CS250229B2 - Method of 3,4-diamino-1,2,5-thiadiazole derivatives' production - Google Patents
Method of 3,4-diamino-1,2,5-thiadiazole derivatives' production Download PDFInfo
- Publication number
- CS250229B2 CS250229B2 CS832191A CS219183A CS250229B2 CS 250229 B2 CS250229 B2 CS 250229B2 CS 832191 A CS832191 A CS 832191A CS 219183 A CS219183 A CS 219183A CS 250229 B2 CS250229 B2 CS 250229B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- thiadiazole
- amino
- propylamino
- give
- oxide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 40
- IPLXKLUYTPGIPL-UHFFFAOYSA-N 1,2,5-thiadiazole-3,4-diamine Chemical class NC1=NSN=C1N IPLXKLUYTPGIPL-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000012453 solvate Substances 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 11
- 231100000252 nontoxic Toxicity 0.000 claims description 11
- 230000003000 nontoxic effect Effects 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000004677 hydrates Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 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 claims description 4
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- 150000001875 compounds Chemical class 0.000 description 74
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- -1 3,4-disubstituted-1,2,5-thiadiazole-1-oxides Chemical class 0.000 description 44
- 239000000047 product Substances 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- 125000006308 propyl amino group Chemical group 0.000 description 40
- 239000000203 mixture Substances 0.000 description 34
- 229910052799 carbon Inorganic materials 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 238000004458 analytical method Methods 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 25
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 229960001340 histamine Drugs 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 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 10
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 7
- 229960001380 cimetidine Drugs 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 6
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 241000700199 Cavia porcellus Species 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 210000002784 stomach Anatomy 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
- 239000002253 acid Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 125000003386 piperidinyl group Chemical group 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 210000005245 right atrium Anatomy 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 4
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 3
- 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 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
- 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 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 210000002837 heart atrium Anatomy 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ZZGPYPVNEPAJHG-UHFFFAOYSA-N 1,2,5-thiadiazole 1-oxide Chemical compound O=S1N=CC=N1 ZZGPYPVNEPAJHG-UHFFFAOYSA-N 0.000 description 2
- GHNPLMVOPREYJH-UHFFFAOYSA-N 2-n'-[2-[[5-(piperidin-1-ylmethyl)thiophen-3-yl]methylsulfanyl]ethyl]ethanediimidamide;trihydrochloride Chemical compound Cl.Cl.Cl.NC(=N)C(=N)NCCSCC1=CSC(CN2CCCCC2)=C1 GHNPLMVOPREYJH-UHFFFAOYSA-N 0.000 description 2
- GCPNDUGDDPCEAY-UHFFFAOYSA-N 2-n'-[2-[[5-[(dimethylamino)methyl]thiophen-3-yl]methylsulfanyl]ethyl]ethanediimidamide;trihydrochloride Chemical compound Cl.Cl.Cl.CN(C)CC1=CC(CSCCNC(=N)C(N)=N)=CS1 GCPNDUGDDPCEAY-UHFFFAOYSA-N 0.000 description 2
- KULYHDQCRCSIHF-UHFFFAOYSA-N 2-n'-[3-[3-(pyrrolidin-1-ylmethyl)phenoxy]propyl]ethanediimidamide;trihydrochloride Chemical compound Cl.Cl.Cl.NC(=N)C(=N)NCCCOC1=CC=CC(CN2CCCC2)=C1 KULYHDQCRCSIHF-UHFFFAOYSA-N 0.000 description 2
- GSKUHCYANQAPDQ-UHFFFAOYSA-N 3-n-[2-[[5-[(dimethylamino)methyl]-4-methylthiophen-2-yl]methylsulfanyl]ethyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound CC1=C(CN(C)C)SC(CSCCNC=2C(=NSN=2)N)=C1 GSKUHCYANQAPDQ-UHFFFAOYSA-N 0.000 description 2
- XLMCTHGDIZFBND-UHFFFAOYSA-N 3-n-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound O1C(CN(C)C)=CC=C1CSCCNC1=NSN=C1N XLMCTHGDIZFBND-UHFFFAOYSA-N 0.000 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 description 2
- FTQNYNLEKXCHPJ-UHFFFAOYSA-N 3-n-[3-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound NC1=NSN=C1NCCCOC1=CC(CN2CCCCC2)=CC=N1 FTQNYNLEKXCHPJ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 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 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 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 206010065713 Gastric Fistula Diseases 0.000 description 2
- 244000018764 Nyssa sylvatica Species 0.000 description 2
- 235000003339 Nyssa sylvatica Nutrition 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 230000001262 anti-secretory effect Effects 0.000 description 2
- 230000001746 atrial effect Effects 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 231100000673 dose–response relationship Toxicity 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
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen 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
- 230000003389 potentiating effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 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
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 1
- ARWHGIMAJQSHHF-UHFFFAOYSA-N 1-oxo-3-n-[2-[[5-(piperidin-1-ylmethyl)thiophen-3-yl]methylsulfanyl]ethyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound NC1=NS(=O)N=C1NCCSCC1=CSC(CN2CCCCC2)=C1 ARWHGIMAJQSHHF-UHFFFAOYSA-N 0.000 description 1
- XSZQYVCYBUOSGN-UHFFFAOYSA-N 1-oxo-4-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-3-n-(pyridin-3-ylmethyl)-1,2,5-thiadiazole-3,4-diamine Chemical compound C=1C=CN=CC=1CNC1=NS(=O)N=C1NCCCOC(C=1)=CC=CC=1CN1CCCCC1 XSZQYVCYBUOSGN-UHFFFAOYSA-N 0.000 description 1
- NMNIHVKUIGROBN-UHFFFAOYSA-N 1-oxo-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-4-prop-2-ynyl-1,2,5-thiadiazol-3-amine Chemical compound O=S1N=C(CC#C)C(NCCCOC=2C=C(CN3CCCCC3)C=CC=2)=N1 NMNIHVKUIGROBN-UHFFFAOYSA-N 0.000 description 1
- LSZMVESSGLHDJE-UHFFFAOYSA-N 2-bromo-4-methylpyridine Chemical compound 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
- VIXAHDGOLUBBGH-UHFFFAOYSA-N 2-n'-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]ethanediimidamide;hydrate;trihydrochloride Chemical compound O.Cl.Cl.Cl.CN(C)CC1=CC=C(CSCCNC(=N)C(N)=N)O1 VIXAHDGOLUBBGH-UHFFFAOYSA-N 0.000 description 1
- QNBGBDWGSPDKEE-UHFFFAOYSA-N 2-n'-[3-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropyl]ethanediimidamide;trihydrochloride Chemical compound Cl.Cl.Cl.C1=NC(OCCCNC(=N)C(=N)N)=CC(CN2CCCCC2)=C1 QNBGBDWGSPDKEE-UHFFFAOYSA-N 0.000 description 1
- GXUPWFDCTMTLFJ-UHFFFAOYSA-N 2-n'-benzyl-1-n'-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]ethanediimidamide;trihydrochloride Chemical compound Cl.Cl.Cl.C=1C=CC=CC=1CN=C(N)C(N)=NCCCOC(C=1)=CC=CC=1CN1CCCCC1 GXUPWFDCTMTLFJ-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
