SU1419518A3 - Способ получени производных 1,2,5-тиадиазола или их нетоксичных фармацевтически приемлемых солей,гидратов или сольватов - Google Patents
Способ получени производных 1,2,5-тиадиазола или их нетоксичных фармацевтически приемлемых солей,гидратов или сольватов Download PDFInfo
- Publication number
- SU1419518A3 SU1419518A3 SU833568849A SU3568849A SU1419518A3 SU 1419518 A3 SU1419518 A3 SU 1419518A3 SU 833568849 A SU833568849 A SU 833568849A SU 3568849 A SU3568849 A SU 3568849A SU 1419518 A3 SU1419518 A3 SU 1419518A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- thiadiazole
- mmol
- product
- amino
- concentrated
- Prior art date
Links
- 239000012453 solvate Substances 0.000 title claims abstract description 13
- 150000003839 salts Chemical class 0.000 title claims abstract description 5
- 150000004677 hydrates Chemical class 0.000 title claims abstract description 4
- 231100000252 nontoxic Toxicity 0.000 title claims abstract description 4
- 230000003000 nontoxic effect Effects 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 13
- 150000004868 1,2,5-thiadiazoles Chemical class 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims description 2
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 7
- 239000012442 inert solvent Substances 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- RDJGIQPSSNMJPF-UHFFFAOYSA-N ethanediimidamide Chemical class NC(=N)C(N)=N RDJGIQPSSNMJPF-UHFFFAOYSA-N 0.000 abstract description 3
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 abstract 1
- 239000003699 antiulcer agent Substances 0.000 abstract 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000000047 product Substances 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 29
- -1 (3-Piperidinomethylphenoxy) propyl ethanediimidamide trihydrochloride Chemical compound 0.000 description 26
- 239000000203 mixture Substances 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 8
- 230000002496 gastric effect Effects 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 229940086542 triethylamine Drugs 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 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 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000003339 Nyssa sylvatica Nutrition 0.000 description 3
- 244000018764 Nyssa sylvatica Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000028327 secretion Effects 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 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
- RYWNBWWEACYLKY-UHFFFAOYSA-N 4-propyl-1,2,5-thiadiazol-3-amine Chemical compound CCCC1=NSN=C1N RYWNBWWEACYLKY-UHFFFAOYSA-N 0.000 description 2
- FABRNWMPZBUDLA-UHFFFAOYSA-N C(C(N)=N)(N(SC)CC)=N Chemical compound C(C(N)=N)(N(SC)CC)=N FABRNWMPZBUDLA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001262 anti-secretory effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- JKXCZYCVHPKTPK-UHFFFAOYSA-N hydrate;trihydrochloride Chemical compound O.Cl.Cl.Cl JKXCZYCVHPKTPK-UHFFFAOYSA-N 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 125000006308 propyl amino group Chemical group 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002627 tracheal intubation Methods 0.000 description 2
- ALOVQGMDXUFLEB-UHFFFAOYSA-N 1-oxo-1,2,5-thiadiazol-3-amine Chemical compound NC=1C=NS(=O)N=1 ALOVQGMDXUFLEB-UHFFFAOYSA-N 0.000 description 1
- MPSJEYKSORCYMH-UHFFFAOYSA-N 1-oxo-N-propyl-1,2,5-thiadiazol-3-amine Chemical compound C(CC)NC1=NS(N=C1)=O MPSJEYKSORCYMH-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
- QMEVABXAIUEULQ-UHFFFAOYSA-N 3-(3,6-dihydro-2H-pyridin-1-yl)-N-methyl-N-phenoxypropan-1-amine Chemical compound N1(CCC=CC1)CCCN(OC1=CC=CC=C1)C QMEVABXAIUEULQ-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
- QCHHKUYJOJEKBO-UHFFFAOYSA-N 3-[6-[(dimethylamino)methyl]pyridin-2-yl]oxypropan-1-amine Chemical compound CN(C)CC1=CC=CC(OCCCN)=N1 QCHHKUYJOJEKBO-UHFFFAOYSA-N 0.000 description 1
- 241000269420 Bufonidae Species 0.000 description 1
- NDJJUFHSJYZUFF-UHFFFAOYSA-N C(C(N)=N)(NCC)=N Chemical compound C(C(N)=N)(NCC)=N NDJJUFHSJYZUFF-UHFFFAOYSA-N 0.000 description 1
- GSTILCWVBXUZPU-UHFFFAOYSA-N CSC=1C(=NSN1)NCC Chemical compound CSC=1C(=NSN1)NCC GSTILCWVBXUZPU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010016717 Fistula Diseases 0.000 description 1
- 206010065713 Gastric Fistula Diseases 0.000 description 1
- 101000712982 Homo sapiens Ras association domain-containing protein 8 Proteins 0.000 description 1
- XQZGDJHYTIMLFH-UHFFFAOYSA-N N-ethyl-1,2,5-thiadiazol-3-amine Chemical compound C(C)NC1=NSN=C1 XQZGDJHYTIMLFH-UHFFFAOYSA-N 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100033218 Ras association domain-containing protein 8 Human genes 0.000 description 1
- MCRWZBYTLVCCJJ-DKALBXGISA-N [(1s,3r)-3-[[(3s,4s)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[(1s,4s)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)[C@@]1(C[C@@H](CC1)N[C@@H]1[C@@H](COCC1)OC)C(C)C)[H])N2C1=CC(C(F)(F)F)=NC=N1 MCRWZBYTLVCCJJ-DKALBXGISA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000010276 construction 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
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- JWOSTXBESVWMJW-UHFFFAOYSA-N cyclohexyl sulfamate Chemical class NS(=O)(=O)OC1CCCCC1 JWOSTXBESVWMJW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000003890 fistula Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- AHKHXHNFVGUCBC-UHFFFAOYSA-N n-propyl-1,2,5-thiadiazol-3-amine Chemical compound CCCNC=1C=NSN=1 AHKHXHNFVGUCBC-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 238000000554 physical therapy Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N propyl ethylene Natural products CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 102200105730 rs16846624 Human genes 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004448 titration 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (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 |
|---|---|
| SU1419518A3 true SU1419518A3 (ru) | 1988-08-23 |
Family
ID=23429274
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833568849A SU1419518A3 (ru) | 1982-03-29 | 1983-03-28 | Способ получени производных 1,2,5-тиадиазола или их нетоксичных фармацевтически приемлемых солей,гидратов или сольватов |
| SU843750493A SU1355123A3 (ru) | 1982-03-29 | 1984-06-08 | Способ получени замещенного этандиимидамина или его фармацевтически приемлемых солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU843750493A SU1355123A3 (ru) | 1982-03-29 | 1984-06-08 | Способ получени замещенного этандиимидамина или его фармацевтически приемлемых солей |
Country Status (30)
| Country | Link |
|---|---|
| JP (2) | JPS58180477A (enExample) |
| KR (1) | KR880002209B1 (enExample) |
| AT (1) | AT386599B (enExample) |
| AU (2) | AU557577B2 (enExample) |
| BE (1) | BE896291A (enExample) |
| CH (2) | CH660880A5 (enExample) |
| CS (2) | CS250240B2 (enExample) |
| DD (2) | DD219768A5 (enExample) |
| DE (1) | DE3311281A1 (enExample) |
| DK (2) | DK166677B1 (enExample) |
| ES (3) | ES520982A0 (enExample) |
| FR (2) | FR2542741B1 (enExample) |
| GB (2) | GB2117769B (enExample) |
| GR (1) | GR78524B (enExample) |
| HU (2) | HU196386B (enExample) |
| IE (1) | IE55596B1 (enExample) |
| IL (1) | IL68259A0 (enExample) |
| IT (1) | IT1164633B (enExample) |
| LU (1) | LU84716A1 (enExample) |
| MY (1) | MY8700942A (enExample) |
| NL (1) | NL8301063A (enExample) |
| NO (1) | NO163055C (enExample) |
| NZ (1) | NZ203726A (enExample) |
| OA (1) | OA07356A (enExample) |
| PT (1) | PT76459B (enExample) |
| SE (2) | SE461040B (enExample) |
| SU (2) | SU1419518A3 (enExample) |
| YU (1) | YU44849B (enExample) |
| ZA (1) | ZA832154B (enExample) |
| ZW (1) | ZW7683A1 (enExample) |
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 |
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (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 ZW ZW76/83A patent/ZW7683A1/xx unknown
- 1983-03-25 ZA ZA832154A patent/ZA832154B/xx unknown
- 1983-03-25 NL NL8301063A patent/NL8301063A/nl not_active Application Discontinuation
- 1983-03-25 ES ES520982A patent/ES520982A0/es active Granted
- 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 DE DE19833311281 patent/DE3311281A1/de not_active Withdrawn
- 1983-03-28 NO NO831100A patent/NO163055C/no unknown
- 1983-03-28 NZ NZ203726A patent/NZ203726A/en unknown
- 1983-03-28 AU AU12907/83A patent/AU557577B2/en not_active Ceased
- 1983-03-28 GB GB08308518A patent/GB2117769B/en not_active Expired
- 1983-03-28 BE BE0/210417A patent/BE896291A/fr not_active IP Right Cessation
- 1983-03-28 GR GR70903A patent/GR78524B/el unknown
- 1983-03-28 SE SE8301725A patent/SE461040B/sv not_active IP Right Cessation
- 1983-03-28 DK DK141383A patent/DK166677B1/da not_active IP Right Cessation
- 1983-03-28 HU HU854071A patent/HU196386B/hu not_active IP Right Cessation
- 1983-03-28 IE IE686/83A patent/IE55596B1/en not_active IP Right Cessation
- 1983-03-28 IL IL68259A patent/IL68259A0/xx not_active IP Right Cessation
- 1983-03-28 LU LU84716A patent/LU84716A1/fr unknown
- 1983-03-28 SU SU833568849A patent/SU1419518A3/ru active
- 1983-03-28 HU HU831040A patent/HU188742B/hu not_active IP Right Cessation
- 1983-03-29 AT AT0111083A patent/AT386599B/de not_active IP Right Cessation
- 1983-03-29 OA OA57955A patent/OA07356A/xx unknown
- 1983-03-29 CS CS841958A patent/CS250240B2/cs unknown
- 1983-03-29 JP JP58051740A patent/JPS58180477A/ja active Granted
- 1983-03-29 CH CH575/86A patent/CH660880A5/de not_active IP Right Cessation
- 1983-03-29 YU YU744/83A patent/YU44849B/xx unknown
- 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
- 1983-03-29 KR KR1019830001283A patent/KR880002209B1/ko not_active Expired
- 1983-03-29 CS CS832191A patent/CS250229B2/cs unknown
- 1983-03-29 CH CH1749/83A patent/CH655111A5/de not_active IP Right Cessation
- 1983-11-30 ES ES527686A patent/ES527686A0/es active Granted
- 1983-11-30 ES ES527685A patent/ES527685A0/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 DK081192A patent/DK81192A/da not_active Application Discontinuation
-
1993
- 1993-04-16 JP JP5124585A patent/JPH06135925A/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| Патент GB № 2067987, кл. С 07 D 285/10, 1981. * |
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