DE3004348C2 - - Google Patents
Info
- Publication number
- DE3004348C2 DE3004348C2 DE3004348A DE3004348A DE3004348C2 DE 3004348 C2 DE3004348 C2 DE 3004348C2 DE 3004348 A DE3004348 A DE 3004348A DE 3004348 A DE3004348 A DE 3004348A DE 3004348 C2 DE3004348 C2 DE 3004348C2
- Authority
- DE
- Germany
- Prior art keywords
- chloroethyl
- phenyl
- solution
- alkyl
- ethyl
- 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.)
- Expired - Fee Related
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- -1 2,6-dimethylphenyl Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 11
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 10
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 206010003119 arrhythmia Diseases 0.000 claims description 6
- 239000012876 carrier material Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 208000002177 Cataract Diseases 0.000 claims description 5
- 230000006793 arrhythmia Effects 0.000 claims description 5
- 201000001421 hyperglycemia Diseases 0.000 claims description 5
- GKJZOVORBZCHBD-WLHGVMLRSA-N (e)-but-2-enedioic acid;4-(2-chloroethyl)-1,3-dimethyl-n-phenylimidazolidin-2-imine Chemical compound OC(=O)\C=C\C(O)=O.CN1CC(CCCl)N(C)C1=NC1=CC=CC=C1 GKJZOVORBZCHBD-WLHGVMLRSA-N 0.000 claims description 2
- ZEEUJZMZNQSPDT-UHFFFAOYSA-N 4-(2-chloroethyl)-1-ethyl-3-phenylimidazolidin-2-imine;hydrochloride Chemical compound Cl.N=C1N(CC)CC(CCCl)N1C1=CC=CC=C1 ZEEUJZMZNQSPDT-UHFFFAOYSA-N 0.000 claims description 2
- ATOWTAMTGMZVKI-UHFFFAOYSA-N 4-(2-chloroethyl)-3-(4-chlorophenyl)-1-ethylimidazolidin-2-imine;hydrochloride Chemical compound Cl.N=C1N(CC)CC(CCCl)N1C1=CC=C(Cl)C=C1 ATOWTAMTGMZVKI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims 3
- 230000000747 cardiac effect Effects 0.000 claims 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 72
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000010410 layer Substances 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- 238000007792 addition Methods 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical compound NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- VGQSWFQFSIJTQB-UHFFFAOYSA-N 4-(2-chloroethyl)-1-methyl-3-phenylimidazolidin-2-one Chemical compound O=C1N(C)CC(CCCl)N1C1=CC=CC=C1 VGQSWFQFSIJTQB-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000001530 fumaric acid Substances 0.000 description 6
- 235000011087 fumaric acid Nutrition 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000829 suppository Substances 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- WKNLDUSNHKMIDZ-UHFFFAOYSA-N 4-(2-chloroethyl)-3-(2,6-dimethylphenyl)-1-ethylimidazolidin-2-imine Chemical compound N=C1N(CC)CC(CCCl)N1C1=C(C)C=CC=C1C WKNLDUSNHKMIDZ-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- DXAGEQMSWDHBKV-UHFFFAOYSA-N 4-(2-chloroethyl)-1-methyl-n,3-diphenylimidazolidin-2-imine Chemical compound CN1CC(CCCl)N(C=2C=CC=CC=2)C1=NC1=CC=CC=C1 DXAGEQMSWDHBKV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000001953 Hypotension Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 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
- 230000002218 hypoglycaemic effect Effects 0.000 description 3
- 208000021822 hypotensive Diseases 0.000 description 3
- 230000001077 hypotensive effect Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XFVDFOZIPIDVHV-WLHGVMLRSA-N (e)-but-2-enedioic acid;4-(chloromethyl)-3-phenyl-1-propan-2-ylimidazolidin-2-imine Chemical compound OC(=O)\C=C\C(O)=O.N=C1N(C(C)C)CC(CCl)N1C1=CC=CC=C1 XFVDFOZIPIDVHV-WLHGVMLRSA-N 0.000 description 2