- HCBVAPDYYRYBBB-UHFFFAOYSA-N 3-n-[2-[[5-(piperidin-1-ylmethyl)thiophen-3-yl]methylsulfanyl]ethyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound NC1=NSN=C1NCCSCC1=CSC(CN2CCCCC2)=C1 HCBVAPDYYRYBBB-UHFFFAOYSA-N 0.000 description 1
- RPQYDOLJIJTBMC-UHFFFAOYSA-N 3-n-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1-oxo-1,2,5-thiadiazole-3,4-diamine Chemical compound CN(C)CC1=CC=CC(OCCCNC=2C(=NS(=O)N=2)N)=C1 RPQYDOLJIJTBMC-UHFFFAOYSA-N 0.000 description 1
- CWVKQJBALYEZMX-UHFFFAOYSA-N 3-n-[3-[5-[(dimethylamino)methyl]thiophen-3-yl]oxypropyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound S1C(CN(C)C)=CC(OCCCNC=2C(=NSN=2)N)=C1 CWVKQJBALYEZMX-UHFFFAOYSA-N 0.000 description 1
- NBGRTVUJNQQBDR-UHFFFAOYSA-N 3-n-[3-[5-[(dimethylamino)methyl]thiophen-3-yl]oxypropyl]-1-oxo-1,2,5-thiadiazole-3,4-diamine Chemical compound S1C(CN(C)C)=CC(OCCCNC=2C(=NS(=O)N=2)N)=C1 NBGRTVUJNQQBDR-UHFFFAOYSA-N 0.000 description 1
- VBJIUTXAZRATMG-UHFFFAOYSA-N 3-n-benzyl-1-oxo-4-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1,2,5-thiadiazole-3,4-diamine Chemical compound C=1C=CC=CC=1CNC1=NS(=O)N=C1NCCCOC(C=1)=CC=CC=1CN1CCCCC1 VBJIUTXAZRATMG-UHFFFAOYSA-N 0.000 description 1
- VIZLYBIHFICMNL-UHFFFAOYSA-N 4-ethyl-1,2,5-thiadiazol-3-amine Chemical compound CCC1=NSN=C1N VIZLYBIHFICMNL-UHFFFAOYSA-N 0.000 description 1
- QJJUBBIDUFLMJA-UHFFFAOYSA-N 4-n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-3-n-(pyridin-3-ylmethyl)-1,2,5-thiadiazole-3,4-diamine Chemical compound C=1C=CC(CN2CCCCC2)=CC=1OCCCNC1=NSN=C1NCC1=CC=CN=C1 QJJUBBIDUFLMJA-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- WXCGZHJWZWMSFQ-UHFFFAOYSA-N CCNC=1C=NS(=O)N=1 Chemical compound CCNC=1C=NS(=O)N=1 WXCGZHJWZWMSFQ-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- BCAKQOWRRNAMTL-UHFFFAOYSA-N NC1=NS(N=C1NCCCSC1=CC(=CC=C1)CN1CCCCC1)=O Chemical compound NC1=NS(N=C1NCCCSC1=CC(=CC=C1)CN1CCCCC1)=O BCAKQOWRRNAMTL-UHFFFAOYSA-N 0.000 description 1
- OAJHLVJVQKFHPB-UHFFFAOYSA-N O.Cl.Cl.Cl.C(C(N)=N)(N)=N Chemical compound O.Cl.Cl.Cl.C(C(N)=N)(N)=N OAJHLVJVQKFHPB-UHFFFAOYSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RDJGIQPSSNMJPF-UHFFFAOYSA-N ethanediimidamide Chemical class NC(=N)C(N)=N RDJGIQPSSNMJPF-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
- 239000006260 foam Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000003736 gastrointestinal content Anatomy 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 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
- 238000002513 implantation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- HPQIDJKQMFOBKA-UHFFFAOYSA-N n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-4-prop-2-ynyl-1,2,5-thiadiazol-3-amine Chemical compound C#CCC1=NSN=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 HPQIDJKQMFOBKA-UHFFFAOYSA-N 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 229940098466 sublingual tablet Drugs 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000005406 washing 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36320782A | 1982-03-29 | 1982-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS250229B2 true CS250229B2 (en) | 1987-04-16 |
Family
ID=23429274
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS832191A CS250229B2 (en) | 1982-03-29 | 1983-03-29 | Method of 3,4-diamino-1,2,5-thiadiazole derivatives' production |
| CS841958A CS250240B2 (en) | 1982-03-29 | 1983-03-29 | Method of ethandiimidamide's derivatives production |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS841958A CS250240B2 (en) | 1982-03-29 | 1983-03-29 | Method of ethandiimidamide's derivatives production |
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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