CH624387A5 - - Google Patents
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- Publication number
- CH624387A5 CH624387A5 CH1493776A CH1493776A CH624387A5 CH 624387 A5 CH624387 A5 CH 624387A5 CH 1493776 A CH1493776 A CH 1493776A CH 1493776 A CH1493776 A CH 1493776A CH 624387 A5 CH624387 A5 CH 624387A5
- Authority
- CH
- Switzerland
- Prior art keywords
- general formula
- isothiourea
- group
- pentyl
- urea
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 41
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 32
- -1 p-toluenesulfonyloxy Chemical group 0.000 claims description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 14
- 150000003672 ureas Chemical class 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- CPPIWIKWMQPFHY-UHFFFAOYSA-N 6-(methylcarbamothioylamino)hexyl carbamimidothioate Chemical compound CNC(=S)NCCCCCCSC(N)=N CPPIWIKWMQPFHY-UHFFFAOYSA-N 0.000 claims description 3
- XIAUYDGHFGJJHM-UHFFFAOYSA-N 5-(methylcarbamothioylamino)pentyl carbamimidothioate Chemical compound CNC(=S)NCCCCCSC(N)=N XIAUYDGHFGJJHM-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229960001340 histamine Drugs 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 4
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 3
- ZLBQWEZICKDVTJ-UHFFFAOYSA-N 1-cyano-3-(5-hydroxypentyl)-2-methylguanidine Chemical compound N#CNC(=NC)NCCCCCO ZLBQWEZICKDVTJ-UHFFFAOYSA-N 0.000 description 3
- YLKQOIAYNHSOJU-UHFFFAOYSA-N 2-sulfanylideneimidazolidine-4,5-dione Chemical compound O=C1NC(=S)NC1=O YLKQOIAYNHSOJU-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- 206010015150 Erythema Diseases 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 229940125715 antihistaminic agent Drugs 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 231100000321 erythema Toxicity 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000007788 liquid Substances 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
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- DHGWBERWXYHGKU-UHFFFAOYSA-N 1-methyl-2-sulfanylideneimidazolidine-4,5-dione Chemical compound CN1C(=S)NC(=O)C1=O DHGWBERWXYHGKU-UHFFFAOYSA-N 0.000 description 2
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 2
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ACOWUXLCNNHFCQ-UHFFFAOYSA-N [amino(sulfanyl)methylidene]azanium;acetate Chemical compound CC(O)=O.NC(N)=S ACOWUXLCNNHFCQ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- GMEGXJPUFRVCPX-UHFFFAOYSA-N butylthiourea Chemical compound CCCCNC(N)=S GMEGXJPUFRVCPX-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000005457 ice water Substances 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- MHGGQXIPBPGZFB-UHFFFAOYSA-N methyl n-cyano-n'-methylcarbamimidothioate Chemical compound CSC(=NC)NC#N MHGGQXIPBPGZFB-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YQFHPXZGXNYYLD-ARJAWSKDSA-N (z)-n-methyl-1-methylsulfanyl-2-nitroethenamine Chemical group CN\C(SC)=C\[N+]([O-])=O YQFHPXZGXNYYLD-ARJAWSKDSA-N 0.000 description 1
- NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 1
- MQJFVJYVRBHFMO-UHFFFAOYSA-N 1,3-bis(5-bromopentyl)-2-sulfanylideneimidazolidine-4,5-dione Chemical compound BrCCCCCN1C(=O)C(=O)N(CCCCCBr)C1=S MQJFVJYVRBHFMO-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- NPEIGRBGMUJNFE-UHFFFAOYSA-N 1-aminohexan-1-ol Chemical compound CCCCCC(N)O NPEIGRBGMUJNFE-UHFFFAOYSA-N 0.000 description 1
- RZOQGWRLVITGRA-UHFFFAOYSA-N 1-butyl-2-sulfanylideneimidazolidine-4,5-dione Chemical compound CCCCN1C(=S)NC(=O)C1=O RZOQGWRLVITGRA-UHFFFAOYSA-N 0.000 description 1
- FKUJZARUPJNYHX-UHFFFAOYSA-N 1-cyano-2,3-bis(5-hydroxypentyl)guanidine Chemical compound OCCCCCNC(NC#N)=NCCCCCO FKUJZARUPJNYHX-UHFFFAOYSA-N 0.000 description 1
- XCMCNNUGKXUALQ-UHFFFAOYSA-N 4-(methylcarbamothioylamino)butyl carbamimidothioate Chemical compound CNC(=S)NCCCCSC(N)=N XCMCNNUGKXUALQ-UHFFFAOYSA-N 0.000 description 1
- IQXHDJZSKCEKOD-UHFFFAOYSA-N 5-(butylcarbamothioylamino)pentyl carbamimidothioate Chemical compound CCCCNC(=S)NCCCCCSC(N)=N IQXHDJZSKCEKOD-UHFFFAOYSA-N 0.000 description 1
- ZXEIREYZJNZFSE-UHFFFAOYSA-N 5-[(n-cyano-n'-methylcarbamimidoyl)amino]pentyl carbamimidothioate Chemical compound N#CNC(=NC)NCCCCCSC(N)=N ZXEIREYZJNZFSE-UHFFFAOYSA-N 0.000 description 1
- WWTDZSQUZVXGBH-UHFFFAOYSA-N 5-[[butylamino-(cyanoamino)methylidene]amino]pentyl carbamimidothioate Chemical compound CCCCNC(NC#N)=NCCCCCSC(N)=N WWTDZSQUZVXGBH-UHFFFAOYSA-N 0.000 description 1
- QFHCELMVNDUYAQ-UHFFFAOYSA-N 6-(methylcarbamothioylamino)hexyl carbamimidothioate;hydrochloride Chemical compound Cl.CNC(=S)NCCCCCCSC(N)=N QFHCELMVNDUYAQ-UHFFFAOYSA-N 0.000 description 1
- CGQWZGJQUCETFX-UHFFFAOYSA-N 6-[(n-cyano-n'-methylcarbamimidoyl)amino]hexyl carbamimidothioate Chemical compound N#CNC(=NC)NCCCCCCSC(N)=N CGQWZGJQUCETFX-UHFFFAOYSA-N 0.000 description 1
- RCJOENWISFABAU-UHFFFAOYSA-N 7-(methylamino)-8-nitrooct-7-en-1-ol Chemical group [O-][N+](=O)C=C(NC)CCCCCCO RCJOENWISFABAU-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 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
- 206010061218 Inflammation Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- CEWQUQHDVFQEFZ-UHFFFAOYSA-N [O-][N+](=O)C=C(NC)NCCCCCCSC(N)=N Chemical compound [O-][N+](=O)C=C(NC)NCCCCCCSC(N)=N CEWQUQHDVFQEFZ-UHFFFAOYSA-N 0.000 description 1
- NFQOXNYLFKESQD-UHFFFAOYSA-N [O-][N+](=O)C=C(NC)NCCCCCSC(N)=N Chemical compound [O-][N+](=O)C=C(NC)NCCCCCSC(N)=N NFQOXNYLFKESQD-UHFFFAOYSA-N 0.000 description 1
- GZKCKEWTZYJDFL-UHFFFAOYSA-N [O-][N+](=O)C=C(NC)NCCCCSC(N)=N Chemical compound [O-][N+](=O)C=C(NC)NCCCCSC(N)=N GZKCKEWTZYJDFL-UHFFFAOYSA-N 0.000 description 1
- BEDFFIGLKDBKJA-UHFFFAOYSA-N [O-][N+](=O)C=C(NC)NCCCSC(N)=N Chemical compound [O-][N+](=O)C=C(NC)NCCCSC(N)=N BEDFFIGLKDBKJA-UHFFFAOYSA-N 0.000 description 1
- ZUEIQJQVPAVNNO-UHFFFAOYSA-N [amino-[3-(methylcarbamothioylamino)propylsulfanyl]methylidene]azanium;acetate Chemical compound CC([O-])=O.CNC(=S)NCCCSC(N)=[NH2+] ZUEIQJQVPAVNNO-UHFFFAOYSA-N 0.000 description 1
- NNOPOLUXUZVUQD-UHFFFAOYSA-N [amino-[5-(methylcarbamothioylamino)pentylsulfanyl]methylidene]azanium;acetate;hydrate Chemical compound O.CC([O-])=O.CNC(=S)NCCCCCSC(N)=[NH2+] NNOPOLUXUZVUQD-UHFFFAOYSA-N 0.000 description 1
- MIBJTIVXZDPFDY-UHFFFAOYSA-N [amino-[6-(methylcarbamothioylamino)hexylsulfanyl]methylidene]azanium;acetate Chemical compound CC([O-])=O.CNC(=S)NCCCCCCSC(N)=[NH2+] MIBJTIVXZDPFDY-UHFFFAOYSA-N 0.000 description 1
- ZMAFQCCYKBMPMB-UHFFFAOYSA-N [amino-[6-(methylcarbamothioylamino)hexylsulfanyl]methylidene]azanium;acetate;hydrate Chemical compound O.CC([O-])=O.CNC(=S)NCCCCCCSC(N)=[NH2+] ZMAFQCCYKBMPMB-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 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
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000005557 antagonist 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 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
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 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
- 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
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 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
- 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
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 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
- 230000001678 irradiating effect Effects 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
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate 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
- DLRNKOGRAMLADX-UHFFFAOYSA-N methyl n'-butyl-n-cyanocarbamimidothioate Chemical compound CCCCN=C(SC)NC#N DLRNKOGRAMLADX-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 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
- 235000005985 organic acids 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000011593 sulfur Substances 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
- 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
- INDZTCRIYSRWOH-UHFFFAOYSA-N undec-10-enyl carbamimidothioate;hydroiodide Chemical compound I.NC(=N)SCCCCCCCCCC=C INDZTCRIYSRWOH-UHFFFAOYSA-N 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
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- 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
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB49248/75A GB1578219A (en) | 1975-12-01 | 1975-12-01 | Isothioureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624387A5 true CH624387A5 (da) | 1981-07-31 |
Family
ID=10451685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1493776A CH624387A5 (da) | 1975-12-01 | 1976-11-26 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4084001A (da) |
| JP (1) | JPS5268128A (da) |
| AT (1) | AT351559B (da) |
| AU (1) | AU509662B2 (da) |
| BE (1) | BE848909A (da) |
| CA (1) | CA1083171A (da) |
| CH (1) | CH624387A5 (da) |
| DE (1) | DE2654515A1 (da) |
| DK (1) | DK517476A (da) |
| ES (1) | ES453801A1 (da) |
| FI (1) | FI64800C (da) |
| FR (1) | FR2375206A1 (da) |
| GB (1) | GB1578219A (da) |
| HU (1) | HU176328B (da) |
| IE (1) | IE44358B1 (da) |
| IL (1) | IL50874A (da) |
| LU (1) | LU76285A1 (da) |
| NL (1) | NL7613093A (da) |
| NO (1) | NO142525C (da) |
| PT (1) | PT65839B (da) |
| SE (1) | SE7613382L (da) |
| ZA (1) | ZA766778B (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4158013A (en) * | 1977-06-03 | 1979-06-12 | Bristol-Myers Company | N-Cyano-N'-alkynyl-N"-2-mercaptoethylguanidines |
| US4157340A (en) * | 1978-06-27 | 1979-06-05 | Bristol-Meyers Company | N,N'-[Bis(N-cyanoguanyl)]cystamine derivatives |
| ZA793392B (en) * | 1978-07-15 | 1980-08-27 | Smith Kline French Lab | Isoureas and isothioureas |
| DE3431923A1 (de) * | 1984-08-30 | 1986-03-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von sulvonyliso(thio)harnstoffen |
| US7115620B2 (en) | 2001-10-30 | 2006-10-03 | Wyeth | 1,3-disubstituted-2-thioxo-imidazolidine-4,5-diones as potassium channel openers |
| US7135492B2 (en) * | 2001-10-30 | 2006-11-14 | Wyeth | 1,3-disubstituted-2- thioxo-imidazolidine-4,5-dione derivatives useful in the treatment of atherosclerosis |
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3669670A (en) * | 1970-12-02 | 1972-06-13 | Eastman Kodak Co | Photographic compositions containing bis-isothiuronium compounds as development activators and image stabilizers |
-
1975
- 1975-12-01 GB GB49248/75A patent/GB1578219A/en not_active Expired
-
1976
- 1976-11-09 IL IL50874A patent/IL50874A/xx unknown
- 1976-11-11 ZA ZA766778A patent/ZA766778B/xx unknown
- 1976-11-15 PT PT65839A patent/PT65839B/pt unknown
- 1976-11-17 DK DK517476A patent/DK517476A/da not_active Application Discontinuation
- 1976-11-23 US US05/744,584 patent/US4084001A/en not_active Expired - Lifetime
- 1976-11-24 NL NL7613093A patent/NL7613093A/xx not_active Application Discontinuation
- 1976-11-25 AT AT875176A patent/AT351559B/de not_active IP Right Cessation
- 1976-11-25 JP JP51142102A patent/JPS5268128A/ja active Pending
- 1976-11-26 CH CH1493776A patent/CH624387A5/de not_active IP Right Cessation
- 1976-11-29 HU HU76SI1553A patent/HU176328B/hu unknown
- 1976-11-29 CA CA266,796A patent/CA1083171A/en not_active Expired
- 1976-11-29 LU LU76285A patent/LU76285A1/xx unknown
- 1976-11-30 BE BE172841A patent/BE848909A/xx not_active IP Right Cessation
- 1976-11-30 ES ES453801A patent/ES453801A1/es not_active Expired
- 1976-11-30 NO NO764084A patent/NO142525C/no unknown
- 1976-11-30 SE SE7613382A patent/SE7613382L/xx not_active Application Discontinuation
- 1976-12-01 FR FR7636265A patent/FR2375206A1/fr active Granted
- 1976-12-01 DE DE19762654515 patent/DE2654515A1/de not_active Withdrawn
- 1976-12-01 IE IE2635/76A patent/IE44358B1/en unknown
- 1976-12-01 FI FI763458A patent/FI64800C/fi not_active IP Right Cessation
- 1976-12-01 AU AU20153/76A patent/AU509662B2/en not_active Expired
-
1978
- 1978-08-10 US US05/933,254 patent/USRE30457E/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL7613093A (nl) | 1977-06-03 |
| IL50874A0 (en) | 1977-01-31 |
| FI64800C (fi) | 1984-01-10 |
| DE2654515A1 (de) | 1977-06-02 |
| US4084001A (en) | 1978-04-11 |
| FR2375206B1 (da) | 1980-03-07 |
| FI64800B (fi) | 1983-09-30 |
| ZA766778B (en) | 1977-10-26 |
| AT351559B (de) | 1979-08-10 |
| PT65839B (en) | 1978-05-15 |
| CA1083171A (en) | 1980-08-05 |
| JPS5268128A (en) | 1977-06-06 |
| AU509662B2 (en) | 1980-05-22 |
| USRE30457E (en) | 1980-12-23 |
| AU2015376A (en) | 1978-06-08 |
| DK517476A (da) | 1977-06-02 |
| HU176328B (en) | 1981-01-28 |
| NO142525B (no) | 1980-05-27 |
| IE44358B1 (en) | 1981-11-04 |
| SE7613382L (sv) | 1977-06-02 |
| NO142525C (no) | 1980-09-03 |
| IE44358L (en) | 1977-06-01 |
| IL50874A (en) | 1981-06-29 |
| NO764084L (da) | 1977-06-02 |
| FI763458A (da) | 1977-06-02 |
| ES453801A1 (es) | 1977-11-01 |
| PT65839A (en) | 1976-12-01 |
| FR2375206A1 (fr) | 1978-07-21 |
| GB1578219A (en) | 1980-11-05 |
| LU76285A1 (da) | 1977-05-20 |
| ATA875176A (de) | 1979-01-15 |
| BE848909A (fr) | 1977-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |