SK19002001A3 - Spôsob delenia diastereomérnych báz 2-[(dimetylamino)metyl]-1- (3-metoxyfenyl)-cyklohexanolu) - Google Patents
Spôsob delenia diastereomérnych báz 2-[(dimetylamino)metyl]-1- (3-metoxyfenyl)-cyklohexanolu) Download PDFInfo
- Publication number
- SK19002001A3 SK19002001A3 SK1900-2001A SK19002001A SK19002001A3 SK 19002001 A3 SK19002001 A3 SK 19002001A3 SK 19002001 A SK19002001 A SK 19002001A SK 19002001 A3 SK19002001 A3 SK 19002001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- cis
- mixture
- water
- trans
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- TVYLLZQTGLZFBW-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol Chemical compound COC1=CC=CC(C2(O)C(CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 239000013078 crystal Substances 0.000 claims description 21
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 239000003791 organic solvent mixture Substances 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 235000019441 ethanol Nutrition 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- PPKXEPBICJTCRU-XMZRARIVSA-N (R,R)-tramadol hydrochloride Chemical compound Cl.COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 PPKXEPBICJTCRU-XMZRARIVSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229960003107 tramadol hydrochloride Drugs 0.000 description 3
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- TVYLLZQTGLZFBW-HOCLYGCPSA-N (1r,2s)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC([C@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-HOCLYGCPSA-N 0.000 description 1
- TVYLLZQTGLZFBW-GDBMZVCRSA-N (1s,2r)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol Chemical compound COC1=CC=CC([C@@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GDBMZVCRSA-N 0.000 description 1
- TVYLLZQTGLZFBW-GOEBONIOSA-N (S,S)-tramadol Chemical compound COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical group 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP1999/004325 WO2000078705A1 (fr) | 1999-06-22 | 1999-06-22 | Procede de separation des bases diastereo-isomeres de 2-[(dimethylamino)methyl]-1-(3-methoxy-phenyl)-cyclohexanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK19002001A3 true SK19002001A3 (sk) | 2002-05-09 |
Family
ID=8167340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1900-2001A SK19002001A3 (sk) | 1999-06-22 | 1999-06-22 | Spôsob delenia diastereomérnych báz 2-[(dimetylamino)metyl]-1- (3-metoxyfenyl)-cyklohexanolu) |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6521792B2 (fr) |
| EP (1) | EP1187804A1 (fr) |
| JP (1) | JP2003502400A (fr) |
| AU (1) | AU4775699A (fr) |
| CA (1) | CA2375234A1 (fr) |
| CZ (1) | CZ20014669A3 (fr) |
| HK (1) | HK1045301A1 (fr) |
| HU (1) | HUP0201464A3 (fr) |
| MX (1) | MXPA01013145A (fr) |
| SK (1) | SK19002001A3 (fr) |
| WO (1) | WO2000078705A1 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6579805B1 (en) * | 1999-01-05 | 2003-06-17 | Ronal Systems Corp. | In situ chemical generator and method |
| DE10108308A1 (de) * | 2001-02-21 | 2002-08-29 | Gruenenthal Gmbh | Verfahren zur Isolierung und Reinigung von (1RS,2RS)-2[(Dimethylamino)methyl]-1-(3-methoxyphenyl)-cyclohexanol |
| EP1346978A1 (fr) * | 2002-03-21 | 2003-09-24 | Jubilant Organosys Limited | Procédé pour la préparation de tramadol chlorohydrate et/ou de tramadol monohydrate |
| US7375035B2 (en) * | 2003-04-29 | 2008-05-20 | Ronal Systems Corporation | Host and ancillary tool interface methodology for distributed processing |
| US7429714B2 (en) | 2003-06-20 | 2008-09-30 | Ronal Systems Corporation | Modular ICP torch assembly |
| EP1785412A1 (fr) * | 2005-11-14 | 2007-05-16 | IPCA Laboratories Limited | Procédé de récuperation de Tramadol |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3830934A (en) * | 1967-07-27 | 1974-08-20 | Gruenenthal Chemie | Analgesic and antitussive compositions and methods |
| IL103096A (en) * | 1992-09-08 | 1996-12-05 | Chemagis Ltd | Process for purification 2 -]) Dimethylamino (methyl-1-) 3-methoxycinyl (cyclohexanol and its salts. |
| IL116281A (en) * | 1995-12-07 | 1999-06-20 | Chemagis Ltd | Process for the purification of (rr,ss)-2-dimethylaminomethyl-1-(3-methoxyphenyl) cyclohexanol and its salts |
| IL119121A (en) * | 1996-08-22 | 2000-11-21 | Chemagis Ltd | Process for the purification of (RR-SS)-2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexanol hydrochloride |
| IE980512A1 (en) * | 1997-07-15 | 1999-10-20 | Russinsky Ltd | A product and process |
| US5877351A (en) * | 1997-12-24 | 1999-03-02 | Wyckoff Chemical Company, Inc. | Preparation and purification process for 2- (dimethylamino) methyl!-1-(3-methoxphenyl)-cyclohexanol and its salts |
| GB9800657D0 (en) * | 1998-01-14 | 1998-03-11 | Macfarlan Smith Ltd | Improved purification process |
-
1999
- 1999-06-22 SK SK1900-2001A patent/SK19002001A3/sk unknown
- 1999-06-22 JP JP2001504875A patent/JP2003502400A/ja not_active Withdrawn
- 1999-06-22 AU AU47756/99A patent/AU4775699A/en not_active Abandoned
- 1999-06-22 CA CA002375234A patent/CA2375234A1/fr not_active Abandoned
- 1999-06-22 WO PCT/EP1999/004325 patent/WO2000078705A1/fr not_active Application Discontinuation
- 1999-06-22 EP EP99931139A patent/EP1187804A1/fr not_active Ceased
- 1999-06-22 MX MXPA01013145A patent/MXPA01013145A/es unknown
- 1999-06-22 HU HU0201464A patent/HUP0201464A3/hu unknown
- 1999-06-22 CZ CZ20014669A patent/CZ20014669A3/cs unknown
-
2001
- 2001-12-21 US US10/024,590 patent/US6521792B2/en not_active Expired - Fee Related
-
2002
- 2002-09-13 HK HK02106754.1A patent/HK1045301A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0201464A3 (en) | 2003-02-28 |
| JP2003502400A (ja) | 2003-01-21 |
| CZ20014669A3 (cs) | 2002-05-15 |
| US20020091287A1 (en) | 2002-07-11 |
| EP1187804A1 (fr) | 2002-03-20 |
| HUP0201464A2 (hu) | 2002-12-28 |
| CA2375234A1 (fr) | 2000-12-28 |
| HK1045301A1 (zh) | 2002-11-22 |
| US6521792B2 (en) | 2003-02-18 |
| WO2000078705A1 (fr) | 2000-12-28 |
| AU4775699A (en) | 2001-01-09 |
| MXPA01013145A (es) | 2002-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK287696B6 (sk) | Spôsob prípravy voľnej bázy racemického citalopramu a voľnej bázy S- alebo R-citalopramu | |
| CZ281203B6 (cs) | Způsob racemizace opticky aktivních amidů aminokyselin | |
| ES2214047T3 (es) | Procedimiento para la disociacion de racematos de acidos 2-hidroxipropionicos. | |
| US20030092773A1 (en) | Process for the separation of the cis trans diasteroisomers of tramadol | |
| SK19002001A3 (sk) | Spôsob delenia diastereomérnych báz 2-[(dimetylamino)metyl]-1- (3-metoxyfenyl)-cyklohexanolu) | |
| US5457224A (en) | Resolution of racemic verapamil | |
| JP5406194B2 (ja) | Ｒ−ゴシポールｌ−フェニルアラニノールジエナミンを調製するための方法 | |
| JP2004511476A (ja) | Ｒ（＋）α−リポ酸の製造方法 | |
| WO2007080470A2 (fr) | Procede de purification de levetiracetame | |
| EP0253571B1 (fr) | Procédé de dédoublement et de racémisation d'amines à l'aide d'alpha-hydrogènes acides | |
| EP0174358A1 (fr) | Nouveaux sels diastereomeres de phenylalanine et ses derives n-acyliques et procede de separation de phenylalanine optiquement actives et de ses derives n-acyliques | |
| US20050070522A1 (en) | Resolution of a narwedine amide derivative | |
| JPH04211079A (ja) | ｃｉｓ−３−アミノ−４−［２−（２−フリル）エタン−１−イル］−１−メトキシカルボニルメチル−アゼチジン−２−オンの分割方法 | |
| EP1484315A1 (fr) | Procede de production de beta-phenylalamine optiquement active | |
| KR20010006117A (ko) | 단일 에난티오머 나웨딘을 제조하기 위한 방법 | |
| FI96681C (fi) | Menetelmä 2,2-dimetyylisyklopropaanikarboksyylihapon rasemaattipilkkomiseksi | |
| HU205594B (en) | Process for producing optical isomeres of cyclopropane-carboxylic acids5 | |
| NZ516627A (en) | Process for the separation of the diastereomeric bases of 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-cyclohexanol | |
| US20060167280A1 (en) | Method for purifying simvastatin | |
| CA1338867C (fr) | Derives et precurseurs du captopril et de ses analogues; methodes de preparation du captopril et de ses analogues | |
| JP4067319B2 (ja) | 光学分割法及び光学活性化合物の製造法 | |
| SK43594A3 (en) | Method of production of tramadol hydrogenchloride | |
| IL91444A (en) | Wealthy materials with their own crystallization ability are part of the S-protected threading | |
| EP0434743A4 (en) | Methods for preparing captopril and its analogues | |
| WO2006013581A2 (fr) | Resolution d'acides organiques racemiques avec (1s, 4s)-4[3,4-dichlorophenyl]-1,2,3,4- tetrahydro-n-methyl-1-naphtaloneamine |