HRP20120306T1 - Postupak razdvajanja zopiklona i njegovih međuprodukata - Google Patents
Postupak razdvajanja zopiklona i njegovih međuprodukata Download PDFInfo
- Publication number
- HRP20120306T1 HRP20120306T1 HR20120306T HRP20120306T HRP20120306T1 HR P20120306 T1 HRP20120306 T1 HR P20120306T1 HR 20120306 T HR20120306 T HR 20120306T HR P20120306 T HRP20120306 T HR P20120306T HR P20120306 T1 HRP20120306 T1 HR P20120306T1
- Authority
- HR
- Croatia
- Prior art keywords
- acetyl
- zopiclone
- formula
- methionate
- aspartate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 17
- 150000001875 compounds Chemical class 0.000 title claims abstract 7
- GBBSUAFBMRNDJC-MRXNPFEDSA-N (5R)-zopiclone Chemical class C1CN(C)CCN1C(=O)O[C@@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-MRXNPFEDSA-N 0.000 title 1
- 229960000820 zopiclone Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 14
- 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 claims abstract 6
- 150000001413 amino acids Chemical class 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract 2
- 229940009098 aspartate Drugs 0.000 claims 5
- 229940024606 amino acid Drugs 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000000926 separation method Methods 0.000 claims 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- GBBSUAFBMRNDJC-INIZCTEOSA-N eszopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-INIZCTEOSA-N 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- RFMMMVDNIPUKGG-RXMQYKEDSA-N (2r)-2-acetamidopentanedioic acid Chemical compound CC(=O)N[C@@H](C(O)=O)CCC(O)=O RFMMMVDNIPUKGG-RXMQYKEDSA-N 0.000 claims 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims 1
- XUYPXLNMDZIRQH-ZCFIWIBFSA-N N-acetyl-D-methionine Chemical compound CSCC[C@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-ZCFIWIBFSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- WHZRCUIISKRTJL-UHFFFAOYSA-N [2-(6-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl)-2-oxoethyl] hexanoate Chemical compound C1C(F)C2=CC(=O)C=CC2(C)C2C1C1CC(C)C(C(=O)COC(=O)CCCCC)C1(C)CC2O WHZRCUIISKRTJL-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000012452 mother liquor Substances 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 230000006340 racemization Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract 1
Classifications
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Postupak razdvajanja racemata spoja formule (I) u jedan od njegovih enantiomera: naznačen time što se sastoji u izdvajanju navedenog jednog od njegovih enantiomera iz dijastereoizomerne soli formule (II): gdje je HX optički aktivna acetilirana aminokiselina formule (III): gdje: n je 0, 1, 2 ili 3, R1 je H, alkilna skupina, arilna skupina, heteroarilna skupina, CONH2, COOH, SR2 ili OR2, gdje je R2 C1-C6 alkil. Patent sadrži još 15 patentnih zahtjeva.
Claims (16)
1. Postupak razdvajanja racemata spoja formule (I) u jedan od njegovih enantiomera:
[image]
naznačen time što se sastoji u izdvajanju navedenog jednog od njegovih enantiomera iz dijastereoizomerne soli formule (II):
[image]
gdje je HX optički aktivna acetilirana aminokiselina formule (III):
[image]
gdje:
n je 0, 1, 2 ili 3,
R1 je H, alkilna skupina, arilna skupina, heteroarilna skupina, CONH2, COOH, SR2 ili OR2, gdje je R2 C1-C6 alkil.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se optički aktivnu acetiliranu aminokiselinu formule (III) bira između N-acetil-d-glutaminske kiseline, N-acetil-1-glutaminske kiseline, N-acetil-d-asparaginske kiseline, N-acetil-1-asparaginske kiseline, N-acetil-d-metionina i N-acetil-1-metionina.
3. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je enantiomer formule (I) (S)-enantiomer.
4. Postupak u skladu s patentnim zahtjevom 3, naznačen time što je dijastereoizomerna sol formule (II) (S)-zopiklon-N-acetil-d-glutamat, (S)-zopiklon-N-acetil-d-aspartat, (S)-zopiklon-N-acetil-d-metionat, (S)-zopiklon-N-acetil-1-glutamat, (S)-zopiklon-N-acetil-1-aspartat ili (S)-zopiklon-N-acetil-1-metionat.
5. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je enantiomer formule (I) (R)-enantiomer.
6. Postupak u skladu s patentnim zahtjevom 5, naznačen time što je dijastereoizomerna sol formule (II) (R)-zopiklon-N-acetil-1-glutamat, (R)-zopiklon-N-acetil-1-aspartat ili (R)-zopiklon-N-acetil-1-metionat, (R)-zopiklon-N-acetil-d-glutamat, (R)-zopiklon-N-acetil-d-aspartat ili (R)-zopiklon-N-acetil-d-metionat.
7. Postupak razdvajanja racemata spoja formule (I) u jedan od njegovih enantiomera:
[image]
naznačen time što se sastoji u sljedećim koracima:
reakcije navedenog racemata s bilo kojim od enantiomera optički aktivne acetilirane aminokiseline formule (III):
[image]
gdje su n i R1 definirani kao gore;
izdvajanja optički čiste dijastereoizomerne soli formule (II):
[image]
gdje je HX optički aktivna acetilirana aminokiselina formule (III); te
izdvajanja enantiomera formule (I) iz njegove dijastereoizomerne soli formule (II).
8. Postupak u skladu s patentnim zahtjevom 7, naznačen time što se organsko otapalo bira između alkohola, etera, estera, ketona, nitrila, halogeniranih otapala, aromatskih otapala i njihovih smjesa.
9. Postupak u skladu s patentni zahtjevi 7 ili 8, naznačen time što se organsko otapalo bira između metanola, toluena, ksilena, acetona, etil-acetata, acetonitrila, tetrahidrofurana, izopropil-acetata, etil-formijata, metil-tert-butil-etera, dietil-karbonata, klorbenzena, diklormetana i njihovih smjesa.
10. Postupak u skladu s bilo kojim od patentnih zahtjeva 7 do 9, naznačen time što se optički čistu dijastereoizomernu sol formule (II), izdvojenu u koraku b), bira iz skupine koju čine (S)-zopiklon-N-acetil-d-glutamat, (R)-zopiklon-N-acetil-1-glutamat, (S)-zopiklon-N-acetil-d-aspartat, (R)-zopiklon-N-acetil-1-aspartat, (S)-zopiklon-N-acetil-d-metionat, te (R)-zopiklon-N-acetil-1-metionat.
11. Postupak u skladu s bilo kojim od patentnih zahtjeva 7 do 10, naznačen time što se sastoji u dodatnom koraku izdvajanja druge optički čiste dijastereoizomerne soli formule (II).
12. Postupak u skladu s patentnim zahtjevom 11, naznačen time što se dodatno izdvajanje druge dijastereoizomerne soli formule (II) sastoji u koncentriranju matičnog luga dobivenog prilikom izdvajanja prve dijastereoizomerne soli i kristalizacije nakon toga kako bi se dobilo navedenu drugu dijastereoizomernu sol.
13. Postupak u skladu s patentnim zahtjevom 12, naznačen time što je druga dijastereoizomerna sol (S)-zopiklon-N-acetil-1-glutamat, (S)-zopiklon-N-acetil-1-aspartat, (S)-zopiklon-N-acetil-1-metionat, (R)-zopiklon-N-acetil-d-glutamat, (R)-zopiklon-N-acetil-d-aspartat ili (R)-zopiklon-N-acetil-d-metionat.
14. Postupak u skladu s patentnim zahtjevom 1 ili 5, naznačen time što se dodatno sastoji u racemizaciji (R)-enantiomera spoja formule (I) kako bi se dobilo racemat spoja formule (I), a zatim i izdvajanje (S)-enantiomera spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 6-13.
15. Optički čista dijastereoizomerna sol formule (II):
[image]
naznačena time što je HX definiran kao ranije u ovom dokumentu.
16. Sol u skladu s patentnim zahtjevom 15, naznačena time što je se bira iz skupine koju čine (S)-zopiklon-N-acetil-d-glutamat, (S)-zopiklon-N-acetil-d-aspartat, (S)-zopiklon-N-acetil-d-metionat, (S)-zopiklon-N-acetil-1-glutamat, (S)-zopiklon-N-acetil-1-aspartat i (S)-zopiklon-N-acetil-1-metionat.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07380226A EP2020403A1 (en) | 2007-08-02 | 2007-08-02 | Process for the resolution of zopiclone and intermediate compounds |
| PCT/EP2008/060115 WO2009016251A1 (en) | 2007-08-02 | 2008-08-01 | Process for the resolution of zopiclone and intermediate compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120306T1 true HRP20120306T1 (hr) | 2012-04-30 |
Family
ID=38871700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20120306T HRP20120306T1 (hr) | 2007-08-02 | 2012-04-10 | Postupak razdvajanja zopiklona i njegovih međuprodukata |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7772396B2 (hr) |
| EP (2) | EP2020403A1 (hr) |
| JP (1) | JP2010535177A (hr) |
| KR (1) | KR20100044241A (hr) |
| CN (1) | CN101772475B (hr) |
| AT (1) | ATE551312T1 (hr) |
| AU (1) | AU2008281717A1 (hr) |
| CA (1) | CA2695254A1 (hr) |
| ES (1) | ES2385120T3 (hr) |
| HR (1) | HRP20120306T1 (hr) |
| IL (1) | IL203557A (hr) |
| MX (1) | MX2010001229A (hr) |
| NZ (1) | NZ583097A (hr) |
| PL (1) | PL2183201T3 (hr) |
| RU (1) | RU2010107453A (hr) |
| SI (1) | SI2183201T1 (hr) |
| WO (1) | WO2009016251A1 (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7476737B2 (en) * | 2005-09-05 | 2009-01-13 | Dr. Reddy's Laboratories Limited | Eszopiclone process |
| US8163913B2 (en) * | 2005-12-19 | 2012-04-24 | Sicor Inc. | Forms of tiotropium bromide and processes for preparation thereof |
| CN101607961B (zh) * | 2008-06-18 | 2011-08-10 | 天津天士力集团有限公司 | 一种右佐匹克隆结晶及其组合物 |
| EP2345654A1 (en) * | 2010-01-05 | 2011-07-20 | LEK Pharmaceuticals d.d. | Eszopiclone particles and a process for their preparation |
| CN103193779B (zh) * | 2012-01-05 | 2016-04-20 | 成都弘达药业有限公司 | 一种右佐匹克隆的制备方法 |
| CN105960394B (zh) * | 2014-02-06 | 2019-03-15 | 宇部兴产株式会社 | 二氢吲哚化合物的制造方法 |
| DE102020205560B4 (de) | 2020-04-30 | 2022-05-25 | Zettl Interieur Gmbh | Flexible atemschutzmaske und deren verwendung |
| CN113214267B (zh) * | 2021-05-08 | 2022-06-28 | 上海中西三维药业有限公司 | 一种制备纯净且光学富集的右佐匹克隆精制方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA04285A (fr) | 1972-01-07 | 1979-12-31 | Rhone Poulenc Sa | Nouveaux dérivés de la pyrrolo (3,4-b) pyrazine et leur préparation. |
| FR2671800B1 (fr) | 1991-01-17 | 1993-03-12 | Rhone Poulenc Rorer Sa | Derive de la 5h-pyrrolo[3,4-b]pyrazine optiquement actif, sa preparation et les compositions pharmaceutiques qui le contiennent. |
| ES2203319B1 (es) | 2002-04-03 | 2005-03-01 | Universidad De Oviedo | Nuevos carbonatos opticamente activos como intermedios en la sintesis de (+)-zopiclona. |
| AU2004305563C1 (en) | 2003-12-11 | 2011-07-07 | Sunovion Pharmaceuticals Inc. | Combination of a sedative and a neurotransmitter modulator, and methods for improving sleep quality and treating depression |
| DK1742624T3 (da) | 2004-02-18 | 2010-03-08 | Sepracor Inc | Dopamin-agonist-kombinationsterapi med sedativer til forbedring af søvnkvalitet |
| JP4970244B2 (ja) | 2004-04-05 | 2012-07-04 | サノビオン ファーマシューティカルズ インク | エスゾピクロンを用いる治療方法 |
| EP1919912A1 (en) | 2005-06-21 | 2008-05-14 | Merck Generics (UK) Limited | Process for enantiomeric separation of zopiclone |
| US7476737B2 (en) | 2005-09-05 | 2009-01-13 | Dr. Reddy's Laboratories Limited | Eszopiclone process |
| EP1984368A2 (en) | 2006-01-17 | 2008-10-29 | Glenmark Pharmaceuticals Limited | Improved process for the preparation of an optically active 5h-pyrrolo [3,4-b]pyrazine derivative |
| WO2007088073A1 (en) | 2006-02-03 | 2007-08-09 | Synthon B.V. | Zopiclone resolution using l-tartaric acid |
| WO2007109799A2 (en) | 2006-03-23 | 2007-09-27 | Teva Pharmaceutical Industries Ltd. | Polymorphs of eszopiclone malate |
| EP2007768A2 (en) | 2006-04-20 | 2008-12-31 | Teva Pharmaceutical Industries Ltd | Methods for preparing eszopiclone crystalline form a, substantially pure eszopiclone and optically enriched eszopiclone |
-
2007
- 2007-08-02 EP EP07380226A patent/EP2020403A1/en not_active Withdrawn
- 2007-10-03 US US11/866,584 patent/US7772396B2/en not_active Expired - Fee Related
-
2008
- 2008-08-01 MX MX2010001229A patent/MX2010001229A/es active IP Right Grant
- 2008-08-01 AU AU2008281717A patent/AU2008281717A1/en not_active Abandoned
- 2008-08-01 PL PL08786735T patent/PL2183201T3/pl unknown
- 2008-08-01 JP JP2010518689A patent/JP2010535177A/ja not_active Withdrawn
- 2008-08-01 KR KR1020107004730A patent/KR20100044241A/ko not_active Application Discontinuation
- 2008-08-01 EP EP08786735A patent/EP2183201B1/en active Active
- 2008-08-01 AT AT08786735T patent/ATE551312T1/de active
- 2008-08-01 ES ES08786735T patent/ES2385120T3/es active Active
- 2008-08-01 CN CN200880101463XA patent/CN101772475B/zh not_active Expired - Fee Related
- 2008-08-01 RU RU2010107453/04A patent/RU2010107453A/ru not_active Application Discontinuation
- 2008-08-01 SI SI200830601T patent/SI2183201T1/sl unknown
- 2008-08-01 CA CA2695254A patent/CA2695254A1/en not_active Abandoned
- 2008-08-01 WO PCT/EP2008/060115 patent/WO2009016251A1/en active Application Filing
- 2008-08-01 NZ NZ583097A patent/NZ583097A/en not_active IP Right Cessation
-
2010
- 2010-01-27 IL IL203557A patent/IL203557A/en not_active IP Right Cessation
- 2010-07-02 US US12/830,147 patent/US7968712B2/en not_active Expired - Fee Related
-
2012
- 2012-04-10 HR HR20120306T patent/HRP20120306T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2183201B1 (en) | 2012-03-28 |
| SI2183201T1 (sl) | 2012-05-31 |
| CN101772475A (zh) | 2010-07-07 |
| ES2385120T3 (es) | 2012-07-18 |
| EP2020403A1 (en) | 2009-02-04 |
| US7968712B2 (en) | 2011-06-28 |
| AU2008281717A1 (en) | 2009-02-05 |
| JP2010535177A (ja) | 2010-11-18 |
| KR20100044241A (ko) | 2010-04-29 |
| NZ583097A (en) | 2011-03-31 |
| IL203557A (en) | 2014-11-30 |
| ATE551312T1 (de) | 2012-04-15 |
| RU2010107453A (ru) | 2011-09-10 |
| PL2183201T3 (pl) | 2012-09-28 |
| CN101772475B (zh) | 2013-11-06 |
| US7772396B2 (en) | 2010-08-10 |
| EP2183201A1 (en) | 2010-05-12 |
| WO2009016251A1 (en) | 2009-02-05 |
| MX2010001229A (es) | 2010-03-04 |
| CA2695254A1 (en) | 2009-02-05 |
| US20090036681A1 (en) | 2009-02-05 |
| US20100274018A1 (en) | 2010-10-28 |
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