PL96221B1 - Sposob wytwarzania nowych aminofenyloetanoloamin - Google Patents

Sposob wytwarzania nowych aminofenyloetanoloamin Download PDF

Info

Publication number: PL96221B1
Authority: PL; Poland
Prior art keywords: amino; hydrochloride; melting point; chloro; prepared
Prior art date: 1972-12-18

Application number

PL16739973A

Other languages

English (en)

Polish (pl)

Original Assignee

Thomae Karl (Dr) Gmbh

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.)

1972-12-18

Filing date

1973-12-17

Publication date

1977-12-31

1972-12-18 Priority claimed from DE2261914A external-priority patent/DE2261914C3/de

1973-09-08 Priority claimed from DE19732345442 external-priority patent/DE2345442C2/de

1973-10-12 Priority claimed from DE19732351281 external-priority patent/DE2351281C3/de

1973-12-17 Application filed by Thomae Karl (Dr) Gmbh filed Critical Thomae Karl (Dr) Gmbh

1977-12-31 Publication of PL96221B1 publication Critical patent/PL96221B1/pl

Links

IKNLHBCWJCVJDZ-UHFFFAOYSA-N 1,2-diamino-1-phenylethanol Chemical compound NCC(N)(O)C1=CC=CC=C1 IKNLHBCWJCVJDZ-UHFFFAOYSA-N 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title description 2
-1 aluminum isopropanol Chemical compound 0.000 claims description 39
150000001875 compounds Chemical class 0.000 claims description 37
238000000034 method Methods 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
150000007522 mineralic acids Chemical class 0.000 claims description 8
150000007524 organic acids Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
238000009835 boiling Methods 0.000 claims description 6
229910052987 metal hydride Inorganic materials 0.000 claims description 6
150000004681 metal hydrides Chemical class 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 5
238000002425 crystallisation Methods 0.000 claims description 5
230000008025 crystallization Effects 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
150000002825 nitriles Chemical class 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000002560 nitrile group Chemical group 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 4
239000011975 tartaric acid Substances 0.000 claims description 4
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
235000002906 tartaric acid Nutrition 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
238000004440 column chromatography Methods 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims 3
229960001367 tartaric acid Drugs 0.000 claims 2
235000011437 Amygdalus communis Nutrition 0.000 claims 1
241000220304 Prunus dulcis Species 0.000 claims 1
235000020224 almond Nutrition 0.000 claims 1
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 205
238000002844 melting Methods 0.000 description 195
230000008018 melting Effects 0.000 description 195
229910000033 sodium borohydride Inorganic materials 0.000 description 169
239000012279 sodium borohydride Substances 0.000 description 169
238000000354 decomposition reaction Methods 0.000 description 122
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 18
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 14
229910052708 sodium Inorganic materials 0.000 description 14
239000011734 sodium Substances 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
238000003776 cleavage reaction Methods 0.000 description 8
230000007017 scission Effects 0.000 description 8
239000000126 substance Substances 0.000 description 8
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000006309 butyl amino group Chemical group 0.000 description 6
239000003921 oil Substances 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
BXMDCYQJTCWVGG-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-(dimethylamino)-1-hydroxyethyl]benzonitrile;hydrochloride Chemical compound Cl.CN(C)CC(O)C1=CC(Br)=C(N)C(C#N)=C1 BXMDCYQJTCWVGG-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
230000000202 analgesic effect Effects 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
NTBIYBAYFBNTCD-KBPBESRZSA-N dibenzoyl (2s,3s)-2,3-dihydroxybutanedioate Chemical compound O=C([C@@H](O)[C@H](O)C(=O)OC(=O)C=1C=CC=CC=1)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-KBPBESRZSA-N 0.000 description 4
238000001640 fractional crystallisation Methods 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
206010006482 Bronchospasm Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
KHRNKQIDXYINAU-UHFFFAOYSA-N [B+3].[O-2].[Na+].[O-2] Chemical compound [B+3].[O-2].[Na+].[O-2] KHRNKQIDXYINAU-UHFFFAOYSA-N 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
239000007864 aqueous solution 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
230000000903 blocking effect Effects 0.000 description 3
230000001813 broncholytic effect Effects 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002168 ethanoic acid esters Chemical class 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
RJJNELFJIFRHRT-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(cyclobutylamino)ethanol Chemical compound C1=C(Br)C(N)=C(F)C=C1C(O)CNC1CCC1 RJJNELFJIFRHRT-UHFFFAOYSA-N 0.000 description 2
RSOCHJOFBUPVHJ-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(cyclopropylamino)ethanone Chemical compound C1=C(Br)C(N)=C(F)C=C1C(=O)CNC1CC1 RSOCHJOFBUPVHJ-UHFFFAOYSA-N 0.000 description 2
TUFXYMINQOCVSO-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(ethylamino)ethanol Chemical compound C(C)NCC(O)C1=CC(=C(C(=C1)F)N)Br TUFXYMINQOCVSO-UHFFFAOYSA-N 0.000 description 2
AEVYLFOGMAQETO-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(ethylamino)ethanone hydrochloride Chemical compound Cl.C(C)NCC(=O)C1=CC(=C(C(=C1)F)N)Br AEVYLFOGMAQETO-UHFFFAOYSA-N 0.000 description 2
PFMPSTXJMGJXME-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(propan-2-ylamino)ethanone;hydrochloride Chemical compound Cl.CC(C)NCC(=O)C1=CC(F)=C(N)C(Br)=C1 PFMPSTXJMGJXME-UHFFFAOYSA-N 0.000 description 2
LSLBOXLMMCSNAL-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC(F)=C(N)C(Br)=C1 LSLBOXLMMCSNAL-UHFFFAOYSA-N 0.000 description 2
WICLOGHQCOZCCO-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-fluorophenyl)-2-(2-methylbutan-2-ylamino)ethanol Chemical compound CCC(C)(C)NCC(O)C1=CC(F)=C(N)C(Cl)=C1 WICLOGHQCOZCCO-UHFFFAOYSA-N 0.000 description 2
KTSLWISKSKLWLB-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-fluorophenyl)-2-(diethylamino)ethanol Chemical compound NC1=C(C=C(C=C1F)C(CN(CC)CC)O)Cl KTSLWISKSKLWLB-UHFFFAOYSA-N 0.000 description 2
HLBAWJHCKHANLA-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-fluorophenyl)-2-(propan-2-ylamino)ethanone;hydrochloride Chemical compound Cl.CC(C)NCC(=O)C1=CC(F)=C(N)C(Cl)=C1 HLBAWJHCKHANLA-UHFFFAOYSA-N 0.000 description 2
SKDLWNWMKMZBBJ-UHFFFAOYSA-N 1-(4-amino-3-fluoro-5-iodophenyl)-2-(cyclobutylamino)ethanol Chemical compound C1=C(I)C(N)=C(F)C=C1C(O)CNC1CCC1 SKDLWNWMKMZBBJ-UHFFFAOYSA-N 0.000 description 2
ZKPQFJSREXSZDP-UHFFFAOYSA-N 1-(4-amino-3-fluoro-5-iodophenyl)-2-(cyclobutylamino)ethanone Chemical compound C1=C(I)C(N)=C(F)C=C1C(=O)CNC1CCC1 ZKPQFJSREXSZDP-UHFFFAOYSA-N 0.000 description 2
BCPNBFXTSJDVOZ-UHFFFAOYSA-N 1-(4-amino-3-fluoro-5-iodophenyl)-2-(cyclopropylamino)ethanone Chemical compound C1=C(I)C(N)=C(F)C=C1C(=O)CNC1CC1 BCPNBFXTSJDVOZ-UHFFFAOYSA-N 0.000 description 2
UEFLEOWVKMBYCH-UHFFFAOYSA-N 1-(4-amino-3-fluoro-5-iodophenyl)-2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCC(O)C1=CC(F)=C(N)C(I)=C1 UEFLEOWVKMBYCH-UHFFFAOYSA-N 0.000 description 2
LGDKGAMWEGSVKG-UHFFFAOYSA-N 1-(4-amino-3-fluoro-5-iodophenyl)-2-(propan-2-ylamino)ethanone Chemical compound CC(C)NCC(=O)C1=CC(F)=C(N)C(I)=C1 LGDKGAMWEGSVKG-UHFFFAOYSA-N 0.000 description 2
FIZFDYUAZUOPFK-UHFFFAOYSA-N 1-(4-amino-3-fluoro-5-iodophenyl)-2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC(F)=C(N)C(I)=C1 FIZFDYUAZUOPFK-UHFFFAOYSA-N 0.000 description 2
VQPYFOBTSRYKGM-UHFFFAOYSA-N 1-(4-amino-3-fluoro-5-iodophenyl)-2-(tert-butylamino)ethanone Chemical compound CC(C)(C)NCC(=O)C1=CC(F)=C(N)C(I)=C1 VQPYFOBTSRYKGM-UHFFFAOYSA-N 0.000 description 2
NYIYGBYAGXEKGR-UHFFFAOYSA-N 1-[4-amino-3-(hydroxymethyl)phenyl]-2-(dimethylamino)ethanol Chemical compound NC1=C(C=C(C=C1)C(CN(C)C)O)CO NYIYGBYAGXEKGR-UHFFFAOYSA-N 0.000 description 2
QOLXYSJLOIKEOT-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-(trifluoromethyl)phenyl]-2-(cyclobutylamino)ethanol Chemical compound C1=C(C(F)(F)F)C(N)=C(Br)C=C1C(O)CNC1CCC1 QOLXYSJLOIKEOT-UHFFFAOYSA-N 0.000 description 2
OQKQCZKWDZTXPQ-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-(trifluoromethyl)phenyl]-2-(cyclopropylamino)ethanol Chemical compound C1=C(C(F)(F)F)C(N)=C(Br)C=C1C(O)CNC1CC1 OQKQCZKWDZTXPQ-UHFFFAOYSA-N 0.000 description 2
HIEUUDCCSRBCGQ-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-(trifluoromethyl)phenyl]-2-(cyclopropylamino)ethanone;hydrochloride Chemical compound Cl.C1=C(C(F)(F)F)C(N)=C(Br)C=C1C(=O)CNC1CC1 HIEUUDCCSRBCGQ-UHFFFAOYSA-N 0.000 description 2
AGCWKEHGEJENPO-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-(trifluoromethyl)phenyl]-2-(cyclopropylmethylamino)ethanol Chemical compound NC1=C(C=C(C=C1C(F)(F)F)C(CNCC1CC1)O)Br AGCWKEHGEJENPO-UHFFFAOYSA-N 0.000 description 2
XZPHJLPEVYASII-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-(trifluoromethyl)phenyl]-2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCC(O)C1=CC(Br)=C(N)C(C(F)(F)F)=C1 XZPHJLPEVYASII-UHFFFAOYSA-N 0.000 description 2
PXWNONAPYQQPBJ-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-(trifluoromethyl)phenyl]-2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC(Br)=C(N)C(C(F)(F)F)=C1 PXWNONAPYQQPBJ-UHFFFAOYSA-N 0.000 description 2
QDSKWSISSMEBEV-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(cyclobutylamino)ethanol Chemical compound C1=C(C(F)(F)F)C(N)=C(Cl)C=C1C(O)CNC1CCC1 QDSKWSISSMEBEV-UHFFFAOYSA-N 0.000 description 2
KBSMVHNUJZFZEV-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(cyclohexylamino)ethanol Chemical compound NC1=C(C=C(C=C1C(F)(F)F)C(CNC1CCCCC1)O)Cl KBSMVHNUJZFZEV-UHFFFAOYSA-N 0.000 description 2
VXRYDMSNIVHIJP-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(cyclohexylamino)ethanone Chemical compound NC1=C(C=C(C=C1C(F)(F)F)C(CNC1CCCCC1)=O)Cl VXRYDMSNIVHIJP-UHFFFAOYSA-N 0.000 description 2
QJSNTOHSUPVKBM-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(cyclopentylamino)ethanol Chemical compound C1=C(C(F)(F)F)C(N)=C(Cl)C=C1C(O)CNC1CCCC1 QJSNTOHSUPVKBM-UHFFFAOYSA-N 0.000 description 2
UKLLTQFWZIPQEC-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(cyclopentylamino)ethanone Chemical compound C1=C(C(F)(F)F)C(N)=C(Cl)C=C1C(=O)CNC1CCCC1 UKLLTQFWZIPQEC-UHFFFAOYSA-N 0.000 description 2
MKPTZDULDJNCMK-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(cyclopropylamino)ethanol Chemical compound C1=C(C(F)(F)F)C(N)=C(Cl)C=C1C(O)CNC1CC1 MKPTZDULDJNCMK-UHFFFAOYSA-N 0.000 description 2
ULSYKVBOZDNFSC-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(cyclopropylamino)ethanone Chemical compound C1=C(C(F)(F)F)C(N)=C(Cl)C=C1C(=O)CNC1CC1 ULSYKVBOZDNFSC-UHFFFAOYSA-N 0.000 description 2
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XDSJAUYKXOGZNU-UHFFFAOYSA-N 2-amino-3-chloro-5-[2-(propan-2-ylamino)acetyl]benzonitrile Chemical compound CC(C)NCC(=O)C1=CC(Cl)=C(N)C(C#N)=C1 XDSJAUYKXOGZNU-UHFFFAOYSA-N 0.000 description 1
VJJUEJQJZWTZKS-UHFFFAOYSA-N 2-amino-3-chloro-5-[2-(propylamino)acetyl]benzonitrile Chemical compound CCCNCC(=O)C1=CC(Cl)=C(N)C(C#N)=C1 VJJUEJQJZWTZKS-UHFFFAOYSA-N 0.000 description 1
NESCJTFKQSIWRR-UHFFFAOYSA-N 2-amino-5-[1-hydroxy-2-(2-methylbutan-2-ylamino)ethyl]benzonitrile Chemical compound CCC(C)(C)NCC(O)C1=CC=C(N)C(C#N)=C1 NESCJTFKQSIWRR-UHFFFAOYSA-N 0.000 description 1
PTISWRLNODYSQH-UHFFFAOYSA-N 2-amino-5-[2-(cyclobutylamino)-1-hydroxyethyl]benzene-1,3-dicarbonitrile Chemical compound C1=C(C#N)C(N)=C(C#N)C=C1C(O)CNC1CCC1 PTISWRLNODYSQH-UHFFFAOYSA-N 0.000 description 1
HDYIOMSKGZXJJX-UHFFFAOYSA-N 2-amino-5-[2-(cyclobutylamino)-1-hydroxyethyl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C(O)CNC1CCC1 HDYIOMSKGZXJJX-UHFFFAOYSA-N 0.000 description 1
UDBGUGPSPQZHOU-UHFFFAOYSA-N 2-amino-5-[2-(cyclobutylamino)acetyl]benzene-1,3-dicarbonitrile Chemical compound C1=C(C#N)C(N)=C(C#N)C=C1C(=O)CNC1CCC1 UDBGUGPSPQZHOU-UHFFFAOYSA-N 0.000 description 1
VGZFWIKTTGXCKJ-UHFFFAOYSA-N 2-amino-5-[2-(cyclopentylamino)-1-hydroxyethyl]-3-fluorobenzonitrile Chemical compound C1=C(C#N)C(N)=C(F)C=C1C(O)CNC1CCCC1 VGZFWIKTTGXCKJ-UHFFFAOYSA-N 0.000 description 1
MMODRTUHSAJYFZ-UHFFFAOYSA-N 2-amino-5-[2-(cyclopentylamino)-1-hydroxyethyl]benzene-1,3-dicarbonitrile Chemical compound C1=C(C#N)C(N)=C(C#N)C=C1C(O)CNC1CCCC1 MMODRTUHSAJYFZ-UHFFFAOYSA-N 0.000 description 1
WIVXXMZVTOUTAE-UHFFFAOYSA-N 2-amino-5-[2-(cyclopentylamino)acetyl]-3-fluorobenzonitrile Chemical compound C1=C(C#N)C(N)=C(F)C=C1C(=O)CNC1CCCC1 WIVXXMZVTOUTAE-UHFFFAOYSA-N 0.000 description 1
ZRJDUTHQKARIHD-UHFFFAOYSA-N 2-amino-5-[2-(cyclopentylamino)acetyl]benzene-1,3-dicarbonitrile Chemical compound C1=C(C#N)C(N)=C(C#N)C=C1C(=O)CNC1CCCC1 ZRJDUTHQKARIHD-UHFFFAOYSA-N 0.000 description 1
UBFBSWCLJJRFMB-UHFFFAOYSA-N 2-amino-5-[2-(ethylamino)-1-hydroxyethyl]-3-fluorobenzonitrile Chemical compound CCNCC(O)C1=CC(F)=C(N)C(C#N)=C1 UBFBSWCLJJRFMB-UHFFFAOYSA-N 0.000 description 1
ARHFPAYWUREQGK-UHFFFAOYSA-N 2-amino-5-[2-(propan-2-ylamino)acetyl]benzene-1,3-dicarbonitrile Chemical compound CC(C)NCC(=O)C1=CC(C#N)=C(N)C(C#N)=C1 ARHFPAYWUREQGK-UHFFFAOYSA-N 0.000 description 1
CGCHJJMCSJZEGH-UHFFFAOYSA-N 2-amino-5-[2-(tert-butylamino)-1-hydroxyethyl]-3-chlorobenzonitrile Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(C#N)=C1 CGCHJJMCSJZEGH-UHFFFAOYSA-N 0.000 description 1
XNINHKMSAKSUNU-UHFFFAOYSA-N 2-amino-5-[2-(tert-butylamino)-1-hydroxyethyl]-3-fluorobenzonitrile Chemical compound CC(C)(C)NCC(O)C1=CC(F)=C(N)C(C#N)=C1 XNINHKMSAKSUNU-UHFFFAOYSA-N 0.000 description 1
YYVOMLJFTZMOJM-UHFFFAOYSA-N 2-amino-5-[2-[tert-butyl(hydroxy)amino]-1-hydroxyethyl]-3-chlorobenzonitrile;hydrochloride Chemical group Cl.CC(C)(C)N(O)CC(O)C1=CC(Cl)=C(N)C(C#N)=C1 YYVOMLJFTZMOJM-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
208000014181 Bronchial disease Diseases 0.000 description 1
BLHYDPYCJCZEFB-UHFFFAOYSA-N C(C)C=1C=C(C=C(C1N)Br)C(CN(CC)CC)=O Chemical compound C(C)C=1C=C(C=C(C1N)Br)C(CN(CC)CC)=O BLHYDPYCJCZEFB-UHFFFAOYSA-N 0.000 description 1
OQODPURIUMDJCP-UHFFFAOYSA-N CCN(CC)CC(C1=CC(=C(C(=C1)C)N)Cl)O Chemical compound CCN(CC)CC(C1=CC(=C(C(=C1)C)N)Cl)O OQODPURIUMDJCP-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
OGYVXNCBFQVWIM-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1C(F)(F)F)C(CN(CC)CC)=O)Cl Chemical compound Cl.NC1=C(C=C(C=C1C(F)(F)F)C(CN(CC)CC)=O)Cl OGYVXNCBFQVWIM-UHFFFAOYSA-N 0.000 description 1
NRWVRZUOKYRRJK-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1F)C(CN(CC)CC)=O)Cl Chemical compound Cl.NC1=C(C=C(C=C1F)C(CN(CC)CC)=O)Cl NRWVRZUOKYRRJK-UHFFFAOYSA-N 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
MMCDXJOMPMIKGP-UHFFFAOYSA-N Mabuterol hydrochloride Chemical compound [Cl-].CC(C)(C)[NH2+]CC(O)C1=CC(Cl)=C(N)C(C(F)(F)F)=C1 MMCDXJOMPMIKGP-UHFFFAOYSA-N 0.000 description 1
102000010909 Monoamine Oxidase Human genes 0.000 description 1
108010062431 Monoamine oxidase Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
PRBROPYNMRZXBE-UHFFFAOYSA-J [Cl-].[Na+].[B+3].[Cl-].[Cl-].[Cl-] Chemical compound [Cl-].[Na+].[B+3].[Cl-].[Cl-].[Cl-] PRBROPYNMRZXBE-UHFFFAOYSA-J 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000000556 agonist Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000003275 alpha amino acid group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000013213 extrapolation Methods 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000000075 primary alcohol group Chemical group 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms

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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

PL16739973A 1972-12-18 1973-12-17 Sposob wytwarzania nowych aminofenyloetanoloamin PL96221B1 (pl)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE2261914A DE2261914C3 (de)	1972-12-18	1972-12-18	Amino-phenyl-äthanolamine und deren Säureadditionssalze, Verfahren zu deren Herstellung und Arzneimittel
DE19732345442 DE2345442C2 (de)	1973-09-08	1973-09-08	d- und l-Phenyläthanolamine und deren Salze, Herstellungsverfahren und Arzneimittel auf deren Basis
DE19732351281 DE2351281C3 (de)	1973-10-12	1973-10-12	Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung

Publications (1)

Publication Number	Publication Date
PL96221B1 true PL96221B1 (pl)	1977-12-31

Family

ID=27184904

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
PL16739973A PL96221B1 (pl)	1972-12-18	1973-12-17	Sposob wytwarzania nowych aminofenyloetanoloamin
PL18240673A PL96538B1 (pl)	1972-12-18	1973-12-17	Sposob wytwarzania nowych aminofenyloetanoloamin
PL18241073A PL96535B1 (pl)	1972-12-18	1973-12-17	Sposob wytwarzania nowych aminofenyloetanoloamin

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
PL18240673A PL96538B1 (pl)	1972-12-18	1973-12-17	Sposob wytwarzania nowych aminofenyloetanoloamin
PL18241073A PL96535B1 (pl)	1972-12-18	1973-12-17	Sposob wytwarzania nowych aminofenyloetanoloamin

Country Status (5)

Country	Link
AT (1)	AT333251B (de)
CH (2)	CH605623A5 (de)
ES (4)	ES421350A1 (de)
PH (2)	PH20591A (de)
PL (3)	PL96221B1 (de)

1973
- 1973-12-10 AT AT1028573A patent/AT333251B/de not_active IP Right Cessation
- 1973-12-11 ES ES421350A patent/ES421350A1/es not_active Expired
- 1973-12-14 CH CH1178877A patent/CH605623A5/de not_active IP Right Cessation
- 1973-12-14 CH CH1179077A patent/CH605656A5/xx not_active IP Right Cessation
- 1973-12-17 PL PL16739973A patent/PL96221B1/pl unknown
- 1973-12-17 PL PL18240673A patent/PL96538B1/pl unknown
- 1973-12-17 PL PL18241073A patent/PL96535B1/pl unknown
- 1973-12-18 PH PH15328A patent/PH20591A/en unknown
1974
- 1974-04-30 ES ES425791A patent/ES425791A1/es not_active Expired
- 1974-04-30 ES ES425793A patent/ES425793A1/es not_active Expired
- 1974-04-30 ES ES425792A patent/ES425792A1/es not_active Expired
1982
- 1982-03-28 PH PH27074A patent/PH19317A/en unknown

Also Published As

Publication number	Publication date
ES425793A1 (es)	1977-07-01
ES421350A1 (es)	1976-12-01
PH20591A (en)	1987-02-20
ES425791A1 (es)	1976-06-16
PL96538B1 (pl)	1977-12-31
CH605656A5 (de)	1978-10-13
PH19317A (en)	1986-03-18
CH605623A5 (en)	1978-10-13
ES425792A1 (es)	1976-06-16
ATA1028573A (de)	1976-03-15
PL96535B1 (pl)	1977-12-31
AT333251B (de)	1976-11-10

Publication	Publication Date	Title
NO126014B (de)	1972-12-11
PL97194B1 (pl)	1978-02-28	Sposob wytwarzania nowych aminofenyloetanoloamin
US3954872A (en)	1976-05-04	1-(2',6'-Dimethyl-phenoxy)-2-amino-alkanes and salts thereof
US2689248A (en)	1954-09-14	Tertiary-aminoalkyl 4-amino-2-alkoxybenzoates and their synth esis
CS197317B2 (en)	1980-04-30	Method of producing new 4-acylaminophenyl-ethanol-amines
PL96888B1 (pl)	1978-01-31	Sposob wytwarzania nowych benzyloamin
IE52007B1 (en)	1987-05-13	Chemical compounds
US4338330A (en)	1982-07-06	Benzimidazole derivatives, their use, and compositions containing these derivatives
JPS62252766A (ja)	1987-11-04	新規の２−（ヒドロキシ−フエニル）−インド−ルの製造法
EP0171037A2 (de)	1986-02-12	3-Carbonyl-1-Aminoalkyl-1H-Indole, verwendbar als Analgetika und ihre Herstellung
US4073942A (en)	1978-02-14	Halo-substituted hydroxybenzyl-amines as secretolytic agents
SK16896A3 (en)	1996-10-02	1-£2-(substituted vinyl)\|-3,4-dihydro-5h-2,3-benzodiazepine derivatives
US4182895A (en)	1980-01-08	1-Amino-lower-alkyl-3,4-diphenyl-1H-pyrazoles
NO169835B (no)	1992-05-04	Analogifremgangsmaate for fremstilling av terapeutisk aktive katecholkarboksylderivater
US3627763A (en)	1971-12-14	Substituted 2-benzyl-benzofuran derivatives
JPS6047255B2 (ja)	1985-10-21	２−アミノ−５−スルフアモイル−安息香酸アミドの製法
US3136770A (en)	1964-06-09	Indolyl substituted piperidines
HUT61966A (en)	1993-03-29	Process for producing new phenylalkyl aminoalkyl derivatives and pharmaceutical compositions comprising such compounds
US4252824A (en)	1981-02-24	Amino-ethanol derivatives
US4897412A (en)	1990-01-30	Imidazolines useful in lowering intraocular pressure
US4801617A (en)	1989-01-31	Iminoimidazolidines useful in lowering intraocular pressure
US2657209A (en)	1953-10-27	Tertiary-aminoalkyl 4-alkylamino-2-alkoxy-benzoates and their synthesis
EP0750607B1 (de)	1999-05-06	2-(aminoalkoxy) phenylalkylamine mit entzündungskennenden eigenschaften
IE46612B1 (en)	1983-08-10	1-amino-alkyl-3,4-diphenyl-1h-pyrazoles
Topliss et al.	1967	Synthesis of Some Dibenzo [b, f][1, 5] diazocines and Dibenzo [b, f][1, 4] diazocines