DE380919C - Process for the preparation of keto derivatives of the morphine series - Google Patents
Process for the preparation of keto derivatives of the morphine seriesInfo
- Publication number
- DE380919C DE380919C DEK82619D DEK0082619D DE380919C DE 380919 C DE380919 C DE 380919C DE K82619 D DEK82619 D DE K82619D DE K0082619 D DEK0082619 D DE K0082619D DE 380919 C DE380919 C DE 380919C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- morphine
- keto derivatives
- series
- morphine series
- 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
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)
Description
Verfahren zur Darstellung von Ketoderivaten der Norphinreihe. Durch Patent 365683 ist ein Verfahren zur Darstellung von Ketoderivaten der Morphinreihe geschützt, welches darin besteht, daß man Morphin oder seine ®-Alkyläther mit molekularem- Wasserstoff bei Gegenwart von Säure mit verhältnismäßig großen Mengen Katalysatoren, im besonderen Palladium und Platin oder deren Salze, behandelt.Process for the preparation of keto derivatives of the norphin series. By Patent 365683 is a process for the preparation of keto derivatives of the morphine series protected, which consists in the fact that morphine or its ® -alkyl ethers with molecular- Hydrogen in the presence of acid with relatively large amounts of catalysts, in particular palladium and platinum or their salts.
In Weiterbildung dieses Verfahrens wurde nun gefunden, daß es nicht nur auf die Menge an geeigneten Katalysatoren, sondern auch auf die Form ankommt, in der sie angewandt werden, um die beabsichtigte Wirkung zu erzielen. Letztere beruht darauf, daß die alkoholische ITydroxylgruppe des Morphin=. moleküls (an C8 der Morphinformel nach Knorr) durch den Katalysator -dehydriert wird, und daß durch die Anlagefung dieser beiden Wasserstoffatome an die C-Atome 8 +1q.. der- Knorrschen Morphinformel diedort angenommene Doppelbindung aufgelöst wird. -Die Wirkung selbst wird nach den bisherigen Versuchen am vorteilhaftesten erzielt, wenn der Katalysator' in Form von Mohr angewandt wird. Die nach dem Verfahren erhaltenen Basen können auch acidyliert werden.In a further development of this process it has now been found that it is not only depends on the amount of suitable catalysts, but also on the shape, in which they are used to achieve the intended effect. Latter is based on the fact that the alcoholic hydroxyl group of morphine =. molecule (at C8 the morphine formula according to Knorr) is -dehydriert by the catalyst, and that by the attachment of these two hydrogen atoms to the carbon atoms 8 + 1q .. der- Knorrschen Morphine formula the double bond assumed there is dissolved. -The effect itself is achieved most advantageously according to the previous attempts if the catalyst ' in the form of Mohr is applied. The bases obtained by the process can can also be acidylated.
Beispiel x.Example x.
25 g salzsaures Morphin werden in 125 ccm Wasser gelöst und mit 39 Palladiummohr, 1q. ccm konzentrierter Salzsäure und mit Wasserstoff bei 6o bis 9o° C unter 30 cm Wasserüberdruck behandelt. Die Abscheidung erfolgt, wie im Hauptpatent angegeben ist. Der Katalysator kann überverwendet werden.25 g of hydrochloric acid morphine are dissolved in 125 ccm of water and treated with 39 palladium black, 1q. ccm of concentrated hydrochloric acid and treated with hydrogen at 6o to 9o ° C under 30 cm of water pressure. The deposition takes place as indicated in the main patent. The catalyst can be overused.
Beispiel z.Example
25 g salzsaures Codein werden, wie in-Beispiel x angegeben, behandelt. - -25 g of codeine hydrochloric acid are treated as indicated in example x. - -
Claims (1)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEK76910D DE365683C (en) | 1921-03-22 | 1921-03-22 | Process for the preparation of keto derivatives of the morphine series |
DEK82619D DE380919C (en) | 1921-03-22 | 1922-07-08 | Process for the preparation of keto derivatives of the morphine series |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEK76910D DE365683C (en) | 1921-03-22 | 1921-03-22 | Process for the preparation of keto derivatives of the morphine series |
DEK82619D DE380919C (en) | 1921-03-22 | 1922-07-08 | Process for the preparation of keto derivatives of the morphine series |
Publications (1)
Publication Number | Publication Date |
---|---|
DE380919C true DE380919C (en) | 1923-09-13 |
Family
ID=33030661
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEK76910D Expired DE365683C (en) | 1921-03-22 | 1921-03-22 | Process for the preparation of keto derivatives of the morphine series |
DEK82619D Expired DE380919C (en) | 1921-03-22 | 1922-07-08 | Process for the preparation of keto derivatives of the morphine series |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEK76910D Expired DE365683C (en) | 1921-03-22 | 1921-03-22 | Process for the preparation of keto derivatives of the morphine series |
Country Status (1)
Country | Link |
---|---|
DE (2) | DE365683C (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6512117B1 (en) | 1999-11-09 | 2003-01-28 | Abbott Laboratories | Hydromorphone and hydrocodone compositions and methods for their synthesis |
WO2005100361A1 (en) * | 2004-04-13 | 2005-10-27 | Zentiva, A.S. | A METHOD OF PREPARATION OF 4,5α-EPOXY-6-OXOMORPHINAN DERIVATIVES |
US7399859B1 (en) | 2007-02-06 | 2008-07-15 | Cody Laboratories Inc. | Method for catalytic preparation of hydromorphone and hydrocodone |
EP3255051A1 (en) | 2016-06-09 | 2017-12-13 | Siegfried AG | Supported metal catalyst for the production of hydrocodon and hydromorphon |
US9981978B2 (en) | 2013-07-24 | 2018-05-29 | Cambrex Charles City, Inc. | Preparation of saturated ketone morphinan compounds by catalytic isomerisation |
US10081636B2 (en) | 2016-07-08 | 2018-09-25 | Cody Laboratories, Inc. | Method for catalytic preparation of hydromorphone, hydrocodone, and other opiates |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO2010118275A1 (en) | 2009-04-09 | 2010-10-14 | Mallinckrodt Inc. | Preparation of saturated ketone morphinan compounds |
US20100261906A1 (en) * | 2009-04-09 | 2010-10-14 | Mallinckrodt Inc. | Preparation of 6-Keto, 3-Alkoxy Morphinans |
-
1921
- 1921-03-22 DE DEK76910D patent/DE365683C/en not_active Expired
-
1922
- 1922-07-08 DE DEK82619D patent/DE380919C/en not_active Expired
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6512117B1 (en) | 1999-11-09 | 2003-01-28 | Abbott Laboratories | Hydromorphone and hydrocodone compositions and methods for their synthesis |
EP2003134A2 (en) | 1999-11-09 | 2008-12-17 | 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 |
WO2005100361A1 (en) * | 2004-04-13 | 2005-10-27 | Zentiva, A.S. | A METHOD OF PREPARATION OF 4,5α-EPOXY-6-OXOMORPHINAN DERIVATIVES |
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 |
US9981978B2 (en) | 2013-07-24 | 2018-05-29 | Cambrex Charles City, Inc. | Preparation of saturated ketone morphinan compounds by catalytic isomerisation |
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 |
---|---|
DE365683C (en) | 1922-12-22 |
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