DE1593762A1 - Verfahren zur Herstellung von neuen substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen - Google Patents
Verfahren zur Herstellung von neuen substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanenInfo
- Publication number
- DE1593762A1 DE1593762A1 DE19671593762 DE1593762A DE1593762A1 DE 1593762 A1 DE1593762 A1 DE 1593762A1 DE 19671593762 DE19671593762 DE 19671593762 DE 1593762 A DE1593762 A DE 1593762A DE 1593762 A1 DE1593762 A1 DE 1593762A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- general formula
- hydroxy
- group
- acid addition
- 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 24
- 238000002360 preparation method Methods 0.000 title claims description 6
- -1 alkyl radical Chemical class 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000000126 substance Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 4
- RNFDZDMIFOFNMC-UHFFFAOYSA-N 1-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(C)O RNFDZDMIFOFNMC-UHFFFAOYSA-N 0.000 claims description 3
- WOIUAXCQCROIIH-UHFFFAOYSA-N 2-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methoxybenzonitrile Chemical compound COC1=C(OCC(CNC(C)C)O)C(=CC=C1)C#N WOIUAXCQCROIIH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- 239000000969 carrier Substances 0.000 claims 4
- KRTIALANBMISKJ-UHFFFAOYSA-N 1-[3-(hydroxymethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC(CO)=C1 KRTIALANBMISKJ-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 97
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 93
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- 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 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000002585 base Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical class OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 230000001376 precipitating effect Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- IKLHTJKCEKYJKI-UHFFFAOYSA-N methyl 4-[2-hydroxy-3-(propan-2-ylamino)propoxy]benzoate Chemical compound COC(=O)C1=CC=C(OCC(O)CNC(C)C)C=C1 IKLHTJKCEKYJKI-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N 1,3-di(propan-2-yl)urea Chemical compound CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
- WGJVNJGGPWONPI-UHFFFAOYSA-N 1-[2-(hydroxymethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CO WGJVNJGGPWONPI-UHFFFAOYSA-N 0.000 description 2
- FOTUTVUVKRWYLP-UHFFFAOYSA-N 2-[2-hydroxy-3-(propan-2-ylamino)propoxy]benzoic acid Chemical compound OC(=O)C1=C(OCC(CNC(C)C)O)C=CC=C1 FOTUTVUVKRWYLP-UHFFFAOYSA-N 0.000 description 2
- QAIHVGXGYVRHCY-UHFFFAOYSA-N 3-methoxy-4-(oxiran-2-ylmethoxy)benzonitrile Chemical compound COC1=CC(C#N)=CC=C1OCC1OC1 QAIHVGXGYVRHCY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- CDNNMNLILHWPMH-UHFFFAOYSA-N methyl 2-(oxiran-2-ylmethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC1OC1 CDNNMNLILHWPMH-UHFFFAOYSA-N 0.000 description 2
- ZRNPUKBJZYJWCD-UHFFFAOYSA-N methyl 2-[2-hydroxy-3-(propan-2-ylamino)propoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC(O)CNC(C)C ZRNPUKBJZYJWCD-UHFFFAOYSA-N 0.000 description 2
- GVMPCQYYYYFGMV-UHFFFAOYSA-N methyl 4-(oxiran-2-ylmethoxy)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCC1OC1 GVMPCQYYYYFGMV-UHFFFAOYSA-N 0.000 description 2
- VLSTXUUYLIALPB-UHFFFAOYSA-N n-propan-2-ylpropan-1-amine Chemical compound CCCNC(C)C VLSTXUUYLIALPB-UHFFFAOYSA-N 0.000 description 2
- CWYZDPHNAGSFQB-UHFFFAOYSA-N n-propylbutan-1-amine Chemical compound CCCCNCCC CWYZDPHNAGSFQB-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- XUJHKPSBHDQIOD-UHFFFAOYSA-N (2-bromo-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)C(Br)C1C2(C)C XUJHKPSBHDQIOD-UHFFFAOYSA-N 0.000 description 1
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- IJOZLEKFOBXYFP-UHFFFAOYSA-N 1-[2-(aminomethyl)-4-chlorophenoxy]-3-(tert-butylamino)propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=C(Cl)C=C1CN IJOZLEKFOBXYFP-UHFFFAOYSA-N 0.000 description 1
- YRSLUHURHMRNES-UHFFFAOYSA-N 1-[3-(aminomethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound NCC=1C=C(OCC(CNC(C)C)O)C=CC1 YRSLUHURHMRNES-UHFFFAOYSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- WWAZTASVHNCPKL-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)phenyl]acetonitrile Chemical compound C(#N)CC1=C(OCC2CO2)C=CC=C1 WWAZTASVHNCPKL-UHFFFAOYSA-N 0.000 description 1
- WDGZJFDDPCUVPF-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)phenyl]acetonitrile Chemical compound C1=CC(CC#N)=CC=C1OCC1OC1 WDGZJFDDPCUVPF-UHFFFAOYSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- PGOFJDZYVIIGGD-UHFFFAOYSA-N 3-(tert-butylamino)propan-1-ol Chemical compound CC(C)(C)NCCCO PGOFJDZYVIIGGD-UHFFFAOYSA-N 0.000 description 1
- VFLPZPDGVMHHNJ-UHFFFAOYSA-N 3-[2-hydroxy-3-(propan-2-ylamino)propoxy]-4-methoxybenzonitrile Chemical compound COC1=C(OCC(CNC(C)C)O)C=C(C=C1)C#N VFLPZPDGVMHHNJ-UHFFFAOYSA-N 0.000 description 1
- MZMXHNPUBSQJHD-UHFFFAOYSA-N 3-[2-hydroxy-3-(propan-2-ylamino)propoxy]benzonitrile Chemical compound CC(C)NCC(O)COC1=CC=CC(C#N)=C1 MZMXHNPUBSQJHD-UHFFFAOYSA-N 0.000 description 1
- FLROJJGKUKLCAE-UHFFFAOYSA-N 3-amino-2-methylphenol Chemical class CC1=C(N)C=CC=C1O FLROJJGKUKLCAE-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
- QPQFUKCQEZJXOZ-UHFFFAOYSA-N 3-methoxy-2-(oxiran-2-ylmethoxy)benzonitrile Chemical compound COC1=C(OCC2CO2)C(=CC=C1)C#N QPQFUKCQEZJXOZ-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- LQRUKKGYJWLGBA-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCC1OC1 LQRUKKGYJWLGBA-UHFFFAOYSA-N 0.000 description 1
- ULMHJUNAXLVTLG-UHFFFAOYSA-N 4-methoxy-3-(oxiran-2-ylmethoxy)benzonitrile Chemical compound COC1=CC=C(C#N)C=C1OCC1OC1 ULMHJUNAXLVTLG-UHFFFAOYSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RGPJJYZIVZBYOX-UHFFFAOYSA-N C(#N)C1=C(OCC(CNC(C)C)O)C=CC(=C1)C#N Chemical compound C(#N)C1=C(OCC(CNC(C)C)O)C=CC(=C1)C#N RGPJJYZIVZBYOX-UHFFFAOYSA-N 0.000 description 1
- SDNSAICNSOZPRH-UHFFFAOYSA-N C(#N)C1=C(OCC2CO2)C=CC(=C1)C#N Chemical compound C(#N)C1=C(OCC2CO2)C=CC(=C1)C#N SDNSAICNSOZPRH-UHFFFAOYSA-N 0.000 description 1
- JDSHWUSBLSNDSV-UHFFFAOYSA-N C(C(=O)O)(=O)O.C(CCC)NCCC Chemical compound C(C(=O)O)(=O)O.C(CCC)NCCC JDSHWUSBLSNDSV-UHFFFAOYSA-N 0.000 description 1
- QYMOZVCIJAEHLE-UHFFFAOYSA-N CC(C)NCC(COC(C=CC(C(OC)=O)=C1)=C1Br)O Chemical compound CC(C)NCC(COC(C=CC(C(OC)=O)=C1)=C1Br)O QYMOZVCIJAEHLE-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XOTFFURKRZZNNH-UHFFFAOYSA-N Cl.COC1=C(OCC(CNC(C)C)O)C(=CC=C1)C#N Chemical compound Cl.COC1=C(OCC(CNC(C)C)O)C(=CC=C1)C#N XOTFFURKRZZNNH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 240000001812 Hyssopus officinalis Species 0.000 description 1
- 235000010650 Hyssopus officinalis Nutrition 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
- 235000019759 Maize starch Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- UKUORLQPIPQXHG-UHFFFAOYSA-N [2-(oxiran-2-ylmethoxy)phenyl]methanol Chemical compound OCC1=CC=CC=C1OCC1OC1 UKUORLQPIPQXHG-UHFFFAOYSA-N 0.000 description 1
- DABFNGAUUSLBNT-UHFFFAOYSA-N [4-(oxiran-2-ylmethoxy)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1OCC1OC1 DABFNGAUUSLBNT-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 150000007962 benzene acetonitriles Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NZIYLLHOEIBFDE-UHFFFAOYSA-N methyl 2-[3-(tert-butylamino)-2-hydroxypropoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC(O)CNC(C)(C)C NZIYLLHOEIBFDE-UHFFFAOYSA-N 0.000 description 1
- NLGAZNQSUHYNGJ-UHFFFAOYSA-N methyl 3-(oxiran-2-ylmethoxy)benzoate Chemical compound COC(=O)C1=CC=CC(OCC2OC2)=C1 NLGAZNQSUHYNGJ-UHFFFAOYSA-N 0.000 description 1
- ZZCUZSVSCQEXKA-UHFFFAOYSA-N methyl 3-[2-hydroxy-3-(propan-2-ylamino)propoxy]benzoate Chemical compound COC(=O)C=1C=C(OCC(CNC(C)C)O)C=CC1 ZZCUZSVSCQEXKA-UHFFFAOYSA-N 0.000 description 1
- JLQJIXKNIOCJSL-UHFFFAOYSA-N methyl 4-(3-amino-2-hydroxypropoxy)benzoate Chemical compound COC(=O)C1=CC=C(OCC(O)CN)C=C1 JLQJIXKNIOCJSL-UHFFFAOYSA-N 0.000 description 1
- SZAYMQLNVXIKNC-UHFFFAOYSA-N methyl 4-[3-(tert-butylamino)-2-hydroxypropoxy]benzoate Chemical compound COC(=O)C1=CC=C(OCC(O)CNC(C)(C)C)C=C1 SZAYMQLNVXIKNC-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT237570A AT291970B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven subtituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen sowie von daren Säureadditionssalzen |
| AT696670A AT291226B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen sowie von deren Säureadditionssalzen |
| AT104368A AT291224B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen sowie von deren Säureadditionssalzen |
| AT237270A AT289068B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen sowie von deren Säureadditionssalzen |
| AT237670A AT289070B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen sowie von deren Säureadditionssalzen |
| AT237870A AT289072B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen sowie von deren Säureadditionssalzen |
| AT237770A AT289071B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen sowie von deren Säureadditionssalzen |
| AT237970A AT289073B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen sowie von deren Säureadditionssalzen |
| AT237470A AT289069B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen sowie von deren Säureadditionssalzen |
| AT644071A AT299915B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-isopropylaminopropanen sowie deren Säureadditionssalzen |
| AT238070A AT289074B (de) | 1967-02-06 | 1968-02-02 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen sowie von deren Säureadditionssalzen |
| AT237370A AT300760B (de) | 1967-02-06 | 1970-03-13 | Verfahren zur herstellung von neuen racemischen oder optisch aktiven substituierten 1-phenoxy-2-hydroxy-3-isopropyl- bzw. -tert.butylaminopropanen sowie deren saeureadditionssalzen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0091070 | 1967-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593762A1 true DE1593762A1 (de) | 1972-06-08 |
Family
ID=6985633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671593762 Pending DE1593762A1 (de) | 1967-02-06 | 1967-02-06 | Verfahren zur Herstellung von neuen substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
Country Status (13)
| Country | Link |
|---|---|
| BE (1) | BE710400A (enrdf_load_stackoverflow) |
