DE1288591B - Verfahren zur Herstellung von Benzylguanidinen - Google Patents
Verfahren zur Herstellung von BenzylguanidinenInfo
- Publication number
- DE1288591B DE1288591B DEW29144A DEW0029144A DE1288591B DE 1288591 B DE1288591 B DE 1288591B DE W29144 A DEW29144 A DE W29144A DE W0029144 A DEW0029144 A DE W0029144A DE 1288591 B DE1288591 B DE 1288591B
- Authority
- DE
- Germany
- Prior art keywords
- ether
- solution
- carbon atoms
- hydrogen atom
- salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- ABSNGNUGFQIDDO-UHFFFAOYSA-N 2-benzylguanidine Chemical class NC(N)=NCC1=CC=CC=C1 ABSNGNUGFQIDDO-UHFFFAOYSA-N 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 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
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 150000001912 cyanamides Chemical class 0.000 claims description 2
- 150000002357 guanidines Chemical class 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- 239000000203 mixture Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 10
- ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- 229960003602 guanethidine Drugs 0.000 description 9
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- -1 p-toluene sulfone Chemical class 0.000 description 7
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
- 229960004980 betanidine Drugs 0.000 description 4
- NIVZHWNOUVJHKV-UHFFFAOYSA-N bethanidine Chemical compound CN\C(=N/C)NCC1=CC=CC=C1 NIVZHWNOUVJHKV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- AUIQUPQCYAEBKJ-UHFFFAOYSA-N methyl N-[(2-chlorophenyl)methyl]-N'-methylcarbamimidothioate hydroiodide Chemical compound I.ClC1=C(CNC(SC)=NC)C=CC=C1 AUIQUPQCYAEBKJ-UHFFFAOYSA-N 0.000 description 4
- 210000000826 nictitating membrane Anatomy 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- BBJUSJOGHYQDQX-WODDMCJRSA-N (2S)-4-[(E)-2-[(2S)-2-carboxy-5,6-dihydroxy-2,3-dihydroindol-1-yl]ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid Chemical compound OC(=O)[C@@H]1Cc2cc(O)c(O)cc2N1\C=C\C1=CC(=N[C@@H](C1)C(O)=O)C(O)=O BBJUSJOGHYQDQX-WODDMCJRSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- FPFIFCBPMJFKJR-LLVKDONJSA-M betanidin Natural products O=C([O-])[C+]1/[N+](=C/C=C/2\C=C(C(=O)O)N[C@@H](C(=O)O)C\2)/c2c(cc(O)c(O)c2)C1 FPFIFCBPMJFKJR-LLVKDONJSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002889 sympathetic effect Effects 0.000 description 3
- NOYASZMZIBFFNZ-UHFFFAOYSA-N (2-bromophenyl)methanamine Chemical compound NCC1=CC=CC=C1Br NOYASZMZIBFFNZ-UHFFFAOYSA-N 0.000 description 2
- PPQAPUVLIVDIBC-UHFFFAOYSA-N (2-bromophenyl)methylthiourea Chemical compound NC(=S)NCC1=CC=CC=C1Br PPQAPUVLIVDIBC-UHFFFAOYSA-N 0.000 description 2
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 2
- PZFIQSXNILACQZ-UHFFFAOYSA-N 1-bromo-2-(isothiocyanatomethyl)benzene Chemical compound BrC1=CC=CC=C1CN=C=S PZFIQSXNILACQZ-UHFFFAOYSA-N 0.000 description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000010339 dilation Effects 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- QOHPTTOYTZOONS-UHFFFAOYSA-N methanol;hydroiodide Chemical compound I.OC QOHPTTOYTZOONS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 230000001734 parasympathetic effect Effects 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
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- SJUKJZSTBBSGHF-UHFFFAOYSA-N (2,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1Cl SJUKJZSTBBSGHF-UHFFFAOYSA-N 0.000 description 1
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
- BZZXQZOBAUXLHZ-UHFFFAOYSA-N (c-methylsulfanylcarbonimidoyl)azanium;sulfate Chemical compound CSC(N)=N.CSC(N)=N.OS(O)(=O)=O BZZXQZOBAUXLHZ-UHFFFAOYSA-N 0.000 description 1
- DRDSBFMPPCZJOZ-UHFFFAOYSA-N 1,2-dimethyl-3-[(3-methylphenyl)methyl]guanidine Chemical compound CNC(NC)=NCC1=CC=CC(C)=C1 DRDSBFMPPCZJOZ-UHFFFAOYSA-N 0.000 description 1
- VIEXAFPVDSRNAY-UHFFFAOYSA-N 1,2-dimethylguanidine;sulfuric acid Chemical compound OS(O)(=O)=O.CNC(N)=NC VIEXAFPVDSRNAY-UHFFFAOYSA-N 0.000 description 1
- JTVBBONZVRUASR-UHFFFAOYSA-N 1-[(2-bromophenyl)methyl]-3-ethylthiourea Chemical compound BrC1=C(CNC(=S)NCC)C=CC=C1 JTVBBONZVRUASR-UHFFFAOYSA-N 0.000 description 1
- VZOUWOCYHIWPJB-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-2-methylguanidine Chemical compound CN=C(N)NCC1=CC=CC=C1Cl VZOUWOCYHIWPJB-UHFFFAOYSA-N 0.000 description 1
- ZUJKYGWKUGDFBM-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-3-ethyl-2-methylguanidine hydroiodide Chemical compound I.CCN\C(NCc1ccccc1Cl)=N/C ZUJKYGWKUGDFBM-UHFFFAOYSA-N 0.000 description 1
- BIBXHLPALSXTFQ-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-3-methylthiourea Chemical compound CNC(=S)NCC1=CC=CC=C1Cl BIBXHLPALSXTFQ-UHFFFAOYSA-N 0.000 description 1
- HKOSLXWSMJAOTH-UHFFFAOYSA-N 1-benzyl-2-methyl-3-propylguanidine Chemical compound CCCN\C(NCc1ccccc1)=N/C HKOSLXWSMJAOTH-UHFFFAOYSA-N 0.000 description 1
- RIXUXULYJVAPIX-UHFFFAOYSA-N 1-benzyl-3-ethylthiourea Chemical compound CCNC(=S)NCC1=CC=CC=C1 RIXUXULYJVAPIX-UHFFFAOYSA-N 0.000 description 1
- RMVDNJDSLXQPAV-UHFFFAOYSA-N 1-chloro-2-(isothiocyanatomethyl)benzene Chemical compound ClC1=CC=CC=C1CN=C=S RMVDNJDSLXQPAV-UHFFFAOYSA-N 0.000 description 1
- BGLDKTCKVCNWMR-UHFFFAOYSA-N 1-ethyl-2-methyl-3-[(2-methylphenyl)methyl]guanidine Chemical compound CCNC(NC)=NCC1=CC=CC=C1C BGLDKTCKVCNWMR-UHFFFAOYSA-N 0.000 description 1
- ONTSMPSZXNQOQI-UHFFFAOYSA-N 1-methyl-3-[(2-methylphenyl)methyl]thiourea Chemical compound CNC(=S)NCC1=CC=CC=C1C ONTSMPSZXNQOQI-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- MIZQCZHCPNSFBI-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)methyl]guanidine Chemical compound NC(N)=NCC1=CC=C(Cl)C=C1Cl MIZQCZHCPNSFBI-UHFFFAOYSA-N 0.000 description 1
- FLEFTYYJDDOXIG-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]-1,1-dimethylguanidine hydroiodide Chemical compound I.BrC1=C(CNC(=N)N(C)C)C=CC=C1 FLEFTYYJDDOXIG-UHFFFAOYSA-N 0.000 description 1
- VEWFHMVVHGDNPE-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]guanidine Chemical compound NC(N)=NCC1=CC=CC=C1Br VEWFHMVVHGDNPE-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000003098 Ganglion Cysts Diseases 0.000 description 1
- GNWINDNCYKDAGO-UHFFFAOYSA-N I.BrC1=C(CNC(SC)=N)C=CC=C1 Chemical compound I.BrC1=C(CNC(SC)=N)C=CC=C1 GNWINDNCYKDAGO-UHFFFAOYSA-N 0.000 description 1
- QBYISWVXHBHMDM-UHFFFAOYSA-N I.C(C1=CC=CC=C1)NC(SC)=NCC Chemical compound I.C(C1=CC=CC=C1)NC(SC)=NCC QBYISWVXHBHMDM-UHFFFAOYSA-N 0.000 description 1
- QAADZYUXQLUXFX-UHFFFAOYSA-N N-phenylmethylthioformamide Natural products S=CNCC1=CC=CC=C1 QAADZYUXQLUXFX-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
- OASQXHBBLDQMEI-UHFFFAOYSA-N S(=O)(=O)(O)O.BrC1=C(CNC(=N)N)C=CC=C1 Chemical compound S(=O)(=O)(O)O.BrC1=C(CNC(=N)N)C=CC=C1 OASQXHBBLDQMEI-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 208000005400 Synovial Cyst Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- UUDRLGYROXTISK-UHFFFAOYSA-N carbamimidoylazanium;iodide Chemical compound I.NC(N)=N UUDRLGYROXTISK-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- SLFLFNSLWZNOOG-UHFFFAOYSA-N ethanol;hydroiodide Chemical compound [I-].CC[OH2+] SLFLFNSLWZNOOG-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007774 longterm Effects 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- VPNXUHPKNCDPIK-UHFFFAOYSA-N methyl N'-methyl-N-[(2-methylphenyl)methyl]carbamimidothioate hydroiodide Chemical compound I.CSC(NCC1=C(C=CC=C1)C)=NC VPNXUHPKNCDPIK-UHFFFAOYSA-N 0.000 description 1
- KGGGDOUUGUNODJ-UHFFFAOYSA-N methyl n'-ethylcarbamimidothioate;hydroiodide Chemical compound I.CCNC(=N)SC KGGGDOUUGUNODJ-UHFFFAOYSA-N 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 230000001179 pupillary effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 208000026775 severe diarrhea Diseases 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 150000003585 thioureas Chemical class 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
- 238000010792 warming Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- G—PHYSICS
- G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
- G21C—NUCLEAR REACTORS
- G21C15/00—Cooling arrangements within the pressure vessel containing the core; Selection of specific coolants
- G21C15/02—Arrangements or disposition of passages in which heat is transferred to the coolant; Coolant flow control devices
- G21C15/04—Arrangements or disposition of passages in which heat is transferred to the coolant; Coolant flow control devices from fissile or breeder material
- G21C15/06—Arrangements or disposition of passages in which heat is transferred to the coolant; Coolant flow control devices from fissile or breeder material in fuel elements
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E30/00—Energy generation of nuclear origin
- Y02E30/30—Nuclear fission reactors
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Plasma & Fusion (AREA)
- General Engineering & Computer Science (AREA)
- High Energy & Nuclear Physics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB43702/59A GB973882A (en) | 1959-12-23 | 1959-12-23 | Benzyl-guanidines,their preparation and pharmaceutical compositions containing them |
| GB1836860 | 1960-05-24 | ||
| GB2214360 | 1960-06-24 | ||
| GB2378960 | 1960-07-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1288591B true DE1288591B (de) | 1969-02-06 |
Family
ID=27448418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEW29144A Pending DE1288591B (de) | 1959-12-23 | 1960-12-22 | Verfahren zur Herstellung von Benzylguanidinen |
Country Status (8)
| Country | Link |
|---|---|
| CH (1) | CH410905A (xx) |
| CS (1) | CS149570B2 (xx) |
| DE (1) | DE1288591B (xx) |
| DK (1) | DK106141C (xx) |
| FR (1) | FR1019M (xx) |
| LU (1) | LU39574A1 (xx) |
| MY (1) | MY6600101A (xx) |
| NL (1) | NL128795C (xx) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2030693A1 (xx) * | 1969-06-23 | 1971-01-21 |
-
1960
- 1960-12-22 DE DEW29144A patent/DE1288591B/de active Pending
- 1960-12-22 LU LU39574A patent/LU39574A1/fr unknown
- 1960-12-22 CH CH1428160A patent/CH410905A/de unknown
- 1960-12-22 DK DK507460AA patent/DK106141C/da active
- 1960-12-22 CS CS7672A patent/CS149570B2/cs unknown
- 1960-12-23 NL NL259381A patent/NL128795C/nl active
-
1961
- 1961-03-16 FR FR855866A patent/FR1019M/fr active Active
-
1966
- 1966-12-31 MY MY1966101A patent/MY6600101A/en unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2030693A1 (xx) * | 1969-06-23 | 1971-01-21 |
Also Published As
| Publication number | Publication date |
|---|---|
| CH410905A (de) | 1966-04-15 |
| NL128795C (nl) | 1969-12-15 |
| CS149570B2 (xx) | 1973-07-25 |
| DK106141C (da) | 1966-12-27 |
| FR1019M (fr) | 1961-12-26 |
| NL259381A (nl) | 1964-04-27 |
| MY6600101A (en) | 1966-12-31 |
| LU39574A1 (fr) | 1961-06-22 |
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