SU465784A3 - Способ получени замещенных бигуанида - Google Patents

Способ получени замещенных бигуанида

Info

Publication number: SU465784A3
Authority: SU; USSR - Soviet Union
Prior art keywords: theoretical; compound; yield; methyl; nitrate
Prior art date: 1971-04-02

Application number

SU1907665A

Other languages

English (en)

Russian (ru)

Inventor

Руфер Клеменс (Австрия)

Аренс Ханнс (Фрг)

Бире Хельмут (Фрг)

Шредер Эберхард (Фрг)

Лозерт Вольфганг (Фрг)

Логе Олаф (Фрг)

Щиллингер Эккерхард (Фрг)

Original Assignee

Шеринг Аг (Фирма)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1971-04-02

Filing date

1972-03-31

Publication date

1975-03-30

1972-03-31 Application filed by Шеринг Аг (Фирма) filed Critical Шеринг Аг (Фирма)

1975-03-30 Application granted granted Critical

1975-03-30 Publication of SU465784A3 publication Critical patent/SU465784A3/ru

Links

229940123208 Biguanide Drugs 0.000 title description 4
150000004283 biguanides Chemical class 0.000 title description 3
238000004519 manufacturing process Methods 0.000 title 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 105
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
150000001875 compounds Chemical class 0.000 description 57
229910002651 NO3 Inorganic materials 0.000 description 20
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 17
-1 slot metafunction Chemical compound 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
DJAVXQJRIAKWOA-UHFFFAOYSA-N carbonic acid;1-(diaminomethylidene)-3-methylthiourea Chemical compound OC(O)=O.CNC(=S)NC(N)=N DJAVXQJRIAKWOA-UHFFFAOYSA-N 0.000 description 9
150000003839 salts Chemical class 0.000 description 8
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 7
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
SPLJCDGYZTYQQY-UHFFFAOYSA-N 1-(diaminomethylidene)-3-methylthiourea Chemical compound CNC(=S)NC(N)=N SPLJCDGYZTYQQY-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 4
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
239000012458 free base Substances 0.000 description 4
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
229910001961 silver nitrate Inorganic materials 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
150000001412 amines Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229930195734 saturated hydrocarbon Natural products 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
LPXNRJGSIDFGGQ-UHFFFAOYSA-N 1-(diaminomethylidene)-3-propylthiourea Chemical compound CCCNC(=S)N=C(N)N LPXNRJGSIDFGGQ-UHFFFAOYSA-N 0.000 description 2
FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 description 2
UHEZLJYVTUWEOM-UHFFFAOYSA-N 1-butyl-3-(diaminomethylidene)thiourea;carbonic acid Chemical compound OC(O)=O.CCCCNC(=S)NC(N)=N UHEZLJYVTUWEOM-UHFFFAOYSA-N 0.000 description 2
KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 2
VJROPLWGFCORRM-UHFFFAOYSA-N 2-methylbutan-1-amine Chemical compound CCC(C)CN VJROPLWGFCORRM-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
FJMAIXOJSFLKEM-UHFFFAOYSA-N carbonic acid;1-(diaminomethylidene)-3-ethylthiourea Chemical compound OC(O)=O.CCNC(=S)NC(N)=N FJMAIXOJSFLKEM-UHFFFAOYSA-N 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 2
XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229940117803 phenethylamine Drugs 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229910052709 silver Inorganic materials 0.000 description 2
239000004332 silver Substances 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
CYHGQLSSEBEAAN-UHFFFAOYSA-N 1-(3-butoxypropyl)-3-(diaminomethylidene)-2-methylguanidine;nitric acid Chemical compound O[N+]([O-])=O.CCCCOCCCN=C(NC)NC(N)=N CYHGQLSSEBEAAN-UHFFFAOYSA-N 0.000 description 1
RFGZUHZWZHJFGF-UHFFFAOYSA-N 1-(diaminomethylidene)-2,3-dipropylguanidine;nitric acid Chemical compound O[N+]([O-])=O.CCCNC(NC(N)=N)=NCCC RFGZUHZWZHJFGF-UHFFFAOYSA-N 0.000 description 1
RUOMMWMBRTWTRW-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(1,1-diethoxybutyl)guanidine Chemical compound CCCC(OCC)(OCC)\N=C(/N)N=C(N)N RUOMMWMBRTWTRW-UHFFFAOYSA-N 0.000 description 1
YWPWIKITYUPSIY-UHFFFAOYSA-N 1-(diaminomethylidene)-2-methyl-3-pentylguanidine;hydrochloride Chemical compound Cl.CCCCCNC(=NC)N=C(N)N YWPWIKITYUPSIY-UHFFFAOYSA-N 0.000 description 1
MYLLYXIGHHQHDG-UHFFFAOYSA-N 1-(diaminomethylidene)-3-ethyl-2-(2,2,2-trifluoroethyl)guanidine;hydrochloride Chemical compound Cl.CCNC(NC(N)=N)=NCC(F)(F)F MYLLYXIGHHQHDG-UHFFFAOYSA-N 0.000 description 1
JJEDMQKJOVKGSX-UHFFFAOYSA-N 1-(diaminomethylidene)-3-ethyl-2-hexylguanidine;hydrochloride Chemical compound Cl.CCCCCCN=C(NCC)N=C(N)N JJEDMQKJOVKGSX-UHFFFAOYSA-N 0.000 description 1
UAJWDGACDQVTAI-UHFFFAOYSA-N 1-(diaminomethylidene)-3-ethyl-2-pentylguanidine;hydrochloride Chemical compound Cl.CCCCCN=C(NCC)N=C(N)N UAJWDGACDQVTAI-UHFFFAOYSA-N 0.000 description 1
VBWLMIYYNSQZBZ-UHFFFAOYSA-N 1-(diaminomethylidene)-3-hexyl-2-methylguanidine;hydrochloride Chemical compound Cl.CCCCCCNC(=NC)N=C(N)N VBWLMIYYNSQZBZ-UHFFFAOYSA-N 0.000 description 1
MXTQLUARQASURH-UHFFFAOYSA-N 1-(diaminomethylidene)-3-propan-2-yl-2-propylguanidine;nitric acid Chemical compound O[N+]([O-])=O.CCCNC(NC(N)=N)=NC(C)C MXTQLUARQASURH-UHFFFAOYSA-N 0.000 description 1
AVWOEAVWVDLXMA-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;nitric acid Chemical compound O[N+]([O-])=O.NC(N)=NC(N)=N AVWOEAVWVDLXMA-UHFFFAOYSA-N 0.000 description 1
OTWSADYAOIFPEN-UHFFFAOYSA-N 1-butoxy-3-(diaminomethylidene)-2-ethylguanidine;nitric acid Chemical compound O[N+]([O-])=O.CCCCON=C(NCC)NC(N)=N OTWSADYAOIFPEN-UHFFFAOYSA-N 0.000 description 1
QUMDOYVMQMITEA-UHFFFAOYSA-N 1-butyl-3-(diaminomethylidene)-2-methylguanidine;hydrochloride Chemical compound Cl.CCCCNC(=NC)N=C(N)N QUMDOYVMQMITEA-UHFFFAOYSA-N 0.000 description 1
HARNPCRWNNJYMS-UHFFFAOYSA-N 1-cyclopentyl-3-(diaminomethylidene)-2-ethylguanidine;nitric acid Chemical compound O[N+]([O-])=O.CCN=C(N=C(N)N)NC1CCCC1 HARNPCRWNNJYMS-UHFFFAOYSA-N 0.000 description 1
XZYJNHZNHGUSNY-UHFFFAOYSA-N 2,2,2-trifluoro-n-methylethanamine Chemical compound CNCC(F)(F)F XZYJNHZNHGUSNY-UHFFFAOYSA-N 0.000 description 1
WBGBQSRNXPVFDB-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutan-1-amine Chemical compound NCC(F)(F)C(F)(F)C(F)(F)F WBGBQSRNXPVFDB-UHFFFAOYSA-N 0.000 description 1
HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 1
KGKMETLQCMSQNT-UHFFFAOYSA-N 2-butyl-1-(diaminomethylidene)-3-ethylguanidine;hydrochloride Chemical compound Cl.CCCCN=C(NCC)N=C(N)N KGKMETLQCMSQNT-UHFFFAOYSA-N 0.000 description 1
BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 1
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
KPNJYXKRHWAPHP-UHFFFAOYSA-N 2-methylpentan-2-amine Chemical compound CCCC(C)(C)N KPNJYXKRHWAPHP-UHFFFAOYSA-N 0.000 description 1
LPUBRQWGZPPVBS-UHFFFAOYSA-N 3-butoxypropan-1-amine Chemical compound CCCCOCCCN LPUBRQWGZPPVBS-UHFFFAOYSA-N 0.000 description 1
FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
VPRIGCVCJPKVFZ-UHFFFAOYSA-N 4-chloro-n-phenylaniline Chemical compound C1=CC(Cl)=CC=C1NC1=CC=CC=C1 VPRIGCVCJPKVFZ-UHFFFAOYSA-N 0.000 description 1
UVOBODVSFRKUQX-UHFFFAOYSA-N 6-methoxyhexan-1-amine Chemical compound COCCCCCCN UVOBODVSFRKUQX-UHFFFAOYSA-N 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
229910052946 acanthite Inorganic materials 0.000 description 1
CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 1
FKCBLVCOSCZFHV-UHFFFAOYSA-N acetonitrile;ethanol Chemical compound CCO.CC#N FKCBLVCOSCZFHV-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000004855 amber Substances 0.000 description 1
229960004111 buformin Drugs 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
VVSVSDQFUZWMHE-UHFFFAOYSA-N carbonic acid;1-(diaminomethylidene)-3-propylthiourea Chemical compound OC(O)=O.CCCNC(=S)NC(N)=N VVSVSDQFUZWMHE-UHFFFAOYSA-N 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Chemical group 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
WCVVIGQKJZLJDB-UHFFFAOYSA-N o-butylhydroxylamine Chemical compound CCCCON WCVVIGQKJZLJDB-UHFFFAOYSA-N 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
XUARKZBEFFVFRG-UHFFFAOYSA-N silver sulfide Chemical compound [S-2].[Ag+].[Ag+] XUARKZBEFFVFRG-UHFFFAOYSA-N 0.000 description 1
229940056910 silver sulfide Drugs 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
VOXVCYMHFQQEMC-UHFFFAOYSA-O triethylazanium;nitrate Chemical compound [O-][N+]([O-])=O.CC[NH+](CC)CC VOXVCYMHFQQEMC-UHFFFAOYSA-O 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C1/00—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design
- A61C1/02—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design characterised by the drive of the dental tools
- A61C1/05—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design characterised by the drive of the dental tools with turbine drive
- A61C1/057—Dental machines for boring or cutting ; General features of dental machines or apparatus, e.g. hand-piece design characterised by the drive of the dental tools with turbine drive with means for preventing suction effect in turbine after deactivation of the drive air

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Dentistry (AREA)
Oral & Maxillofacial Surgery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SU1907665A 1971-04-02 1972-03-31 Способ получени замещенных бигуанида SU465784A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19712117015 DE2117015A1 (de)	1971-04-02	1971-04-02	1,2-Biguanide

Publications (1)

Publication Number	Publication Date
SU465784A3 true SU465784A3 (ru)	1975-03-30

Family

ID=5804148

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
SU1907665A SU465784A3 (ru)	1971-04-02	1972-03-31	Способ получени замещенных бигуанида
SU1907667A SU472501A3 (ru)	1971-04-02	1972-03-31	Способ получени замещенных бигуанида
SU1907668A SU493959A3 (ru)	1971-04-02	1972-03-31	Способ получени 1,2-бигуанидов
SU1767915A SU535903A3 (ru)	1971-04-02	1972-03-31	Способ получени замещенных бигуанидов

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
SU1907667A SU472501A3 (ru)	1971-04-02	1972-03-31	Способ получени замещенных бигуанида
SU1907668A SU493959A3 (ru)	1971-04-02	1972-03-31	Способ получени 1,2-бигуанидов
SU1767915A SU535903A3 (ru)	1971-04-02	1972-03-31	Способ получени замещенных бигуанидов

Country Status (19)

Country	Link
AR (3)	AR194360A1 (2)
AT (4)	AT321318B (2)
AU (1)	AU468307B2 (2)
BE (1)	BE781590A (2)
CA (1)	CA988084A (2)
CH (1)	CH579534A5 (2)
CS (3)	CS161936B2 (2)
DD (1)	DD95228A5 (2)
DE (1)	DE2117015A1 (2)
DK (1)	DK129651B (2)
ES (1)	ES401124A1 (2)
FR (1)	FR2132396B1 (2)
GB (1)	GB1386130A (2)
HU (1)	HU162902B (2)
NL (1)	NL7204493A (2)
NO (1)	NO135418C (2)
SE (1)	SE377332B (2)
SU (4)	SU465784A3 (2)
ZA (1)	ZA722183B (2)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102008007314A1 (de)	2008-02-02	2009-08-06	Merck Patent Gmbh	Verfahren zur Herstellung von 3,6-Dihydro-1,3,5-triazinderivaten

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR940304A (fr) *	1946-01-07	1948-12-09	Ici Ltd	Procédé de fabrication de dérivés de biguanides

1971
- 1971-04-02 DE DE19712117015 patent/DE2117015A1/de not_active Withdrawn
1972
- 1972-03-15 CS CS6963*A patent/CS161936B2/cs unknown
- 1972-03-15 CS CS1724A patent/CS161935B2/cs unknown
- 1972-03-15 CS CS6964*A patent/CS161937B2/cs unknown
- 1972-03-22 DK DK134572AA patent/DK129651B/da unknown
- 1972-03-23 ES ES401124A patent/ES401124A1/es not_active Expired
- 1972-03-27 CH CH454672A patent/CH579534A5/xx not_active IP Right Cessation
- 1972-03-27 GB GB1416272A patent/GB1386130A/en not_active Expired
- 1972-03-29 SE SE7204127A patent/SE377332B/xx unknown
- 1972-03-29 AR AR241248A patent/AR194360A1/es active
- 1972-03-29 NO NO1084/72A patent/NO135418C/no unknown
- 1972-03-30 DD DD161938A patent/DD95228A5/xx unknown
- 1972-03-30 AT AT00786/73A patent/AT321318B/de not_active IP Right Cessation
- 1972-03-30 AU AU40661/72A patent/AU468307B2/en not_active Expired
- 1972-03-30 AT AT279272A patent/AT313301B/de not_active IP Right Cessation
- 1972-03-30 HU HUSC383A patent/HU162902B/hu unknown
- 1972-03-30 AT AT00785/73A patent/AT317240B/de not_active IP Right Cessation
- 1972-03-30 ZA ZA722183A patent/ZA722183B/xx unknown
- 1972-03-30 AT AT00784/73A patent/AT317239B/de not_active IP Right Cessation
- 1972-03-31 SU SU1907665A patent/SU465784A3/ru active
- 1972-03-31 BE BE781590A patent/BE781590A/xx unknown
- 1972-03-31 SU SU1907667A patent/SU472501A3/ru active
- 1972-03-31 SU SU1907668A patent/SU493959A3/ru active
- 1972-03-31 SU SU1767915A patent/SU535903A3/ru active
- 1972-04-04 FR FR7211727A patent/FR2132396B1/fr not_active Expired
- 1972-04-04 CA CA138,838A patent/CA988084A/en not_active Expired
- 1972-04-04 NL NL7204493A patent/NL7204493A/xx not_active Application Discontinuation
- 1972-11-13 AR AR245079A patent/AR194285A1/es active
- 1972-11-13 AR AR245080A patent/AR192485A1/es active

Also Published As

Publication number	Publication date
CS161935B2 (2)	1975-06-10
AT317239B (de)	1974-08-26
CS161937B2 (2)	1975-06-10
DE2117015A1 (de)	1972-10-26
CH579534A5 (2)	1976-09-15
NO135418C (2)	1977-04-05
FR2132396A1 (2)	1972-11-17
DK129651B (da)	1974-11-04
AT313301B (de)	1974-02-11
CA988084A (en)	1976-04-27
ZA722183B (en)	1972-12-27
NO135418B (2)	1976-12-27
BE781590A (fr)	1972-10-02
DD95228A5 (2)	1973-01-20
AT317240B (de)	1974-08-26
ES401124A1 (es)	1975-02-16
GB1386130A (en)	1975-03-05
HU162902B (2)	1973-04-28
SU472501A3 (ru)	1975-05-30
AR192485A1 (es)	1973-02-21
CS161936B2 (2)	1975-06-10
SU535903A3 (ru)	1976-11-15
DK129651C (2)	1975-04-07
AU4066172A (en)	1973-10-04
AU468307B2 (en)	1973-10-04
NL7204493A (2)	1972-10-04
SU493959A3 (ru)	1975-11-28
AT321318B (de)	1975-03-25
AR194285A1 (es)	1973-06-29
AR194360A1 (es)	1973-07-13
FR2132396B1 (2)	1975-10-10
SE377332B (2)	1975-06-30

Publication	Publication Date	Title
US4013678A (en)	1977-03-22	Process for preparing heterocyclicalkylthioalkyl-n-cyanoguanidines
US3960949A (en)	1976-06-01	1,2-Biguanides
US5001251A (en)	1991-03-19	Optical resolution of DL-3-acylthio-2-methylpropanoic acid
EP0452782B1 (en)	1997-01-15	Novel intermediates for preparing guanidine derivatives, their preparation and use
FI59991B (fi)	1981-07-31	Foerfarande foer framstaellning av 2-arylamino-2-imidazolin-derivat och deras salter
DE69626682T2 (de)	2003-11-06	Verfahren zur herstellung von guanidinderivaten, zwischenprodukte dafür und ihre herstellung
DE2429937C2 (2)	1988-01-28
JPS58150568A (ja)	1983-09-07	イミダゾ−ル誘導体の製法
SU465784A3 (ru)	1975-03-30	Способ получени замещенных бигуанида
US2543345A (en)	1951-02-27	Method of preparing glutamic acid amides
US4250316A (en)	1981-02-10	Pyridyl guanidine anti-ulcer agents
US4093621A (en)	1978-06-06	Process for preparing heterocyclicalkylthioalkyl-N-cyanoguanidines and thioureas
US3886171A (en)	1975-05-27	1-(benzamido)pyridinium salts
HU188074B (en)	1986-03-28	Process for the preparation of cimetidin
DE2429745A1 (de)	1975-01-23	Verfahren zur herstellung von triacetonamin
US4908454A (en)	1990-03-13	Process of producing guanidinothiazole derivatives
US3401201A (en)	1968-09-10	Imidocarbonates
US2527292A (en)	1950-10-24	Beta-nitroalkyl amines and methods of production of same
US4873343A (en)	1989-10-10	Process for the preparation of N-(2-chlorobenzyl)-2-(2-thienyl) ethylamine
US2501649A (en)	1950-03-21	Benzotriazole compound
DE862602C (de)	1953-01-12	Verfahren zur Herstellung von Halogendiamidinen und ihren Salzen
DE2916610C2 (de)	1986-04-03	Verfahren zur Herstellung von 1-Cyano-2-methyl-3-[2-[[(5-methyl-imidazol-4-yl)methyl]-thio]-äthyl]-guanidin
US4997981A (en)	1991-03-05	Processes for 2-(1-pentyl-3-guanidino)-4-(2-methyl-4-imidazolyl) thiazole and analogs
CH529766A (de)	1972-10-31	Verfahren zur Herstellung von Aryloxy-isoalkyl- 2-imidazolinen
US4171325A (en)	1979-10-16	Chemical process