DE2209467A1 - Derivate des 1-phenoxy-3-amino-propan2-ols und verfahren zu ihrer herstellung - Google Patents
Derivate des 1-phenoxy-3-amino-propan2-ols und verfahren zu ihrer herstellungInfo
- Publication number
- DE2209467A1 DE2209467A1 DE2209467A DE2209467A DE2209467A1 DE 2209467 A1 DE2209467 A1 DE 2209467A1 DE 2209467 A DE2209467 A DE 2209467A DE 2209467 A DE2209467 A DE 2209467A DE 2209467 A1 DE2209467 A1 DE 2209467A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- derivatives
- phenoxy
- carbon atoms
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical class NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 69
- -1 AlL: enylo: iy Chemical group 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 208000001953 Hypotension Diseases 0.000 claims description 2
- 239000000150 Sympathomimetic Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 229940124630 bronchodilator Drugs 0.000 claims description 2
- 239000000168 bronchodilator agent Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 230000036543 hypotension Effects 0.000 claims description 2
- 125000005394 methallyl group Chemical group 0.000 claims description 2
- 239000000932 sedative agent Substances 0.000 claims description 2
- 229940125723 sedative agent Drugs 0.000 claims description 2
- 229940127230 sympathomimetic drug Drugs 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 235000015961 tonic Nutrition 0.000 claims 1
- 230000001256 tonic effect Effects 0.000 claims 1
- 229960000716 tonics Drugs 0.000 claims 1
- 229940124549 vasodilator Drugs 0.000 claims 1
- 239000003071 vasodilator agent Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 239000003921 oil Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 239000012279 sodium borohydride Substances 0.000 description 10
- 229910000033 sodium borohydride Inorganic materials 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229940072033 potash Drugs 0.000 description 6
- 235000015320 potassium carbonate Nutrition 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002026 chloroform extract Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- VXKWVOPELVBBFB-UHFFFAOYSA-N 1-amino-3-(2-ethoxyphenoxy)propan-2-ol Chemical compound CCOC1=CC=CC=C1OCC(O)CN VXKWVOPELVBBFB-UHFFFAOYSA-N 0.000 description 1
- WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-UHFFFAOYSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- FZONULHLKBOHHY-UHFFFAOYSA-N 2-[(2-prop-2-enoxyphenoxy)methyl]oxirane Chemical compound C=CCOC1=CC=CC=C1OCC1OC1 FZONULHLKBOHHY-UHFFFAOYSA-N 0.000 description 1
- FNEJKCGACRPXBT-UHFFFAOYSA-N 2-prop-2-enoxyphenol Chemical compound OC1=CC=CC=C1OCC=C FNEJKCGACRPXBT-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ASVDRUPOBTVUIS-UHFFFAOYSA-N 3-(benzylamino)-1-pyridin-3-ylprop-2-en-1-one Chemical compound C=1C=CN=CC=1C(=O)C=CNCC1=CC=CC=C1 ASVDRUPOBTVUIS-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 240000001879 Digitalis lutea Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 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 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical compound [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical compound [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960002155 chlorothiazide Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 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
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000007479 molecular analysis Methods 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229940080360 rauwolfia alkaloid Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (37)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE787057D BE787057A (fr) | 1971-08-03 | Derives du phenoxy-1 amino-3 propanol-2 et medicaments qui en contiennent | |
| RO7200080406A RO64864A (fr) | 1971-08-03 | 1972-01-08 | Procede pour la preparation des derives du 1-phenoxy-3-aminopropan-2-ole |
| NL7210194A NL7210194A (en, 2012) | 1971-08-03 | 1972-07-24 | |
| IE1043/72A IE36595B1 (en) | 1971-08-03 | 1972-07-25 | Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their production |
| IL39992A IL39992A (en) | 1971-08-03 | 1972-07-25 | Derivatives of 1-phenoxy-3-aminopropan-2-ol,their production and pharmaceutical compositions containing them |
| GB3476372A GB1362168A (en) | 1971-08-03 | 1972-07-25 | Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their producrion |
| SU1816878A SU457211A3 (ru) | 1971-08-03 | 1972-07-31 | Способ получени производных 1-фенокси -3-аминопропан-2-ола |
| SE7209959A SE398642B (sv) | 1971-08-03 | 1972-07-31 | Forfarande for framstellning av 1-fenoxi-3-subst amino-propan-2-oler |
| SU1971628A SU487484A3 (ru) | 1971-08-03 | 1972-07-31 | Способ получени производных 1-фенокси3-аминопропан-2-ола |
| PL18132272A PL94712B1 (pl) | 1972-02-29 | 1972-08-01 | Sposob wytwarzania nowych pochodnych 1-fenoksy-3-aminopropanolu-2 |
| RO7280408A RO64866A (fr) | 1971-08-03 | 1972-08-01 | Procede pour la preparation des derives du 1-phenoxy-3-amino-propan-2-ole |
| RO197280407A RO64865A (fr) | 1971-08-03 | 1972-08-01 | Procede pour la preparation des derives du 1-phenoxy-3-aminopropanole |
| PL1972157055A PL93792B1 (en) | 1971-08-03 | 1972-08-01 | Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their producrion[gb1362168a] |
| RO7200071821A RO62788A (fr) | 1971-08-03 | 1972-08-01 | Procede pour la preparation des derives de 1-phenoxy-3-amino-propane-2-ole |
| PL1972181321A PL94261B1 (en) | 1971-08-03 | 1972-08-01 | Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their producrion[gb1362168a] |
| PL1972181323A PL94243B1 (en) | 1971-08-03 | 1972-08-01 | Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their producrion[gb1362168a] |
| AR243372A AR203000A1 (es) | 1971-08-03 | 1972-08-01 | Procedimiento para la obtencion de derivados de 1-fenoxi-3-amino-propan-2-ol |
| FR7227840A FR2150720B1 (en, 2012) | 1971-08-03 | 1972-08-02 | |
| AT164574*1A AT323174B (de) | 1971-08-03 | 1972-08-02 | Verfahren zur herstellung von neuen derivaten des 1-phenoxy-3-amino-propan-2-ols und deren saureadditionssalzen |
| CA148,527A CA984839A (en) | 1971-08-03 | 1972-08-02 | Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their production |
| DD164829A DD98673A5 (en, 2012) | 1971-08-03 | 1972-08-02 | |
| AT667272A AT323167B (de) | 1971-08-03 | 1972-08-02 | Verfahren zur herstellung von neuen derivaten des 1-phenoxy-3-amino-propan-2-ols und deren säureadditionssalzen |
| AT164674A AT323175B (de) | 1972-02-29 | 1972-08-02 | Verfahren zur herstellung von neuen derivaten des 1-phenoxy-3-amino-propan-2-ols und deren saureadditionssalzen |
| AT164774*1A AT323176B (de) | 1971-08-03 | 1972-08-02 | Verfahren zur herstellung von neuen derivaten des 1-phenoxy-3-amino-propan-2-ols und deren saureadditionssalzen |
| HUCA333A HU165016B (en, 2012) | 1971-08-03 | 1972-08-03 | |
| HUCA000350 HU167906B (en, 2012) | 1972-02-29 | 1972-08-03 | |
| ES405484A ES405484A1 (es) | 1971-08-03 | 1972-08-03 | Procedimiento para la obtencion de derivados de 1-fenoxi-3-amino-propan-2-ol. |
| ES407063A ES407063A1 (es) | 1971-08-03 | 1972-09-27 | Procedimiento para la obtencion de derivados de 1-fenoxi-3-amino-propan-2-ol. |
| ES407062A ES407062A1 (es) | 1971-08-03 | 1972-09-27 | Procedimiento para la obtencion de derivados de 1-fenoxi-3-amino-propan-2-ol. |
| ES407061A ES407061A1 (es) | 1971-08-03 | 1972-09-27 | Procedimiento para la obtencion de derivados de 1-fenoxi-3-amino-propan-2-ol. |
| AR249497A AR207847A1 (es) | 1971-08-03 | 1973-01-01 | Procedimiento para la obtencion de derivados de 1-fenoxi-3amino-propan-2-ol |
| CH209573A CH581111A5 (en, 2012) | 1972-02-29 | 1973-02-14 | |
| CH209473A CH581110A5 (en) | 1972-02-29 | 1973-02-14 | Substd 1-pyridyl-3(3-phenoxy-2-hydroxypropylamino)-propan-1-ols - and prop-2-ene-1-ones - antiarrhythmics and anoretics |
| AR249499A AR209578A1 (es) | 1971-08-03 | 1973-08-08 | Procedimiento para la obtencion de derivados de 1-piridil-3-(3-fenoxi-2-hidroxipropilamino)-propanol-1- |
| AR249498A AR209577A1 (es) | 1971-08-03 | 1973-08-08 | Procedimiento para la obtencion de 1-fenoxi-3-amino-propan-2-ol-n-sustituido |
| SU1971626A SU488401A3 (ru) | 1972-02-29 | 1973-11-26 | Способ получени производных 1-фенокси-3-аминопропан-2-ола |
| SU1971627A SU481150A3 (ru) | 1971-08-03 | 1973-11-26 | Способ получени производных 1-фенокси-3-аминопропан-2-ола |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1141571A CH578532A5 (en, 2012) | 1971-08-03 | 1971-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2209467A1 true DE2209467A1 (de) | 1973-02-15 |
Family
ID=4373277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2209467A Pending DE2209467A1 (de) | 1971-08-03 | 1972-02-29 | Derivate des 1-phenoxy-3-amino-propan2-ols und verfahren zu ihrer herstellung |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3830806A (en, 2012) |
| AU (1) | AU464140B2 (en, 2012) |
| CH (3) | CH578532A5 (en, 2012) |
| DE (1) | DE2209467A1 (en, 2012) |
| ZA (1) | ZA725316B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4018778A (en) * | 1972-05-24 | 1977-04-19 | Cassella Farbwerke Mainkur Aktiengesellschaft | Derivatives of 1-phenoxy-3-amino-propane-2-ol and process for their production |
| LU65414A1 (en, 2012) * | 1972-05-24 | 1973-12-04 | ||
| LU69043A1 (en, 2012) * | 1973-12-20 | 1975-08-20 | ||
| US4088764A (en) * | 1973-12-27 | 1978-05-09 | Cassella Farbwerke Mainkur Aktiengesellschaft | Pharmaceutically active derivatives of 1-phenoxy-3-amino-propan-2-ol |
| US4066768A (en) * | 1973-12-27 | 1978-01-03 | Cassella Farbwerke Mainkur Aktiengesellschaft | Derivatives of 1-phenoxy-3-amino-propan-2-ol |
| US4036843A (en) * | 1975-11-14 | 1977-07-19 | Interx Research Corporation | Certain chloroamino esters of pyridine carboxylates and derivatives thereof |
| GB0229583D0 (en) * | 2002-12-19 | 2003-01-22 | Cipla Ltd | A process for preparing duloxetine and intermediates for use therein |
| US20040233639A1 (en) * | 2003-01-31 | 2004-11-25 | Cooligy, Inc. | Removeable heat spreader support mechanism and method of manufacturing thereof |
-
1971
- 1971-08-03 CH CH1141571A patent/CH578532A5/xx not_active IP Right Cessation
-
1972
- 1972-02-29 DE DE2209467A patent/DE2209467A1/de active Pending
- 1972-07-26 AU AU44972/72A patent/AU464140B2/en not_active Expired
- 1972-07-28 US US00276029A patent/US3830806A/en not_active Expired - Lifetime
- 1972-08-02 ZA ZA725316A patent/ZA725316B/xx unknown
-
1976
- 1976-05-20 CH CH1141571A patent/CH582149A5/xx not_active IP Right Cessation
- 1976-05-20 CH CH1141571A patent/CH582148A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA725316B (en) | 1973-05-30 |
| CH582148A5 (en, 2012) | 1976-11-30 |
| AU4497272A (en) | 1974-01-31 |
| CH578532A5 (en, 2012) | 1976-08-13 |
| AU464140B2 (en) | 1975-08-14 |
| US3830806A (en) | 1974-08-20 |
| CH582149A5 (en, 2012) | 1976-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OHA | Expiration of time for request for examination |