Detail of "4457-67-4"

Reference

1-Phenoxy-3-aminopropan-2-ol derivatives and their acid addition salts

1-Phenoxy-3-aminopropan-2-ol derivatives and their acid addition salts. (Cassella Farbwerke Mainkur A.-G., Ger.). Austrian AT 339306 10 Oct 1977, 20 pp. (German). (Austria). CODEN: AUXXAK. CLASS: IC: C07D213-30. PRIORITY: LU 73-34590 27 Dec 1973. DOCUMENT TYPE: Patent CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Section cross-reference(s): 28 The title compds. I [R = CR2:CHCOR3, CHR2CH2CH(OH)R3 (R2 = H, Me; R3 = an arom. or quasi-arom. 4457-67-4 are also occured in this study. 5- or 6-membered monocyclic ring, with 1 or 2 N, O, and (or) S atoms, which can be substituted with 1 or more Me groups, and connected via a C atom); R1 = alkoxymethyl, alkoxyalkoxy, hydroxyalkoxy, NHCONR4R5 (R4 and R5 = Ph, alkyl, alkenyl, cycloalkyl; NR4R5 = a satd. 5- or 6-membered heterocyclic group, which may have O or S as an addnl. heteroatom), and contain C1-4 alkyl or alkoxy groups, C3-4 alkenyl groups, and C5-7 cycloalkyl groups] as well as their aldehyde condensation products and acid addn. salts, were prepd. by treating 4-R1C6H4OCH2CH(OH)CH2NH2 with RR6 (R as above, R6 = halo, OH, OK, ONa) and the obtained I, if necessary, converted with R7CHO (R7 = H, C1-4 alkyl) into oxazolidines II or with an acid into acid addn. salts. Thus, e.g., 4-MeO(CH2)4OC6H4OCH2CH(OH)CH2NH2 (III) in EtOH was treated with nicotinoylacetone and the mixt. treated with 1 drop HCO2H and refluxed 3 h to give 78% the nicotinoylvinylamino ether IV. Nicotinoylacetone was prepd. by dropwise treatment of KOCMe3 in C6H6 with EtOAc and 3-acetylpyridine at 10° and keeping the mixt. 24 h at room temp. III was prepd. 4457-67-4 which is the cas registry number is also used here. by heating 4-HOC6H4OCH2Ph with MeO(CH2)4Br in Me2CO with excess K2CO3, hydrogenolysis of the formed 4-MeOC6H4OR8 (V, R8 = CH2Ph), treating the phenol V (R = H) with epichlorohydrin, and ammonolysis of the resulting glycidyl ether V (R = glycidyl). An addnl. 54 I and 1 oxazolidine deriv. were prepd. Selected I had ED50 0.003-0.093 mg/kg (dog) as b1-receptor inhibitors and ED50 1.02-15.59 mg/kg (dog) as b2-receptor inhibitors [vs. 0.238 and 26.505 for 4-Me2CHNHCH2CH(OH)CH2OC6H4NHAc] and are useful in treating arrhythmia and other heart disorders. ..

1-Phenoxy-3-aminopropan-2-ol derivatives and their acid addition salts

1-Phenoxy-3-aminopropan-2-ol derivatives and their acid addition salts. (Cassella Farbwerke Mainkur A.-G., Ger.). Austrian AT 339306 10 Oct 1977, 20 pp. (German). (Austria). CODEN: AUXXAK. CLASS: IC: C07D213-30. PRIORITY: LU 73-34590 27 Dec 1973. DOCUMENT TYPE: Patent CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Section cross-reference(s): 28 The title compds. I [R = CR2:CHCOR3, CHR2CH2CH(OH)R3 (R2 = H, Me; R3 = an arom. or quasi-arom. 4457-67-4 are also occured in this study. 5- or 6-membered monocyclic ring, with 1 or 2 N, O, and (or) S atoms, which can be substituted with 1 or more Me groups, and connected via a C atom); R1 = alkoxymethyl, alkoxyalkoxy, hydroxyalkoxy, NHCONR4R5 (R4 and R5 = Ph, alkyl, alkenyl, cycloalkyl; NR4R5 = a satd. 5- or 6-membered heterocyclic group, which may have O or S as an addnl. heteroatom), and contain C1-4 alkyl or alkoxy groups, C3-4 alkenyl groups, and C5-7 cycloalkyl groups] as well as their aldehyde condensation products and acid addn. salts, were prepd. by treating 4-R1C6H4OCH2CH(OH)CH2NH2 with RR6 (R as above, R6 = halo, OH, OK, ONa) and the obtained I, if necessary, converted with R7CHO (R7 = H, C1-4 alkyl) into oxazolidines II or with an acid into acid addn. salts. Thus, e.g., 4-MeO(CH2)4OC6H4OCH2CH(OH)CH2NH2 (III) in EtOH was treated with nicotinoylacetone and the mixt. treated with 1 drop HCO2H and refluxed 3 h to give 78% the nicotinoylvinylamino ether IV. Nicotinoylacetone was prepd. by dropwise treatment of KOCMe3 in C6H6 with EtOAc and 3-acetylpyridine at 10° and keeping the mixt. 24 h at room temp. III was prepd. 4457-67-4 which is the cas registry number is also used here. by heating 4-HOC6H4OCH2Ph with MeO(CH2)4Br in Me2CO with excess K2CO3, hydrogenolysis of the formed 4-MeOC6H4OR8 (V, R8 = CH2Ph), treating the phenol V (R = H) with epichlorohydrin, and ammonolysis of the resulting glycidyl ether V (R = glycidyl). An addnl. 54 I and 1 oxazolidine deriv. were prepd. Selected I had ED50 0.003-0.093 mg/kg (dog) as b1-receptor inhibitors and ED50 1.02-15.59 mg/kg (dog) as b2-receptor inhibitors [vs. 0.238 and 26.505 for 4-Me2CHNHCH2CH(OH)CH2OC6H4NHAc] and are useful in treating arrhythmia and other heart disorders. ..