DE2634430A1 - Harnstoffderivate, ihre salze mit saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
Harnstoffderivate, ihre salze mit saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE2634430A1 DE2634430A1 DE19762634430 DE2634430A DE2634430A1 DE 2634430 A1 DE2634430 A1 DE 2634430A1 DE 19762634430 DE19762634430 DE 19762634430 DE 2634430 A DE2634430 A DE 2634430A DE 2634430 A1 DE2634430 A1 DE 2634430A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- group
- methyl
- imidazolyl
- hydroxymethyl
- 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- Withdrawn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
- 150000001875 compounds Chemical class 0.000 title claims description 41
- 239000002253 acid Substances 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 9
- 150000007513 acids Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 229940126601 medicinal product Drugs 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title 1
- -1 imidazolyl- Chemical group 0.000 claims description 49
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 36
- 229960001340 histamine Drugs 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 150000002460 imidazoles Chemical class 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 150000003672 ureas Chemical class 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 239000003087 receptor blocking agent Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 7
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229940125715 antihistaminic agent Drugs 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 3
- 229960000582 mepyramine Drugs 0.000 description 3
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- KYHBSTURXRCUEW-UHFFFAOYSA-N 2-[(2-methyl-1h-imidazol-5-yl)sulfanyl]ethanamine Chemical compound CC1=NC=C(SCCN)N1 KYHBSTURXRCUEW-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000009858 acid secretion Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- BJERXDWXCSKSCV-UHFFFAOYSA-N ethyl 5-(ethoxymethyl)-1h-imidazole-4-carboxylate Chemical compound CCOCC=1NC=NC=1C(=O)OCC BJERXDWXCSKSCV-UHFFFAOYSA-N 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 210000005245 right atrium Anatomy 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 1
- SODVIWFIWHJBNS-UHFFFAOYSA-N 1H-imidazole dihydrobromide Chemical compound Br.Br.C1=CNC=N1 SODVIWFIWHJBNS-UHFFFAOYSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- GMEDUXHKSSWXSL-UHFFFAOYSA-N 3-sulfanylpropylazanium;chloride Chemical compound Cl.NCCCS GMEDUXHKSSWXSL-UHFFFAOYSA-N 0.000 description 1
- VJSUMPPMFYQOMP-UHFFFAOYSA-N 4-(1h-imidazol-5-yl)butan-1-amine Chemical compound NCCCCC1=CNC=N1 VJSUMPPMFYQOMP-UHFFFAOYSA-N 0.000 description 1
- YGRKKKIDGHTEHL-UHFFFAOYSA-N 5-(hydroxymethyl)-1h-imidazole-4-carboxylic acid Chemical compound OCC=1NC=NC=1C(O)=O YGRKKKIDGHTEHL-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- XHAJXIIIXSELER-UHFFFAOYSA-N CC1=C(C(=NC=C1)SCCN)Cl Chemical compound CC1=C(C(=NC=C1)SCCN)Cl XHAJXIIIXSELER-UHFFFAOYSA-N 0.000 description 1
- BLGAGUAMDOVFNM-UHFFFAOYSA-N CC1=C(C(=NC=C1)SCCN)OC Chemical compound CC1=C(C(=NC=C1)SCCN)OC BLGAGUAMDOVFNM-UHFFFAOYSA-N 0.000 description 1
- SVXQBURXRIUSRP-UHFFFAOYSA-N CCOCC1=CNC(=S)N1 Chemical compound CCOCC1=CNC(=S)N1 SVXQBURXRIUSRP-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
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- 108010010803 Gelatin Proteins 0.000 description 1
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- 229920000084 Gum arabic Polymers 0.000 description 1
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- 239000002841 Lewis acid Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
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- 108010079943 Pentagastrin Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
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- 208000001871 Tachycardia Diseases 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- NMFFBRFOLVKNGJ-UHFFFAOYSA-N [4-(2-aminoethylsulfanyl)-2-methyl-1H-imidazol-5-yl]methanol Chemical compound OCC1=C(N=C(N1)C)SCCN NMFFBRFOLVKNGJ-UHFFFAOYSA-N 0.000 description 1
- FADXNKNUTLLOJL-UHFFFAOYSA-N [4-(4-aminobutyl)-1H-imidazol-5-yl]methanol Chemical compound OCC1=C(N=CN1)CCCCN FADXNKNUTLLOJL-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
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- 239000004480 active ingredient Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
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- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 1
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- 125000004494 ethyl ester group Chemical group 0.000 description 1
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- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
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- 238000004809 thin layer chromatography Methods 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- AFNRRBXCCXDRPS-UHFFFAOYSA-N tin(ii) sulfide Chemical compound [Sn]=S AFNRRBXCCXDRPS-UHFFFAOYSA-N 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
- 210000004291 uterus Anatomy 0.000 description 1
- 230000000304 vasodilatating effect Effects 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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 |
|---|---|---|---|
| GB31968/75A GB1565647A (en) | 1975-07-31 | 1975-07-31 | Pharmacologically active compounds 4-substituted-imidazole-5-methanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2634430A1 true DE2634430A1 (de) | 1977-02-10 |
Family
ID=10331071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762634430 Withdrawn DE2634430A1 (de) | 1975-07-31 | 1976-07-30 | Harnstoffderivate, ihre salze mit saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (28)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| GR62452B (en) | 1977-04-20 | 1979-04-12 | Ici Ltd | Preparation process of guanidine derivatives |
| US4112234A (en) | 1977-08-22 | 1978-09-05 | Bristol-Myers Company | Imidazolylmethylthioethyl alkynyl guanidines |
| USRE31588E (en) * | 1977-06-03 | 1984-05-22 | Bristol-Myers Company | Imidazolylmethylthioethyl alkynyl guanidines |
| US4233302A (en) | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
| EP0008596A1 (fr) * | 1978-09-04 | 1980-03-19 | DEVINTER Europe S.A. Société anonyme dite: | Procédé de préparation de dérivés du type 4-hydroxyméthyl imidazole à partir d'esters d'acides 4-imidazole carboxyliques correspondants |
| US4200760A (en) * | 1978-09-26 | 1980-04-29 | Bristol-Myers Company | Imidazolylalkylthioalkylamino-ethylene derivatives |
| JPS5914460B2 (ja) * | 1978-12-27 | 1984-04-04 | 相互薬工株式会社 | Ｈ↓２受容体「きつ」抗剤シメチジンの製造法 |
| EP0014057B1 (en) | 1979-01-18 | 1985-01-02 | Imperial Chemical Industries Plc | Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| CN103288742A (zh) * | 2013-06-04 | 2013-09-11 | 四川百利药业有限责任公司 | 一种高纯度英加韦林原料的制备方法 |
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA938556A (en) * | 1970-06-25 | 1973-12-18 | Smith Kline And French Laboratories Limited | Pharmaceutical compositions containing thiourea derivatives |
-
1975
- 1975-07-31 GB GB31968/75A patent/GB1565647A/en not_active Expired
-
1976
- 1976-06-21 ZA ZA763686A patent/ZA763686B/xx unknown
- 1976-07-06 BE BE168682A patent/BE843840A/xx not_active IP Right Cessation
- 1976-07-09 IL IL50006A patent/IL50006A0/xx unknown
- 1976-07-09 PH PH18667A patent/PH13417A/en unknown
- 1976-07-13 DK DK316376A patent/DK316376A/da unknown
- 1976-07-16 PT PT65377A patent/PT65377B/pt unknown
- 1976-07-20 FR FR7622069A patent/FR2319341A1/fr active Granted
- 1976-07-21 CS CS764839A patent/CS203054B2/cs unknown
- 1976-07-22 CA CA257,589A patent/CA1075702A/en not_active Expired
- 1976-07-23 ZM ZM96/76A patent/ZM9676A1/xx unknown
- 1976-07-27 GR GR51356A patent/GR61114B/el unknown
- 1976-07-27 AT AT552376A patent/AT356668B/de not_active IP Right Cessation
- 1976-07-27 SE SE7608478A patent/SE7608478L/xx unknown
- 1976-07-29 LU LU75495A patent/LU75495A1/xx unknown
- 1976-07-30 SU SU762386215A patent/SU655310A3/ru active
- 1976-07-30 DE DE19762634430 patent/DE2634430A1/de not_active Withdrawn
- 1976-07-30 DD DD194154A patent/DD125205A5/xx unknown
- 1976-07-30 HU HU76SI1532A patent/HU174068B/hu unknown
- 1976-07-30 FI FI762191A patent/FI762191A7/fi not_active Application Discontinuation
- 1976-07-30 AR AR264157A patent/AR213100A1/es active
- 1976-07-30 ES ES450309A patent/ES450309A1/es not_active Expired
- 1976-07-30 NL NL7608505A patent/NL7608505A/xx not_active Application Discontinuation
- 1976-07-30 JP JP51092242A patent/JPS5219663A/ja active Pending
- 1976-07-30 AU AU16447/76A patent/AU508262B2/en not_active Expired
- 1976-07-30 NO NO762659A patent/NO762659L/no unknown
- 1976-07-31 OA OA55903A patent/OA05405A/xx unknown
- 1976-07-31 RO RO87167A patent/RO72312B/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO762659L (enrdf_load_stackoverflow) | 1977-02-01 |
| BE843840A (fr) | 1977-01-06 |
| ES450309A1 (es) | 1977-12-01 |
| RO72312B (ro) | 1984-03-31 |
| GR61114B (en) | 1978-09-13 |
| IL50006A0 (en) | 1976-09-30 |
| LU75495A1 (enrdf_load_stackoverflow) | 1977-03-03 |
| AR213100A1 (es) | 1978-12-15 |
| DD125205A5 (enrdf_load_stackoverflow) | 1977-04-06 |
| SE7608478L (sv) | 1977-02-01 |
| JPS5219663A (en) | 1977-02-15 |
| PT65377A (en) | 1976-08-01 |
| PH13417A (en) | 1980-03-30 |
| ATA552376A (de) | 1979-10-15 |
| DK316376A (da) | 1977-02-01 |
| ZA763686B (en) | 1977-05-25 |
| FR2319341B1 (enrdf_load_stackoverflow) | 1979-01-12 |
| FR2319341A1 (fr) | 1977-02-25 |
| OA05405A (fr) | 1981-02-28 |
| CS203054B2 (en) | 1981-02-27 |
| CA1075702A (en) | 1980-04-15 |
| SU655310A3 (ru) | 1979-03-30 |
| HU174068B (hu) | 1979-10-28 |
| NL7608505A (nl) | 1977-02-02 |
| GB1565647A (en) | 1980-04-23 |
| AU1644776A (en) | 1978-02-02 |
| ZM9676A1 (en) | 1977-07-21 |
| FI762191A7 (enrdf_load_stackoverflow) | 1977-02-01 |
| AT356668B (de) | 1980-05-12 |
| PT65377B (en) | 1978-01-19 |
| AU508262B2 (en) | 1980-03-13 |
| RO72312A (ro) | 1984-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |