CS207791B2 - Method of making the derivatives of the thiadiazole - Google Patents
Method of making the derivatives of the thiadiazole Download PDFInfo
- Publication number
- CS207791B2 CS207791B2 CS798890A CS889079A CS207791B2 CS 207791 B2 CS207791 B2 CS 207791B2 CS 798890 A CS798890 A CS 798890A CS 889079 A CS889079 A CS 889079A CS 207791 B2 CS207791 B2 CS 207791B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- sub
- sup
- formula
- ethanol
- thiadiazole
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 title description 2
- -1 3,4-dioxocyclobuten-1,2-diyl Chemical group 0.000 claims abstract description 20
- 150000004867 thiadiazoles Chemical class 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 101000989653 Homo sapiens Membrane frizzled-related protein Proteins 0.000 claims 1
- 102100029357 Membrane frizzled-related protein Human genes 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 229960001340 histamine Drugs 0.000 description 15
- 238000012360 testing method Methods 0.000 description 13
- DHWAIXOKMZVONM-UHFFFAOYSA-N 2-[3-(chloromethyl)-1,2,4-thiadiazol-5-yl]guanidine Chemical compound NC(=N)NC1=NC(CCl)=NS1 DHWAIXOKMZVONM-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 210000004211 gastric acid Anatomy 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000000739 antihistaminic agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- OOQXOCKWFGBDJZ-UHFFFAOYSA-N methyl N-cyano-N'-[2-[[5-(diaminomethylideneamino)-1,2,4-thiadiazol-3-yl]methylsulfanyl]ethyl]carbamimidothioate Chemical compound N#CN=C(SC)NCCSCC1=NSC(NC(N)=N)=N1 OOQXOCKWFGBDJZ-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000028327 secretion Effects 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- QLXYXDYEGPBKGC-UHFFFAOYSA-N 1-cyano-3-[2-[[5-(diaminomethylideneamino)-1,2,4-thiadiazol-3-yl]methylsulfanyl]ethyl]-2-methylguanidine Chemical compound N#CNC(=NC)NCCSCC1=NSC(N=C(N)N)=N1 QLXYXDYEGPBKGC-UHFFFAOYSA-N 0.000 description 3
- DTYGMVDUWOQADZ-UHFFFAOYSA-N 2-[3-(2-aminoethylsulfanylmethyl)-1,2,4-thiadiazol-5-yl]guanidine Chemical compound NCCSCC1=NSC(NC(N)=N)=N1 DTYGMVDUWOQADZ-UHFFFAOYSA-N 0.000 description 3
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 3
- 208000007107 Stomach Ulcer Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 229960000582 mepyramine Drugs 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
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FFFMIFUBJZBTCG-UHFFFAOYSA-N 5-chloro-3-(chloromethyl)-1,2,4-thiadiazole Chemical compound ClCC1=NSC(Cl)=N1 FFFMIFUBJZBTCG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 206010016717 Fistula Diseases 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 229940125715 antihistaminic agent Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229960001380 cimetidine Drugs 0.000 description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229960000520 diphenhydramine Drugs 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000003890 fistula Effects 0.000 description 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000012289 standard assay Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical group C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 1
- WIDYUOLMGUXGCI-UHFFFAOYSA-N 1-[2-[[5-(diaminomethylideneamino)-1,2,4-thiadiazol-3-yl]methylsulfanyl]ethyl]-2-methyl-3-methylsulfonylguanidine Chemical compound CS(=O)(=O)N=C(NC)NCCSCC1=NSC(NC(N)=N)=N1 WIDYUOLMGUXGCI-UHFFFAOYSA-N 0.000 description 1
- WFXMNXFVOHZOJO-UHFFFAOYSA-N 1-[2-[[5-(diaminomethylideneamino)-1,2,4-thiadiazol-3-yl]methylsulfanyl]ethyl]-3-methylthiourea Chemical compound CNC(=S)NCCSCC1=NSC(NC(N)=N)=N1 WFXMNXFVOHZOJO-UHFFFAOYSA-N 0.000 description 1
