ATE380817T1 - Verfahren zur katalytischen herstellung von hydrocodon und hydromorphon - Google Patents
Verfahren zur katalytischen herstellung von hydrocodon und hydromorphonInfo
- Publication number
- ATE380817T1 ATE380817T1 AT04796303T AT04796303T ATE380817T1 AT E380817 T1 ATE380817 T1 AT E380817T1 AT 04796303 T AT04796303 T AT 04796303T AT 04796303 T AT04796303 T AT 04796303T AT E380817 T1 ATE380817 T1 AT E380817T1
- Authority
- AT
- Austria
- Prior art keywords
- hydromorphone
- hydrocodone
- catalytic production
- analogs
- catalytic
- Prior art date
Links
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 title abstract 3
- 230000003197 catalytic effect Effects 0.000 title abstract 2
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 title abstract 2
- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 title abstract 2
- 229960000240 hydrocodone Drugs 0.000 title abstract 2
- WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 title abstract 2
- 229960001410 hydromorphone Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 title abstract 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 abstract 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229960004126 codeine Drugs 0.000 abstract 1
- 229960005181 morphine Drugs 0.000 abstract 1
- -1 phosphine halide Chemical group 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/495,503 US7323565B2 (en) | 2002-11-11 | 2003-11-05 | Method for the catalytic production of hydrocodone and hydromorphone |
| PCT/US2003/035462 WO2005047291A1 (en) | 2002-11-11 | 2003-11-05 | Method for the catalytic production of hydrocodone and hydromorphone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE380817T1 true ATE380817T1 (de) | 2007-12-15 |
Family
ID=36423513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT04796303T ATE380817T1 (de) | 2003-11-05 | 2004-10-25 | Verfahren zur katalytischen herstellung von hydrocodon und hydromorphon |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7323565B2 (de) |
| EP (1) | EP1687310B1 (de) |
| AT (1) | ATE380817T1 (de) |
| CA (1) | CA2544950A1 (de) |
| DE (1) | DE602004010711T2 (de) |
| ES (1) | ES2295946T3 (de) |
| WO (1) | WO2005113557A1 (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1871774A1 (de) | 2005-03-28 | 2008-01-02 | Mallinckrodt, Inc. | Verfahren zur katalytischen herstellung von hydrocodon, hydromorphon und derivaten davon |
| ES2357216T3 (es) * | 2005-06-16 | 2011-04-20 | Mallinckrodt, Inc. | Una ruta de síntesis de 14-hidroxil-opiáceos a través de 1-halo-tebaína o análogos. |
| US7399859B1 (en) * | 2007-02-06 | 2008-07-15 | Cody Laboratories Inc. | Method for catalytic preparation of hydromorphone and hydrocodone |
| US7999104B2 (en) | 2007-06-29 | 2011-08-16 | Brock University | Methods for one-pot N-demethylation/N-acylation of morphine and tropane alkaloids |
| US8962841B2 (en) | 2007-06-29 | 2015-02-24 | Brock University | Methods for one-pot N-demethylation/N-functionalization of morphine and tropane alkaloids |
| US20100261906A1 (en) * | 2009-04-09 | 2010-10-14 | Mallinckrodt Inc. | Preparation of 6-Keto, 3-Alkoxy Morphinans |
| US8293907B2 (en) * | 2009-04-09 | 2012-10-23 | Mallinckrodt Inc. | Preparation of saturated ketone morphinan compounds by catalytic isomerization |
| WO2010118275A1 (en) * | 2009-04-09 | 2010-10-14 | Mallinckrodt Inc. | Preparation of saturated ketone morphinan compounds |
| PL2563793T3 (pl) | 2010-04-29 | 2015-03-31 | SpecGx LLC | Wytwarzanie nasyconych związków ketonowych morfinanu o niskiej zawartości metalu |
| PL2588481T3 (pl) | 2010-07-02 | 2018-05-30 | Johnson Matthey Public Limited Company | Sposób syntezy i oczyszczania oksykodonu |
| CN103619847A (zh) | 2011-05-06 | 2014-03-05 | 布鲁克大学 | 通过金属催化n-脱甲基化/官能化以及分子内基团转移制备吗啡类似物的方法 |
| DK3166923T3 (da) | 2014-07-10 | 2023-04-11 | SpecGx LLC | Fremgangsmåde til fremstilling af substituerede phenylalkaner |
| US9914695B2 (en) | 2015-07-10 | 2018-03-13 | Mallinckrodt Llc | Two-step process for preparing 3-substituted phenylalkylamines |
| EP3255051A1 (de) | 2016-06-09 | 2017-12-13 | Siegfried AG | Trägerbasierter metallkatalysator für die herstellung von hydrocodon und hydromorphon |
| US10081636B2 (en) | 2016-07-08 | 2018-09-25 | Cody Laboratories, Inc. | Method for catalytic preparation of hydromorphone, hydrocodone, and other opiates |
| WO2022101408A1 (en) | 2020-11-13 | 2022-05-19 | Ferrer Internacional, S.A. | Synthesis of hydromorphone base |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2577947A (en) | 1951-12-11 | Manufacture of dihydrocodeinone | ||
| DE365683C (de) | 1921-03-22 | 1922-12-22 | Knoll & Co Chem Fab | Verfahren zur Darstellung von Ketoderivaten der Morphinreihe |
| DE415097C (de) | 1923-10-19 | 1925-06-13 | Chem Fab | Verfahren zur Darstellung von Dihydrokodeinon |
| DE607931C (de) | 1934-01-26 | 1935-01-11 | Chemische Fabriken | Verfahren zur Darstellung von Dihydromorphinonen |
| US2577847A (en) * | 1948-10-16 | 1951-12-11 | Allied Chem & Dye Corp | Purification of chlorocarbons |
| US2544291A (en) | 1949-04-05 | 1951-03-06 | New York Quinine And Chemical | Alkaloid manufacture |
| US2628962A (en) | 1949-10-20 | 1953-02-17 | Mallinckrodt Chemical Works | Method for preparing dihydrocodeinone, dihydromorphinone, and codeinone |
| US2654756A (en) | 1949-10-20 | 1953-10-06 | Mallinckrodt Chemical Works | Process of preparing codeinone, dihydrocodeinone, and dihydromorphinone |
| US2715626A (en) | 1950-07-05 | 1955-08-16 | Merck & Co Inc | Process of preparing dihydrocodeinone |
| US2649454A (en) | 1951-08-20 | 1953-08-18 | Univ California | Method for preparing dihydromorphinone, dihydrocodeinone, and dihydropseudocodeinone |
| US4003903A (en) | 1975-02-12 | 1977-01-18 | Florida Board Of Regents | N-acyl-N-norsalutaridines and process for making them |
| US4322426A (en) | 1980-04-28 | 1982-03-30 | E. I. Du Pont De Nemours And Company | 17-Substituted-6-desoxy-7,8-dihydro-6α-methylnoroxymorphone narcotic antagonists |
| US4368326A (en) | 1980-07-03 | 1983-01-11 | Rice Kenner C | Short total synthesis of dihydrothebainone, dihydrocodeinone, and nordihydroccodeinone |
| US4478840A (en) | 1983-10-11 | 1984-10-23 | E. I. Du Pont De Nemours And Company | Appetite suppressing compositions and methods |
| US4535157A (en) | 1983-11-01 | 1985-08-13 | Key Pharmaceuticals, Inc. | Process for making 6-desoxy-6-methylenenaloxone and 6-desoxy-6-methylenenaltrexone |
| US4613668A (en) | 1983-12-22 | 1986-09-23 | The United States Of America As Represented By The Department Of Health And Human Services | Short total synthesis or morphinan compounds which uses cyclization of a cycloalkylcarbonyl compound selected from cyclopropylcarbonyl and cyclobutylcarbonyl |
| GB9213524D0 (en) | 1992-06-25 | 1992-08-12 | Macfarlan Smith Ltd | Biocatalysis in the synthesis of analgesic and antitussive compounds |
| GB9616253D0 (en) * | 1996-08-01 | 1996-09-11 | Johnson Matthey Plc | Preparation of narcotic analgesics |
| GB9805516D0 (en) | 1998-03-17 | 1998-05-13 | Johnson Matthey Plc | Preparation of opiates |
| US6177567B1 (en) | 1999-10-15 | 2001-01-23 | Boehringer Ingelheim Chemicals, Inc. | Method for preparing oxycodone |
| MXPA02004678A (es) | 1999-11-09 | 2005-10-05 | Abbott Laboratoires | Composiciones de hidrocodeinona e hdromorfinona y metodos para su sintesis. |
-
2003
- 2003-11-05 US US10/495,503 patent/US7323565B2/en not_active Expired - Fee Related
-
2004
- 2004-10-25 DE DE602004010711T patent/DE602004010711T2/de not_active Expired - Fee Related
- 2004-10-25 CA CA002544950A patent/CA2544950A1/en not_active Abandoned
- 2004-10-25 EP EP04796303A patent/EP1687310B1/de not_active Expired - Lifetime
- 2004-10-25 WO PCT/US2004/035292 patent/WO2005113557A1/en not_active Ceased
- 2004-10-25 AT AT04796303T patent/ATE380817T1/de not_active IP Right Cessation
- 2004-10-25 ES ES04796303T patent/ES2295946T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005113557A1 (en) | 2005-12-01 |
| EP1687310B1 (de) | 2007-12-12 |
| CA2544950A1 (en) | 2005-12-01 |
| ES2295946T3 (es) | 2008-04-16 |
| US20060074239A1 (en) | 2006-04-06 |
| WO2005113557A8 (en) | 2006-05-26 |
| EP1687310A1 (de) | 2006-08-09 |
| DE602004010711T2 (de) | 2008-12-04 |
| US7323565B2 (en) | 2008-01-29 |
| DE602004010711D1 (de) | 2008-01-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |