NO119949B - - Google Patents
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- Publication number
- NO119949B NO119949B NO692317A NO231769A NO119949B NO 119949 B NO119949 B NO 119949B NO 692317 A NO692317 A NO 692317A NO 231769 A NO231769 A NO 231769A NO 119949 B NO119949 B NO 119949B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- imidazolin
- formula
- carbanilide
- addition salts
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- HCJAVYDERMMIDO-UHFFFAOYSA-N 3-(4,5-dihydro-1h-imidazol-2-yl)aniline Chemical compound NC1=CC=CC(C=2NCCN=2)=C1 HCJAVYDERMMIDO-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 201000008680 babesiosis Diseases 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
- 208000015181 infectious disease Diseases 0.000 description 3
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- 241000606646 Anaplasma Species 0.000 description 2
- 241000223836 Babesia Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000223777 Theileria Species 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- KRUVSRGJKCHYMY-UHFFFAOYSA-N 1,3-bis(3-carbamimidoylphenyl)urea Chemical compound NC(=N)C1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C(N)=N)=C1 KRUVSRGJKCHYMY-UHFFFAOYSA-N 0.000 description 1
- NGGVLMZISOGVOE-UHFFFAOYSA-N 1,3-bis(3-cyanophenyl)urea Chemical compound C=1C=CC(C#N)=CC=1NC(=O)NC1=CC=CC(C#N)=C1 NGGVLMZISOGVOE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000223840 Babesia bigemina Species 0.000 description 1
- 241001455947 Babesia divergens Species 0.000 description 1
- 206010003964 Babesia infections Diseases 0.000 description 1
- 241000223774 Babesia rodhaini Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000223834 Piroplasmida Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 241000223779 Theileria parva Species 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- XXCIDEQIWQKILU-UHFFFAOYSA-M sodium;urea;acetate Chemical compound [Na+].CC([O-])=O.NC(N)=O XXCIDEQIWQKILU-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000001549 tubercolostatic effect Effects 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
- C07D239/06—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- 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
- C07D233/20—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 substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Description
Fremgangsmåte for fremstilling av et terapeutisk virksomt diimidazolinyl-karbanilid.
Oppfinnelsen vedrører en fremgangsmåte for fremstilling av 3,3<1->di-2-imidazolin-2-yl-karbanilid av formelen:
såmt syreaddisjonssalter av dette. 3,3'-di-2-imidazolin-2-yl-karbanilidet av formel I oppnås ved omsetning av 3-(2-imidazolin-2-yl)-anilin av formelen:
med karbonsyre, respektive med et reaktivt karbonsyrederivat, f.eks. fosgen.
S^-di^-imidazolin^-yl-karbanilidet av formel I oppnås videre ved omsetning av en forbindelse av formelen:
med etylendiamin.
3,3'-di-2-imidazolin-2-yl-karbanilidet av formel I kan oppnås som fri base eller i form av et salt med en egnet uorganisk eller organisk syre. Som mulige salter nevnes salter av svovelsyre, saltsyre, bromhydrogensyre, jodhydrogensyre, fosforsyre, maursyre, eddiksyre, propionsyre, smorsyre, vinsyre, maleinsyre, oksalsyre, sitronsyre, salicylsyre og lignende.
3,3'-di-2-imidazolin-2-yl-karbanilid, såvel som dets syreaddisjonssalter er nye forbindelser som på grunn av sine farmakodynamiske virkninger fremfor alt egner seg som kemo-terapeutika, spesielt som tuberkulostatika, og også for behand-ling av dyr som er infisert med piroplasmider, såsom babesia, theileria og anapl^sma.
Det er kjent at 3,3<*->diamidino-karbanilid og dets syreaddisjonssalter er virksomme ved bekjempelse av infeksjoner hos dyr, som er forårsaket av protozoer av babesia-familien, såsom babesia-divergens, babesia-bigemina og babesia-rodhaini. ;3,3'-di-2-imidazolin-2-yl-karbanilid og dets syreaddisjonssalter er ved bekjempelse av babesia-infeksjoner like virksomme eller enda mer virksomme enn det tidligere kjente 3,3'-diamidino-karbanilid og dets syreaddisjonssalter, men er - i motsetning til 3,3"-diamidino-karbanilid - også virksomme mot andre piroplasmlda-infeksjoner, f.eks. ved infeksjoner som er forårsaket av theileria, f.eks. theileria-parva, og anaplasma, f.eks. anaplasma-marginate. ;Eksempel 1 ;15 g 3-(2-imidazolin-2-yl)*anllin-dihydrogenklorid og 30 g natriuraacetat loses i 150 ml vann. Fosgen ledes inn i losningen under god omroring til diazo-prSven er negativ. Basen som danner seg» frigjores med natronLut, knuses og skiLles fra med nutsche. Resten vaskes med vann og loses i fortynnet eddiksyre. Losningen klares med kull, tilsettes konsentrert saltsyre og podes. Det skiller seg ut krystaller som etter avkjoling til 0°C filtreres av med nutsche og vaskes fem ganger med 10 7o saltsyre og deretter med alkohol og eter. Etter tork-ing i vakuum ved 50°G fås 15 g 3,3'-di-2-imidazolin-2-yl-karbanilid-dihydrogenklorid med smeltepunkt 350°C (under spalt-ing).
Eksempel 2
43 g av det i henhold til nedenstående oppnådde N,N'-di-(m-iminoetyleter)-urinstoff loses i 150 ml absolutt etanol. Deretter tilsettes 20 ml etylendiamin, og det oppvarmes i lopet av 8 timer til 60-70°C. Reaksjonsblandingen dampes inn, inn-dampningsresten loses i 100 ml vann, og den vandige losning tilsettes overskudd av sodalosning. Det utskilte, basiske produkt filtreres av ved hjelp av nutsche, vaskes med vann og loses i fortynnet eddiksyre. Den eddiksure losning klares med kull og tilsettes overskudd av saltsyre. Det avkjoles til 0°C, det utskilte hydrogenklorid filtreres av ved hjelp av nutsche og vaskes, forst med 10 % saltsyre og deretter med etanol og eter. Etter torkingen fås 36 g 3,3'-di-2-imidazolin-2-yl-karbanilid-dihydrogenklorid med spaltningspunkt 350°C, som er identisk med det i henhold til eksempel 1 oppnådde produkt.
Det i dette eksempel anvendte utgangsstoff oppnås på folgende måte.
Til en suspensjon av 26,2 g N,N'-di-(m-cyanofenyl)-urin-stoff i 300 ml vannfri kloroform tilsettes 50 ml vannfri etanol som er mettet med klorhydrogengass, og dette får stå ved rom-temperatur i 5 dager. Det oppståtte krystalliserte materiale filtreres med nutsche, vaskes med vannfri eter og torkes. Det oppnås 43 g N,N'-d-(m-iminoetyleter)-urinstoff som anvendes videre direkte og uten ytterligere rensning.
Claims (1)
- Fremgangsmåte for fremstilling av det terapeutisk virksomme 3,3'-di-2-imidazolin-2-yl-karbanilid av formelen:samt syreaddisjonssalter av dette, karakterisert ved at a) 3-(2-imidazolin-2-yl)-anilin av formelen:omsettes med karbonsyre, respektive et reaktivt karbonsyrederivat, eller at b) en forbindelse av formelen:hvor A betyr gruppenomsettes med etylendiamin,hvoretter det oppnådde reaksjonsprodukt isoleres i form av den frie base eller et addisjonssalt med en egnet uorganisk eller organisk syre.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1154760 | 1960-10-14 | ||
| CH261761 | 1961-03-03 | ||
| CH305961 | 1961-03-14 | ||
| CH391961 | 1961-04-04 | ||
| CH496661 | 1961-04-28 | ||
| CH720161 | 1961-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO119949B true NO119949B (no) | 1970-08-03 |
Family
ID=27543682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO692317A NO119949B (no) | 1960-10-14 | 1969-06-04 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3338917A (no) |
| DE (1) | DE1445186C3 (no) |
| DK (1) | DK119352B (no) |
| FR (1) | FR1464M (no) |
| GB (1) | GB1007334A (no) |
| MX (1) | MX3465E (no) |
| NL (1) | NL139886B (no) |
| NO (1) | NO119949B (no) |
| OA (1) | OA01084A (no) |
| SE (2) | SE335975B (no) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE757956A (fr) * | 1969-10-24 | 1971-04-23 | Ici Ltd | Composes antiviraux |
| BE757955A (fr) * | 1969-10-24 | 1971-04-23 | Ici Ltd | Compositions antivirales |
| WO1995032945A1 (en) * | 1994-06-01 | 1995-12-07 | Arris Pharmaceutical Corporation | Compositions and methods for treating mast-cell mediated conditions |
| US5633388A (en) * | 1996-03-29 | 1997-05-27 | Viropharma Incorporated | Compounds, compositions and methods for treatment of hepatitis C |
| EP1264820A4 (en) * | 2000-03-14 | 2004-09-15 | Fujisawa Pharmaceutical Co | amide compounds |
| EP1395548A1 (en) | 2001-02-26 | 2004-03-10 | 4Sc Ag | Derivatives of diphenylurea, diphenyloxalic acid diamide and diphenylsulfuric acid diamide and their use as medicaments |
| CN100390150C (zh) * | 2006-06-05 | 2008-05-28 | 吴汝林 | 盐酸咪唑苯脲的制备方法 |
| EP2446074A1 (en) | 2009-06-25 | 2012-05-02 | Texas Research International, Inc. | Novel polyurea fiber |
| CN102898375B (zh) * | 2012-11-13 | 2015-07-22 | 齐鲁动物保健品有限公司 | 一种2-(3-氨基苯基)咪唑啉盐酸盐的制备方法 |
| WO2014089226A1 (en) * | 2012-12-04 | 2014-06-12 | The Board Of Trustees Of The University Of Illinois | Antibacterial compounds targeting isoprenoid biosynthesis |
| CN103896843B (zh) * | 2014-04-17 | 2016-02-24 | 山东久隆精细化工有限公司 | 一种咪唑苯脲的制备方法 |
| CN113924289A (zh) * | 2019-07-12 | 2022-01-11 | 日本化药株式会社 | 发光性化合物或其盐，以及含有该化合物的偏光发光元件、偏光发光板及显示装置 |
| WO2022249192A1 (en) * | 2021-05-27 | 2022-12-01 | Ramot At Tel-Aviv University Ltd. | Broad-spectrum metastasis suppressing compounds and therapeutic uses thereof in human tumors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2473577A (en) * | 1945-05-28 | 1949-06-21 | Petrolite Corp | Carbonic acid amides of certain substituted glyoxalidines |
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1961
- 1961-09-27 MX MX004244U patent/MX3465E/es unknown
- 1961-10-02 DE DE1445186A patent/DE1445186C3/de not_active Expired
- 1961-10-12 DK DK405761AA patent/DK119352B/da unknown
- 1961-10-12 NL NL61270189A patent/NL139886B/xx unknown
- 1961-10-12 GB GB36662/61A patent/GB1007334A/en not_active Expired
- 1961-10-13 FR FR875918A patent/FR1464M/fr active Active
-
1964
- 1964-12-28 SE SE15703/64A patent/SE335975B/xx unknown
- 1964-12-28 SE SE15704/64A patent/SE329151B/xx unknown
- 1964-12-30 OA OA51192A patent/OA01084A/xx unknown
-
1966
- 1966-12-06 US US599391A patent/US3338917A/en not_active Expired - Lifetime
-
1969
- 1969-06-04 NO NO692317A patent/NO119949B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE335975B (no) | 1971-06-21 |
| DE1445186B2 (de) | 1974-03-28 |
| DK119352B (da) | 1970-12-21 |
| MX3465E (es) | 1980-09-12 |
| DE1445186C3 (de) | 1974-11-07 |
| NL139886B (nl) | 1973-10-15 |
| FR1464M (fr) | 1962-08-27 |
| SE329151B (no) | 1970-10-05 |
| DE1445186A1 (de) | 1968-10-24 |
| OA01084A (fr) | 1968-08-07 |
| GB1007334A (en) | 1965-10-13 |
| US3338917A (en) | 1967-08-29 |
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