CS212309B2 - Method of making the new 2-iminoimidazolidine derivatives - Google Patents
Method of making the new 2-iminoimidazolidine derivatives Download PDFInfo
- Publication number
- CS212309B2 CS212309B2 CS787188A CS718878A CS212309B2 CS 212309 B2 CS212309 B2 CS 212309B2 CS 787188 A CS787188 A CS 787188A CS 718878 A CS718878 A CS 718878A CS 212309 B2 CS212309 B2 CS 212309B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- compound
- group
- formula
- alkyl
- acid addition
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 5
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 112
- -1 hydroxy hydroxy Chemical group 0.000 claims description 85
- 239000002253 acid Substances 0.000 claims description 49
- 238000002360 preparation method Methods 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 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 description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 101100022176 Mus musculus Gstz1 gene Proteins 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 105
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 71
- 239000000203 mixture Substances 0.000 description 70
- 239000000243 solution Substances 0.000 description 63
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 125000001841 imino group Chemical group [H]N=* 0.000 description 29
- 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 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000000155 melt Substances 0.000 description 21
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 20
- 238000000354 decomposition reaction Methods 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 229920002261 Corn starch Polymers 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 5
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- BMIZFNZTVSHVPN-UHFFFAOYSA-N n'-phenylmethoxyethane-1,2-diamine Chemical compound NCCNOCC1=CC=CC=C1 BMIZFNZTVSHVPN-UHFFFAOYSA-N 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 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 4
- 235000019759 Maize starch Nutrition 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000008120 corn starch 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
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
- LLSXLHOEFSZLRY-UHFFFAOYSA-N 2-[2-(phenylmethoxyamino)ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCNOCC1=CC=CC=C1 LLSXLHOEFSZLRY-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 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 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 230000002889 sympathetic effect Effects 0.000 description 3
- 230000035488 systolic blood pressure Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 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 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 2
- FVPGJXXACUQQGV-UHFFFAOYSA-N 2-(2-chloroethyl)pyridine Chemical compound ClCCC1=CC=CC=N1 FVPGJXXACUQQGV-UHFFFAOYSA-N 0.000 description 2
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- HOCPDSKONPQIQM-UHFFFAOYSA-N 4-(2-bromoethyl)isoindole-1,3-dione Chemical compound BrCCC1=CC=CC2=C1C(=O)NC2=O HOCPDSKONPQIQM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 101150046432 Tril gene Proteins 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000004531 blood pressure lowering effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
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- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PFRDRCIPKPEULG-UHFFFAOYSA-N imidazol-2-imine Chemical class N=C1N=CC=N1 PFRDRCIPKPEULG-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- RPUSEAZAXATRHG-UHFFFAOYSA-N n'-phenylmethoxyethane-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.NCCNOCC1=CC=CC=C1 RPUSEAZAXATRHG-UHFFFAOYSA-N 0.000 description 1
- YVROMXQNKFEXQU-UHFFFAOYSA-N n-(2,6-dibromophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.ON1CCNC1=NC1=C(Br)C=CC=C1Br YVROMXQNKFEXQU-UHFFFAOYSA-N 0.000 description 1
- 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
- APLHVRWIHDYRPN-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(2-methylsulfanylethoxy)-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.CSCCON1CCNC1=NC1=C(Cl)C=CC=C1Cl APLHVRWIHDYRPN-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
- 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
- SIMIUJZYFKJBAM-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-ethoxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.CCON1CCNC1=NC1=C(Cl)C=CC=C1Cl SIMIUJZYFKJBAM-UHFFFAOYSA-N 0.000 description 1
- 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 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
- YNZSEIBTUURYIO-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-prop-2-ynoxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1N=C1N(OCC#C)CCN1 YNZSEIBTUURYIO-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
- CMRLEIHOFQKMCW-UHFFFAOYSA-N n-(2,6-dichlorophenyl)formamide Chemical compound ClC1=CC=CC(Cl)=C1NC=O CMRLEIHOFQKMCW-UHFFFAOYSA-N 0.000 description 1
- OOXGLGYFZQLBPY-UHFFFAOYSA-N n-(2-aminoethyl)hydroxylamine;dihydrobromide Chemical compound Br.Br.NCCNO OOXGLGYFZQLBPY-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
- GVFDTUYDPJEFJT-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound CC1=CC=CC(Cl)=C1N=C1N(O)CCN1 GVFDTUYDPJEFJT-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
- YSDIAVWNYCLIPC-UHFFFAOYSA-N n-(2-chlorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound ON1CCNC1=NC1=CC=CC=C1Cl YSDIAVWNYCLIPC-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
- 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- SLMCDJBSBDYBAX-UHFFFAOYSA-N pentan-3-yl 4-methylbenzenesulfonate Chemical compound CCC(CC)OS(=O)(=O)C1=CC=C(C)C=C1 SLMCDJBSBDYBAX-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 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
- ZRHANBBTXQZFSP-UHFFFAOYSA-M potassium;4-amino-3,5,6-trichloropyridine-2-carboxylate Chemical compound [K+].NC1=C(Cl)C(Cl)=NC(C([O-])=O)=C1Cl ZRHANBBTXQZFSP-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005303 weighing Methods 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)
- Medicinal Preparation (AREA)
- Indole Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS802609A CS212310B2 (cs) | 1977-11-07 | 1980-04-15 | Způsob výroby nových 2-iminoimidazolidinových derivátů |
| CS802610A CS212311B2 (cs) | 1977-11-07 | 1980-04-15 | Způsob výroby nových 2-iminoimidazolidinových derivátů |
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 |
|---|---|
| CS212309B2 true CS212309B2 (en) | 1982-03-26 |
Family
ID=25705131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS787188A CS212309B2 (en) | 1977-11-07 | 1978-11-03 | Method of making the new 2-iminoimidazolidine derivatives |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US4244957A (es) |
| EP (1) | EP0002010B1 (es) |
| JP (1) | JPS5473779A (es) |
| AR (1) | AR223656A1 (es) |
| AT (1) | AT371112B (es) |
| AU (1) | AU4132478A (es) |
| BR (1) | BR7807317A (es) |
| CA (1) | CA1106847A (es) |
| CS (1) | CS212309B2 (es) |
| DD (1) | DD139847A5 (es) |
| DE (2) | DE2861952D1 (es) |
| DK (1) | DK494978A (es) |
| EG (1) | EG13665A (es) |
| ES (3) | ES480113A1 (es) |
| FI (1) | FI783393A7 (es) |
| FR (1) | FR2407919A1 (es) |
| GB (2) | GB2086379B (es) |
| IL (1) | IL55832A0 (es) |
| IT (1) | IT1160046B (es) |
| MC (1) | MC1223A1 (es) |
| MT (1) | MTP837B (es) |
| NL (1) | NL7811070A (es) |
| NO (1) | NO783719L (es) |
| NZ (1) | NZ188798A (es) |
| OA (1) | OA06084A (es) |
| PL (1) | PL210759A1 (es) |
| PT (1) | PT68752A (es) |
| RO (1) | RO76151A (es) |
| SE (1) | SE7811455L (es) |
| SU (2) | SU831073A3 (es) |
Families Citing this family (11)
| 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 |
| EP0757677B1 (en) * | 1994-04-26 | 2003-06-18 | Syntex (U.S.A.) LLC | Benzocyclohexylimidazolethione derivatives |
| 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 |
| WO2003042193A1 (en) * | 2001-11-09 | 2003-05-22 | Geneva Pharmaceuticals, Inc. | Process for preparing 5-methylisoxazole-4-carboxylic-(4'-trifluoromethyl)-anilide |
| 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 |
| 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 |
| BRPI0917819B8 (pt) * | 2008-08-22 | 2021-05-25 | Baxalta GmbH | compostos derivados poliméricos de benzil carbonato, conjugado de droga, formulação farmacêutica, e, uso de um conjugado |
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 (es) | 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) |
| DE1670230A1 (de) | 1967-05-26 | 1971-01-21 | Boehringer Sohn Ingelheim | Neues Verfahren zur Herstellung von in 2-Stellung substituierten 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. |
| 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 (es) | 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 EP EP78101299A patent/EP0002010B1/de not_active Expired
- 1978-11-03 AU AU41324/78A patent/AU4132478A/en active Pending
- 1978-11-03 DE DE7878101299T patent/DE2861952D1/de not_active Expired
- 1978-11-03 RO RO7895588A patent/RO76151A/ro unknown
- 1978-11-03 MC MC781338A patent/MC1223A1/fr unknown
- 1978-11-03 DD DD78208873A patent/DD139847A5/de unknown
- 1978-11-03 DE DE19782847766 patent/DE2847766A1/de not_active Withdrawn
- 1978-11-03 CS CS787188A patent/CS212309B2/cs unknown
- 1978-11-04 SU SU782680652A patent/SU831073A3/ru active
- 1978-11-05 EG EG646/78A patent/EG13665A/xx active
- 1978-11-06 PT PT68752A patent/PT68752A/pt unknown
- 1978-11-06 IT IT29486/78A patent/IT1160046B/it active
- 1978-11-06 NO NO783719A patent/NO783719L/no unknown
- 1978-11-06 JP JP13593678A patent/JPS5473779A/ja active Pending
- 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 US US05/958,300 patent/US4244957A/en not_active Expired - Lifetime
- 1978-11-06 AT AT0791378A patent/AT371112B/de not_active IP Right Cessation
- 1978-11-06 SE SE7811455A patent/SE7811455L/xx not_active Application Discontinuation
- 1978-11-06 CA CA315,866A patent/CA1106847A/en not_active Expired
- 1978-11-06 GB GB7843271A patent/GB2008579B/en not_active Expired
- 1978-11-07 NL NL7811070A patent/NL7811070A/xx not_active Application Discontinuation
- 1978-11-07 AR AR274367A patent/AR223656A1/es active
- 1978-11-07 FI FI783393A patent/FI783393A7/fi unknown
- 1978-11-07 BR BR7807317A patent/BR7807317A/pt unknown
- 1978-11-07 PL PL21075978A patent/PL210759A1/xx unknown
-
1979
- 1979-04-30 ES ES480113A patent/ES480113A1/es not_active Expired
- 1979-04-30 ES ES480111A patent/ES480111A1/es not_active Expired
- 1979-04-30 ES ES480112A patent/ES480112A1/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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