CH615669A5 - - Google Patents
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- Publication number
- CH615669A5 CH615669A5 CH838175A CH838175A CH615669A5 CH 615669 A5 CH615669 A5 CH 615669A5 CH 838175 A CH838175 A CH 838175A CH 838175 A CH838175 A CH 838175A CH 615669 A5 CH615669 A5 CH 615669A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- ethyl
- methylthio
- imidazolyl
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 description 64
- -1 alkyl radical Chemical class 0.000 description 33
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 229960001340 histamine Drugs 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 235000015497 potassium bicarbonate Nutrition 0.000 description 10
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 10
- 239000011736 potassium bicarbonate Substances 0.000 description 10
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 5
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000739 antihistaminic agent Substances 0.000 description 4
- 229940125715 antihistaminic agent Drugs 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 2
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012493 hydrazine sulfate Substances 0.000 description 2
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- URZFVRZJQHCTGN-UHFFFAOYSA-N 1,3-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]thiourea Chemical compound N1=CNC(CSCCNC(=S)NCCSCC2=C(N=CN2)C)=C1C URZFVRZJQHCTGN-UHFFFAOYSA-N 0.000 description 1
- VAWDITMGGFJDRR-UHFFFAOYSA-N 1-hydroxy-1,2-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine;trihydrochloride Chemical compound Cl.Cl.Cl.N1=CNC(CSCCNC(=N)N(O)CCSCC2=C(N=CN2)C)=C1C VAWDITMGGFJDRR-UHFFFAOYSA-N 0.000 description 1
- YEMTZJBEASSDRM-UHFFFAOYSA-N 1-hydroxy-2,3-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound N1C=NC(CSCCNC(NO)=NCCSCC2=C(NC=N2)C)=C1C YEMTZJBEASSDRM-UHFFFAOYSA-N 0.000 description 1
- KFXFYHXHOWZWLO-UHFFFAOYSA-N 1-hydroxy-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine;dihydrochloride Chemical compound Cl.Cl.CC=1N=CNC=1CSCCNC(=N)NO KFXFYHXHOWZWLO-UHFFFAOYSA-N 0.000 description 1
- ZDMIOCIQUKUKDQ-UHFFFAOYSA-N 1-hydroxy-2-methyl-3-[2-(1,2-thiazol-3-ylmethylsulfanyl)ethyl]guanidine;dihydrochloride Chemical compound Cl.Cl.CN=C(NO)NCCSCC=1C=CSN=1 ZDMIOCIQUKUKDQ-UHFFFAOYSA-N 0.000 description 1
- PELDWVITRDSEIC-UHFFFAOYSA-N 1-hydroxy-2-methyl-3-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]guanidine Chemical compound CN=C(NO)NCCSCC1=NC=CS1 PELDWVITRDSEIC-UHFFFAOYSA-N 0.000 description 1
- YBUCEZQMZAHHJD-UHFFFAOYSA-N 1-hydroxy-2-methyl-3-[2-[2-(5-methyl-1h-imidazol-4-yl)ethylsulfanyl]ethyl]guanidine;dihydrochloride Chemical compound Cl.Cl.CN=C(NO)NCCSCCC=1N=CNC=1C YBUCEZQMZAHHJD-UHFFFAOYSA-N 0.000 description 1
- MSJINHZSICYZOE-UHFFFAOYSA-N 1-hydroxy-3-[2-[(3-hydroxypyridin-2-yl)methylsulfanyl]ethyl]-2-methylguanidine;dihydrochloride Chemical compound Cl.Cl.CN=C(NO)NCCSCC1=NC=CC=C1O MSJINHZSICYZOE-UHFFFAOYSA-N 0.000 description 1
- BSJKVWRALWFTHL-UHFFFAOYSA-N 1-hydroxy-3-[4-(1h-imidazol-5-yl)butyl]-2-methylguanidine;dihydrochloride Chemical compound Cl.Cl.CN=C(NO)NCCCCC1=CN=CN1 BSJKVWRALWFTHL-UHFFFAOYSA-N 0.000 description 1
- CSJVBBDBRGHVRI-UHFFFAOYSA-N 1-methoxy-2,3-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound N1=CNC(C)=C1CSCCN=C(NOC)NCCSCC=1N=CNC=1C CSJVBBDBRGHVRI-UHFFFAOYSA-N 0.000 description 1
- SVATYHGNPFXHAC-UHFFFAOYSA-N 1-methoxy-2,3-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine;trihydrochloride Chemical compound Cl.Cl.Cl.N1=CNC(C)=C1CSCCN=C(NOC)NCCSCC=1N=CNC=1C SVATYHGNPFXHAC-UHFFFAOYSA-N 0.000 description 1
- VKRPWKLHWHTCCG-UHFFFAOYSA-N 1-methyl-3-[3-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]propyl]thiourea Chemical compound CNC(=S)NCCCSCC=1NC=NC=1C VKRPWKLHWHTCCG-UHFFFAOYSA-N 0.000 description 1
- IBFAQPYEXLHCRS-UHFFFAOYSA-N 1-methyl-3-[4-(1,3-thiazol-2-yl)butyl]thiourea Chemical compound CNC(=S)NCCCCC1=NC=CS1 IBFAQPYEXLHCRS-UHFFFAOYSA-N 0.000 description 1
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 description 1
- MGZMTMADROWGCD-UHFFFAOYSA-N 2-methyl-1-(methylamino)-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine dihydrochloride Chemical compound Cl.Cl.CNNC(=NC)NCCSCC=1N=CNC=1C MGZMTMADROWGCD-UHFFFAOYSA-N 0.000 description 1
- HSRQPXIJPMYOGT-UHFFFAOYSA-N 2-methyl-1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-phenylmethoxyguanidine;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1CONC(=NC)NCCSCC=1N=CNC=1C HSRQPXIJPMYOGT-UHFFFAOYSA-N 0.000 description 1
- XWPFJDZVQSXZQY-UHFFFAOYSA-N 2-methyl-1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-propoxyguanidine;dihydrochloride Chemical compound Cl.Cl.CCCONC(=NC)NCCSCC=1N=CNC=1C XWPFJDZVQSXZQY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- USOHDKWPWJCCMV-UHFFFAOYSA-N Cl.Cl.CCCCN=C(NO)NCCSCC=1N=CNC=1C Chemical compound Cl.Cl.CCCCN=C(NO)NCCSCC=1N=CNC=1C USOHDKWPWJCCMV-UHFFFAOYSA-N 0.000 description 1
- ZTNUUEKNVDAUSE-UHFFFAOYSA-N Cl.Cl.CN=C(NO)NCCCSCC=1N=CNC=1C Chemical compound Cl.Cl.CN=C(NO)NCCCSCC=1N=CNC=1C ZTNUUEKNVDAUSE-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 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
- FPBPLBWLMYGIQR-UHFFFAOYSA-N Metiamide Chemical compound CNC(=S)NCCSCC=1N=CNC=1C FPBPLBWLMYGIQR-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
- 229960003291 chlorphenamine Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 229960000520 diphenhydramine Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IDJMDIVMAOGVJW-UHFFFAOYSA-N guanidine;trihydrochloride Chemical compound Cl.Cl.Cl.NC(N)=N IDJMDIVMAOGVJW-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 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
- HDWGTZXDTKDOGI-UHFFFAOYSA-N methyl n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;dihydrochloride Chemical compound Cl.Cl.CSC(=N)NCCSCC=1NC=NC=1C HDWGTZXDTKDOGI-UHFFFAOYSA-N 0.000 description 1
- JZSMYYMNOIQIHX-UHFFFAOYSA-N methyl n'-methyl-n-[2-(1,2-oxazol-3-ylmethylsulfanyl)ethyl]carbamimidothioate;dihydrochloride Chemical compound Cl.Cl.CNC(SC)=NCCSCC=1C=CON=1 JZSMYYMNOIQIHX-UHFFFAOYSA-N 0.000 description 1
- KGTGBQBFBSPAAO-UHFFFAOYSA-N methyl n'-methyl-n-[3-(1,3-oxazol-2-ylsulfanyl)propyl]carbamimidothioate;dihydrochloride Chemical compound Cl.Cl.CNC(SC)=NCCCSC1=NC=CO1 KGTGBQBFBSPAAO-UHFFFAOYSA-N 0.000 description 1
- WRBSCMVFAPTVHW-UHFFFAOYSA-N methyl n-[2-[(3-bromopyridin-2-yl)methylsulfanyl]ethyl]-n'-methylcarbamimidothioate;dihydrochloride Chemical compound Cl.Cl.CNC(SC)=NCCSCC1=NC=CC=C1Br WRBSCMVFAPTVHW-UHFFFAOYSA-N 0.000 description 1
- KXQKVKMMHRGSRH-UHFFFAOYSA-N methyl n-[2-[(3-hydroxypyridin-2-yl)methylsulfanyl]ethyl]-n'-methylcarbamimidothioate;dihydrochloride Chemical compound Cl.Cl.CNC(SC)=NCCSCC1=NC=CC=C1O KXQKVKMMHRGSRH-UHFFFAOYSA-N 0.000 description 1
- HTWXYYKEGRHEHQ-UHFFFAOYSA-N methyl n-[4-(1h-imidazol-5-yl)butyl]-n'-methylcarbamimidothioate Chemical compound CNC(SC)=NCCCCC1=CNC=N1 HTWXYYKEGRHEHQ-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
- WCVVIGQKJZLJDB-UHFFFAOYSA-N o-butylhydroxylamine Chemical compound CCCCON WCVVIGQKJZLJDB-UHFFFAOYSA-N 0.000 description 1
- UOKZUTXLHRTLFH-UHFFFAOYSA-N o-phenylhydroxylamine Chemical compound NOC1=CC=CC=C1 UOKZUTXLHRTLFH-UHFFFAOYSA-N 0.000 description 1
- PRAARDGLAWZXML-UHFFFAOYSA-N o-propylhydroxylamine Chemical compound CCCON PRAARDGLAWZXML-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- BNKMLRRKLVSLJN-UHFFFAOYSA-N tert-butyl n-amino-n-methylcarbamate;sulfuric acid Chemical compound OS(O)(=O)=O.CN(N)C(=O)OC(C)(C)C BNKMLRRKLVSLJN-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
- 150000003852 triazoles Chemical class 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—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
- C07D277/22—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
- C07D277/22—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
- C07D277/28—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical 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)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB28722/74A GB1497260A (en) | 1974-06-28 | 1974-06-28 | Guanidine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
CH615669A5 true CH615669A5 (fr) | 1980-02-15 |
Family
ID=10280055
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH838175A CH615669A5 (fr) | 1974-06-28 | 1975-06-27 |
Country Status (20)
Country | Link |
---|---|
US (1) | US4034101A (fr) |
JP (1) | JPS5946221B2 (fr) |
AU (1) | AU503858B2 (fr) |
BE (1) | BE830272A (fr) |
CA (1) | CA1076579A (fr) |
CH (1) | CH615669A5 (fr) |
DE (1) | DE2528639A1 (fr) |
DK (1) | DK268975A (fr) |
ES (1) | ES438944A1 (fr) |
FR (1) | FR2276042A1 (fr) |
GB (1) | GB1497260A (fr) |
IE (1) | IE41625B1 (fr) |
IL (1) | IL47394A (fr) |
LU (1) | LU72835A1 (fr) |
NL (1) | NL7506951A (fr) |
NO (1) | NO143942C (fr) |
PH (1) | PH14275A (fr) |
PL (1) | PL98616B1 (fr) |
SE (1) | SE417961B (fr) |
ZA (1) | ZA753455B (fr) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5014808U (fr) * | 1973-06-06 | 1975-02-17 | ||
JPS55822B2 (fr) * | 1973-07-09 | 1980-01-10 | ||
US4137319A (en) * | 1974-02-07 | 1979-01-30 | Smith Kline & French Laboratories Limited | Guanidino, thioureido, isothioureido and nitrovinylamino derivatives of pyridine |
US4197305A (en) * | 1974-02-07 | 1980-04-08 | Smith Kline & French Laboratories Limited | Thiazole, isothiazole, oxazole and isoxazole compounds |
GB1493931A (en) * | 1974-02-07 | 1977-11-30 | Smith Kline French Lab | Guanidines isothioureas and thioureas |
US4170652A (en) * | 1974-03-12 | 1979-10-09 | Smith Kline & French Laboratories Limited | Heterocyclic-methylthioalkyl-guanidines |
GB1496787A (en) * | 1974-03-12 | 1978-01-05 | Smith Kline French Lab | Heteroalkylthioalkyl amidine derivatives |
JPS5912767Y2 (ja) * | 1974-03-28 | 1984-04-17 | アイワ カブシキガイシヤ | 回転機器の作動切換装置 |
US4093729A (en) * | 1974-06-28 | 1978-06-06 | Smith Kline & French Laboratories Limited | N-Oxy and N-amino guanidines |
IL49528A (en) * | 1975-05-21 | 1980-11-30 | Smith Kline French Lab | Imidazolyl(or thiazolyl)methylthio(or butyl)guanidine or thiourea derivatives,their preparation and pharmaceutical compositions comprising them |
US4192879A (en) * | 1975-05-21 | 1980-03-11 | Smith Kline & French Laboratories Limited | Imidazolyl alkylamino nitroethylene compounds |
GB1564502A (en) * | 1975-07-31 | 1980-04-10 | Smith Kline French Lab | Guanidines thioureas and 1,1-diamino-2-nitroethylene derivatives |
GR62452B (en) | 1977-04-20 | 1979-04-12 | Ici Ltd | Preparation process of guanidine derivatives |
US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
GB1602458A (en) * | 1977-05-05 | 1981-11-11 | Smith Kline French Lab | Bisamidines as histamine h2-antagonists |
US4108859A (en) * | 1977-06-06 | 1978-08-22 | The Dow Chemical Company | Microbicidal (pyridinylamino) alkyl guanidines |
US4233302A (en) | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
DE2963363D1 (en) | 1978-05-24 | 1982-09-09 | Ici Plc | Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them |
CA1140925A (fr) * | 1978-10-16 | 1983-02-08 | Derrick F. Jones | Derives heterocycliques anti-secretion, a chaine ramifiee, procedes pour les fabriquer et compositions pharmaceutiques qui en contiennent |
JPS56124143A (en) * | 1980-02-29 | 1981-09-29 | Sanyo Electric Co Ltd | Control mechanism of tape recorder |
AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
JPS6156012U (fr) * | 1984-09-19 | 1986-04-15 | ||
JPS61228914A (ja) * | 1985-04-04 | 1986-10-13 | Sumitomo Heavy Ind Ltd | 成形用金型 |
JPH0347862Y2 (fr) * | 1985-12-14 | 1991-10-14 | ||
EP4196793A1 (fr) | 2020-08-11 | 2023-06-21 | Université de Strasbourg | Bloqueurs de h2 ciblant des macrophages du foie pour la prévention et le traitement d'une maladie du foie et du cancer |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE758146A (fr) * | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Derives de l'amidine |
GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
-
1974
- 1974-06-28 GB GB28722/74A patent/GB1497260A/en not_active Expired
-
1975
- 1975-05-28 ZA ZA00753455A patent/ZA753455B/xx unknown
- 1975-05-30 IL IL47394A patent/IL47394A/xx unknown
- 1975-06-09 IE IE1299/75A patent/IE41625B1/en unknown
- 1975-06-11 NL NL7506951A patent/NL7506951A/xx not_active Application Discontinuation
- 1975-06-11 US US05/585,898 patent/US4034101A/en not_active Expired - Lifetime
- 1975-06-12 CA CA229,222A patent/CA1076579A/fr not_active Expired
- 1975-06-13 DK DK268975A patent/DK268975A/da not_active Application Discontinuation
- 1975-06-16 BE BE157354A patent/BE830272A/fr not_active IP Right Cessation
- 1975-06-20 PH PH17301A patent/PH14275A/en unknown
- 1975-06-20 AU AU82304/75A patent/AU503858B2/en not_active Ceased
- 1975-06-24 FR FR7519669A patent/FR2276042A1/fr active Granted
- 1975-06-24 JP JP50079233A patent/JPS5946221B2/ja not_active Expired
- 1975-06-26 DE DE19752528639 patent/DE2528639A1/de not_active Withdrawn
- 1975-06-26 SE SE7507364A patent/SE417961B/xx unknown
- 1975-06-26 LU LU72835A patent/LU72835A1/xx unknown
- 1975-06-27 PL PL1975181592A patent/PL98616B1/pl unknown
- 1975-06-27 NO NO752330A patent/NO143942C/no unknown
- 1975-06-27 CH CH838175A patent/CH615669A5/de not_active IP Right Cessation
- 1975-06-27 ES ES438944A patent/ES438944A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
IE41625L (en) | 1975-12-28 |
CA1076579A (fr) | 1980-04-29 |
NO143942B (no) | 1981-02-02 |
IE41625B1 (en) | 1980-02-13 |
JPS5946221B2 (ja) | 1984-11-10 |
US4034101A (en) | 1977-07-05 |
DK268975A (da) | 1975-12-29 |
NO143942C (no) | 1981-05-13 |
SE7507364L (sv) | 1975-12-29 |
AU8230475A (en) | 1976-12-23 |
IL47394A (en) | 1980-01-31 |
NO752330L (fr) | 1975-12-30 |
SE417961B (sv) | 1981-04-27 |
PL98616B1 (pl) | 1978-05-31 |
ZA753455B (en) | 1976-04-28 |
FR2276042B1 (fr) | 1980-04-25 |
LU72835A1 (fr) | 1975-10-08 |
IL47394A0 (en) | 1975-07-28 |
NL7506951A (nl) | 1975-12-30 |
JPS5119766A (fr) | 1976-02-17 |
BE830272A (fr) | 1975-12-16 |
GB1497260A (en) | 1978-01-05 |
PH14275A (en) | 1981-04-29 |
DE2528639A1 (de) | 1976-01-15 |
FR2276042A1 (fr) | 1976-01-23 |
AU503858B2 (en) | 1979-09-27 |
ES438944A1 (es) | 1977-02-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased | ||
PL | Patent ceased |