DE2702600A1 - Neue aminoalkoxyphenyl-derivate - Google Patents
Neue aminoalkoxyphenyl-derivateInfo
- Publication number
- DE2702600A1 DE2702600A1 DE19772702600 DE2702600A DE2702600A1 DE 2702600 A1 DE2702600 A1 DE 2702600A1 DE 19772702600 DE19772702600 DE 19772702600 DE 2702600 A DE2702600 A DE 2702600A DE 2702600 A1 DE2702600 A1 DE 2702600A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- methyl
- hydrogen atom
- phenyl
- carbon atoms
- 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.)
- Ceased
Links
- -1 methoxyphenyl Chemical group 0.000 claims description 103
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- 150000001875 compounds Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 150000007522 mineralic acids Chemical class 0.000 claims description 11
- 150000007524 organic acids Chemical class 0.000 claims description 11
- 235000005985 organic acids Nutrition 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 3
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 3
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical class CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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 3
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 230000008018 melting Effects 0.000 description 43
- 238000002844 melting Methods 0.000 description 43
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 4
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 241000251730 Chondrichthyes Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 description 2
- 230000003257 anti-anginal effect Effects 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DNTKUYPEHLUNDP-UHFFFAOYSA-N 1-amino-3-(4-methylphenyl)propan-2-ol Chemical compound CC1=CC=C(CC(O)CN)C=C1 DNTKUYPEHLUNDP-UHFFFAOYSA-N 0.000 description 1
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- VVSPINIYNIVDMM-UHFFFAOYSA-N 2,3-dimethoxyisoquinolin-1-one Chemical compound C1=CC=C2C(=O)N(OC)C(OC)=CC2=C1 VVSPINIYNIVDMM-UHFFFAOYSA-N 0.000 description 1
- NFOUTENTJWWWJN-UHFFFAOYSA-N 2-methoxyisoquinolin-1-one Chemical compound C1=CC=C2C(=O)N(OC)C=CC2=C1 NFOUTENTJWWWJN-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- KCRUZAOXZRXNPB-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-methoxy-2-methylisoquinolin-1-one Chemical compound CN1C(=O)C2=CC(OC)=CC=C2C=C1C1=CC=C(O)C=C1 KCRUZAOXZRXNPB-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
- DXVQSHRBALIFBC-UHFFFAOYSA-N 3-phenoxypropan-1-amine Chemical compound NCCCOC1=CC=CC=C1 DXVQSHRBALIFBC-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- UXAZFUABINHWGY-UHFFFAOYSA-N 7-methoxy-2h-isoquinolin-1-one Chemical compound C1=CNC(=O)C2=CC(OC)=CC=C21 UXAZFUABINHWGY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-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
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 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
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical group C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 230000003601 intercostal effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 239000007788 liquid 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
- 239000011976 maleic acid Substances 0.000 description 1
- XUKREMQRQYAKLW-UHFFFAOYSA-N n,n-diethyl-3,4-dimethoxyaniline Chemical compound CCN(CC)C1=CC=C(OC)C(OC)=C1 XUKREMQRQYAKLW-UHFFFAOYSA-N 0.000 description 1
- RUSPWDWPGXKTFO-UHFFFAOYSA-N n-ethyl-2-methoxyaniline Chemical compound CCNC1=CC=CC=C1OC RUSPWDWPGXKTFO-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Priority Applications (37)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772702600 DE2702600A1 (de) | 1977-01-22 | 1977-01-22 | Neue aminoalkoxyphenyl-derivate |
| FI773717A FI63393C (fi) | 1977-01-22 | 1977-12-09 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla isokinolin-1(2h)-oner eller 1,6-naftyridin-5(6h)oner |
| BG038210A BG28573A3 (bg) | 1977-01-22 | 1977-12-26 | Метод за получаване на аминоалкоксифенилови производни |
| ES465455A ES465455A1 (es) | 1977-01-22 | 1977-12-27 | Procedimiento para la preparacion de nuevos derivados amino-alcoxifenilicos. |
| US05/867,308 US4154837A (en) | 1977-01-22 | 1978-01-06 | (Aminoalkoxy-aryl)-substituted isoquinolinones and naphthydrinones and salts thereof, and hypotensive compositions and methods employing them |
| AT11078A AT361480B (de) | 1977-01-22 | 1978-01-09 | Verfahren zur herstellung von neuen amino- alkoxyphenyl-derivaten und deren physiologisch vertraeglichen saeureadditionssalzen |
| RO7892901A RO72911A (ro) | 1977-01-22 | 1978-01-13 | Procedeu pentru prepararea unor izochinolin-1(2h)-one si 1,6-naftiridin-5(6h)-one |
| SU782566499A SU677654A3 (ru) | 1977-01-22 | 1978-01-17 | Способ получени производных аминоалкоксифенила или их солей |
| CH52378A CH640227A5 (de) | 1977-01-22 | 1978-01-18 | Aminoalkoxyphenyl-derivate. |
| CS78380A CS195653B2 (en) | 1977-01-22 | 1978-01-19 | Method of producing new aminoalkoxyphenylderivatives |
| DD78203307A DD135283A5 (de) | 1977-01-22 | 1978-01-19 | Verfahren zur herstellung von neuen aminoalkoxyphenyl-derivaten |
| YU134/78A YU40504B (en) | 1977-01-22 | 1978-01-19 | Process for preparing new aminoalkoxyphenenyl derivatives |
| ZA00780365A ZA78365B (en) | 1977-01-22 | 1978-01-20 | Improvements relating to aminoalkoxyphenyl derivates |
| IE139/78A IE46376B1 (en) | 1977-01-22 | 1978-01-20 | Isoquinoline and naphthyridine substituted aminoalkoxyphenyl derivatives |
| AU32581/78A AU516692B2 (en) | 1977-01-02 | 1978-01-20 | Isoquinoline and 1,6-naphtyridine derivitives |
| NL7800717A NL7800717A (nl) | 1977-01-22 | 1978-01-20 | Nieuwe aminoalkoxyfenyl-derivaten. |
| LU78919A LU78919A1 (de) | 1977-01-22 | 1978-01-20 | Verfahren zur herstellung von neuen aminoalkoxyphenyl-derivaten |
| DK30578A DK149847C (da) | 1977-01-22 | 1978-01-20 | Analogifremgangsmaade til fremstilling af aminoalkoxyphenyl-derivater af isoquinolinoner eller napthyridinoner |
| FR7801684A FR2378014A1 (fr) | 1977-01-22 | 1978-01-20 | Nouveaux derives aminoalcoxyphenyles, leur preparation et leur utilisation en tant que medicaments |
| PT67561A PT67561B (de) | 1977-01-22 | 1978-01-20 | Neue aminoalkoxyphenyl-derivate |
| BE184522A BE863160A (fr) | 1977-01-22 | 1978-01-20 | Nouveaux derives aminoalcoxyphenyles, leur preparation et leur utilisation en tant que medicaments |
| CA295,361A CA1106846A (en) | 1977-01-22 | 1978-01-20 | Aminoalkoxyphenyl-derivatives |
| JP514978A JPS5392786A (en) | 1977-01-22 | 1978-01-20 | Novel aminoalkoxyphenyl derivative |
| GR55214A GR64093B (en) | 1977-01-22 | 1978-01-20 | Method for the preparation of new aminoalkoxyphenyl-derivatives |
| SE7800739A SE444433B (sv) | 1977-01-22 | 1978-01-20 | Forfarande for framstellning av nya aminoalkoxifenylderivat |
| HU78TO1068A HU176895B (en) | 1977-01-22 | 1978-01-20 | Process for preparing new aminoalkoxy-phenyl-derivatives |
| NO780214A NO149502C (no) | 1977-01-22 | 1978-01-20 | Analogifremgangsmaate for fremstilling av fysiologisk aktive aminoalkoksyfenylderivater |
| IL53857A IL53857A (en) | 1977-01-22 | 1978-01-20 | 3-aminopropoxyphenyl (alkyl) isoquinolin-1(2h)-one (or 1,6-naphthyridine-5(6h)-one) derivatives, their preparation and pharmaceutical compositions containing them |
| IT47729/78A IT1102816B (it) | 1977-01-22 | 1978-01-20 | Derivati amminoalcossifinilici e procedimento per la loro preparazione |
| NZ186287A NZ186287A (en) | 1977-01-22 | 1978-01-20 | 3-(3'-substituted-diaminopropoxy(phenyl or phenalkyl)-iso-quinolin-1(2h)-ones or napthyridin-1(2h)-ones |
| PH20691A PH13911A (en) | 1977-01-22 | 1978-01-20 | Neue aminoalkoxyphenyl-derivate |
| PL1978204134A PL112130B1 (en) | 1977-01-22 | 1978-01-21 | Method of manufacturing of novel aminoalkoxyphenyl derivatives |
| GB2643/78A GB1568021A (en) | 1977-01-22 | 1978-01-23 | Isoquinoline and naphthyridine substituted aminoalkoxphenol derivatives |
| AT614979A AT361485B (de) | 1977-01-22 | 1979-09-19 | Verfahren zur herstellung von neuen amino- alkoxyphenyl-derivaten und deren physiologisch vertraeglichen saeureadditionssalzen |
| SG42883A SG42883G (en) | 1977-01-22 | 1983-07-19 | Isoquinoline and naphthyridine substituted aminoalkoxyphenyl derivatives |
| HK600/83A HK60083A (en) | 1977-01-22 | 1983-11-24 | Isoquinoline and naphthyridine substituted aminoalkoxyphenyl derivatives |
| MY275/84A MY8400275A (en) | 1977-01-22 | 1984-12-30 | Isoquinoline and naphthyridine substituted aminoalkoxy-phenyl derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772702600 DE2702600A1 (de) | 1977-01-22 | 1977-01-22 | Neue aminoalkoxyphenyl-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2702600A1 true DE2702600A1 (de) | 1978-07-27 |
Family
ID=5999300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772702600 Ceased DE2702600A1 (de) | 1977-01-02 | 1977-01-22 | Neue aminoalkoxyphenyl-derivate |
Country Status (36)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0113910A1 (en) * | 1982-12-24 | 1984-07-25 | Nisshin Flour Milling Co., Ltd. | Isocarbostyril derivatives, processes for their preparation and pharmaceutical compositions containing them |
| DE3423003A1 (de) * | 1984-06-22 | 1986-01-02 | Beiersdorf Ag, 2000 Hamburg | Benzo(c)(1,8)naphthyridine, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen |
| DE3526693A1 (de) * | 1984-07-26 | 1986-02-06 | Mitsui Toatsu Chemicals, Inc., Tokio/Tokyo | Isochinolin-derivat |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3027619A1 (de) * | 1979-07-25 | 1981-02-19 | Sandoz Ag | 6-alkyl-7-phenyl-1,6-naphtyradin- 5(6h)-on-derivate |
| US4329349A (en) * | 1979-07-25 | 1982-05-11 | Sandoz, Inc. | 6-C1-4 Alkyl-7-phenyl or substituted phenyl-1,6-naphthyridine-5(6H)-ones |
| DE3502831A1 (de) * | 1985-01-29 | 1986-07-31 | Gödecke AG, 1000 Berlin | 1,6-naphthyridinon-derivate, verfahren zu deren herstellung und deren verwendung |
| US4698341A (en) * | 1983-07-30 | 1987-10-06 | Godecke Aktiengesellschaft | Use of 1,6-naphthyridinone derivatives in treating pulmonary thrombosis |
| DE69531691T2 (de) * | 1994-08-04 | 2004-07-08 | C & C Research Labs | Neues amin-derivat, verfahren zur herstellung und dessen verwendung als anti-arrhythmisches mittel |
| DE19943635A1 (de) * | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| CA2569081A1 (en) * | 2004-05-31 | 2005-12-08 | Takashi Mizutani | Quinazoline derivative |
| EP2303845B1 (en) * | 2008-06-24 | 2013-09-18 | Sanofi | Bi-and polycyclic substituted isoquinoline and isoquinoline derivatives as rho kinase inhibitors |
| PT2303846E (pt) * | 2008-06-24 | 2015-09-04 | Sanofi Sa | Isoquinolinas e isoquinolinonas substituídas como inibidores de rho-quinase |
| PE20110054A1 (es) * | 2008-06-24 | 2011-02-15 | Sanofi Aventis | Isoquinolinas e isoquinolinonas 6-sustituidas |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1394700A (en) * | 1972-11-25 | 1975-05-21 | Aspro Nicholas Ltd | Pharmacologically active isoquinoline derivatives |
| GB1446791A (en) * | 1973-09-08 | 1976-08-18 | Thomae Gmbh Dr K | 1,3-diketo-1,2,3,4-tetrahydroisoquinolines |
| DE2615406A1 (de) * | 1975-04-09 | 1976-10-14 | Abbott Lab | Beta-adrenergische rezeptoren-blocker |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2538341A (en) * | 1949-09-20 | 1951-01-16 | Smith Kline French Lab | Method for producing 1-hydroxyisoquinolines |
| US3432027A (en) * | 1966-01-05 | 1969-03-11 | Lily Tulip Cup Corp | Dispensing container assembly |
| US3993656A (en) * | 1974-11-19 | 1976-11-23 | Merck & Co., Inc. | 1,8-Naphthyridine compounds |
| SE7603371L (sv) * | 1975-03-26 | 1976-09-27 | Sandoz Ag | Organiska foreningar, deras anvendning och framstellning |
-
1977
- 1977-01-22 DE DE19772702600 patent/DE2702600A1/de not_active Ceased
- 1977-12-09 FI FI773717A patent/FI63393C/fi not_active IP Right Cessation
- 1977-12-26 BG BG038210A patent/BG28573A3/xx unknown
- 1977-12-27 ES ES465455A patent/ES465455A1/es not_active Expired
-
1978
- 1978-01-06 US US05/867,308 patent/US4154837A/en not_active Expired - Lifetime
- 1978-01-09 AT AT11078A patent/AT361480B/de not_active IP Right Cessation
- 1978-01-13 RO RO7892901A patent/RO72911A/ro unknown
- 1978-01-17 SU SU782566499A patent/SU677654A3/ru active
- 1978-01-18 CH CH52378A patent/CH640227A5/de not_active IP Right Cessation
- 1978-01-19 YU YU134/78A patent/YU40504B/xx unknown
- 1978-01-19 DD DD78203307A patent/DD135283A5/xx unknown
- 1978-01-19 CS CS78380A patent/CS195653B2/cs unknown
- 1978-01-20 NZ NZ186287A patent/NZ186287A/xx unknown
- 1978-01-20 LU LU78919A patent/LU78919A1/de unknown
- 1978-01-20 CA CA295,361A patent/CA1106846A/en not_active Expired
- 1978-01-20 IT IT47729/78A patent/IT1102816B/it active
- 1978-01-20 GR GR55214A patent/GR64093B/el unknown
- 1978-01-20 FR FR7801684A patent/FR2378014A1/fr active Granted
- 1978-01-20 AU AU32581/78A patent/AU516692B2/en not_active Expired
- 1978-01-20 PH PH20691A patent/PH13911A/en unknown
- 1978-01-20 HU HU78TO1068A patent/HU176895B/hu unknown
- 1978-01-20 ZA ZA00780365A patent/ZA78365B/xx unknown
- 1978-01-20 DK DK30578A patent/DK149847C/da not_active IP Right Cessation
- 1978-01-20 IL IL53857A patent/IL53857A/xx unknown
- 1978-01-20 JP JP514978A patent/JPS5392786A/ja active Pending
- 1978-01-20 NL NL7800717A patent/NL7800717A/xx not_active Application Discontinuation
- 1978-01-20 NO NO780214A patent/NO149502C/no unknown
- 1978-01-20 IE IE139/78A patent/IE46376B1/en unknown
- 1978-01-20 SE SE7800739A patent/SE444433B/sv not_active IP Right Cessation
- 1978-01-20 PT PT67561A patent/PT67561B/pt unknown
- 1978-01-20 BE BE184522A patent/BE863160A/xx not_active IP Right Cessation
- 1978-01-21 PL PL1978204134A patent/PL112130B1/pl unknown
- 1978-01-23 GB GB2643/78A patent/GB1568021A/en not_active Expired
-
1983
- 1983-07-19 SG SG42883A patent/SG42883G/en unknown
- 1983-11-24 HK HK600/83A patent/HK60083A/xx unknown
-
1984
- 1984-12-30 MY MY275/84A patent/MY8400275A/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1394700A (en) * | 1972-11-25 | 1975-05-21 | Aspro Nicholas Ltd | Pharmacologically active isoquinoline derivatives |
| GB1446791A (en) * | 1973-09-08 | 1976-08-18 | Thomae Gmbh Dr K | 1,3-diketo-1,2,3,4-tetrahydroisoquinolines |
| DE2615406A1 (de) * | 1975-04-09 | 1976-10-14 | Abbott Lab | Beta-adrenergische rezeptoren-blocker |
Non-Patent Citations (3)
| Title |
|---|
| Chemical Abstracts, Bd. 80, 1974, 133455 a * |
| Chemical Abstracts, Bd. 80, 1974, 82715 a * |
| NEGWER: Organisch Chemische Arzneimittel und ihre Synonyma, Bd. 1, 1971, S.468 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0113910A1 (en) * | 1982-12-24 | 1984-07-25 | Nisshin Flour Milling Co., Ltd. | Isocarbostyril derivatives, processes for their preparation and pharmaceutical compositions containing them |
| DE3423003A1 (de) * | 1984-06-22 | 1986-01-02 | Beiersdorf Ag, 2000 Hamburg | Benzo(c)(1,8)naphthyridine, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen |
| DE3526693A1 (de) * | 1984-07-26 | 1986-02-06 | Mitsui Toatsu Chemicals, Inc., Tokio/Tokyo | Isochinolin-derivat |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |