CY1360A - 3,4-disubstituted-1,2,5-thiadiazole-1-oxides and 1,1 dioxides - Google Patents
3,4-disubstituted-1,2,5-thiadiazole-1-oxides and 1,1 dioxides Download PDFInfo
- Publication number
- CY1360A CY1360A CY136080A CY136080A CY1360A CY 1360 A CY1360 A CY 1360A CY 136080 A CY136080 A CY 136080A CY 136080 A CY136080 A CY 136080A CY 1360 A CY1360 A CY 1360A
- Authority
- CY
- Cyprus
- Prior art keywords
- alkyl
- compound
- thiadiazole
- amino
- phenyl
- Prior art date
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- -1 3,4-disubstituted-1,2,5-thiadiazole-1-oxides Chemical class 0.000 title claims description 193
- 150000001875 compounds Chemical class 0.000 claims description 271
- 125000000217 alkyl group Chemical group 0.000 claims description 255
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 116
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 91
- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- 125000003545 alkoxy group Chemical group 0.000 claims description 72
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 70
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 69
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 49
- 125000003282 alkyl amino group Chemical group 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 43
- 125000003342 alkenyl group Chemical group 0.000 claims description 42
- 125000000304 alkynyl group Chemical group 0.000 claims description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 239000011593 sulfur Substances 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 231100000252 nontoxic Toxicity 0.000 claims description 23
- 230000003000 nontoxic effect Effects 0.000 claims description 23
- CDHKCMVEGUQUCN-UHFFFAOYSA-N 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide Chemical compound COC1=NS(=O)N=C1OC CDHKCMVEGUQUCN-UHFFFAOYSA-N 0.000 claims description 22
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 22
- 150000001204 N-oxides Chemical class 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 22
- 239000001301 oxygen Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000000335 thiazolyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000002541 furyl group Chemical group 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 16
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 14
- 239000005977 Ethylene Substances 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 230000002496 gastric effect Effects 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical group S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 230000028327 secretion Effects 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 239000003699 antiulcer agent Substances 0.000 claims description 3
- 125000006308 propyl amino group Chemical group 0.000 claims description 3
- VLKCIRAOEMFIRG-UHFFFAOYSA-N 4-n-methyl-1,1-dioxo-3-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound CNC1=NS(=O)(=O)N=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 VLKCIRAOEMFIRG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 4
- 239000005864 Sulphur Substances 0.000 claims 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- WIJIXDONFDMDEY-UHFFFAOYSA-N 1,1-dioxo-1,2,5-thiadiazol-3-amine Chemical compound NC1=NS(=O)(=O)N=C1 WIJIXDONFDMDEY-UHFFFAOYSA-N 0.000 claims 1
- DUPAVAVETJQPOR-UHFFFAOYSA-N 1-oxo-3-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound NC1=NS(=O)N=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 DUPAVAVETJQPOR-UHFFFAOYSA-N 0.000 claims 1
- MWQSYHLKUCRDMA-UHFFFAOYSA-N O.NC1=NS(N=C1NCCSCC=1N=C(SC1)NC(=N)N)=O Chemical group O.NC1=NS(N=C1NCCSCC=1N=C(SC1)NC(=N)N)=O MWQSYHLKUCRDMA-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 102220254284 rs755928199 Human genes 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 528
- 239000000243 solution Substances 0.000 description 218
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 98
- 239000000047 product Substances 0.000 description 91
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 239000011541 reaction mixture Substances 0.000 description 81
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 80
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 61
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 59
- 239000000741 silica gel Substances 0.000 description 54
- 229910002027 silica gel Inorganic materials 0.000 description 54
- 238000001953 recrystallisation Methods 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 52
- 238000003756 stirring Methods 0.000 description 52
- 239000000725 suspension Substances 0.000 description 49
- 238000010828 elution Methods 0.000 description 45
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 43
- 239000005457 ice water Substances 0.000 description 42
- ZRSLQBDTGLCFJJ-UHFFFAOYSA-N 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide Chemical compound COC1=NS(=O)(=O)N=C1OC ZRSLQBDTGLCFJJ-UHFFFAOYSA-N 0.000 description 40
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 40
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 33
- 238000007920 subcutaneous administration Methods 0.000 description 29
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 17
- 238000010992 reflux Methods 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 9
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Substances OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- LKHDXIBHVSGUHN-UHFFFAOYSA-N thiadiazole 1,1-dioxide Chemical compound O=S1(=O)C=CN=N1 LKHDXIBHVSGUHN-UHFFFAOYSA-N 0.000 description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 8
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- 238000010438 heat treatment Methods 0.000 description 8
- 238000007912 intraperitoneal administration Methods 0.000 description 8
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 8
- JGUPTNIZOBZUON-UHFFFAOYSA-N 3,4-dimethoxy-1,2,5-thiadiazole Chemical compound COC1=NSN=C1OC JGUPTNIZOBZUON-UHFFFAOYSA-N 0.000 description 7
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- JFINSZHXZPNADJ-UHFFFAOYSA-N 2-[4-(2-aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine Chemical compound NCCSCC1=CSC(NC(N)=N)=N1 JFINSZHXZPNADJ-UHFFFAOYSA-N 0.000 description 5
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- VQSXCZMVUMSITD-UHFFFAOYSA-N 3-[3-(piperidin-1-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCC2)=C1 VQSXCZMVUMSITD-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
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- 101150041968 CDC13 gene Proteins 0.000 description 1
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- 241000700199 Cavia porcellus Species 0.000 description 1
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- BQRQOLQFLNSWNV-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanol Chemical compound CN(C)CC1=CC=C(CO)O1 BQRQOLQFLNSWNV-UHFFFAOYSA-N 0.000 description 1
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- IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 1
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- XIDIMHCCDGNIFC-UHFFFAOYSA-N methyl 6-(dimethylcarbamoyl)pyridine-2-carboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)N(C)C)=N1 XIDIMHCCDGNIFC-UHFFFAOYSA-N 0.000 description 1
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- LFKURYSUUKOZSA-UHFFFAOYSA-N n-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-4-methoxy-1,1-dioxo-1,2,5-thiadiazol-3-amine Chemical compound COC1=NS(=O)(=O)N=C1NCCSCC1=CSC(CN(C)C)=N1 LFKURYSUUKOZSA-UHFFFAOYSA-N 0.000 description 1
- SCOSHPGDHNWCHZ-UHFFFAOYSA-N n-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-4-methoxy-1-oxo-1,2,5-thiadiazol-3-amine Chemical compound COC1=NS(=O)N=C1NCCSCC1=CSC(CN(C)C)=N1 SCOSHPGDHNWCHZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- NBQBFLMRWBFEJF-UHFFFAOYSA-N phenyl n-[[4-(2-aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]methyl]-n-methylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)N(C)CC1=NC(CSCCN)=CS1 NBQBFLMRWBFEJF-UHFFFAOYSA-N 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
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- 230000000717 retained effect Effects 0.000 description 1
- 238000003385 ring cleavage reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 102220106802 rs139353014 Human genes 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
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- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Lubricants (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7251779A | 1979-09-04 | 1979-09-04 | |
| US11718280A | 1980-01-31 | 1980-01-31 | |
| US16383180A | 1980-06-07 | 1980-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1360A true CY1360A (en) | 1987-08-07 |
Family
ID=27372107
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY136080A CY1360A (en) | 1979-09-04 | 1980-09-02 | 3,4-disubstituted-1,2,5-thiadiazole-1-oxides and 1,1 dioxides |
| CY140283A CY1402A (en) | 1979-09-04 | 1983-07-13 | Thiadazole oxides and dioxides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY140283A CY1402A (en) | 1979-09-04 | 1983-07-13 | Thiadazole oxides and dioxides |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4374248A (cs) |
| AR (1) | AR240559A1 (cs) |
| AT (2) | AT376978B (cs) |
| CA (4) | CA1167841A (cs) |
| CH (2) | CH649764A5 (cs) |
| CS (1) | CS235951B2 (cs) |
| CY (2) | CY1360A (cs) |
| DE (2) | DE3051146C2 (cs) |
| DK (4) | DK160611C (cs) |
| FI (1) | FI76795C (cs) |
| GB (2) | GB2067987B (cs) |
| HK (2) | HK41387A (cs) |
| IE (2) | IE51235B1 (cs) |
| KE (2) | KE3685A (cs) |
| LU (1) | LU82753A1 (cs) |
| MY (2) | MY8700735A (cs) |
| NL (3) | NL189197C (cs) |
| NO (4) | NO160003C (cs) |
| NZ (1) | NZ194831A (cs) |
| PT (1) | PT71764B (cs) |
| SE (5) | SE449099B (cs) |
| SG (1) | SG61187G (cs) |
| ZW (1) | ZW20580A1 (cs) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3175201D1 (en) * | 1980-04-30 | 1986-10-02 | Merck & Co Inc | Aminothiadiazoles as gastric secretion inhibitors |
| US4760075A (en) * | 1980-10-02 | 1988-07-26 | Eli Lilly And Company | N-thiazolylmethylthioalkyl-N-alkyl-amidines and related compounds |
| US4904792A (en) * | 1980-10-02 | 1990-02-27 | Eli Lilly And Company | N-thiazolymethylthioalkyl-N'-alkylamidines and related compounds |
| US4471122A (en) * | 1981-03-03 | 1984-09-11 | Bristol-Myers Company | Thiadiazole histamine H2 -antagonists |
| US4362726A (en) | 1981-04-24 | 1982-12-07 | Merck & Co., Inc. | Substituted-1,2,5-thiadiazole-1-oxide compounds, compositions and use |
| EP0065823A1 (en) * | 1981-05-13 | 1982-12-01 | Imperial Chemical Industries Plc | Heterocyclic guanidines as histamine H-2 antagonists |
| IE53068B1 (en) * | 1981-06-15 | 1988-05-25 | Merck & Co Inc | Diamino isothiazole-1-oxides and -1,1-dioxides as gastic secretion inhibitors |
| EP0073971B1 (en) * | 1981-08-24 | 1986-05-21 | Merck & Co. Inc. | Thiadiazole oxides as gastric antisecretory agents |
| GR77847B (cs) * | 1981-12-14 | 1984-09-25 | American Home Prod | |
| US4578471A (en) * | 1982-03-29 | 1986-03-25 | Bristol-Myers Company | Substituted amino alkyl pyridyl ethanediimidamides |
| US4528377A (en) * | 1982-03-29 | 1985-07-09 | Bristol-Myers Company | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity |
| US4517366A (en) * | 1982-03-29 | 1985-05-14 | Bristol-Myers Company | Intermediates for preparing 3,4-diamino-1,2,5-thiadiazoles |
| ZA832154B (en) * | 1982-03-29 | 1983-12-28 | Bristol Myers Co | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine h2-receptor antagonist activity |
| US4528375A (en) * | 1982-03-29 | 1985-07-09 | Bristol-Myers Company | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity |
| US4528378A (en) * | 1982-03-29 | 1985-07-09 | Bristol-Myers Company | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity |
| FI832519A7 (fi) * | 1982-07-12 | 1984-01-13 | Bristol Myers Co | Farmaseuttisia menetelmiä ja koostumuksia. |
| US4520025A (en) * | 1982-07-21 | 1985-05-28 | William H. Rorer, Inc. | Bicyclic nitrogen heterocyclic ethers and thioethers, and their pharmaceutical uses |
| EP0105732A3 (en) * | 1982-10-01 | 1985-09-04 | Beecham Group Plc | Histamine h2 receptor antagonists of the benzisothiazole amino and benzthiadiazine amino series |
| US4461900A (en) * | 1983-03-14 | 1984-07-24 | American Home Products Corporation | 4,5-Dihydrothiadiazole 1,1-dioxide derivatives |
| US4440933A (en) * | 1983-03-16 | 1984-04-03 | Bristol-Myers Company | Process for preparing 1,2,5-thiadiazoles |
| AT387384B (de) * | 1983-03-16 | 1989-01-10 | Bristol Myers Co | Verfahren zur herstellung von thiadiazolderivaten |
| AU563072B2 (en) * | 1983-04-26 | 1987-06-25 | Shionogi & Co., Ltd. | 2-guanidino-4-hydroxymethylthiazole and derivitives thereof |
| US4543352A (en) * | 1983-04-29 | 1985-09-24 | William H. Rorer, Inc. | Naphthalene aminoalkylene ethers and thioethers, and their pharmaceutical uses |
| DE3326545A1 (de) * | 1983-07-22 | 1985-01-31 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Propan-2-ol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4529731A (en) * | 1983-09-22 | 1985-07-16 | American Home Products Corporation | Thiadiazolediamine derivative with histamine H-2 receptor inhibiting properties |
| US4692531A (en) * | 1984-06-22 | 1987-09-08 | Bristol-Myers Company | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity |
| US4644006A (en) * | 1984-06-22 | 1987-02-17 | Bristol-Myers Company | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity |
| US4612309A (en) * | 1984-10-23 | 1986-09-16 | William H. Rorer, Inc. | Antisecretory bicyclic benzo-oxy heterocyclic ethers and thioethers |
| GB8501535D0 (en) * | 1985-01-22 | 1985-02-20 | Smith Kline French Lab | Chemical compounds |
| US4728648A (en) * | 1985-02-09 | 1988-03-01 | Smith Kline & French Laboratories Limited | Histamine antagonist triadiazole derivatives, compositions, and method of use therefor |
| GB8509276D0 (en) * | 1985-04-11 | 1985-05-15 | Smith Kline French Lab | Pyridine derivatives |
| GB8510680D0 (en) * | 1985-04-26 | 1985-06-05 | Smith Kline French Lab | Pyridine derivatives |
| CA1286297C (en) * | 1985-06-13 | 1991-07-16 | George S. Sach | Pyridine derivatives |
| DE3532880A1 (de) * | 1985-09-14 | 1987-03-26 | Basf Ag | 1,4-disubstituierte pyrazolderivate |
| GB8610867D0 (en) * | 1986-05-02 | 1986-06-11 | Smith Kline French Lab | 3-hydroxypyridines |
| ES2008962A6 (es) * | 1987-12-17 | 1989-08-16 | Marga Investigacion | Proceso para la preparacion de nuevos compuestos de 2-guanidinotiazol |
| IL101915A (en) * | 1991-05-21 | 1996-12-05 | Lilly Co Eli | Process for the preparation of nizididine intermediates and related compounds |
| US5248673A (en) * | 1992-12-23 | 1993-09-28 | Bristol-Myers Squibb Co. | Bisamidine derivatives as thrombin inhibitors |
| US5821371A (en) * | 1994-10-24 | 1998-10-13 | Eli Lilly And Comany | Heterocyclic compounds and their preparation and use |
| US5618816A (en) * | 1995-03-02 | 1997-04-08 | Bristol-Myers Squibb Company | Antimigraine 1,2,5-thiadiazole derivatives of indolylalkyl-pyridnyl and pyrimidinylpiperazines |
| US5767280A (en) * | 1995-06-01 | 1998-06-16 | Eli Lilly And Company | Process for making heterocyclic compounds |
| EP1551818B1 (en) | 2002-10-09 | 2009-02-04 | Schering Corporation | Thiadiazoledioxides and thiadiazoleoxides as cxc- and cc-chemokine receptor ligands |
| DE602004016211D1 (en) | 2003-12-19 | 2008-10-09 | Schering Corp | Thiadiazole als cxc- und cc-chemokinrezeptorliganden |
| WO2005068460A1 (en) | 2003-12-22 | 2005-07-28 | Schering Corporation | Isothiazole dioxides as cxc- and cc- chemokine receptor ligands |
| DE602006017849D1 (de) | 2005-06-29 | 2010-12-09 | Schering Corp | 5,6-disubstituierte oxadiazolopyrazine und thiadiazolopyrazine als liganden des cxc-chemokinrezeptors |
| US7718678B2 (en) | 2005-06-29 | 2010-05-18 | Schering Corporation | Di-substituted oxadiazoles as CXC-chemokine receptor ligands |
| WO2013134562A1 (en) | 2012-03-09 | 2013-09-12 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| WO2014009293A1 (en) | 2012-07-13 | 2014-01-16 | Basf Se | New substituted thiadiazoles and their use as fungicides |
| JP6404230B2 (ja) | 2012-12-20 | 2018-10-10 | インセプション 2、 インコーポレイテッド | トリアゾロン化合物およびその使用 |
| EA201690230A1 (ru) | 2013-09-06 | 2016-07-29 | Инсепшн 2, Инк. | Соединения триазолона и их применения |
| CN105061360B (zh) * | 2015-07-28 | 2018-06-19 | 首都师范大学 | 一种3,4-二氨基-1,2,5-噻二唑的提纯方法 |
| 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 (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL22850A (en) * | 1964-03-18 | 1968-12-26 | Merck & Co Inc | 3-chloro-1,2,5-thiazdiazole-4-carboxylic acid being an intermediate in the preparation of sulfa drugs |
| CH482712A (de) * | 1964-10-01 | 1969-12-15 | Merck & Co Inc | Verfahren zur Herstellung von 3-Amino-1,2,5-thiadiazolen |
| US3564000A (en) * | 1965-10-15 | 1971-02-16 | Merck & Co Inc | Process for preparing 3-chloro-4-hydroxy-1,2,5-thiadiazole derivatives |
| US3419573A (en) * | 1965-10-15 | 1968-12-31 | Merck & Co Inc | 3-chloro-4-oxy-1,2,5-thiadiazoles, and a process for preparing same |
| DE1770152A1 (de) * | 1968-04-08 | 1971-09-30 | Lentia Gmbh | Verfahren zur Herstellung von 3-Amino-4-brom-1,2,5-thiadiazol |
| US3657237A (en) * | 1968-05-22 | 1972-04-18 | Frosst & Co Charles E | Process for making 1 2 5-thiadiazoles in the sinister configuration |
| US4104381A (en) * | 1973-05-03 | 1978-08-01 | Smith Kline & French Laboratories Limited | Pharmacologically active compounds |
| AT348517B (de) * | 1977-01-19 | 1979-02-26 | Chemie Linz Ag | Verfahren zur herstellung von reinem 3-methoxy- 4- (4'-aminobenzolsulfonamido) -1,2,5-thiadiazol |
| ZA782129B (en) * | 1977-04-20 | 1979-03-28 | Ici Ltd | Hertocyclic derivatives |
| US4165378A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| US4374836A (en) * | 1978-10-16 | 1983-02-22 | Imperial Chemical Industries Ltd. | Antisecretory heterocyclic derivatives, process for their manufacture and pharmaceutical compositions containing them |
| DE3175201D1 (en) * | 1980-04-30 | 1986-10-02 | Merck & Co Inc | Aminothiadiazoles as gastric secretion inhibitors |
| EP0045155B1 (en) * | 1980-07-30 | 1985-01-02 | Imperial Chemical Industries Plc | Guanidine derivatives |
| EP0073971B1 (en) * | 1981-08-24 | 1986-05-21 | Merck & Co. Inc. | Thiadiazole oxides as gastric antisecretory agents |
-
1980
- 1980-09-01 DK DK371880A patent/DK160611C/da not_active IP Right Cessation
- 1980-09-01 NL NLAANVRAGE8004967,A patent/NL189197C/xx not_active IP Right Cessation
- 1980-09-01 FI FI802740A patent/FI76795C/fi not_active IP Right Cessation
- 1980-09-02 NO NO80802576A patent/NO160003C/no unknown
- 1980-09-02 CY CY136080A patent/CY1360A/en unknown
- 1980-09-02 GB GB8028326A patent/GB2067987B/en not_active Expired
- 1980-09-03 DE DE3051146A patent/DE3051146C2/de not_active Expired - Fee Related
- 1980-09-03 IE IE1175/86A patent/IE51235B1/en not_active IP Right Cessation
- 1980-09-03 CA CA000359493A patent/CA1167841A/en not_active Expired
- 1980-09-03 IE IE1851/80A patent/IE50997B1/en not_active IP Right Cessation
- 1980-09-03 NZ NZ194831A patent/NZ194831A/en unknown
- 1980-09-03 AT AT0443480A patent/AT376978B/de active
- 1980-09-03 DE DE3033169A patent/DE3033169C2/de not_active Expired
- 1980-09-03 PT PT71764A patent/PT71764B/pt not_active IP Right Cessation
- 1980-09-03 SE SE8006148A patent/SE449099B/sv not_active IP Right Cessation
- 1980-09-04 CH CH6659/80A patent/CH649764A5/de not_active IP Right Cessation
- 1980-09-04 CH CH1760/85A patent/CH658055A5/de not_active IP Right Cessation
- 1980-09-04 ZW ZW205/80A patent/ZW20580A1/xx unknown
- 1980-09-04 CS CS816979A patent/CS235951B2/cs unknown
- 1980-09-04 LU LU82753A patent/LU82753A1/fr unknown
-
1981
- 1981-06-23 US US06/276,586 patent/US4374248A/en not_active Expired - Lifetime
-
1982
- 1982-11-02 CA CA000431960A patent/CA1248962A/en not_active Expired
- 1982-11-02 CA CA000579080A patent/CA1263115A/en not_active Expired
- 1982-11-02 CA CA000579079A patent/CA1263114A/en not_active Expired
-
1983
- 1983-07-13 GB GB08318949A patent/GB2132190B/en not_active Expired
- 1983-07-13 CY CY140283A patent/CY1402A/en unknown
- 1983-11-29 AR AR29495183A patent/AR240559A1/es active
-
1984
- 1984-02-27 AT AT0064584A patent/AT377257B/de not_active IP Right Cessation
- 1984-06-08 SE SE8403107A patent/SE456580B/sv not_active IP Right Cessation
- 1984-06-08 SE SE8403109A patent/SE456581B/sv not_active IP Right Cessation
- 1984-06-08 SE SE8403108A patent/SE456582B/sv not_active IP Right Cessation
- 1984-06-08 SE SE8403111A patent/SE461733B/sv not_active IP Right Cessation
-
1986
- 1986-06-23 NO NO86862501A patent/NO162664C/no unknown
- 1986-12-23 KE KE3685A patent/KE3685A/xx unknown
-
1987
- 1987-04-06 NO NO87871420A patent/NO161737C/no unknown
- 1987-04-06 NO NO87871421A patent/NO160781C/no unknown
- 1987-05-28 HK HK413/87A patent/HK41387A/xx unknown
- 1987-07-20 KE KE3742A patent/KE3742A/xx unknown
- 1987-07-28 SG SG611/87A patent/SG61187G/en unknown
- 1987-12-03 HK HK891/87A patent/HK89187A/xx unknown
- 1987-12-31 MY MY1987735A patent/MY8700735A/xx unknown
- 1987-12-31 MY MY1987585A patent/MY8700585A/xx unknown
-
1990
- 1990-11-09 DK DK268990A patent/DK164363C/da not_active IP Right Cessation
- 1990-11-09 DK DK269190A patent/DK164702C/da not_active IP Right Cessation
- 1990-11-09 DK DK269090A patent/DK164700C/da not_active IP Right Cessation
-
1992
- 1992-07-09 NL NL9201237A patent/NL9201237A/nl not_active Application Discontinuation
- 1992-07-09 NL NL9201236A patent/NL9201236A/nl not_active Application Discontinuation
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