PL100317B1 - Sposob wytwarzania nowych pochodnych amidyny - Google Patents
Sposob wytwarzania nowych pochodnych amidyny Download PDFInfo
- Publication number
- PL100317B1 PL100317B1 PL1975178679A PL17867975A PL100317B1 PL 100317 B1 PL100317 B1 PL 100317B1 PL 1975178679 A PL1975178679 A PL 1975178679A PL 17867975 A PL17867975 A PL 17867975A PL 100317 B1 PL100317 B1 PL 100317B1
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- PL
- Poland
- Prior art keywords
- formula
- methyl
- group
- ethyl
- solution
- Prior art date
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- 150000001409 amidines Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229960001340 histamine Drugs 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 6
- 102000003710 Histamine H2 Receptors Human genes 0.000 claims description 6
- 108090000050 Histamine H2 Receptors Proteins 0.000 claims description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 102000005962 receptors Human genes 0.000 claims description 6
- 108020003175 receptors Proteins 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000739 antihistaminic agent Substances 0.000 claims description 4
- 229940125715 antihistaminic agent Drugs 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
- RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- 229960000582 mepyramine Drugs 0.000 claims description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
- 239000005557 antagonist Substances 0.000 claims description 2
- 230000031018 biological processes and functions Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 20
- 239000000243 solution Substances 0.000 claims 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 9
- 239000000460 chlorine Substances 0.000 claims 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 6
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 claims 5
- 241000700159 Rattus Species 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 5
- 239000007787 solid Substances 0.000 claims 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- 239000004480 active ingredient Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000007788 liquid Substances 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 239000007937 lozenge Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 2
- CIGPGCNMPFKLRK-UHFFFAOYSA-N 2-methyl-1,3-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound N1=CNC(C)=C1CSCCNC(=NC)NCCSCC=1N=CNC=1C CIGPGCNMPFKLRK-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims 2
- 241000700199 Cavia porcellus Species 0.000 claims 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- -1 N- [2- (5-Methyl-4-imidazolylmethylthio) ethyl] -4-hydroxybenzamidine dihydrochloride 4-Cyanophenol Chemical compound 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 2
- 230000027119 gastric acid secretion Effects 0.000 claims 2
- 229920000159 gelatin Polymers 0.000 claims 2
- 235000019322 gelatine Nutrition 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 210000002837 heart atrium Anatomy 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 2
- 150000002463 imidates Chemical class 0.000 claims 2
- 239000003456 ion exchange resin Substances 0.000 claims 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 239000006188 syrup Substances 0.000 claims 2
- 235000020357 syrup Nutrition 0.000 claims 2
- 150000003852 triazoles Chemical group 0.000 claims 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims 1
- HWMIWSNVUUVQNE-UHFFFAOYSA-N 1,2-dimethyl-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine;dihydrochloride Chemical compound Cl.Cl.CNC(=NC)NCCSCC=1N=CNC=1C HWMIWSNVUUVQNE-UHFFFAOYSA-N 0.000 claims 1
- BOPZDXATCGECMU-UHFFFAOYSA-N 4-n-[2-(4-aminoanilino)ethyl]benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NCCNC1=CC=C(N)C=C1 BOPZDXATCGECMU-UHFFFAOYSA-N 0.000 claims 1
- 229920001817 Agar Polymers 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- 108010010803 Gelatin Proteins 0.000 claims 1
- 239000001828 Gelatine Substances 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
- 240000007472 Leucaena leucocephala Species 0.000 claims 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 claims 1
- 235000019483 Peanut oil Nutrition 0.000 claims 1
- NEYNJQRKHLUJRU-DZUOILHNSA-N Pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 NEYNJQRKHLUJRU-DZUOILHNSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- 239000008272 agar Substances 0.000 claims 1
- 235000010419 agar Nutrition 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- FWRPUWOMIWLQKH-UHFFFAOYSA-N benzenecarboximidamide;dihydrochloride Chemical compound Cl.Cl.NC(=N)C1=CC=CC=C1 FWRPUWOMIWLQKH-UHFFFAOYSA-N 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 claims 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 claims 1
- 239000012259 ether extract Substances 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 235000013305 food Nutrition 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000008273 gelatin Substances 0.000 claims 1
- 239000007903 gelatin capsule Substances 0.000 claims 1
- 235000011852 gelatine desserts Nutrition 0.000 claims 1
- 230000027125 histamine-induced gastric acid secretion Effects 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 230000007794 irritation Effects 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 239000006194 liquid suspension Substances 0.000 claims 1
- 235000019359 magnesium stearate Nutrition 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- BXXGTPDBOUVLLF-UHFFFAOYSA-N methyl n,n'-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;trihydrochloride Chemical compound Cl.Cl.Cl.N1=CNC(C)=C1CSCCN=C(SC)NCCSCC=1N=CNC=1C BXXGTPDBOUVLLF-UHFFFAOYSA-N 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- DDGLNLPHGFZESB-UHFFFAOYSA-N n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]benzenecarboximidamide;dihydrochloride Chemical compound Cl.Cl.N1C=NC(CSCCNC(=N)C=2C=CC=CC=2)=C1C DDGLNLPHGFZESB-UHFFFAOYSA-N 0.000 claims 1
- CHJKZRRKIUZHLF-UHFFFAOYSA-N n,n'-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]ethanimidamide;trihydrochloride Chemical compound Cl.Cl.Cl.N1=CNC(C)=C1CSCCN=C(C)NCCSCC=1N=CNC=1C CHJKZRRKIUZHLF-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 235000019198 oils Nutrition 0.000 claims 1
- 239000004006 olive oil Substances 0.000 claims 1
- 235000008390 olive oil Nutrition 0.000 claims 1
- 150000002905 orthoesters Chemical class 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000312 peanut oil Substances 0.000 claims 1
- 239000001814 pectin Substances 0.000 claims 1
- 235000010987 pectin Nutrition 0.000 claims 1
- 229920001277 pectin Polymers 0.000 claims 1
- 239000008188 pellet Substances 0.000 claims 1
- 229940075930 picrate Drugs 0.000 claims 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 238000010254 subcutaneous injection Methods 0.000 claims 1
- 239000007929 subcutaneous injection Substances 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 230000008961 swelling Effects 0.000 claims 1
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- 235000012222 talc Nutrition 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 229940100611 topical cream Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 210000004291 uterus Anatomy 0.000 claims 1
- 230000024883 vasodilation Effects 0.000 claims 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
- 102000000543 Histamine Receptors Human genes 0.000 description 1
- 108010002059 Histamine Receptors Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000009141 biological interaction Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10869/74A GB1496787A (en) | 1974-03-12 | 1974-03-12 | Heteroalkylthioalkyl amidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL100317B1 true PL100317B1 (pl) | 1978-09-30 |
Family
ID=9975816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1975178679A PL100317B1 (pl) | 1974-03-12 | 1975-03-11 | Sposob wytwarzania nowych pochodnych amidyny |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US4036971A (en, 2012) |
| JP (1) | JPS5946220B2 (en, 2012) |
| BE (1) | BE825976A (en, 2012) |
| CA (1) | CA1055505A (en, 2012) |
| DE (1) | DE2510860A1 (en, 2012) |
| DK (1) | DK74675A (en, 2012) |
| ES (1) | ES435540A1 (en, 2012) |
| FR (1) | FR2263765B1 (en, 2012) |
| GB (1) | GB1496787A (en, 2012) |
| HU (1) | HU171049B (en, 2012) |
| IE (1) | IE40725B1 (en, 2012) |
| IL (1) | IL46638A0 (en, 2012) |
| LU (1) | LU72013A1 (en, 2012) |
| NL (1) | NL7502935A (en, 2012) |
| NO (2) | NO143381C (en, 2012) |
| PH (1) | PH14072A (en, 2012) |
| PL (1) | PL100317B1 (en, 2012) |
| SE (1) | SE7502715L (en, 2012) |
| ZA (1) | ZA75870B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1496787A (en) * | 1974-03-12 | 1978-01-05 | Smith Kline French Lab | Heteroalkylthioalkyl amidine derivatives |
| NO781300L (no) | 1977-04-20 | 1978-10-23 | Ici Ltd | Fremgangsmaate for fremstilling av fysiologisk aktive guanidinderivater |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| IL57415A (en) * | 1978-05-30 | 1984-08-31 | Smith Kline French Lab | Nitropyrrole compounds,process for preparing them and pharmaceutical compositions containing them |
| US4309435A (en) * | 1978-10-16 | 1982-01-05 | Imperial Chemical Industries Ltd. | Antisecretory guanidine derivatives and pharmaceutical compositions containing them |
| DE3069889D1 (en) | 1979-01-18 | 1985-02-14 | Ici Plc | Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| US4262125A (en) * | 1979-07-23 | 1981-04-14 | American Home Products Corporation | (1H-Imidazol-5-ylmethyl)isothioureas |
| US4382090A (en) * | 1980-10-02 | 1983-05-03 | Eli Lilly And Company | N-Thiazolylmethylthioalkyl-N'alkylamidines and related compounds |
| IE53068B1 (en) * | 1981-06-15 | 1988-05-25 | Merck & Co Inc | Diamino isothiazole-1-oxides and -1,1-dioxides as gastic secretion inhibitors |
| JP3003148B2 (ja) * | 1989-01-05 | 2000-01-24 | 藤沢薬品工業株式会社 | チアゾール化合物、その製造法およびそれを含有する医薬組成物 |
| FR2883257B1 (fr) * | 2005-03-18 | 2007-06-01 | Thales Sa | Dispositif de compensation de jeu mecanique de commande de vol d'helicoptere |
| US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758146A (fr) * | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Derives de l'amidine |
| US3868457A (en) * | 1969-10-29 | 1975-02-25 | Smith Kline French Lab | Method of inhibiting histamine activity with guanidine compounds |
| US3734924A (en) * | 1970-10-14 | 1973-05-22 | Smith Kline French Lab | Carboxamidines |
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| US3979398A (en) * | 1973-02-08 | 1976-09-07 | Smith Kline & French Laboratories Limited | Sulphoxides |
| US4025527A (en) * | 1973-07-13 | 1977-05-24 | Smith Kline & French Laboratories Limited | Certain thiazoles and oxazoles |
| US4109003A (en) * | 1974-03-12 | 1978-08-22 | Smith Kline & French Laboratories Limited | Pharmacologically active compounds |
| GB1496787A (en) * | 1974-03-12 | 1978-01-05 | Smith Kline French Lab | Heteroalkylthioalkyl amidine derivatives |
| GB1497260A (en) * | 1974-06-28 | 1978-01-05 | Smith Kline French Lab | Guanidine derivatives |
| GB1531231A (en) * | 1974-09-02 | 1978-11-08 | Smith Kline French Lab | Process for the production of cyanoguanidine derivatives |
| US4120972A (en) * | 1975-02-03 | 1978-10-17 | Smith Kline & French Laboratories Limited | Imidazolylmethylthio-ethyl isothiourea compounds |
-
1974
- 1974-03-12 GB GB10869/74A patent/GB1496787A/en not_active Expired
-
1975
- 1975-02-11 ZA ZA00750870A patent/ZA75870B/xx unknown
- 1975-02-14 IL IL46638A patent/IL46638A0/xx unknown
- 1975-02-14 CA CA220,151A patent/CA1055505A/en not_active Expired
- 1975-02-19 IE IE340/75A patent/IE40725B1/xx unknown
- 1975-02-19 US US05/551,220 patent/US4036971A/en not_active Expired - Lifetime
- 1975-02-26 BE BE153733A patent/BE825976A/xx not_active IP Right Cessation
- 1975-02-26 DK DK74675*#A patent/DK74675A/da unknown
- 1975-03-04 FR FR7506687A patent/FR2263765B1/fr not_active Expired
- 1975-03-07 PH PH16881A patent/PH14072A/en unknown
- 1975-03-07 JP JP50028592A patent/JPS5946220B2/ja not_active Expired
- 1975-03-10 LU LU72013A patent/LU72013A1/xx unknown
- 1975-03-11 SE SE7502715A patent/SE7502715L/xx unknown
- 1975-03-11 PL PL1975178679A patent/PL100317B1/pl unknown
- 1975-03-11 NO NO750809A patent/NO143381C/no unknown
- 1975-03-12 DE DE19752510860 patent/DE2510860A1/de not_active Ceased
- 1975-03-12 ES ES435540A patent/ES435540A1/es not_active Expired
- 1975-03-12 HU HU75SI00001458A patent/HU171049B/hu unknown
- 1975-03-12 NL NL7502935A patent/NL7502935A/xx not_active Application Discontinuation
-
1979
- 1979-05-14 US US06/039,090 patent/US4282234A/en not_active Expired - Lifetime
- 1979-12-28 NO NO794346A patent/NO794346L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES435540A1 (es) | 1976-12-16 |
| ZA75870B (en) | 1976-01-28 |
| PH14072A (en) | 1981-01-26 |
| FR2263765A1 (en, 2012) | 1975-10-10 |
| CA1055505A (en) | 1979-05-29 |
| IL46638A0 (en) | 1975-04-25 |
| HU171049B (hu) | 1977-10-28 |
| GB1496787A (en) | 1978-01-05 |
| NO794346L (no) | 1975-09-15 |
| FR2263765B1 (en, 2012) | 1978-08-04 |
| AU7831175A (en) | 1976-08-19 |
| LU72013A1 (en, 2012) | 1975-08-20 |
| IE40725B1 (en) | 1979-08-01 |
| IE40725L (en) | 1975-09-12 |
| US4282234A (en) | 1981-08-04 |
| DE2510860A1 (de) | 1975-09-18 |
| BE825976A (fr) | 1975-08-26 |
| NO143381C (no) | 1981-01-28 |
| DK74675A (en, 2012) | 1975-09-13 |
| US4036971A (en) | 1977-07-19 |
| JPS5946220B2 (ja) | 1984-11-10 |
| SE7502715L (en, 2012) | 1975-09-15 |
| JPS50129550A (en, 2012) | 1975-10-13 |
| NO750809L (en, 2012) | 1975-09-15 |
| NL7502935A (nl) | 1975-09-16 |
| NO143381B (no) | 1980-10-20 |
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