DE69716713D1 - Verfahren zur herstellung von d-threo-(r,r)-methylphenidat und recycling nicht erwünschter enantiomere durch epimerisierung - Google Patents
Verfahren zur herstellung von d-threo-(r,r)-methylphenidat und recycling nicht erwünschter enantiomere durch epimerisierungInfo
- Publication number
- DE69716713D1 DE69716713D1 DE69716713T DE69716713T DE69716713D1 DE 69716713 D1 DE69716713 D1 DE 69716713D1 DE 69716713 T DE69716713 T DE 69716713T DE 69716713 T DE69716713 T DE 69716713T DE 69716713 D1 DE69716713 D1 DE 69716713D1
- Authority
- DE
- Germany
- Prior art keywords
- threo
- methylphenidate
- epimerization
- producing
- enantiomers
- 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.)
- Expired - Fee Related
Links
- 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 compound C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title abstract 3
- 238000006345 epimerization reaction Methods 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 229960001344 methylphenidate Drugs 0.000 title 1
- 238000004064 recycling Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 3
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- DUGOZIWVEXMGBE-OLZOCXBDSA-N methyl (S)-phenyl[(R)-piperidin-2-yl]acetate Chemical compound C([C@@H]1[C@@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 DUGOZIWVEXMGBE-OLZOCXBDSA-N 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4458—Non condensed piperidines, e.g. piperocaine only substituted in position 2, e.g. methylphenidate
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
- B01D9/0013—Crystallisation cooling by heat exchange by indirect heat exchange
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9602174.6A GB9602174D0 (en) | 1996-02-02 | 1996-02-02 | Resolution/racemization process |
| GBGB9618836.2A GB9618836D0 (en) | 1996-09-10 | 1996-09-10 | Resolution/racemisation process |
| PCT/GB1997/000281 WO1997028124A1 (en) | 1996-02-02 | 1997-01-31 | Process for the preparation of d-threo-(r,r)-methyl phenidate and recycling of undesired enantiomers by epimerisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69716713D1 true DE69716713D1 (de) | 2002-12-05 |
| DE69716713T2 DE69716713T2 (de) | 2003-07-03 |
Family
ID=26308593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69716713T Expired - Fee Related DE69716713T2 (de) | 1996-02-02 | 1997-01-31 | Verfahren zur herstellung von d-threo-(r,r)-methylphenidat und recycling nicht erwünschter enantiomere durch epimerisierung |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7164025B2 (de) |
| EP (1) | EP0879228B1 (de) |
| JP (1) | JP2000504008A (de) |
| KR (1) | KR100453707B1 (de) |
| AT (1) | ATE226940T1 (de) |
| AU (1) | AU715183B2 (de) |
| CA (1) | CA2243534C (de) |
| CZ (1) | CZ292609B6 (de) |
| DE (1) | DE69716713T2 (de) |
| DK (1) | DK0879228T3 (de) |
| ES (1) | ES2187753T3 (de) |
| HU (1) | HUP9901658A3 (de) |
| MX (1) | MX209701B (de) |
| PT (1) | PT879228E (de) |
| SK (1) | SK283553B6 (de) |
| WO (1) | WO1997028124A1 (de) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5837284A (en) | 1995-12-04 | 1998-11-17 | Mehta; Atul M. | Delivery of multiple doses of medications |
| US6486177B2 (en) * | 1995-12-04 | 2002-11-26 | Celgene Corporation | Methods for treatment of cognitive and menopausal disorders with D-threo methylphenidate |
| US5922736A (en) * | 1995-12-04 | 1999-07-13 | Celegene Corporation | Chronic, bolus administration of D-threo methylphenidate |
| GB9700912D0 (en) * | 1997-01-17 | 1997-03-05 | Chiroscience Ltd | Resolution |
| US6962997B1 (en) | 1997-05-22 | 2005-11-08 | Celgene Corporation | Process and intermediates for resolving piperidyl acetamide steroisomers |
| US6100401A (en) * | 1998-04-20 | 2000-08-08 | Novartris Ag | Process for preparing the d-threo isomer of methylphenidate hydrochloride |
| US6025502A (en) * | 1999-03-19 | 2000-02-15 | The Trustees Of The University Of Pennsylvania | Enantopselective synthesis of methyl phenidate |
| US20050239830A1 (en) * | 2004-04-26 | 2005-10-27 | Vikram Khetani | Methods of diminishing co-abuse potential |
| AU2005313887B2 (en) * | 2004-12-09 | 2011-10-27 | Celgene Corporation | Treatment using D-threo methylphenidate |
| US7897777B2 (en) * | 2007-01-05 | 2011-03-01 | Archimica, Inc. | Process of enantiomeric resolution of D,L-(±)-threo-methylphenidate |
| US20130310422A1 (en) | 2010-09-01 | 2013-11-21 | The General Hospital Corporation | Reversal of general anesthesia by administration of methylphenidate, amphetamine, modafinil, amantadine, and/or caffeine |
| US9119809B2 (en) | 2011-03-23 | 2015-09-01 | Ironshore Pharmaceuticals & Development, Inc. | Compositions for treatment of attention deficit hyperactivity disorder |
| US10905652B2 (en) | 2011-03-23 | 2021-02-02 | Ironshore Pharmaceuticals & Development, Inc. | Compositions for treatment of attention deficit hyperactivity disorder |
| US9498447B2 (en) | 2011-03-23 | 2016-11-22 | Ironshore Pharmaceuticals & Development, Inc. | Compositions for treatment of attention deficit hyperactivity disorder |
| US8916588B2 (en) | 2011-03-23 | 2014-12-23 | Ironshore Pharmaceuticals & Development, Inc. | Methods for treatment of attention deficit hyperactivity disorder |
| US10292937B2 (en) | 2011-03-23 | 2019-05-21 | Ironshore Pharmaceuticals & Development, Inc. | Methods of treatment of attention deficit hyperactivity disorder |
| US8927010B2 (en) | 2011-03-23 | 2015-01-06 | Ironshore Pharmaceuticals & Development, Inc. | Compositions for treatment of attention deficit hyperactivity disorder |
| US9283214B2 (en) | 2011-03-23 | 2016-03-15 | Ironshore Pharmaceuticals & Development, Inc. | Compositions for treatment of attention deficit hyperactivity disorder |
| US9603809B2 (en) | 2011-03-23 | 2017-03-28 | Ironshore Pharmaceuticals & Development, Inc. | Methods of treatment of attention deficit hyperactivity disorder |
| US11241391B2 (en) | 2011-03-23 | 2022-02-08 | Ironshore Pharmaceuticals & Development, Inc. | Compositions for treatment of attention deficit hyperactivity disorder |
| DK4011364T3 (da) | 2011-03-23 | 2024-03-18 | Ironshore Pharmaceuticals & Dev Inc | Fremgangsmåder og sammensætninger til behandling af ADD (Attention Deficit Disorder) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2957880A (en) * | 1953-12-23 | 1960-10-25 | Ciba Pharm Prod Inc | Process for the conversion of stereoisomers |
| SU466229A1 (ru) * | 1973-01-23 | 1975-04-05 | Всесоюзный научно-исследовательский химико-фармацевтический институт им. С.Орджоникидзе | Способ получени гидрохлорида метилового эфира трео- -фенил- (пиперидил-2)-уксусной кислоты |
| US4254261A (en) * | 1979-10-15 | 1981-03-03 | Merck & Co., Inc. | Dehydroabietylammonium salts of 6-oxo-2-piperidinecarboxylic acid |
| US5733756A (en) * | 1996-01-05 | 1998-03-31 | Celgene Corporation | Lactams and processes for stereoselective enrichment of lactams, amides, and esters |
| US6242464B1 (en) * | 1996-01-22 | 2001-06-05 | Chiroscience Limited | Single isomer methylphenidate and resolution process |
| MX9805870A (de) * | 1996-01-22 | 1999-01-31 | ||
| GB9604943D0 (en) * | 1996-03-08 | 1996-05-08 | Chiroscience Ltd | Resolution |
-
1997
- 1997-01-31 CA CA002243534A patent/CA2243534C/en not_active Expired - Fee Related
- 1997-01-31 HU HU9901658A patent/HUP9901658A3/hu unknown
- 1997-01-31 DE DE69716713T patent/DE69716713T2/de not_active Expired - Fee Related
- 1997-01-31 DK DK97902435T patent/DK0879228T3/da active
- 1997-01-31 KR KR19980705911A patent/KR100453707B1/ko not_active IP Right Cessation
- 1997-01-31 EP EP97902435A patent/EP0879228B1/de not_active Expired - Lifetime
- 1997-01-31 ES ES97902435T patent/ES2187753T3/es not_active Expired - Lifetime
- 1997-01-31 PT PT97902435T patent/PT879228E/pt unknown
- 1997-01-31 SK SK979-98A patent/SK283553B6/sk unknown
- 1997-01-31 CZ CZ19982275A patent/CZ292609B6/cs not_active IP Right Cessation
- 1997-01-31 AT AT97902435T patent/ATE226940T1/de not_active IP Right Cessation
- 1997-01-31 JP JP9527425A patent/JP2000504008A/ja not_active Ceased
- 1997-01-31 WO PCT/GB1997/000281 patent/WO1997028124A1/en active IP Right Grant
- 1997-01-31 AU AU16082/97A patent/AU715183B2/en not_active Ceased
-
1998
- 1998-07-31 MX MX9806209A patent/MX209701B/es not_active IP Right Cessation
-
2001
- 2001-08-10 US US09/928,139 patent/US7164025B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| MX209701B (es) | 2002-08-15 |
| US20020032335A1 (en) | 2002-03-14 |
| CA2243534A1 (en) | 1997-08-07 |
| HUP9901658A3 (en) | 1999-12-28 |
| MX9806209A (es) | 1998-10-31 |
| AU1608297A (en) | 1997-08-22 |
| SK283553B6 (sk) | 2003-09-11 |
| CA2243534C (en) | 2003-08-26 |
| AU715183B2 (en) | 2000-01-20 |
| DK0879228T3 (da) | 2003-03-03 |
| SK97998A3 (en) | 1999-01-11 |
| EP0879228B1 (de) | 2002-10-30 |
| WO1997028124A1 (en) | 1997-08-07 |
| KR19990082186A (ko) | 1999-11-25 |
| DE69716713T2 (de) | 2003-07-03 |
| CZ227598A3 (cs) | 1998-12-16 |
| PT879228E (pt) | 2003-01-31 |
| KR100453707B1 (ko) | 2005-01-25 |
| EP0879228A1 (de) | 1998-11-25 |
| HUP9901658A2 (hu) | 1999-09-28 |
| ES2187753T3 (es) | 2003-06-16 |
| US7164025B2 (en) | 2007-01-16 |
| CZ292609B6 (cs) | 2003-11-12 |
| ATE226940T1 (de) | 2002-11-15 |
| JP2000504008A (ja) | 2000-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |