JP4887286B2 - エナンチオマーの分離用組成物及び方法 - Google Patents
エナンチオマーの分離用組成物及び方法 Download PDFInfo
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- JP4887286B2 JP4887286B2 JP2007507444A JP2007507444A JP4887286B2 JP 4887286 B2 JP4887286 B2 JP 4887286B2 JP 2007507444 A JP2007507444 A JP 2007507444A JP 2007507444 A JP2007507444 A JP 2007507444A JP 4887286 B2 JP4887286 B2 JP 4887286B2
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- 238000000926 separation method Methods 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 28
- 239000000203 mixture Substances 0.000 title claims description 13
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title description 12
- 239000012071 phase Substances 0.000 claims description 78
- 238000004811 liquid chromatography Methods 0.000 claims description 14
- 239000012491 analyte Substances 0.000 claims description 12
- 238000010828 elution Methods 0.000 claims description 10
- 238000003981 capillary liquid chromatography Methods 0.000 claims description 8
- 239000000872 buffer Substances 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000005481 NMR spectroscopy Methods 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 238000004566 IR spectroscopy Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000004949 mass spectrometry Methods 0.000 claims description 3
- HDRLMQIFIIUDKM-LYKKTTPLSA-N (2s)-3-methyl-2-(2-methyldodecanoylamino)butanoic acid Chemical compound CCCCCCCCCCC(C)C(=O)N[C@@H](C(C)C)C(O)=O HDRLMQIFIIUDKM-LYKKTTPLSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 150000002085 enols Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000000105 evaporative light scattering detection Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- -1 C 1 -C 24 or more Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000010829 isocratic elution Methods 0.000 claims 1
- 230000005526 G1 to G0 transition Effects 0.000 description 19
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 239000000654 additive Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000003993 interaction Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000005251 capillar electrophoresis Methods 0.000 description 3
- 238000004296 chiral HPLC Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229960002179 ephedrine Drugs 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 2
- 229960003908 pseudoephedrine Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- ZKDOQFPDSUOLGF-UHFFFAOYSA-N 1-bromo-3-chloro-2-methylpropane Chemical compound ClCC(C)CBr ZKDOQFPDSUOLGF-UHFFFAOYSA-N 0.000 description 1
- IWAKWOFEHSYKSI-UHFFFAOYSA-N 1-chloro-2-methylbutane Chemical compound CCC(C)CCl IWAKWOFEHSYKSI-UHFFFAOYSA-N 0.000 description 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- HRMLMRIORGNUSV-UHFFFAOYSA-N 2-amino-2-(1-benzothiophen-3-yl)acetic acid Chemical compound C1=CC=C2C(C(C(O)=O)N)=CSC2=C1 HRMLMRIORGNUSV-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- PYNYHMRMZOGVML-UHFFFAOYSA-N 2-bromopropanenitrile Chemical compound CC(Br)C#N PYNYHMRMZOGVML-UHFFFAOYSA-N 0.000 description 1
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 1
- JNAYPRPPXRWGQO-UHFFFAOYSA-N 2-chloropropanenitrile Chemical compound CC(Cl)C#N JNAYPRPPXRWGQO-UHFFFAOYSA-N 0.000 description 1
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- XXZVBSPSFVERCB-UHFFFAOYSA-N 3-chloro-2-methylpropanenitrile Chemical compound ClCC(C)C#N XXZVBSPSFVERCB-UHFFFAOYSA-N 0.000 description 1
- BNPOTXLWPZOESZ-UHFFFAOYSA-N 4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCC(CCl)O1 BNPOTXLWPZOESZ-UHFFFAOYSA-N 0.000 description 1
- LHBPNZDUNCZWFL-UHFFFAOYSA-N 4-chloro-3-hydroxybutanenitrile Chemical compound ClCC(O)CC#N LHBPNZDUNCZWFL-UHFFFAOYSA-N 0.000 description 1
- HBOCDUIBOKBYST-UHFFFAOYSA-N ClC(C(C)=O)C.OC1CC(=O)OC1 Chemical compound ClC(C(C)=O)C.OC1CC(=O)OC1 HBOCDUIBOKBYST-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- MLHOXUWWKVQEJB-UHFFFAOYSA-N Propyleneglycol diacetate Chemical compound CC(=O)OC(C)COC(C)=O MLHOXUWWKVQEJB-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 238000004850 capillary HPLC Methods 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000012069 chiral reagent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001502 gel electrophoresis Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 1
- HQGPKMSGXAUKHT-UHFFFAOYSA-N methyl 5-oxopyrrolidine-2-carboxylate Chemical compound COC(=O)C1CCC(=O)N1 HQGPKMSGXAUKHT-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- AEIAMRMQKCPGJR-UHFFFAOYSA-N propane-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.CC(N)CN AEIAMRMQKCPGJR-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004808 supercritical fluid chromatography Methods 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
- B01D15/3833—Chiral chromatography
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/42—Selective adsorption, e.g. chromatography characterised by the development mode, e.g. by displacement or by elution
- B01D15/424—Elution mode
- B01D15/426—Specific type of solvent
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Description
を有するキラル分子に係る。
実施例
図1は、本発明のキラル移動を使用するエナンチオマー分子、(d,l)プソイドエフェドリン(pseudoephedrine)及び(d,l)エフェドリンの分離から得られたクロマトグラムを示す。この分離のために使用したカラムは、3.5μm、0.32mm×150mmエックステラ(Xterra)RP18(逆相C18カラム)であった。流量を5.0μL/分に設定した。カラム温度を25℃に設定した。注入したサンプル体積は、1.0μL(20ng)であった。2種の溶媒を使用した。溶離剤Aには、5%のTHFを有する25mMのs−ドデシルカルボニルバリン(s−DDCV)(pH7.0)が含まれ、溶離剤Bは、5%のTHFを有する25mM s−DDCV(pH11.0)であった。初期条件が15%溶離剤Bであり、30分間経過して溶離剤Bが85%である、勾配方法を使用した。
Claims (8)
- サンプル中に含有されている分析物の分離方法であって、前記サンプルが1種又は2種以上のエナンチオマー分析物を有し、
式:
を有するキラル移動相を有する試薬を用意する工程、
前記サンプルを分離のための手段の中に導入する工程及び
前記サンプルを前記キラル移動相と接触させて、混合物にする工程
を含み、
前記キラル移動相が、s−ドデシルカルボニルバリンを含む
ことを特徴とする、方法。 - 1種又は2種以上の関心のある分析物を検出する工程を更に含む、請求項1に記載の方法。
- 前記検出を、質量分析法、核磁気共鳴、紫外、屈折率、赤外分光法、蛍光、ホトダイオードアレー、蒸発性光散乱、コンダクタンス及び窒素/硫黄特異検出器を使用して達成する、請求項2に記載の方法。
- 前記分析物溶離順序を、前記キラル移動相を操作することによって逆転させる、請求項1に記載の方法。
- 前記水性相に、緩衝剤が更に含有されている、請求項1に記載の方法。
- 前記分離のための手段が、液体クロマトグラフィー及び毛細管液体クロマトグラフィーからなる群から選択される、請求項1に記載の方法。
- 前記分析物を分離するために、アイソクラチック溶離方法を使用する、請求項1に記載の方法。
- 前記分析物を分離するために、勾配溶離方法を使用する、請求項1に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US56007004P | 2004-04-07 | 2004-04-07 | |
US60/560,070 | 2004-04-07 | ||
PCT/US2005/011526 WO2005099855A1 (en) | 2004-04-07 | 2005-04-06 | Compositions and methods for separating enantiomers |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007532880A JP2007532880A (ja) | 2007-11-15 |
JP4887286B2 true JP4887286B2 (ja) | 2012-02-29 |
Family
ID=35149801
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007507444A Expired - Fee Related JP4887286B2 (ja) | 2004-04-07 | 2005-04-06 | エナンチオマーの分離用組成物及び方法 |
Country Status (5)
Country | Link |
---|---|
US (2) | US7628920B2 (ja) |
JP (1) | JP4887286B2 (ja) |
DE (1) | DE112005000772B4 (ja) |
GB (1) | GB2427374B (ja) |
WO (1) | WO2005099855A1 (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007112444A2 (en) | 2006-03-28 | 2007-10-04 | Georgia State University Research Foundation | Polymeric sulfated surfactants for capillary electrophoresis (ce) and ce-mass spectrometry (ce-ms) |
CN104237434B (zh) * | 2014-08-29 | 2016-01-20 | 中国农业科学院农产品加工研究所 | 一种检测食用油中3-氯-1,2-丙二醇酯含量的方法 |
CN105954456B (zh) * | 2016-07-18 | 2017-11-17 | 中国烟草总公司郑州烟草研究院 | 一种电子烟烟液中2‑丁酮的测定方法 |
CN107328874B (zh) * | 2017-06-28 | 2019-12-20 | 南京希麦迪医药科技有限公司 | 一种盐酸帕洛诺司琼光学异构体的拆分试剂及分离检测方法 |
CN107290453B (zh) * | 2017-06-29 | 2019-09-17 | 方达医药技术(上海)有限公司 | 盐酸帕洛诺司琼合成中间产物的hplc分析方法 |
CN113866289A (zh) * | 2021-09-03 | 2021-12-31 | 上海凌凯医药科技有限公司 | 2,3-二苯甲酰氧基-4-二甲基氨基-4-氧代丁酸的手性分离检测方法 |
CN113929083B (zh) * | 2021-11-12 | 2023-09-22 | 黑龙江省能源环境研究院 | 一种氮/硫掺杂多孔碳材料及其制备方法 |
CN115236236A (zh) * | 2022-07-26 | 2022-10-25 | 上海市食品药品检验研究院 | 一种利奈唑胺及其制剂中对映异构体的分离分析方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57176936A (en) * | 1981-04-23 | 1982-10-30 | Funakoshi Yakuhin Kk | Chromatographic separation of amino acid enanthiomer |
JPS6193145A (ja) * | 1984-10-15 | 1986-05-12 | Funakoshi Yakuhin Kk | アミノ酸エナンチオマ−のクロマトグラフイ−による分離法 |
US5338454A (en) * | 1992-08-27 | 1994-08-16 | Supelco, Incorporated | Chiral mobile phase additives for improved liquid-chromatography separations |
WO2003103575A2 (en) * | 2002-05-23 | 2003-12-18 | Cytokinetics, Inc. | Compounds, compositions, and methods |
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2005
- 2005-04-06 US US10/599,583 patent/US7628920B2/en not_active Expired - Fee Related
- 2005-04-06 WO PCT/US2005/011526 patent/WO2005099855A1/en active Application Filing
- 2005-04-06 DE DE112005000772.3T patent/DE112005000772B4/de not_active Expired - Fee Related
- 2005-04-06 JP JP2007507444A patent/JP4887286B2/ja not_active Expired - Fee Related
- 2005-04-06 GB GB0619491A patent/GB2427374B/en not_active Expired - Fee Related
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WO2003103575A2 (en) * | 2002-05-23 | 2003-12-18 | Cytokinetics, Inc. | Compounds, compositions, and methods |
Also Published As
Publication number | Publication date |
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DE112005000772B4 (de) | 2017-12-28 |
US20100065492A1 (en) | 2010-03-18 |
JP2007532880A (ja) | 2007-11-15 |
US7628920B2 (en) | 2009-12-08 |
DE112005000772T5 (de) | 2007-02-15 |
WO2005099855A1 (en) | 2005-10-27 |
GB2427374A (en) | 2006-12-27 |
US20080237130A1 (en) | 2008-10-02 |
GB2427374B (en) | 2009-02-25 |
GB0619491D0 (en) | 2006-11-15 |
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