CA1140126A - 4-substituted 2-iminoimidazolidine compounds - Google Patents
4-substituted 2-iminoimidazolidine compoundsInfo
- Publication number
- CA1140126A CA1140126A CA000345056A CA345056A CA1140126A CA 1140126 A CA1140126 A CA 1140126A CA 000345056 A CA000345056 A CA 000345056A CA 345056 A CA345056 A CA 345056A CA 1140126 A CA1140126 A CA 1140126A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- ethyl
- phenyl
- chloroethyl
- group
- 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
Links
- -1 4-substituted 2-iminoimidazolidine Chemical class 0.000 title claims abstract description 45
- 150000001875 compounds Chemical class 0.000 title claims description 14
- 238000000034 method Methods 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 44
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 41
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 29
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 29
- 239000000047 product Substances 0.000 claims description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 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 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Chemical group 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 10
- 239000001530 fumaric acid Substances 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 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 claims description 7
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 7
- 229910000831 Steel Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000010959 steel Substances 0.000 claims description 7
- 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 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 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 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- SFKYJBYNNJVICZ-UHFFFAOYSA-N 2-(1-ethyl-2-imino-3-phenylimidazolidin-4-yl)ethanamine Chemical compound N=C1N(CC)CC(CCN)N1C1=CC=CC=C1 SFKYJBYNNJVICZ-UHFFFAOYSA-N 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 4
- CCOZWZOJKGPFSF-UHFFFAOYSA-N 4-(2-chloroethyl)-1,3-dimethylimidazolidin-2-one Chemical compound CN1CC(CCCl)N(C)C1=O CCOZWZOJKGPFSF-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 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 claims description 4
- 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 4
- 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 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 claims description 3
- 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 description 3
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- PTJAQAXCBWHLNZ-UHFFFAOYSA-N n,n-dibenzyl-2-(1-ethyl-2-imino-3-phenylimidazolidin-4-yl)ethanamine Chemical compound C=1C=CC=CC=1N1C(=N)N(CC)CC1CCN(CC=1C=CC=CC=1)CC1=CC=CC=C1 PTJAQAXCBWHLNZ-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 2
- IRIAXGKAUMAIAC-UHFFFAOYSA-N 4-(2-chloroethyl)-1,3-dimethylimidazolidin-2-imine;hydrochloride Chemical compound Cl.CN1CC(CCCl)N(C)C1=N IRIAXGKAUMAIAC-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 19
- 150000002431 hydrogen Chemical group 0.000 claims 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
- 150000001412 amines Chemical class 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 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
- OMPXTQYWYRWWPH-UHFFFAOYSA-N 4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1NCCC(C=2C=CC=CC=2)=C1 OMPXTQYWYRWWPH-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 230000000875 corresponding effect Effects 0.000 claims 1
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 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 claims 1
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 abstract description 11
- 208000002177 Cataract Diseases 0.000 abstract description 5
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 4
- 230000001077 hypotensive effect Effects 0.000 abstract description 4
- 208000001953 Hypotension Diseases 0.000 abstract description 3
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 3
- 208000021822 hypotensive Diseases 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- LHAKXHSUYDNBLA-WLHGVMLRSA-N (e)-but-2-enedioic acid;4-(2-chloroethyl)-n,1-dimethyl-3-phenylimidazolidin-2-imine Chemical compound OC(=O)\C=C\C(O)=O.CN=C1N(C)CC(CCCl)N1C1=CC=CC=C1 LHAKXHSUYDNBLA-WLHGVMLRSA-N 0.000 abstract description 2
- 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 abstract description 2
- 241001465754 Metazoa Species 0.000 abstract description 2
- 208000002151 Pleural effusion Diseases 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 239000008103 glucose Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 65
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 229960001701 chloroform Drugs 0.000 description 32
- 238000002360 preparation method Methods 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- 239000002253 acid Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 238000007792 addition Methods 0.000 description 16
- 239000010410 layer Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 9
- 125000005037 alkyl phenyl group Chemical group 0.000 description 8
- 230000002401 inhibitory effect Effects 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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
- 206010020772 Hypertension Diseases 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-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
- 206010003119 arrhythmia Diseases 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 201000001421 hyperglycemia Diseases 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-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
- 239000007853 buffer solution Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 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
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 150000008625 2-imidazolidinones Chemical class 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 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
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 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
- 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
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 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
- 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 description 1
- 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 1
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical compound ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 1
- FLVFPAIGVBQGET-UHFFFAOYSA-N 1-methylpyrrolidin-3-ol Chemical compound CN1CCC(O)C1 FLVFPAIGVBQGET-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
- KDZRJYPIZKUTJV-UHFFFAOYSA-N 2-(1-ethyl-2-imino-3-phenylimidazolidin-4-yl)ethanamine;dihydrochloride Chemical compound Cl.Cl.N=C1N(CC)CC(CCN)N1C1=CC=CC=C1 KDZRJYPIZKUTJV-UHFFFAOYSA-N 0.000 description 1
- PBOTYKVXJBUXLG-UHFFFAOYSA-N 2-(2-imino-1,3-dimethylimidazolidin-4-yl)-n,n-dimethylethanamine;hydrate;dihydrochloride Chemical compound O.Cl.Cl.CN(C)CCC1CN(C)C(=N)N1C PBOTYKVXJBUXLG-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
- 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
- GMWJPJIIDMAICH-UHFFFAOYSA-N 4-(2-chloroethyl)-3-(2,6-dimethylphenyl)-1-ethylimidazolidin-2-imine;hydrochloride Chemical compound Cl.N=C1N(CC)CC(CCCl)N1C1=C(C)C=CC=C1C GMWJPJIIDMAICH-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- URVVFIAUKSGYOG-UHFFFAOYSA-N 4-methylpentan-2-one;propan-2-ol Chemical compound CC(C)O.CC(C)CC(C)=O URVVFIAUKSGYOG-UHFFFAOYSA-N 0.000 description 1
- POGWXTJNUCZEPR-UHFFFAOYSA-N 4-phenyl-1,2,3,6-tetrahydropyridin-1-ium;chloride Chemical compound Cl.C1NCCC(C=2C=CC=CC=2)=C1 POGWXTJNUCZEPR-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101100218970 Drosophila melanogaster borr gene Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-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
- 235000019759 Maize starch Nutrition 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 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
- 239000008120 corn starch Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- JKXCZYCVHPKTPK-UHFFFAOYSA-N hydrate;trihydrochloride Chemical compound O.Cl.Cl.Cl JKXCZYCVHPKTPK-UHFFFAOYSA-N 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- DBDWEKIVKGVZEL-UHFFFAOYSA-N imidazolidine dihydrochloride Chemical compound Cl.Cl.N1CNCC1 DBDWEKIVKGVZEL-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 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
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FKUMJALECWJITA-UHFFFAOYSA-N n,n-dibenzyl-2-(1-ethyl-2-imino-3-phenylimidazolidin-4-yl)ethanamine;hydrate;dihydrochloride Chemical compound O.Cl.Cl.C=1C=CC=CC=1N1C(=N)N(CC)CC1CCN(CC=1C=CC=CC=1)CC1=CC=CC=C1 FKUMJALECWJITA-UHFFFAOYSA-N 0.000 description 1
- AANGXLPFULSGFO-UHFFFAOYSA-N n,n-dibenzyl-2-(1-ethyl-2-imino-3-phenylimidazolidin-4-yl)ethanamine;hydrate;hydrochloride Chemical compound O.Cl.C=1C=CC=CC=1N1C(=N)N(CC)CC1CCN(CC=1C=CC=CC=1)CC1=CC=CC=C1 AANGXLPFULSGFO-UHFFFAOYSA-N 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
- 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
- VXZHLBASORYUDT-UHFFFAOYSA-N n-phenyl-1-propan-2-ylazetidin-3-amine;hydrochloride Chemical compound Cl.C1N(C(C)C)CC1NC1=CC=CC=C1 VXZHLBASORYUDT-UHFFFAOYSA-N 0.000 description 1
- 239000000133 nasal decongestant Substances 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
- HQWQOLKOXCEWEX-UHFFFAOYSA-N oxalic acid;(1-propan-2-ylazetidin-3-yl)methanesulfonic acid Chemical compound OC(=O)C(O)=O.CC(C)N1CC(CS(O)(=O)=O)C1 HQWQOLKOXCEWEX-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 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
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 125000005624 silicic acid group Chemical class 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
- 239000002511 suppository base Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9,899 | 1979-02-06 | ||
| US06/009,899 US4247705A (en) | 1979-02-06 | 1979-02-06 | 4-Substituted 2-iminoimidazolidine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1140126A true CA1140126A (en) | 1983-01-25 |
Family
ID=21740366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000345056A Expired CA1140126A (en) | 1979-02-06 | 1980-02-05 | 4-substituted 2-iminoimidazolidine compounds |
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 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3780040A (en) | 2-substituted-3,4-dihydroquinazolines | |
| CA1175432A (en) | N-oxacyclyl-alkylpiperidine derivatives, process for their preparation, pharmaceutical products containing them, and their use | |
| US5073671A (en) | 1-(benzyl or pyridylmethyl)-4 or 5-aminomethyl-pyrrolidin-2-ones | |
| NO155805B (no) | Analogifremgangsmaate for fremstilling av terapeutisk virksomme 2-(4-(difenylmethyl)-1-piperazinyl)-eddiksyrer og deres amider og ikke-toksiske salter. | |
| NZ241928A (en) | Various diaza ,triaza and thiaza heterocyclic derivatives and pharmaceutical compositions | |
| US4140793A (en) | Guanidine derivatives | |
| HUT73656A (en) | Acetamides, pharmaceutical compositions containing them and process for their preparation | |
| CA1140126A (en) | 4-substituted 2-iminoimidazolidine compounds | |
| US3364220A (en) | Heterocyclicaminoalkylguanidines | |
| US6255327B1 (en) | Diphenyl-substituted heterocycles, processes for preparing them and their use as pharmaceutical compositions | |
| JPH0226629B2 (en, 2012) | ||
| US3752810A (en) | Substituted n aminoalkyl arylamino imidazolines-(2) | |
| US3314963A (en) | Azabenzocycloalkane-n-carboxamidines | |
| AU636577B2 (en) | Heterocyclic acetylenic amines having central nervous system activity | |
| IE44792B1 (en) | Heterocyclic derivatives of guanidine | |
| US4080503A (en) | 2-Amino-4-phenyl-2-imidazolines and salts thereof | |
| US4327107A (en) | Method useful in the treatment of sugar cataracts using 4-substituted-2-iminoimidazolidine compounds | |
| HU176110B (en) | Process for producing thiourea- and guanidine derivatives | |
| US3247222A (en) | Alpha (nu-hydrocarbonpyrrolidyl-3-) alpha, alpha carbocyclic arylacetamides | |
| US3822262A (en) | Phenyl acetylimino-imidazolines and-hexahydropyrimidines | |
| GB2044756A (en) | Fluoro-amines processes for their preparation and pharmaceutical compositions containing them | |
| US4835172A (en) | Novel benzamides, intermediates and process for the preparation and therapeutic use thereof | |
| US4539323A (en) | N-[1-(4-Amino-6,7-dialkoxy-2-quinazolinyl)-4-piperidyl]-oxazolidine-2,4-diones | |
| US4608375A (en) | Quinazolinone derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same | |
| US4113868A (en) | 5,6-dihydropyrimidin-4(3h)one derivatives, and antiedema compositions and methods employing them |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |