JPS58180477A - ヒスタミンｈ↓２−受容体拮抗活性をもつ置換３，４−ジアミノ−１，２，５−チアジアゾ−ル - Google Patents
ヒスタミンｈ↓２−受容体拮抗活性をもつ置換３，４−ジアミノ−１，２，５−チアジアゾ−ルInfo
- Publication number
- JPS58180477A JPS58180477A JP58051740A JP5174083A JPS58180477A JP S58180477 A JPS58180477 A JP S58180477A JP 58051740 A JP58051740 A JP 58051740A JP 5174083 A JP5174083 A JP 5174083A JP S58180477 A JPS58180477 A JP S58180477A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydrogen
- lower alkyl
- hydrate
- compound
- 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.)
- Granted
Links
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 title description 18
- 229960001340 histamine Drugs 0.000 title description 9
- 230000003042 antagnostic effect Effects 0.000 title description 2
- IPLXKLUYTPGIPL-UHFFFAOYSA-N 1,2,5-thiadiazole-3,4-diamine Chemical class NC1=NSN=C1N IPLXKLUYTPGIPL-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 126
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 239000012453 solvate Substances 0.000 claims description 55
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 37
- 150000002431 hydrogen Chemical group 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- -1 2.2.2-)lifluoroethyl Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 231100000252 nontoxic Toxicity 0.000 claims description 24
- 230000003000 nontoxic effect Effects 0.000 claims description 24
- RDJGIQPSSNMJPF-UHFFFAOYSA-N ethanediimidamide Chemical compound NC(=N)C(N)=N RDJGIQPSSNMJPF-UHFFFAOYSA-N 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 150000004677 hydrates Chemical class 0.000 claims description 11
- 125000000325 methylidene group Chemical group [H]C([H])=* 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000006308 propyl amino group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 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 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
- 239000003440 toxic substance Substances 0.000 claims description 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- 210000000576 arachnoid Anatomy 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 150000003464 sulfur compounds Chemical class 0.000 claims 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 35
- 239000000203 mixture Substances 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 230000008018 melting Effects 0.000 description 26
- 238000002844 melting Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000004458 analytical method Methods 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 229910001868 water Inorganic materials 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 238000005259 measurement Methods 0.000 description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- QYIWBOWEQBEAGP-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)sulfanylisoindole-1,3-dione Chemical class O=C1C2=CC=CC=C2C(=O)N1SN1C(=O)C2=CC=CC=C2C1=O QYIWBOWEQBEAGP-UHFFFAOYSA-N 0.000 description 9
- 238000007429 general method Methods 0.000 description 9
- 230000028327 secretion Effects 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 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 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 230000002496 gastric effect Effects 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 5
- 229960001380 cimetidine Drugs 0.000 description 5
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 5
- 210000005245 right atrium Anatomy 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 3
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 3
- 229910017974 NH40H Inorganic materials 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000001746 atrial effect Effects 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
- 235000008504 concentrate Nutrition 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
- 210000002837 heart atrium Anatomy 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000001356 surgical procedure Methods 0.000 description 3
- VRALOCFIFDRXTC-UHFFFAOYSA-N 2-n'-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]ethanediimidamide Chemical compound NC(=N)C(=N)NCCCOC1=CC=CC(CN2CCCCC2)=C1 VRALOCFIFDRXTC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 244000018764 Nyssa sylvatica Species 0.000 description 2
- 235000003339 Nyssa sylvatica Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000010009 beating Methods 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
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition 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
- 239000004033 plastic Substances 0.000 description 2
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- 238000000746 purification Methods 0.000 description 2
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- 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
- 210000001519 tissue Anatomy 0.000 description 2
- 238000002627 tracheal intubation Methods 0.000 description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- YOTIBQOCCYWJMZ-UHFFFAOYSA-N 1,2,5-thiadiazole 1,1-dioxide Chemical compound O=S1(=O)N=CC=N1 YOTIBQOCCYWJMZ-UHFFFAOYSA-N 0.000 description 1
- LKFXYYLRIUSARI-UHFFFAOYSA-N 1,3-thiazol-5-amine Chemical compound NC1=CN=CS1 LKFXYYLRIUSARI-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- LSZMVESSGLHDJE-UHFFFAOYSA-N 2-bromo-4-methylpyridine Chemical group CC1=CC=NC(Br)=C1 LSZMVESSGLHDJE-UHFFFAOYSA-N 0.000 description 1
- GXZDYRYYNXYPMQ-UHFFFAOYSA-N 2-chloro-6-methylpyridine Chemical compound CC1=CC=CC(Cl)=N1 GXZDYRYYNXYPMQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- AVFWSRPBBZUMQK-UHFFFAOYSA-N 3-N-[3-[3-(pyrrolidin-1-ylmethyl)phenyl]sulfanylpropyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound NC1=NSN=C1NCCCSC1=CC(=CC=C1)CN1CCCC1 AVFWSRPBBZUMQK-UHFFFAOYSA-N 0.000 description 1
- CETVCWCSADQUBA-UHFFFAOYSA-N 3-[3-(piperidin-1-ylmethyl)phenyl]sulfanylpropan-1-amine Chemical compound NCCCSC1=CC=CC(CN2CCCCC2)=C1 CETVCWCSADQUBA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
- BEPUFQXSKMYDLW-UHFFFAOYSA-N 3-n-[3-[3-(morpholin-4-ylmethyl)phenoxy]propyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound NC1=NSN=C1NCCCOC1=CC=CC(CN2CCOCC2)=C1 BEPUFQXSKMYDLW-UHFFFAOYSA-N 0.000 description 1
- KESHAMUNPHJULK-UHFFFAOYSA-N 4-methoxy-1,2,5-thiadiazol-3-amine Chemical compound COC1=NSN=C1N KESHAMUNPHJULK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YQDWLHLUZWGZBN-UHFFFAOYSA-N 4-n-ethyl-1-oxo-3-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound CCNC1=NS(=O)N=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 YQDWLHLUZWGZBN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
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- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241001051525 Tortus Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000002350 accommodative effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 229940046011 buccal tablet Drugs 0.000 description 1
- 239000006189 buccal tablet Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- KXOFUUASPAGCPE-UHFFFAOYSA-N ethanediimidamide trihydrochloride Chemical compound Cl.Cl.Cl.C(C(N)=N)(N)=N KXOFUUASPAGCPE-UHFFFAOYSA-N 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 229960004931 histamine dihydrochloride Drugs 0.000 description 1
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
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- 210000003205 muscle Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 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
- 239000008188 pellet Substances 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 210000000253 proventriculus Anatomy 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36320782A | 1982-03-29 | 1982-03-29 | |
| US363207 | 1982-03-29 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5124585A Division JPH06135925A (ja) | 1982-03-29 | 1993-04-16 | ヒスタミンｈ▲２▼−受容体拮抗活性をもつ置換３，４−ジアミノ−１，２，５−チアジアゾール用中間体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58180477A true JPS58180477A (ja) | 1983-10-21 |
| JPH0568472B2 JPH0568472B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-09-29 |
Family
ID=23429274
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58051740A Granted JPS58180477A (ja) | 1982-03-29 | 1983-03-29 | ヒスタミンｈ↓２−受容体拮抗活性をもつ置換３，４−ジアミノ−１，２，５−チアジアゾ−ル |
| JP5124585A Pending JPH06135925A (ja) | 1982-03-29 | 1993-04-16 | ヒスタミンｈ▲２▼−受容体拮抗活性をもつ置換３，４−ジアミノ−１，２，５−チアジアゾール用中間体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5124585A Pending JPH06135925A (ja) | 1982-03-29 | 1993-04-16 | ヒスタミンｈ▲２▼−受容体拮抗活性をもつ置換３，４−ジアミノ−１，２，５−チアジアゾール用中間体 |
Country Status (30)
Families Citing this family (5)
| 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 |
| 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 |
| JPH0622828B2 (ja) * | 1986-06-30 | 1994-03-30 | フアナツク株式会社 | 直圧式型締機構 |
| 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 (5)
| 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 |
| FI76795C (fi) * | 1979-09-04 | 1988-12-12 | Bristol Myers Co | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 3,4-disubstituerade 1,2,5-tiadiazol-1-oxider och -1,1-dioxider samt nya mellanprodukter. |
| EP0040696B1 (en) * | 1980-04-30 | 1986-08-27 | Merck & Co. Inc. | Aminothiadiazoles as gastric secretion inhibitors |
| AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
-
1983
- 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
- 1983-03-25 NL NL8301063A patent/NL8301063A/nl not_active Application Discontinuation
- 1983-03-25 ZW ZW76/83A patent/ZW7683A1/xx unknown
- 1983-03-28 LU LU84716A patent/LU84716A1/fr unknown
- 1983-03-28 IE IE686/83A patent/IE55596B1/en not_active IP Right Cessation
- 1983-03-28 BE BE0/210417A patent/BE896291A/fr not_active IP Right Cessation
- 1983-03-28 DK DK141383A patent/DK166677B1/da not_active IP Right Cessation
- 1983-03-28 DE DE19833311281 patent/DE3311281A1/de not_active Withdrawn
- 1983-03-28 GB GB08308518A patent/GB2117769B/en not_active Expired
- 1983-03-28 NZ NZ203726A patent/NZ203726A/en unknown
- 1983-03-28 SU SU833568849A patent/SU1419518A3/ru active
- 1983-03-28 AU AU12907/83A patent/AU557577B2/en not_active Ceased
- 1983-03-28 HU HU831040A patent/HU188742B/hu not_active IP Right Cessation
- 1983-03-28 GR GR70903A patent/GR78524B/el unknown
- 1983-03-28 IT IT48005/83A patent/IT1164633B/it active
- 1983-03-28 HU HU854071A patent/HU196386B/hu not_active IP Right Cessation
- 1983-03-28 PT PT76459A patent/PT76459B/pt not_active IP Right Cessation
- 1983-03-28 IL IL68259A patent/IL68259A0/xx not_active IP Right Cessation
- 1983-03-28 SE SE8301725A patent/SE461040B/sv not_active IP Right Cessation
- 1983-03-28 NO NO831100A patent/NO163055C/no unknown
- 1983-03-29 CH CH1749/83A patent/CH655111A5/de not_active IP Right Cessation
- 1983-03-29 AT AT0111083A patent/AT386599B/de not_active IP Right Cessation
- 1983-03-29 JP JP58051740A patent/JPS58180477A/ja active Granted
- 1983-03-29 OA OA57955A patent/OA07356A/xx unknown
- 1983-03-29 CS CS832191A patent/CS250229B2/cs unknown
- 1983-03-29 YU YU744/83A patent/YU44849B/xx unknown
- 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 KR KR1019830001283A patent/KR880002209B1/ko not_active Expired
- 1983-03-29 DD DD83260707A patent/DD219768A5/de not_active IP Right Cessation
- 1983-03-29 DD DD83249300A patent/DD210909A5/de not_active IP Right Cessation
- 1983-11-30 ES ES527685A patent/ES8505977A1/es not_active Expired
- 1983-11-30 ES ES527686A patent/ES527686A0/es active Granted
-
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
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