- JFYMNFHQNDQZIP-UHFFFAOYSA-N 1-methyl-n-phenylpyrrolidin-3-amine Chemical compound C1N(C)CCC1NC1=CC=CC=C1 JFYMNFHQNDQZIP-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- RSTASCIIDIDADB-UHFFFAOYSA-N 4-(2-chloroethyl)-1,3-dimethyl-n-phenylimidazolidin-2-imine Chemical compound CN1CC(CCCl)N(C)C1=NC1=CC=CC=C1 RSTASCIIDIDADB-UHFFFAOYSA-N 0.000 description 2
- CCOZWZOJKGPFSF-UHFFFAOYSA-N 4-(2-chloroethyl)-1,3-dimethylimidazolidin-2-one Chemical compound CN1CC(CCCl)N(C)C1=O CCOZWZOJKGPFSF-UHFFFAOYSA-N 0.000 description 2
- SJOBGHXQVLDVNX-UHFFFAOYSA-N 4-(2-chloroethyl)-1-ethyl-3-phenylimidazolidin-2-imine Chemical compound N=C1N(CC)CC(CCCl)N1C1=CC=CC=C1 SJOBGHXQVLDVNX-UHFFFAOYSA-N 0.000 description 2
- MWMMUBZLBZDPBK-UHFFFAOYSA-N 4-(2-chloroethyl)-1-methyl-3-phenylimidazolidin-2-imine Chemical compound N=C1N(C)CC(CCCl)N1C1=CC=CC=C1 MWMMUBZLBZDPBK-UHFFFAOYSA-N 0.000 description 2
- FTAOAUUYCTUKOA-UHFFFAOYSA-N 4-(2-chloroethyl)-3-(2,6-dimethylphenyl)-1-ethylimidazolidin-2-one Chemical compound O=C1N(CC)CC(CCCl)N1C1=C(C)C=CC=C1C FTAOAUUYCTUKOA-UHFFFAOYSA-N 0.000 description 2
- SXHVACXCJMJSBK-UHFFFAOYSA-N 4-(2-chloroethyl)-3-(4-chlorophenyl)-1-ethylimidazolidin-2-imine Chemical compound N=C1N(CC)CC(CCCl)N1C1=CC=C(Cl)C=C1 SXHVACXCJMJSBK-UHFFFAOYSA-N 0.000 description 2
- QNHUGCRSQRVXAD-UHFFFAOYSA-N 4-(chloromethyl)-3-phenyl-1-propan-2-ylimidazolidin-2-imine Chemical compound N=C1N(C(C)C)CC(CCl)N1C1=CC=CC=C1 QNHUGCRSQRVXAD-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- VFXRPXBQCNHQRQ-UHFFFAOYSA-N (alphaR,4R)-Enduracididine Natural products OC(=O)C(N)CC1CNC(=N)N1 VFXRPXBQCNHQRQ-UHFFFAOYSA-N 0.000 description 1
- NMFJQQUKLHGXDP-WLHGVMLRSA-N (e)-but-2-enedioic acid;4-(2-chloroethyl)-1-methyl-n,3-diphenylimidazolidin-2-imine Chemical compound OC(=O)\C=C\C(O)=O.CN1CC(CCCl)N(C=2C=CC=CC=2)C1=NC1=CC=CC=C1 NMFJQQUKLHGXDP-WLHGVMLRSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YCQASTCWGZVWEC-UHFFFAOYSA-N 1,3-diphenylimidazolidin-2-imine Chemical compound N=C1N(C=2C=CC=CC=2)CCN1C1=CC=CC=C1 YCQASTCWGZVWEC-UHFFFAOYSA-N 0.000 description 1
- WYQOIBHSOBQEGT-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-dodecylimidazolidin-2-imine Chemical compound N=C1N(CCCCCCCCCCCC)CCN1C1=CC=C(Cl)C=C1 WYQOIBHSOBQEGT-UHFFFAOYSA-N 0.000 description 1
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical compound ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 1
- OXBBQGGUPKIIAR-UHFFFAOYSA-N 1-methyl-3-phenylimidazolidin-2-imine;hydrochloride Chemical compound Cl.N=C1N(C)CCN1C1=CC=CC=C1 OXBBQGGUPKIIAR-UHFFFAOYSA-N 0.000 description 1
- TVPNGVPSNXPYLT-UHFFFAOYSA-N 1-phenylimidazolidine Chemical compound C1NCCN1C1=CC=CC=C1 TVPNGVPSNXPYLT-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- NAJZQTBFYDUFKU-UHFFFAOYSA-N 2-(1-methyl-3,4-dihydroisoquinolin-2-ium-2-yl)acetamide;chloride Chemical compound [Cl-].C1=CC=C2C(C)=[N+](CC(N)=O)CCC2=C1 NAJZQTBFYDUFKU-UHFFFAOYSA-N 0.000 description 1
- KQOFZNOHOUVLCP-UHFFFAOYSA-N 2-[4-(3-butyl-4-ethyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethanamine Chemical compound N=C1N(CCCC)C(CC)CN1S(=O)(=O)C1=CC=C(CCN)C=C1 KQOFZNOHOUVLCP-UHFFFAOYSA-N 0.000 description 1
- PNHQGHVFLXERHR-UHFFFAOYSA-N 2-methylpyrrolidin-3-ol Chemical compound CC1NCCC1O PNHQGHVFLXERHR-UHFFFAOYSA-N 0.000 description 1
- INHAPBMXVJDDRL-UHFFFAOYSA-N 3-bromo-1-ethylpyrrolidine Chemical compound CCN1CCC(Br)C1 INHAPBMXVJDDRL-UHFFFAOYSA-N 0.000 description 1
- NGNUWMNWKCHSOA-UHFFFAOYSA-N 4-(2-chloroethyl)-1,3-dimethyl-n-phenylimidazolidin-2-amine Chemical compound CN1CC(CCCl)N(C)C1NC1=CC=CC=C1 NGNUWMNWKCHSOA-UHFFFAOYSA-N 0.000 description 1
- PNLIYRMWJZMSQF-UHFFFAOYSA-N 4-(2-chloroethyl)-1-ethyl-3-phenylimidazolidin-2-one Chemical compound O=C1N(CC)CC(CCCl)N1C1=CC=CC=C1 PNLIYRMWJZMSQF-UHFFFAOYSA-N 0.000 description 1
- BXDLYYAMXYAQNN-UHFFFAOYSA-N 4-(2-chloroethyl)-1-methyl-3-phenylimidazolidin-2-imine;hydrochloride Chemical compound Cl.N=C1N(C)CC(CCCl)N1C1=CC=CC=C1 BXDLYYAMXYAQNN-UHFFFAOYSA-N 0.000 description 1
- DMLWSWXRBNVEBJ-UHFFFAOYSA-N 4-(2-chloroethyl)-3-(3-chloro-4-methylphenyl)-1-ethylimidazolidin-2-imine;hydrochloride Chemical compound Cl.N=C1N(CC)CC(CCCl)N1C1=CC=C(C)C(Cl)=C1 DMLWSWXRBNVEBJ-UHFFFAOYSA-N 0.000 description 1
- BUGCYZFIWLSMKB-UHFFFAOYSA-N 4-(2-chloroethyl)-3-(4-chlorophenyl)-1-ethylimidazolidin-2-one Chemical compound O=C1N(CC)CC(CCCl)N1C1=CC=C(Cl)C=C1 BUGCYZFIWLSMKB-UHFFFAOYSA-N 0.000 description 1
- LQSDAZGHUVEHIY-UHFFFAOYSA-N 4-(2-chloroethyl)-n,1-dimethyl-3-phenylimidazolidin-2-imine Chemical class CN=C1N(C)CC(CCCl)N1C1=CC=CC=C1 LQSDAZGHUVEHIY-UHFFFAOYSA-N 0.000 description 1
- JXZYCWZPWQKZJQ-UHFFFAOYSA-N 4-(2-chloroethyl)-n-(2,6-dimethylphenyl)-1-methyl-3-phenylimidazolidin-2-imine Chemical compound CN1CC(CCCl)N(C=2C=CC=CC=2)C1=NC1=C(C)C=CC=C1C JXZYCWZPWQKZJQ-UHFFFAOYSA-N 0.000 description 1
- LUJOEMSFAVYBJL-UHFFFAOYSA-N 4-(chloromethyl)-3-phenyl-1-propan-2-ylimidazolidin-2-one Chemical compound O=C1N(C(C)C)CC(CCl)N1C1=CC=CC=C1 LUJOEMSFAVYBJL-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- JUESIEZYKOTNPZ-UHFFFAOYSA-N 5-(2-chloroethyl)-2-(2,6-dichlorophenyl)-1,3-dimethylimidazolidin-4-imine Chemical compound ClCCC1N(C(N(C1=N)C)C1=C(C=CC=C1Cl)Cl)C JUESIEZYKOTNPZ-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- DAUVCDGQCDFSSC-VQYXCCSOSA-N C(\C=C\C(=O)O)(=O)O.ClCCC1N(C(N(C1)C)=NC1=C(C=CC=C1Cl)Cl)C.C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.ClCCC1N(C(N(C1)C)=NC1=C(C=CC=C1Cl)Cl)C Chemical compound C(\C=C\C(=O)O)(=O)O.ClCCC1N(C(N(C1)C)=NC1=C(C=CC=C1Cl)Cl)C.C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.ClCCC1N(C(N(C1)C)=NC1=C(C=CC=C1Cl)Cl)C DAUVCDGQCDFSSC-VQYXCCSOSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- VFXRPXBQCNHQRQ-DMTCNVIQSA-N L-enduracididine Chemical compound OC(=O)[C@@H](N)C[C@@H]1CNC(=N)N1 VFXRPXBQCNHQRQ-DMTCNVIQSA-N 0.000 description 1
- CFAHWCVTQHFQAE-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-1-ethylpyrrolidin-2-amine Chemical compound CCN1CCCC1NC1=C(C)C=CC=C1C CFAHWCVTQHFQAE-UHFFFAOYSA-N 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 208000002151 Pleural effusion Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- SYOIWFNFUFXXMV-UHFFFAOYSA-N [Br].Cl Chemical compound [Br].Cl SYOIWFNFUFXXMV-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- HBFXVTVOSLPOEY-UHFFFAOYSA-N ethoxyethane;2-propan-2-yloxypropane Chemical compound CCOCC.CC(C)OC(C)C HBFXVTVOSLPOEY-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 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
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- WKODSOXTLGPOBN-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-ethylpyrrolidin-3-amine Chemical compound C1N(CC)CCC1NC1=C(C)C=CC=C1C WKODSOXTLGPOBN-UHFFFAOYSA-N 0.000 description 1
- GQJKEPSPZXMLAD-UHFFFAOYSA-N n-phenyl-1-propan-2-ylazetidin-3-amine Chemical compound C1N(C(C)C)CC1NC1=CC=CC=C1 GQJKEPSPZXMLAD-UHFFFAOYSA-N 0.000 description 1
- 239000000133 nasal decongestant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- GPAHSCXZHOZPEZ-UHFFFAOYSA-N oxalic acid;(1-propan-2-ylazetidin-3-yl) methanesulfonate Chemical compound OC(=O)C(O)=O.CC(C)N1CC(OS(C)(=O)=O)C1 GPAHSCXZHOZPEZ-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation 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
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/009,899 US4247705A (en) | 1979-02-06 | 1979-02-06 | 4-Substituted 2-iminoimidazolidine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3004348A1 DE3004348A1 (de) | 1980-08-14 |
| DE3004348C2 true DE3004348C2 (en, 2012) | 1990-10-25 |
Family
ID=21740366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803004348 Granted DE3004348A1 (de) | 1979-02-06 | 1980-02-06 | In 4-stellung substituierte 2- iminoimidazolidinverbindungen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4247705A (en, 2012) |
| JP (1) | JPS55113769A (en, 2012) |
| CA (1) | CA1140126A (en, 2012) |
| CH (1) | CH645357A5 (en, 2012) |
| DE (1) | DE3004348A1 (en, 2012) |
| FR (1) | FR2448534A1 (en, 2012) |
| GB (1) | GB2043060B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4647557A (en) * | 1982-12-28 | 1987-03-03 | Gerard Moinet | Novel heterocyclic derivatives bearing an amino radical, processes for their production and the pharmaceutical compositions containing them |
| JPS6038380A (ja) * | 1983-08-11 | 1985-02-27 | Shionogi & Co Ltd | １−ピペリジニル−１，４−ベンゾジアゼピン類の改良合成法 |
| JPH0717621B2 (ja) * | 1986-03-07 | 1995-03-01 | 日本バイエルアグロケム株式会社 | 新規ヘテロ環式化合物 |
| USRE39130E1 (en) | 1986-03-07 | 2006-06-13 | Bayer Cropscience K.K. | Heterocyclic compounds |
| GB8903592D0 (en) * | 1989-02-16 | 1989-04-05 | Boots Co Plc | Therapeutic agents |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3147270A (en) * | 1961-11-03 | 1964-09-01 | Warner Lambert Pharmaceutical | Substituted 2-imidazolines |
| US3337580A (en) * | 1964-12-31 | 1967-08-22 | Robins Co Inc A H | 1-hydrocarbon-3 aryl-4-substituted ethyl-2-imidazolidinones |
| GB1305548A (en, 2012) * | 1969-10-29 | 1973-02-07 | ||
| GB1474671A (en) * | 1975-01-15 | 1977-05-25 | Lepetit Spa | Preparation of 2-aminoimidazole derivatives |
| GB1570213A (en) * | 1975-10-29 | 1980-06-25 | Smithkline Corp | Imidazoles |
-
1979
- 1979-02-06 US US06/009,899 patent/US4247705A/en not_active Expired - Lifetime
-
1980
- 1980-02-05 FR FR8002489A patent/FR2448534A1/fr active Granted
- 1980-02-05 CH CH92680A patent/CH645357A5/fr not_active IP Right Cessation
- 1980-02-05 CA CA000345056A patent/CA1140126A/en not_active Expired
- 1980-02-06 JP JP1347780A patent/JPS55113769A/ja active Granted
- 1980-02-06 DE DE19803004348 patent/DE3004348A1/de active Granted
- 1980-02-06 GB GB8003967A patent/GB2043060B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3004348A1 (de) | 1980-08-14 |
| CA1140126A (en) | 1983-01-25 |
| FR2448534B1 (en, 2012) | 1983-03-25 |
| GB2043060B (en) | 1983-03-09 |
| JPS55113769A (en) | 1980-09-02 |
| GB2043060A (en) | 1980-10-01 |
| US4247705A (en) | 1981-01-27 |
| FR2448534A1 (fr) | 1980-09-05 |
| CH645357A5 (fr) | 1984-09-28 |
| JPS6410512B2 (en, 2012) | 1989-02-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. |
|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07D233/44 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |