CH626883A5 - - Google Patents
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- CH626883A5 CH626883A5 CH620376A CH620376A CH626883A5 CH 626883 A5 CH626883 A5 CH 626883A5 CH 620376 A CH620376 A CH 620376A CH 620376 A CH620376 A CH 620376A CH 626883 A5 CH626883 A5 CH 626883A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- general formula
- methyl
- compounds
- radical
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 58
- -1 imidazolylethyl Chemical group 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical class C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical class C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 11
- 229960001340 histamine Drugs 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 7
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 7
- WSUNDBVVUCLXTG-UHFFFAOYSA-N methyl n-cyano-n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate Chemical compound N#CNC(SC)=NCCSCC=1NC=NC=1C WSUNDBVVUCLXTG-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 4
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 4
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- DXLMTSGRWOZYGK-UHFFFAOYSA-N 2-(2-aminoethyl)-1-cyano-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CC=1NC=NC=1CSCCNC(NC#N)=NCCN DXLMTSGRWOZYGK-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 2
- YZMPQYTWHVIBAP-UHFFFAOYSA-N 1-cyano-3-methoxy-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CONC(NC#N)=NCCSCC=1N=CNC=1C YZMPQYTWHVIBAP-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
- 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 2
- VJSUMPPMFYQOMP-UHFFFAOYSA-N 4-(1h-imidazol-5-yl)butan-1-amine Chemical compound NCCCCC1=CNC=N1 VJSUMPPMFYQOMP-UHFFFAOYSA-N 0.000 description 2
- OMFHWSSRMLQOPD-UHFFFAOYSA-N 4-(2-isothiocyanatoethylsulfanylmethyl)-5-methyl-1h-imidazole Chemical compound CC=1N=CNC=1CSCCN=C=S OMFHWSSRMLQOPD-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 229940125715 antihistaminic agent Drugs 0.000 description 2
- 125000003943 azolyl group Chemical group 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 2
- 229960000582 mepyramine Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZWEJKNIWMHIJDT-UHFFFAOYSA-N 1-(2-aminoethyl)-3-cyano-2-[4-(1h-imidazol-5-yl)butyl]guanidine Chemical compound NCCNC(NC#N)=NCCCCC1=CN=CN1 ZWEJKNIWMHIJDT-UHFFFAOYSA-N 0.000 description 1
- MVYWEDGZDCBFFD-UHFFFAOYSA-N 1-cyano-2-(2-hydroxyethyl)-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CC=1NC=NC=1CSCCNC(NC#N)=NCCO MVYWEDGZDCBFFD-UHFFFAOYSA-N 0.000 description 1
- UJOZRIYVHGQUQZ-UHFFFAOYSA-N 1-cyano-2-(2-methoxyethyl)-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound COCCN=C(NC#N)NCCSCC=1N=CNC=1C UJOZRIYVHGQUQZ-UHFFFAOYSA-N 0.000 description 1
- YVVSJCMRBKIOCF-UHFFFAOYSA-N 1-cyano-2-(4-hydroxybutyl)-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CC=1NC=NC=1CSCCNC(NC#N)=NCCCCO YVVSJCMRBKIOCF-UHFFFAOYSA-N 0.000 description 1
- KYSDVPPOKWXQGW-UHFFFAOYSA-N 1-cyano-2-[2-(methylamino)ethyl]-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CNCCN=C(NC#N)NCCSCC=1N=CNC=1C KYSDVPPOKWXQGW-UHFFFAOYSA-N 0.000 description 1
- CEDHTXTWYWZFMW-UHFFFAOYSA-N 1-cyano-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-(2-phenylethyl)guanidine Chemical compound N1C=NC(CSCCN=C(NCCC=2C=CC=CC=2)NC#N)=C1C CEDHTXTWYWZFMW-UHFFFAOYSA-N 0.000 description 1
- MTYFAKFAIIVEAW-UHFFFAOYSA-N 1-cyano-2-[4-(1h-imidazol-5-yl)butyl]-3-methoxyguanidine Chemical compound CONC(NC#N)=NCCCCC1=CN=CN1 MTYFAKFAIIVEAW-UHFFFAOYSA-N 0.000 description 1
- UWNVOMKEKFDVCQ-UHFFFAOYSA-N 1-cyano-3-(2-hydroxyethyl)-2-[4-(1h-imidazol-5-yl)butyl]guanidine Chemical compound OCCNC(NC#N)=NCCCCC1=CN=CN1 UWNVOMKEKFDVCQ-UHFFFAOYSA-N 0.000 description 1
- PNDGUFGDYSCXOD-UHFFFAOYSA-N 1-cyano-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-2-(2,2,2-trifluoroethyl)guanidine Chemical compound CC=1NC=NC=1CSCCNC(NC#N)=NCC(F)(F)F PNDGUFGDYSCXOD-UHFFFAOYSA-N 0.000 description 1
- CUGCPJNIIKYAJY-UHFFFAOYSA-N 1-cyano-3-[4-(1h-imidazol-5-yl)butyl]-2-(2,2,2-trifluoroethyl)guanidine Chemical compound FC(F)(F)CN=C(NC#N)NCCCCC1=CN=CN1 CUGCPJNIIKYAJY-UHFFFAOYSA-N 0.000 description 1
- KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- BQJWPWSQSOUOLY-UHFFFAOYSA-N 2-(12-aminododecyl)-1-cyano-3-[4-(1h-imidazol-5-yl)butyl]guanidine Chemical compound NCCCCCCCCCCCCN=C(NC#N)NCCCCC1=CN=CN1 BQJWPWSQSOUOLY-UHFFFAOYSA-N 0.000 description 1
- UNOWARGIBLHQIH-UHFFFAOYSA-N 2-(2-aminoethyl)-1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CC=1N=CNC=1CSCCNC(=N)NCCN UNOWARGIBLHQIH-UHFFFAOYSA-N 0.000 description 1
- KJZKMRRDZVWONS-UHFFFAOYSA-N 2-(8-aminooctyl)-1-cyano-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CC=1NC=NC=1CSCCNC(NC#N)=NCCCCCCCCN KJZKMRRDZVWONS-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 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
- PQVHMOLNSYFXIJ-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]pyrazole-3-carboxylic acid Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(N1CC2=C(CC1)NN=N2)=O)C(=O)O PQVHMOLNSYFXIJ-UHFFFAOYSA-N 0.000 description 1
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 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
- 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 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- WJAJPNHVVFWKKL-UHFFFAOYSA-N Methoxamine Chemical compound COC1=CC=C(OC)C(C(O)C(C)N)=C1 WJAJPNHVVFWKKL-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 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
- 239000005700 Putrescine Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000003957 anion exchange resin Substances 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
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000000748 cardiovascular system Anatomy 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
- 239000012230 colorless oil Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- OWEZJUPKTBEISC-UHFFFAOYSA-N decane-1,1-diamine Chemical compound CCCCCCCCCC(N)N OWEZJUPKTBEISC-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 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
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229960005192 methoxamine Drugs 0.000 description 1
- GFBQTIUVGUWMKD-UHFFFAOYSA-N methyl n'-cyano-n-methoxycarbamimidothioate Chemical compound CON=C(SC)NC#N GFBQTIUVGUWMKD-UHFFFAOYSA-N 0.000 description 1
- MXRRFLNFYRKHSW-UHFFFAOYSA-N methyl n-cyano-n'-(2,2,2-trifluoroethyl)carbamimidothioate Chemical compound N#CNC(SC)=NCC(F)(F)F MXRRFLNFYRKHSW-UHFFFAOYSA-N 0.000 description 1
- CSTUIXPBMVBAJM-UHFFFAOYSA-N methyl n-cyano-n'-[4-(1h-imidazol-5-yl)butyl]carbamimidothioate Chemical compound N#CNC(SC)=NCCCCC1=CNC=N1 CSTUIXPBMVBAJM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 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
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- IHMQNZFRFVYNDS-UHFFFAOYSA-N tert-butyl n-amino-n-methylcarbamate Chemical compound CN(N)C(=O)OC(C)(C)C IHMQNZFRFVYNDS-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21817/75A GB1553070A (en) | 1975-05-21 | 1975-05-21 | Thiourea guanidine and 1-nitro-2,2-diaminoethylene derivatives |
| GB4778275 | 1975-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626883A5 true CH626883A5 (en, 2012) | 1981-12-15 |
Family
ID=26255540
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH620376A CH626883A5 (en, 2012) | 1975-05-21 | 1976-05-18 | |
| CH388580A CH624941A5 (en, 2012) | 1975-05-21 | 1980-05-19 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH388580A CH624941A5 (en, 2012) | 1975-05-21 | 1980-05-19 |
Country Status (13)
| Country | Link |
|---|---|
| US (6) | US4098898A (en, 2012) |
| JP (1) | JPS51141865A (en, 2012) |
| AT (1) | AT356131B (en, 2012) |
| AU (1) | AU503525B2 (en, 2012) |
| CA (1) | CA1076581A (en, 2012) |
| CH (2) | CH626883A5 (en, 2012) |
| DE (1) | DE2621834A1 (en, 2012) |
| DK (1) | DK145541C (en, 2012) |
| FR (1) | FR2311536A1 (en, 2012) |
| IE (1) | IE44062B1 (en, 2012) |
| IL (1) | IL49528A (en, 2012) |
| NL (1) | NL7605405A (en, 2012) |
| SE (1) | SE419544B (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4170652A (en) * | 1974-03-12 | 1979-10-09 | Smith Kline & French Laboratories Limited | Heterocyclic-methylthioalkyl-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 |
| DE2905134A1 (de) * | 1978-02-17 | 1979-08-23 | Degussa | Neue acylierte aminoalkyl-cyanoguanidine mit einem heterocyclischen rest |
| IL57415A (en) * | 1978-05-30 | 1984-08-31 | Smith Kline French Lab | Nitropyrrole compounds,process for preparing them and pharmaceutical compositions containing them |
| US4200760A (en) * | 1978-09-26 | 1980-04-29 | Bristol-Myers Company | Imidazolylalkylthioalkylamino-ethylene derivatives |
| DE2966646D1 (en) * | 1978-10-16 | 1984-03-15 | Ici Plc | Antisecretory branched-chain heterocyclic guanidine derivatives, processes for their manufacture, intermediates, and pharmaceutical compositions containing said derivatives |
| US4282363A (en) * | 1978-11-24 | 1981-08-04 | Bristol-Myers Company | 1-Nitro-2-(2-alkynylamino)-2-[(2-pyridylmethylthio)-ethylamino]ethylene derivatives |
| JPS568357A (en) * | 1979-02-16 | 1981-01-28 | Eisai Co Ltd | Cyanoguanidine derivative and its production |
| US4220654A (en) * | 1979-06-04 | 1980-09-02 | Merck & Co., Inc. | Cyclic imidazole cyanoguanidines |
| US4394508A (en) * | 1980-06-07 | 1983-07-19 | Bristol-Myers Company | Chemical compounds |
| US4315024A (en) * | 1980-08-08 | 1982-02-09 | Cooper Laboratories, Inc. | Compositions and method for treating red eye |
| US4382090A (en) * | 1980-10-02 | 1983-05-03 | Eli Lilly And Company | N-Thiazolylmethylthioalkyl-N'alkylamidines and related compounds |
| US4443456A (en) * | 1981-05-12 | 1984-04-17 | William H. Rorer, Inc. | Pyridyl alkylene amidinoureas |
| US4810717A (en) * | 1981-11-12 | 1989-03-07 | E. I. Du Pont De Nemours And Company | 2-hydroxypropylamine aryl ester derivatives |
| DE3232462A1 (de) * | 1982-09-01 | 1984-03-01 | Bayer Ag, 5090 Leverkusen | 2-nitro-1,1-ethendiamine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| US4560690A (en) * | 1984-04-30 | 1985-12-24 | Pfizer Inc. | 2-(N-substituted guanidino)-4-hetero-arylthiazole antiulcer agents |
| US4795719A (en) * | 1984-05-15 | 1989-01-03 | Waferscale Integration, Inc. | Self-aligned split gate eprom process |
| DE3579000D1 (de) * | 1985-04-02 | 1990-09-06 | Heumann Pharma Gmbh & Co | Imidazolylalkylguanidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
| US4617311A (en) * | 1985-05-17 | 1986-10-14 | Eli Lilly And Company | Antiasthmatic method |
| NL8601585A (nl) * | 1986-06-19 | 1988-01-18 | Vereniging Voor Christelijk Wetenschappelijk Onderwijs | N-(2-gesubstitueerde alkyl)-n-imidazol-4-yl alkyl guanidine. |
| DE3631334A1 (de) * | 1986-09-15 | 1988-03-17 | Heumann Pharma Gmbh & Co | Neue imidazolylguanidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4996221A (en) * | 1987-01-13 | 1991-02-26 | The Board Of Trustees Of The Leland Stanford Junior University | Histamine derivatives as immune modulators |
| US5145860A (en) * | 1989-01-05 | 1992-09-08 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole compounds and pharmaceutical composition comprising the same |
| US5229386A (en) * | 1989-01-05 | 1993-07-20 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole compounds, processes for the preparation thereof and pharmaceutical composition comprising the same |
| EP0573542B1 (en) * | 1991-02-27 | 1997-10-15 | Seed Capital Investments( Sci) B.V. | Imidazole-derivatives having antagonistic activity on the histamine h3-receptor |
| NL9100365A (nl) * | 1991-02-27 | 1992-09-16 | Seed Capital Investments | Imidazoolderivaten met agonistische of antagonistische activiteit op de histamine h3-receptor. |
| AU3467493A (en) * | 1992-01-27 | 1993-09-01 | Board Of Trustees Of The Leland Stanford Junior University | Histamine derivatives and methods for their use |
| US5808090A (en) * | 1996-02-22 | 1998-09-15 | Endo Pharmaceuticals Inc. | Process for preventing precipitation in cimetidine injection solutions |
| EP1116486A4 (en) * | 1998-09-22 | 2007-06-20 | Ishihara Sangyo Kaisha | MEDICAL COMPOSITION CONTAINING NITROETHENAMINE DERIVATIVES OR SALTS AS ACTIVE INGREDIENTS |
| GB0404434D0 (en) | 2004-02-27 | 2004-03-31 | Novartis Ag | Organic compounds |
| 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 (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968216A (en) * | 1969-10-29 | 1976-07-06 | Smith Kline & French Laboratories Limited | Method of inhibiting histamine activity with guanidine compounds |
| US3868457A (en) * | 1969-10-29 | 1975-02-25 | Smith Kline French Lab | Method of inhibiting histamine activity with guanidine compounds |
| GB1305549A (en, 2012) * | 1969-10-29 | 1973-02-07 | ||
| US3808336A (en) * | 1970-06-25 | 1974-04-30 | Smithkline Corp | Pharmaceutical compositions and methods of inhibiting histamine activity with thiourea derivatives |
| US3905984A (en) * | 1971-03-09 | 1975-09-16 | Smith Kline French Lab | Pyridyl substituted thioalkyl-and oxyalkyl-thioureas and ureas |
| US3950353A (en) * | 1971-03-09 | 1976-04-13 | Smith Kline & French Laboratories Limited | Pharmacologically active thiourea and urea compounds |
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| US4000302A (en) * | 1972-04-20 | 1976-12-28 | Smith Kline & French Laboratories Limited | Pharmaceutical compositions and methods of inhibiting H-1 and H-2 histamine receptors |
| US4000296A (en) * | 1972-09-05 | 1976-12-28 | Smith Kline & French Laboratories Limited | Imidazole alkylguanidine compounds |
| US3979398A (en) * | 1973-02-08 | 1976-09-07 | Smith Kline & French Laboratories Limited | Sulphoxides |
| GB1421792A (en) * | 1973-05-17 | 1976-01-21 | Smith Kline French Lab | Heterocyclic substituted-1, 1-diamino-ethylene derivatives methods for their preparation and compositions containing them |
| US4124717A (en) * | 1973-05-17 | 1978-11-07 | Smith Kline & French Laboratories Limited | Thiazolyl alkylaminoethylene compounds |
| US4046907A (en) * | 1973-05-17 | 1977-09-06 | Smith Kline & French Laboratories Limited | Imidazole alkylaminoethylene compounds |
| GB1431589A (en) * | 1973-07-13 | 1976-04-07 | Smith Kline French Lab | Ureas, thioureas and guanidines n,n-disubstituted by heterocyclo- alkylene and/or heterocycloalkylenethioalkylene groups |
| US4152443A (en) * | 1973-07-13 | 1979-05-01 | Smith Kline & French Laboratories Limited | Imidazolyl thioureas, ureas and guanidines |
| GB1493931A (en) * | 1974-02-07 | 1977-11-30 | Smith Kline French Lab | Guanidines isothioureas and thioureas |
| US4109003A (en) * | 1974-03-12 | 1978-08-22 | Smith Kline & French Laboratories Limited | Pharmacologically active compounds |
| US4013769A (en) * | 1974-05-09 | 1977-03-22 | Smith Kline & French Laboratories Limited | Pyridyl-alkylaminoethylene compounds |
| GB1497260A (en) * | 1974-06-28 | 1978-01-05 | Smith Kline French Lab | Guanidine derivatives |
| US4093621A (en) * | 1974-09-02 | 1978-06-06 | Smith Kline & French Laboratories Limited | Process for preparing heterocyclicalkylthioalkyl-N-cyanoguanidines 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 |
| US4154838A (en) * | 1975-07-31 | 1979-05-15 | Smith Kline & French Laboratories Limited | Alkoxy pyridine |
| 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 |
-
1976
- 1976-05-06 IL IL49528A patent/IL49528A/xx unknown
- 1976-05-10 DK DK206576A patent/DK145541C/da not_active IP Right Cessation
- 1976-05-11 CA CA252,248A patent/CA1076581A/en not_active Expired
- 1976-05-13 US US05/686,185 patent/US4098898A/en not_active Expired - Lifetime
- 1976-05-14 JP JP51056418A patent/JPS51141865A/ja active Pending
- 1976-05-17 DE DE19762621834 patent/DE2621834A1/de not_active Ceased
- 1976-05-18 SE SE7605620A patent/SE419544B/xx unknown
- 1976-05-18 CH CH620376A patent/CH626883A5/de not_active IP Right Cessation
- 1976-05-18 AT AT361576A patent/AT356131B/de not_active IP Right Cessation
- 1976-05-20 NL NL7605405A patent/NL7605405A/xx not_active Application Discontinuation
- 1976-05-20 FR FR7615253A patent/FR2311536A1/fr active Granted
- 1976-05-20 IE IE1068/76A patent/IE44062B1/en unknown
- 1976-05-21 AU AU14195/76A patent/AU503525B2/en not_active Expired
-
1979
- 1979-05-02 US US06/035,152 patent/US4247558A/en not_active Expired - Lifetime
- 1979-08-27 US US06/070,184 patent/US4276301A/en not_active Expired - Lifetime
-
1980
- 1980-05-19 CH CH388580A patent/CH624941A5/de not_active IP Right Cessation
- 1980-09-02 US US06/183,555 patent/US4347250A/en not_active Expired - Lifetime
-
1981
- 1981-01-29 US US06/229,435 patent/US4333946A/en not_active Expired - Lifetime
-
1982
- 1982-06-18 US US06/389,837 patent/US4440775A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE7605620L (sv) | 1976-11-22 |
| ATA361576A (de) | 1979-09-15 |
| US4440775A (en) | 1984-04-03 |
| US4247558A (en) | 1981-01-27 |
| US4276301A (en) | 1981-06-30 |
| DE2621834A1 (de) | 1976-12-02 |
| CA1076581A (en) | 1980-04-29 |
| SE419544B (sv) | 1981-08-10 |
| FR2311536A1 (fr) | 1976-12-17 |
| DK145541C (da) | 1983-05-16 |
| NL7605405A (nl) | 1976-11-23 |
| AT356131B (de) | 1980-04-10 |
| FR2311536B1 (en, 2012) | 1979-03-23 |
| CH624941A5 (en, 2012) | 1981-08-31 |
| DK206576A (da) | 1976-11-22 |
| AU1419576A (en) | 1977-11-24 |
| IL49528A0 (en) | 1976-07-30 |
| US4347250A (en) | 1982-08-31 |
| AU503525B2 (en) | 1979-09-06 |
| JPS51141865A (en) | 1976-12-07 |
| IE44062B1 (en) | 1981-08-12 |
| IE44062L (en) | 1976-11-21 |
| US4333946A (en) | 1982-06-08 |
| DK145541B (da) | 1982-12-06 |
| US4098898A (en) | 1978-07-04 |
| IL49528A (en) | 1980-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |