CH615916A5 - - Google Patents
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- Publication number
- CH615916A5 CH615916A5 CH142375A CH142375A CH615916A5 CH 615916 A5 CH615916 A5 CH 615916A5 CH 142375 A CH142375 A CH 142375A CH 142375 A CH142375 A CH 142375A CH 615916 A5 CH615916 A5 CH 615916A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- ethyl
- bis
- propane
- formula
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- 150000003854 isothiazoles Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- -1 alkyl radical Chemical class 0.000 description 32
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000001294 propane Substances 0.000 description 29
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
- 239000000243 solution Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229960001340 histamine Drugs 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 5
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- WAIHMWWSWLOHNH-UHFFFAOYSA-N 2-(1,3-thiazol-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NC=CS1 WAIHMWWSWLOHNH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 4
- 239000000739 antihistaminic agent Substances 0.000 description 4
- 229940125715 antihistaminic agent Drugs 0.000 description 4
- RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 4
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 4
- 229960000582 mepyramine Drugs 0.000 description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 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 description 3
- CNMUGSJVSYLQOX-UHFFFAOYSA-N 2-(1h-imidazol-5-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=CNC=N1 CNMUGSJVSYLQOX-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
- 230000027119 gastric acid secretion Effects 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- AOGPUGLWMPUQQZ-UHFFFAOYSA-N n-(3-aminopropyl)benzamide Chemical compound NCCCNC(=O)C1=CC=CC=C1 AOGPUGLWMPUQQZ-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 2
- GBXRYFFHDKZKTC-UHFFFAOYSA-N 1-(1,3-oxazol-2-ylsulfanyl)propan-2-amine Chemical compound CC(N)CSC1=NC=CO1 GBXRYFFHDKZKTC-UHFFFAOYSA-N 0.000 description 2
- DGSMYXNLEIKEOF-UHFFFAOYSA-N 1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-[3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylcarbamothioylamino]propyl]thiourea Chemical compound N1C=NC(CSCCNC(=S)NCCCNC(=S)NCCSCC2=C(NC=N2)C)=C1C DGSMYXNLEIKEOF-UHFFFAOYSA-N 0.000 description 2
- GKIUPDRWOXMZDT-UHFFFAOYSA-N 2-(1,2-thiazol-3-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC=1C=CSN=1 GKIUPDRWOXMZDT-UHFFFAOYSA-N 0.000 description 2
- BUTQLNVJGRJSAE-UHFFFAOYSA-N 2-(1h-1,2,4-triazol-5-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC=1N=CNN=1 BUTQLNVJGRJSAE-UHFFFAOYSA-N 0.000 description 2
- ILVDHDDYTQIIQH-UHFFFAOYSA-N 2-(1h-pyrazol-5-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC=1C=CNN=1 ILVDHDDYTQIIQH-UHFFFAOYSA-N 0.000 description 2
- YTFSLUOQGOXGNB-UHFFFAOYSA-N 2-(2-aminoethylsulfanylmethyl)pyridin-3-ol Chemical compound NCCSCC1=NC=CC=C1O YTFSLUOQGOXGNB-UHFFFAOYSA-N 0.000 description 2
- KPSVNTMKXZMIHQ-UHFFFAOYSA-N 2-(pyrazin-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=CN=CC=N1 KPSVNTMKXZMIHQ-UHFFFAOYSA-N 0.000 description 2
- PFUQKTUXZZYSFJ-UHFFFAOYSA-N 2-(pyridazin-3-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=CC=CN=N1 PFUQKTUXZZYSFJ-UHFFFAOYSA-N 0.000 description 2
- HTABEAIBEITBJS-UHFFFAOYSA-N 2-[(3-chloropyridin-2-yl)methylsulfanyl]ethanamine Chemical compound NCCSCC1=NC=CC=C1Cl HTABEAIBEITBJS-UHFFFAOYSA-N 0.000 description 2
- FBHDEPMFGINFBF-UHFFFAOYSA-N 2-[(3-methylpyridin-2-yl)methylsulfanyl]ethanamine Chemical compound CC1=CC=CN=C1CSCCN FBHDEPMFGINFBF-UHFFFAOYSA-N 0.000 description 2
- NTLFEXLXZRBDPP-UHFFFAOYSA-N 2-[(4-bromo-1h-imidazol-5-yl)methylsulfanyl]ethanamine Chemical compound NCCSCC=1NC=NC=1Br NTLFEXLXZRBDPP-UHFFFAOYSA-N 0.000 description 2
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 description 2
- IKQVJFAUVUPZFL-UHFFFAOYSA-N 2-[3-[[amino-[2-(1h-pyrazol-5-ylmethylsulfanyl)ethylamino]methylidene]amino]propyl]-1-[2-(1h-pyrazol-5-ylmethylsulfanyl)ethyl]guanidine Chemical compound C1=CNN=C1CSCCN=C(N)NCCCNC(N)=NCCSCC=1C=CNN=1 IKQVJFAUVUPZFL-UHFFFAOYSA-N 0.000 description 2
- PKYTURKWLOHLCW-UHFFFAOYSA-N 4-(1,3-thiazol-4-yl)butan-1-amine Chemical compound NCCCCC1=CSC=N1 PKYTURKWLOHLCW-UHFFFAOYSA-N 0.000 description 2
- VJSUMPPMFYQOMP-UHFFFAOYSA-N 4-(1h-imidazol-5-yl)butan-1-amine Chemical compound NCCCCC1=CNC=N1 VJSUMPPMFYQOMP-UHFFFAOYSA-N 0.000 description 2
- XLULFLSTBMZSTE-UHFFFAOYSA-N 4-(4-bromo-1h-imidazol-5-yl)butan-1-amine Chemical compound NCCCCC=1N=CNC=1Br XLULFLSTBMZSTE-UHFFFAOYSA-N 0.000 description 2
- XFZLAEXVWQCHMU-UHFFFAOYSA-N 4-(5-methyl-1h-imidazol-4-yl)butan-1-amine Chemical compound CC=1NC=NC=1CCCCN XFZLAEXVWQCHMU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 102000003834 Histamine H1 Receptors Human genes 0.000 description 2
- 108090000110 Histamine H1 Receptors Proteins 0.000 description 2
- 102000000543 Histamine Receptors Human genes 0.000 description 2
- 108010002059 Histamine Receptors Proteins 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- NCLWOOPAIRRZNV-UHFFFAOYSA-N 1-(3-aminopropyl)-3-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]thiourea Chemical compound NCCCNC(=S)NCCSCC1=NC=CS1 NCLWOOPAIRRZNV-UHFFFAOYSA-N 0.000 description 1
- CYKWSZOGBPOLPI-UHFFFAOYSA-N 1-[2-(1,2-thiazol-3-ylmethylsulfanyl)ethyl]-3-[3-[2-(1,2-thiazol-3-ylmethylsulfanyl)ethylcarbamothioylamino]propyl]thiourea Chemical compound C1=CSN=C1CSCCNC(=S)NCCCNC(=S)NCCSCC=1C=CSN=1 CYKWSZOGBPOLPI-UHFFFAOYSA-N 0.000 description 1
- KGPKLCYPEIOLMM-UHFFFAOYSA-N 1-[2-(1,3-oxazol-2-ylsulfanyl)propyl]-3-[3-[2-(1,3-oxazol-2-ylsulfanyl)propylcarbamothioylamino]propyl]thiourea Chemical compound N=1C=COC=1SC(C)CNC(=S)NCCCNC(=S)NCC(C)SC1=NC=CO1 KGPKLCYPEIOLMM-UHFFFAOYSA-N 0.000 description 1
- ICIGOMUTTLBISI-UHFFFAOYSA-N 1-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]-3-[3-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethylcarbamothioylamino]propyl]thiourea Chemical compound N=1C=CSC=1CSCCNC(=S)NCCCNC(=S)NCCSCC1=NC=CS1 ICIGOMUTTLBISI-UHFFFAOYSA-N 0.000 description 1
- GNUBHFHZVDWRON-UHFFFAOYSA-N 1-[2-(1h-imidazol-2-ylmethylsulfanyl)ethyl]-3-[3-[2-(1h-imidazol-2-ylmethylsulfanyl)ethylcarbamothioylamino]propyl]thiourea Chemical compound N=1C=CNC=1CSCCNC(=S)NCCCNC(=S)NCCSCC1=NC=CN1 GNUBHFHZVDWRON-UHFFFAOYSA-N 0.000 description 1
- JHRIZQZDRCENCF-UHFFFAOYSA-N 1-[2-[(1-methylimidazol-2-yl)methylsulfanyl]ethyl]-3-[3-[2-[(1-methylimidazol-2-yl)methylsulfanyl]ethylcarbamothioylamino]propyl]thiourea Chemical compound CN1C=CN=C1CSCCNC(=S)NCCCNC(=S)NCCSCC1=NC=CN1C JHRIZQZDRCENCF-UHFFFAOYSA-N 0.000 description 1
- TZJYBTLNAUWEBV-UHFFFAOYSA-N 1-[2-[(4-bromo-1h-imidazol-5-yl)methylsulfanyl]ethyl]-3-[3-[2-[(4-bromo-1h-imidazol-5-yl)methylsulfanyl]ethylcarbamothioylamino]propyl]thiourea Chemical compound N1C=NC(CSCCNC(=S)NCCCNC(=S)NCCSCC2=C(NC=N2)Br)=C1Br TZJYBTLNAUWEBV-UHFFFAOYSA-N 0.000 description 1
- WQPBPNODDHLWMF-UHFFFAOYSA-N 1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-[4-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylcarbamothioylamino]butyl]thiourea Chemical compound N1C=NC(CSCCNC(=S)NCCCCNC(=S)NCCSCC2=C(NC=N2)C)=C1C WQPBPNODDHLWMF-UHFFFAOYSA-N 0.000 description 1
- QIKDVTOFOCQUDE-UHFFFAOYSA-N 1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-[6-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylcarbamothioylamino]hexyl]thiourea Chemical compound N1C=NC(CSCCNC(=S)NCCCCCCNC(=S)NCCSCC2=C(NC=N2)C)=C1C QIKDVTOFOCQUDE-UHFFFAOYSA-N 0.000 description 1
- GXKPBDYJGLZWIZ-UHFFFAOYSA-N 1-[3-[carbamimidoyl(3-pyrimidin-2-ylsulfanylpropyl)amino]propyl]-1-(3-pyrimidin-2-ylsulfanylpropyl)guanidine Chemical compound N=1C=CC=NC=1SCCCN(C(N)=N)CCCN(C(=N)N)CCCSC1=NC=CC=N1 GXKPBDYJGLZWIZ-UHFFFAOYSA-N 0.000 description 1
- KAONJUFJIFWWRD-UHFFFAOYSA-N 1-[3-[carbamothioyl-[2-(1h-pyrazol-5-ylmethylsulfanyl)ethyl]amino]propyl]-1-[2-(1h-pyrazol-5-ylmethylsulfanyl)ethyl]thiourea Chemical compound C=1C=NNC=1CSCCN(C(=S)N)CCCN(C(N)=S)CCSCC1=CC=NN1 KAONJUFJIFWWRD-UHFFFAOYSA-N 0.000 description 1
- NUOLZIOBZZLSOX-UHFFFAOYSA-N 1-[3-[carbamothioyl-[2-(pyrimidin-2-ylmethylsulfanyl)ethyl]amino]propyl]-1-[2-(pyrimidin-2-ylmethylsulfanyl)ethyl]thiourea Chemical compound N=1C=CC=NC=1CSCCN(C(=S)N)CCCN(C(N)=S)CCSCC1=NC=CC=N1 NUOLZIOBZZLSOX-UHFFFAOYSA-N 0.000 description 1
- FCOVLPPCZPSLTO-UHFFFAOYSA-N 1-benzylsulfonyl-2-[3-[[(benzylsulfonylamino)-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]methylidene]amino]propyl]-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound C(C1=CC=CC=C1)S(=O)(=O)N=C(NCCCNC(=NS(=O)(=O)CC1=CC=CC=C1)NCCSCC=1N=CNC=1C)NCCSCC=1N=CNC=1C FCOVLPPCZPSLTO-UHFFFAOYSA-N 0.000 description 1
- ZBHYOVVCRWKPHZ-UHFFFAOYSA-N 2-(1,2-oxazol-3-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC=1C=CON=1 ZBHYOVVCRWKPHZ-UHFFFAOYSA-N 0.000 description 1
- CJIFBUZRANSSAI-UHFFFAOYSA-N 2-(1h-imidazol-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NC=CN1 CJIFBUZRANSSAI-UHFFFAOYSA-N 0.000 description 1
- HRHRZGWCLHHHDK-UHFFFAOYSA-N 2-(1h-imidazol-5-ylmethylsulfanyl)ethylthiourea Chemical compound NC(=S)NCCSCC1=CNC=N1 HRHRZGWCLHHHDK-UHFFFAOYSA-N 0.000 description 1
- CQPMAHTXYGMFGG-UHFFFAOYSA-N 2-(pyrimidin-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NC=CC=N1 CQPMAHTXYGMFGG-UHFFFAOYSA-N 0.000 description 1
- DJFNUVQFNPDLFL-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylcarbamodithioic acid Chemical compound CC=1N=CNC=1CSCCNC(S)=S DJFNUVQFNPDLFL-UHFFFAOYSA-N 0.000 description 1
- XSAXLPYZTXJUDU-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylthiourea Chemical compound CC=1N=CNC=1CSCCNC(N)=S XSAXLPYZTXJUDU-UHFFFAOYSA-N 0.000 description 1
- ZDNGFYSUDXCCJS-UHFFFAOYSA-N 2-[2-(1,3-oxazol-2-ylsulfanyl)propyl]-1-[3-[[n'-[2-(1,3-oxazol-2-ylsulfanyl)propyl]carbamimidoyl]amino]propyl]guanidine Chemical compound N=1C=COC=1SC(C)CN=C(N)NCCCNC(N)=NCC(C)SC1=NC=CO1 ZDNGFYSUDXCCJS-UHFFFAOYSA-N 0.000 description 1
- OWRWBHQUTYXNSI-UHFFFAOYSA-N 2-[3-[[amino-[2-(1,2-oxazol-3-ylmethylsulfanyl)ethylamino]methylidene]amino]propyl]-1-[2-(1,2-oxazol-3-ylmethylsulfanyl)ethyl]guanidine Chemical compound C1=CON=C1CSCCN=C(N)NCCCNC(N)=NCCSCC=1C=CON=1 OWRWBHQUTYXNSI-UHFFFAOYSA-N 0.000 description 1
- RVLONASXDOJXRE-UHFFFAOYSA-N 2-[3-[[amino-[2-(1h-imidazol-2-ylmethylsulfanyl)ethylamino]methylidene]amino]propyl]-1-[2-(1h-imidazol-2-ylmethylsulfanyl)ethyl]guanidine Chemical compound N=1C=CNC=1CSCCN=C(N)NCCCNC(N)=NCCSCC1=NC=CN1 RVLONASXDOJXRE-UHFFFAOYSA-N 0.000 description 1
- STXPZKMKZMPPOF-UHFFFAOYSA-N 2-[3-[[amino-[2-(1h-imidazol-5-ylmethylsulfanyl)ethylamino]methylidene]amino]propyl]-1-[2-(1h-imidazol-5-ylmethylsulfanyl)ethyl]guanidine Chemical compound C=1NC=NC=1CSCCN=C(N)NCCCNC(N)=NCCSCC1=CNC=N1 STXPZKMKZMPPOF-UHFFFAOYSA-N 0.000 description 1
- ARXZMRYJCIBWJY-UHFFFAOYSA-N 2-[3-[[amino-[2-[(1-methylimidazol-2-yl)methylsulfanyl]ethylamino]methylidene]amino]propyl]-1-[2-[(1-methylimidazol-2-yl)methylsulfanyl]ethyl]guanidine Chemical compound CN1C=CN=C1CSCCN=C(N)NCCCNC(N)=NCCSCC1=NC=CN1C ARXZMRYJCIBWJY-UHFFFAOYSA-N 0.000 description 1
- ZXFRKTRBZWFWTE-UHFFFAOYSA-N 2-[3-[[amino-[2-[(3-hydroxypyridin-2-yl)methylsulfanyl]ethylamino]methylidene]amino]propyl]-1-[2-[(3-hydroxypyridin-2-yl)methylsulfanyl]ethyl]guanidine Chemical compound N=1C=CC=C(O)C=1CSCCN=C(N)NCCCNC(N)=NCCSCC1=NC=CC=C1O ZXFRKTRBZWFWTE-UHFFFAOYSA-N 0.000 description 1
- FOWSBWKJJLDGCK-UHFFFAOYSA-N 2-[3-[[amino-[2-[(4-bromo-1h-imidazol-5-yl)methylsulfanyl]ethylamino]methylidene]amino]propyl]-1-[2-[(4-bromo-1h-imidazol-5-yl)methylsulfanyl]ethyl]guanidine Chemical compound N1=CNC(Br)=C1CSCCN=C(N)NCCCNC(N)=NCCSCC=1N=CNC=1Br FOWSBWKJJLDGCK-UHFFFAOYSA-N 0.000 description 1
- QIPBYNQBPYZSMQ-UHFFFAOYSA-N 2-[3-[[amino-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]methylidene]amino]propyl]-1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound N1C=NC(CSCCN=C(N)NCCCNC(N)=NCCSCC2=C(NC=N2)C)=C1C QIPBYNQBPYZSMQ-UHFFFAOYSA-N 0.000 description 1
- VHKHJQHAIAWOBU-UHFFFAOYSA-N 2-[3-[[benzenesulfonamido-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]methylidene]amino]propyl]-1-(benzenesulfonyl)-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound N1C=NC(CSCCNC(NS(=O)(=O)C=2C=CC=CC=2)=NCCCN=C(NCCSCC2=C(NC=N2)C)NS(=O)(=O)C=2C=CC=CC=2)=C1C VHKHJQHAIAWOBU-UHFFFAOYSA-N 0.000 description 1
- GVODQJZLWQAELN-UHFFFAOYSA-N 2-[6-[[amino-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]methylidene]amino]hexyl]-1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound N1C=NC(CSCCN=C(N)NCCCCCCNC(N)=NCCSCC2=C(NC=N2)C)=C1C GVODQJZLWQAELN-UHFFFAOYSA-N 0.000 description 1
- GNFBOGPCQHTJQI-UHFFFAOYSA-N 3-pyrimidin-2-ylsulfanylpropan-1-amine Chemical compound NCCCSC1=NC=CC=N1 GNFBOGPCQHTJQI-UHFFFAOYSA-N 0.000 description 1
- UGYXPZQILZRKJJ-UHFFFAOYSA-N 4-methylhistamine Chemical compound CC=1NC=NC=1CCN UGYXPZQILZRKJJ-UHFFFAOYSA-N 0.000 description 1
- LOTSAZPLRIDFID-UHFFFAOYSA-N 5-(2-aminoethylsulfanylmethyl)-1,3,4-thiadiazol-2-amine Chemical compound NCCSCC1=NN=C(N)S1 LOTSAZPLRIDFID-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FGTAYGFIMARZKU-UHFFFAOYSA-N I.I.I.I.N1=CNC(C)=C1CSCCN=C(SC)NCCCNC(SC)=NCCSCC=1N=CNC=1C Chemical compound I.I.I.I.N1=CNC(C)=C1CSCCN=C(SC)NCCCNC(SC)=NCCSCC=1N=CNC=1C FGTAYGFIMARZKU-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 101150034459 Parpbp gene Proteins 0.000 description 1
- 108010079943 Pentagastrin Proteins 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- NPPYCTSQYCMZIB-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CSC(N)=[NH+]CCSCC=1N=CNC=1C.CSC(N)=[NH+]CCSCC=1N=CNC=1C NPPYCTSQYCMZIB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- XMYLSWOTJKUSHE-UHFFFAOYSA-N cyanamide;lead Chemical compound [Pb].NC#N XMYLSWOTJKUSHE-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- OPGQGYQPVOWUOO-UHFFFAOYSA-N methyl n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NCCSCC=1N=CNC=1C OPGQGYQPVOWUOO-UHFFFAOYSA-N 0.000 description 1
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 1
- FHYQJJMAMDZWDF-UHFFFAOYSA-N o-methyl (s-methyl-n-methylsulfonylsulfinimidoyl)methanethioate Chemical compound COC(=S)S(C)=NS(C)(=O)=O FHYQJJMAMDZWDF-UHFFFAOYSA-N 0.000 description 1
- OHWCIOCNYQTGIP-UHFFFAOYSA-N o-methyl [s-methyl-n-(4-methylphenyl)sulfonylsulfinimidoyl]methanethioate Chemical compound COC(=S)S(C)=NS(=O)(=O)C1=CC=C(C)C=C1 OHWCIOCNYQTGIP-UHFFFAOYSA-N 0.000 description 1
- XJYPRBCCYOMVLN-UHFFFAOYSA-N o-methyl [s-methyl-n-(trifluoromethylsulfonyl)sulfinimidoyl]methanethioate Chemical compound COC(=S)S(C)=NS(=O)(=O)C(F)(F)F XJYPRBCCYOMVLN-UHFFFAOYSA-N 0.000 description 1
- 230000001151 other effect Effects 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
- 229940075930 picrate Drugs 0.000 description 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 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- ZVUUCUFDAHKLKT-UHFFFAOYSA-M sodium;2,4,6-trinitrophenolate Chemical compound [Na+].[O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O ZVUUCUFDAHKLKT-UHFFFAOYSA-M 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000004291 uterus Anatomy 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5596/74A GB1493931A (en) | 1974-02-07 | 1974-02-07 | Guanidines isothioureas and thioureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615916A5 true CH615916A5 (en, 2012) | 1980-02-29 |
Family
ID=9799081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH142375A CH615916A5 (en, 2012) | 1974-02-07 | 1975-02-06 |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US3968227A (en, 2012) |
| JP (1) | JPS5946219B2 (en, 2012) |
| AU (1) | AU500729B2 (en, 2012) |
| BE (1) | BE824923A (en, 2012) |
| CA (1) | CA1062263A (en, 2012) |
| CH (1) | CH615916A5 (en, 2012) |
| DE (1) | DE2504794A1 (en, 2012) |
| DK (1) | DK14475A (en, 2012) |
| ES (2) | ES434542A1 (en, 2012) |
| FR (1) | FR2260343B1 (en, 2012) |
| GB (1) | GB1493931A (en, 2012) |
| HU (1) | HU174066B (en, 2012) |
| IE (1) | IE40659B1 (en, 2012) |
| IL (1) | IL46451A (en, 2012) |
| LU (1) | LU71804A1 (en, 2012) |
| NL (1) | NL7500977A (en, 2012) |
| NO (1) | NO143315C (en, 2012) |
| PL (1) | PL98615B1 (en, 2012) |
| SE (1) | SE416050B (en, 2012) |
| ZA (1) | ZA75180B (en, 2012) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| US4105770A (en) * | 1975-07-31 | 1978-08-08 | Smith Kline & French Laboratories Limited | Heterocyclomethylsulphinylethyl derivatives of N-cyanoguanidines, thioureas and 2-amino-1-nitroethylene |
| ZA774220B (en) * | 1976-07-28 | 1978-06-28 | Smith Kline French Lab | Pharmacologically active compounds |
| ZA774221B (en) * | 1976-07-28 | 1978-06-28 | Smith Kline French Lab | Pharmacologically active compounds |
| US4210652A (en) * | 1976-07-28 | 1980-07-01 | Smith Kline & French Laboratories Limited | Pharmacologically active 1,3-bis[1-(2-heteroalkylthio)ethylamino)-2-nitrovinyl-1-amino]propane derivatives |
| US4219553A (en) * | 1976-07-28 | 1980-08-26 | Smith Kline & French Laboratories Limited | Alkoxy pyridyl substituted alkanes |
| 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 |
| US4200760A (en) * | 1978-09-26 | 1980-04-29 | Bristol-Myers Company | Imidazolylalkylthioalkylamino-ethylene derivatives |
| US4309435A (en) | 1978-10-16 | 1982-01-05 | Imperial Chemical Industries Ltd. | Antisecretory guanidine derivatives and pharmaceutical compositions containing them |
| FR2446829A1 (fr) | 1978-11-16 | 1980-08-14 | Glaxo Group Ltd | Derives de polymethylene disubstitues en alpha, omega, procede pour leur preparation et compositions pharmaceutiques les contenant |
| DE3069889D1 (en) | 1979-01-18 | 1985-02-14 | Ici Plc | Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| JPS57102852A (en) * | 1980-12-19 | 1982-06-26 | Shionogi & Co Ltd | Dicarboxylic acid diamide |
| CA2927544A1 (en) | 2015-04-24 | 2016-10-24 | Wal-Mart Stores, Inc. | Method and apparatus for holding containers open |
| 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 (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB850483A (en) * | 1957-10-25 | 1960-10-05 | May & Baker Ltd | Improvements in or relating to pyrimidine derivatives |
| US3622596A (en) * | 1960-10-14 | 1971-11-23 | A Wander Sa Dr | Carbanilide compounds |
| DE1214239B (de) * | 1960-11-01 | 1966-04-14 | Spofa Sdruzeni Podnikuu Pro Zd | Verfahren zur Herstellung von 5-bis-(beta-Chloraethyl)-aminomethyluracil-hydrochlorid |
| CH405282A (de) * | 1961-11-24 | 1966-01-15 | Wander Ag Dr A | Verfahren zur Herstellung basischer Verbindungen |
| US3225047A (en) * | 1964-02-24 | 1965-12-21 | Bristol Myers Co | N,n'-bis(pyrimidine-5-acetyl)ethylene diamines |
| CH440252A (de) * | 1964-04-24 | 1967-07-31 | Wander Ag Dr A | Verfahren zur Herstellung neuer Harnstoffderivate |
| US3335142A (en) * | 1965-07-07 | 1967-08-08 | American Cyanamid Co | Process for the preparation of n, n'-disubstituted ureas |
| US3646049A (en) * | 1970-03-05 | 1972-02-29 | Merck & Co Inc | Acylaminobenzimidazole derivatives |
| US4137234A (en) * | 1971-03-09 | 1979-01-30 | Smith Kline & French Laboratories Limited | Thiazole, isothiazole, oxazole and isoxazole substituted thiourea and urea compounds |
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| US3917626A (en) * | 1971-03-29 | 1975-11-04 | Ici Ltd | 3,6-Dioxa-1,8-octandiamido bis (pyridinium) compounds |
| GB1339764A (en) * | 1971-03-29 | 1973-12-05 | Ici Ltd | Pyridine derivatives |
| GB1493931A (en) * | 1974-02-07 | 1977-11-30 | Smith Kline French Lab | Guanidines isothioureas and thioureas |
| US4062967A (en) * | 1974-02-07 | 1977-12-13 | Smith Kline & French Laboratories Limited | Bis-guanidino-alkane compounds |
| US4137319A (en) * | 1974-02-07 | 1979-01-30 | Smith Kline & French Laboratories Limited | Guanidino, thioureido, isothioureido and nitrovinylamino derivatives of pyridine |
| GB1497260A (en) * | 1974-06-28 | 1978-01-05 | Smith Kline French Lab | Guanidine derivatives |
| US4151289A (en) * | 1975-01-22 | 1979-04-24 | Smith Kline & French Laboratories Limited | Nitromethylene amidino derivatives containing imidazole groups |
-
1974
- 1974-02-07 GB GB5596/74A patent/GB1493931A/en not_active Expired
-
1975
- 1975-01-08 CA CA217,572A patent/CA1062263A/en not_active Expired
- 1975-01-09 IE IE46/75A patent/IE40659B1/xx unknown
- 1975-01-10 ZA ZA00750180A patent/ZA75180B/xx unknown
- 1975-01-17 IL IL46451A patent/IL46451A/xx unknown
- 1975-01-20 DK DK14475*#A patent/DK14475A/da not_active Application Discontinuation
- 1975-01-20 AU AU77463/75A patent/AU500729B2/en not_active Expired
- 1975-01-22 US US05/542,971 patent/US3968227A/en not_active Expired - Lifetime
- 1975-01-28 NL NL7500977A patent/NL7500977A/xx not_active Application Discontinuation
- 1975-01-29 BE BE152829A patent/BE824923A/xx not_active IP Right Cessation
- 1975-02-04 SE SE7501208A patent/SE416050B/xx unknown
- 1975-02-05 FR FR7503629A patent/FR2260343B1/fr not_active Expired
- 1975-02-05 DE DE19752504794 patent/DE2504794A1/de not_active Ceased
- 1975-02-05 HU HU75SI1453A patent/HU174066B/hu unknown
- 1975-02-06 CH CH142375A patent/CH615916A5/de not_active IP Right Cessation
- 1975-02-06 PL PL1975177831A patent/PL98615B1/pl unknown
- 1975-02-06 NO NO750391A patent/NO143315C/no unknown
- 1975-02-06 LU LU71804A patent/LU71804A1/xx unknown
- 1975-02-07 ES ES434542A patent/ES434542A1/es not_active Expired
- 1975-02-07 JP JP50016800A patent/JPS5946219B2/ja not_active Expired
- 1975-05-12 ES ES437587A patent/ES437587A1/es not_active Expired
-
1979
- 1979-08-30 US US06/070,950 patent/US4301165A/en not_active Expired - Lifetime
-
1983
- 1983-06-30 US US06/509,563 patent/US4578388A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO750391L (en, 2012) | 1975-09-01 |
| NL7500977A (nl) | 1975-08-11 |
| PL98615B1 (pl) | 1978-05-31 |
| JPS50108259A (en, 2012) | 1975-08-26 |
| IL46451A0 (en) | 1975-04-25 |
| ZA75180B (en) | 1976-01-28 |
| US4578388A (en) | 1986-03-25 |
| IE40659B1 (en) | 1979-07-18 |
| DK14475A (en, 2012) | 1975-10-13 |
| IE40659L (en) | 1975-08-07 |
| FR2260343B1 (en, 2012) | 1978-07-21 |
| SE7501208L (en, 2012) | 1975-08-08 |
| BE824923A (fr) | 1975-07-29 |
| ES434542A1 (es) | 1976-12-16 |
| DE2504794A1 (de) | 1975-08-14 |
| SE416050B (sv) | 1980-11-24 |
| US3968227A (en) | 1976-07-06 |
| ES437587A1 (es) | 1977-01-16 |
| HU174066B (hu) | 1979-10-28 |
| NO143315C (no) | 1981-01-14 |
| AU7746375A (en) | 1976-07-22 |
| US4301165A (en) | 1981-11-17 |
| NO143315B (no) | 1980-10-06 |
| LU71804A1 (en, 2012) | 1975-06-24 |
| AU500729B2 (en) | 1979-05-31 |
| FR2260343A1 (en, 2012) | 1975-09-05 |
| GB1493931A (en) | 1977-11-30 |
| CA1062263A (en) | 1979-09-11 |
| JPS5946219B2 (ja) | 1984-11-10 |
| IL46451A (en) | 1980-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |