NL1004346C2 - Werkwijze voor het scheiden van een mengsel van enantiomeren in een geschikt oplosmiddel. - Google Patents
Werkwijze voor het scheiden van een mengsel van enantiomeren in een geschikt oplosmiddel. Download PDFInfo
- Publication number
- NL1004346C2 NL1004346C2 NL1004346A NL1004346A NL1004346C2 NL 1004346 C2 NL1004346 C2 NL 1004346C2 NL 1004346 A NL1004346 A NL 1004346A NL 1004346 A NL1004346 A NL 1004346A NL 1004346 C2 NL1004346 C2 NL 1004346C2
- Authority
- NL
- Netherlands
- Prior art keywords
- mixture
- enantiomers
- optically active
- agents
- diastereomer
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 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 42
- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000002904 solvent Substances 0.000 title claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 72
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 18
- 150000007513 acids Chemical class 0.000 claims description 12
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 238000003776 cleavage reaction Methods 0.000 description 9
- 230000007017 scission Effects 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 6
- -1 boiling point Chemical class 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 235000002906 tartaric acid Nutrition 0.000 description 6
- ZPSPULCZMWMHCY-JTQLQIEISA-N (4r)-4-(2-chlorophenyl)-2-hydroxy-5,5-dimethyl-1,3,2$l^{5}-dioxaphosphinane 2-oxide Chemical compound CC1(C)COP(O)(=O)O[C@H]1C1=CC=CC=C1Cl ZPSPULCZMWMHCY-JTQLQIEISA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004296 chiral HPLC Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- PSZSDCWNBXVDFG-UHFFFAOYSA-N 2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2$l^{5}-dioxaphosphinane 2-oxide Chemical compound CC1(C)COP(O)(=O)OC1C1=CC=CC=C1 PSZSDCWNBXVDFG-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UXLDFTUCNFDMOT-UHFFFAOYSA-N 2,3-dihydroxy-2-(2-methylbenzoyl)butanedioic acid Chemical compound CC1=CC=CC=C1C(=O)C(O)(C(O)C(O)=O)C(O)=O UXLDFTUCNFDMOT-UHFFFAOYSA-N 0.000 description 3
- CKESBQSMUJEOSP-UHFFFAOYSA-N 2,3-dihydroxy-2-(4-methylbenzoyl)butanedioic acid Chemical compound CC1=CC=C(C(=O)C(O)(C(O)C(O)=O)C(O)=O)C=C1 CKESBQSMUJEOSP-UHFFFAOYSA-N 0.000 description 3
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 150000003016 phosphoric acids Chemical class 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HXTGXYRHXAGCFP-OAQYLSRUSA-N (r)-(2,3-dimethoxyphenyl)-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]methanol Chemical compound COC1=CC=CC([C@H](O)C2CCN(CCC=3C=CC(F)=CC=3)CC2)=C1OC HXTGXYRHXAGCFP-OAQYLSRUSA-N 0.000 description 2
- IAJFCAIBAPJCDA-UHFFFAOYSA-N 2,3-dihydroxy-2-(4-methoxybenzoyl)butanedioic acid Chemical compound COC1=CC=C(C(=O)C(O)(C(O)C(O)=O)C(O)=O)C=C1 IAJFCAIBAPJCDA-UHFFFAOYSA-N 0.000 description 2
- OOKSMYZBWRKRGU-UHFFFAOYSA-N 2-benzoyl-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)(C(O)=O)C(=O)C1=CC=CC=C1 OOKSMYZBWRKRGU-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 1
- WLPVFKXJHBTYJG-UHFFFAOYSA-N (2-methoxyphenyl)-methyl-phenylphosphane Chemical compound COC1=CC=CC=C1P(C)C1=CC=CC=C1 WLPVFKXJHBTYJG-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- VPUSWNUKNDRGNW-UHFFFAOYSA-N 1-phenylpiperidin-3-ol Chemical compound C1C(O)CCCN1C1=CC=CC=C1 VPUSWNUKNDRGNW-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 101100139845 Caenorhabditis elegans rac-2 gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005094 computer simulation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910021432 inorganic complex Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000005425 toluyl group Chemical group 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)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1004346A NL1004346C2 (nl) | 1996-10-23 | 1996-10-23 | Werkwijze voor het scheiden van een mengsel van enantiomeren in een geschikt oplosmiddel. |
| NO974779A NO974779L (no) | 1996-10-23 | 1997-10-16 | FremgangsmÕte for separasjon av en blanding av enantiomere |
| DE69728730T DE69728730T9 (de) | 1996-10-23 | 1997-10-20 | Verfahren für die Trennung einer Enantiomermischung |
| IN2350MA1997 IN184142B (https=) | 1996-10-23 | 1997-10-20 | |
| EP97203262A EP0838448B1 (en) | 1996-10-23 | 1997-10-20 | Process for the separation of a mixture of enantiomers |
| AT97203262T ATE264826T1 (de) | 1996-10-23 | 1997-10-20 | Verfahren zur trennung einer enantiomermischung |
| CA002218804A CA2218804A1 (en) | 1996-10-23 | 1997-10-21 | Process for the separation of a mixture of enantiomers |
| IL12201297A IL122012A (en) | 1996-10-23 | 1997-10-21 | Process for the separation of mixtures of enantiomers with optically active resolving agents from a diastereomeric complex |
| US08/955,612 US6235927B1 (en) | 1996-10-23 | 1997-10-22 | Process for the separation of a mixture of enantiomers |
| JP9326871A JPH10245368A (ja) | 1996-10-23 | 1997-10-23 | 鏡像体混合物の分離方法 |
| CN97122879A CN1182068A (zh) | 1996-10-23 | 1997-10-23 | 对映体混合物的分离方法 |
| US09/784,083 US6465684B2 (en) | 1996-10-23 | 2001-02-16 | Process for the separation of a mixture of enantiomers |
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 |
|---|---|
| NL1004346C2 true NL1004346C2 (nl) | 1998-04-24 |
Family
ID=19763731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1004346A NL1004346C2 (nl) | 1996-10-23 | 1996-10-23 | Werkwijze voor het scheiden van een mengsel van enantiomeren in een geschikt oplosmiddel. |
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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL1008911C2 (nl) * | 1998-04-17 | 1999-10-19 | Dsm Nv | Werkwijze voor het verhogen van de enantiomere overmaat van een chirale verbinding. |
Families Citing this family (26)
| 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 |
| 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 |
| BRPI0916197B1 (pt) | 2008-07-29 | 2018-01-23 | Poxel | Processo para isolar componentes enantioméricos de uma mistura de enantiômeros |
| 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 |
| 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 |
| 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 |
| CN104829459B (zh) * | 2015-05-06 | 2017-05-24 | 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 |
| KR102565407B1 (ko) * | 2016-01-04 | 2023-08-10 | (주)아모레퍼시픽 | 극성 비양자성 용매를 이용한 n-[4-(1-아미노에틸)-페닐]-술폰아미드 유도체의 카이랄 분할 방법 |
| 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 |
| 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
Non-Patent Citations (3)
| Title |
|---|
| A. D. VAN DER HAEST ET AL: "Towards a rational design for resolving agents. Part V. Substituent effects in the resolution of ephedrine using a series of cyclic phosphoric acids", RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, vol. 112, March 1993 (1993-03-01), AMSTERDAM NL, pages 230 - 235, XP002032218 * |
| A. D. VAN DER HAEST ET AL: "Towards a rational design of resolving agents. Part II. Correlation between resolution results and physical properties of diastereomeric salts", RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, vol. 109, October 1990 (1990-10-01), AMSTERDAM NL, pages 523 - 528, XP002032219 * |
| J JACQUES ET AL: "Enantiomers, Racemates, and Resolutions", 1981, KRIEGER, MALABAR, FLORIDA, XP002032220 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL1008911C2 (nl) * | 1998-04-17 | 1999-10-19 | Dsm Nv | Werkwijze voor het verhogen van de enantiomere overmaat van een chirale verbinding. |
Also Published As
| Publication number | Publication date |
|---|---|
| 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 |
| CN1182068A (zh) | 1998-05-20 |
| EP0838448A1 (en) | 1998-04-29 |
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Legal Events
| Date | Code | Title | Description |
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| PD2B | A search report has been drawn up | ||
| VD1 | Lapsed due to non-payment of the annual fee |
Effective date: 20010501 |