CA1099274A - 1-acyl-2-imidazolines and their manufacture - Google Patents
1-acyl-2-imidazolines and their manufactureInfo
- Publication number
- CA1099274A CA1099274A CA290,841A CA290841A CA1099274A CA 1099274 A CA1099274 A CA 1099274A CA 290841 A CA290841 A CA 290841A CA 1099274 A CA1099274 A CA 1099274A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- imidazoline
- indanylamino
- alkyl
- alkoxy
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 76
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000002541 furyl group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 5
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- RXTJLDXSGNEJIT-UHFFFAOYSA-N 2,3-dihydro-1h-inden-4-amine Chemical compound NC1=CC=CC2=C1CCC2 RXTJLDXSGNEJIT-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical group 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- WGCQZEQXKNFPJL-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound CC(=O)N1CCN=C1NC1=CC=CC2=C1CCC2 WGCQZEQXKNFPJL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- JJWACYUTERPMBM-UHFFFAOYSA-N 1-acetylimidazolidin-2-one Chemical compound CC(=O)N1CCNC1=O JJWACYUTERPMBM-UHFFFAOYSA-N 0.000 claims description 3
- IUVCBSZCGJAZNU-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-phenylmethanone Chemical compound C1CN=C(NC=2C=3CCCC=3C=CC=2)N1C(=O)C1=CC=CC=C1 IUVCBSZCGJAZNU-UHFFFAOYSA-N 0.000 claims description 3
- SODWJACROGQSMM-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-amine Chemical compound C1CCCC2=C1C=CC=C2N SODWJACROGQSMM-UHFFFAOYSA-N 0.000 claims description 2
- JGTRKYPDNSKJAT-UHFFFAOYSA-N 1-[2-(5,6,7,8-tetrahydronaphthalen-1-ylamino)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound CC(=O)N1CCN=C1NC1=CC=CC2=C1CCCC2 JGTRKYPDNSKJAT-UHFFFAOYSA-N 0.000 claims 2
- IRLMWBRTASRHRA-UHFFFAOYSA-N ethyl 2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazole-1-carboxylate Chemical compound CCOC(=O)N1CCN=C1NC1=CC=CC2=C1CCC2 IRLMWBRTASRHRA-UHFFFAOYSA-N 0.000 claims 2
- AJSFBSYWKIBTGP-UHFFFAOYSA-N 1-benzoylimidazolidin-2-one Chemical compound C=1C=CC=CC=1C(=O)N1CCNC1=O AJSFBSYWKIBTGP-UHFFFAOYSA-N 0.000 claims 1
- KQYZBMSXJXAYGB-UHFFFAOYSA-N ethyl 2-oxoimidazolidine-1-carboxylate Chemical compound CCOC(=O)N1CCNC1=O KQYZBMSXJXAYGB-UHFFFAOYSA-N 0.000 claims 1
- -1 aralkoxy Chemical group 0.000 abstract description 96
- 239000000543 intermediate Substances 0.000 abstract description 5
- 150000002462 imidazolines Chemical class 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 238000002844 melting Methods 0.000 description 92
- 230000008018 melting Effects 0.000 description 92
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 229940060038 chlorine Drugs 0.000 description 9
- 235000017168 chlorine Nutrition 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 6
- 238000005947 deacylation reaction Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- CNKLAMCYSQDBMF-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-4-yl)-4,5-dihydro-1h-imidazol-2-amine;nitric acid Chemical compound O[N+]([O-])=O.C=12CCCC2=CC=CC=1NC1=NCCN1 CNKLAMCYSQDBMF-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 229940083608 sodium hydroxide Drugs 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000020176 deacylation Effects 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 125000004799 bromophenyl group Chemical group 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000006286 dichlorobenzyl group Chemical group 0.000 description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000006178 methyl benzyl group Chemical group 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000001701 trimethoxybenzyl group Chemical group 0.000 description 2
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 2
- HVOIBJIZVCTNBU-UHFFFAOYSA-N (2-chlorophenyl)-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]methanone Chemical compound ClC1=CC=CC=C1C(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 HVOIBJIZVCTNBU-UHFFFAOYSA-N 0.000 description 1
- BAVSZWOUMBOTDF-UHFFFAOYSA-N (2-methylphenyl)-[2-(5,6,7,8-tetrahydronaphthalen-1-ylamino)-4,5-dihydroimidazol-1-yl]methanone Chemical compound CC1=CC=CC=C1C(=O)N1C(NC=2C=3CCCCC=3C=CC=2)=NCC1 BAVSZWOUMBOTDF-UHFFFAOYSA-N 0.000 description 1
- ANAIBKKITGENBW-UHFFFAOYSA-N (3-chlorophenyl)-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]methanone Chemical compound ClC1=CC=CC(C(=O)N2C(=NCC2)NC=2C=3CCCC=3C=CC=2)=C1 ANAIBKKITGENBW-UHFFFAOYSA-N 0.000 description 1
- YOLPDJLHLIZAQT-UHFFFAOYSA-N (4-chlorophenyl)-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 YOLPDJLHLIZAQT-UHFFFAOYSA-N 0.000 description 1
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 1
- AGVNXDKOXUZDCG-UHFFFAOYSA-N 1-(2,3,4-trimethoxybenzoyl)imidazolidin-2-one Chemical compound COC1=C(OC)C(OC)=CC=C1C(=O)N1C(=O)NCC1 AGVNXDKOXUZDCG-UHFFFAOYSA-N 0.000 description 1
- CUQCXQOZSAXIQM-UHFFFAOYSA-N 1-(2,6-dichlorobenzoyl)imidazolidin-2-one Chemical compound ClC1=CC=CC(Cl)=C1C(=O)N1C(=O)NCC1 CUQCXQOZSAXIQM-UHFFFAOYSA-N 0.000 description 1
- BCMPZCCYMHMPTB-UHFFFAOYSA-N 1-(3,4,5-trimethoxybenzoyl)imidazolidin-2-one Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2C(NCC2)=O)=C1 BCMPZCCYMHMPTB-UHFFFAOYSA-N 0.000 description 1
- BTROLKJFQYVFFC-UHFFFAOYSA-N 1-(3-chlorobenzoyl)imidazolidin-2-one Chemical compound ClC1=CC=CC(C(=O)N2C(NCC2)=O)=C1 BTROLKJFQYVFFC-UHFFFAOYSA-N 0.000 description 1
- QENPVUYGZNUWMZ-UHFFFAOYSA-N 1-(4-phenylbenzoyl)imidazolidin-2-one Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)N1CCNC1=O QENPVUYGZNUWMZ-UHFFFAOYSA-N 0.000 description 1
- LWORQQGRFOICPY-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-2,2,2-trifluoroethanone Chemical compound FC(F)(F)C(=O)N1CCN=C1NC1=CC=CC2=C1CCC2 LWORQQGRFOICPY-UHFFFAOYSA-N 0.000 description 1
- JFZMCJQPJYUQSG-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-2-(3,4,5-trimethoxyphenyl)ethanone Chemical compound COC1=C(OC)C(OC)=CC(CC(=O)N2C(=NCC2)NC=2C=3CCCC=3C=CC=2)=C1 JFZMCJQPJYUQSG-UHFFFAOYSA-N 0.000 description 1
- UVBDUZIFCYSXTR-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-2-phenylpropan-1-one Chemical compound C1CN=C(NC=2C=3CCCC=3C=CC=2)N1C(=O)C(C)C1=CC=CC=C1 UVBDUZIFCYSXTR-UHFFFAOYSA-N 0.000 description 1
- AWLLDAACSOTQPU-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-2-pyridin-3-ylethanone Chemical compound C1CN=C(NC=2C=3CCCC=3C=CC=2)N1C(=O)CC1=CC=CN=C1 AWLLDAACSOTQPU-UHFFFAOYSA-N 0.000 description 1
- LLVZFCBOCKPYNL-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-3-(4-methoxyphenyl)propan-1-one Chemical compound C1=CC(OC)=CC=C1CCC(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 LLVZFCBOCKPYNL-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RHAAGWRBIVCBSY-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine;hydron;chloride Chemical compound Cl.C1=CC=C2C(N)CCC2=C1 RHAAGWRBIVCBSY-UHFFFAOYSA-N 0.000 description 1
- IOCVBFVOZROKLS-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound C=1C=C2OCOC2=CC=1CC(=O)N1CCN=C1NC1=CC=CC2=C1CCC2 IOCVBFVOZROKLS-UHFFFAOYSA-N 0.000 description 1
- ZCJHYTNJYKAIGH-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1-[2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound ClC1=CC=CC(Cl)=C1CC(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 ZCJHYTNJYKAIGH-UHFFFAOYSA-N 0.000 description 1
- 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- SSORSZACHCNXSJ-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)-3-[2-(2-hydroxypropylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound ClC=1C=C(C=CC=1Cl)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NCC(C)O SSORSZACHCNXSJ-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- AFPBRQHNWWNEEH-UHFFFAOYSA-N 2-ethylhexyl 2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazole-1-carboxylate Chemical compound CCCCC(CC)COC(=O)N1CCN=C1NC1=CC=CC2=C1CCC2 AFPBRQHNWWNEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 1
- ZHTHFRIQYSIAOF-UHFFFAOYSA-N 4,5-dihydro-1h-imidazole;nitric acid Chemical class O[N+]([O-])=O.C1CN=CN1 ZHTHFRIQYSIAOF-UHFFFAOYSA-N 0.000 description 1
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 101100108327 Escherichia coli (strain K12) melA gene Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- STWPQMMPUXKPIY-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-1-ylamino)-4,5-dihydroimidazol-1-yl]-phenylmethanone Chemical compound C1CN=C(NC2C3=CC=CC=C3CC2)N1C(=O)C1=CC=CC=C1 STWPQMMPUXKPIY-UHFFFAOYSA-N 0.000 description 1
- JJQRWMWYRWXDSM-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 JJQRWMWYRWXDSM-UHFFFAOYSA-N 0.000 description 1
- QTBGVZFJMILCDW-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 QTBGVZFJMILCDW-UHFFFAOYSA-N 0.000 description 1
- FGLMURQEDOUHJV-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 FGLMURQEDOUHJV-UHFFFAOYSA-N 0.000 description 1
- HMICUWKCNORKJL-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(NC=2C=3CCCC=3C=CC=2)=NCC1 HMICUWKCNORKJL-UHFFFAOYSA-N 0.000 description 1
- NYZPSWXWABTAMR-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-thiophen-2-ylmethanone Chemical compound C1CN=C(NC=2C=3CCCC=3C=CC=2)N1C(=O)C1=CC=CS1 NYZPSWXWABTAMR-UHFFFAOYSA-N 0.000 description 1
- KBODNIKXSKBWPP-UHFFFAOYSA-N [2-(2,3-dihydro-1h-inden-4-ylamino)-4,5-dihydroimidazol-1-yl]-thiophen-3-ylmethanone Chemical compound C1CN=C(NC=2C=3CCCC=3C=CC=2)N1C(=O)C=1C=CSC=1 KBODNIKXSKBWPP-UHFFFAOYSA-N 0.000 description 1
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 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
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- KUCWWEPJRBANHL-UHFFFAOYSA-N indanazoline Chemical compound C=12CCCC2=CC=CC=1NC1=NCCN1 KUCWWEPJRBANHL-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 125000006372 monohalo methyl group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 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
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2652004A DE2652004C3 (de) | 1976-11-15 | 1976-11-15 | l-Acyl-2-arylamino-2-imidazoline, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DEP2652004.7 | 1976-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1099274A true CA1099274A (en) | 1981-04-14 |
Family
ID=5993186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA290,841A Expired CA1099274A (en) | 1976-11-15 | 1977-11-14 | 1-acyl-2-imidazolines and their manufacture |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4269990A (OSRAM) |
| AT (1) | AT362786B (OSRAM) |
| CA (1) | CA1099274A (OSRAM) |
| CH (1) | CH633274A5 (OSRAM) |
| DE (1) | DE2652004C3 (OSRAM) |
| FR (1) | FR2370736A1 (OSRAM) |
| GB (1) | GB1591879A (OSRAM) |
| NL (1) | NL7712149A (OSRAM) |
| SE (2) | SE441923B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3011327A1 (de) * | 1980-03-24 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | 1-aroyl-2-phenylamino-2-imidazoline, ihre herstellung und verwendung |
| US6670364B2 (en) * | 2001-01-31 | 2003-12-30 | Telik, Inc. | Antagonists of MCP-1 function and methods of use thereof |
| US6962926B2 (en) * | 2001-01-31 | 2005-11-08 | Telik, Inc. | Antagonist of MCP-1 function, and compositions and methods of use thereof |
| TWI245761B (en) | 2001-03-01 | 2005-12-21 | Telik Inc | Antagonists of MCP-1 function and methods of use thereof |
| TWI236474B (en) * | 2001-04-03 | 2005-07-21 | Telik Inc | Antagonists of MCP-1 function and methods of use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3288805A (en) * | 1966-11-29 | Amino-eviid azoline | ||
| US3636219A (en) * | 1964-03-02 | 1972-01-18 | Du Pont | Anticholinergic compositions containing certain thiazolines or imidazolines |
| CH488188A (de) * | 1968-11-08 | 1970-03-31 | Zellweger Uster Ag | Fadenklemme für Fadenprüfmaschinen |
| BE741947A (en) | 1969-11-19 | 1970-05-04 | N-acyl-2-arylamino-imidazoline | |
| DE2316377C3 (de) * | 1973-04-02 | 1978-11-02 | Lentia Gmbh, Chem. U. Pharm. Erzeugnisse - Industriebedarf, 8000 Muenchen | Verfahren zur Herstellung von 2-Phenyl-amino-2-imidazolin-Derivaten und von deren Salzen |
| AT330769B (de) * | 1974-04-05 | 1976-07-26 | Chemie Linz Ag | Verfahren zur herstellung von 2-arylamino- 2-imidazolin-derivaten und ihren salzen |
-
1976
- 1976-11-15 DE DE2652004A patent/DE2652004C3/de not_active Expired
-
1977
- 1977-11-03 NL NL7712149A patent/NL7712149A/xx not_active Application Discontinuation
- 1977-11-11 SE SE7712786A patent/SE441923B/sv not_active IP Right Cessation
- 1977-11-14 GB GB47237/77A patent/GB1591879A/en not_active Expired
- 1977-11-14 CH CH1387777A patent/CH633274A5/de not_active IP Right Cessation
- 1977-11-14 CA CA290,841A patent/CA1099274A/en not_active Expired
- 1977-11-14 AT AT0811577A patent/AT362786B/de not_active IP Right Cessation
- 1977-11-15 FR FR7734256A patent/FR2370736A1/fr active Granted
-
1979
- 1979-12-05 US US06/100,655 patent/US4269990A/en not_active Expired - Lifetime
-
1982
- 1982-09-20 SE SE8205383A patent/SE455502B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2652004B2 (de) | 1979-01-18 |
| SE455502B (sv) | 1988-07-18 |
| DE2652004A1 (de) | 1978-05-24 |
| CH633274A5 (de) | 1982-11-30 |
| DE2652004C3 (de) | 1979-09-13 |
| NL7712149A (nl) | 1978-05-17 |
| SE8205383D0 (sv) | 1982-09-20 |
| AT362786B (de) | 1981-06-10 |
| SE441923B (sv) | 1985-11-18 |
| ATA811577A (de) | 1980-11-15 |
| FR2370736A1 (fr) | 1978-06-09 |
| SE8205383L (sv) | 1982-09-20 |
| FR2370736B1 (OSRAM) | 1980-12-19 |
| GB1591879A (en) | 1981-07-01 |
| SE7712786L (sv) | 1978-05-16 |
| US4269990A (en) | 1981-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |