DE2518032A1 - 2-aminoimidazole, verfahren zu deren herstellung und dieselben enthaltendes mittel - Google Patents
2-aminoimidazole, verfahren zu deren herstellung und dieselben enthaltendes mittelInfo
- Publication number
- DE2518032A1 DE2518032A1 DE19752518032 DE2518032A DE2518032A1 DE 2518032 A1 DE2518032 A1 DE 2518032A1 DE 19752518032 DE19752518032 DE 19752518032 DE 2518032 A DE2518032 A DE 2518032A DE 2518032 A1 DE2518032 A1 DE 2518032A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- alkyl
- formula
- phenyl
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 17
- DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 7
- -1 alkyl radical Chemical class 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 150000002460 imidazoles Chemical class 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical class NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical class NCC=O LYIIBVSRGJSHAV-UHFFFAOYSA-N 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- RYTLGWCJESCDMY-UHFFFAOYSA-N carbamimidoyl chloride Chemical compound NC(Cl)=N RYTLGWCJESCDMY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002542 isoureas Chemical class 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000007958 sleep Effects 0.000 description 4
- LDHNCFASIAVKBC-UHFFFAOYSA-N 5-methyl-n,1-diphenylimidazol-2-amine Chemical compound C=1C=CC=CC=1N1C(C)=CN=C1NC1=CC=CC=C1 LDHNCFASIAVKBC-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 239000008177 pharmaceutical agent Substances 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 230000002582 psychostimulating effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 2
- WTWDYIRAELZONQ-UHFFFAOYSA-N 5-methyl-1-phenylimidazole Chemical compound CC1=CN=CN1C1=CC=CC=C1 WTWDYIRAELZONQ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
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- 239000004202 carbamide Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
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- 238000002316 cosmetic surgery Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
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- 230000004054 inflammatory process Effects 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
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- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical group CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- ZAZDOUVATXGMAH-UHFFFAOYSA-N n-(5-methyl-1-phenylimidazol-2-yl)-n-phenylacetamide Chemical compound C=1C=CC=CC=1N(C(=O)C)C1=NC=C(C)N1C1=CC=CC=C1 ZAZDOUVATXGMAH-UHFFFAOYSA-N 0.000 description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ONEYFZXGNFNRJH-UHFFFAOYSA-N 1-(4-methylphenyl)piperazine Chemical compound C1=CC(C)=CC=C1N1CCNCC1 ONEYFZXGNFNRJH-UHFFFAOYSA-N 0.000 description 1
- JDJMOABHGXMDHI-UHFFFAOYSA-N 1-butyl-n-methyl-n-phenylimidazol-2-amine Chemical compound CCCCN1C=CN=C1N(C)C1=CC=CC=C1 JDJMOABHGXMDHI-UHFFFAOYSA-N 0.000 description 1
- UGOQKSGJGCADAG-UHFFFAOYSA-N 1-prop-2-ynylimidazole Chemical compound C#CCN1C=CN=C1 UGOQKSGJGCADAG-UHFFFAOYSA-N 0.000 description 1
- CPTAEJISPBQEKA-UHFFFAOYSA-N 2-pyrrolidin-1-yl-1h-imidazole Chemical compound C1CCCN1C1=NC=CN1 CPTAEJISPBQEKA-UHFFFAOYSA-N 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- BEOBXTDVIVBDRJ-UHFFFAOYSA-N n,1,5-trimethyl-n-phenylimidazol-2-amine Chemical compound C=1C=CC=CC=1N(C)C1=NC=C(C)N1C BEOBXTDVIVBDRJ-UHFFFAOYSA-N 0.000 description 1
- MIHYJUHKZDDNNA-UHFFFAOYSA-N n,1-bis(4-chlorophenyl)-5-methylimidazol-2-amine Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=CN=C1NC1=CC=C(Cl)C=C1 MIHYJUHKZDDNNA-UHFFFAOYSA-N 0.000 description 1
- INNKSVOGHPUZCA-UHFFFAOYSA-N n,1-bis(4-chlorophenyl)imidazol-2-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NC=CN1C1=CC=C(Cl)C=C1 INNKSVOGHPUZCA-UHFFFAOYSA-N 0.000 description 1
- QDKCALOYGIYXOX-UHFFFAOYSA-N n,1-bis(4-methoxyphenyl)imidazol-2-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC=CN1C1=CC=C(OC)C=C1 QDKCALOYGIYXOX-UHFFFAOYSA-N 0.000 description 1
- GTMKNJCXZVQYKC-UHFFFAOYSA-N n,1-dimethyl-n-phenylimidazol-2-amine Chemical compound C=1C=CC=CC=1N(C)C1=NC=CN1C GTMKNJCXZVQYKC-UHFFFAOYSA-N 0.000 description 1
- YZCLOPGTTDUJPI-UHFFFAOYSA-N n,1-diphenylimidazol-2-amine Chemical compound C=1C=CC=CC=1NC1=NC=CN1C1=CC=CC=C1 YZCLOPGTTDUJPI-UHFFFAOYSA-N 0.000 description 1
- RWRKBXYOFYDYHQ-UHFFFAOYSA-N n-benzyl-n-methyl-1-phenylimidazol-2-amine Chemical compound N=1C=CN(C=2C=CC=CC=2)C=1N(C)CC1=CC=CC=C1 RWRKBXYOFYDYHQ-UHFFFAOYSA-N 0.000 description 1
- UCNYRXUKTKQWGG-UHFFFAOYSA-N n-phenyl-n-(1-phenylimidazol-2-yl)acetamide Chemical compound C=1C=CC=CC=1N(C(=O)C)C1=NC=CN1C1=CC=CC=C1 UCNYRXUKTKQWGG-UHFFFAOYSA-N 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000793 phophlogistic effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000021317 sensory perception Effects 0.000 description 1
- 230000004617 sleep duration Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7414986A FR2269341B1 (en, 2012) | 1974-04-30 | 1974-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2518032A1 true DE2518032A1 (de) | 1975-11-20 |
Family
ID=9138307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752518032 Withdrawn DE2518032A1 (de) | 1974-04-30 | 1975-04-23 | 2-aminoimidazole, verfahren zu deren herstellung und dieselben enthaltendes mittel |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3995050A (en, 2012) |
| JP (1) | JPS50157366A (en, 2012) |
| BE (1) | BE827613A (en, 2012) |
| CA (1) | CA1057287A (en, 2012) |
| CH (1) | CH611281A5 (en, 2012) |
| DE (1) | DE2518032A1 (en, 2012) |
| ES (1) | ES436864A1 (en, 2012) |
| FR (1) | FR2269341B1 (en, 2012) |
| GB (1) | GB1499544A (en, 2012) |
| HU (1) | HU171325B (en, 2012) |
| NL (1) | NL7504435A (en, 2012) |
| PL (1) | PL94923B1 (en, 2012) |
| RO (1) | RO68749A (en, 2012) |
| SU (1) | SU552026A3 (en, 2012) |
| YU (1) | YU104475A (en, 2012) |
| ZA (1) | ZA752339B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2358890A1 (fr) * | 1976-05-24 | 1978-02-17 | Science Union & Cie | Nouvelles aryl trifluoroethylamines, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
| FI792511A7 (fi) * | 1978-08-16 | 1981-01-01 | Farmos Oy | Menetelmä terapeuttisia ominaisuuksia omaavien kemiallisten yhdisteiden valmistamiseksi. |
| US5258381A (en) * | 1984-03-19 | 1993-11-02 | The Rockefeller University | 2-substituted-2-imidazolines |
| JPH0625148B2 (ja) * | 1987-05-31 | 1994-04-06 | 日本合成化学工業株式会社 | ２−アミノイミダゾ−ルまたはその塩の製造法 |
| US5922751A (en) * | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| DE19514579A1 (de) * | 1995-04-20 | 1996-10-24 | Boehringer Ingelheim Kg | Verwendung von alpha¶1¶¶L¶-Agonisten zur Behandlung der Harninkontinenz |
| JP4445262B2 (ja) * | 2001-10-09 | 2010-04-07 | アムジェン インコーポレイテッド | 抗炎症剤としてのイミダゾール誘導体 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459763A (en) * | 1966-01-25 | 1969-08-05 | Geigy Chem Corp | Certain amino imidazole derivatives |
-
1974
- 1974-04-30 FR FR7414986A patent/FR2269341B1/fr not_active Expired
-
1975
- 1975-04-07 BE BE155130A patent/BE827613A/xx unknown
- 1975-04-11 ZA ZA752339A patent/ZA752339B/xx unknown
- 1975-04-15 NL NL7504435A patent/NL7504435A/xx not_active Application Discontinuation
- 1975-04-15 US US05/568,362 patent/US3995050A/en not_active Expired - Lifetime
- 1975-04-17 CA CA224,835A patent/CA1057287A/en not_active Expired
- 1975-04-23 ES ES436864A patent/ES436864A1/es not_active Expired
- 1975-04-23 DE DE19752518032 patent/DE2518032A1/de not_active Withdrawn
- 1975-04-24 YU YU01044/75A patent/YU104475A/xx unknown
- 1975-04-25 HU HU75PA00001213A patent/HU171325B/hu unknown
- 1975-04-29 SU SU2130096A patent/SU552026A3/ru active
- 1975-04-29 RO RO7582121A patent/RO68749A/ro unknown
- 1975-04-29 GB GB17835/75A patent/GB1499544A/en not_active Expired
- 1975-04-29 CH CH548675A patent/CH611281A5/xx not_active IP Right Cessation
- 1975-04-29 PL PL1975180052A patent/PL94923B1/pl unknown
- 1975-04-30 JP JP50052467A patent/JPS50157366A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HU171325B (hu) | 1977-12-28 |
| FR2269341A1 (en, 2012) | 1975-11-28 |
| ES436864A1 (es) | 1976-12-01 |
| YU104475A (en) | 1983-04-27 |
| GB1499544A (en) | 1978-02-01 |
| CA1057287A (en) | 1979-06-26 |
| BE827613A (fr) | 1975-07-31 |
| RO68749A (ro) | 1980-01-15 |
| JPS50157366A (en, 2012) | 1975-12-19 |
| NL7504435A (nl) | 1975-11-03 |
| FR2269341B1 (en, 2012) | 1978-07-28 |
| ZA752339B (en) | 1976-11-24 |
| SU552026A3 (ru) | 1977-03-25 |
| PL94923B1 (en, 2012) | 1977-09-30 |
| CH611281A5 (en, 2012) | 1979-05-31 |
| US3995050A (en) | 1976-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |