DE607931C - Process for the preparation of dihydromorphinones - Google Patents
Process for the preparation of dihydromorphinonesInfo
- Publication number
- DE607931C DE607931C DES112645A DES0112645A DE607931C DE 607931 C DE607931 C DE 607931C DE S112645 A DES112645 A DE S112645A DE S0112645 A DES0112645 A DE S0112645A DE 607931 C DE607931 C DE 607931C
- Authority
- DE
- Germany
- Prior art keywords
- yield
- dissolved
- refluxed
- dihydromorphinones
- theory
- 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
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 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 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229960005181 morphine Drugs 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 2
- 229930013930 alkaloid Natural products 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000008379 phenol ethers Chemical class 0.000 claims description 2
- 150000003057 platinum Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 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 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 229960004126 codeine Drugs 0.000 description 5
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229960000240 hydrocodone Drugs 0.000 description 3
- 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 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- KTAPPOXVPBBPRF-ATNYCFDYSA-N (4R,4aR,7aR,12bS)-9-ethoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one Chemical compound C(C)OC=1C=CC=2C[C@@H]3[C@@H]4CCC([C@H]5[C@@]4(C=2C=1O5)CCN3C)=O KTAPPOXVPBBPRF-ATNYCFDYSA-N 0.000 description 1
- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 1
- DYXBSXBXZNSAPO-UHFFFAOYSA-M 1,1-dimethylpyrrolidin-1-ium;iodide Chemical compound [I-].C[N+]1(C)CCCC1 DYXBSXBXZNSAPO-UHFFFAOYSA-M 0.000 description 1
- APLNAFMUEHKRLM-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)N=CN2 APLNAFMUEHKRLM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OGDVEMNWJVYAJL-LEPYJNQMSA-N Ethyl morphine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OCC OGDVEMNWJVYAJL-LEPYJNQMSA-N 0.000 description 1
- OGDVEMNWJVYAJL-UHFFFAOYSA-N Ethylmorphine Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OCC OGDVEMNWJVYAJL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960001012 codeine hydrochloride Drugs 0.000 description 1
- 229960004415 codeine phosphate Drugs 0.000 description 1
- 229960004578 ethylmorphine Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229960001410 hydromorphone Drugs 0.000 description 1
- 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 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- XCKKIKBIPZJUET-VYKNHSEDSA-N morphine hydrochloride Chemical compound Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O XCKKIKBIPZJUET-VYKNHSEDSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- -1 platinum metals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 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
Description
Verfahren zur Darstellung von Dihydromorphinonen Es ist bereits bekannt, daß das Morphin und seine Phenoläther durch Behandlung mit molekularem Wasserstoff in Gegenwart größerer Mengen Edelmetallkatalysatoren durch Erhitzen der sauren Lösung in die dihydrierten Ketoderivate übergeführt werden können.Process for the preparation of dihydromorphinones It is already known that the morphine and its phenol ethers by treatment with molecular hydrogen in the presence of large amounts of noble metal catalysts by heating the acidic solution can be converted into the dihydrogenated keto derivatives.
Überraschenderweise wurde nun gefunden, daß für diesen Enderfolg die Zufuhr von Wasserstoff überhaupt entbehrlich ist und daß ein einfaches Erhitzen der sauren Alkaloidlösüngen mit größeren Mengen fein verteilten Platinmetallen genügt, um die gleichzeitige Dehydrierung und Hydrierung mit guten Ausbeuten durchzuführen. Dieser Erfolg ist besonders darum unerwartet, weil nicht vorauszusehen war, daß das nicht mit Wasserstoff abgesättigte Platinmetall imstande ist, den aus der Dehydrierung (s. Formel 111, 6) stammenden Wasserstoff praktisch restlos zur Hydrierung der Kerndoppelbindung (s. Formel 111, 7 und 8) des Morphins bzw. seiner Abkömmlinge zu verwenden, ohne daß dazu ein. Überschuß von molekularem Wasserstoff von außen zugeführt werden braucht.Surprisingly, it has now been found that for this ultimate success Supply of hydrogen is dispensable at all and that a simple heating the acidic alkaloid solutions with larger amounts of finely divided platinum metals are sufficient, to carry out the simultaneous dehydrogenation and hydrogenation with good yields. This success is particularly unexpected because it was not foreseeable that the platinum metal, which is not saturated with hydrogen, is capable of producing that from dehydrogenation (see formula 111, 6) originating hydrogen practically completely for the hydrogenation of the core double bond (see formula III, 7 and 8) of morphine or its derivatives to use without that to one. Excess of molecular hydrogen needs to be supplied from the outside.
Der Reaktionsverlauf wird durch folgendes Formelbild veranschaulicht: Beispiel r 3oo g Codeinbase werden in 2 1 verdünnter Salzsäure gelöst und nach Zugabe von 150 9 fein verteiltem Palladium einige Stunden am Rückflußkühler zum Sieden erhitzt. Nach.. dem Abfiltrieren des Palladiums wird das saure Filtrat mit Natronlauge übersättigt. Die ausgeschiedene Base wird aus Alkoholumkristallisiert.- Schmelzpunkt 1g5°. Ausbeute an Dihydrocodeinon 75 bis 85 0fo .der Theorie. Beispiel e 59 salzsaures Codein werden in 3o ccm Wasser gelöst, mit wenig Salzsäure angesäuert und nach Zugabe von q. g Platinmohr 5 Stunden unter Rückfluß gekocht. Aufarbeitung gemäß Beispiel i. Ausbeute 65 bis 75 0/0 der Theorie. Beispiel 3 5 g salzsaures Morphin, in 50 ccin schwach salzsäurehaltigem Wasser gelöst, werden in Gegenwart von 5 g Platinmohr q. Stunden unter Rückfluß gekocht. Aufarbeitung nach Beispiel i. Ausbeute 2,5 g Dihydromorphinon.The course of the reaction is illustrated by the following formula: Example R 3oo grams of codeine are dissolved in 2 1 of dilute hydrochloric acid and heated to boiling by the addition of 150 9 of finely divided palladium several hours at reflux. After the palladium has been filtered off, the acidic filtrate is supersaturated with sodium hydroxide solution. The precipitated base is recrystallized from alcohol - melting point 1g5 °. Yield of dihydrocodeinone 75 to 85% according to theory. Example e 59 codeine hydrochloric acid are dissolved in 3o ccm water, acidified with a little hydrochloric acid and, after adding q. g platinum black refluxed for 5 hours. Working up according to example i. Yield 65 to 75% of theory. EXAMPLE 3 5 g of hydrochloric acid morphine, dissolved in 50 cc in weakly hydrochloric acid-containing water, are q in the presence of 5 g of platinum black. Boiled under reflux for hours. Working up according to example i. Yield 2.5 g of dihydromorphinone.
Beispiel q. Eine schwach salzsaure, wässerige Lösung von 6 g Codeinhydrochlorid wird mit 5o ccm einer io01oigen kolloidalen Platinlösung versetzt und unter Rückfluß 3 Stunden gekocht. Aufarbeitung wie in Beispiel i. Ausbeute 3 g Dihydrocodeinon.Example q. A weak hydrochloric acid, aqueous solution of 6 g codeine hydrochloride 50 cc of a 100% colloidal platinum solution are added and the mixture is refluxed Cooked for 3 hours. Working up as in example i. Yield 3 g of dihydrocodeinone.
Beispiels 6 g Codeinbase werden in -3o ccm Wasser unter Zusatz von q. g Weinsäure gelöst, dazu 6 g Palladiummohr zugefügt und unter Rückfluß i Stunde gekocht. Aufarbeitung wie in Beispiel i. Ausbeute an Dihydrocodeinon 75 01, der Theorie. Beispiel 6 6 g Codeinphosphat werden in 30 ccm Wasser gelöst, mit 5 ccm verdünnter Phospliorsäure angesäuert, mit g. g fein verteiltem Palladium versetzt und i Stunde am Rück flußkühler gekocht. Aufarbeitung wie in Beispiel i. Ausbeute 6o bis 7o % der Theorie. Beispiel17 6 g Codeinbase werden in verdünnter Essigsäure gelöst und nach Zusatz von 5 g Palladiummohr 2 Stunden unter Rückfluß gekocht. Ausbeute q.o % der Theorie. Beispiel 8 21 g Codeinbase werden in überschüssiger verdünnter Schwefelsäure gelöst, mit 16 g Palladiummohr versetzt und i Stunde unter Rückfluß gekocht. Ausbeute 8o bis 85 0lo der Theorie. Beispiel g io g Äthylmorphin werden in 5o ccm Wasser unter Zusatz von Salzsäure bis zur sauren Reaktion gelöst, mit io g Platinmohr versetzt und unter Rückfluß gekocht. Aufarbeitung wie in Beispiel i. Ausbeute an Äthyldihydromorphinon vom F. iog° (unscharf) 65 bis 70 % der Theorie.Example 6 g of codeine base are dissolved in -3o ccm of water with the addition of q. g of tartaric acid dissolved, 6 g of palladium black were added and the mixture was refluxed for 1 hour. Working up as in example i. Yield of dihydrocodeinone 75 01, the theory. Example 6 6 g of codeine phosphate are dissolved in 30 cc of water, acidified with 5 cc of dilute phosphoric acid, with g. g of finely divided palladium are added and the mixture is refluxed for 1 hour. Working up as in example i. Yield 6o to 7o% of theory. Example 17 6 g of codeine base are dissolved in dilute acetic acid and, after addition of 5 g of palladium black, refluxed for 2 hours. Yield qo% of theory. Example 8 21 g of codeine base are dissolved in excess dilute sulfuric acid, 16 g of palladium black are added and the mixture is refluxed for 1 hour. Yield 80 to 8500 of theory. EXAMPLE 100 g of ethyl morphine are dissolved in 50 cc of water with the addition of hydrochloric acid until an acidic reaction occurs, 10 g of platinum black are added and the mixture is refluxed. Working up as in example i. Yield of ethyl dihydromorphinone from the temperature iog ° (unsharp) 65 to 70% of theory.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES112645A DE607931C (en) | 1934-01-26 | 1934-01-26 | Process for the preparation of dihydromorphinones |
| DEK134993A DE617238C (en) | 1934-01-26 | 1934-07-12 | Process for the preparation of dihydromorphinones |
| DE1934K0136273 DE623821C (en) | 1934-01-26 | 1934-08-16 | Process for the preparation of dihydromorphinones |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES112645A DE607931C (en) | 1934-01-26 | 1934-01-26 | Process for the preparation of dihydromorphinones |
| DEK134993A DE617238C (en) | 1934-01-26 | 1934-07-12 | Process for the preparation of dihydromorphinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE607931C true DE607931C (en) | 1935-01-11 |
Family
ID=59097976
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES112645A Expired DE607931C (en) | 1934-01-26 | 1934-01-26 | Process for the preparation of dihydromorphinones |
| DEK134993A Expired DE617238C (en) | 1934-01-26 | 1934-07-12 | Process for the preparation of dihydromorphinones |
| DE1934K0136273 Expired DE623821C (en) | 1934-01-26 | 1934-08-16 | Process for the preparation of dihydromorphinones |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK134993A Expired DE617238C (en) | 1934-01-26 | 1934-07-12 | Process for the preparation of dihydromorphinones |
| DE1934K0136273 Expired DE623821C (en) | 1934-01-26 | 1934-08-16 | Process for the preparation of dihydromorphinones |
Country Status (1)
| Country | Link |
|---|---|
| DE (3) | DE607931C (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2544291A (en) * | 1949-04-05 | 1951-03-06 | New York Quinine And Chemical | Alkaloid manufacture |
| US6512117B1 (en) | 1999-11-09 | 2003-01-28 | Abbott Laboratories | Hydromorphone and hydrocodone compositions and methods for their synthesis |
| CZ297571B6 (en) * | 2004-04-13 | 2007-02-07 | Zentiva, A. S. | Process for preparing 4,5 alpha-epoxy-6-oxomorphinan derivatives |
| US7321038B2 (en) | 2002-11-11 | 2008-01-22 | Mallinckrodt Inc. | Method for the catalytic production of hydrocodone and hydromorphone |
| US7323565B2 (en) | 2002-11-11 | 2008-01-29 | Mallinckrodt Inc. | Method for the catalytic production of hydrocodone and hydromorphone |
| US7399859B1 (en) | 2007-02-06 | 2008-07-15 | Cody Laboratories Inc. | Method for catalytic preparation of hydromorphone and hydrocodone |
| US7399858B2 (en) | 2002-11-11 | 2008-07-15 | Mallinckrodt Inc. | Method for the catalytic production of hydrocodone, hydromorphone, and derivatives thereof |
| US9040705B2 (en) | 2009-04-09 | 2015-05-26 | Mallinckrodt Llc | Preparation of saturated ketone morphinan compounds |
| EP3255051A1 (en) | 2016-06-09 | 2017-12-13 | Siegfried AG | Supported metal catalyst for the production of hydrocodon and hydromorphon |
| US10081636B2 (en) | 2016-07-08 | 2018-09-25 | Cody Laboratories, Inc. | Method for catalytic preparation of hydromorphone, hydrocodone, and other opiates |
| US10370382B2 (en) | 2015-07-27 | 2019-08-06 | Cambrex Charles City, Inc. | Process for preparing hydromorphone and derivatives thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201313211D0 (en) | 2013-07-24 | 2013-09-04 | Cambrex Karlskoga Ab | New process |
-
1934
- 1934-01-26 DE DES112645A patent/DE607931C/en not_active Expired
- 1934-07-12 DE DEK134993A patent/DE617238C/en not_active Expired
- 1934-08-16 DE DE1934K0136273 patent/DE623821C/en not_active Expired
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2544291A (en) * | 1949-04-05 | 1951-03-06 | New York Quinine And Chemical | Alkaloid manufacture |
| EP2003134A2 (en) | 1999-11-09 | 2008-12-17 | Abbott Laboratories | Hydromorphinone and hydrocodeinone compositions and methods for their synthesis |
| US6512117B1 (en) | 1999-11-09 | 2003-01-28 | Abbott Laboratories | Hydromorphone and hydrocodone compositions and methods for their synthesis |
| EP2338891A3 (en) * | 1999-11-09 | 2011-10-26 | Abbott Laboratories | Method of forming hydromorphinone compositions |
| EP1233966B2 (en) † | 1999-11-09 | 2011-10-19 | Abbott Laboratories | Hydromorphinone and hydrocodeinone compositions and methods for their synthesis |
| EP2338891A2 (en) | 1999-11-09 | 2011-06-29 | Abbott Laboratories | Method of forming hydromorphinone compositions |
| US7323565B2 (en) | 2002-11-11 | 2008-01-29 | Mallinckrodt Inc. | Method for the catalytic production of hydrocodone and hydromorphone |
| US7399858B2 (en) | 2002-11-11 | 2008-07-15 | Mallinckrodt Inc. | Method for the catalytic production of hydrocodone, hydromorphone, and derivatives thereof |
| US7321038B2 (en) | 2002-11-11 | 2008-01-22 | Mallinckrodt Inc. | Method for the catalytic production of hydrocodone and hydromorphone |
| CZ297571B6 (en) * | 2004-04-13 | 2007-02-07 | Zentiva, A. S. | Process for preparing 4,5 alpha-epoxy-6-oxomorphinan derivatives |
| US7399859B1 (en) | 2007-02-06 | 2008-07-15 | Cody Laboratories Inc. | Method for catalytic preparation of hydromorphone and hydrocodone |
| US9040705B2 (en) | 2009-04-09 | 2015-05-26 | Mallinckrodt Llc | Preparation of saturated ketone morphinan compounds |
| US10370382B2 (en) | 2015-07-27 | 2019-08-06 | Cambrex Charles City, Inc. | Process for preparing hydromorphone and derivatives thereof |
| EP3255051A1 (en) | 2016-06-09 | 2017-12-13 | Siegfried AG | Supported metal catalyst for the production of hydrocodon and hydromorphon |
| WO2017211879A1 (en) | 2016-06-09 | 2017-12-14 | Siegfried Ag | Supported metal catalyst for the production of hydrocodone and hydromorphone |
| US10081636B2 (en) | 2016-07-08 | 2018-09-25 | Cody Laboratories, Inc. | Method for catalytic preparation of hydromorphone, hydrocodone, and other opiates |
Also Published As
| Publication number | Publication date |
|---|---|
| DE617238C (en) | 1935-10-02 |
| DE623821C (en) | 1936-01-06 |
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