CN1182068A - 对映体混合物的分离方法 - Google Patents
对映体混合物的分离方法 Download PDFInfo
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- CN1182068A CN1182068A CN97122879A CN97122879A CN1182068A CN 1182068 A CN1182068 A CN 1182068A CN 97122879 A CN97122879 A CN 97122879A CN 97122879 A CN97122879 A CN 97122879A CN 1182068 A CN1182068 A CN 1182068A
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- mixture
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- pea
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- resolving agent
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- 238000000034 method Methods 0.000 title claims abstract description 48
- 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 claims abstract description 37
- 238000000926 separation method Methods 0.000 title claims abstract description 22
- 239000000203 mixture Substances 0.000 title claims description 188
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 90
- 150000003839 salts Chemical group 0.000 claims description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 69
- 150000001412 amines Chemical class 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 26
- 150000001413 amino acids Chemical class 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 150000001414 amino alcohols Chemical class 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 238000004128 high performance liquid chromatography Methods 0.000 description 44
- 238000005194 fractionation Methods 0.000 description 43
- 239000002253 acid Substances 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
- -1 N-benzyloxy carbonylamino Chemical group 0.000 description 33
- 238000001953 recrystallisation Methods 0.000 description 32
- 229960002510 mandelic acid Drugs 0.000 description 29
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- 238000002474 experimental method Methods 0.000 description 21
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 15
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 15
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- 125000000217 alkyl group Chemical group 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
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- 238000002425 crystallisation Methods 0.000 description 12
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 12
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- ZPSPULCZMWMHCY-JTQLQIEISA-N (4r)-4-(2-chlorophenyl)-2-hydroxy-5,5-dimethyl-1,3,2$l^{5}-dioxaphosphinane 2-oxide Chemical compound CC1(C)COP(O)(=O)O[C@H]1C1=CC=CC=C1Cl ZPSPULCZMWMHCY-JTQLQIEISA-N 0.000 description 10
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- 239000002585 base Substances 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- OWVIRVJQDVCGQX-VSGBNLITSA-N [(4r,5r)-5-[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-diphenylmethanol Chemical class C=1C=CC=CC=1C(O)([C@H]1[C@@H](OC(O1)(C)C)C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OWVIRVJQDVCGQX-VSGBNLITSA-N 0.000 description 7
- 229940095064 tartrate Drugs 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- PSZSDCWNBXVDFG-SNVBAGLBSA-N (4r)-2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2$l^{5}-dioxaphosphinane 2-oxide Chemical compound CC1(C)COP(O)(=O)O[C@@H]1C1=CC=CC=C1 PSZSDCWNBXVDFG-SNVBAGLBSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 5
- 229960004895 bretylium tosylate Drugs 0.000 description 5
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- 229960000948 quinine Drugs 0.000 description 5
- 230000006340 racemization Effects 0.000 description 5
- 238000012216 screening Methods 0.000 description 5
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- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 4
- LUMNWCHHXDUKFI-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethanol Chemical compound C1C2C(CO)CC1C=C2 LUMNWCHHXDUKFI-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- LABRPRANVKSMGP-UHFFFAOYSA-N 1,3,2-dioxaphosphinane Chemical compound C1COPOC1 LABRPRANVKSMGP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KWGRBVOPPLSCSI-PSASIEDQSA-N (1s,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-PSASIEDQSA-N 0.000 description 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 2
- LEBDCRNSLNAHHD-JTQLQIEISA-N (2s)-2-amino-2-methyl-3-phenylpropanamide Chemical class NC(=O)[C@](N)(C)CC1=CC=CC=C1 LEBDCRNSLNAHHD-JTQLQIEISA-N 0.000 description 2
- KIYRSYYOVDHSPG-ZETCQYMHSA-N (2s)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-ZETCQYMHSA-N 0.000 description 2
- ZPSPULCZMWMHCY-SNVBAGLBSA-N (4s)-4-(2-chlorophenyl)-2-hydroxy-5,5-dimethyl-1,3,2$l^{5}-dioxaphosphinane 2-oxide Chemical compound CC1(C)COP(O)(=O)O[C@@H]1C1=CC=CC=C1Cl ZPSPULCZMWMHCY-SNVBAGLBSA-N 0.000 description 2
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 2
- AQFLVLHRZFLDDV-UHFFFAOYSA-N 1-phenylpropan-1-amine Chemical compound CCC(N)C1=CC=CC=C1 AQFLVLHRZFLDDV-UHFFFAOYSA-N 0.000 description 2
- UVXXBSCXKKIBCH-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-amine Chemical compound CC(C)C(N)C1=CC=CC=C1 UVXXBSCXKKIBCH-UHFFFAOYSA-N 0.000 description 2
- UJOYFRCOTPUKAK-UHFFFAOYSA-N 3-ammonio-3-phenylpropanoate Chemical compound [O-]C(=O)CC([NH3+])C1=CC=CC=C1 UJOYFRCOTPUKAK-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
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- HYOWVAAEQCNGLE-JTQLQIEISA-N alpha-methyl-L-phenylalanine Chemical compound OC(=O)[C@](N)(C)CC1=CC=CC=C1 HYOWVAAEQCNGLE-JTQLQIEISA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
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- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
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- ZEIHKBVDOZJPRM-UHFFFAOYSA-N ethylbenzene;methanamine Chemical compound NC.CCC1=CC=CC=C1 ZEIHKBVDOZJPRM-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000001511 high performance liquid chromatography nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- QADHFBHNTDGUJQ-UHFFFAOYSA-N n-bromo-2-phenylethanamine Chemical compound BrNCCC1=CC=CC=C1 QADHFBHNTDGUJQ-UHFFFAOYSA-N 0.000 description 1
- PIWRNJHNOGWIMX-UHFFFAOYSA-N n-chloro-2-phenylethanamine Chemical compound ClNCCC1=CC=CC=C1 PIWRNJHNOGWIMX-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/80—Preparation of compounds containing amino groups bound to a carbon skeleton by photochemical reactions; by using free radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/34—Preparation of optical isomers by separation of optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1004346 | 1996-10-23 | ||
| NL1004346A NL1004346C2 (nl) | 1996-10-23 | 1996-10-23 | Werkwijze voor het scheiden van een mengsel van enantiomeren in een geschikt oplosmiddel. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1182068A true CN1182068A (zh) | 1998-05-20 |
Family
ID=19763731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97122879A Pending CN1182068A (zh) | 1996-10-23 | 1997-10-23 | 对映体混合物的分离方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6235927B1 (https=) |
| EP (1) | EP0838448B1 (https=) |
| JP (1) | JPH10245368A (https=) |
| CN (1) | CN1182068A (https=) |
| AT (1) | ATE264826T1 (https=) |
| CA (1) | CA2218804A1 (https=) |
| DE (1) | DE69728730T9 (https=) |
| IL (1) | IL122012A (https=) |
| IN (1) | IN184142B (https=) |
| NL (1) | NL1004346C2 (https=) |
| NO (1) | NO974779L (https=) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101792398A (zh) * | 2010-03-09 | 2010-08-04 | 河北科技大学 | 一种拆分法制备光学纯对羟基苯甘氨酸的方法 |
| CN102112425A (zh) * | 2008-07-29 | 2011-06-29 | 普克塞尔公司 | 通过控制粒径的结晶从对映体混合物中分离对映体组分的方法 |
| CN104829459A (zh) * | 2015-05-06 | 2015-08-12 | 河北凯力昂生物科技有限公司 | 一种拆分法制备(r)-(+)-1-萘乙胺的方法 |
| CN104876856A (zh) * | 2015-05-05 | 2015-09-02 | 河北凯力昂生物科技有限公司 | 一种拆分法制备(r)-(+)-3-氨基哌啶二盐酸盐的方法 |
| CN108658784A (zh) * | 2018-04-26 | 2018-10-16 | 联化科技股份有限公司 | (r)-1-(4-甲基苯基)乙胺的合成方法 |
| CN109485561A (zh) * | 2018-11-23 | 2019-03-19 | 江苏颖盛化工有限公司 | 一种dl-萘普生的合成工艺 |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999042460A1 (en) * | 1998-02-20 | 1999-08-26 | Fine Chemicals Corporation (Proprietary) Limited | Process for the production of optically enriched (r)- or (s)-albuterol |
| US6713627B2 (en) | 1998-03-13 | 2004-03-30 | Aventis Pharmaceuticals Inc. | Processes for the preparation of (R)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol |
| NL1008911C2 (nl) * | 1998-04-17 | 1999-10-19 | Dsm Nv | Werkwijze voor het verhogen van de enantiomere overmaat van een chirale verbinding. |
| EP1034826A1 (en) | 1999-03-05 | 2000-09-13 | Reuter Chemische Apparatebau | Co-crystallization process |
| NL1012865C2 (nl) * | 1999-08-19 | 2001-02-20 | Dsm Nv | 1-Fenyl-3-oxopropaan-1-sulfonzuren en -sulfonaten en zuivere enantiomeren daarvan. |
| WO2001030763A1 (en) * | 1999-10-22 | 2001-05-03 | Takeda Chemical Industries, Ltd. | Process for producing optically active naphthalene derivative and optical resolver therefor |
| US7666588B2 (en) * | 2001-03-02 | 2010-02-23 | Ibis Biosciences, Inc. | Methods for rapid forensic analysis of mitochondrial DNA and characterization of mitochondrial DNA heteroplasmy |
| JP2005104895A (ja) * | 2003-09-30 | 2005-04-21 | Nippon Kayaku Co Ltd | 光学活性なアミノアルコール化合物の製造法 |
| ATE361905T1 (de) * | 2003-12-10 | 2007-06-15 | Degussa | Verfahren zur herstellung von enantiomeren angereicherten aminosäuren |
| EP1720861A2 (en) | 2004-02-25 | 2006-11-15 | Eli Lilly And Company | Histamine h3 receptor antagonists, preparation and therapeutic uses |
| WO2006006071A1 (en) * | 2004-07-07 | 2006-01-19 | Pfizer Products Inc. | Resolution of an aryl-fused azapolycyclic compound |
| EP1885692A2 (en) * | 2005-05-04 | 2008-02-13 | Medichem, S.A. | Process for the preparation of tamsulosin |
| MX2007016216A (es) | 2005-07-01 | 2008-03-11 | Lilly Co Eli | Agenes del receptor de histamina h3, preparacion y usos terapeuticos. |
| ES2393757T3 (es) | 2005-11-17 | 2012-12-27 | Eli Lilly & Company | Antagonistas de receptor de glucagón, preparación y usos terapéuticos |
| WO2007114855A2 (en) | 2005-11-18 | 2007-10-11 | Eli Lilly And Company | Glucagon receptor antagonists, preparation and therapeutic uses |
| UA99284C2 (ru) | 2007-05-11 | 2012-08-10 | Елі Ліллі Енд Компані | ИНГИБИТОРЫ р70 S6-КИНАЗЫ |
| AR075988A1 (es) | 2009-04-09 | 2011-05-11 | Lilly Co Eli | Compuesto de piridiloxi - pirrolidina inhibidor de recaptacion de serotonina y norepinefrina, composicion farmaceutica que lo comprende y su uso para la manufactura de un medicamento util para el tratamiento de dolor cronico |
| EA020151B1 (ru) | 2009-10-23 | 2014-09-30 | Эли Лилли Энд Компани | Ингибиторы akt и фармацевтические составы, их содержащие |
| KR102565407B1 (ko) * | 2016-01-04 | 2023-08-10 | (주)아모레퍼시픽 | 극성 비양자성 용매를 이용한 n-[4-(1-아미노에틸)-페닐]-술폰아미드 유도체의 카이랄 분할 방법 |
| WO2021074778A1 (en) * | 2019-10-16 | 2021-04-22 | Hikal Limited | An industrial process for resolution of chlocyphos |
| US20260015329A1 (en) * | 2022-07-14 | 2026-01-15 | Kureha Corporation | Method for producing triazole derivative enantiomer (r) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB656500A (en) * | 1947-10-24 | 1951-08-22 | Sterling Drug Inc | Improvements in or relating to the preparation of l-arterenol and l-arterenol so prepared |
| US3862985A (en) * | 1971-07-28 | 1975-01-28 | Allied Chem | Resolution of lysineamide |
| WO1985003932A1 (en) * | 1984-03-01 | 1985-09-12 | Alkaloida Vegyészeti Gyár | Novel diastereomer salts of phenylalanine and n-acyl derivatives thereof and process for the separation of optically active phenylalanine and n-acyl derivatives thereof |
-
1996
- 1996-10-23 NL NL1004346A patent/NL1004346C2/nl not_active IP Right Cessation
-
1997
- 1997-10-16 NO NO974779A patent/NO974779L/no not_active Application Discontinuation
- 1997-10-20 DE DE69728730T patent/DE69728730T9/de active Active
- 1997-10-20 EP EP97203262A patent/EP0838448B1/en not_active Expired - Lifetime
- 1997-10-20 AT AT97203262T patent/ATE264826T1/de not_active IP Right Cessation
- 1997-10-20 IN IN2350MA1997 patent/IN184142B/en unknown
- 1997-10-21 CA CA002218804A patent/CA2218804A1/en not_active Abandoned
- 1997-10-21 IL IL12201297A patent/IL122012A/xx not_active IP Right Cessation
- 1997-10-22 US US08/955,612 patent/US6235927B1/en not_active Expired - Fee Related
- 1997-10-23 CN CN97122879A patent/CN1182068A/zh active Pending
- 1997-10-23 JP JP9326871A patent/JPH10245368A/ja active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102112425A (zh) * | 2008-07-29 | 2011-06-29 | 普克塞尔公司 | 通过控制粒径的结晶从对映体混合物中分离对映体组分的方法 |
| CN102112425B (zh) * | 2008-07-29 | 2014-06-11 | 普克塞尔公司 | 通过控制粒径的结晶从对映体混合物中分离对映体组分的方法 |
| CN101792398A (zh) * | 2010-03-09 | 2010-08-04 | 河北科技大学 | 一种拆分法制备光学纯对羟基苯甘氨酸的方法 |
| CN101792398B (zh) * | 2010-03-09 | 2013-06-26 | 河北科技大学 | 一种拆分法制备光学纯对羟基苯甘氨酸的方法 |
| CN104876856A (zh) * | 2015-05-05 | 2015-09-02 | 河北凯力昂生物科技有限公司 | 一种拆分法制备(r)-(+)-3-氨基哌啶二盐酸盐的方法 |
| CN104876856B (zh) * | 2015-05-05 | 2017-11-21 | 河北凯力昂生物科技有限公司 | 一种拆分法制备(r)‑(+)‑3‑氨基哌啶二盐酸盐的方法 |
| CN104829459A (zh) * | 2015-05-06 | 2015-08-12 | 河北凯力昂生物科技有限公司 | 一种拆分法制备(r)-(+)-1-萘乙胺的方法 |
| CN108658784A (zh) * | 2018-04-26 | 2018-10-16 | 联化科技股份有限公司 | (r)-1-(4-甲基苯基)乙胺的合成方法 |
| CN108658784B (zh) * | 2018-04-26 | 2020-12-18 | 联化科技股份有限公司 | (r)-1-(4-甲基苯基)乙胺的合成方法 |
| CN109485561A (zh) * | 2018-11-23 | 2019-03-19 | 江苏颖盛化工有限公司 | 一种dl-萘普生的合成工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL1004346C2 (nl) | 1998-04-24 |
| CA2218804A1 (en) | 1998-04-23 |
| ATE264826T1 (de) | 2004-05-15 |
| DE69728730D1 (de) | 2004-05-27 |
| EP0838448B1 (en) | 2004-04-21 |
| IL122012A (en) | 2001-08-26 |
| US6235927B1 (en) | 2001-05-22 |
| IN184142B (https=) | 2000-06-17 |
| JPH10245368A (ja) | 1998-09-14 |
| DE69728730T9 (de) | 2005-09-08 |
| NO974779L (no) | 1998-04-24 |
| DE69728730T2 (de) | 2005-03-31 |
| IL122012A0 (en) | 1998-03-10 |
| NO974779D0 (no) | 1997-10-16 |
| EP0838448A1 (en) | 1998-04-29 |
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