NO791710L - Analogifremgangsmaate for fremstilling av fysiologisk aktive tiadiazolderivater - Google Patents
Analogifremgangsmaate for fremstilling av fysiologisk aktive tiadiazolderivaterInfo
- Publication number
- NO791710L NO791710L NO791710A NO791710A NO791710L NO 791710 L NO791710 L NO 791710L NO 791710 A NO791710 A NO 791710A NO 791710 A NO791710 A NO 791710A NO 791710 L NO791710 L NO 791710L
- Authority
- NO
- Norway
- Prior art keywords
- radical
- formula
- sub
- thiadiazole
- guanidino
- Prior art date
Links
- 150000004867 thiadiazoles Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 13
- -1 3,4-dioxocyclobuten-1,2-diyl Chemical group 0.000 claims abstract description 53
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 57
- 150000003254 radicals Chemical class 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 239000007858 starting material Substances 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 5
- 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 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 2
- KYAGLVMWSUGNOE-UHFFFAOYSA-N 1-cyano-2-[2-[[5-(diaminomethylideneamino)-1,2,4-thiadiazol-3-yl]methylsulfanyl]ethyl]guanidine Chemical compound NC(=N)NC1=NC(CSCCNC(N)=NC#N)=NS1 KYAGLVMWSUGNOE-UHFFFAOYSA-N 0.000 claims description 2
- JYMTYOJMMWEJEN-UHFFFAOYSA-N 2-(2-aminoethyl)-1-cyano-3-[2-[[5-(diaminomethylideneamino)-1,2,4-thiadiazol-3-yl]methylsulfanyl]ethyl]guanidine Chemical compound NCCNC(=NC#N)NCCSCC1=NSC(NC(N)=N)=N1 JYMTYOJMMWEJEN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 239000005864 Sulphur Substances 0.000 claims 8
- CAMRHYBKQTWSCM-UHFFFAOYSA-N oxocyanamide Chemical compound O=NC#N CAMRHYBKQTWSCM-UHFFFAOYSA-N 0.000 claims 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 161
- 239000000243 solution Substances 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 20
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 229960001340 histamine Drugs 0.000 description 13
- 239000003085 diluting agent Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 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 10
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 210000004211 gastric acid Anatomy 0.000 description 7
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 230000028327 secretion Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 206010016717 Fistula Diseases 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
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000002269 analeptic agent Substances 0.000 description 4
- 229960001380 cimetidine Drugs 0.000 description 4
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 4
- 230000003890 fistula Effects 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 3
- 208000008469 Peptic Ulcer Diseases 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000005764 inhibitory process Effects 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
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- 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 3
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 230000007306 turnover Effects 0.000 description 3
- 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 2
- 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 2
- MIXKAOJEIDZGRH-UHFFFAOYSA-N 2-[3-[2-[[1-(methylamino)-2-nitroethenyl]amino]ethylsulfanylmethyl]-1,2,4-thiadiazol-5-yl]guanidine Chemical group [O-][N+](=O)C=C(NC)NCCSCC1=NSC(N=C(N)N)=N1 MIXKAOJEIDZGRH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010065713 Gastric Fistula Diseases 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 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
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- 108010079943 Pentagastrin Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940125715 antihistaminic agent Drugs 0.000 description 2
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- ZOKYZTUQSVAKHS-UHFFFAOYSA-N dimethoxymethylidenecyanamide Chemical compound COC(OC)=NC#N ZOKYZTUQSVAKHS-UHFFFAOYSA-N 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
- 229960000520 diphenhydramine Drugs 0.000 description 2
- 239000000938 histamine H1 antagonist Substances 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 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 2
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
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- VJLYHTOSFSGXGH-CQSZACIVSA-N (2R)-1-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]pyrrolidine-2-carboxylic acid Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2[C@H](CCC2)C(=O)O)C=CC=1 VJLYHTOSFSGXGH-CQSZACIVSA-N 0.000 description 1
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- 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
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- 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
- JQCAWQXVACQOCO-UHFFFAOYSA-N 1-cyano-3-[2-[[5-(diaminomethylideneamino)-1,2,4-thiadiazol-3-yl]methylsulfinyl]ethyl]-2-methylguanidine Chemical compound N#CNC(=NC)NCCS(=O)CC1=NSC(N=C(N)N)=N1 JQCAWQXVACQOCO-UHFFFAOYSA-N 0.000 description 1
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- DRBQEWXWLOSALI-UHFFFAOYSA-N 2-[3-[2-[(1-methylsulfanyl-2-nitroethenyl)amino]ethylsulfanylmethyl]-1,2,4-thiadiazol-5-yl]guanidine Chemical group [O-][N+](=O)C=C(SC)NCCSCC1=NSC(N=C(N)N)=N1 DRBQEWXWLOSALI-UHFFFAOYSA-N 0.000 description 1
- MSTPFNIKZYIGLR-UHFFFAOYSA-N 2-[3-[2-[(2-methoxy-3,4-dioxocyclobuten-1-yl)amino]ethylsulfanylmethyl]-1,2,4-thiadiazol-5-yl]guanidine Chemical compound O=C1C(=O)C(OC)=C1NCCSCC1=NSC(NC(N)=N)=N1 MSTPFNIKZYIGLR-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
- NJAHGEUFOYIGKR-UHFFFAOYSA-N 2-chloroethanimidamide Chemical compound NC(=N)CCl NJAHGEUFOYIGKR-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 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
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- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 1
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- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- SJNUMMFBKJIFOX-UHFFFAOYSA-N methyl N-cyano-N'-[3-[[5-(diaminomethylideneamino)-1,2,4-thiadiazol-3-yl]methylsulfanyl]propyl]carbamimidothioate Chemical compound C(#N)N=C(NCCCSCC1=NSC(=N1)NC(=N)N)SC SJNUMMFBKJIFOX-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- FLZZNZJENFNFOJ-UHFFFAOYSA-N methyl n'-nitrocarbamimidothioate Chemical compound CSC(N)=N[N+]([O-])=O FLZZNZJENFNFOJ-UHFFFAOYSA-N 0.000 description 1
- HCBPHBQMSDVIPZ-UHFFFAOYSA-N methylcyclohexatriene Chemical compound CC1=CC=C=C[CH]1 HCBPHBQMSDVIPZ-UHFFFAOYSA-N 0.000 description 1
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- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229950000964 pepstatin Drugs 0.000 description 1
- 108010091212 pepstatin Proteins 0.000 description 1
- FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-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
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000012746 preparative thin layer 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000002002 slurry Substances 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
- 159000000000 sodium salts Chemical class 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
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
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- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 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
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000003357 wound healing promoting agent Substances 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)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2173778 | 1978-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO791710L true NO791710L (no) | 1979-11-27 |
Family
ID=10167957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO791710A NO791710L (no) | 1978-05-24 | 1979-05-23 | Analogifremgangsmaate for fremstilling av fysiologisk aktive tiadiazolderivater |
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) | CS207790B2 (de) |
| DD (1) | DD143772A5 (de) |
| DE (1) | DE2963363D1 (de) |
| DK (1) | DK209079A (de) |
| ES (3) | ES480894A1 (de) |
| FI (1) | FI791656A (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 (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006679B1 (de) * | 1978-05-24 | 1982-07-21 | Imperial Chemical Industries Plc | Anti-Sekretion Thiadiazol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
| DE3069889D1 (en) * | 1979-01-18 | 1985-02-14 | Ici Plc | Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| 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 |
| CA1233818A (en) * | 1981-03-09 | 1988-03-08 | David J. Gilman | Guanidine derivatives as histamine h-2 receptor antagonists |
| CA1209998A (en) * | 1981-03-09 | 1986-08-19 | David J. Gilman | Amide 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 |
| US4539316A (en) * | 1981-05-18 | 1985-09-03 | Bristol-Myers Company | Pyridine derivatives of 1,2-diaminocyclobutene-3,4-diones |
| US4526973A (en) * | 1981-05-18 | 1985-07-02 | Bristol-Myers Company | Chemical compounds |
| US4522943A (en) * | 1981-05-18 | 1985-06-11 | Bristol-Myers Company | Chemical compounds |
| US4390701A (en) * | 1981-05-18 | 1983-06-28 | Bristol-Myers Company | 1-Amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione |
| DE3267110D1 (de) * | 1981-05-18 | 1985-12-05 | Ici Plc | Amidine derivatives |
| US4607105A (en) * | 1981-05-18 | 1986-08-19 | Bristol-Myers Company | 3-cyclobutene-1,2-dione intermediates |
| 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 |
| 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 |
| EP4196793A1 (de) | 2020-08-11 | 2023-06-21 | Université de Strasbourg | Auf lebermakrophagen abzielende h2-blocker zur prävention und behandlung von lebererkrankungen und krebs |
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 | |||
| GB1305549A (de) | 1969-10-29 | 1973-02-07 | ||
| BE758146A (fr) | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Derives de l'amidine |
| GB1338169A (en) | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| GB1400319A (en) | 1972-04-20 | 1975-07-16 | Smith Kline French Lab | Pharmaceutical compositions |
| GB1397436A (en) | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
| GB1398426A (en) | 1972-09-05 | 1975-06-18 | Smith Kline French Lab | Heterocyclic substituted guanidines |
| 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 |
| GB1533380A (en) | 1974-09-02 | 1978-11-22 | Smith Kline French Lab | Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines |
| 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 |
| GB1574214A (en) | 1976-03-11 | 1980-09-03 | Smith Kline French Lab | Amidines |
| IE47044B1 (en) * | 1977-04-20 | 1983-12-14 | Ici Ltd | Guanidine derivatives |
| US4165378A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| EP0006679B1 (de) * | 1978-05-24 | 1982-07-21 | Imperial Chemical Industries Plc | Anti-Sekretion Thiadiazol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
-
1979
- 1979-05-02 EP EP79300754A patent/EP0006679B1/de not_active Expired
- 1979-05-02 AT AT79300754T patent/ATE1353T1/de not_active IP Right Cessation
- 1979-05-02 DE DE7979300754T patent/DE2963363D1/de not_active Expired
- 1979-05-07 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 PT PT69651A patent/PT69651A/pt unknown
- 1979-05-22 PL PL1979215764A patent/PL118387B1/pl unknown
- 1979-05-22 HU HU79IE874A patent/HU179492B/hu unknown
- 1979-05-22 DK DK209079A patent/DK209079A/da unknown
- 1979-05-22 CS CS793518A patent/CS207790B2/cs unknown
- 1979-05-22 CS CS798890A patent/CS207791B2/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/FI791656A/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 ES484150A patent/ES484150A1/es not_active Expired
- 1979-09-13 ES ES484149A patent/ES484149A1/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 |
|---|---|
| IE48221B1 (en) | 1984-10-31 |
| PT69651A (en) | 1979-06-01 |
| ES484150A1 (es) | 1980-04-16 |
| US4332949A (en) | 1982-06-01 |
| EP0006679B1 (de) | 1982-07-21 |
| GR73611B (de) | 1984-03-26 |
| ZA792202B (en) | 1980-05-28 |
| NZ190448A (en) | 1980-12-19 |
| ES484149A1 (es) | 1980-04-16 |
| DK209079A (da) | 1979-11-25 |
| AU4711479A (en) | 1979-11-29 |
| IE790902L (en) | 1979-11-24 |
| EP0006679A1 (de) | 1980-01-09 |
| DD143772A5 (de) | 1980-09-10 |
| JPS54160376A (en) | 1979-12-19 |
| CS207791B2 (en) | 1981-08-31 |
| HU179492B (en) | 1982-10-28 |
| AU529253B2 (en) | 1983-06-02 |
| PL215764A1 (de) | 1980-06-16 |
| US4242350A (en) | 1980-12-30 |
| PL118387B1 (en) | 1981-09-30 |
| ES480894A1 (es) | 1980-02-01 |
| FI791656A (fi) | 1979-11-25 |
| SU1037839A3 (ru) | 1983-08-23 |
| DE2963363D1 (en) | 1982-09-09 |
| CS207790B2 (en) | 1981-08-31 |
| IL57388A0 (en) | 1979-09-30 |
| ATE1353T1 (de) | 1982-08-15 |
| CA1124729A (en) | 1982-06-01 |
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