- WRWJRDFHQMWOOZ-UHFFFAOYSA-N 1-cyano-3-[2-[[5-(diaminomethylideneamino)-1,2,4-thiadiazol-3-yl]methylsulfanyl]ethyl]-2-(2-hydroxyethyl)guanidine Chemical compound NC(=N)NC1=NC(CSCCNC(NCCO)=NC#N)=NS1 WRWJRDFHQMWOOZ-UHFFFAOYSA-N 0.000 description 1
- QAOBBBBDJSWHMU-WMBBNPMCSA-N 16,16-dimethylprostaglandin E2 Chemical compound CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O QAOBBBBDJSWHMU-WMBBNPMCSA-N 0.000 description 1
- YHGQSSZRJOYWTK-UHFFFAOYSA-N 2-[2-[[5-(diaminomethylideneamino)-1,2,4-thiadiazol-3-yl]methylsulfanyl]ethyl]-1-nitroguanidine Chemical compound NC(=N)NC1=NC(CSCCNC(N)=N[N+]([O-])=O)=NS1 YHGQSSZRJOYWTK-UHFFFAOYSA-N 0.000 description 1
- MCYVEDVDEJHPMX-UHFFFAOYSA-N 2-[3-(2-aminoethylsulfanylmethyl)-1,2,4-thiadiazol-5-yl]guanidine;oxalic acid Chemical compound OC(=O)C(O)=O.NCCSCC1=NSC(NC(N)=N)=N1 MCYVEDVDEJHPMX-UHFFFAOYSA-N 0.000 description 1
- PJOFOTWDXSEJTF-UHFFFAOYSA-N 2-[3-[2-[[2-(methylamino)-3,4-dioxocyclobuten-1-yl]amino]ethylsulfanylmethyl]-1,2,4-thiadiazol-5-yl]guanidine Chemical compound O=C1C(=O)C(NC)=C1NCCSCC1=NSC(N=C(N)N)=N1 PJOFOTWDXSEJTF-UHFFFAOYSA-N 0.000 description 1
- SZBNZTGCAMLMJY-UHFFFAOYSA-N 3,4-dimethoxycyclobut-3-ene-1,2-dione Chemical compound COC1=C(OC)C(=O)C1=O SZBNZTGCAMLMJY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- GMEDUXHKSSWXSL-UHFFFAOYSA-N 3-sulfanylpropylazanium;chloride Chemical compound Cl.NCCCS GMEDUXHKSSWXSL-UHFFFAOYSA-N 0.000 description 1
- ILTLLMVRPBXCSX-UHFFFAOYSA-N 5-chloro-3-methyl-1,2,4-thiadiazole Chemical compound CC1=NSC(Cl)=N1 ILTLLMVRPBXCSX-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C([O-])=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000012671 Gastrointestinal haemorrhages Diseases 0.000 description 1
- 102000003834 Histamine H1 Receptors Human genes 0.000 description 1
- 108090000110 Histamine H1 Receptors Proteins 0.000 description 1
- 102000000543 Histamine Receptors Human genes 0.000 description 1
- 108010002059 Histamine Receptors Proteins 0.000 description 1
- DHUZAAUGHUHIDS-ONEGZZNKSA-N Isomyristicin Chemical compound COC1=CC(\C=C\C)=CC2=C1OCO2 DHUZAAUGHUHIDS-ONEGZZNKSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- SIKWOTFNWURSAY-UHFFFAOYSA-N Lipstatin Natural products CCCCCCC1C(CC(CC=CCC=CCCCCC)C(=O)OC(CC(C)C)NC=O)OC1=O SIKWOTFNWURSAY-UHFFFAOYSA-N 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000002467 anti-pepsin effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- JUCVMCNRABNRJD-UHFFFAOYSA-N azane;ethyl acetate Chemical compound N.CCOC(C)=O JUCVMCNRABNRJD-UHFFFAOYSA-N 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229960000530 carbenoxolone Drugs 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 208000030304 gastrointestinal bleeding Diseases 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229960004198 guanidine Drugs 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- NDEMNVPZDAFUKN-UHFFFAOYSA-N guanidine;nitric acid Chemical compound NC(N)=N.O[N+]([O-])=O.O[N+]([O-])=O NDEMNVPZDAFUKN-UHFFFAOYSA-N 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 239000013003 healing agent Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000938 histamine H1 antagonist Substances 0.000 description 1
- 229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- OQMAKWGYQLJJIA-CUOOPAIESA-N lipstatin Chemical compound CCCCCC[C@H]1[C@H](C[C@H](C\C=C/C\C=C/CCCCC)OC(=O)[C@H](CC(C)C)NC=O)OC1=O OQMAKWGYQLJJIA-CUOOPAIESA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 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
- QQHDLHUBMLOUGT-UHFFFAOYSA-N methyl N'-nitrosocarbamimidothioate Chemical compound CS\C(N)=N/N=O QQHDLHUBMLOUGT-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 229960005439 propantheline bromide Drugs 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000000580 secretagogue effect Effects 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
- 230000035882 stress Effects 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
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity 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
- ZCPSWAFANXCCOT-UHFFFAOYSA-N trichloromethanesulfonyl chloride Chemical compound ClC(Cl)(Cl)S(Cl)(=O)=O ZCPSWAFANXCCOT-UHFFFAOYSA-N 0.000 description 1
- RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Dental Preparations (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2173778 | 1978-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS207791B2 true CS207791B2 (en) | 1981-08-31 |
Family
ID=10167957
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS798890A CS207791B2 (en) | 1978-05-24 | 1979-05-22 | Method of making the derivatives of the thiadiazole |
| CS793518A CS207790B2 (en) | 1978-05-24 | 1979-05-22 | Method of making the derivatives of the thiadiazole |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS793518A CS207790B2 (en) | 1978-05-24 | 1979-05-22 | Method of making the derivatives of the thiadiazole |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4242350A (de) |
| EP (1) | EP0006679B1 (de) |
| JP (1) | JPS54160376A (de) |
| AT (1) | ATE1353T1 (de) |
| AU (1) | AU529253B2 (de) |
| CA (1) | CA1124729A (de) |
| CS (2) | CS207791B2 (de) |
| DD (1) | DD143772A5 (de) |
| DE (1) | DE2963363D1 (de) |
| DK (1) | DK209079A (de) |
| ES (3) | ES480894A1 (de) |
| FI (1) | FI791656A7 (de) |
| GR (1) | GR73611B (de) |
| HU (1) | HU179492B (de) |
| IE (1) | IE48221B1 (de) |
| IL (1) | IL57388A0 (de) |
| NO (1) | NO791710L (de) |
| NZ (1) | NZ190448A (de) |
| PL (1) | PL118387B1 (de) |
| PT (1) | PT69651A (de) |
| SU (1) | SU1037839A3 (de) |
| ZA (1) | ZA792202B (de) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE1353T1 (de) * | 1978-05-24 | 1982-08-15 | Imperial Chemical Industries Plc | Anti-sekretion thiadiazol-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
| EP0014057B1 (de) * | 1979-01-18 | 1985-01-02 | Imperial Chemical Industries Plc | Guanidin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| GR71929B (de) * | 1979-11-13 | 1983-08-19 | Ici Ltd | |
| US4375547A (en) * | 1980-10-02 | 1983-03-01 | Eli Lilly And Company | N-Methyl-N'-2-([(2-dimethylaminomethyl)-4-thiazolyl]methylthio)ethyl 2-nitro-1,1-ethenediamine |
| DE3270716D1 (en) * | 1981-02-27 | 1986-05-28 | Ici Plc | Guanidino-substituted heterocyclic derivatives having histamine h-2 antagonist activity |
| CA1209998A (en) * | 1981-03-09 | 1986-08-19 | David J. Gilman | Amide derivatives as histamine h-2 receptor antagonists |
| CA1233818A (en) * | 1981-03-09 | 1988-03-08 | David J. Gilman | Guanidine derivatives as histamine h-2 receptor antagonists |
| US4460584A (en) * | 1981-03-13 | 1984-07-17 | Imperial Chemical Industries Plc | Nitrogen heterocycles |
| IN158869B (de) * | 1981-03-18 | 1987-02-07 | Ici Plc | |
| US4463005A (en) * | 1981-03-18 | 1984-07-31 | Imperial Chemical Industries Plc | Bicyclic guanidines |
| US4451463A (en) * | 1981-03-24 | 1984-05-29 | Imperial Chemical Industries Plc | Alcohol derivatives |
| EP0065823A1 (de) * | 1981-05-13 | 1982-12-01 | Imperial Chemical Industries Plc | Heterozyklische Guanidinderivate als Histamin-H-2-Antagonisten |
| US4546188A (en) * | 1981-05-18 | 1985-10-08 | Bristol-Myers Company | Substituted 1,2-diaminocyclobutene-3,4-diones |
| US4395553A (en) * | 1981-05-18 | 1983-07-26 | Bristol-Myers Company | Chemical compounds |
| US4522943A (en) * | 1981-05-18 | 1985-06-11 | Bristol-Myers Company | Chemical compounds |
| US4526973A (en) * | 1981-05-18 | 1985-07-02 | Bristol-Myers Company | Chemical compounds |
| US4607105A (en) * | 1981-05-18 | 1986-08-19 | Bristol-Myers Company | 3-cyclobutene-1,2-dione intermediates |
| US4390701A (en) * | 1981-05-18 | 1983-06-28 | Bristol-Myers Company | 1-Amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione |
| US4539316A (en) * | 1981-05-18 | 1985-09-03 | Bristol-Myers Company | Pyridine derivatives of 1,2-diaminocyclobutene-3,4-diones |
| EP0067508B1 (de) * | 1981-05-18 | 1985-10-30 | Imperial Chemical Industries Plc | Amidin-Derivate |
| GB8419223D0 (en) * | 1984-07-27 | 1984-08-30 | Hoechst Uk Ltd | Sulphamoylguanidine derivatives |
| JPS60255756A (ja) * | 1984-06-01 | 1985-12-17 | Ikeda Mohandou:Kk | アミノアルキルフエノキシ誘導体 |
| RU2348623C1 (ru) * | 2007-05-21 | 2009-03-10 | Государственное образовательное учреждение высшего профессионального образования "Ивановский государственный химико-технологический университет" (ИГХТУ) | Способ получения 3,5-диамино-1,2,4-тиадиазола |
| 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 (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE842346C (de) * | 1950-10-14 | 1952-06-26 | Joachim Dipl-Chem Dr Goerdeler | Verfahren zur Darstellung von 5-Amino-1, 2, 4-thiodiazolen |
| DE955684C (de) * | 1953-10-14 | 1957-01-10 | Bayer Ag | Verfahren zur Herstellung von 5-Amino-1, 2, 4-thiodiazolen |
| NL266116A (de) | 1960-06-22 | |||
| BE758146A (fr) | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Derives de l'amidine |
| GB1305549A (de) | 1969-10-29 | 1973-02-07 | ||
| GB1338169A (en) | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| GB1400319A (en) | 1972-04-20 | 1975-07-16 | Smith Kline French Lab | Pharmaceutical compositions |
| GB1398426A (en) | 1972-09-05 | 1975-06-18 | Smith Kline French Lab | Heterocyclic substituted guanidines |
| GB1397436A (en) | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
| GB1421999A (en) | 1973-02-08 | 1976-01-21 | Smith Kline French Lab | Heterocyclic containing sulphoxides |
| GB1419994A (en) | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
| 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 |
| GB1497260A (en) | 1974-06-28 | 1978-01-05 | Smith Kline French Lab | Guanidine derivatives |
| GB1531231A (en) | 1974-09-02 | 1978-11-08 | Smith Kline French Lab | Process for the production of cyanoguanidine derivatives |
| GB1533379A (en) | 1974-09-02 | 1978-11-22 | Smith Kline French Lab | Process for the preparation of heterocyclic substituted ureas |
| GB1533380A (en) | 1974-09-02 | 1978-11-22 | Smith Kline French Lab | Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines |
| GB1574214A (en) | 1976-03-11 | 1980-09-03 | Smith Kline French Lab | Amidines |
| US4165378A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| IE47044B1 (en) * | 1977-04-20 | 1983-12-14 | Ici Ltd | Guanidine derivatives |
| ATE1353T1 (de) * | 1978-05-24 | 1982-08-15 | Imperial Chemical Industries Plc | Anti-sekretion thiadiazol-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
-
1979
- 1979-05-02 AT AT79300754T patent/ATE1353T1/de not_active IP Right Cessation
- 1979-05-02 DE DE7979300754T patent/DE2963363D1/de not_active Expired
- 1979-05-02 EP EP79300754A patent/EP0006679B1/de not_active Expired
- 1979-05-07 US US06/036,360 patent/US4242350A/en not_active Expired - Lifetime
- 1979-05-08 ZA ZA792202A patent/ZA792202B/xx unknown
- 1979-05-11 CA CA327,472A patent/CA1124729A/en not_active Expired
- 1979-05-14 NZ NZ190448A patent/NZ190448A/xx unknown
- 1979-05-16 AU AU47114/79A patent/AU529253B2/en not_active Ceased
- 1979-05-22 CS CS798890A patent/CS207791B2/cs unknown
- 1979-05-22 PT PT69651A patent/PT69651A/pt unknown
- 1979-05-22 DK DK209079A patent/DK209079A/da unknown
- 1979-05-22 HU HU79IE874A patent/HU179492B/hu unknown
- 1979-05-22 PL PL1979215764A patent/PL118387B1/pl unknown
- 1979-05-22 CS CS793518A patent/CS207790B2/cs unknown
- 1979-05-23 NO NO791710A patent/NO791710L/no unknown
- 1979-05-23 IL IL57388A patent/IL57388A0/xx unknown
- 1979-05-24 JP JP6330479A patent/JPS54160376A/ja active Pending
- 1979-05-24 FI FI791656A patent/FI791656A7/fi not_active Application Discontinuation
- 1979-05-24 SU SU792772852A patent/SU1037839A3/ru active
- 1979-05-24 ES ES480894A patent/ES480894A1/es not_active Expired
- 1979-05-24 DD DD79213131A patent/DD143772A5/de unknown
- 1979-08-08 IE IE902/79A patent/IE48221B1/en unknown
- 1979-09-13 ES ES484149A patent/ES484149A1/es not_active Expired
- 1979-09-13 ES ES484150A patent/ES484150A1/es not_active Expired
-
1980
- 1980-08-01 US US06/174,494 patent/US4332949A/en not_active Expired - Lifetime
-
1981
- 1981-01-27 GR GR59132A patent/GR73611B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ190448A (en) | 1980-12-19 |
| EP0006679A1 (de) | 1980-01-09 |
| JPS54160376A (en) | 1979-12-19 |
| FI791656A7 (fi) | 1981-01-01 |
| SU1037839A3 (ru) | 1983-08-23 |
| IL57388A0 (en) | 1979-09-30 |
| ES484149A1 (es) | 1980-04-16 |
| PL118387B1 (en) | 1981-09-30 |
| NO791710L (no) | 1979-11-27 |
| HU179492B (en) | 1982-10-28 |
| PT69651A (en) | 1979-06-01 |
| US4242350A (en) | 1980-12-30 |
| IE790902L (en) | 1979-11-24 |
| ATE1353T1 (de) | 1982-08-15 |
| CA1124729A (en) | 1982-06-01 |
| ES484150A1 (es) | 1980-04-16 |
| DD143772A5 (de) | 1980-09-10 |
| AU529253B2 (en) | 1983-06-02 |
| EP0006679B1 (de) | 1982-07-21 |
| CS207790B2 (en) | 1981-08-31 |
| AU4711479A (en) | 1979-11-29 |
| IE48221B1 (en) | 1984-10-31 |
| DK209079A (da) | 1979-11-25 |
| PL215764A1 (de) | 1980-06-16 |
| GR73611B (de) | 1984-03-26 |
| ZA792202B (en) | 1980-05-28 |
| DE2963363D1 (en) | 1982-09-09 |
| US4332949A (en) | 1982-06-01 |
| ES480894A1 (es) | 1980-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS207791B2 (en) | Method of making the derivatives of the thiadiazole | |
| EP0003640B1 (de) | Antisekretorische Guanidinderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate | |
| FI76795C (fi) | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 3,4-disubstituerade 1,2,5-tiadiazol-1-oxider och -1,1-dioxider samt nya mellanprodukter. | |
| PL113082B1 (en) | Method of guanidine derivatives preparation | |
| US3843668A (en) | Certain 4-substituted amino-2,1,3-benzothiadiozoles | |
| Anglada et al. | Inhibitors of gastric acid secretion: N-sulphonyl formamidines in a series of new histamine H2-receptor antagonists | |
| NZ206614A (en) | Dihydropyridine derivatives and pharmaceutical compositions | |
| US4242351A (en) | Antisecretory oxadiazoles and pharmaceutical compositions containing them | |
| US4440933A (en) | Process for preparing 1,2,5-thiadiazoles | |
| US4891375A (en) | Arylpiperazinyl-alkylene-phenyl-heterocyclic compounds | |
| EP0649843B1 (de) | Thiazolin-derivate | |
| KR870000912B1 (ko) | 디하이드로피리딘 유도체의 제조방법 | |
| EP0010893A1 (de) | Verzweigtkettige heterozyklische Guanidinderivate mit antisekretorischer Wirkung, Verfahren zu ihrer Herstellung, Zwischenprodukte und die genannten Derivate enthaltende pharmazeutische Zusammensetzungen | |
| US4338447A (en) | 5-Guanidino-1,2,4-oxadiazoles | |
| US4649145A (en) | Thiazole derivatives | |
| US3299082A (en) | Chemical compounds and processes for preparing same | |
| EP0117345B1 (de) | Aminopyrimidinone als Histamin-H2-Antagonisten | |
| SE410460B (sv) | Forfarande for framstellning av imidazoforeningar | |
| US4178451A (en) | 3-(Substituted hydrazino)benzisothiazole-1,1-dioxides | |
| CS197238B2 (en) | Method of producing novel acylated derivatives of 2-amino thiazole | |
| CS250229B2 (en) | Method of 3,4-diamino-1,2,5-thiadiazole derivatives' production | |
| CA2040011C (en) | Thiazole and imidazole derivatives and antiulcer composition containing same | |
| EP0074229A1 (de) | Triazole mit Magensäuresekretionhemmwirkung | |
| EP0030835B1 (de) | 2-Substituierte-6-phenyl-3(2H)-pyridazinon-Derivate, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen | |
| IE54284B1 (en) | Benzo-fused heterocyclic compounds |