CN101035755B - 脱保护的方法 - Google Patents
脱保护的方法 Download PDFInfo
- Publication number
- CN101035755B CN101035755B CN2005800338074A CN200580033807A CN101035755B CN 101035755 B CN101035755 B CN 101035755B CN 2005800338074 A CN2005800338074 A CN 2005800338074A CN 200580033807 A CN200580033807 A CN 200580033807A CN 101035755 B CN101035755 B CN 101035755B
- Authority
- CN
- China
- Prior art keywords
- protected
- acid
- deprotection
- method described
- agent
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 61
- 238000010511 deprotection reaction Methods 0.000 title claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 52
- 239000002253 acid Substances 0.000 claims abstract description 42
- 230000003139 buffering effect Effects 0.000 claims abstract description 9
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 57
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 54
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 24
- 239000000700 radioactive tracer Substances 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 230000003472 neutralizing effect Effects 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000000872 buffer Substances 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- -1 alkane carboxylicesters Chemical class 0.000 claims description 9
- 230000001954 sterilising effect Effects 0.000 claims description 7
- 238000004659 sterilization and disinfection Methods 0.000 claims description 7
- 239000012071 phase Substances 0.000 claims description 6
- 238000010189 synthetic method Methods 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 150000002703 mannose derivatives Chemical class 0.000 claims description 4
- ZCXUVYAZINUVJD-AHXZWLDOSA-N 2-deoxy-2-((18)F)fluoro-alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H]([18F])[C@@H](O)[C@@H]1O ZCXUVYAZINUVJD-AHXZWLDOSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-PQMKYFCFSA-N alpha-D-mannose Chemical compound OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-PQMKYFCFSA-N 0.000 claims description 2
- 238000003746 solid phase reaction Methods 0.000 claims description 2
- 238000010671 solid-state reaction Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000000159 acid neutralizing agent Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 239000012217 radiopharmaceutical Substances 0.000 abstract 1
- 229940121896 radiopharmaceutical Drugs 0.000 abstract 1
- 230000002799 radiopharmaceutical effect Effects 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000004448 titration Methods 0.000 description 8
- 239000002243 precursor Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000008363 phosphate buffer Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000000835 electrochemical detection Methods 0.000 description 3
- 229910021397 glassy carbon Inorganic materials 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000003016 phosphoric acids Chemical class 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- 229910000162 sodium phosphate Inorganic materials 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 150000007516 brønsted-lowry acids Chemical class 0.000 description 2
- 150000007528 brønsted-lowry bases Chemical class 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910001853 inorganic hydroxide Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000035479 physiological effects, processes and functions Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010532 solid phase synthesis reaction Methods 0.000 description 2
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 1
- JMDCRDOIPYCSCH-RPDRGXCHSA-N (2S)-3-(3,4-dihydroxyphenyl)-2-(fluoranylamino)propanoic acid Chemical compound [18F]N[C@H](C(=O)O)CC1=CC=C(O)C(O)=C1 JMDCRDOIPYCSCH-RPDRGXCHSA-N 0.000 description 1
- UXCAQJAQSWSNPQ-ZIVQXEJRSA-N 1-[(2r,4s,5r)-4-fluoranyl-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H]([18F])C1 UXCAQJAQSWSNPQ-ZIVQXEJRSA-N 0.000 description 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- QVWCHVAUHZEAAT-UHFFFAOYSA-N 2-fluoro-1,3-benzothiazole Chemical compound C1=CC=C2SC(F)=NC2=C1 QVWCHVAUHZEAAT-UHFFFAOYSA-N 0.000 description 1
- PAXWQORCRCBOCU-LURJTMIESA-N 6-fluoro-L-dopa Chemical compound OC(=O)[C@@H](N)CC1=CC(O)=C(O)C=C1F PAXWQORCRCBOCU-LURJTMIESA-N 0.000 description 1
- SMYALUSCZJXWHG-UHFFFAOYSA-N Altanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=S)=O)CC1 SMYALUSCZJXWHG-UHFFFAOYSA-N 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical class CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102100024304 Protachykinin-1 Human genes 0.000 description 1
- 101800003906 Substance P Proteins 0.000 description 1
- OIBDVHSTOUGZTJ-PEBLQZBPSA-N [(2r,3r,4s,5s,6s)-3,4,6-triacetyloxy-5-(trifluoromethylsulfonyloxy)oxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@@H](OS(=O)(=O)C(F)(F)F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O OIBDVHSTOUGZTJ-PEBLQZBPSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000012382 advanced drug delivery Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940027541 fluciclovine f-18 Drugs 0.000 description 1
- 125000005519 fluorenylmethyloxycarbonyl group Chemical group 0.000 description 1
- KRHYYFGTRYWZRS-BJUDXGSMSA-M fluorine-18(1-) Chemical compound [18F-] KRHYYFGTRYWZRS-BJUDXGSMSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0404—Lipids, e.g. triglycerides; Polycationic carriers
- A61K51/0406—Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0491—Sugars, nucleosides, nucleotides, oligonucleotides, nucleic acids, e.g. DNA, RNA, nucleic acid aptamers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0422004.2 | 2004-10-05 | ||
| GBGB0422004.2A GB0422004D0 (en) | 2004-10-05 | 2004-10-05 | Method of deprotection |
| PCT/GB2005/003692 WO2006037950A1 (en) | 2004-10-05 | 2005-09-23 | Method of deprotection |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101035755A CN101035755A (zh) | 2007-09-12 |
| CN101035755B true CN101035755B (zh) | 2011-12-21 |
Family
ID=33428035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2005800338074A Expired - Fee Related CN101035755B (zh) | 2004-10-05 | 2005-09-23 | 脱保护的方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7714115B2 (enExample) |
| EP (1) | EP1797029A1 (enExample) |
| JP (1) | JP5000521B2 (enExample) |
| CN (1) | CN101035755B (enExample) |
| GB (1) | GB0422004D0 (enExample) |
| WO (1) | WO2006037950A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070260267A1 (en) * | 2002-10-07 | 2007-11-08 | Nicoson Zachary R | Localizing obturator |
| KR101497406B1 (ko) * | 2006-12-21 | 2015-03-02 | 니혼 메디피직스 가부시키가이샤 | 방사성 화상 진단제 |
| JP5518337B2 (ja) | 2006-12-27 | 2014-06-11 | 日本メジフィジックス株式会社 | 放射性ハロゲン標識有機化合物の前駆体化合物の製造方法 |
| CN101636183B (zh) * | 2007-02-13 | 2014-03-19 | 日本医事物理股份有限公司 | 放射性诊断显像剂的制备方法 |
| EP2005970A1 (de) | 2007-06-22 | 2008-12-24 | Berlin Science Partners GmbH i.V. | Bildgebende Diagnostik durch Kombination von Kontrastmitteln |
| US8043316B2 (en) | 2008-05-02 | 2011-10-25 | Suros Surgical Systems, Inc. | Adjustable spacer |
| GB0905515D0 (en) * | 2009-03-31 | 2009-05-13 | Ge Healthcare Ltd | Radiolabelling methods |
| EP2501663A2 (en) * | 2009-11-17 | 2012-09-26 | Piramal Imaging SA | Method for production of f-18 labeled glutamic acid derivatives |
| EP2582713A1 (en) * | 2010-06-17 | 2013-04-24 | MSD Oss B.V. | (11 beta,17 alpha)-11-(4-(2-11c-acetyl)phenyl)-17,23-epoxy-19,24-dinorchola-4,9,20-trien-3-one |
| KR20130132892A (ko) * | 2010-12-29 | 2013-12-05 | 지이 헬쓰케어 리미티드 | 용리제 용액 |
| US9101895B2 (en) | 2011-04-15 | 2015-08-11 | General Electric Company | System for mixing and dispersing microbubble pharmaceuticals |
| KR101221483B1 (ko) * | 2011-05-13 | 2013-01-16 | 서강대학교산학협력단 | Ｆ-18 표지 방사성의약품 합성 장치 및 방법 |
| GB201411569D0 (en) | 2014-06-30 | 2014-08-13 | Ge Healthcare Ltd | Novel formulation and method of synthesis |
| US11534494B2 (en) | 2011-12-21 | 2022-12-27 | Ge Healthcare Limited | Formulation and method of synthesis |
| RU2623163C2 (ru) * | 2011-12-21 | 2017-06-22 | ДжиИ ХЕЛТКЕР ЛИМИТЕД | Композиция 18f- флуцикловина в цитратных буферах |
| EP3151751A4 (en) * | 2014-06-06 | 2018-02-21 | The Regents of the University of California | Self-shielded, benchtop chemistry system |
| LT3481804T (lt) | 2016-06-10 | 2025-02-25 | The Johns Hopkins University | Radioaktyviai pažymėto prostatos specifinio membranos antigeno (psma) inhibitoriaus [18f]dcfpyl pagerinta sintezė |
| ES2916840T3 (es) * | 2016-12-07 | 2022-07-06 | Univ Degli Studi Di Bari Aldo Moro | Formulaciones estables de F-DOPA y usos de las mismas |
| JP7159157B2 (ja) * | 2017-06-23 | 2022-10-24 | 日本メジフィジックス株式会社 | 放射性フッ素標識化合物の製造方法および放射性医薬の製造方法 |
| WO2022196734A1 (ja) * | 2021-03-17 | 2022-09-22 | Tdk株式会社 | 含フッ素化合物および造影剤 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5135683A (en) * | 1991-03-28 | 1992-08-04 | Arco Chemical Technology, L.P. | Process for producing a deprotected alkoxylated polyol |
| US5393908A (en) | 1992-06-25 | 1995-02-28 | Satyamurthy; Nagichettiar | Synthesis of N-formyl-3,4-di-t-butoxycarbonyloxy-6-(trimethylstannyl)-L-phenylalanine ethyl ester and its regioselective radiofluorodestannylation to 6-[18 F]fluoro-L-dopa |
| DE4330889C2 (de) * | 1993-09-11 | 2002-10-31 | Emtec Magnetics Gmbh | Verfahren zur Wiedergewinnung von Rohmaterialien aus magnetischen Aufzeichnungsträgern |
| US5922810A (en) * | 1995-07-31 | 1999-07-13 | Fmc Corporation | Deprotection of protected functional polymers |
| BE1010280A3 (fr) * | 1996-05-02 | 1998-05-05 | Coincidence S A | Procede et dispositif de synthese de 2-[18f] fluoro-2-deoxy-d-glucose. |
| DE10104250A1 (de) * | 2001-01-31 | 2002-08-14 | Deutsches Krebsforsch | Markierungsfähige Verbindungen zur einfachen Synthese von 3'-[18F]Fluor-3'-deoxythymidin und Verfahren zu deren Herstellung |
| EP1356827A1 (en) | 2002-04-24 | 2003-10-29 | Mallinckrodt Inc. | Method for obtaining a 2-18F-fluor-2-deoxy-D-glucose (18F-FDG)-solution |
| US7022872B2 (en) * | 2003-12-19 | 2006-04-04 | Molecular Technologies, Inc. | Method for making fluorine labeled L-Dopa |
-
2004
- 2004-10-05 GB GBGB0422004.2A patent/GB0422004D0/en not_active Ceased
-
2005
- 2005-09-23 CN CN2005800338074A patent/CN101035755B/zh not_active Expired - Fee Related
- 2005-09-23 WO PCT/GB2005/003692 patent/WO2006037950A1/en not_active Ceased
- 2005-09-23 US US11/576,625 patent/US7714115B2/en not_active Expired - Fee Related
- 2005-09-23 EP EP05784549A patent/EP1797029A1/en not_active Withdrawn
- 2005-09-23 JP JP2007534071A patent/JP5000521B2/ja not_active Expired - Fee Related
Non-Patent Citations (7)
| Title |
|---|
| Bryan Li 等.Aqueous phosphoric acid as a mild reagent fordeprotection of the t-butoxycarbonyl group,8113-8115.Tetrahedron Letters44 44.2003,44(44),表一. * |
| BryanLi等.Aqueousphosphoricacidasamildreagentfordeprotectionofthet-butoxycarbonylgroup 8113-8115.Tetrahedron Letters44 44.2003 |
| K. Hamacher等.Efficient Stereospecific Synthesis of No-Carrier-Added 2-[18F]-Fluoro-2-Deoxy-D-Glucose Using AminopolyetherSupported Nucleophilic Substitution,235-238.J. Nucl. Med.27 2.1986,34(2),全文. |
| K. Hamacher等.Efficient Stereospecific Synthesis of No-Carrier-Added 2-[18F]-Fluoro-2-Deoxy-D-Glucose Using AminopolyetherSupported Nucleophilic Substitution,235-238.J. Nucl. Med.27 2.1986,34(2),全文. * |
| WO 94/00460 A1,全文. |
| Yu Shin Ding等.Synthesis of high specific activity 6-[18F] fluorodopaminefor positron emission tomography studies ofsympathetic nervous tissue,861-863.J. Med. Chem.34 2.1991,34(2),全文. |
| Yu Shin Ding等.Synthesis of high specific activity 6-[18F] fluorodopaminefor positron emission tomography studies ofsympathetic nervous tissue,861-863.J. Med. Chem.34 2.1991,34(2),全文. * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080076914A1 (en) | 2008-03-27 |
| US7714115B2 (en) | 2010-05-11 |
| WO2006037950A1 (en) | 2006-04-13 |
| EP1797029A1 (en) | 2007-06-20 |
| GB0422004D0 (en) | 2004-11-03 |
| CN101035755A (zh) | 2007-09-12 |
| JP5000521B2 (ja) | 2012-08-15 |
| JP2008515793A (ja) | 2008-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101035755B (zh) | 脱保护的方法 | |
| EP3663307A1 (en) | Production method for radiolabeled aryl compound | |
| BR112012021406B1 (pt) | Processos para a síntese dos compostos de diariltioidantoína e diarilidantoína | |
| HRP20120154T1 (hr) | HETEROCIKLIČKI INHIBITORI MEK-a I METODE NJIHOVE UPORABE | |
| EP2128130B1 (en) | Process for production of precursor compound for radioactive halogen-labeled organic compound | |
| CN105503872A (zh) | 一种利格列汀杂质及其制备方法和应用 | |
| CN104762666A (zh) | 双重运行盒 | |
| EP2455372B1 (en) | Process for producing crystals of polymorphic 2-(3-cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylic acid by poor-solvent addition method | |
| Shimizu et al. | Convenient method for the preparation of carbamates, carbonates, and thiocarbonates | |
| US9650410B2 (en) | Process for the preparation of abiraterone and abiraterone acetate | |
| CN106478597A (zh) | 富马酸沃诺拉赞单晶及其制备方法和用途 | |
| Sun et al. | Pre-activation based, highly alpha-selective O-sialylation with N-acetyl-5-N, 4-O-carbonyl-protected p-tolyl thiosialoside donor | |
| CN101560190B (zh) | 缬沙坦中杂质e的研究及控制方法 | |
| EP1742922B1 (en) | Crystalline pyrazole derivative | |
| EP2327395A1 (en) | Process for the preparation of gadobenate dimeglumine complex in a solid form | |
| CN101735164A (zh) | 缬沙坦中杂质f的研究及控制方法 | |
| CN101492419B (zh) | 氨溴索盐 | |
| CN109810065A (zh) | 一种恶拉戈利的合成方法 | |
| Hengeveld et al. | Facile N-demethylation of erythromycins | |
| DK2646411T3 (en) | PREPARATION OF PET PRECURSOR | |
| JP2004511548A (ja) | Ｎ−置換された２−スルファニルイミダゾールの調製方法 | |
| Guesmi et al. | Mechanochemical Promoted Heterocycles: A Solvent-free Route to Triazole Carbohydrates as Glycogen Phosphorylase Inhibitors | |
| KR101904565B1 (ko) | 1-아미노-3-히드록시-시클로부탄-1-카르복실산 유도체의 제조 | |
| Hilko et al. | Operationally Simple Regioselective 5′-Phosphorylation of Unprotected 5-Ethynyl-2′-deoxyuridine Analogues | |
| CN105085405A (zh) | 4-[1-甲基-5-(2-氯乙基-2-羟乙基)胺基-2-苯并咪唑基]丁酸盐酸盐的制备方法与应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20111221 Termination date: 20150923 |
|
| EXPY | Termination of patent right or utility model |