FI79527C - Foerfarande foer framstaellning av nya antiarytmiska aminoguanidinderivat. - Google Patents
Foerfarande foer framstaellning av nya antiarytmiska aminoguanidinderivat. Download PDFInfo
- Publication number
- FI79527C FI79527C FI844909A FI844909A FI79527C FI 79527 C FI79527 C FI 79527C FI 844909 A FI844909 A FI 844909A FI 844909 A FI844909 A FI 844909A FI 79527 C FI79527 C FI 79527C
- Authority
- FI
- Finland
- Prior art keywords
- general formula
- group
- carbon atoms
- atom
- acid addition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 230000003288 anthiarrhythmic effect Effects 0.000 title claims description 9
- 239000003416 antiarrhythmic agent Substances 0.000 title claims description 6
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical class NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- -1 hydroxyethyl groups Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000002541 isothioureas Chemical class 0.000 claims description 5
- 150000004031 phenylhydrazines Chemical class 0.000 claims description 5
- 150000001912 cyanamides Chemical class 0.000 claims description 4
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 238000011144 upstream manufacturing Methods 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 206010003119 arrhythmia Diseases 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 230000006793 arrhythmia Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VLPIATFUUWWMKC-SNVBAGLBSA-N (2r)-1-(2,6-dimethylphenoxy)propan-2-amine Chemical compound C[C@@H](N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-SNVBAGLBSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 206010061592 cardiac fibrillation Diseases 0.000 description 4
- 230000002600 fibrillogenic effect Effects 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229960003404 mexiletine Drugs 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 3
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940039750 aconitine Drugs 0.000 description 3
- STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 230000003533 narcotic effect Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- OUGYRPYTLIZMRE-UHFFFAOYSA-N 1,1-dimethyl-2-(2-methylanilino)guanidine;hydrochloride Chemical compound Cl.CN(C)C(\N)=N\NC1=CC=CC=C1C OUGYRPYTLIZMRE-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001800 adrenalinergic effect Effects 0.000 description 2
- 230000002763 arrhythmic effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 208000006218 bradycardia Diseases 0.000 description 2
- 230000036471 bradycardia Effects 0.000 description 2
- 230000003293 cardioprotective effect Effects 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- NFEIBWMZVIVJLQ-UHFFFAOYSA-N mexiletine hydrochloride Chemical compound [Cl-].CC([NH3+])COC1=C(C)C=CC=C1C NFEIBWMZVIVJLQ-UHFFFAOYSA-N 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
- 210000005241 right ventricle Anatomy 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- IDTWYHVEGJBGPT-UHFFFAOYSA-N (2,6-dichlorophenyl)hydrazine Chemical compound NNC1=C(Cl)C=CC=C1Cl IDTWYHVEGJBGPT-UHFFFAOYSA-N 0.000 description 1
- GHGPIPTUDQZJJS-UHFFFAOYSA-N (2-chlorophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Cl GHGPIPTUDQZJJS-UHFFFAOYSA-N 0.000 description 1
- KJGFNDCSTWGUDT-UHFFFAOYSA-N (2-methylanilino)azanium;chloride Chemical compound Cl.CC1=CC=CC=C1NN KJGFNDCSTWGUDT-UHFFFAOYSA-N 0.000 description 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
- OGZKHAGLXOMKOS-UHFFFAOYSA-N 2,6-dimethylmorpholine-4-carbonitrile Chemical compound CC1CN(C#N)CC(C)O1 OGZKHAGLXOMKOS-UHFFFAOYSA-N 0.000 description 1
- BJEXWFRASFTKNJ-UHFFFAOYSA-N 2-anilinoguanidine Chemical class NC(=N)NNC1=CC=CC=C1 BJEXWFRASFTKNJ-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 1
- IRBUJENWPDKMMR-UHFFFAOYSA-N 3-methylpiperidine-1-carbonitrile Chemical compound CC1CCCN(C#N)C1 IRBUJENWPDKMMR-UHFFFAOYSA-N 0.000 description 1
- MHRSBMTWXUWUQO-UHFFFAOYSA-N 4-(2-hydroxyethyl)piperazine-1-carbonitrile Chemical compound OCCN1CCN(C#N)CC1 MHRSBMTWXUWUQO-UHFFFAOYSA-N 0.000 description 1
- KMVPXBDOWDXXEN-UHFFFAOYSA-N 4-nitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1 KMVPXBDOWDXXEN-UHFFFAOYSA-N 0.000 description 1
- 206010003671 Atrioventricular Block Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 208000010271 Heart Block Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 101710198277 RNA polymerase sigma factor sigA Proteins 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 210000003403 autonomic nervous system Anatomy 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- CMIGYELBZZWTBE-UHFFFAOYSA-N azepane-1-carbonitrile Chemical compound N#CN1CCCCCC1 CMIGYELBZZWTBE-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- CRVGKGJPQYZRPT-UHFFFAOYSA-N diethylamino acetate Chemical compound CCN(CC)OC(C)=O CRVGKGJPQYZRPT-UHFFFAOYSA-N 0.000 description 1
- ZZTSQZQUWBFTAT-UHFFFAOYSA-N diethylcyanamide Chemical compound CCN(CC)C#N ZZTSQZQUWBFTAT-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- LFXAECSQJSRSTP-UHFFFAOYSA-N hydron;methyl carbamimidothioate;iodide Chemical compound I.CSC(N)=N LFXAECSQJSRSTP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- CQROVVJXIYLISJ-UHFFFAOYSA-N methyl n,n,n'-trimethylcarbamimidothioate Chemical compound CSC(=NC)N(C)C CQROVVJXIYLISJ-UHFFFAOYSA-N 0.000 description 1
- IXIIRPJUCUIORZ-UHFFFAOYSA-N methyl n,n-diethylcarbamimidothioate Chemical compound CCN(CC)C(=N)SC IXIIRPJUCUIORZ-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000002445 parasympatholytic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- NVPICXQHSYQKGM-UHFFFAOYSA-N piperidine-1-carbonitrile Chemical compound N#CN1CCCCC1 NVPICXQHSYQKGM-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- QJRYYOWARFCJQZ-UHFFFAOYSA-N pyrrolidine-1-carbonitrile Chemical compound N#CN1CCCC1 QJRYYOWARFCJQZ-UHFFFAOYSA-N 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000036279 refractory period Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
- C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
- C07C281/10—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being further bound to an acyclic carbon atom or to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU834222A HU190639B (en) | 1983-12-12 | 1983-12-12 | Process for production of new aminoguanidin derivatives |
| HU422283 | 1983-12-12 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI844909A0 FI844909A0 (fi) | 1984-12-12 |
| FI844909L FI844909L (fi) | 1985-06-13 |
| FI79527B FI79527B (fi) | 1989-09-29 |
| FI79527C true FI79527C (fi) | 1990-01-10 |
Family
ID=10967376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI844909A FI79527C (fi) | 1983-12-12 | 1984-12-12 | Foerfarande foer framstaellning av nya antiarytmiska aminoguanidinderivat. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4731383A (en:Method) |
| JP (1) | JPS60178855A (en:Method) |
| KR (1) | KR870001105B1 (en:Method) |
| AT (1) | AT394192B (en:Method) |
| BE (1) | BE901239A (en:Method) |
| BG (3) | BG44374A3 (en:Method) |
| CA (1) | CA1237129A (en:Method) |
| CH (1) | CH664955A5 (en:Method) |
| DD (1) | DD228246A5 (en:Method) |
| DE (1) | DE3445339A1 (en:Method) |
| DK (1) | DK164155C (en:Method) |
| FI (1) | FI79527C (en:Method) |
| FR (1) | FR2556343B1 (en:Method) |
| GB (1) | GB2151617B (en:Method) |
| HU (1) | HU190639B (en:Method) |
| IL (1) | IL73811A (en:Method) |
| NL (1) | NL193539C (en:Method) |
| NO (1) | NO159528C (en:Method) |
| PL (2) | PL140594B1 (en:Method) |
| SE (1) | SE462847B (en:Method) |
| SU (2) | SU1340583A3 (en:Method) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5612332A (en) * | 1984-03-19 | 1997-03-18 | Alteon Inc. | Di- and triaminoguanidines, and methods of use |
| US5852009A (en) * | 1984-03-19 | 1998-12-22 | The Rockefeller University | Compositions, including pharmaceutical compositions, for inhibiting the advanced glycosylation of proteins, and therapeutic methods based thereon |
| FR2669927B1 (fr) * | 1990-11-29 | 1994-04-08 | Adir Cie | Nouveaux derives de guanidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| ES2103166B1 (es) * | 1992-08-26 | 1998-04-01 | Ciba Geigy Ag | Procedimiento para la obtencion de amidinohidrazonas biciclicas. |
| US5424449A (en) * | 1994-10-28 | 1995-06-13 | Olin Corporation | Process for the preparation of 5-aminotetrazole |
| US5850840A (en) * | 1995-11-15 | 1998-12-22 | Alteon Inc. | Methods for measurement and treatment predicated on the presence of advanced glycosylation endproducts in tobacco and its combustion byproducts |
| US6110968A (en) * | 1995-12-26 | 2000-08-29 | The Picower Institute For Medical Research | Methods for treatment predicated on the presence of advanced glycosylation endproducts in tobacco and its combustion byproducts |
| US5877217A (en) * | 1995-12-26 | 1999-03-02 | Alteon Inc. | N-acylaminoalkyl-hydrazinecarboximidamides |
| AT405180B (de) * | 1997-04-01 | 1999-06-25 | Biochemie Gmbh | Neue derivate von substituierten 3-cephem-4-carbonsäurederivaten und verfahren zu deren herstellung |
| US6693095B2 (en) | 1997-04-01 | 2004-02-17 | Biochemie Gesellschaft M.B.H. | Antibacterial substituted 7-acylamino-3-(methylhydrazono) methyl-cephalosporins and intermediates |
| ES2203955T3 (es) * | 1997-04-01 | 2004-04-16 | Biochemie Gesellschaft M.B.H. | 7-acilamino-3-(metilhidrazono)metil-cefalosporinas sustituidas antibacterianas y productos intermedios. |
| FR2771409B1 (fr) * | 1997-11-21 | 2000-01-14 | Oreal | Nouveaux composes azoiques, utilisation pour la teinture, compositions les contenant et procedes de teinture |
| US6883592B2 (en) | 1998-11-04 | 2005-04-26 | Zalman Tech Co., Ltd. | Heatsink for electronic component |
| US7180758B2 (en) | 1999-07-22 | 2007-02-20 | Mks Instruments, Inc. | Class E amplifier with inductive clamp |
| FR2804428B1 (fr) * | 2000-01-27 | 2002-03-22 | Oreal | Nouvelles bases d'oxydation a chaine guanidine, leur procede de preparation, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture |
| ITRM20020625A1 (it) * | 2002-12-17 | 2004-06-18 | Sigma Tau Ind Farmaceuti | Derivati di guanidine variamente sostituite, loro uso come medicamenti ad attivita' antidiabetica e/o antiobesita'. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE663481A (en:Method) * | 1964-05-05 | |||
| GB1274668A (en) * | 1968-06-10 | 1972-05-17 | Ici Ltd | Pesticidal compositions comprising aminoguanidines |
| US3803324A (en) * | 1968-07-09 | 1974-04-09 | Boehringer Mannheim Gmbh | Amino-guanidine derivatives useful for regulating blood pressure |
| DE1768867C3 (de) * | 1968-07-09 | 1973-12-20 | Boehringer Mannheim Gmbh, 6800 Mannheim | Aminoguanidin-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Herstellung von Arzneimitteln |
| DE1939738A1 (de) * | 1969-08-05 | 1971-02-18 | Boehringer Mannheim Gmbh | Aminoguanidine und Verfahren zur Herstellung derselben |
| NL7315350A (nl) * | 1973-11-09 | 1975-05-13 | Akzo Nv | Nieuwe aminoguanidine verbindingen. |
-
1983
- 1983-12-12 HU HU834222A patent/HU190639B/hu not_active IP Right Cessation
-
1984
- 1984-12-07 CH CH5830/84A patent/CH664955A5/de not_active IP Right Cessation
- 1984-12-10 BE BE1/11150A patent/BE901239A/fr not_active IP Right Cessation
- 1984-12-11 AT AT0392384A patent/AT394192B/de not_active IP Right Cessation
- 1984-12-12 JP JP59260996A patent/JPS60178855A/ja active Granted
- 1984-12-12 PL PL1984250892A patent/PL140594B1/pl unknown
- 1984-12-12 CA CA000469862A patent/CA1237129A/en not_active Expired
- 1984-12-12 KR KR1019840007861A patent/KR870001105B1/ko not_active Expired
- 1984-12-12 FI FI844909A patent/FI79527C/fi not_active IP Right Cessation
- 1984-12-12 IL IL73811A patent/IL73811A/xx not_active IP Right Cessation
- 1984-12-12 SE SE8406302A patent/SE462847B/sv not_active IP Right Cessation
- 1984-12-12 BG BG076657A patent/BG44374A3/xx unknown
- 1984-12-12 DK DK595484A patent/DK164155C/da not_active IP Right Cessation
- 1984-12-12 SU SU843825601A patent/SU1340583A3/ru active
- 1984-12-12 NL NL8403779A patent/NL193539C/nl not_active IP Right Cessation
- 1984-12-12 PL PL1984255440A patent/PL142626B1/pl unknown
- 1984-12-12 DD DD84270673A patent/DD228246A5/de not_active IP Right Cessation
- 1984-12-12 DE DE19843445339 patent/DE3445339A1/de active Granted
- 1984-12-12 BG BG067888A patent/BG42355A3/xx unknown
- 1984-12-12 FR FR8418973A patent/FR2556343B1/fr not_active Expired
- 1984-12-12 NO NO844978A patent/NO159528C/no unknown
- 1984-12-12 GB GB08431312A patent/GB2151617B/en not_active Expired
-
1985
- 1985-10-28 SU SU853969348A patent/SU1498383A3/ru active
-
1986
- 1986-10-29 US US06/925,489 patent/US4731383A/en not_active Expired - Lifetime
-
1994
- 1994-02-08 BG BG098442A patent/BG60757B2/bg unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: BIOGAL GYOGYSZERGYAR RT. |