DE380919C - Process for the preparation of keto derivatives of the morphine series - Google Patents

Process for the preparation of keto derivatives of the morphine series

Info

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
Application number
DEK82619D
Other languages
German (de)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CHEM FAB
Knoll & Co
Original Assignee
CHEM FAB
Knoll & Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DEK76910D priority Critical patent/DE365683C/en
Application filed by CHEM FAB, Knoll & Co filed Critical CHEM FAB
Priority to DEK82619D priority patent/DE380919C/en
Application granted granted Critical
Publication of DE380919C publication Critical patent/DE380919C/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D489/00Heterocyclic 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:
    • C07D489/02Heterocyclic 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 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)

PATENT-AIzspp,ucH,: Abänderung des durch Patent 365683 geschützten Verfahrens zur Darstellung von Ketoderivaten der Morphinreihe, darin bestehend, daß man hier die Katalysatören, im besonderen Palladium und Platin, in Form.von Mohr verwendet.PATENT-AIzspp, ucH,: Modification of the patent protected by patent 365683 Process for the preparation of keto derivatives of the morphine series, consisting of that here the catalysts, especially palladium and platinum, are in the form of Mohr used.
DEK82619D 1921-03-22 1922-07-08 Process for the preparation of keto derivatives of the morphine series Expired DE380919C (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
US9040705B2 (en) 2009-04-09 2015-05-26 Mallinckrodt Llc Preparation of saturated ketone morphinan compounds
US20100261906A1 (en) * 2009-04-09 2010-10-14 Mallinckrodt Inc. Preparation of 6-Keto, 3-Alkoxy Morphinans

Cited By (10)

* Cited by examiner, † Cited by third party
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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