DK175509B1 - Fremgangsmåde til fremstilling af mono-N-alkylerede polyazamakrocykliske forbindelser - Google Patents

Fremgangsmåde til fremstilling af mono-N-alkylerede polyazamakrocykliske forbindelser Download PDF

Info

Publication number: DK175509B1
Authority: DK; Denmark
Prior art keywords: process according; solvent; compound; polyazamacrocyclic; mono
Prior art date: 1988-12-22

Application number

DK198906654A

Other languages

Danish (da)

English (en)

Other versions

DK665489D0 (da

DK665489A (da

Inventor

J Kruper William Jr

Original Assignee

Dow Global Technologies Inc

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.)

1988-12-22

Filing date

1989-12-22

Publication date

2004-11-15

1989-12-22 Application filed by Dow Global Technologies Inc filed Critical Dow Global Technologies Inc

1989-12-22 Publication of DK665489D0 publication Critical patent/DK665489D0/da

1990-06-23 Publication of DK665489A publication Critical patent/DK665489A/da

2004-11-15 Application granted granted Critical

2004-11-15 Publication of DK175509B1 publication Critical patent/DK175509B1/da

Links

150000001875 compounds Chemical class 0.000 title claims description 58
238000000034 method Methods 0.000 title claims description 50
238000002360 preparation method Methods 0.000 title description 13
239000002904 solvent Substances 0.000 claims description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
-1 cyano, pyridinyl Chemical group 0.000 claims description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
150000003335 secondary amines Chemical class 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
238000012546 transfer Methods 0.000 claims description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
150000007543 12-membered macrocycles Chemical class 0.000 claims description 2
PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical group 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
SPSGYTWOIGAABK-DQEYMECFSA-N [4-[(2s)-2-acetamido-3-[[(5s)-3-carbamoyl-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-yl]amino]-3-oxopropyl]-2-phosphonophenyl]phosphonic acid Chemical compound C([C@H](NC(=O)C)C(=O)N[C@@H]1C2=CC(=C(OCC3CCCCC3)C=C2CCCC1)C(N)=O)C1=CC=C(P(O)(O)=O)C(P(O)(O)=O)=C1 SPSGYTWOIGAABK-DQEYMECFSA-N 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
239000003880 polar aprotic solvent Substances 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 16
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
239000002585 base Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000002678 macrocyclic compounds Chemical class 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000004433 nitrogen atom Chemical group N* 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
238000007126 N-alkylation reaction Methods 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 description 3
VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 3
239000012039 electrophile Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
238000010828 elution Methods 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
230000037361 pathway Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
LKEAXACDEKSPTH-UHFFFAOYSA-N (2-bromo-1-nitroethyl)benzene Chemical compound [O-][N+](=O)C(CBr)C1=CC=CC=C1 LKEAXACDEKSPTH-UHFFFAOYSA-N 0.000 description 1
YBNZVBUWVIIJND-UHFFFAOYSA-N (2z)-1-cyclononyl-2-diazocyclononane Chemical compound [N-]=[N+]=C1CCCCCCCC1C1CCCCCCCC1 YBNZVBUWVIIJND-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
KDCBVVQAMMXRFB-UHFFFAOYSA-N 1,4,7,10,13-pentazacyclopentadecane Chemical compound C1CNCCNCCNCCNCCN1 KDCBVVQAMMXRFB-UHFFFAOYSA-N 0.000 description 1
MDAXKAUIABOHTD-UHFFFAOYSA-N 1,4,8,11-tetraazacyclotetradecane Chemical compound C1CNCCNCCCNCCNC1 MDAXKAUIABOHTD-UHFFFAOYSA-N 0.000 description 1
KZGWLAIHOOETTE-UHFFFAOYSA-N 1,6-dithia-3,9-diazacyclododecane Chemical compound C1CNCCSCCNCSC1 KZGWLAIHOOETTE-UHFFFAOYSA-N 0.000 description 1
IENMSXPRVAEDIW-OWOJBTEDSA-N 1-[(e)-3-bromoprop-1-enyl]-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(\C=C\CBr)C=C1 IENMSXPRVAEDIW-OWOJBTEDSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
WQMLUHZFRFCQDB-UHFFFAOYSA-N 4-(4-nitrophenyl)butyric acid Chemical compound OC(=O)CCCC1=CC=C([N+]([O-])=O)C=C1 WQMLUHZFRFCQDB-UHFFFAOYSA-N 0.000 description 1
YSDBVGOELWOMIR-UHFFFAOYSA-N 4-(diazo-lambda3-bromanyl)benzenesulfonic acid Chemical compound C1=CC(=CC=C1S(=O)(=O)O)Br=[N+]=[N-] YSDBVGOELWOMIR-UHFFFAOYSA-N 0.000 description 1
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
101100453572 Arabidopsis thaliana KCO3 gene Proteins 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
239000001970 CHU 13 medium Substances 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
101100453573 Oryza sativa subsp. japonica TPKC gene Proteins 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000000470 constituent Substances 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
230000005595 deprotonation Effects 0.000 description 1
238000010537 deprotonation reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000006345 epimerization reaction Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000007306 functionalization reaction Methods 0.000 description 1
229960003692 gamma aminobutyric acid Drugs 0.000 description 1
239000000499 gel Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000006263 metalation reaction Methods 0.000 description 1
DZYUUIAQLLHFQZ-UHFFFAOYSA-N n,n-diethyl-2h-pyridin-1-amine Chemical compound CCN(CC)N1CC=CC=C1 DZYUUIAQLLHFQZ-UHFFFAOYSA-N 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03K—PULSE TECHNIQUE
- H03K19/00—Logic circuits, i.e. having at least two inputs acting on one output; Inverting circuits
- H03K19/02—Logic circuits, i.e. having at least two inputs acting on one output; Inverting circuits using specified components
- H03K19/08—Logic circuits, i.e. having at least two inputs acting on one output; Inverting circuits using specified components using semiconductor devices
- H03K19/094—Logic circuits, i.e. having at least two inputs acting on one output; Inverting circuits using specified components using semiconductor devices using field-effect transistors
- H03K19/09432—Logic circuits, i.e. having at least two inputs acting on one output; Inverting circuits using specified components using semiconductor devices using field-effect transistors with coupled sources or source coupled logic
- H03K19/09436—Source coupled field-effect logic [SCFL]
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03K—PULSE TECHNIQUE
- H03K3/00—Circuits for generating electric pulses; Monostable, bistable or multistable circuits
- H03K3/02—Generators characterised by the type of circuit or by the means used for producing pulses
- H03K3/353—Generators characterised by the type of circuit or by the means used for producing pulses by the use, as active elements, of field-effect transistors with internal or external positive feedback
- H03K3/356—Bistable circuits
- H03K3/3565—Bistables with hysteresis, e.g. Schmitt trigger

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Mathematical Physics (AREA)
Physics & Mathematics (AREA)
Computer Hardware Design (AREA)
Computing Systems (AREA)
General Engineering & Computer Science (AREA)
Power Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DK198906654A 1988-12-22 1989-12-22 Fremgangsmåde til fremstilling af mono-N-alkylerede polyazamakrocykliske forbindelser DK175509B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US28916388A	1988-12-22	1988-12-22
US28916388		1988-12-22

Publications (3)

Publication Number	Publication Date
DK665489D0 DK665489D0 (da)	1989-12-22
DK665489A DK665489A (da)	1990-06-23
DK175509B1 true DK175509B1 (da)	2004-11-15

Family

ID=23110317

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198906654A DK175509B1 (da)	1988-12-22	1989-12-22	Fremgangsmåde til fremstilling af mono-N-alkylerede polyazamakrocykliske forbindelser

Country Status (18)

Country	Link
EP (1)	EP0374929B1 (zh)
JP (1)	JP2930709B2 (zh)
KR (1)	KR0160113B1 (zh)
CN (1)	CN1028172C (zh)
BR (1)	BR8907277A (zh)
CA (1)	CA2006358C (zh)
DE (1)	DE68928619T2 (zh)
DK (1)	DK175509B1 (zh)
ES (1)	ES2113846T3 (zh)
FI (1)	FI104171B1 (zh)
GR (1)	GR3026745T3 (zh)
HU (1)	HU208317B (zh)
IL (1)	IL92844A (zh)
NO (1)	NO177496C (zh)
PH (1)	PH30234A (zh)
PT (1)	PT92638B (zh)
SG (1)	SG47867A1 (zh)
WO (1)	WO1990007261A2 (zh)

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* Cited by examiner, † Cited by third party
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US5362476A (en) *	1984-10-18	1994-11-08	Board Of Regents, The University Of Texas System	Alkyl phosphonate polyazamacrocyclic cheates for MRI
US5316757A (en) *	1984-10-18	1994-05-31	Board Of Regents, The University Of Texas System	Synthesis of polyazamacrocycles with more than one type of side-chain chelating groups
FR2654102B1 (fr) *	1989-11-09	1992-01-10	Air Liquide	Procede de synthese de derives polyazotes cycliques.
FR2672051B1 (fr) *	1991-01-24	1993-05-21	Guerbet Sa	Nouveaux ligands macrocycliques azotes, procede de preparation, complexes polymetalliques, composition de diagnostic et therapeutique.
CA2072934C (en) *	1991-07-19	2007-08-28	Karl William Aston	Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide
US5410043A (en) *	1991-12-06	1995-04-25	Schering Aktiengesellschaft	Process for the production of mono-N-substituted tetraaza macrocycles
DE4218744C2 (de) *	1992-06-04	1997-11-06	Schering Ag	Verfahren zur Herstellung von N-ß-Hxdroxyalkyl-tri-N-carboxylalkyl-1,4,7,10-tetraazacyclododecan- und N-ß-Hydroxyalkyl-tri-N-carboxyalkyl-1,4,8,11-tetraazacyclotetradecan-Derivaten und deren Metallkomplexe
EP0588229A3 (en) *	1992-09-12	1994-06-15	Hoechst Ag	Macrocyclic chelating agents for the preparation of technetium or rhenium complexes
US6204259B1 (en)	1993-01-14	2001-03-20	Monsanto Company	Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide
GB9504910D0 (en) *	1995-03-10	1995-04-26	Nycomed Imaging As	Compounds
US5612478A (en) *	1995-03-30	1997-03-18	Johnson Matthey Plc	Process for preparing 1,1'-[1,4-phenylenebis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane
US5606053A (en) *	1995-05-02	1997-02-25	Johnson Matthey Plc	Process for preparing 1,1'-[1,4-phenylenebis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane
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
US5608061A (en) *	1995-08-02	1997-03-04	Johnson Matthey Plc	Process for preparing 1,4,8,11-tetraazacyclotetradecane
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
BR112013000236B1 (pt) *	2010-07-06	2018-11-13	Catexel Limited	método de produzir um composto, e, sal protonado
CN114560829B (zh) *	2022-03-17	2023-08-04	中山大学	一种大环单体的制备方法及其开环聚合反应

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Publication number	Priority date	Publication date	Assignee	Title
FI60559C (fi) *	1975-07-17	1982-02-10	Sumitomo Chemical Co	Foerfarande foer framstaellning av ny-(tertiaer amino)-orto-aminobutyrofenonfoereningar
EP0232751B1 (en) *	1986-01-23	1991-09-11	E.R. Squibb & Sons, Inc.	1-substituted-4,7,10-triscarboxymethyl-1,4,7,10-tetraazacyclododecane and analogs
JPS6314780A (ja) *	1986-07-08	1988-01-21	Tosoh Corp	クラウンエ−テル連結大環状ポリアミン類およびその製造法
FR2613718B1 (fr) *	1987-04-10	1990-12-14	Centre Nat Rech Scient	Tetramines cycliques monofonctionnalisees, leur procede de preparation, leurs polymeres et utilisation de ces polymeres
US4994560A (en) *	1987-06-24	1991-02-19	The Dow Chemical Company	Functionalized polyamine chelants and radioactive rhodium complexes thereof for conjugation to antibodies

1989
- 1989-12-15 JP JP2502255A patent/JP2930709B2/ja not_active Expired - Lifetime
- 1989-12-15 WO PCT/US1989/005784 patent/WO1990007261A2/en not_active Ceased
- 1989-12-15 BR BR898907277A patent/BR8907277A/pt not_active IP Right Cessation
- 1989-12-20 PT PT92638A patent/PT92638B/pt active IP Right Grant
- 1989-12-21 FI FI896171A patent/FI104171B1/fi not_active IP Right Cessation
- 1989-12-21 IL IL9284489A patent/IL92844A/en not_active IP Right Cessation
- 1989-12-21 NO NO895176A patent/NO177496C/no unknown
- 1989-12-21 CN CN89109817A patent/CN1028172C/zh not_active Expired - Lifetime
- 1989-12-21 DE DE68928619T patent/DE68928619T2/de not_active Expired - Lifetime
- 1989-12-21 HU HU896728A patent/HU208317B/hu not_active IP Right Cessation
- 1989-12-21 EP EP89123685A patent/EP0374929B1/en not_active Expired - Lifetime
- 1989-12-21 SG SG1996004825A patent/SG47867A1/en unknown
- 1989-12-21 ES ES89123685T patent/ES2113846T3/es not_active Expired - Lifetime
- 1989-12-21 CA CA002006358A patent/CA2006358C/en not_active Expired - Fee Related
- 1989-12-21 KR KR1019890019142A patent/KR0160113B1/ko not_active Expired - Fee Related
- 1989-12-22 DK DK198906654A patent/DK175509B1/da not_active IP Right Cessation
1990
- 1990-02-28 PH PH40028A patent/PH30234A/en unknown
1998
- 1998-04-28 GR GR980400938T patent/GR3026745T3/el unknown

Also Published As

Publication number	Publication date
PH30234A (en)	1997-02-05
NO895176L (no)	1990-06-25
PT92638B (pt)	1995-09-12
CA2006358A1 (en)	1990-06-22
PT92638A (pt)	1990-06-29
FI896171A0 (fi)	1989-12-21
CA2006358C (en)	1998-07-07
ES2113846T3 (es)	1998-05-16
NO177496B (no)	1995-06-19
WO1990007261A2 (en)	1990-07-12
DE68928619T2 (de)	1998-07-16
SG47867A1 (en)	1998-04-17
WO1990007261A3 (en)	1990-11-29
HUT52487A (en)	1990-07-28
NO177496C (no)	1995-09-27
NO895176D0 (no)	1989-12-21
JP2930709B2 (ja)	1999-08-03
DK665489D0 (da)	1989-12-22
GR3026745T3 (en)	1998-07-31
IL92844A0 (en)	1990-09-17
HK1008425A1 (zh)	1999-05-07
CN1044096A (zh)	1990-07-25
FI104171B (fi)	1999-11-30
BR8907277A (pt)	1991-03-26
EP0374929A1 (en)	1990-06-27
FI104171B1 (fi)	1999-11-30
HU208317B (en)	1993-09-28
KR900009790A (ko)	1990-07-05
DK665489A (da)	1990-06-23
JPH02503141A (ja)	1990-09-27
HU896728D0 (en)	1990-03-28
DE68928619D1 (de)	1998-04-30
IL92844A (en)	1994-11-28
CN1028172C (zh)	1995-04-12
EP0374929B1 (en)	1998-03-25
KR0160113B1 (ko)	1998-12-01

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