CA1055022A - Macrocyclic polyamines - Google Patents
Macrocyclic polyaminesInfo
- Publication number
- CA1055022A CA1055022A CA210,452A CA210452A CA1055022A CA 1055022 A CA1055022 A CA 1055022A CA 210452 A CA210452 A CA 210452A CA 1055022 A CA1055022 A CA 1055022A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- solution
- salt
- complex
- product
- 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.)
- Expired
Links
- 229920000768 polyamine Polymers 0.000 title abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims abstract description 17
- 239000002184 metal Substances 0.000 claims abstract description 17
- -1 p-toluenesulfonyl Chemical group 0.000 claims description 9
- KDCBVVQAMMXRFB-UHFFFAOYSA-N 1,4,7,10,13-pentazacyclopentadecane Chemical compound C1CNCCNCCNCCNCCN1 KDCBVVQAMMXRFB-UHFFFAOYSA-N 0.000 claims description 7
- YGDOUVAXGKNMEN-UHFFFAOYSA-N 1,4,7-triazacyclododecane Chemical compound C1CCNCCNCCNCC1 YGDOUVAXGKNMEN-UHFFFAOYSA-N 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- RVJABZUDCPZPPM-UHFFFAOYSA-N 1,4,7,10,13,16-hexazacyclooctadecane Chemical compound C1CNCCNCCNCCNCCNCCN1 RVJABZUDCPZPPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- NYYYCSIMGPEGOA-UHFFFAOYSA-N 1,4,7,13,16,19-hexazacyclotetracosane Chemical compound C1CCNCCNCCNCCCCCNCCNCCNCC1 NYYYCSIMGPEGOA-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- KZDVXQXPGPRERX-UHFFFAOYSA-N 1,4,7,10,13,16,19-heptazacyclohenicosane Chemical compound C1CNCCNCCNCCNCCNCCNCCN1 KZDVXQXPGPRERX-UHFFFAOYSA-N 0.000 claims description 3
- YXPRJLINFVQPDT-UHFFFAOYSA-N 1,5,9,13-tetrazacyclohexadecane Chemical compound C1CNCCCNCCCNCCCNC1 YXPRJLINFVQPDT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 abstract description 7
- 229920000647 polyepoxide Polymers 0.000 abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 230000009918 complex formation Effects 0.000 abstract description 3
- 229910021645 metal ion Inorganic materials 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 150000003839 salts Chemical class 0.000 description 24
- 239000000047 product Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000523 sample Substances 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000004699 copper complex Chemical class 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002678 macrocyclic compounds Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 229940116269 uric acid Drugs 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- APCWGAGIRFNQOI-UHFFFAOYSA-N 1,2,3,4,5,6-hexazacyclooctadecane Chemical compound C1CCCCCCNNNNNNCCCCC1 APCWGAGIRFNQOI-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- 241001598984 Bromius obscurus Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000009850 completed effect Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- JNFIMRWCDIOUMT-UHFFFAOYSA-N cyclooctadecane Chemical compound C1CCCCCCCCCCCCCCCCC1 JNFIMRWCDIOUMT-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 101150018104 tlcC gene Proteins 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D255/00—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00
- C07D255/02—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D259/00—Heterocyclic compounds containing rings having more than four nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5093—Complexes of amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/403,326 US4001212A (en) | 1973-10-03 | 1973-10-03 | Macrocyclic polyamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055022A true CA1055022A (en) | 1979-05-22 |
Family
ID=23595377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA210,452A Expired CA1055022A (en) | 1973-10-03 | 1974-10-01 | Macrocyclic polyamines |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4001212A (enExample) |
| JP (1) | JPS5059385A (enExample) |
| CA (1) | CA1055022A (enExample) |
| DE (1) | DE2447279A1 (enExample) |
| FR (1) | FR2246555B1 (enExample) |
| GB (1) | GB1483821A (enExample) |
| IT (1) | IT1022572B (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2803528C2 (de) | 1977-03-09 | 1984-10-18 | Tabushi, Iwao, Kyoto | Schwermetallionen-Adsorbens und dessen Verwendung zum Adsorbieren von Schwermetallionen |
| JPS53144592A (en) | 1977-05-19 | 1978-12-15 | Tabuse Iwao | 122alkyll1*4*7*100tetrazacyclotridecane |
| JPS53144593A (en) | 1977-05-19 | 1978-12-15 | Iwao Tabuse | Alklycyclum |
| US4190462A (en) * | 1978-07-04 | 1980-02-26 | Shell Oil Company | Dissolving barium sulfate scale with aqueous solutions of salts of carboxymethyl monocyclic macrocyclic polyamines |
| US4309305A (en) * | 1978-07-24 | 1982-01-05 | The United States As Represented By The United States Department Of Energy | In vitro removal of actinide (IV) ions |
| US4181654A (en) | 1978-07-24 | 1980-01-01 | The United States Of America As Represented By The United States Department Of Energy | 2,3-Dihydroxybenzoic acid amides of tetraazaalkanes and tetaaza cycloalkanes |
| NO149961C (no) * | 1981-06-01 | 1984-07-25 | Borregaard Ind | Fremgangsmaate for fremstilling av n-(2-hydroksyetyl)-derivater av makrocykliske polyaminer, inneholdende flere nitrogenatomer i 1,4-forhold i ringen |
| US4569750A (en) * | 1984-11-27 | 1986-02-11 | Exxon Research & Engineering Co. | Method for inhibiting deposit formation in structures confining hydrocarbon fluids |
| JPS61226751A (ja) * | 1985-03-30 | 1986-10-08 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料用処理液及びその処理方法 |
| US4750373A (en) * | 1987-01-22 | 1988-06-14 | Shapiro Justin J | Adjustable volume, pressure-generating pipette sampler |
| WO1990009379A1 (en) * | 1989-02-10 | 1990-08-23 | Celltech Limited | Aza-macrocycles and processes for their preparation |
| US5011925A (en) * | 1989-03-09 | 1991-04-30 | Mallinckrodt, Inc. | Morpholinoamido EDTA derivatives |
| US5384108A (en) * | 1989-04-24 | 1995-01-24 | Mallinckrodt Medical, Inc. | Magnetic resonance imaging agents |
| FR2654102B1 (fr) * | 1989-11-09 | 1992-01-10 | Air Liquide | Procede de synthese de derives polyazotes cycliques. |
| CA2072934C (en) * | 1991-07-19 | 2007-08-28 | Karl William Aston | Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| TW226994B (enExample) * | 1991-08-21 | 1994-07-21 | Hoechst Ag | |
| US5318772A (en) * | 1991-12-10 | 1994-06-07 | The Dow Chemical Company | Oral compositions for inhibiting calculus formation |
| US5320829A (en) * | 1991-12-10 | 1994-06-14 | The Dow Chemical Company | Oral compositions for inhibiting plaque formation |
| US5284944A (en) * | 1992-06-30 | 1994-02-08 | Lever Brothers Company, Division Of Conopco, Inc. | Improved synthesis of 1,4,7-triazacyclononane |
| US5326861A (en) * | 1992-10-21 | 1994-07-05 | Lever Brothers Company, Division Of Conopco, Inc. | Preparation of organic macrocyclic compounds |
| US6204259B1 (en) | 1993-01-14 | 2001-03-20 | Monsanto Company | Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| CZ307096A3 (en) * | 1994-04-22 | 1997-09-17 | Monsanto Co | Methods of video analysis by making use of metal complexes of nitrogen-containing macrocyclic ligands |
| US5663161A (en) | 1995-02-17 | 1997-09-02 | The Research Foundation Of State University Of New York | Anti-viral triaza compounds |
| US6525041B1 (en) | 1995-06-06 | 2003-02-25 | Pharmacia Corporation | Manganese or iron complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide |
| WO1997006830A1 (en) * | 1995-08-17 | 1997-02-27 | Monsanto Company | Methods of diagnostic image analysis using bioconjugates of metal complexes of nitrogen-containing macrocyclic ligands |
| EP0844889A1 (en) * | 1995-08-17 | 1998-06-03 | Monsanto Company | Methods of diagnostic image analysis using metal complexes of nitrogen-containing macrocyclic ligands |
| US6214817B1 (en) | 1997-06-20 | 2001-04-10 | Monsanto Company | Substituted pyridino pentaazamacrocyle complexes having superoxide dismutase activity |
| KR100510153B1 (ko) * | 2002-09-10 | 2005-08-24 | 경북대학교 산학협력단 | 1,5,9-트리아자시클로도데칸 유도체, 이를 이용한 금의용매 추출 방법 |
| US7319038B2 (en) * | 2002-09-19 | 2008-01-15 | The Johns Hopkins University | Sensor for monitoring an analyte |
| LT2056675T (lt) | 2006-10-12 | 2019-05-27 | Galera Labs, Llc | Burnos gleivinės mukozito gydymo būdai |
| CA3120505C (en) | 2011-09-26 | 2024-11-12 | Galera Labs, Llc | METHODS OF TREATING DISEASES |
| US9269998B2 (en) | 2013-03-13 | 2016-02-23 | Fluidic, Inc. | Concave gas vent for electrochemical cell |
| UA126788C2 (uk) | 2015-08-11 | 2023-02-08 | Ґалера Лебз, Елелсі | Комплексні сполуки, що містять макроциклічне кільце пентаази, які мають пероральну біодоступність |
| MX393974B (es) | 2016-05-03 | 2025-03-24 | Galera Labs Llc | Terapia de combinacion para tratamiento de cancer. |
| CN109565097A (zh) | 2016-07-22 | 2019-04-02 | 南特能源公司 | 电化学电池的除雾系统 |
| BR112019000713B1 (pt) | 2016-07-22 | 2023-04-25 | Nantenergy, Inc | Célula eletroquímica e método de conservar umidade dentro de uma célula eletroquímica |
| JP7166634B2 (ja) | 2016-09-01 | 2022-11-08 | ガレラ・ラブス・リミテッド・ライアビリティ・カンパニー | ペンタアザ大環状環複合体およびアスコルビン酸化合物による組み合わせ癌療法 |
| EA201992431A1 (ru) | 2017-10-13 | 2020-03-13 | ГАЛЕРА ЛЭБЗ, ЭлЭлСи | Комбинированная иммунотерапия рака с использованием пента-аза-макроциклического кольцевого комплекса |
| EP3815172A4 (en) | 2018-06-29 | 2022-03-09 | Form Energy, Inc. | ROLLER DIAPHRAGM SEAL |
| WO2020006419A1 (en) | 2018-06-29 | 2020-01-02 | Form Energy Inc. | Metal air electrochemical cell architecture |
| WO2020264344A1 (en) | 2019-06-28 | 2020-12-30 | Form Energy Inc. | Device architectures for metal-air batteries |
| WO2021226399A1 (en) | 2020-05-06 | 2021-11-11 | Form Energy, Inc. | Decoupled electrode electrochemical energy storage system |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1951992A (en) * | 1931-07-15 | 1934-03-20 | Carbide & Carbon Chem Corp | Separation of acid gases |
-
1973
- 1973-10-03 US US05/403,326 patent/US4001212A/en not_active Expired - Lifetime
-
1974
- 1974-10-01 CA CA210,452A patent/CA1055022A/en not_active Expired
- 1974-10-02 JP JP49112864A patent/JPS5059385A/ja active Pending
- 1974-10-02 IT IT28020/74A patent/IT1022572B/it active
- 1974-10-02 FR FR7433171A patent/FR2246555B1/fr not_active Expired
- 1974-10-02 GB GB42772/74A patent/GB1483821A/en not_active Expired
- 1974-10-03 DE DE19742447279 patent/DE2447279A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE2447279A1 (de) | 1975-04-10 |
| FR2246555A1 (enExample) | 1975-05-02 |
| GB1483821A (en) | 1977-08-24 |
| US4001212A (en) | 1977-01-04 |
| JPS5059385A (enExample) | 1975-05-22 |
| USB403326I5 (enExample) | 1976-03-23 |
| IT1022572B (it) | 1978-04-20 |
| FR2246555B1 (enExample) | 1979-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4001212A (en) | Macrocyclic polyamines | |
| Suh et al. | Synthesis and properties of nickel (II) and copper (II) complexes of 14-membered hexaaza macrocycles, 1, 8-dimethyl-and 1, 8-diethyl-1, 3, 6, 8, 10, 13-hexaazacyclotetradecane | |
| US4174428A (en) | Heavy metal ion adsorbents | |
| Abla et al. | Oxidative addition of C CN bond to nickel (0) complex: Synthesis and crystal structures of Ni (CN)(o-C6H4CN)(bpy) and Ni (CN)(p-C6H4CN)(bpy) | |
| CN114014800B (zh) | 一种2-偕二硝甲基吡啶胺盐化合物、制备方法及其应用 | |
| Brianese et al. | Asymmetric compartmental macrocyclic ligands and related mononuclear and hetero-dinuclear complexes with d-and/or f-metal ions | |
| JPH0733766A (ja) | イミダゾール環を有するジアミノ−ｓ−トリアジン化合物及び該化合物を用いる銅の防錆方法 | |
| US5434262A (en) | Process for the synthesis of cyclic polynitrogenated compounds | |
| EP0080478B1 (en) | N-hydroxyethylated macrocyclic polyamines, the preparation of such amines and their use | |
| Ertas et al. | Synthesis of a novel [10] ferrocenophanedioxime with bridge heteroatoms and of its nickel (II) complex | |
| Sclafani et al. | Terminal alkylation of linear polyamines | |
| Oliveira et al. | Preparation of novel cobalt (III) complexes with dithiocarbimates derived from sulfonamides | |
| Wang et al. | Unusual stabilities of 6, 6′-bis (aminomethyl)-2, 2′-bipyridyl chelates of transition-metal ions and crystal structures of the ligand and its copper (II) and nickel (II) complexes | |
| DE69432105T2 (de) | Verfahren zur herstellung von polyazamacrocylen | |
| CA1062255A (en) | Macrocyclic compounds and complexes thereof | |
| Akabori et al. | Synthesis and physicochemical properties of dioxathia (n) ferrocenophanes. | |
| US4076724A (en) | Polycyclic macrocyclic compounds | |
| US2953600A (en) | Phenol-hydrazinium inner salts | |
| US4115397A (en) | Metal chelating ligands | |
| Kinoshita et al. | Synthesis of 3, 3′‐(1, 6‐hexanediyl) bis‐pyrimidine derivatives and 3, 4‐dithia [6.6](1.3) pyrimidinophane | |
| Park et al. | New Macrocyclic Ligands. XV. Isomeric, Benzylated and Xylyl-Linked Macrocyclic Ligands Derived from Selectively Protected N 3 O 2-Donor Rings | |
| US3928328A (en) | Schiff base and metal bisazomethine metal chelate | |
| Weis et al. | Dihydropyrimidines. 7. Synthesis and crystal structure of 2, 4-diaza-6, 7-benzo-8-oxabicyclo-[3.3. 1]-nonenes | |
| Fujihara et al. | Preparation and structure of new diazaselenuranes. Transannular hypervalent bond between seleno and diamino groups | |
| Gahan et al. | Synthesis, resolution and spectral properties of the cobalt (III) complex of the hexadentate ligand 2, 2', 2'-[(cyclohexane-1, 3, 5-triyl) trithio] tris (ethanamine) |