DE3311281A1 - Thiadiazol-derivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
Thiadiazol-derivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE3311281A1 DE3311281A1 DE19833311281 DE3311281A DE3311281A1 DE 3311281 A1 DE3311281 A1 DE 3311281A1 DE 19833311281 DE19833311281 DE 19833311281 DE 3311281 A DE3311281 A DE 3311281A DE 3311281 A1 DE3311281 A1 DE 3311281A1
- Authority
- DE
- Germany
- Prior art keywords
- solvate
- hydrate
- thiadiazole
- methyl
- salt
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 32
- 150000004867 thiadiazoles Chemical class 0.000 title description 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 129
- -1 methylenedioxy Chemical group 0.000 claims description 79
- 239000012453 solvate Substances 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 231100000252 nontoxic Toxicity 0.000 claims description 29
- 230000003000 nontoxic effect Effects 0.000 claims description 29
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 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
- 150000004677 hydrates Chemical class 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 6
- RDJGIQPSSNMJPF-UHFFFAOYSA-N ethanediimidamide Chemical compound NC(=N)C(N)=N RDJGIQPSSNMJPF-UHFFFAOYSA-N 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- DRGIXHISBNDJEL-UHFFFAOYSA-N 3-n-[3-[3-(pyrrolidin-1-ylmethyl)phenoxy]propyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound NC1=NSN=C1NCCCOC1=CC=CC(CN2CCCC2)=C1 DRGIXHISBNDJEL-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims description 4
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- MIUWQWMRZOEFEX-UHFFFAOYSA-N 3-n-benzyl-4-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound C=1C=CC(CN2CCCCC2)=CC=1OCCCNC1=NSN=C1NCC1=CC=CC=C1 MIUWQWMRZOEFEX-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- IRQUPRKBBWVPAU-UHFFFAOYSA-N 2-n'-[3-[3-(pyrrolidin-1-ylmethyl)phenoxy]propyl]ethanediimidamide Chemical compound NC(=N)C(=N)NCCCOC1=CC=CC(CN2CCCC2)=C1 IRQUPRKBBWVPAU-UHFFFAOYSA-N 0.000 claims description 2
- OETKCBJTZXIZMO-UHFFFAOYSA-N 2-n'-[3-[6-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropyl]ethanediimidamide Chemical compound NC(=N)C(=N)NCCCOC1=CC=CC(CN2CCCCC2)=N1 OETKCBJTZXIZMO-UHFFFAOYSA-N 0.000 claims description 2
- JRHOBGUKGKDYFU-UHFFFAOYSA-N 3-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound NC1=NSN=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 JRHOBGUKGKDYFU-UHFFFAOYSA-N 0.000 claims description 2
- XGRRSCZJFCJRGY-UHFFFAOYSA-N 4-n-methyl-3-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound CNC1=NSN=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 XGRRSCZJFCJRGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- LBNPMRUENVBXOR-UHFFFAOYSA-N 2-n'-[3-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropyl]ethanediimidamide Chemical compound C1=NC(OCCCNC(=N)C(=N)N)=CC(CN2CCCCC2)=C1 LBNPMRUENVBXOR-UHFFFAOYSA-N 0.000 claims 1
- YVFNSFYHKSSVRN-UHFFFAOYSA-N 3-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1,2,5-thiadiazole-3,4-diamine;hydrochloride Chemical compound Cl.NC1=NSN=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 YVFNSFYHKSSVRN-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000000047 product Substances 0.000 description 43
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 30
- 125000006308 propyl amino group Chemical group 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 24
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 23
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000725 suspension Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- 229960001340 histamine Drugs 0.000 description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 210000002837 heart atrium Anatomy 0.000 description 8
- 230000028327 secretion Effects 0.000 description 8
- 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 7
- 241001465754 Metazoa Species 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000002496 gastric effect Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- QYIWBOWEQBEAGP-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)sulfanylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1SN1C(=O)C2=CC=CC=C2C1=O QYIWBOWEQBEAGP-UHFFFAOYSA-N 0.000 description 5
- 241000700199 Cavia porcellus Species 0.000 description 5
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 239000002464 receptor antagonist Substances 0.000 description 4
- 229940044551 receptor antagonist Drugs 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- ZZGPYPVNEPAJHG-UHFFFAOYSA-N 1,2,5-thiadiazole 1-oxide Chemical compound O=S1N=CC=N1 ZZGPYPVNEPAJHG-UHFFFAOYSA-N 0.000 description 3
- ZJISWUHWDYNKFX-UHFFFAOYSA-N 2-n'-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]ethanediimidamide;trihydrochloride Chemical compound Cl.Cl.Cl.NC(=N)C(=N)NCCCOC1=CC=CC(CN2CCCCC2)=C1 ZJISWUHWDYNKFX-UHFFFAOYSA-N 0.000 description 3
- WEKYWIBCHONDBC-UHFFFAOYSA-N 3-[6-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCC2)=N1 WEKYWIBCHONDBC-UHFFFAOYSA-N 0.000 description 3
- OHLUAARMJNNWIK-UHFFFAOYSA-N 4-methoxy-1-oxo-1,2,5-thiadiazol-3-amine Chemical compound COC1=NS(=O)N=C1N OHLUAARMJNNWIK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 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 description 2
- VOEMYPMXKXCFCF-UHFFFAOYSA-N 1-oxo-3-n-[3-[6-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound NC1=NS(=O)N=C1NCCCOC1=CC=CC(CN2CCCCC2)=N1 VOEMYPMXKXCFCF-UHFFFAOYSA-N 0.000 description 2
- AAEOEVRPMYKMKS-UHFFFAOYSA-N 3-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropan-1-amine Chemical compound C1=NC(OCCCN)=CC(CN2CCCCC2)=C1 AAEOEVRPMYKMKS-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 206010065713 Gastric Fistula Diseases 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 208000008469 Peptic Ulcer Diseases 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910000071 diazene Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- KXOFUUASPAGCPE-UHFFFAOYSA-N ethanediimidamide trihydrochloride Chemical compound Cl.Cl.Cl.C(C(N)=N)(N)=N KXOFUUASPAGCPE-UHFFFAOYSA-N 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
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- 208000011906 peptic ulcer disease Diseases 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 210000005245 right atrium Anatomy 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000002627 tracheal intubation Methods 0.000 description 2
- BMSZNJAHQMIOMH-TYYBGVCCSA-N (e)-but-2-enedioic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.OC(=O)\C=C\C(O)=O BMSZNJAHQMIOMH-TYYBGVCCSA-N 0.000 description 1
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 description 1
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- YSHYTDNFZOCORJ-UHFFFAOYSA-N 1-N'-methyl-2-N'-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]ethanediimidamide trihydrochloride Chemical compound Cl.Cl.Cl.CNC(C(NCCCOC1=CC(=CC=C1)CN1CCCCC1)=N)=N YSHYTDNFZOCORJ-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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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
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- 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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (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)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36320782A | 1982-03-29 | 1982-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3311281A1 true DE3311281A1 (de) | 1983-11-24 |
Family
ID=23429274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833311281 Withdrawn DE3311281A1 (de) | 1982-03-29 | 1983-03-28 | Thiadiazol-derivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
Country Status (30)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3522101A1 (de) * | 1984-06-22 | 1986-01-02 | Bristol-Myers Co., New York, N.Y. | 3,4-diamino-1,2,5-thiadiazol-verbindungen, verfahren zu deren herstellung und diese verbindungen enthaltende pharamazeutische mittel |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| US4593039A (en) * | 1984-04-02 | 1986-06-03 | Merck & Co., Inc. | 1-aryloxy-3-(substituted aminoalkylamino)-2-propanols |
| JPH0622828B2 (ja) * | 1986-06-30 | 1994-03-30 | フアナツク株式会社 | 直圧式型締機構 |
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3033169A1 (de) * | 1979-09-04 | 1981-03-19 | Bristol-Myers Co., New York, N.Y. | 3,4-disubstituierte 1,2,5-thiadiazol-1-oxide und -1,1-dioxide |
| EP0040696A2 (en) * | 1980-04-30 | 1981-12-02 | Merck & Co. Inc. | Aminothiadiazoles as gastric secretion inhibitors |
| EP0112142A2 (en) * | 1982-12-14 | 1984-06-27 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3018289A (en) * | 1960-02-10 | 1962-01-23 | Wyandotte Chemicals Corp | Process for preparing oxamidines |
| GB1595291A (en) * | 1976-09-21 | 1981-08-12 | Smith Kline French Lab | Pyrimidone and thiopyrimidone derivatives |
-
1983
- 1983-03-25 ZW ZW76/83A patent/ZW7683A1/xx unknown
- 1983-03-25 NL NL8301063A patent/NL8301063A/nl not_active Application Discontinuation
- 1983-03-25 FR FR838304934A patent/FR2542741B1/fr not_active Expired
- 1983-03-25 ZA ZA832154A patent/ZA832154B/xx unknown
- 1983-03-25 ES ES520982A patent/ES8404683A1/es not_active Expired
- 1983-03-28 GB GB08308518A patent/GB2117769B/en not_active Expired
- 1983-03-28 NO NO831100A patent/NO163055C/no unknown
- 1983-03-28 IL IL68259A patent/IL68259A0/xx not_active IP Right Cessation
- 1983-03-28 DK DK141383A patent/DK166677B1/da not_active IP Right Cessation
- 1983-03-28 GR GR70903A patent/GR78524B/el unknown
- 1983-03-28 SU SU833568849A patent/SU1419518A3/ru active
- 1983-03-28 HU HU854071A patent/HU196386B/hu not_active IP Right Cessation
- 1983-03-28 NZ NZ203726A patent/NZ203726A/en unknown
- 1983-03-28 PT PT76459A patent/PT76459B/pt not_active IP Right Cessation
- 1983-03-28 IT IT48005/83A patent/IT1164633B/it active
- 1983-03-28 BE BE0/210417A patent/BE896291A/fr not_active IP Right Cessation
- 1983-03-28 SE SE8301725A patent/SE461040B/sv not_active IP Right Cessation
- 1983-03-28 IE IE686/83A patent/IE55596B1/en not_active IP Right Cessation
- 1983-03-28 LU LU84716A patent/LU84716A1/fr unknown
- 1983-03-28 HU HU831040A patent/HU188742B/hu not_active IP Right Cessation
- 1983-03-28 DE DE19833311281 patent/DE3311281A1/de not_active Withdrawn
- 1983-03-28 AU AU12907/83A patent/AU557577B2/en not_active Ceased
- 1983-03-29 JP JP58051740A patent/JPS58180477A/ja active Granted
- 1983-03-29 KR KR1019830001283A patent/KR880002209B1/ko not_active Expired
- 1983-03-29 DD DD83260707A patent/DD219768A5/de not_active IP Right Cessation
- 1983-03-29 CS CS841958A patent/CS250240B2/cs unknown
- 1983-03-29 CH CH575/86A patent/CH660880A5/de not_active IP Right Cessation
- 1983-03-29 CS CS832191A patent/CS250229B2/cs unknown
- 1983-03-29 DD DD83249300A patent/DD210909A5/de not_active IP Right Cessation
- 1983-03-29 AT AT0111083A patent/AT386599B/de not_active IP Right Cessation
- 1983-03-29 YU YU744/83A patent/YU44849B/xx unknown
- 1983-03-29 OA OA57955A patent/OA07356A/xx unknown
- 1983-03-29 CH CH1749/83A patent/CH655111A5/de not_active IP Right Cessation
- 1983-11-30 ES ES527685A patent/ES8505977A1/es not_active Expired
- 1983-11-30 ES ES527686A patent/ES8505978A1/es not_active Expired
-
1984
- 1984-06-08 SU SU843750493A patent/SU1355123A3/ru active
- 1984-12-31 GB GB08432809A patent/GB2149406B/en not_active Expired
-
1986
- 1986-09-30 AU AU63272/86A patent/AU586037B2/en not_active Ceased
-
1987
- 1987-05-22 FR FR878707197A patent/FR2597867B1/fr not_active Expired
- 1987-11-25 SE SE8704689A patent/SE464302B/sv not_active IP Right Cessation
- 1987-12-30 MY MY942/87A patent/MY8700942A/xx unknown
-
1992
- 1992-06-18 DK DK92811A patent/DK81192D0/da not_active Application Discontinuation
-
1993
- 1993-04-16 JP JP5124585A patent/JPH06135925A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3033169A1 (de) * | 1979-09-04 | 1981-03-19 | Bristol-Myers Co., New York, N.Y. | 3,4-disubstituierte 1,2,5-thiadiazol-1-oxide und -1,1-dioxide |
| EP0040696A2 (en) * | 1980-04-30 | 1981-12-02 | Merck & Co. Inc. | Aminothiadiazoles as gastric secretion inhibitors |
| EP0112142A2 (en) * | 1982-12-14 | 1984-06-27 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
Non-Patent Citations (2)
| Title |
|---|
| Adv. Heterocyclic Chem., Vol. 9, 1968, S. 115-123 * |
| Comprehensive Organic Chemistry, Vol. 4, 1979, S. 1046 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3522101A1 (de) * | 1984-06-22 | 1986-01-02 | Bristol-Myers Co., New York, N.Y. | 3,4-diamino-1,2,5-thiadiazol-verbindungen, verfahren zu deren herstellung und diese verbindungen enthaltende pharamazeutische mittel |
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Legal Events
| Date | Code | Title | Description |
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| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: BRISTOL-MYERS SQUIBB CO. (N.D.GES.D.STAATES DELAWA |
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| 8128 | New person/name/address of the agent |
Representative=s name: KINZEBACH, W., DIPL.-CHEM. DR.PHIL. RIEDL, P., DIP |
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| 8130 | Withdrawal |