GB2382074A - Recovery of chiral tartaric acid resolving agents - Google Patents
Recovery of chiral tartaric acid resolving agents Download PDFInfo
- Publication number
- GB2382074A GB2382074A GB0127346A GB0127346A GB2382074A GB 2382074 A GB2382074 A GB 2382074A GB 0127346 A GB0127346 A GB 0127346A GB 0127346 A GB0127346 A GB 0127346A GB 2382074 A GB2382074 A GB 2382074A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tartaric acid
- acid
- process according
- substituted
- resolving 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.)
- Withdrawn
Links
- 239000011975 tartaric acid Substances 0.000 title claims abstract description 36
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 30
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 235000002906 tartaric acid Nutrition 0.000 title claims abstract description 27
- 238000011084 recovery Methods 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 32
- 150000003892 tartrate salts Chemical class 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 239000008346 aqueous phase Substances 0.000 claims abstract description 14
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 9
- 239000011707 mineral Substances 0.000 claims abstract description 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical group CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000010268 HPLC based assay Methods 0.000 description 2
- STCJUTRPNGTJGE-UHFFFAOYSA-N [1-benzyl-4-(4-fluorophenyl)-3,6-dihydro-2h-pyridin-3-yl]methanol Chemical compound C1C=C(C=2C=CC(F)=CC=2)C(CO)CN1CC1=CC=CC=C1 STCJUTRPNGTJGE-UHFFFAOYSA-N 0.000 description 2
- -1 amine compounds Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- CEXCHYIGFUAPKW-UHFFFAOYSA-N methanol;piperidine Chemical class OC.C1CCNCC1 CEXCHYIGFUAPKW-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- UWEGHSOGEPMSGV-IUCAKERBSA-N (2S,3S)-2-hydroxy-3-(4-methylbenzoyl)oxybutanedioic acid Chemical compound CC1=CC=C(C(=O)O[C@@H]([C@H](O)C(O)=O)C(O)=O)C=C1 UWEGHSOGEPMSGV-IUCAKERBSA-N 0.000 description 1
- LSROBYZLBGODRN-UHFFFAOYSA-N 1-aminopyrrolidin-2-one Chemical class NN1CCCC1=O LSROBYZLBGODRN-UHFFFAOYSA-N 0.000 description 1
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical class C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- 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
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0127346A GB2382074A (en) | 2001-11-14 | 2001-11-14 | Recovery of chiral tartaric acid resolving agents |
| AT02803000T ATE428677T1 (de) | 2001-11-14 | 2002-11-08 | Rückgewinnung und recycling chiraler weinsäureverbindungen zur racematspaltung |
| CA002465294A CA2465294A1 (en) | 2001-11-14 | 2002-11-08 | Recovery and recycling of chiral tartaric acid resolving agents |
| ES02803000T ES2324772T3 (es) | 2001-11-14 | 2002-11-08 | Recuperacion y reciclaje de agentes de resolucion del acido tartarico quiral. |
| HU0402368A HUP0402368A3 (en) | 2001-11-14 | 2002-11-08 | Recovery and recycling of chiral tartaric acid resolving agents |
| JP2003543972A JP2005509011A (ja) | 2001-11-14 | 2002-11-08 | キラル酒石酸分割剤の回収および再利用 |
| PCT/EP2002/012494 WO2003042132A1 (en) | 2001-11-14 | 2002-11-08 | Recovery and recycling of chiral tartaric acid resolving agents |
| DE60232006T DE60232006D1 (de) | 2001-11-14 | 2002-11-08 | Rückgewinnung und recycling chiraler weinsäureverbindungen zur racematspaltung |
| IL16154002A IL161540A0 (en) | 2001-11-14 | 2002-11-08 | Recovery and recycling of chiral tartaric acid resolving agents |
| EP02803000A EP1446372B1 (en) | 2001-11-14 | 2002-11-08 | Recovery and recycling of chiral tartaric acid resolving agents |
| US10/495,359 US7838700B2 (en) | 2001-11-14 | 2002-11-08 | Recovery and recycling of chiral tartaric acid resolving agents |
| IL161540A IL161540A (en) | 2001-11-14 | 2004-04-21 | Process for the recovery of substituted tartaric acid resolving agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0127346A GB2382074A (en) | 2001-11-14 | 2001-11-14 | Recovery of chiral tartaric acid resolving agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB0127346D0 GB0127346D0 (en) | 2002-01-02 |
| GB2382074A true GB2382074A (en) | 2003-05-21 |
Family
ID=9925776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0127346A Withdrawn GB2382074A (en) | 2001-11-14 | 2001-11-14 | Recovery of chiral tartaric acid resolving agents |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7838700B2 (enExample) |
| EP (1) | EP1446372B1 (enExample) |
| JP (1) | JP2005509011A (enExample) |
| AT (1) | ATE428677T1 (enExample) |
| CA (1) | CA2465294A1 (enExample) |
| DE (1) | DE60232006D1 (enExample) |
| ES (1) | ES2324772T3 (enExample) |
| GB (1) | GB2382074A (enExample) |
| HU (1) | HUP0402368A3 (enExample) |
| IL (2) | IL161540A0 (enExample) |
| WO (1) | WO2003042132A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080194832A1 (en) * | 2005-05-09 | 2008-08-14 | Ragactives, S.L. | Method for the Resolution of 2-Amino-6-Propylamino-4,5,6,7-Tetrahydrobenzothiazol and Intermediate Compounds |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1315777C (zh) | 2003-01-16 | 2007-05-16 | 东丽泛应化学(股) | 旋光二酰基酒石酸的回收方法 |
| EP1736462A1 (en) * | 2005-06-22 | 2006-12-27 | Sandoz AG | Recovery of optically active tartaric acid resolving agents |
| MD4504C1 (ro) * | 2016-04-13 | 2018-03-31 | Общественное Учреждение "Научно-Практический Институт Садоводства И Пищевых Технологий" | Procedeu de obţinere a acidului tartric din tartratul de calciu obţinut din deşeuri vinicole |
| JP7516029B2 (ja) | 2018-11-16 | 2024-07-16 | アムジエン・インコーポレーテツド | Ｋｒａｓ ｇ１２ｃ阻害剤化合物の重要な中間体の改良合成法 |
| MX2023003983A (es) * | 2020-10-07 | 2023-04-24 | Amgen Inc | Procedimiento para racemizar y aislar atropisomeros de 7-cloro-6-fluoro-1-(2-isopropil-4-metilpiridin-3-il)pirido[2,3-d] pirimidin-2,4(1h,3h)-diona. |
| CN112358398A (zh) * | 2020-11-19 | 2021-02-12 | 山东新华制药股份有限公司 | D-(+)-二对甲苯甲酰酒石酸的回收制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09176115A (ja) * | 1995-12-28 | 1997-07-08 | Koei Chem Co Ltd | 光学活性なｎ−ベンジル−３−アミノピロリジンの製造方法 |
| HU221921B1 (hu) | 1996-07-08 | 2003-02-28 | Richter Gedeon Vegyészeti Gyár Rt. | N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására |
| CN1173929C (zh) * | 1999-10-19 | 2004-11-03 | 中国科学院成都有机化学研究所 | 光学纯肾上腺素类β-激动剂的组合拆分制备法 |
| GB9930577D0 (en) | 1999-12-23 | 2000-02-16 | Smithkline Beecham Plc | Novel process |
-
2001
- 2001-11-14 GB GB0127346A patent/GB2382074A/en not_active Withdrawn
-
2002
- 2002-11-08 WO PCT/EP2002/012494 patent/WO2003042132A1/en not_active Ceased
- 2002-11-08 HU HU0402368A patent/HUP0402368A3/hu unknown
- 2002-11-08 CA CA002465294A patent/CA2465294A1/en not_active Abandoned
- 2002-11-08 US US10/495,359 patent/US7838700B2/en not_active Expired - Fee Related
- 2002-11-08 DE DE60232006T patent/DE60232006D1/de not_active Expired - Lifetime
- 2002-11-08 AT AT02803000T patent/ATE428677T1/de not_active IP Right Cessation
- 2002-11-08 JP JP2003543972A patent/JP2005509011A/ja active Pending
- 2002-11-08 IL IL16154002A patent/IL161540A0/xx active IP Right Grant
- 2002-11-08 ES ES02803000T patent/ES2324772T3/es not_active Expired - Lifetime
- 2002-11-08 EP EP02803000A patent/EP1446372B1/en not_active Expired - Lifetime
-
2004
- 2004-04-21 IL IL161540A patent/IL161540A/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080194832A1 (en) * | 2005-05-09 | 2008-08-14 | Ragactives, S.L. | Method for the Resolution of 2-Amino-6-Propylamino-4,5,6,7-Tetrahydrobenzothiazol and Intermediate Compounds |
| US8952173B2 (en) * | 2005-05-09 | 2015-02-10 | Crystal Pharma, S.A.U. | Method for the resolution of 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazol and intermediate compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| IL161540A (en) | 2011-03-31 |
| IL161540A0 (en) | 2004-09-27 |
| ATE428677T1 (de) | 2009-05-15 |
| US7838700B2 (en) | 2010-11-23 |
| DE60232006D1 (de) | 2009-05-28 |
| EP1446372B1 (en) | 2009-04-15 |
| GB0127346D0 (en) | 2002-01-02 |
| EP1446372A1 (en) | 2004-08-18 |
| ES2324772T3 (es) | 2009-08-14 |
| HUP0402368A2 (hu) | 2005-03-29 |
| HUP0402368A3 (en) | 2008-02-28 |
| JP2005509011A (ja) | 2005-04-07 |
| WO2003042132A1 (en) | 2003-05-22 |
| CA2465294A1 (en) | 2003-05-22 |
| US20050085665A1 (en) | 2005-04-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4795435B2 (ja) | エソメプラゾール及びその塩の製造方法 | |
| US20040171836A1 (en) | Method for producing optical-active cis-piperidine derivatives | |
| JPH07309834A (ja) | 鏡像体的に純粋なジアリールプロリノールの製造方法 | |
| EP1446372B1 (en) | Recovery and recycling of chiral tartaric acid resolving agents | |
| WO2016174685A1 (en) | Process for the enantiomeric resolution of apremilast intermediates | |
| EP2507212B1 (en) | Process for preparing methyl phenidate hydrochloride | |
| EP2234974B1 (en) | Process for the preparation of (s)-1-alkyl-2',6'-pipecoloxylidide compound | |
| JP2009515945A (ja) | 塩酸ドネペジルの調製に有用な中間体およびその新規な多形の改善された合成および調製 | |
| KR20100096103A (ko) | 광학 활성 3-아미노피롤리딘염, 그 제조 방법 및 3-아미노피롤리딘의 광학 분할 방법 | |
| JP3312459B2 (ja) | 光学活性アミンの単離方法 | |
| EP1973896B1 (en) | A process for the preparation of the (s)-enantiomer of omeprazole | |
| US6340762B2 (en) | Method for optical resolution of piperidine carboxylic acid derivative | |
| KR100914691B1 (ko) | 도네페질 또는 그의 제조용 중간체의 제조방법 | |
| JP3084577B2 (ja) | 光学活性なアトロラクチン酸の製造方法および製造の中間体 | |
| US8455692B2 (en) | Process for resolution of 1-(3-hydroxyphenyl)-2-methylamino ethanol | |
| EP3447044A1 (en) | Method for preparing d-4,4'-biphenylalanine alkyl ester or l-4,4'-biphenylalanine alkyl ester from dl-4,4'-biphenylalanine alkyl ester | |
| EP2234975B1 (en) | Process for producing pipecolic-2-acid-2 ',6'-xylidide useful as an intermediate for the preparation of local anesthetics | |
| JP3911302B2 (ja) | 光学活性２−メチルピペラジンの製造法 | |
| JP2002371060A (ja) | 光学活性アミノピペリジン誘導体の製造方法 | |
| JP5613509B2 (ja) | フェキソフェナジン一塩酸塩の取得方法 | |
| JP2000178253A (ja) | 光学活性ピペコリン酸の製造法 | |
| WO2023156675A1 (en) | Process for purification of linagliptin | |
| JPH09286763A (ja) | １−アルキル−２−（置換フェニル）エチルアミン類の光学活性体の製造方法 | |
| RU2173679C2 (ru) | Способ получения флуоксетина | |
| EP1736462A1 (en) | Recovery of optically active tartaric acid resolving agents |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |