CA2784236C - Process for the resolution of enantiomers by preferential evaporative crystallization - Google Patents
Process for the resolution of enantiomers by preferential evaporative crystallization Download PDFInfo
- Publication number
- CA2784236C CA2784236C CA2784236A CA2784236A CA2784236C CA 2784236 C CA2784236 C CA 2784236C CA 2784236 A CA2784236 A CA 2784236A CA 2784236 A CA2784236 A CA 2784236A CA 2784236 C CA2784236 C CA 2784236C
- Authority
- CA
- Canada
- Prior art keywords
- solvent
- enantiomers
- enantiomer
- point
- crystals
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 64
- 238000002425 crystallisation Methods 0.000 title claims abstract description 52
- 230000008025 crystallization Effects 0.000 title claims abstract description 52
- 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 47
- 239000002904 solvent Substances 0.000 claims abstract description 89
- 239000000203 mixture Substances 0.000 claims abstract description 84
- 238000001704 evaporation Methods 0.000 claims abstract description 43
- 239000000725 suspension Substances 0.000 claims abstract description 24
- 239000013078 crystal Substances 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000001914 filtration Methods 0.000 claims description 22
- 238000010586 diagram Methods 0.000 claims description 17
- 239000012452 mother liquor Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000003306 harvesting Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000010899 nucleation Methods 0.000 claims description 8
- YHRUSWKIWCVSRL-UHFFFAOYSA-M sodium;2-(2-chlorophenyl)-2-hydroxyacetate Chemical compound [Na+].[O-]C(=O)C(O)C1=CC=CC=C1Cl YHRUSWKIWCVSRL-UHFFFAOYSA-M 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- JNGWGQUYLVSFND-UHFFFAOYSA-N 5-methyl-5-phenylimidazolidine-2,4-dione Chemical compound C=1C=CC=CC=1C1(C)NC(=O)NC1=O JNGWGQUYLVSFND-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012047 saturated solution Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 2
- 239000012456 homogeneous solution Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000006340 racemization Effects 0.000 claims 1
- 230000008020 evaporation Effects 0.000 abstract description 31
- 230000001939 inductive effect Effects 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 5
- 239000007790 solid phase Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006911 nucleation Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 description 1
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical class N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 238000000711 polarimetry Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0959170A FR2954310B1 (fr) | 2009-12-18 | 2009-12-18 | Procede de dedoublement d'enantiomeres par evapocristallisation preferentielle |
| FR0959170 | 2009-12-18 | ||
| US28855609P | 2009-12-21 | 2009-12-21 | |
| US61/288,556 | 2009-12-21 | ||
| PCT/EP2010/069860 WO2011073300A1 (en) | 2009-12-18 | 2010-12-16 | Process for the resolution of enantiomers by preferential evaporative crystallization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2784236A1 CA2784236A1 (en) | 2011-06-23 |
| CA2784236C true CA2784236C (en) | 2018-01-02 |
Family
ID=42396635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2784236A Active CA2784236C (en) | 2009-12-18 | 2010-12-16 | Process for the resolution of enantiomers by preferential evaporative crystallization |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8907106B2 (enExample) |
| EP (1) | EP2513017B1 (enExample) |
| CA (1) | CA2784236C (enExample) |
| FR (1) | FR2954310B1 (enExample) |
| IN (1) | IN2012DN06281A (enExample) |
| WO (1) | WO2011073300A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201417644D0 (en) * | 2014-10-06 | 2014-11-19 | Nucana Biomed Ltd | Method of separating phosphate diastereoisomers |
| CN108135920A (zh) | 2015-10-05 | 2018-06-08 | 努卡那有限公司 | 组合疗法 |
| GB201522771D0 (en) | 2015-12-23 | 2016-02-03 | Nucana Biomed Ltd | Crystalline form of a phosphate derivative |
| FR3054218B1 (fr) * | 2016-07-22 | 2020-03-06 | Universite De Rouen | Procede de dedoublement de sels de baclofene |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2710337B1 (fr) * | 1993-09-23 | 1995-12-08 | Gerard Coquerel | Procédé de dédoublement de deux antipodes optiques par entraînement polythermique programmé et autoensemencé. |
| FR2920428B1 (fr) | 2007-08-29 | 2012-06-15 | Univ Rouen | Procede de dedoublement de sels de l'omeprazole |
-
2009
- 2009-12-18 FR FR0959170A patent/FR2954310B1/fr not_active Expired - Fee Related
-
2010
- 2010-12-16 US US13/516,861 patent/US8907106B2/en active Active
- 2010-12-16 WO PCT/EP2010/069860 patent/WO2011073300A1/en not_active Ceased
- 2010-12-16 EP EP10798054.2A patent/EP2513017B1/en active Active
- 2010-12-16 IN IN6281DEN2012 patent/IN2012DN06281A/en unknown
- 2010-12-16 CA CA2784236A patent/CA2784236C/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2513017B1 (en) | 2015-07-01 |
| US20120259127A1 (en) | 2012-10-11 |
| FR2954310B1 (fr) | 2014-07-25 |
| CA2784236A1 (en) | 2011-06-23 |
| FR2954310A1 (fr) | 2011-06-24 |
| EP2513017A1 (en) | 2012-10-24 |
| IN2012DN06281A (enExample) | 2015-09-25 |
| US8907106B2 (en) | 2014-12-09 |
| WO2011073300A1 (en) | 2011-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20151123 |