DE3004348A1 - In 4-stellung substituierte 2- iminoimidazolidinverbindungen - Google Patents
In 4-stellung substituierte 2- iminoimidazolidinverbindungenInfo
- Publication number
- DE3004348A1 DE3004348A1 DE19803004348 DE3004348A DE3004348A1 DE 3004348 A1 DE3004348 A1 DE 3004348A1 DE 19803004348 DE19803004348 DE 19803004348 DE 3004348 A DE3004348 A DE 3004348A DE 3004348 A1 DE3004348 A1 DE 3004348A1
- Authority
- DE
- Germany
- Prior art keywords
- acid addition
- ethyl
- chloroethyl
- compound
- iminoimidazolidine
- 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.)
- Granted
Links
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 title claims description 16
- 150000003839 salts Chemical class 0.000 claims description 82
- 239000002253 acid Substances 0.000 claims description 59
- -1 dimethylphenyl Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 238000002360 preparation method Methods 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 32
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 16
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 16
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 208000002177 Cataract Diseases 0.000 claims description 6
- 206010003119 arrhythmia Diseases 0.000 claims description 6
- 125000003106 haloaryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 201000001421 hyperglycemia Diseases 0.000 claims description 6
- 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 claims description 5
- LQSDAZGHUVEHIY-UHFFFAOYSA-N 4-(2-chloroethyl)-n,1-dimethyl-3-phenylimidazolidin-2-imine Chemical compound CN=C1N(C)CC(CCCl)N1C1=CC=CC=C1 LQSDAZGHUVEHIY-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 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 claims description 4
- 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 claims description 4
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- SBOCMJDWTNQNCH-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-1-ethyl-2-iminoimidazolidin-4-yl]-n,n-dimethylethanamine Chemical compound N=C1N(CC)CC(CCN(C)C)N1C1=CC=C(Cl)C=C1 SBOCMJDWTNQNCH-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 3
- TVPNGVPSNXPYLT-UHFFFAOYSA-N 1-phenylimidazolidine Chemical compound C1NCCN1C1=CC=CC=C1 TVPNGVPSNXPYLT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- LUNZGIKWJMQUIY-UHFFFAOYSA-N 4-(2-chloroethyl)-3-(3-chloro-4-methylphenyl)-1-ethylimidazolidin-2-imine Chemical compound N=C1N(CC)CC(CCCl)N1C1=CC=C(C)C(Cl)=C1 LUNZGIKWJMQUIY-UHFFFAOYSA-N 0.000 claims 2
- WQWXVJVAHDADJV-UHFFFAOYSA-N 4-(2-chloroethyl)-n-(2,6-dichlorophenyl)-1,3-dimethylimidazolidin-2-imine Chemical compound CN1CC(CCCl)N(C)C1=NC1=C(Cl)C=CC=C1Cl WQWXVJVAHDADJV-UHFFFAOYSA-N 0.000 claims 2
- OPYRWYZJFVUGKG-UHFFFAOYSA-N 2-(2-imino-1,3-dimethylimidazolidin-4-yl)-n,n-dimethylethanamine Chemical compound CN(C)CCC1CN(C)C(=N)N1C OPYRWYZJFVUGKG-UHFFFAOYSA-N 0.000 claims 1
- WPLKLBQPUOMBBA-UHFFFAOYSA-N 4-(2-chloroethyl)-1,3-dimethyl-n-propan-2-ylimidazolidin-2-imine Chemical compound CC(C)N=C1N(C)CC(CCCl)N1C WPLKLBQPUOMBBA-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 claims 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 claims 1
- 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 claims 1
- XAUMJIZLWBZJDR-UHFFFAOYSA-N 4-[2-(dimethylamino)ethyl]-1-ethyl-3-phenylimidazolidin-2-amine Chemical compound NC1N(CC)CC(CCN(C)C)N1C1=CC=CC=C1 XAUMJIZLWBZJDR-UHFFFAOYSA-N 0.000 claims 1
- 241000287433 Turdus Species 0.000 claims 1
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 95
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 41
- 229910052757 nitrogen Inorganic materials 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000010410 layer Substances 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 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
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 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
- 238000009835 boiling Methods 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 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 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 4
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 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
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-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
- 239000013078 crystal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000002218 hypoglycaemic effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- DVIXNULIBRLERQ-UHFFFAOYSA-N 2-(1-ethyl-2-imino-3-phenylimidazolidin-4-yl)-n,n-dimethylethanamine Chemical compound N=C1N(CC)CC(CCN(C)C)N1C1=CC=CC=C1 DVIXNULIBRLERQ-UHFFFAOYSA-N 0.000 description 2
- 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 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 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 229910052794 bromium Inorganic materials 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
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 238000007918 intramuscular administration Methods 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
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 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
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- AVLKYCMLUHXGOX-UHFFFAOYSA-N (1-methylpyrrolidin-3-yl) 4-methylbenzenesulfonate Chemical compound C1N(C)CCC1OS(=O)(=O)C1=CC=C(C)C=C1 AVLKYCMLUHXGOX-UHFFFAOYSA-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
- VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 229920001592 potato starch Polymers 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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Classifications
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- 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 true DE3004348A1 (de) | 1980-08-14 |
| DE3004348C2 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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0135079A1 (en) * | 1983-08-11 | 1985-03-27 | Shionogi & Co., Ltd. | Process for preparing 1-substituted-1,4-benzodiazepine derivatives |
Families Citing this family (4)
| 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 |
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3337580A (en) * | 1964-12-31 | 1967-08-22 | Robins Co Inc A H | 1-hydrocarbon-3 aryl-4-substituted ethyl-2-imidazolidinones |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3147270A (en) * | 1961-11-03 | 1964-09-01 | Warner Lambert Pharmaceutical | Substituted 2-imidazolines |
| 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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3337580A (en) * | 1964-12-31 | 1967-08-22 | Robins Co Inc A H | 1-hydrocarbon-3 aryl-4-substituted ethyl-2-imidazolidinones |
Non-Patent Citations (1)
| Title |
|---|
| J. Antibiotics 21, S. 665, 1968 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0135079A1 (en) * | 1983-08-11 | 1985-03-27 | Shionogi & Co., Ltd. | Process for preparing 1-substituted-1,4-benzodiazepine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| 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 |
| DE3004348C2 (en, 2012) | 1990-10-25 |
| JPS6410512B2 (en, 2012) | 1989-02-22 |
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| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
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