking effect Effects 0.000 description 8
230000000747 cardiac effect Effects 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
ANBZWDBEKOZNHY-UHFFFAOYSA-N ethanol;oxalic acid Chemical compound CCO.OC(=O)C(O)=O ANBZWDBEKOZNHY-UHFFFAOYSA-N 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 7
239000000499 gel Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
229940124630 bronchodilator Drugs 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000003840 hydrochlorides Chemical class 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000003701 inert diluent Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
HYWONZSREFAXIL-UHFFFAOYSA-N n-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NCCNCC(O)COC1=CC=CC=C1 HYWONZSREFAXIL-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
230000004936 stimulating effect Effects 0.000 description 4
239000000126 substance Substances 0.000 description 4
ZQQSYPZAPHRXRY-UHFFFAOYSA-N 1-hydroxyazetidine Chemical class ON1CCC1 ZQQSYPZAPHRXRY-UHFFFAOYSA-N 0.000 description 3
ZULYWHOJRVBUJU-UHFFFAOYSA-N 2-aminoethylurea Chemical compound NCCNC(N)=O ZULYWHOJRVBUJU-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
HKRONTUQBMLTMG-UHFFFAOYSA-N acetonitrile;oxalic acid Chemical compound CC#N.OC(=O)C(O)=O HKRONTUQBMLTMG-UHFFFAOYSA-N 0.000 description 3
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
239000000401 methanolic extract Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000010453 quartz Substances 0.000 description 3
230000007017 scission Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
OPCJOXGBLDJWRM-UHFFFAOYSA-N 1,2-diamino-2-methylpropane Chemical compound CC(C)(N)CN OPCJOXGBLDJWRM-UHFFFAOYSA-N 0.000 description 2
JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 2
YZKMURMKJCXVIE-UHFFFAOYSA-N 1-(2-aminoethyl)-3-phenylurea Chemical compound NCCNC(=O)NC1=CC=CC=C1 YZKMURMKJCXVIE-UHFFFAOYSA-N 0.000 description 2
HCTDRZMGZRHFJV-UHFFFAOYSA-N 1-chloro-3-phenoxypropan-2-ol Chemical compound ClCC(O)COC1=CC=CC=C1 HCTDRZMGZRHFJV-UHFFFAOYSA-N 0.000 description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 2
SXZMAVLCDKNPTD-UHFFFAOYSA-N 2-oxo-2-propan-2-yloxyacetic acid Chemical compound CC(C)OC(=O)C(O)=O SXZMAVLCDKNPTD-UHFFFAOYSA-N 0.000 description 2
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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 compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
DMNPVZLYSRBARL-UHFFFAOYSA-N C(C)(=O)OCC.C(C(=O)O)(=O)OC(C)C Chemical compound C(C)(=O)OCC.C(C(=O)O)(=O)OC(C)C DMNPVZLYSRBARL-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-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
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000000150 Sympathomimetic Substances 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
229960002179 ephedrine Drugs 0.000 description 2
VZULMGQWPFBTBK-UHFFFAOYSA-N ethanol 2-oxo-2-propoxyacetic acid Chemical compound C(C)O.C(C(=O)O)(=O)OCCC VZULMGQWPFBTBK-UHFFFAOYSA-N 0.000 description 2
SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
150000003947 ethylamines Chemical class 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
238000005192 partition Methods 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
230000001975 sympathomimetic effect Effects 0.000 description 2
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IKTHDUWAAWNNBS-UHFFFAOYSA-N n-(2-aminoethyl)-2,5-bis(phenylmethoxy)benzamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(C(=O)NCCN)=CC=1OCC1=CC=CC=C1 IKTHDUWAAWNNBS-UHFFFAOYSA-N 0.000 description 1
KMFVUBFMFJOFIN-UHFFFAOYSA-N n-(2-aminoethyl)-2-methylpropanamide Chemical compound CC(C)C(=O)NCCN KMFVUBFMFJOFIN-UHFFFAOYSA-N 0.000 description 1
CAEALSAPHDTRRY-UHFFFAOYSA-N n-(2-aminoethyl)-2-phenoxyacetamide;hydrochloride Chemical compound Cl.NCCNC(=O)COC1=CC=CC=C1 CAEALSAPHDTRRY-UHFFFAOYSA-N 0.000 description 1
OFNOTKBTVZPDMU-UHFFFAOYSA-N n-(2-aminoethyl)-2-phenylacetamide;hydrochloride Chemical compound Cl.NCCNC(=O)CC1=CC=CC=C1 OFNOTKBTVZPDMU-UHFFFAOYSA-N 0.000 description 1
BCGXHHYBXMQECD-UHFFFAOYSA-N n-(2-aminoethyl)benzamide;hydrochloride Chemical compound Cl.NCCNC(=O)C1=CC=CC=C1 BCGXHHYBXMQECD-UHFFFAOYSA-N 0.000 description 1
UMNPKLARCNEUAI-UHFFFAOYSA-N n-(2-aminoethyl)benzenesulfonamide;hydrochloride Chemical compound Cl.NCCNS(=O)(=O)C1=CC=CC=C1 UMNPKLARCNEUAI-UHFFFAOYSA-N 0.000 description 1
WYZXJFFDMNRBEP-UHFFFAOYSA-N n-(2-aminoethyl)cyclopentanecarboxamide Chemical compound NCCNC(=O)C1CCCC1 WYZXJFFDMNRBEP-UHFFFAOYSA-N 0.000 description 1
SFOOQDKGASYPRW-UHFFFAOYSA-N n-(2-aminoethyl)cyclopentanecarboxamide;oxalic acid Chemical compound OC(=O)C(O)=O.NCCNC(=O)C1CCCC1 SFOOQDKGASYPRW-UHFFFAOYSA-N 0.000 description 1
DTSMHNPPSHGIAA-UHFFFAOYSA-N n-(2-aminoethyl)methanesulfonamide;oxalic acid Chemical compound OC(=O)C(O)=O.CS(=O)(=O)NCCN DTSMHNPPSHGIAA-UHFFFAOYSA-N 0.000 description 1
JLBZBBHCZAODDD-UHFFFAOYSA-N n-(2-aminopropyl)-2-methylpropanamide Chemical compound CC(N)CNC(=O)C(C)C JLBZBBHCZAODDD-UHFFFAOYSA-N 0.000 description 1
WHCBCOGNYOBFIL-UHFFFAOYSA-N n-(2-aminopropyl)-2-phenylacetamide Chemical compound CC(N)CNC(=O)CC1=CC=CC=C1 WHCBCOGNYOBFIL-UHFFFAOYSA-N 0.000 description 1
OIRGFQCXUNWNRF-UHFFFAOYSA-N n-(2-aminopropyl)acetamide Chemical compound CC(N)CNC(C)=O OIRGFQCXUNWNRF-UHFFFAOYSA-N 0.000 description 1
XETWPZRFZHJXAF-UHFFFAOYSA-N n-(2-aminopropyl)benzenesulfonamide Chemical compound CC(N)CNS(=O)(=O)C1=CC=CC=C1 XETWPZRFZHJXAF-UHFFFAOYSA-N 0.000 description 1
QZUOKPUQPUDFNS-UHFFFAOYSA-N n-(2-oxopropyl)-2-phenylacetamide Chemical compound CC(=O)CNC(=O)CC1=CC=CC=C1 QZUOKPUQPUDFNS-UHFFFAOYSA-N 0.000 description 1
DFZLBZMBJIUOJZ-UHFFFAOYSA-N n-(4-aminobutyl)-2-methylpropanamide Chemical compound CC(C)C(=O)NCCCCN DFZLBZMBJIUOJZ-UHFFFAOYSA-N 0.000 description 1
IAIREXADHABZAE-UHFFFAOYSA-N n-(5-amino-4-hydroxy-2-methyl-5-phenoxypentyl)benzenesulfonamide Chemical compound C=1C=CC=CC=1OC(N)C(O)CC(C)CNS(=O)(=O)C1=CC=CC=C1 IAIREXADHABZAE-UHFFFAOYSA-N 0.000 description 1
WRJPJZTWQTUPQK-UHFFFAOYSA-N n-(6-aminohexyl)acetamide Chemical compound CC(=O)NCCCCCCN WRJPJZTWQTUPQK-UHFFFAOYSA-N 0.000 description 1
GYMXARDUPQTREX-UHFFFAOYSA-N n-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]acetamide Chemical compound CC(=O)NCCNCC(O)COC1=CC=CC=C1 GYMXARDUPQTREX-UHFFFAOYSA-N 0.000 description 1
RENGVVYELIHMGI-UHFFFAOYSA-N n-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]benzamide Chemical compound C=1C=CC=CC=1OCC(O)CNCCNC(=O)C1=CC=CC=C1 RENGVVYELIHMGI-UHFFFAOYSA-N 0.000 description 1
WKNWQVRIMUYOES-UHFFFAOYSA-N n-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]benzamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1OCC(O)CNCCNC(=O)C1=CC=CC=C1 WKNWQVRIMUYOES-UHFFFAOYSA-N 0.000 description 1
XSSXWVAFIYUELU-UHFFFAOYSA-N n-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]benzenesulfonamide Chemical compound C=1C=CC=CC=1OCC(O)CNCCNS(=O)(=O)C1=CC=CC=C1 XSSXWVAFIYUELU-UHFFFAOYSA-N 0.000 description 1
YPCFHXCIYKEUMI-UHFFFAOYSA-N n-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]benzenesulfonamide;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=CC=CC=1OCC(O)CNCCNS(=O)(=O)C1=CC=CC=C1 YPCFHXCIYKEUMI-UHFFFAOYSA-N 0.000 description 1
LCUIPJKTSSUGGK-UHFFFAOYSA-N n-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]butanamide Chemical compound CCCC(=O)NCCNCC(O)COC1=CC=CC=C1 LCUIPJKTSSUGGK-UHFFFAOYSA-N 0.000 description 1
SEACZQLMSXGARM-UHFFFAOYSA-N n-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl]formamide Chemical compound O=CNCCNCC(O)COC1=CC=CC=C1 SEACZQLMSXGARM-UHFFFAOYSA-N 0.000 description 1
ZIYXRUIZIGGIMZ-UHFFFAOYSA-N n-[2-[(3-chloro-2-hydroxypropyl)amino]ethyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NCCNCC(O)CCl ZIYXRUIZIGGIMZ-UHFFFAOYSA-N 0.000 description 1
AKYAPABARPZOSK-UHFFFAOYSA-N n-[2-[(3-chloro-2-hydroxypropyl)amino]ethyl]-2-methylpropanamide;oxalic acid Chemical compound OC(=O)C(O)=O.CC(C)C(=O)NCCNCC(O)CCl AKYAPABARPZOSK-UHFFFAOYSA-N 0.000 description 1
MVGQEJRHLMPMBS-UHFFFAOYSA-N n-[2-[[2-hydroxy-3-(2-methoxyphenoxy)propyl]amino]ethyl]-2-methylpropanamide Chemical compound COC1=CC=CC=C1OCC(O)CNCCNC(=O)C(C)C MVGQEJRHLMPMBS-UHFFFAOYSA-N 0.000 description 1
IFFWJAHECUQKKW-UHFFFAOYSA-N n-[2-[[2-hydroxy-3-(3-hydroxyphenoxy)propyl]amino]ethyl]benzenesulfonamide Chemical compound C=1C=CC(O)=CC=1OCC(O)CNCCNS(=O)(=O)C1=CC=CC=C1 IFFWJAHECUQKKW-UHFFFAOYSA-N 0.000 description 1
WIOAXEVPGLQULX-UHFFFAOYSA-N n-[2-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]ethyl]propanamide Chemical compound CCC(=O)NCCNCC(O)COC1=CC=CC=C1C#N WIOAXEVPGLQULX-UHFFFAOYSA-N 0.000 description 1
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
AMZORBZSQRUXNC-UHFFFAOYSA-N o-Tolyl acetate Chemical compound CC(=O)OC1=CC=CC=C1C AMZORBZSQRUXNC-UHFFFAOYSA-N 0.000 description 1
125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
230000000414 obstructive effect Effects 0.000 description 1
YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 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
150000007530 organic bases Chemical class 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
ZDYUUBIMAGBMPY-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O ZDYUUBIMAGBMPY-UHFFFAOYSA-N 0.000 description 1
150000002917 oxazolidines Chemical class 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229910052763 palladium Inorganic materials 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
210000005259 peripheral blood Anatomy 0.000 description 1
239000011886 peripheral blood Substances 0.000 description 1
239000000810 peripheral vasodilating agent Substances 0.000 description 1
229960002116 peripheral vasodilator Drugs 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
229940049953 phenylacetate Drugs 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 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
229910052697 platinum Inorganic materials 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-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
208000023504 respiratory system disease Diseases 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
229920006395 saturated elastomer Polymers 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
231100000161 signs of toxicity Toxicity 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000010454 slate Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
210000005090 tracheal smooth muscle Anatomy 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
229920002554 vinyl polymer Polymers 0.000 description 1
JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 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
- 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
- C07C275/06—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 acyclic and saturated carbon skeleton
- C07C275/14—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 acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SE7316863A 1972-12-15 1973-12-13 Forfarande for framstellning av nya (fenoxi- eller naftyloxi-)propanolamin-derivat med farmakologiska egenskaper SE408794B (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB5797072		1972-12-15
GB4347873A GB1455116A (en)	1972-12-15	1973-09-17	Pharmaceutical compositions

Publications (1)

Publication Number	Publication Date
SE408794B true SE408794B (sv)	1979-07-09

Family

ID=26265164

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7316863A SE408794B (sv)	1972-12-15	1973-12-13	Forfarande for framstellning av nya (fenoxi- eller naftyloxi-)propanolamin-derivat med farmakologiska egenskaper

Country Status (28)

Country	Link
US (2)	US3928412A (xx)
JP (1)	JPS5919090B2 (xx)
AR (2)	AR213930A1 (xx)
AT (3)	AT345791B (xx)
BE (1)	BE808666A (xx)
CA (1)	CA1031362A (xx)
CH (4)	CH605668A5 (xx)
CS (1)	CS187389B2 (xx)
DD (1)	DD113349A5 (xx)
DE (1)	DE2362568C2 (xx)
DK (1)	DK158466C (xx)
ES (1)	ES421538A1 (xx)
FI (1)	FI61027C (xx)
FR (1)	FR2210407B1 (xx)
GB (1)	GB1455116A (xx)
HK (1)	HK24480A (xx)
HU (1)	HU169087B (xx)
IE (1)	IE38602B1 (xx)
IL (1)	IL43795A (xx)
IN (1)	IN139418B (xx)
KE (1)	KE3030A (xx)
LU (1)	LU68997A1 (xx)
MY (1)	MY8100035A (xx)
NL (1)	NL179203C (xx)
NO (1)	NO138335C (xx)
SE (1)	SE408794B (xx)
SU (2)	SU576917A3 (xx)
YU (2)	YU40097B (xx)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4038313A (en) *	1970-01-08	1977-07-26	Ciba-Geigy Corporation	Cycloalkylureido phenoxy propanolamines
US4167581A (en) *	1972-12-15	1979-09-11	Imperial Chemical Industries Limited	Alkanolamine derivatives and pharmaceutical compositions and uses thereof
US4171374A (en) *	1972-12-15	1979-10-16	Imperial Chemical Industries Limited	Alkanolamine derivatives
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
US4041074A (en) *	1973-07-19	1977-08-09	Imperial Chemical Industries Limited	1-Hydroxyaryl-2-amidoalkylaminoethanol derivatives
GB1573359A (en) *	1977-12-20	1980-08-20	Ici Ltd	Alkanolamine derivatives
GB1509527A (en) *	1974-06-05	1978-05-04	Ici Ltd	1-(aryl-or heteroaryl)oxy-3-(substituted-amino)propan-2-ol derivatives processes for their manufacture and pharmaceutical compositions containing them
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
US4162331A (en) *	1975-06-17	1979-07-24	Nippon Shinyaku Co., Ltd.	Substituted N-(carboxymethyl)-3-aminopropan-2-ol derivatives
GB1540463A (en) *	1976-10-07	1979-02-14	Ici Ltd	Alkanolamine derivatives
US4172150A (en) *	1977-05-23	1979-10-23	Imperial Chemical Industries Limited	Cardiac stimulants
IE47053B1 (en) *	1977-05-23	1983-12-14	Ici Ltd	Cardiac stimulants
US4219561A (en) *	1977-09-22	1980-08-26	Imperial Chemical Industries Limited	Alkanolamine derivatives
US4239700A (en) *	1978-10-10	1980-12-16	Texaco Development Corp.	Isatoic anhydride derivatives and use as chain-extenders
US4301300A (en) *	1979-09-06	1981-11-17	Hoffmann-La Roche Inc.	Sulfonamide intermediates for adrenergic blocking agents
US4281189A (en) *	1979-09-06	1981-07-28	Hoffmann-La Roche Inc.	Sulfonamide intermediates for adrenergic blocking agents
FR2477537A1 (fr) *	1980-03-07	1981-09-11	Francaise Sucrerie	Nouvelles guanidines acylees, urees et urees substituees, leur procede de fabrication et leur application en tant que medicaments
FI76551C (fi)	1980-11-06	1988-11-10	Sandoz Ag	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3-aminopropoxifenylderivat.
ATE19510T1 (de) *	1981-12-17	1986-05-15	Haessle Ab	Para-substituierte 3-phenoxy-1carbonylaminoalkylaminopropan-2-ole mit blockierenden wirkungen bei betarezeptoren.
US5238962A (en) *	1983-03-03	1993-08-24	Hoffmann-La Roche Inc.	Benzamide derivatives
CH653670A5 (de) *	1983-03-03	1986-01-15	Hoffmann La Roche	Benzamid-derivate.
US4593039A (en) *	1984-04-02	1986-06-03	Merck & Co., Inc.	1-aryloxy-3-(substituted aminoalkylamino)-2-propanols
DE3427309A1 (de) *	1984-07-25	1986-01-30	Boehringer Ingelheim KG, 6507 Ingelheim	Neue 1-aryloxypropanolamine, verfahren zu ihrer herstellung und ihre verwendung
DE3512627A1 (de) *	1985-04-06	1986-10-09	Boehringer Mannheim Gmbh, 6800 Mannheim	Amino-propanol-derivate, verfahren zu deren herstellung, verwendung derselben und diese enthaltende arzneimittel
AU601948B2 (en) *	1985-05-14	1990-09-27	William John Louis	3-aminopropyloxyphenyl derivatives their preparation and pharmaceutical compositions containing them
EP0207036A1 (en) *	1985-06-20	1986-12-30	Aktiebolaget Hässle	New para-substituted 3-phenoxy-1-piperidinecarbonylaminoalkylamino-propanol-2-s having beta receptor blocking properties.
GB8607313D0 (en) *	1986-03-25	1986-04-30	Ici Plc	Pharmaceutical compositions
GB8607312D0 (en) *	1986-03-25	1986-04-30	Ici Plc	Therapeutic agents
DE3880628T2 (de) *	1987-11-13	1993-08-05	Glaxo Group Ltd	Phenethanolamin-derivate.
JP2004137284A (ja) *	1997-06-17	2004-05-13	Kaken Pharmaceut Co Ltd	２−スルファモイル安息香酸誘導体
GB0417802D0 (en) *	2004-08-10	2004-09-15	Novartis Ag	Organic compounds
CN106977426A (zh) *	2017-05-27	2017-07-25	哈尔滨师范大学	一种腰果酚苯基脲及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3459782A (en) *	1963-08-26	1969-08-05	Boehringer Sohn Ingelheim	1-substituted phenoxy-2-hydroxy-3-isopropylamino-propanes
GB1199037A (en) *	1967-09-27	1970-07-15	Ici Ltd	Alkanolamine Derivatives
GB1285038A (en) *	1969-02-21	1972-08-09	Ici Ltd	Alkanolamine derivatives
BE754604A (fr) *	1969-08-08	1971-02-08	Boehringer Sohn Ingelheim	Le 1-(2-nitrilophenoxy)-2-hydroxy-3-ethyl-aminopropane et ses sels

1973
- 1973-09-17 GB GB4347873A patent/GB1455116A/en not_active Expired
- 1973-12-03 IE IE2183/73A patent/IE38602B1/xx unknown
- 1973-12-04 US US421669A patent/US3928412A/en not_active Expired - Lifetime
- 1973-12-04 CA CA187,289A patent/CA1031362A/en not_active Expired
- 1973-12-06 IN IN2664/CAL/73A patent/IN139418B/en unknown
- 1973-12-10 IL IL43795A patent/IL43795A/xx unknown
- 1973-12-11 FI FI3789/73A patent/FI61027C/fi active
- 1973-12-13 SE SE7316863A patent/SE408794B/sv unknown
- 1973-12-13 LU LU68997A patent/LU68997A1/xx unknown
- 1973-12-13 NL NLAANVRAGE7317096,A patent/NL179203C/xx not_active IP Right Cessation
- 1973-12-14 CH CH1340277A patent/CH605668A5/xx not_active IP Right Cessation
- 1973-12-14 DK DK681673A patent/DK158466C/da not_active IP Right Cessation
- 1973-12-14 CH CH1759473A patent/CH605666A5/xx not_active IP Right Cessation
- 1973-12-14 HU HUIE600A patent/HU169087B/hu unknown
- 1973-12-14 CH CH1340177A patent/CH605667A5/xx not_active IP Right Cessation
- 1973-12-14 YU YU3246/73A patent/YU40097B/xx unknown
- 1973-12-14 AR AR251531A patent/AR213930A1/es active
- 1973-12-14 FR FR7344780A patent/FR2210407B1/fr not_active Expired
- 1973-12-14 BE BE138894A patent/BE808666A/xx not_active IP Right Cessation
- 1973-12-14 SU SU7301981054A patent/SU576917A3/ru active
- 1973-12-14 NO NO4794/73A patent/NO138335C/no unknown
- 1973-12-14 CH CH1340377A patent/CH611876A5/xx not_active IP Right Cessation
- 1973-12-14 DD DD175410A patent/DD113349A5/xx unknown
- 1973-12-15 ES ES421538A patent/ES421538A1/es not_active Expired
- 1973-12-15 JP JP48141162A patent/JPS5919090B2/ja not_active Expired
- 1973-12-17 DE DE2362568A patent/DE2362568C2/de not_active Expired
- 1973-12-17 AT AT581577A patent/AT345791B/de not_active IP Right Cessation
- 1973-12-17 CS CS738727A patent/CS187389B2/cs unknown
1975
- 1975-08-26 US US05/607,995 patent/US4010189A/en not_active Expired - Lifetime
1976
- 1976-04-12 AT AT266376A patent/AT344144B/de not_active IP Right Cessation
- 1976-04-21 AR AR262359A patent/AR214288A1/es active
1977
- 1977-07-26 SU SU772504510A patent/SU695555A3/ru active
- 1977-07-29 AT AT566077A patent/AT351557B/de not_active IP Right Cessation
1980
- 1980-03-03 KE KE3030A patent/KE3030A/xx unknown
- 1980-05-08 HK HK244/80A patent/HK24480A/xx unknown
- 1980-11-03 YU YU2806/80A patent/YU42539B/xx unknown
1981
- 1981-12-30 MY MY35/81A patent/MY8100035A/xx unknown

Also Published As

Publication number	Publication date
YU324673A (en)	1982-02-28
CA1031362A (en)	1978-05-16
AT351557B (de)	1979-08-10
YU280680A (en)	1983-09-30
DD113349A5 (xx)	1975-06-05
CH611876A5 (en)	1979-06-29
NL179203B (nl)	1986-03-03
DE2362568A1 (de)	1974-06-20
NO138335B (no)	1978-05-08
HK24480A (en)	1980-05-16
YU42539B (en)	1988-10-31
ES421538A1 (es)	1976-07-16
CS187389B2 (en)	1979-01-31
FI61027C (fi)	1982-05-10
ATA566077A (de)	1979-01-15
IN139418B (xx)	1976-06-19
FR2210407B1 (xx)	1978-01-13
IE38602L (en)	1974-06-15
AT344144B (de)	1978-07-10
YU40097B (en)	1985-08-31
US3928412A (en)	1975-12-23
DE2362568C2 (de)	1983-11-03
IL43795A (en)	1978-03-10
NL7317096A (xx)	1974-06-18
ATA266376A (de)	1977-11-15
NO138335C (no)	1978-08-16
AT345791B (de)	1978-10-10
CH605666A5 (xx)	1978-10-13
SU576917A3 (ru)	1977-10-15
US4010189A (en)	1977-03-01
DK158466C (da)	1990-10-15
GB1455116A (en)	1976-11-10
AR213930A1 (es)	1979-04-11
IL43795A0 (en)	1974-03-14
JPS5919090B2 (ja)	1984-05-02
LU68997A1 (xx)	1974-02-22
AR214288A1 (es)	1979-05-31
CH605667A5 (xx)	1978-10-13
IE38602B1 (en)	1978-04-26
FI61027B (fi)	1982-01-29
CH605668A5 (xx)	1978-10-13
MY8100035A (en)	1981-12-31
SU695555A3 (ru)	1979-10-30
BE808666A (fr)	1974-06-14
JPS4994638A (xx)	1974-09-09
NL179203C (nl)	1986-08-01
KE3030A (en)	1980-03-14
FR2210407A1 (xx)	1974-07-12
HU169087B (xx)	1976-09-28
DK158466B (da)	1990-05-21

Publication	Publication Date	Title
SE408794B (sv)	1979-07-09	Forfarande for framstellning av nya (fenoxi- eller naftyloxi-)propanolamin-derivat med farmakologiska egenskaper
PT95148A (pt)	1991-05-22	Processo para a preparacao de inibidores do enzima acilcoenzima a:colesterol aciltransferase (acat) e de composicoes farmaceuticas que os contem
CZ252090A3 (en)	1996-06-12	Process for preparing phenylalkylene n-substituted alpha-aminocarboxamides
US3933911A (en)	1976-01-20	1-Aryl-2-amidoalkylaminoethanol derivatives
EP0373998B1 (fr)	1993-08-11	Ethers d'oxime de propénone, procédé pour leur préparation et compositions pharmaceutiques les contenant
CA2469967A1 (en)	2003-07-10	Urea derivatives as vr1- antagonists
EP1465623A1 (en)	2004-10-13	Urea derivatives
US4083992A (en)	1978-04-11	Alkanolamine derivatives
EP1689380A2 (en)	2006-08-16	Method for treating adamts-5-associated disease
JP2601008B2 (ja)	1997-04-16	ナフチルオキサゾリドン誘導体、その製法及びその合成中間体
JP4335131B2 (ja)	2009-09-30	ヒドロキシテトラヒドロ−ナフタレニル尿素誘導体
NO128653B (xx)	1973-12-27
US20050197343A1 (en)	2005-09-08	Utilization of heteroarene carboxamide as dopamine-d3 ligands for the treatment of cns diseases
RU2345061C2 (ru)	2009-01-27	Производные (2-аминофенил)-амида ариленкарбоновой кислоты как фармацевтические препараты
US3959369A (en)	1976-05-25	Alkanolamine derivatives
US4131685A (en)	1978-12-26	Pharmaceutical compositions and uses of alkanolamine derivatives
FR2498596A1 (fr)	1982-07-30	Nouvelles phenylalcoylamines, leur preparation et leur utilisation en tant que medicaments
ES2322451T3 (es)	2009-06-22	Inhibidores de la peptido deformilasa.
US4034112A (en)	1977-07-05	Ethanolamine derivatives having β-adrenergic blocking activity
US4167581A (en)	1979-09-11	Alkanolamine derivatives and pharmaceutical compositions and uses thereof
CA2429267C (fr)	2010-09-28	Cyclohexyl(alkyl)-propanolamines, leur preparation et compositions pharmaceutiques en contenant
US3957870A (en)	1976-05-18	Organic compounds
JP2003192659A (ja)	2003-07-09	フェニル尿素誘導体
US4041074A (en)	1977-08-09	1-Hydroxyaryl-2-amidoalkylaminoethanol derivatives
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