CS200165B2 - Method of preparing novel cyclic derivatives of urea - Google Patents
Method of preparing novel cyclic derivatives of urea Download PDFInfo
- Publication number
- CS200165B2 CS200165B2 CS726803A CS680372A CS200165B2 CS 200165 B2 CS200165 B2 CS 200165B2 CS 726803 A CS726803 A CS 726803A CS 680372 A CS680372 A CS 680372A CS 200165 B2 CS200165 B2 CS 200165B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- mol
- diethylcarbamoyl
- compounds
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 125000004122 cyclic group Chemical group 0.000 title abstract 2
- 239000004202 carbamide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- -1 cyclic ureas Chemical class 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical class OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000003254 radicals Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- 239000002904 solvent Substances 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- IWJSZNIFIDAYDY-UHFFFAOYSA-N n,n-diethylpiperazine-1-carboxamide Chemical compound CCN(CC)C(=O)N1CCNCC1 IWJSZNIFIDAYDY-UHFFFAOYSA-N 0.000 abstract description 11
- 239000000543 intermediate Substances 0.000 abstract description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 5
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 abstract description 5
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 abstract description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 4
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract 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 abstract description 2
- HTSQWLLKIZBMEO-UHFFFAOYSA-N 1,5-diazocane Chemical compound C1CNCCCNC1 HTSQWLLKIZBMEO-UHFFFAOYSA-N 0.000 abstract description 2
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 abstract description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract description 2
- 230000001857 anti-mycotic effect Effects 0.000 abstract description 2
- 230000000840 anti-viral effect Effects 0.000 abstract description 2
- 239000002543 antimycotic Substances 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 abstract 1
- CXPUAWQOXQINEX-UHFFFAOYSA-N 1,4-diazocane Chemical compound C1CCNCCNC1 CXPUAWQOXQINEX-UHFFFAOYSA-N 0.000 abstract 1
- 101100188555 Arabidopsis thaliana OCT6 gene Proteins 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 abstract 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- 239000002585 base Substances 0.000 description 55
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 14
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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 12
- 239000000706 filtrate Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 6
- 241000700605 Viruses Species 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 229940008309 acetone / ethanol Drugs 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 229910052783 alkali metal Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- ISXCTRKWHFWFAF-UHFFFAOYSA-N 1-(2-piperazin-1-ylethyl)-3-tetradecylimidazolidin-2-one Chemical compound N1(CCNCC1)CCN1C(N(CC1)CCCCCCCCCCCCCC)=O ISXCTRKWHFWFAF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000700647 Variola virus Species 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000007821 culture assay Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- OQXWEZVLEIJVSI-UHFFFAOYSA-N n,n-diethyl-4-[2-(2-oxo-3-tetradecylimidazolidin-1-yl)ethyl]piperazine-1-carboxamide Chemical compound O=C1N(CCCCCCCCCCCCCC)CCN1CCN1CCN(C(=O)N(CC)CC)CC1 OQXWEZVLEIJVSI-UHFFFAOYSA-N 0.000 description 2
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 150000003459 sulfonic acid esters Chemical group 0.000 description 2
- 241000712461 unidentified influenza virus Species 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- JWQMKMSVOYQICF-UHFFFAOYSA-N 1,3-dibromoprop-1-ene Chemical compound BrCC=CBr JWQMKMSVOYQICF-UHFFFAOYSA-N 0.000 description 1
- YGSFFDHIYYOVHV-UHFFFAOYSA-N 1-(2-chloroethyl)imidazolidin-2-one Chemical compound ClCCN1CCNC1=O YGSFFDHIYYOVHV-UHFFFAOYSA-N 0.000 description 1
- LBYUNVNJLBXOPQ-UHFFFAOYSA-N 1-(2-hydrazinylethyl)-3-methylimidazolidin-2-one Chemical compound N(N)CCN1C(N(CC1)C)=O LBYUNVNJLBXOPQ-UHFFFAOYSA-N 0.000 description 1
- UNMQXZLBHSJNMJ-UHFFFAOYSA-N C(C)N(C(=O)N1C(CN(C(C1)C)CCN1C(N(CC1)C)=O)C)CC Chemical compound C(C)N(C(=O)N1C(CN(C(C1)C)CCN1C(N(CC1)C)=O)C)CC UNMQXZLBHSJNMJ-UHFFFAOYSA-N 0.000 description 1
- 101100042788 Caenorhabditis elegans him-1 gene Proteins 0.000 description 1
- 101100126625 Caenorhabditis elegans itr-1 gene Proteins 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FKCBWUMLYSJYEH-UHFFFAOYSA-N Cl.C(C)(C)N(C(=O)N1CCN(CC1)CCN1C(N(CC1)CCCCCCCCCCCCCC)=O)C(C)C Chemical compound Cl.C(C)(C)N(C(=O)N1CCN(CC1)CCN1C(N(CC1)CCCCCCCCCCCCCC)=O)C(C)C FKCBWUMLYSJYEH-UHFFFAOYSA-N 0.000 description 1
- SNCOKGGGIATVDJ-UHFFFAOYSA-N Cl.C(C)N(C(=O)N1CCN(CC1)CCCN1C(N(CC1)CCCCCCCCCCCCCC)=O)CC Chemical compound Cl.C(C)N(C(=O)N1CCN(CC1)CCCN1C(N(CC1)CCCCCCCCCCCCCC)=O)CC SNCOKGGGIATVDJ-UHFFFAOYSA-N 0.000 description 1
- APRJFNLVTJWEPP-UHFFFAOYSA-N Diethylcarbamic acid Chemical compound CCN(CC)C(O)=O APRJFNLVTJWEPP-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- LRULVYSBRWUVGR-FCHUYYIVSA-N GSK2879552 Chemical compound C1=CC(C(=O)O)=CC=C1CN1CCC(CN[C@H]2[C@@H](C2)C=2C=CC=CC=2)CC1 LRULVYSBRWUVGR-FCHUYYIVSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
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- 241000699670 Mus sp. Species 0.000 description 1
- GYMMRYFVRXNIRB-UHFFFAOYSA-N N,N-dibutyl-4-[2-(3-methyl-2-oxoimidazolidin-1-yl)ethyl]piperazine-1-carboxamide Chemical compound C(CCC)N(C(=O)N1CCN(CC1)CCN1C(N(CC1)C)=O)CCCC GYMMRYFVRXNIRB-UHFFFAOYSA-N 0.000 description 1
- YKSINNGJLQQQSV-UHFFFAOYSA-N N,N-diethyl-4-[3-(3-methyl-2-oxo-1,3-diazinan-1-yl)propyl]piperazine-1-carboxamide Chemical compound C(C)N(C(=O)N1CCN(CC1)CCCN1C(N(CCC1)C)=O)CC YKSINNGJLQQQSV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- UQONAEXHTGDOIH-AWEZNQCLSA-N O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 Chemical compound O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 UQONAEXHTGDOIH-AWEZNQCLSA-N 0.000 description 1
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000700618 Vaccinia virus Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000002832 anti-viral assay Methods 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JUXPKLBIQOHCHE-UHFFFAOYSA-N azepan-1-yl(piperazin-1-yl)methanone Chemical compound C1CCCCCN1C(=O)N1CCNCC1 JUXPKLBIQOHCHE-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 230000003328 fibroblastic effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- AWXBWWHTLMCPSD-UHFFFAOYSA-N n,n-diethyl-2,5-dimethylpiperazine-1-carboxamide Chemical compound CCN(CC)C(=O)N1CC(C)NCC1C AWXBWWHTLMCPSD-UHFFFAOYSA-N 0.000 description 1
- XMFYMWXCIWIHAC-UHFFFAOYSA-N n,n-dimethylpiperazine-1-carboxamide Chemical compound CN(C)C(=O)N1CCNCC1 XMFYMWXCIWIHAC-UHFFFAOYSA-N 0.000 description 1
- VVJLNGRNIVBGRD-UHFFFAOYSA-N n,n-dipropylpiperazine-1-carboxamide Chemical compound CCCN(CCC)C(=O)N1CCNCC1 VVJLNGRNIVBGRD-UHFFFAOYSA-N 0.000 description 1
- GRRYSIXDUIAUGY-UHFFFAOYSA-N n-methylcarbamoyl chloride Chemical compound CNC(Cl)=O GRRYSIXDUIAUGY-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- RASPWLYDBYZRCR-UHFFFAOYSA-N pyrrolidin-1-ium-2-one;chloride Chemical compound Cl.O=C1CCCN1 RASPWLYDBYZRCR-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 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 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000012090 tissue culture technique Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine 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 directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2150438A DE2150438C3 (de) | 1971-10-09 | 1971-10-09 | Cyclische Harnstoffderivate und ihre Salze mit pharmakologisch unbedenklichen Säuren, Verfahren zu ihrer Herstellung und diese enthaltend pharmazeutische Präparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200165B2 true CS200165B2 (en) | 1980-08-29 |
Family
ID=5821924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS726803A CS200165B2 (en) | 1971-10-09 | 1972-10-09 | Method of preparing novel cyclic derivatives of urea |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US3919233A (en, 2012) |
| JP (1) | JPS5728702B2 (en, 2012) |
| KR (1) | KR780000046B1 (en, 2012) |
| AR (1) | AR204390A1 (en, 2012) |
| AT (1) | AT315834B (en, 2012) |
| AU (1) | AU467578B2 (en, 2012) |
| BE (1) | BE789830A (en, 2012) |
| CA (1) | CA980774A (en, 2012) |
| CH (1) | CH586220A5 (en, 2012) |
| CS (1) | CS200165B2 (en, 2012) |
| CU (1) | CU33794A (en, 2012) |
| DD (1) | DD101159A5 (en, 2012) |
| DE (1) | DE2150438C3 (en, 2012) |
| EG (1) | EG11262A (en, 2012) |
| ES (1) | ES407203A1 (en, 2012) |
| FI (1) | FI57588C (en, 2012) |
| FR (1) | FR2157839B1 (en, 2012) |
| GB (1) | GB1359265A (en, 2012) |
| HK (1) | HK51777A (en, 2012) |
| HU (1) | HU165870B (en, 2012) |
| IE (1) | IE36716B1 (en, 2012) |
| IL (1) | IL40411A (en, 2012) |
| LU (1) | LU66250A1 (en, 2012) |
| NL (1) | NL7213559A (en, 2012) |
| NO (1) | NO137965C (en, 2012) |
| OA (1) | OA04193A (en, 2012) |
| PL (1) | PL89037B1 (en, 2012) |
| SE (1) | SE392896B (en, 2012) |
| SU (1) | SU505355A3 (en, 2012) |
| YU (2) | YU35365B (en, 2012) |
| ZA (1) | ZA726402B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2328346A1 (fr) * | 1975-10-17 | 1977-05-13 | Thomson Brandt | Dispositif transcodeur de signaux de television en couleurs |
| DE2837794A1 (de) | 1978-08-30 | 1980-03-13 | Asta Werke Ag Chem Fab | Basisch substituierte harnstoffe und thioharnstoffe, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| JPS6042795B2 (ja) * | 1978-10-23 | 1985-09-25 | 日本新薬株式会社 | カルバモイルピペラジン誘導体 |
| JPS56127369A (en) * | 1980-02-15 | 1981-10-06 | Mitsui Toatsu Chem Inc | Nevel piperazine compound, its preparation and utilization |
| JPS58140078A (ja) * | 1982-02-16 | 1983-08-19 | Nippon Tokushu Noyaku Seizo Kk | メチル置換テトラヒドロ−２−ピリミジノン誘導体、その製法、その中間体及び該中間体の製法、並びに除草剤 |
| JPS59176604U (ja) * | 1983-05-09 | 1984-11-26 | 株式会社 ケミカルマン | 溶剤回収用蒸留器 |
| JPS60108304U (ja) * | 1983-12-23 | 1985-07-23 | 株式会社 ケミカルマン | 溶剤回収器 |
| JPS60108302U (ja) * | 1983-12-23 | 1985-07-23 | 株式会社 ケミカルマン | 溶剤回収用蒸溜器 |
| JPS60143801A (ja) * | 1983-12-29 | 1985-07-30 | Kemikaruman:Kk | 溶剤類の回収方法 |
| US5496907A (en) * | 1993-03-02 | 1996-03-05 | H. B. Fuller Licensing & Financing, Inc. | Wet adhesion monomers with ureido functionality and polymers prepared therefrom |
| US5399706A (en) * | 1993-03-02 | 1995-03-21 | H. B. Fuller Licensing & Financing, Inc. | Imidazolidinone diamine and derivatives thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3374237A (en) * | 1965-05-21 | 1968-03-19 | American Cyanamid Co | 1-phenyl-3-(4-phenyl-1-piperazinoalkyl)-imidazolidinones and imidazolidinethiones |
| DE1695897C3 (de) * | 1966-07-04 | 1979-02-15 | Takeda Chemical Industries Ltd | N-Acyl-sydnonimine, deren Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| CH541568A (de) * | 1970-12-07 | 1973-10-31 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Imidazolidinonderivaten |
-
0
- BE BE789830D patent/BE789830A/xx unknown
-
1971
- 1971-10-09 DE DE2150438A patent/DE2150438C3/de not_active Expired
-
1972
- 1972-01-01 AR AR244518A patent/AR204390A1/es active
- 1972-09-19 IE IE1277/72A patent/IE36716B1/xx unknown
- 1972-09-19 ZA ZA726402A patent/ZA726402B/xx unknown
- 1972-09-20 CH CH1375872A patent/CH586220A5/xx not_active IP Right Cessation
- 1972-09-21 AT AT812072A patent/AT315834B/de not_active IP Right Cessation
- 1972-09-22 IL IL40411A patent/IL40411A/en unknown
- 1972-09-22 AU AU47000/72A patent/AU467578B2/en not_active Expired
- 1972-09-30 ES ES407203A patent/ES407203A1/es not_active Expired
- 1972-10-02 CU CU33794A patent/CU33794A/es unknown
- 1972-10-03 YU YU2484/72A patent/YU35365B/xx unknown
- 1972-10-03 US US294623A patent/US3919233A/en not_active Expired - Lifetime
- 1972-10-03 NO NO3522/72A patent/NO137965C/no unknown
- 1972-10-05 OA OA54712A patent/OA04193A/xx unknown
- 1972-10-06 LU LU66250A patent/LU66250A1/xx unknown
- 1972-10-06 PL PL1972158116A patent/PL89037B1/pl unknown
- 1972-10-06 DD DD166078A patent/DD101159A5/xx unknown
- 1972-10-06 FI FI2770/72A patent/FI57588C/fi active
- 1972-10-06 NL NL7213559A patent/NL7213559A/xx not_active Application Discontinuation
- 1972-10-06 GB GB4614172A patent/GB1359265A/en not_active Expired
- 1972-10-06 SE SE7212933A patent/SE392896B/xx unknown
- 1972-10-06 CA CA153,419A patent/CA980774A/en not_active Expired
- 1972-10-06 HU HUAA713A patent/HU165870B/hu unknown
- 1972-10-07 EG EG406/72A patent/EG11262A/xx active
- 1972-10-07 KR KR7201506A patent/KR780000046B1/ko not_active Expired
- 1972-10-09 FR FR7235692A patent/FR2157839B1/fr not_active Expired
- 1972-10-09 JP JP10147872A patent/JPS5728702B2/ja not_active Expired
- 1972-10-09 CS CS726803A patent/CS200165B2/cs unknown
- 1972-10-09 SU SU1835805A patent/SU505355A3/ru active
-
1977
- 1977-10-06 HK HK517/77A patent/HK51777A/xx unknown
-
1979
- 1979-06-27 YU YU1527/79A patent/YU35594B/xx unknown
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