NO783719L - 2-imino-imidazolidin-derivater. - Google Patents
2-imino-imidazolidin-derivater.Info
- Publication number
- NO783719L NO783719L NO783719A NO783719A NO783719L NO 783719 L NO783719 L NO 783719L NO 783719 A NO783719 A NO 783719A NO 783719 A NO783719 A NO 783719A NO 783719 L NO783719 L NO 783719L
- Authority
- NO
- Norway
- Prior art keywords
- imino
- dichlorophenyl
- alkyl
- methyl
- hydrogen
- Prior art date
Links
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 title claims description 7
- -1 alkoxyalkyloxyalkyl Chemical group 0.000 claims description 157
- 150000001875 compounds Chemical class 0.000 claims description 136
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- AGWXBBFKRUVIBC-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound ON1CCNC1=NC1=C(Cl)C=CC=C1Cl AGWXBBFKRUVIBC-UHFFFAOYSA-N 0.000 claims description 62
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 55
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims description 14
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 14
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 13
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 8
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- USTPCDHAGWDHQG-UHFFFAOYSA-N 1-hydroxy-n-(2-iodophenyl)-4,5-dihydroimidazol-2-amine Chemical compound ON1CCNC1=NC1=CC=CC=C1I USTPCDHAGWDHQG-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QJAASZKQJZPVNV-UHFFFAOYSA-N n-(2,6-dibromophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound ON1CCNC1=NC1=C(Br)C=CC=C1Br QJAASZKQJZPVNV-UHFFFAOYSA-N 0.000 claims description 4
- GPHJKVBHAHMBBX-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(furan-2-ylmethoxy)-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC=CC(Cl)=C1N=C1N(OCC=2OC=CC=2)CCN1 GPHJKVBHAHMBBX-UHFFFAOYSA-N 0.000 claims description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- XUPPVNDENVQCHK-UHFFFAOYSA-N 1-but-2-ynoxy-n-(2,6-dichlorophenyl)-4,5-dihydroimidazol-2-amine Chemical compound CC#CCON1CCNC1=NC1=C(Cl)C=CC=C1Cl XUPPVNDENVQCHK-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- NAXYXRKLQHOIPK-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-ethoxy-4,5-dihydroimidazol-2-amine Chemical compound CCON1CCNC1=NC1=C(Cl)C=CC=C1Cl NAXYXRKLQHOIPK-UHFFFAOYSA-N 0.000 claims description 3
- FMGDCVAPRYHZKC-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-prop-2-ynoxy-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC=CC(Cl)=C1N=C1N(OCC#C)CCN1 FMGDCVAPRYHZKC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005586 carbonic acid group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- HRQAHSQCRLABBS-UHFFFAOYSA-N ethyl 4-[[2-(2,6-dichloroanilino)-4,5-dihydroimidazol-1-yl]oxy]butanoate Chemical compound CCOC(=O)CCCON1CCNC1=NC1=C(Cl)C=CC=C1Cl HRQAHSQCRLABBS-UHFFFAOYSA-N 0.000 claims 1
- 235000013312 flour Nutrition 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 279
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 130
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 89
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 78
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- 239000000243 solution Substances 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 27
- 235000011121 sodium hydroxide Nutrition 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 25
- 239000000155 melt Substances 0.000 description 25
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 24
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 24
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
- 239000002244 precipitate Substances 0.000 description 22
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
- 229960000583 acetic acid Drugs 0.000 description 21
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 238000000354 decomposition reaction Methods 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- BMIZFNZTVSHVPN-UHFFFAOYSA-N n'-phenylmethoxyethane-1,2-diamine Chemical compound NCCNOCC1=CC=CC=C1 BMIZFNZTVSHVPN-UHFFFAOYSA-N 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 12
- 238000003776 cleavage reaction Methods 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 230000007017 scission Effects 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- GJTJRMWWLOGXIH-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC=CC(Cl)=C1N=C1N(OCC=2C=CC=CC=2)CCN1 GJTJRMWWLOGXIH-UHFFFAOYSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- GUPLCCFUQTVVBQ-UHFFFAOYSA-N 2,6-dichlorobenzenecarboximidoyl chloride Chemical compound ClC(=N)C1=C(Cl)C=CC=C1Cl GUPLCCFUQTVVBQ-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 239000008120 corn starch Substances 0.000 description 6
- 229940099112 cornstarch Drugs 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- DWDKLIJALQYUIK-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.ON1CCNC1=NC1=C(Cl)C=CC=C1Cl DWDKLIJALQYUIK-UHFFFAOYSA-N 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- HPKBIUNLYQDWDJ-UHFFFAOYSA-N 7a-(bromomethyl)-3ah-isoindole-1,3-dione Chemical compound C1=CC=CC2C(=O)NC(=O)C21CBr HPKBIUNLYQDWDJ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
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- IKSCZINCPQMPFX-UHFFFAOYSA-N n-(2,6-dibromophenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound BrC1=CC=CC(Br)=C1N=C1N(OCC=2C=CC=CC=2)CCN1 IKSCZINCPQMPFX-UHFFFAOYSA-N 0.000 description 1
- VEULXCBDFBQFJD-UHFFFAOYSA-N n-(2,6-dichloro-4-fluorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound ON1CCNC1=NC1=C(Cl)C=C(F)C=C1Cl VEULXCBDFBQFJD-UHFFFAOYSA-N 0.000 description 1
- UTAOLVTXLHAYPR-UHFFFAOYSA-N n-(2,6-dichloro-4-fluorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.ON1CCNC1=NC1=C(Cl)C=C(F)C=C1Cl UTAOLVTXLHAYPR-UHFFFAOYSA-N 0.000 description 1
- HEQNIHWMCKXPGD-UHFFFAOYSA-N n-(2,6-dichloro-4-fluorophenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC(F)=CC(Cl)=C1N=C1N(OCC=2C=CC=CC=2)CCN1 HEQNIHWMCKXPGD-UHFFFAOYSA-N 0.000 description 1
- AFGAAINWRPWTCQ-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(2-phenylethoxy)-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC=CC(Cl)=C1N=C1N(OCCC=2C=CC=CC=2)CCN1 AFGAAINWRPWTCQ-UHFFFAOYSA-N 0.000 description 1
- FSDUGDXRZFUGII-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(3-methoxypropoxy)-4,5-dihydroimidazol-2-amine Chemical compound COCCCON1CCNC1=NC1=C(Cl)C=CC=C1Cl FSDUGDXRZFUGII-UHFFFAOYSA-N 0.000 description 1
- PEKBWKAEIKMHIN-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(3-methylbut-2-enoxy)-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.CC(C)=CCON1CCNC1=NC1=C(Cl)C=CC=C1Cl PEKBWKAEIKMHIN-UHFFFAOYSA-N 0.000 description 1
- PVEDEBBQDGDVTB-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(3-phenylmethoxypropoxy)-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC=CC(Cl)=C1N=C1N(OCCCOCC=2C=CC=CC=2)CCN1 PVEDEBBQDGDVTB-UHFFFAOYSA-N 0.000 description 1
- XJHIIDNRHGBPMW-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(3-phenylprop-2-enoxy)-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1NC1=NCCN1OCC=CC1=CC=CC=C1 XJHIIDNRHGBPMW-UHFFFAOYSA-N 0.000 description 1
- WSXBOBPGZJLPOT-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(furan-2-ylmethoxy)-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1N=C1N(OCC=2OC=CC=2)CCN1 WSXBOBPGZJLPOT-UHFFFAOYSA-N 0.000 description 1
- GKZJZFQXTMRVMV-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(furan-3-ylmethoxy)-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1N=C1N(OCC2=COC=C2)CCN1 GKZJZFQXTMRVMV-UHFFFAOYSA-N 0.000 description 1
- ZYBNMHRUKZDLTL-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(oxolan-2-ylmethoxy)-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1N=C1N(OCC2OCCC2)CCN1 ZYBNMHRUKZDLTL-UHFFFAOYSA-N 0.000 description 1
- JILMGIUGAXOQKQ-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(thiophen-2-ylmethoxy)-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC=CC(Cl)=C1N=C1N(OCC=2SC=CC=2)CCN1 JILMGIUGAXOQKQ-UHFFFAOYSA-N 0.000 description 1
- HECGIDLABKNHCT-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(thiophen-3-ylmethoxy)-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1N=C1N(OCC2=CSC=C2)CCN1 HECGIDLABKNHCT-UHFFFAOYSA-N 0.000 description 1
- WUIJQOVZDPYNHR-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[2-(2-methoxyethoxy)ethoxy]-4,5-dihydroimidazol-2-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.COCCOCCON1CCNC1=NC1=C(Cl)C=CC=C1Cl WUIJQOVZDPYNHR-UHFFFAOYSA-N 0.000 description 1
- ZZPIYVBHXKTUJQ-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[2-(3,4-dimethoxyphenyl)ethoxy]-4,5-dihydroimidazol-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(OC)C(OC)=CC=C1CCON(CCN1)C1=NC1=C(Cl)C=CC=C1Cl ZZPIYVBHXKTUJQ-UHFFFAOYSA-N 0.000 description 1
- UIUKLLAZWLWPSG-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[2-(dimethylamino)ethoxy]-4,5-dihydroimidazol-2-amine Chemical compound CN(C)CCON1CCN=C1NC1=C(Cl)C=CC=C1Cl UIUKLLAZWLWPSG-UHFFFAOYSA-N 0.000 description 1
- UMXIHPDTZJEMEU-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[2-(furan-2-yl)ethoxy]-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC=CC(Cl)=C1N=C1N(OCCC=2OC=CC=2)CCN1 UMXIHPDTZJEMEU-UHFFFAOYSA-N 0.000 description 1
- MLCAVUZBORLGBJ-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-methoxy-4,5-dihydroimidazol-2-amine Chemical compound CON1CCNC1=NC1=C(Cl)C=CC=C1Cl MLCAVUZBORLGBJ-UHFFFAOYSA-N 0.000 description 1
- IBPLJCMQWCZHHK-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-methoxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.CON1CCNC1=NC1=C(Cl)C=CC=C1Cl IBPLJCMQWCZHHK-UHFFFAOYSA-N 0.000 description 1
- LRLVEQHIKRNXDU-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-pent-3-ynoxy-4,5-dihydroimidazol-2-amine Chemical compound CC#CCCON1CCNC1=NC1=C(Cl)C=CC=C1Cl LRLVEQHIKRNXDU-UHFFFAOYSA-N 0.000 description 1
- KWQTUKLWUDHJJJ-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-pent-4-enyl-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1N=C1N(CCCC=C)CCN1 KWQTUKLWUDHJJJ-UHFFFAOYSA-N 0.000 description 1
- JLOTUYHYUVYXHP-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-propan-2-yloxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.CC(C)ON1CCNC1=NC1=C(Cl)C=CC=C1Cl JLOTUYHYUVYXHP-UHFFFAOYSA-N 0.000 description 1
- UBLYPCKVEGDELD-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-propoxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.CCCON1CCNC1=NC1=C(Cl)C=CC=C1Cl UBLYPCKVEGDELD-UHFFFAOYSA-N 0.000 description 1
- CMRLEIHOFQKMCW-UHFFFAOYSA-N n-(2,6-dichlorophenyl)formamide Chemical compound ClC1=CC=CC(Cl)=C1NC=O CMRLEIHOFQKMCW-UHFFFAOYSA-N 0.000 description 1
- MDODWRKVDNXIIC-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.CC1=CC=CC(C)=C1N=C1N(OCC=2C=CC=CC=2)CCN1 MDODWRKVDNXIIC-UHFFFAOYSA-N 0.000 description 1
- CEDADIWWFVHSBA-UHFFFAOYSA-N n-(2-bromophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.ON1CCNC1=NC1=CC=CC=C1Br CEDADIWWFVHSBA-UHFFFAOYSA-N 0.000 description 1
- UYTLOSLEDGWTEZ-UHFFFAOYSA-N n-(2-bromophenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound BrC1=CC=CC=C1N=C1N(OCC=2C=CC=CC=2)CCN1 UYTLOSLEDGWTEZ-UHFFFAOYSA-N 0.000 description 1
- MSGBWBOQYFTIML-UHFFFAOYSA-N n-(2-bromophenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.BrC1=CC=CC=C1N=C1N(OCC=2C=CC=CC=2)CCN1 MSGBWBOQYFTIML-UHFFFAOYSA-N 0.000 description 1
- IIEDWLXTBSHBFY-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.CC1=CC=CC(Cl)=C1N=C1N(O)CCN1 IIEDWLXTBSHBFY-UHFFFAOYSA-N 0.000 description 1
- QKLWMHXMMCWURO-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound CC1=CC=CC(Cl)=C1N=C1N(OCC=2C=CC=CC=2)CCN1 QKLWMHXMMCWURO-UHFFFAOYSA-N 0.000 description 1
- CWBMBOIYDYHLGR-UHFFFAOYSA-N n-(2-chlorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.ON1CCNC1=NC1=CC=CC=C1Cl CWBMBOIYDYHLGR-UHFFFAOYSA-N 0.000 description 1
- ZQGIUNRMUNUWTD-UHFFFAOYSA-N n-(2-chlorophenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC=CC=C1N=C1N(OCC=2C=CC=CC=2)CCN1 ZQGIUNRMUNUWTD-UHFFFAOYSA-N 0.000 description 1
- UQKYCHRDZYIACM-UHFFFAOYSA-N n-(2-chlorophenyl)-1-prop-2-ynoxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC=C1N=C1N(OCC#C)CCN1 UQKYCHRDZYIACM-UHFFFAOYSA-N 0.000 description 1
- XBJKGJWUEUFHGL-UHFFFAOYSA-N n-(2-iodophenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound IC1=CC=CC=C1N=C1N(OCC=2C=CC=CC=2)CCN1 XBJKGJWUEUFHGL-UHFFFAOYSA-N 0.000 description 1
- PSFSHFBGJJQZGT-UHFFFAOYSA-N n-(2-iodophenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.IC1=CC=CC=C1N=C1N(OCC=2C=CC=CC=2)CCN1 PSFSHFBGJJQZGT-UHFFFAOYSA-N 0.000 description 1
- WSIAHOFXNLOKLW-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.ON1CCNC1=NC1=CC=C(Cl)C(Cl)=C1 WSIAHOFXNLOKLW-UHFFFAOYSA-N 0.000 description 1
- QRNIKHHRTQSIDY-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.C1=C(C)C(C)=CC=C1N=C1N(O)CCN1 QRNIKHHRTQSIDY-UHFFFAOYSA-N 0.000 description 1
- FDLRNORXWZBGQK-UHFFFAOYSA-N n-(4-chloro-2,6-diethylphenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound CCC1=CC(Cl)=CC(CC)=C1N=C1N(O)CCN1 FDLRNORXWZBGQK-UHFFFAOYSA-N 0.000 description 1
- MXKVXZVIRDCINO-UHFFFAOYSA-N n-(4-chloro-2,6-diethylphenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound CCC1=CC(Cl)=CC(CC)=C1N=C1N(OCC=2C=CC=CC=2)CCN1 MXKVXZVIRDCINO-UHFFFAOYSA-N 0.000 description 1
- LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VTMPVNWDRKCAMC-UHFFFAOYSA-N n-phenyl-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound C=1C=CC=CC=1CON1CCNC1=NC1=CC=CC=C1 VTMPVNWDRKCAMC-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- DNTZVTNYNDECPB-UHFFFAOYSA-N pent-1-yn-3-yl 4-methylbenzenesulfonate Chemical compound CCC(C#C)OS(=O)(=O)C1=CC=C(C)C=C1 DNTZVTNYNDECPB-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Chemical group 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/40—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of thiourea or isothiourea groups further bound to other hetero atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (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)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU78467 | 1977-11-07 | ||
| CH966878 | 1978-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO783719L true NO783719L (no) | 1979-05-08 |
Family
ID=25705131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO783719A NO783719L (no) | 1977-11-07 | 1978-11-06 | 2-imino-imidazolidin-derivater. |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US4244957A (xx) |
| EP (1) | EP0002010B1 (xx) |
| JP (1) | JPS5473779A (xx) |
| AR (1) | AR223656A1 (xx) |
| AT (1) | AT371112B (xx) |
| AU (1) | AU4132478A (xx) |
| BR (1) | BR7807317A (xx) |
| CA (1) | CA1106847A (xx) |
| CS (1) | CS212309B2 (xx) |
| DD (1) | DD139847A5 (xx) |
| DE (2) | DE2861952D1 (xx) |
| DK (1) | DK494978A (xx) |
| EG (1) | EG13665A (xx) |
| ES (3) | ES480113A1 (xx) |
| FI (1) | FI783393A (xx) |
| FR (1) | FR2407919A1 (xx) |
| GB (2) | GB2086379B (xx) |
| IL (1) | IL55832A0 (xx) |
| IT (1) | IT1160046B (xx) |
| MC (1) | MC1223A1 (xx) |
| MT (1) | MTP837B (xx) |
| NL (1) | NL7811070A (xx) |
| NO (1) | NO783719L (xx) |
| NZ (1) | NZ188798A (xx) |
| OA (1) | OA06084A (xx) |
| PL (1) | PL210759A1 (xx) |
| PT (1) | PT68752A (xx) |
| RO (1) | RO76151A (xx) |
| SE (1) | SE7811455L (xx) |
| SU (2) | SU831073A3 (xx) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4287201A (en) * | 1980-03-03 | 1981-09-01 | Merck & Co., Inc. | Anovulatory method and chicken feed compositions |
| CA1175434A (en) * | 1980-09-10 | 1984-10-02 | Hoffmann-La Roche Limited | ¬(2-phenylamino-1-imidazolidinyloxy)methyl| pyridine 1-oxide derivatives |
| DE3642453A1 (de) * | 1986-12-12 | 1988-06-23 | Bayer Ag | Neue, fluor enthaltende 5-trihalogenmethyl-isoxazole und ein verfahren zu deren herstellung |
| DE19514579A1 (de) * | 1995-04-20 | 1996-10-24 | Boehringer Ingelheim Kg | Verwendung von alpha¶1¶¶L¶-Agonisten zur Behandlung der Harninkontinenz |
| ATE364595T1 (de) * | 2000-07-07 | 2007-07-15 | Medicure Int Inc | Pyridoxin- und pyridoxalanaloga als cardiovasculäre therapeutika |
| GB2374251A (en) * | 2001-04-04 | 2002-10-09 | Secr Defence | Base station transmitter |
| US20030139606A1 (en) * | 2001-11-09 | 2003-07-24 | Ray Anup Kumar | Process for preparing 5-methylisoxazole-4-carboxylic- (4'-trifluoromethyl)-anilide |
| US6703409B2 (en) | 2002-01-31 | 2004-03-09 | Boehringer Ingelheim Pharma Gmbh & Co Kg | 2′-Halo-3′,5′-dialkoxyphen-1′-yl-imino-2-imidazolidine and the use thereof as a drug |
| EP1333028A1 (en) * | 2002-01-31 | 2003-08-06 | Boehringer Ingelheim Pharma GmbH & Co.KG | 2'-Halo-3',5'-dialkoxyphen-1'-yl-imino-2-imidazolidine derivatives and the use thereof for the treatment of urinary incontinence |
| DK2328619T3 (en) * | 2008-08-22 | 2017-03-13 | Baxalta GmbH | POLYMER BENZYL CARBONATE DERIVATES |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670274U (de) | 1953-07-30 | 1954-01-14 | Leo Schirk | Stahlblechschalttafel. |
| DE1815788U (de) | 1959-12-12 | 1960-07-28 | Walther Loeffler | Ventil fuer spuelbecken, waschbecken, bidets, wannen. |
| US3236857A (en) * | 1961-10-09 | 1966-02-22 | Boehringer Sohn Ingelheim | 2-(phenyl-amino)-1, 3-diazacyclopentene-(2) substitution products |
| NL123037C (xx) | 1963-10-04 | |||
| DE1545628A1 (de) * | 1965-10-01 | 1970-06-25 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von blutdrucksenkend und sedativ wirksamen Derivaten des 2-(2-Halogenanilino)-1,3-diazacyclopentens-(2) |
| DE1670274A1 (de) * | 1966-10-31 | 1970-07-16 | Boehringer Sohn Ingelheim | Neues Verfahren zur Herstellung von 2-Arylamino-1,3-diazacycloalkenen-(2) |
| ES352379A1 (es) | 1967-05-26 | 1969-08-01 | Boehringer Sohn Ingelheim | Procedimiento para la preparacion de 1,3-diazaciclopenteno-(2) sustituido en posicion 2. |
| DE1670230A1 (de) | 1967-05-26 | 1971-01-21 | Boehringer Sohn Ingelheim | Neues Verfahren zur Herstellung von in 2-Stellung substituierten 1,3-Diazacycloalkenen(2) |
| US3454301A (en) * | 1967-09-29 | 1969-07-08 | John W Lehmann | Glare-inhibiting device |
| GB1246312A (en) * | 1968-01-10 | 1971-09-15 | Syntex Energy Res Inc | 4,5-substituted n-oxy and hydroxy hydroimidazoles |
| DE1770872A1 (de) | 1968-08-26 | 1972-01-13 | Dresden Arzneimittel | Verfahren zur Herstellung von Imidazolin-2-Derivaten |
| BE721781A (xx) | 1968-10-03 | 1969-04-03 | ||
| BE759048A (fr) * | 1969-11-17 | 1971-05-17 | Boehringer Sohn Ingelheim | Nouvelles n-aminoalcoyl-arylamino-imidazolines-(2) substituees et procedes pour les fabriquer |
| DE2016290A1 (de) * | 1970-04-06 | 1971-11-04 | C H Boehrmger Sohn, 6507 Ingel heim | Substituierte N Hydroxylakyl 2 arylamine) imidazoline (2) und Verfahren zu deren Herstellung |
| US3740412A (en) * | 1970-04-08 | 1973-06-19 | Synvar Ass | Imidazoline-3-oxide-1-oxyl derivatives |
| DE2038107A1 (de) * | 1970-07-31 | 1972-02-10 | Henkel & Cie Gmbh | Fluessige,gegebenenfalls als Wasch- oder Reinigungsmittel brauchbare stabilisierte Enzympraeparate |
| US3799942A (en) * | 1971-04-12 | 1974-03-26 | Syva Corp | 4,5-substituted n-oxy and hydroxy hydroimidazoles |
| BE787477A (fr) * | 1971-08-12 | 1973-02-12 | Bayer Ag | 1-phenyl-2-imino-imidazolidines, leur procede de preparation etleur application comme repulsifs a l'egard des oiseaux |
| DE2457979A1 (de) | 1974-12-07 | 1976-06-16 | Beiersdorf Ag | 2-n-aryl-hydroxyamino-imidazoline-(2) und verfahren zu deren herstellung |
| DE2523103C3 (de) * | 1975-05-24 | 1979-11-29 | C.H. Boehringer Sohn, 6507 Ingelheim | Substituierte 2-[N-Progargyl-N-(2-chlorphenyl)amino] -imidazoline-^), deren Säureadditionssalze, Verfahren zu ihrer Herstellung und deren Verwendung |
| AT339897B (de) * | 1975-09-25 | 1977-11-10 | Chemie Linz Ag | Verfahren zur herstellung des neuen 1-benzoyl-2- (2',6'-dichlorphenylamino) -2-imidazolins und von dessen salzen |
| DE2626128A1 (de) * | 1976-06-11 | 1977-12-22 | Beiersdorf Ag | N-substituierte benzimidazolin-2-one und verfahren zu deren herstellung |
| DE2709720A1 (de) * | 1977-03-05 | 1978-09-07 | Beiersdorf Ag | N-substituierte 2-arylamino-imidazoline-(2), verfahren zu deren herstellung und neue hydroxylamine als zwischenprodukte |
| US4131679A (en) * | 1977-07-26 | 1978-12-26 | Sandoz, Inc. | Substituted 4-hydroxy pyridones |
| DE2811847A1 (de) * | 1978-03-17 | 1979-09-20 | Lentia Gmbh | Neue arylaminoimidazolinderivate, deren herstellung und verwendung als arzneimittel |
-
1978
- 1978-10-26 MT MT837A patent/MTP837B/xx unknown
- 1978-10-31 IL IL7855832A patent/IL55832A0/xx unknown
- 1978-11-01 NZ NZ188798A patent/NZ188798A/xx unknown
- 1978-11-02 FR FR7831026A patent/FR2407919A1/fr not_active Withdrawn
- 1978-11-02 OA OA56651A patent/OA06084A/xx unknown
- 1978-11-03 CS CS787188A patent/CS212309B2/cs unknown
- 1978-11-03 DE DE7878101299T patent/DE2861952D1/de not_active Expired
- 1978-11-03 EP EP78101299A patent/EP0002010B1/de not_active Expired
- 1978-11-03 RO RO7895588A patent/RO76151A/ro unknown
- 1978-11-03 DD DD78208873A patent/DD139847A5/de unknown
- 1978-11-03 DE DE19782847766 patent/DE2847766A1/de not_active Withdrawn
- 1978-11-03 MC MC781338A patent/MC1223A1/xx unknown
- 1978-11-03 AU AU41324/78A patent/AU4132478A/en active Pending
- 1978-11-04 SU SU782680652A patent/SU831073A3/ru active
- 1978-11-05 EG EG646/78A patent/EG13665A/xx active
- 1978-11-06 GB GB8125779A patent/GB2086379B/en not_active Expired
- 1978-11-06 DK DK494978A patent/DK494978A/da not_active Application Discontinuation
- 1978-11-06 JP JP13593678A patent/JPS5473779A/ja active Pending
- 1978-11-06 SE SE7811455A patent/SE7811455L/xx not_active Application Discontinuation
- 1978-11-06 NO NO783719A patent/NO783719L/no unknown
- 1978-11-06 CA CA315,866A patent/CA1106847A/en not_active Expired
- 1978-11-06 IT IT29486/78A patent/IT1160046B/it active
- 1978-11-06 US US05/958,300 patent/US4244957A/en not_active Expired - Lifetime
- 1978-11-06 PT PT68752A patent/PT68752A/pt unknown
- 1978-11-06 AT AT0791378A patent/AT371112B/de not_active IP Right Cessation
- 1978-11-06 GB GB7843271A patent/GB2008579B/en not_active Expired
- 1978-11-07 AR AR274367A patent/AR223656A1/es active
- 1978-11-07 FI FI783393A patent/FI783393A/fi unknown
- 1978-11-07 NL NL7811070A patent/NL7811070A/xx not_active Application Discontinuation
- 1978-11-07 PL PL21075978A patent/PL210759A1/xx unknown
- 1978-11-07 BR BR7807317A patent/BR7807317A/pt unknown
-
1979
- 1979-04-30 ES ES480113A patent/ES480113A1/es not_active Expired
- 1979-04-30 ES ES480112A patent/ES480112A1/es not_active Expired
- 1979-04-30 ES ES480111A patent/ES480111A1/es not_active Expired
- 1979-08-31 SU SU792806102A patent/SU910119A3/ru active
-
1980
- 1980-08-14 US US06/178,223 patent/US4355033A/en not_active Expired - Lifetime
-
1982
- 1982-08-05 US US06/405,476 patent/US4511720A/en not_active Expired - Fee Related
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