NO310621B1 - Fremgangsmåte ved fremstilling av tetra-azamakrosykler - Google Patents
Fremgangsmåte ved fremstilling av tetra-azamakrosykler Download PDFInfo
- Publication number
- NO310621B1 NO310621B1 NO19985992A NO985992A NO310621B1 NO 310621 B1 NO310621 B1 NO 310621B1 NO 19985992 A NO19985992 A NO 19985992A NO 985992 A NO985992 A NO 985992A NO 310621 B1 NO310621 B1 NO 310621B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- tetra
- aza
- give
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 230000003647 oxidation Effects 0.000 claims abstract description 38
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 38
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- 239000007800 oxidant agent Substances 0.000 claims abstract description 18
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical class O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002168 alkylating agent Substances 0.000 claims abstract description 10
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 10
- 238000009833 condensation Methods 0.000 claims abstract description 10
- 230000005494 condensation Effects 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 230000007062 hydrolysis Effects 0.000 claims abstract description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 9
- 229920000768 polyamine Polymers 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims description 41
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- YSPZOYMEWUTYDA-UHFFFAOYSA-N cis-glyoxal-cyclen Chemical group C1CN2CCN(CC3)C2C2N3CCN21 YSPZOYMEWUTYDA-UHFFFAOYSA-N 0.000 claims description 20
- 239000000543 intermediate Substances 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- -1 alkaline earth metal carbonates Chemical class 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000003929 acidic solution Substances 0.000 claims description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 5
- 239000000920 calcium hydroxide Substances 0.000 claims description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- NYYDZOSYLUOKEM-UHFFFAOYSA-N oxaldehyde;hydrate Chemical compound O.O=CC=O NYYDZOSYLUOKEM-UHFFFAOYSA-N 0.000 claims description 3
- 239000012286 potassium permanganate Substances 0.000 claims description 3
- 239000004289 sodium hydrogen sulphite Substances 0.000 claims description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 3
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims description 3
- 239000003021 water soluble solvent Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003957 anion exchange resin Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000010828 elution Methods 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- LADZJJOUGVGJHM-UHFFFAOYSA-N 1,4,7,10-tetrazacyclotridecane Chemical compound C1CNCCNCCNCCNC1 LADZJJOUGVGJHM-UHFFFAOYSA-N 0.000 claims 1
- MDAXKAUIABOHTD-UHFFFAOYSA-N 1,4,8,11-tetraazacyclotetradecane Chemical compound C1CNCCNCCCNCCNC1 MDAXKAUIABOHTD-UHFFFAOYSA-N 0.000 claims 1
- KUFDRRWNPNXBRF-UHFFFAOYSA-N 1,4,8,12-tetrazacyclopentadecane Chemical compound C1CNCCCNCCNCCCNC1 KUFDRRWNPNXBRF-UHFFFAOYSA-N 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000047 product Substances 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 5
- 229940015043 glyoxal Drugs 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UWMHHZFHBCYGCV-UHFFFAOYSA-N 2,3,2-tetramine Chemical compound NCCNCCCNCCN UWMHHZFHBCYGCV-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- XJFQPBHOGJVOHU-UHFFFAOYSA-N n'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine;hydrate Chemical compound O.NCCNCCNCCN XJFQPBHOGJVOHU-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ZOLACKDSSUBCNN-UHFFFAOYSA-N 5,6-dimethylcyclohexa-2,4-diene-1-carboxylic acid Chemical class CC1C(C(O)=O)C=CC=C1C ZOLACKDSSUBCNN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 150000000921 Gadolinium Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 229940039231 contrast media Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- RJOJUSXNYCILHH-UHFFFAOYSA-N gadolinium(3+) Chemical compound [Gd+3] RJOJUSXNYCILHH-UHFFFAOYSA-N 0.000 description 1
- RYHQMKVRYNEBNJ-BMWGJIJESA-K gadoterate meglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 RYHQMKVRYNEBNJ-BMWGJIJESA-K 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002595 magnetic resonance imaging Methods 0.000 description 1
- 125000005492 nosylate group Chemical group 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(I) nitrate Inorganic materials [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT96MI001257A IT1284046B1 (it) | 1996-06-21 | 1996-06-21 | Processo per la preparazione di tetraazamacrocicli |
| PCT/EP1997/002987 WO1997049691A1 (en) | 1996-06-21 | 1997-06-09 | A process for the preparation of tetraazamacrocycles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO985992D0 NO985992D0 (no) | 1998-12-18 |
| NO985992L NO985992L (no) | 1999-02-22 |
| NO310621B1 true NO310621B1 (no) | 2001-07-30 |
Family
ID=11374458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19985992A NO310621B1 (no) | 1996-06-21 | 1998-12-18 | Fremgangsmåte ved fremstilling av tetra-azamakrosykler |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US5880281A (zh) |
| EP (1) | EP0914320B1 (zh) |
| JP (1) | JP4308323B2 (zh) |
| CN (1) | CN1083442C (zh) |
| AT (1) | ATE223389T1 (zh) |
| AU (1) | AU3256497A (zh) |
| CA (1) | CA2258768C (zh) |
| CZ (1) | CZ295406B6 (zh) |
| DE (1) | DE69715211T2 (zh) |
| ES (1) | ES2183185T3 (zh) |
| HU (1) | HU223439B1 (zh) |
| IN (1) | IN183348B (zh) |
| IT (1) | IT1284046B1 (zh) |
| NO (1) | NO310621B1 (zh) |
| WO (1) | WO1997049691A1 (zh) |
| ZA (1) | ZA975425B (zh) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1284046B1 (it) * | 1996-06-21 | 1998-05-08 | Bracco Spa | Processo per la preparazione di tetraazamacrocicli |
| IT1290457B1 (it) * | 1997-04-04 | 1998-12-03 | Bracco Spa | Processo per la preparazione di tetraazamacrocicli |
| IT1291673B1 (it) * | 1997-04-28 | 1999-01-19 | Bracco Spa | Processo per la preparazione di 1,4,7,10 - tetraazaciclododecano |
| IT1293777B1 (it) * | 1997-07-25 | 1999-03-10 | Bracco Spa | Processo per la preparazione di tetraazamacrocicli |
| DE19809543A1 (de) * | 1998-03-05 | 1999-09-09 | Clariant Gmbh | Verfahren zur Herstellung von makropolycyclischen Polymaninen |
| DE19809542A1 (de) * | 1998-03-05 | 1999-09-09 | Clariant Gmbh | Quaternäre polycyclische Polyammoniumsalze und Verfahren zu deren Herstellung |
| DE19856481C1 (de) * | 1998-12-02 | 2000-07-06 | Schering Ag | Verfahren zur Herstellung von Cyclen |
| US6156890A (en) * | 1999-01-15 | 2000-12-05 | Schering Aktiengesellschaft | Process for the production of cyclene |
| IT1309601B1 (it) * | 1999-03-09 | 2002-01-24 | Bracco Spa | Processo per la preparazione di 1,4,7,10 tetraazaciclododecano. |
| US6685914B1 (en) * | 1999-09-13 | 2004-02-03 | Bristol-Myers Squibb Pharma Company | Macrocyclic chelants for metallopharmaceuticals |
| US7067111B1 (en) | 1999-10-25 | 2006-06-27 | Board Of Regents, University Of Texas System | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| DK1286704T3 (da) | 2000-06-02 | 2014-09-22 | Univ Texas | Ethylendicystein (EC)-glucose analoge konjugater |
| FR2810035B1 (fr) * | 2000-06-13 | 2004-04-16 | Air Liquide | Procede de preparation de tetraaza macrocycles et nouveaux composes |
| FR2856063B1 (fr) * | 2003-06-13 | 2005-10-07 | Air Liquide | Procede de preparation du cis-8b-methyldecahydro-2a,4a,6a, 8a-tetraazacyclopenta[fg]acenaphthylene,ou du cis-decahydro-2a,4a,6a,8a-tetraazacyclopenta[fg] acenaphthylene, du cyclene, et de cyclenes fonctionnalises |
| US7498432B2 (en) | 2003-06-25 | 2009-03-03 | Board Of Trustees Of Michigan State University | Method of synthesis of 1, 4, 7, 10, 13, 16, 21, 24-octaazabicyclo [8.8.8] hexacosane (1) and 1, 4, 7, 10, 13, 16, 21, 24-octaazabicyclo [8.8.8] hexacosa, 4, 6, 13, 15, 21, 23-hexaene (2) |
| US9050378B2 (en) * | 2003-12-10 | 2015-06-09 | Board Of Regents, The University Of Texas System | N2S2 chelate-targeting ligand conjugates |
| DE102004003710A1 (de) * | 2004-01-24 | 2005-08-11 | Clariant Gmbh | Verwendung von Übergangsmetallkomplexen als Bleichkatalysatoren in Wasch- und Reinigungsmitteln |
| US8758723B2 (en) * | 2006-04-19 | 2014-06-24 | The Board Of Regents Of The University Of Texas System | Compositions and methods for cellular imaging and therapy |
| US10925977B2 (en) * | 2006-10-05 | 2021-02-23 | Ceil>Point, LLC | Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications |
| US20100104511A1 (en) * | 2006-11-22 | 2010-04-29 | The Board Of Regents Of The University Of Texas System | Methods and compositions using chelator-antibody conjugates |
| BRPI0809442A2 (pt) | 2007-03-27 | 2014-09-09 | Radiomedix Inc | Composições para terapia e formação de imagens direcionada |
| US11473032B2 (en) | 2010-02-02 | 2022-10-18 | Fuchs Petrolub Se | Constant velocity joint having a boot |
| DK2721045T3 (en) | 2011-06-20 | 2017-07-24 | Radiomedix Inc | COMPOSITIONS, METHODS OF SYNTHESIS AND USE OF CARBOHYDRATE TARGETED AGENTS |
| CN103360333B (zh) * | 2013-07-22 | 2016-03-30 | 厦门市华兴化工有限公司 | 一种高纯度轮环藤宁的制备方法 |
| CN104387336B (zh) * | 2014-10-24 | 2016-04-27 | 上海应用技术学院 | 1,4,7,10-四氮杂环十二烷及其纳滤膜的制备方法 |
| IL271681A (en) | 2018-07-18 | 2020-01-30 | Vyripharm Entpr Llc | Systems and methods for integrated and comprehensive management of cannabis products |
| CN113801123B (zh) * | 2021-10-18 | 2022-12-09 | 苏州百灵威超精细材料有限公司 | 一种1,4,8,11-四氮杂环十四烷类化合物及其中间体的制备方法 |
| CN113956262B (zh) * | 2021-10-18 | 2023-03-07 | 苏州百灵威超精细材料有限公司 | 一种四氮杂环烷类化合物及其中间体的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3485818A (en) * | 1968-04-05 | 1969-12-23 | Jerome B Thompson | 1,4,7,10-tetraazacyclododecene and 1,4,7,10,13 - pentaazacyclopentadecene and process for their manufacture |
| US3932451A (en) * | 1973-11-27 | 1976-01-13 | E. I. Du Pont De Nemours & Company | 1,4,7,10-Tetraazatetracyclo[5.5.1.04,13.010,13 ]tridecane and its conjugate acids |
| FR2654102B1 (fr) * | 1989-11-09 | 1992-01-10 | Air Liquide | Procede de synthese de derives polyazotes cycliques. |
| US5587451A (en) * | 1993-11-26 | 1996-12-24 | The Dow Chemical Company | Process for preparing polyazamacrocycles |
| GB9504922D0 (en) * | 1995-03-10 | 1995-04-26 | Nycomed As | Process |
| IT1284046B1 (it) * | 1996-06-21 | 1998-05-08 | Bracco Spa | Processo per la preparazione di tetraazamacrocicli |
-
1996
- 1996-06-21 IT IT96MI001257A patent/IT1284046B1/it active IP Right Grant
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1997
- 1997-06-09 HU HU9903380A patent/HU223439B1/hu active IP Right Grant
- 1997-06-09 DE DE69715211T patent/DE69715211T2/de not_active Expired - Lifetime
- 1997-06-09 EP EP97928162A patent/EP0914320B1/en not_active Expired - Lifetime
- 1997-06-09 ES ES97928162T patent/ES2183185T3/es not_active Expired - Lifetime
- 1997-06-09 WO PCT/EP1997/002987 patent/WO1997049691A1/en active IP Right Grant
- 1997-06-09 CA CA002258768A patent/CA2258768C/en not_active Expired - Lifetime
- 1997-06-09 CZ CZ19984210A patent/CZ295406B6/cs not_active IP Right Cessation
- 1997-06-09 JP JP50219498A patent/JP4308323B2/ja not_active Expired - Lifetime
- 1997-06-09 AT AT97928162T patent/ATE223389T1/de not_active IP Right Cessation
- 1997-06-09 AU AU32564/97A patent/AU3256497A/en not_active Abandoned
- 1997-06-09 CN CN97195647A patent/CN1083442C/zh not_active Expired - Lifetime
- 1997-06-19 ZA ZA9705425A patent/ZA975425B/xx unknown
- 1997-06-19 US US08/878,508 patent/US5880281A/en not_active Expired - Lifetime
- 1997-06-19 IN IN1333MA1997 patent/IN183348B/en unknown
-
1998
- 1998-12-02 US US09/203,595 patent/US6114521A/en not_active Expired - Lifetime
- 1998-12-02 US US09/203,604 patent/US6013793A/en not_active Expired - Lifetime
- 1998-12-18 NO NO19985992A patent/NO310621B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO985992L (no) | 1999-02-22 |
| EP0914320B1 (en) | 2002-09-04 |
| EP0914320A1 (en) | 1999-05-12 |
| ATE223389T1 (de) | 2002-09-15 |
| JP4308323B2 (ja) | 2009-08-05 |
| CN1083442C (zh) | 2002-04-24 |
| HUP9903380A3 (en) | 2001-07-30 |
| CN1222147A (zh) | 1999-07-07 |
| ITMI961257A1 (it) | 1997-12-21 |
| NO985992D0 (no) | 1998-12-18 |
| US6013793A (en) | 2000-01-11 |
| CA2258768A1 (en) | 1997-12-31 |
| WO1997049691A1 (en) | 1997-12-31 |
| CZ421098A3 (cs) | 1999-06-16 |
| ES2183185T3 (es) | 2003-03-16 |
| DE69715211T2 (de) | 2003-08-07 |
| ITMI961257A0 (zh) | 1996-06-21 |
| CZ295406B6 (cs) | 2005-08-17 |
| IT1284046B1 (it) | 1998-05-08 |
| ZA975425B (en) | 1998-01-26 |
| JP2000512642A (ja) | 2000-09-26 |
| IN183348B (zh) | 1999-11-27 |
| HU223439B1 (hu) | 2004-07-28 |
| US6114521A (en) | 2000-09-05 |
| US5880281A (en) | 1999-03-09 |
| DE69715211D1 (de) | 2002-10-10 |
| AU3256497A (en) | 1998-01-14 |
| CA2258768C (en) | 2009-03-10 |
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