| BG (2) | BG15030A3 (enrdf_load_stackoverflow) |
| CH (10) | CH510637A (enrdf_load_stackoverflow) |
| DE (1) | DE1593762A1 (enrdf_load_stackoverflow) |
| ES (9) | ES349847A1 (enrdf_load_stackoverflow) |
| FI (1) | FI49496C (enrdf_load_stackoverflow) |
| FR (2) | FR8040M (enrdf_load_stackoverflow) |
| GB (1) | GB1227480A (enrdf_load_stackoverflow) |
| IE (1) | IE32353B1 (enrdf_load_stackoverflow) |
| IL (1) | IL29416A (enrdf_load_stackoverflow) |
| NL (2) | NL139236B (enrdf_load_stackoverflow) |
| SE (1) | SE359292B (enrdf_load_stackoverflow) |
| YU (4) | YU32701B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0009168A1 (de) * | 1978-09-11 | 1980-04-02 | Dolorgiet Arzneimittelfabrik Peter Doll Kg | Isopropylamin-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA945172A (en) * | 1969-02-21 | 1974-04-09 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| JPS4875539A (enrdf_load_stackoverflow) * | 1972-01-12 | 1973-10-11 | ||
| JPS49245A (enrdf_load_stackoverflow) * | 1972-04-17 | 1974-01-05 | ||
| US4454154A (en) * | 1981-06-23 | 1984-06-12 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| DE3407695A1 (de) * | 1984-03-02 | 1985-09-12 | Röhm Pharma GmbH, 6108 Weiterstadt | Pteridinverbindungen mit pharmazeutischer wirksamkeit |
| US4665094A (en) * | 1985-08-29 | 1987-05-12 | Merck & Co., Inc. | Oculoselective beta-blockers for treatment of elevated intraocular pressure |
-
1967
- 1967-02-06 DE DE19671593762 patent/DE1593762A1/de active Pending
-
1968
- 1968-01-27 ES ES349847A patent/ES349847A1/es not_active Expired
- 1968-02-01 CH CH1374570A patent/CH510637A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374070A patent/CH510634A/de not_active IP Right Cessation
- 1968-02-01 CH CH1373870A patent/CH510632A/de not_active IP Right Cessation
- 1968-02-01 CH CH1373770A patent/CH510631A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374170A patent/CH510635A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374470A patent/CH510636A/de not_active IP Right Cessation
- 1968-02-01 CH CH1373970A patent/CH510633A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374370A patent/CH511212A/de not_active IP Right Cessation
- 1968-02-01 CH CH153968A patent/CH506482A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374270A patent/CH521310A/de not_active IP Right Cessation
- 1968-02-05 YU YU0252/68A patent/YU32701B/xx unknown
- 1968-02-05 IL IL6829416A patent/IL29416A/xx unknown
- 1968-02-06 BG BG011429A patent/BG15030A3/bg unknown
- 1968-02-06 IE IE152/68A patent/IE32353B1/xx unknown
- 1968-02-06 NL NL686801661A patent/NL139236B/xx unknown
- 1968-02-06 BG BG011427A patent/BG15028A3/bg unknown
- 1968-02-06 SE SE01539/68A patent/SE359292B/xx unknown
- 1968-02-06 FR FR138848A patent/FR8040M/fr not_active Expired
- 1968-02-06 GB GB1227480D patent/GB1227480A/en not_active Expired
- 1968-02-06 FI FI680290A patent/FI49496C/fi active
- 1968-02-06 BE BE710400D patent/BE710400A/xx unknown
- 1968-02-06 FR FR1566349D patent/FR1566349A/fr not_active Expired
-
1969
- 1969-07-15 ES ES369541A patent/ES369541A1/es not_active Expired
- 1969-07-15 ES ES369537A patent/ES369537A1/es not_active Expired
- 1969-07-15 ES ES369542A patent/ES369542A1/es not_active Expired
- 1969-07-15 ES ES369538A patent/ES369538A1/es not_active Expired
- 1969-07-15 ES ES369539A patent/ES369539A1/es not_active Expired
- 1969-07-15 ES ES69369544A patent/ES369544A1/es not_active Expired
- 1969-07-15 ES ES369540A patent/ES369540A1/es not_active Expired
- 1969-07-15 ES ES69369543A patent/ES369543A1/es not_active Expired
-
1973
- 1973-02-08 NL NL7301803A patent/NL7301803A/xx unknown
- 1973-06-05 YU YU1498/73A patent/YU32763B/xx unknown
- 1973-06-05 YU YU1493/73A patent/YU32761B/xx unknown
- 1973-06-05 YU YU01494/73A patent/YU149473A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0009168A1 (de) * | 1978-09-11 | 1980-04-02 | Dolorgiet Arzneimittelfabrik Peter Doll Kg | Isopropylamin-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1493955B2 (de) | Sulfonanilide und verfahren zu ihrer herstellung | |
| DE2059618B2 (de) | m-Halogen- a -i-butylaminoproiophenone und deren Salze, Herstellungsverfahren und pharmazeutische Zubereitung | |
| DE2644833A1 (de) | Neue 1-aryloxy-2-hydroxy-3-alkylenaminopropane und verfahren zu ihrer herstellung | |
| DE1643262A1 (de) | Neue 1-Phenoxy-2-hydroxy-3-alkylaminopropane und Verfahren zu ihrer Herstellung | |
| DE1937477A1 (de) | Neue 1-Phenoxy-2-hydroxy-3-cycloalkylaminopropane und Verfahren zu ihrer Herstellung | |
| DE2020864A1 (de) | Phenoxyhydroxypropylamine und Verfahren zu deren Herstellung | |
| DE1593762A1 (de) | Verfahren zur Herstellung von neuen substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen | |
| DE68905171T2 (de) | Benzol-derivate, ihre herstellung und pharmazeutische zusammensetzungen, die diese enthalten. | |
| DE3320394A1 (de) | Optisch aktive n-arylierte oxazolidinon-(2)-derivate, deren verwendung als spezifische und reversible inhibitoren von monoaminooxydase des b-typs sowie verfahren zu deren herstellung | |
| DE1940566A1 (de) | 1-(2-Nitrilophenoxy)-2-hydroxy-3-aethylaminopropan und dessen Salze | |
| DE2364685A1 (de) | Phenoxyalkylamine und verfahren zu ihrer herstellung | |
| EP0011747B1 (de) | Aminopropanolderivate des 6-Hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-ons, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| DE2101415A1 (de) | alpha (Aminoalkyl) benzylalkohol ihre Saureaddirionssalze, Verfahren zu ihrer Herstellung und Arzneipraparate | |
| DE2409313C2 (de) | 1-[2-Pyrrolyl-(1)-phenoxy]-2-hydroxy-3-aminopropan-derivate, Verfahren zu deren Herstellung und pharmazeutische Präparate | |
| DE2324584A1 (de) | Neue amine und verfahren zu ihrer herstellung | |
| DE2421165A1 (de) | N-substituierte dihydroxyphenylaethylamine | |
| DE2547524A1 (de) | Disubstituierte phenolaether des 3-amino-2-hydroxypropans, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE2048838A1 (de) | Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellung | |
| DE1593782A1 (de) | Neue nitrilsubstituierte 1-Phenoxy-2-hydroxy-3-tert.-butylaminopropane und Verfahren zu ihrer Herstellung | |
| DE2313625C2 (de) | α-(Aminoalkyl)-4-hydroxy-3-(methylsulfonylmethyl)-benzylalkohole, ihre Salze, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2609574A1 (de) | Monosubstituiertes piperazinderivat, verfahren zu seiner herstellung und es enthaltende arzneimittel | |
| DE2229931A1 (de) | Verfahren zur herstellung von neuen o-substituierten phenylaethylguanidinen | |
| DE1768974A1 (de) | Neue Diarylacetamide und Herstellungsverfahren | |
| DE1950351A1 (de) | Neue 1-(2-Cyano-5-methylphenoxy)-2-hydroxy-3-alkylaminopropane und Verfahren zu ihrer Herstellung | |
| DE1593782C3 (de) | 1-Nitrilophenoxy- 2- hydroxy -3- tertbutylaminopropane, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |