ES2320012T3 - Procedimientos y productos intermediarios para la preparacion de estereo-isomeros de piperidina 2-sustituida. - Google Patents
Procedimientos y productos intermediarios para la preparacion de estereo-isomeros de piperidina 2-sustituida. Download PDFInfo
- Publication number
- ES2320012T3 ES2320012T3 ES05077084T ES05077084T ES2320012T3 ES 2320012 T3 ES2320012 T3 ES 2320012T3 ES 05077084 T ES05077084 T ES 05077084T ES 05077084 T ES05077084 T ES 05077084T ES 2320012 T3 ES2320012 T3 ES 2320012T3
- Authority
- ES
- Spain
- Prior art keywords
- erythro
- threo
- piperidine
- carbon atoms
- stereoisomers
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 32
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound 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 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 11
- -1 alkali metal alkoxide Chemical class 0.000 claims abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002585 base Substances 0.000 claims abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- 230000001376 precipitating effect Effects 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 abstract description 5
- LJLMNWPXAYKPGV-UHFFFAOYSA-N 2-phenylpiperidine-2-acetamide Chemical compound C=1C=CC=CC=1C(C(=O)N)C1CCCCN1 LJLMNWPXAYKPGV-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 229960001344 methylphenidate Drugs 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000006345 epimerization reaction Methods 0.000 description 3
- INGSNVSERUZOAK-UHFFFAOYSA-N ritalinic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C1CCCCN1 INGSNVSERUZOAK-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PYAPITOPBTXXNJ-UHFFFAOYSA-N 2-phenyl-2-pyridin-2-ylacetamide Chemical compound C=1C=CC=NC=1C(C(=O)N)C1=CC=CC=C1 PYAPITOPBTXXNJ-UHFFFAOYSA-N 0.000 description 2
- CAXNYFPECZCGFK-UHFFFAOYSA-N 2-phenyl-2-pyridin-2-ylacetonitrile Chemical compound C=1C=CC=NC=1C(C#N)C1=CC=CC=C1 CAXNYFPECZCGFK-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- 206010001513 AIDS related complex Diseases 0.000 description 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 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
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- WKNKYEOXIFPICR-UHFFFAOYSA-N 2-phenyl-2-pyridin-2-ylacetic acid Chemical compound C=1C=CC=NC=1C(C(=O)O)C1=CC=CC=C1 WKNKYEOXIFPICR-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 1
- 206010013954 Dysphoria Diseases 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 208000012886 Vertigo Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000006999 cognitive decline Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002743 euphoric effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 231100000889 vertigo Toxicity 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/792,661 US5965734A (en) | 1997-01-31 | 1997-01-31 | Processes and intermediates for preparing 2-substituted piperidine stereoisomers |
| PCT/US1998/010599 WO1999061425A1 (en) | 1997-01-31 | 1998-05-26 | Processes and intermediates for preparing 2-substituted piperidine stereoisomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2320012T3 true ES2320012T3 (es) | 2009-05-18 |
Family
ID=26794135
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES05077084T Expired - Lifetime ES2320012T3 (es) | 1997-01-31 | 1998-05-26 | Procedimientos y productos intermediarios para la preparacion de estereo-isomeros de piperidina 2-sustituida. |
| ES98923727T Expired - Lifetime ES2249830T3 (es) | 1997-01-31 | 1998-05-26 | Procedidmientos y productos intermedios para preparar estereoisomeros de piperidinas 2-sustituidas. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98923727T Expired - Lifetime ES2249830T3 (es) | 1997-01-31 | 1998-05-26 | Procedidmientos y productos intermedios para preparar estereoisomeros de piperidinas 2-sustituidas. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5965734A (enExample) |
| EP (2) | EP1082307B1 (enExample) |
| JP (1) | JP4491135B2 (enExample) |
| AT (2) | ATE304531T1 (enExample) |
| AU (1) | AU765194B2 (enExample) |
| CA (1) | CA2333089C (enExample) |
| CY (1) | CY1108818T1 (enExample) |
| DE (2) | DE69831611T2 (enExample) |
| DK (2) | DK1082307T3 (enExample) |
| ES (2) | ES2320012T3 (enExample) |
| PT (1) | PT1612207E (enExample) |
| WO (1) | WO1999061425A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5837284A (en) * | 1995-12-04 | 1998-11-17 | Mehta; Atul M. | Delivery of multiple doses of medications |
| US6962997B1 (en) * | 1997-05-22 | 2005-11-08 | Celgene Corporation | Process and intermediates for resolving piperidyl acetamide steroisomers |
| US6359139B1 (en) * | 2000-11-07 | 2002-03-19 | Celgene Corporation | Methods for production of piperidyl acetamide stereoisomers |
| US20020187192A1 (en) * | 2001-04-30 | 2002-12-12 | Yatindra Joshi | Pharmaceutical composition which reduces or eliminates drug abuse potential |
| US20030073681A1 (en) * | 2001-08-21 | 2003-04-17 | Hauske James R. | 2-substituted piperidines that are ligands for monoamine receptors and transporters |
| US6638533B2 (en) | 2002-01-03 | 2003-10-28 | George Krsek | Pulse dosage formulations of methylphenidate and method to prepare same |
| US20050239830A1 (en) * | 2004-04-26 | 2005-10-27 | Vikram Khetani | Methods of diminishing co-abuse potential |
| CA2591247A1 (en) * | 2004-12-09 | 2006-06-15 | Celgene Corporation | Treatment of patients suffering from a disease having a family history or diagnosis of tics or tourette's syndrome with d-threo methylphenidate |
| ITMI20042415A1 (it) * | 2004-12-17 | 2005-03-17 | Clariant Lsm Italia Spa | Sintesi di alfa-aril-alfa-piperid-2-il-acetammidi e loro idrolisi acida |
| US9233924B2 (en) | 2014-03-11 | 2016-01-12 | Ampac Fine Chemicals Llc | Methods for preparing D-threo methylphenidate using diazomethane, and compositions thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2507631A (en) * | 1944-01-19 | 1950-05-16 | Ciba Pharm Prod Inc | Pyridine and piperidine compounds and process of making same |
| US2957880A (en) * | 1953-12-23 | 1960-10-25 | Ciba Pharm Prod Inc | Process for the conversion of stereoisomers |
| JPS5630978A (en) * | 1979-08-24 | 1981-03-28 | Kyowa Hakko Kogyo Co Ltd | Novel mitomycin and its preparation |
| US4978744A (en) * | 1989-01-27 | 1990-12-18 | Arizona Board Of Regents | Synthesis of dolastatin 10 |
| US5075315A (en) * | 1990-05-17 | 1991-12-24 | Mcneilab, Inc. | Antipsychotic hexahydro-2H-indeno[1,2-c]pyridine derivatives |
| WO1993019063A1 (en) * | 1992-03-16 | 1993-09-30 | Merck Sharp & Dohme Limited | Benzodiazepine derivatives, compositions containing them and their use in therapy |
| US5696111A (en) * | 1993-11-22 | 1997-12-09 | Merck & Co., Inc. | 3-acylaminobenzazepines |
| EP0771789B1 (en) * | 1995-10-30 | 2000-02-16 | F. Hoffmann-La Roche Ag | 1 alpha, 26-dihydroxy-D-homo-vitamin D3 |
| DE19615119A1 (de) * | 1996-04-17 | 1997-10-23 | Bayer Ag | Neue Arylessigsäureamide |
-
1997
- 1997-01-31 US US08/792,661 patent/US5965734A/en not_active Expired - Lifetime
-
1998
- 1998-05-26 DK DK98923727T patent/DK1082307T3/da active
- 1998-05-26 ES ES05077084T patent/ES2320012T3/es not_active Expired - Lifetime
- 1998-05-26 DE DE69831611T patent/DE69831611T2/de not_active Expired - Lifetime
- 1998-05-26 DK DK05077084T patent/DK1612207T3/da active
- 1998-05-26 CA CA002333089A patent/CA2333089C/en not_active Expired - Lifetime
- 1998-05-26 PT PT05077084T patent/PT1612207E/pt unknown
- 1998-05-26 AT AT98923727T patent/ATE304531T1/de active
- 1998-05-26 WO PCT/US1998/010599 patent/WO1999061425A1/en not_active Ceased
- 1998-05-26 DE DE69840457T patent/DE69840457D1/de not_active Expired - Lifetime
- 1998-05-26 EP EP98923727A patent/EP1082307B1/en not_active Expired - Lifetime
- 1998-05-26 JP JP2000550831A patent/JP4491135B2/ja not_active Expired - Fee Related
- 1998-05-26 AU AU75950/98A patent/AU765194B2/en not_active Expired
- 1998-05-26 AT AT05077084T patent/ATE420073T1/de active
- 1998-05-26 EP EP05077084A patent/EP1612207B1/en not_active Expired - Lifetime
- 1998-05-26 ES ES98923727T patent/ES2249830T3/es not_active Expired - Lifetime
-
2009
- 2009-02-26 CY CY20091100223T patent/CY1108818T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1082307A4 (en) | 2004-04-14 |
| ATE304531T1 (de) | 2005-09-15 |
| PT1612207E (pt) | 2009-02-04 |
| EP1612207B1 (en) | 2009-01-07 |
| WO1999061425A1 (en) | 1999-12-02 |
| HK1090915A1 (en) | 2007-01-05 |
| AU765194B2 (en) | 2003-09-11 |
| EP1082307B1 (en) | 2005-09-14 |
| JP2002516313A (ja) | 2002-06-04 |
| AU7595098A (en) | 1999-12-13 |
| DE69831611T2 (de) | 2006-06-14 |
| EP1082307A1 (en) | 2001-03-14 |
| JP4491135B2 (ja) | 2010-06-30 |
| CA2333089C (en) | 2008-10-14 |
| DE69831611D1 (de) | 2005-10-20 |
| CA2333089A1 (en) | 1999-12-02 |
| US5965734A (en) | 1999-10-12 |
| EP1612207A1 (en) | 2006-01-04 |
| DK1612207T3 (da) | 2009-05-04 |
| ES2249830T3 (es) | 2006-04-01 |
| ATE420073T1 (de) | 2009-01-15 |
| DE69840457D1 (de) | 2009-02-26 |
| CY1108818T1 (el) | 2014-04-09 |
| DK1082307T3 (da) | 2005-12-19 |
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