CA1143727A - Triazole derivatives - Google Patents
Triazole derivativesInfo
- Publication number
- CA1143727A CA1143727A CA000326446A CA326446A CA1143727A CA 1143727 A CA1143727 A CA 1143727A CA 000326446 A CA000326446 A CA 000326446A CA 326446 A CA326446 A CA 326446A CA 1143727 A CA1143727 A CA 1143727A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- group
- alkyl
- formula
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 231
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 79
- 239000001257 hydrogen Substances 0.000 claims abstract description 78
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 72
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 66
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 18
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 16
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 238000010348 incorporation Methods 0.000 claims abstract description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000004677 hydrates Chemical class 0.000 claims abstract description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000004475 heteroaralkyl group Chemical group 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims abstract description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 110
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 106
- 238000000034 method Methods 0.000 claims description 60
- 230000008569 process Effects 0.000 claims description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 39
- -1 carbamoyl halide Chemical class 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 17
- 230000009467 reduction Effects 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 239000005864 Sulphur Substances 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 150000004702 methyl esters Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- HOJVXOFVCLMYDW-UHFFFAOYSA-N 1-(benzylideneamino)-3-cyano-1-methylthiourea Chemical compound N#CN=C(S)N(C)N=CC1=CC=CC=C1 HOJVXOFVCLMYDW-UHFFFAOYSA-N 0.000 claims description 2
- VQSXCZMVUMSITD-UHFFFAOYSA-N 3-[3-(piperidin-1-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCC2)=C1 VQSXCZMVUMSITD-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- 125000005543 phthalimide group Chemical group 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 20
- 239000000126 substance Substances 0.000 claims 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- NRIGRKAXOLMTSK-UHFFFAOYSA-N Lamtidine Chemical compound CN1N=C(N)N=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 NRIGRKAXOLMTSK-UHFFFAOYSA-N 0.000 claims 4
- 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 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 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- PODOXIQYNGYYDA-UHFFFAOYSA-N 1-methyl-5-n-[3-[3-(pyrrolidin-1-ylmethyl)phenoxy]propyl]-1,2,4-triazole-3,5-diamine Chemical compound CN1N=C(N)N=C1NCCCOC1=CC=CC(CN2CCCC2)=C1 PODOXIQYNGYYDA-UHFFFAOYSA-N 0.000 claims 1
- OQHBPIQEZCWZQM-UHFFFAOYSA-N 5-N-[3-[3-(bromomethyl)phenoxy]propyl]-1-methyl-1,2,4-triazole-3,5-diamine hydrobromide Chemical compound Br.CN1N=C(N=C1NCCCOC1=CC(=CC=C1)CBr)N OQHBPIQEZCWZQM-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 abstract description 6
- 125000005842 heteroatom Chemical group 0.000 abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 3
- 239000003485 histamine H2 receptor antagonist Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 270
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 258
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 233
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 201
- 239000000377 silicon dioxide Substances 0.000 description 113
- 229910021529 ammonia Inorganic materials 0.000 description 101
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 94
- 229940093499 ethyl acetate Drugs 0.000 description 90
- 235000019439 ethyl acetate Nutrition 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
- 239000000203 mixture Substances 0.000 description 71
- 239000000243 solution Substances 0.000 description 57
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
- 239000003921 oil Substances 0.000 description 52
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 239000002904 solvent Substances 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 32
- 239000007787 solid Substances 0.000 description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 31
- 150000004985 diamines Chemical class 0.000 description 30
- 238000010992 reflux Methods 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 21
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 20
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 19
- 101150041968 CDC13 gene Proteins 0.000 description 17
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 16
- 238000006722 reduction reaction Methods 0.000 description 15
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 14
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 12
- 239000012279 sodium borohydride Substances 0.000 description 12
- 229910000033 sodium borohydride Inorganic materials 0.000 description 12
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- PKWIYNIDEDLDCJ-UHFFFAOYSA-N guanazole Chemical compound NC1=NNC(N)=N1 PKWIYNIDEDLDCJ-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 150000002466 imines Chemical class 0.000 description 9
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
- 239000002024 ethyl acetate extract Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- DQSBZDLZCZUJCJ-UHFFFAOYSA-N 2h-triazole-4,5-diamine Chemical compound NC=1N=NNC=1N DQSBZDLZCZUJCJ-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- STFQKTFSSBLPHJ-UHFFFAOYSA-N methyl n-(benzylideneamino)-n'-cyano-n-methylcarbamimidothioate Chemical compound N#CN=C(SC)N(C)N=CC1=CC=CC=C1 STFQKTFSSBLPHJ-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ZEQMMXMSZSMEND-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]phenoxy]propan-1-amine Chemical compound CN(C)CC1=CC=CC(OCCCN)=C1 ZEQMMXMSZSMEND-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
- 229910000091 aluminium hydride Inorganic materials 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 3
- ORGBERFQYFWYGX-UHFFFAOYSA-N 3-(piperidin-1-ylmethyl)phenol Chemical compound OC1=CC=CC(CN2CCCCC2)=C1 ORGBERFQYFWYGX-UHFFFAOYSA-N 0.000 description 3
- 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 3
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- IEDVZQPKBYYNGD-UHFFFAOYSA-N methyl n-amino-n'-cyano-n-methylcarbamimidothioate Chemical compound CSC(N(C)N)=NC#N IEDVZQPKBYYNGD-UHFFFAOYSA-N 0.000 description 1
- MYZRBZJVCYSTST-UHFFFAOYSA-N methyl n-cyano-n'-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]carbamimidothioate Chemical compound N#CNC(SC)=NCCSCC1=CC=C(CN(C)C)O1 MYZRBZJVCYSTST-UHFFFAOYSA-N 0.000 description 1
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- IMYBWPUHVYRSJG-UHFFFAOYSA-M potassium;2-aminoethanesulfonate Chemical compound [K+].NCCS([O-])(=O)=O IMYBWPUHVYRSJG-UHFFFAOYSA-M 0.000 description 1
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- 230000000069 prophylactic effect Effects 0.000 description 1
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- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 239000012485 toluene extract Substances 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
- 229940055764 triaz Drugs 0.000 description 1
- HUUBMTMJIQHAEN-UHFFFAOYSA-N triazole-1,4-diamine Chemical compound NC1=CN(N)N=N1 HUUBMTMJIQHAEN-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
-
- 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
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16468/78 | 1978-04-26 | ||
| GB1646878 | 1978-04-26 | ||
| GB47689/78 | 1978-12-08 | ||
| GB7847689 | 1978-12-08 | ||
| GB7907422 | 1979-03-02 | ||
| GB79/07422 | 1979-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1143727A true CA1143727A (en) | 1983-03-29 |
Family
ID=27257387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000326446A Expired CA1143727A (en) | 1978-04-26 | 1979-04-26 | Triazole derivatives |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US4318913A (en, 2012) |
| AR (1) | AR228941A1 (en, 2012) |
| AT (1) | AT376212B (en, 2012) |
| AU (1) | AU531224B2 (en, 2012) |
| CA (1) | CA1143727A (en, 2012) |
| CH (1) | CH647767A5 (en, 2012) |
| DE (2) | DE2917026A1 (en, 2012) |
| DK (1) | DK173579A (en, 2012) |
| ES (4) | ES479988A0 (en, 2012) |
| FI (1) | FI791360A7 (en, 2012) |
| FR (1) | FR2432511B1 (en, 2012) |
| IL (1) | IL57178A (en, 2012) |
| IT (1) | IT1162304B (en, 2012) |
| LU (1) | LU81192A1 (en, 2012) |
| NL (1) | NL7903313A (en, 2012) |
| NO (1) | NO791387L (en, 2012) |
| NZ (1) | NZ190299A (en, 2012) |
| PH (1) | PH19534A (en, 2012) |
| SE (1) | SE7903698L (en, 2012) |
| YU (2) | YU100379A (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR228941A1 (es) * | 1978-04-26 | 1983-05-13 | Glaxo Group Ltd | Procedimiento para preparar nuevos derivados de 3,5-diamino-1,2,4-triazol que son activos contra receptores histaminicos |
| GB2047238B (en) * | 1979-03-02 | 1983-09-14 | Glaxo Group Ltd | Triazole derivatives processes for their production and pharmaceutical compositions containing them |
| US4410523A (en) * | 1979-10-22 | 1983-10-18 | Glaxo Group Limited | Heterocyclic derivatives |
| US4777179A (en) * | 1979-10-23 | 1988-10-11 | Glaxo Group Limited | Heterocyclic derivatives, processes for the use thereof and pharmaceutical compositions containing them |
| FR2477150A1 (fr) * | 1980-02-28 | 1981-09-04 | Glaxo Group Ltd | Nouveaux derives heterocycliques, procedes pour leur preparation et compositions pharmaceutiques les comportant |
| AU548426B2 (en) * | 1980-08-27 | 1985-12-12 | Glaxo Group Limited | 3-amino-(1,2,4)-triazoles |
| US4399294A (en) * | 1980-12-30 | 1983-08-16 | Glaxo Group Limited | Process for the preparation of a furan derivative |
| DK558181A (da) * | 1981-01-30 | 1982-07-31 | Smithkline Corp | Fremgangsmaade til fremstilling af 3,5-diamino-1,2,4-triazoler |
| 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 |
| IE53068B1 (en) * | 1981-06-15 | 1988-05-25 | Merck & Co Inc | Diamino isothiazole-1-oxides and -1,1-dioxides as gastic secretion inhibitors |
| EP0070743A3 (en) * | 1981-07-22 | 1983-10-12 | Glaxo Group Limited | Pharmaceutical compositions containing compounds having action on histamine receptors |
| CA1192545A (en) * | 1982-02-16 | 1985-08-27 | Glaxo Group Limited | Heterocyclic derivatives as histamine h.sub.2- antagonists |
| ZA831263B (en) * | 1982-02-24 | 1984-10-31 | Glaxo Group Ltd | Heterocyclic derivatives |
| US4482552A (en) * | 1982-02-26 | 1984-11-13 | Glaxo Group Limited | Triazole compounds and their pharmaceutical use |
| EP0089153B1 (en) * | 1982-03-17 | 1986-09-24 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| US4520025A (en) * | 1982-07-21 | 1985-05-28 | William H. Rorer, Inc. | Bicyclic nitrogen heterocyclic ethers and thioethers, and their pharmaceutical uses |
| US4543352A (en) * | 1983-04-29 | 1985-09-24 | William H. Rorer, Inc. | Naphthalene aminoalkylene ethers and thioethers, and their pharmaceutical uses |
| US4529723A (en) * | 1983-04-29 | 1985-07-16 | William H. Rorer, Inc. | Bicyclic benzenoid aminoalkylene ethers and thioethers, pharmaceutical compositions and use |
| US4481360A (en) * | 1983-08-26 | 1984-11-06 | The Upjohn Company | 4H-1,2,4-Triazol-3-yl compounds |
| DE3336410A1 (de) * | 1983-10-06 | 1985-04-18 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Sulfenamidderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3404786A1 (de) * | 1984-02-10 | 1985-08-14 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Neue alkanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltendes arzneimittel |
| US4812451A (en) * | 1984-10-19 | 1989-03-14 | A. H. Robins Company, Incorporated | 1-(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl)-α,.alpha. |
| US4812452A (en) * | 1984-10-19 | 1989-03-14 | A. H. Robins Company, Incorporated | 1-((aminoalkyl and aminoalkylamino) carbonyl and thiocarbonyl)-α,α-diarylpyrrolidine, piperidine and homopiperidineacetamides and acetonitriles |
| DE3568374D1 (en) * | 1985-12-20 | 1989-03-30 | Litef Gmbh | Method to determine heading by using and automatically calibrating a 3-axis magnetometer rigidly fitted in an aircraft |
| US4988828A (en) * | 1987-11-27 | 1991-01-29 | Fujirebio Kabushiki Kaisha | Phenoxypropyl derivatives |
| US5028716A (en) * | 1989-01-30 | 1991-07-02 | Taisho Pharmaceutical Co., Ltd. | 3,5-diamino-1,2,4-triazole derivatives |
| GB9009437D0 (en) * | 1990-04-26 | 1990-06-20 | Glaxo Group Ltd | Chemical compounds |
| RU2292340C1 (ru) * | 2005-05-23 | 2007-01-27 | Государственное образовательное учреждение высшего профессионального образования "Южно-Российский государственный технический университет (Новочеркасский политехнический институт)", ГОУ ВПО ЮРГТУ (НПИ) | Способ получения r-метилпроизводных 3,5-диамино-1,2,4-триазола |
| 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 (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1419994A (en) | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
| SU557574A1 (ru) | 1975-07-02 | 1978-03-05 | Ордена Трудового Красного Знамени Научно-Исследовательский Институт Экспериментальной Медицины Амн Ссср | Способ получени 3-амино-5-(2-аминоэтил)-1,2,4-триазола |
| SU596577A1 (ru) | 1976-02-23 | 1978-03-05 | Ордена Трудового Красного Знамени Научно-Исследовательский Институт Экспериментальной Медицины | -Метил- "/4-(5 амино-1,2,4триазолил-3)-бутил/-тиомочевина, про вл юща антигистаминовую активность, и способ ее получени |
| GB1565966A (en) * | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
| IE46886B1 (en) * | 1977-05-17 | 1983-10-19 | Allen & Hanburys Ltd | Aminoalkyl-benzene derivatives |
| GB1601459A (en) * | 1977-05-17 | 1981-10-28 | Allen & Hanburys Ltd | Aminoalkyl thiophene derivatives |
| US4115860A (en) * | 1977-06-02 | 1978-09-19 | Lockheed Electronics Co., Inc. | Plural load power controller with time-shared processor |
| DE2835695A1 (de) | 1977-08-29 | 1979-03-15 | Yamanouchi Pharma Co Ltd | Neue heterocyclische verbindungen, verfahren zu ihrer herstellung und arzneimittel, die diese enthalten |
| AR228941A1 (es) * | 1978-04-26 | 1983-05-13 | Glaxo Group Ltd | Procedimiento para preparar nuevos derivados de 3,5-diamino-1,2,4-triazol que son activos contra receptores histaminicos |
| US4293557A (en) * | 1979-07-03 | 1981-10-06 | Teikoku Hormone Mfg. Co., Ltd. | Antiulcer phenoxypropylamine derivatives |
| EP0040696B1 (en) * | 1980-04-30 | 1986-08-27 | Merck & Co. Inc. | Aminothiadiazoles as gastric secretion inhibitors |
| US4390701A (en) * | 1981-05-18 | 1983-06-28 | Bristol-Myers Company | 1-Amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione |
| GR77847B (en, 2012) * | 1981-12-14 | 1984-09-25 | American Home Prod | |
| JPS6067474A (ja) * | 1983-09-24 | 1985-04-17 | Wakamoto Pharmaceut Co Ltd | 新規な１，３，４−チアジアゾ−ル誘導体及びそれを有効成分とする抗潰瘍剤 |
| DE3513184A1 (de) * | 1985-04-12 | 1986-10-16 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | 1,3,4-thiadiazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
-
1979
- 1979-04-20 AR AR276253A patent/AR228941A1/es active
- 1979-04-25 FR FR7910459A patent/FR2432511B1/fr not_active Expired
- 1979-04-25 CH CH3909/79A patent/CH647767A5/de not_active IP Right Cessation
- 1979-04-26 DK DK173579A patent/DK173579A/da active IP Right Grant
- 1979-04-26 NL NL7903313A patent/NL7903313A/xx not_active Application Discontinuation
- 1979-04-26 AT AT0316679A patent/AT376212B/de not_active IP Right Cessation
- 1979-04-26 YU YU01003/79A patent/YU100379A/xx unknown
- 1979-04-26 NZ NZ190299A patent/NZ190299A/xx unknown
- 1979-04-26 IT IT48856/79A patent/IT1162304B/it active
- 1979-04-26 LU LU81192A patent/LU81192A1/fr unknown
- 1979-04-26 CA CA000326446A patent/CA1143727A/en not_active Expired
- 1979-04-26 DE DE19792917026 patent/DE2917026A1/de not_active Ceased
- 1979-04-26 PH PH22427A patent/PH19534A/en unknown
- 1979-04-26 AU AU46482/79A patent/AU531224B2/en not_active Ceased
- 1979-04-26 NO NO791387A patent/NO791387L/no unknown
- 1979-04-26 ES ES479988A patent/ES479988A0/es active Granted
- 1979-04-26 US US06/033,508 patent/US4318913A/en not_active Expired - Lifetime
- 1979-04-26 DE DE2954639A patent/DE2954639C2/de not_active Expired - Fee Related
- 1979-04-26 FI FI791360A patent/FI791360A7/fi not_active Application Discontinuation
- 1979-04-26 SE SE7903698A patent/SE7903698L/xx not_active Application Discontinuation
- 1979-04-30 IL IL57178A patent/IL57178A/xx unknown
-
1980
- 1980-02-16 ES ES488676A patent/ES488676A0/es active Granted
- 1980-02-16 ES ES488677A patent/ES8101564A1/es not_active Expired
- 1980-02-16 ES ES488678A patent/ES488678A0/es active Granted
-
1981
- 1981-11-24 US US06/324,440 patent/US4442110A/en not_active Expired - Fee Related
-
1983
- 1983-01-25 YU YU00161/83A patent/YU16183A/xx unknown
-
1986
- 1986-02-06 US US06/826,832 patent/US4764612A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES8101563A1 (es) | 1980-12-16 |
| CH647767A5 (de) | 1985-02-15 |
| IL57178A0 (en) | 1979-07-25 |
| LU81192A1 (fr) | 1980-05-07 |
| DE2917026A1 (de) | 1979-11-08 |
| ES488677A0 (es) | 1980-12-16 |
| FI791360A7 (fi) | 1981-01-01 |
| NO791387L (no) | 1979-10-29 |
| AU4648279A (en) | 1979-11-01 |
| US4764612A (en) | 1988-08-16 |
| US4442110A (en) | 1984-04-10 |
| NL7903313A (nl) | 1979-10-30 |
| FR2432511A1 (fr) | 1980-02-29 |
| YU100379A (en) | 1983-04-30 |
| ES8102104A1 (es) | 1980-08-16 |
| PH19534A (en) | 1986-05-20 |
| ES8101565A1 (es) | 1980-12-16 |
| ES488678A0 (es) | 1980-12-16 |
| NZ190299A (en) | 1982-05-31 |
| DE2954639C2 (en, 2012) | 1990-09-27 |
| ES488676A0 (es) | 1980-12-16 |
| ES8101564A1 (es) | 1980-12-16 |
| IT7948856A0 (it) | 1979-04-26 |
| ATA316679A (de) | 1984-03-15 |
| FR2432511B1 (fr) | 1986-04-25 |
| ES479988A0 (es) | 1980-08-16 |
| IT1162304B (it) | 1987-03-25 |
| US4318913A (en) | 1982-03-09 |
| YU16183A (en) | 1983-04-30 |
| AR228941A1 (es) | 1983-05-13 |
| AT376212B (de) | 1984-10-25 |
| AU531224B2 (en) | 1983-08-18 |
| IL57178A (en) | 1984-11-30 |
| SE7903698L (sv) | 1979-10-27 |
| DK173579A (da) | 1979-10-27 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |