DE296916C - - Google Patents
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- Publication number
- DE296916C DE296916C DENDAT296916D DE296916DA DE296916C DE 296916 C DE296916 C DE 296916C DE NDAT296916 D DENDAT296916 D DE NDAT296916D DE 296916D A DE296916D A DE 296916DA DE 296916 C DE296916 C DE 296916C
- Authority
- DE
- Germany
- Prior art keywords
- oxycodeinone
- solution
- water
- acetic acid
- dissolved
- 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.)
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- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycontin Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 229960002085 oxycodone Drugs 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 2
- FQXXSQDCDRQNQE-VMDGZTHMSA-N Thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- -1 platinum group metals Chemical class 0.000 claims description 2
- 229930003945 thebaine Natural products 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 229960000583 Acetic Acid Drugs 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MFSIEROJJKUHBQ-UHFFFAOYSA-N O.[Cl] Chemical compound O.[Cl] MFSIEROJJKUHBQ-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000001376 precipitating Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 229940013123 stannous chloride Drugs 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin dichloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- HFBYLYCMISIEMM-FFHNEAJVSA-N (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid Chemical class 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 HFBYLYCMISIEMM-FFHNEAJVSA-N 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L Zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 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:
- C07D489/06—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 a hetero atom directly attached in position 14
- C07D489/08—Oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Das nach dem Verfahren der Patentschrift 286431 erhältliche Oxydationsprodukt des Thebains vom F. 275 ° und der Zusammensetzung : C18 H19 N O4, das als »Oxycodeinon« bezeichnet werden soll, liefert, wie gefunden wurde, je nach Wahl des Reduktionsmittels drei verschiedene Dihydroderivate, welche isomer sind und die empirische Zusammensetzung :The oxidation product of thebaine with a temperature of 275 ° and the composition: C 18 H 19 NO 4 , which is to be referred to as "oxycodeinone", provides three different dihydro derivatives, depending on the choice of reducing agent, as has been found , which are isomeric and the empirical composition:
C18H21NO4 C 18 H 21 NO 4
aufweisen.exhibit.
Das erste dieser 3 isomeren Reduktionsprodukte (vgl. unten Beispiel I) wird bei der Behandlung des bei 275 ° schmelzenden Oxycodeinons mit molekularem Wasserstoff bei Gegenwart von feinverteilten Metallen der Platingruppe oder kolloidalen Lösungen dieser Metalle erhalten. Es bildet sich auch beim Kochen von Oxycodeinon mit Natriumhydrosulfitlösung. Aus Alkohol kristallisiert dieses Dihydrooxycodeinon in langgestreckten, ausgezackten Säulen vom F. 222 °; es liefert gut kristallisierte Salze. Das ChlorhydratThe first of these 3 isomeric reduction products (see. Example I below) is used in the treatment of the oxycodeinone melting at 275 ° with molecular hydrogen in the presence of finely divided platinum group metals or colloidal solutions of these metals obtain. It is also formed when oxycodeinone is boiled with sodium hydrosulfite solution. This dihydrooxycodeinone crystallizes from alcohol in elongated, jagged ones Pillars with a mp of 222 °; it provides well-crystallized salts. The hydrochloride
C18H21NO4.C 18 H 21 NO 4 .
HClHCl
kristallisiert aus Wasser oder verdünntem Alkohol in Säulen vom F. 268 bis 270°. Aus den Lösungen der Salze wird die freie Base durch Ammoniak, Soda oder Alkali gefällt; im Überschuß von Alkali ist sie unlöslich. Sie bildet ein Jodmethylat C18 H21N O4 · CH3 J, Prismen vom Zersetzungspunkt 251 °. Der Ketocharakter der Verbindung gibt sich durch die Bildung eines Oxims zu erkennen, dessen Chlorhydrat: C18 H22 N2 O4- H Cl in Stäbchen vom Zersetzungspunkt 275 bis 278 ° abgeschieden werden kann.crystallizes from water or dilute alcohol in columns with a melting point of 268 to 270 °. The free base is precipitated from the solutions of the salts by ammonia, soda or alkali; in excess of alkali it is insoluble. It forms an iodine methylate C 18 H 21 NO 4 · CH 3 I, prisms with a decomposition point of 251 °. The keto character of the compound is evident from the formation of an oxime, the hydrochloride of which: C 18 H 22 N 2 O 4 - H Cl can be deposited in rods from a decomposition point of 275 to 278 °.
Das zweite Reduktionsprodukt des Oxycodeinons (vgl. unten Beispiel II) bildet sich bei der Behandlung der Base mit Zinkstaub in Eisessiglösung und besitzt ebenfalls die Formel:The second reduction product of oxycodeinone (cf. Example II below) is formed the treatment of the base with zinc dust in glacial acetic acid solution and also has the formula:
C18H21NO4.C 18 H 21 NO 4 .
Der Schmelzpunkt liegt bei 293°. Es kristallisiert aus einem Gemisch von Chloroform und Alkohol in prismatischen Stäbchen. Mit Essigsäureanhydrid entsteht ein aus Alkohol in Blättchen kristallisierendes Acetylderivat vom Zersetzungspunkt 283° und der Zusammensetzung: C20H23NO5. Es bildet ein gut kristallisiertes Chlorhydrat, aus welchem Soda, Ammoniak und überschüssiges Alkali die freie Base abscheiden. Mit Hydroxylamin liefert sie kein Oxim. In der neuen Verbindung liegt wahrscheinlich ein »Oxycodein« vor.The melting point is 293 °. It crystallizes from a mixture of chloroform and alcohol in prismatic rods. With acetic anhydride, an acetyl derivative crystallizes from alcohol in flakes and has a decomposition point of 283 ° and has the composition: C 20 H 23 NO 5 . It forms a well-crystallized hydrochloride, from which soda, ammonia and excess alkali separate the free base. With hydroxylamine, it does not provide an oxime. There is probably an "oxycodeine" in the new compound.
Ein drittes Reduktionsprodukt des Oxycodeinons (vgl. unten Beispiel III) entsteht beim Erhitzen des Oxycodeinons mit Stannochlorid und Salzsäure und kann in Form des Chlorhydrats, ^ das aus Wasser aus derben Säulen kristallisiert, abgeschieden werden. Dieses Chlorhydrat schmilzt oberhalb 280° und besitzt die Zusammensetzung:A third reduction product of oxycodeinone (see. Example III below) arises at Heating of the oxycodeinone with stannous chloride and hydrochloric acid and can in the form of the chlorohydrate, ^ which crystallizes from water from coarse columns, are separated. This Chlorohydrate melts above 280 ° and has the composition:
C18H21NO4-HCl.C 18 H 21 NO 4 -HCl.
Aus dem Chlorhydrat scheidet Ammoniak die freie Base in Flocken ab, die in NatronlaugeFrom the chlorine hydrate, ammonia separates the free base in flakes, and that in sodium hydroxide solution
leicht löslich sind. Die Base liefert ein Oxim von der Zusammensetzung: C18H22N2O4 und dem Zersetzungspunkt 255°.are easily soluble. The base provides an oxime with the composition: C 18 H 22 N 2 O 4 and the decomposition point 255 °.
Die neuen Verbindungen sollen als Arzneimittel Verwendung finden.The new compounds are to be used as pharmaceuticals.
a) 10 g Oxycodeinon werden in verdünnter Essigsäure gelöst und die mit Wasser auf etwa 100 ecm gebrachte Lösung nach Zusatz von etwas Platinmohr mit Wasserstoff geschüttelt, wobei im Laufe von etwa 4 Stunden die einem Mol. Wasserstoff entsprechende Absorption eintritt. Nach Abfiltrieren des Platins gibt die essigsaure Lösung beim Übersättigen mit Ammoniak in quantitativer Ausbeute die hydrierte Base, welche, aus Alkohol umkristallisiert, bei 222° schmilzt.a) 10 g of oxycodeinone are dissolved in dilute acetic acid and diluted with water to about 100 ecm solution after adding some platinum black shaken with hydrogen, the absorption corresponding to one mole of hydrogen occurs in the course of about 4 hours. After filtering off the platinum, the acetic acid solution is supersaturated with ammonia in quantitative yield the hydrogenated base, which, recrystallized from alcohol, at 222 ° melts.
b) Der Versuch verläuft in derselben Weise, wenn man 10 g Oxycodeinon in Wasser suspendiert, mit 32 ecm Normalessigsäure versetzt und die erhaltene Lösung unter Zusatz von °)°5 S käuflichem, kolloidalem Palladium mit Wasserstoff schüttelt. Nach Beendigung der Wasserstoffaufnahme wird das Palladium durch kurzes Erhitzen ausgeflockt uud die abfiltrierte Lösung mit Ammoniak übersättigt, wobei das Dihydrooxycodeinon ausfällt.b) The experiment proceeds in the same way if 10 g of oxycodeinone are suspended in water, mixed with 32 ecm normal acetic acid and the solution obtained is shaken with hydrogen with the addition of °) ° 5 S of commercially available colloidal palladium. After the uptake of hydrogen has ceased, the palladium is flocculated by brief heating and the filtered solution is supersaturated with ammonia, the dihydrooxycodeinone precipitating out.
c) 31,30 g Oxycodeinon (]/10 g Mol.) werden in 50 ecm Wasser suspendiert und mit 12 g Eisessig in Lösung gebracht. Dieser Lösung werden 0,05 g Palladiumchlorürc) 31.30 g of oxycodeinone ( ] / 10 g mol.) are suspended in 50 ecm of water and dissolved with 12 g of glacial acetic acid. 0.05 g of palladium chloride are added to this solution
(Pd Cl2 + 2 H2 O)(Pd Cl 2 + 2 H 2 O)
gelöst in 10 ecm Wasser zugefügt, die ganze Flüssigkeit mit Wasser auf 200 ecm aufgefüllt und im Wasserstoffstrom bis zur Sättigung geschüttelt. Nach Beendigung der Wasserstoffaufnahme wird vom ausgeflockten Palladium abfiltriert und die Lösung mit Ammoniak gefällt, wobei das Dihydrooxycodeinon quantitativ ausfällt.dissolved in 10 ecm of water added to the whole Liquid filled up with water to 200 ecm and in a hydrogen stream until saturation shaken. After the uptake of hydrogen has ended, the flocculated palladium is removed filtered off and the solution precipitated with ammonia, the dihydrooxycodeinone precipitating quantitatively.
d) 10 g Oxycodeinon werden mit einer Lösung von 20 g Natriuml^drosulfit in 60 ecm Wasser gekocht, wobei nach kurzer Zeit alles gelöst ist. Beim Übersättigen mit Soda oder Ammoniak fallen 6 g Dihydrooxycodeinon in kristallinischem Zustande aus.d) 10 g of oxycodeinone are mixed with a solution of 20 g of sodium sulfite in 60 ecm Boiled water, after which everything is dissolved after a short time. When oversaturating with soda or Ammonia precipitate 6 g of dihydrooxycodeinone in a crystalline state.
5 g Oxycodeinon werden in 50 ecm Eisessig gelöst und in die kochende· Lösung im Laufe von ι Stunde 5 g Zinkstaub eingetragen. Dann wird die Lösung filtriert, mit dem gleichen Volumen Wasser versetzt und so lange Alkali zugegeben, bis das entstandene Zinkhydroxyd im Alkaliüberschuß sich gelöst hat. Die alkalische Flüssigkeit wird mit Chloroform extrahiert. Nach dem Verdunsten des Lösungsmittels hinterbleibt das Hydrierungsprodukt als gelbliches öl, das beim Anreiben mit Alkohol kristallinisch wird. Aus einem Gemisch von Alkohol und Chloroform umkristallisiert, wurden prismatische Stäbchen vom F. 293 ° erhalten.5 g of oxycodeinone are dissolved in 50 ecm of glacial acetic acid and poured into the boiling solution of ι hour 5 g of zinc dust entered. Then the solution is filtered with the same Volume of water was added and alkali was added until the zinc hydroxide formed has dissolved in excess alkali. The alkaline liquid is extracted with chloroform. After the solvent has evaporated, the hydrogenation product remains as a yellowish oil that becomes crystalline when rubbed with alcohol. From a mixture Recrystallized from alcohol and chloroform, prismatic rods with a mp of 293 ° obtain.
Beispiel III.Example III.
10 g Oxycodeinon werden mit 30 g Stannochlorid und 70 g Salzsäure (vom spez Gew. 1,19) 3 Stunden lang unter Druck auf 100c erhitzt. Der Bombeninhalt wird dann mit Wasser in Lösung gebracht und mit so viel starker Alkalilauge versetzt, bis das ausgeschiedene Stannohydroxyd gelöst ist. Die alkalische Flüssigkeit wird dann mit Chloroform erschöpfend extrahiert und die Chloroformlösung verdunstet. Sie hinterläßt ein dickes, gelbes Öl, das beim Anreiben mit Salzsäure das Chlorhydrat der alkalilöslichen Hydrierungsbase liefert. Dieses Chlorhydrat kristallisiert aus Wasser in derben Säulen.10 g Oxycodeinon be with 30 g of stannous chloride and 70 g of hydrochloric acid (having a specific weight. 1.19) is heated for 3 hours under pressure to 100 c. The contents of the bomb are then dissolved with water and so much strong alkali is added until the precipitated stannous hydroxide is dissolved. The alkaline liquid is then exhaustively extracted with chloroform and the chloroform solution evaporated. It leaves a thick, yellow oil which, when rubbed with hydrochloric acid, supplies the hydrochloride of the alkali-soluble hydrogenation base. This chlorine hydrate crystallizes from water in coarse columns.
Claims (1)
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|---|---|
| DE296916C true DE296916C (en) |
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ID=551258
Family Applications (1)
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1730151A1 (en) * | 2004-03-30 | 2006-12-13 | Euro-Celtique S.A. | Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone |
| US8703950B2 (en) | 2010-07-02 | 2014-04-22 | Johnson Matthey Public Limited Co. | Low ABUK oxycodone, its salts and methods of making same |
-
0
- DE DENDAT296916D patent/DE296916C/de active Active
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8822687B2 (en) | 2004-03-30 | 2014-09-02 | Purdue Pharma L.P. | 8a,14-dihydroxy-7,8-dihydrocodeinone |
| US11384091B2 (en) | 2004-03-30 | 2022-07-12 | Purdue Pharma L.P. | Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone |
| EP1730151A1 (en) * | 2004-03-30 | 2006-12-13 | Euro-Celtique S.A. | Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone |
| US7674798B2 (en) | 2004-03-30 | 2010-03-09 | Purdue Pharma L.P. | Oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone |
| US7674800B2 (en) | 2004-03-30 | 2010-03-09 | Purdue Pharma L.P. | Oxycodone hydrochloride having less than 25 PPM 14-hydroxycodeinone |
| US7683072B2 (en) | 2004-03-30 | 2010-03-23 | Purdue Pharma L.P. | Oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone |
| AP2232A (en) * | 2004-03-30 | 2011-05-04 | Euro Celtique | Process for preparing oxycodone hydrochloride having less than 25ppm 14-hydroxycodeinone. |
| US9073933B2 (en) | 2004-03-30 | 2015-07-07 | Purdue Pharma L.P. | Oxycodone hydrochloride having less than 25 PPM 14-hydroxycodeinone |
| US7674799B2 (en) | 2004-03-30 | 2010-03-09 | Purdue Pharma L.P. | Oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone |
| EP1730151A4 (en) * | 2004-03-30 | 2007-05-23 | Euro Celtique Sa | Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone |
| US9522919B2 (en) | 2004-03-30 | 2016-12-20 | Purdue Pharma L.P. | Oxycodone compositions |
| EP2426132B1 (en) | 2004-03-30 | 2016-01-13 | Euro-Celtique S.A. | Process for preparing oxycodone hydrochloride compositions having less than 25ppm 14-hydroxycodeinone |
| US9777011B2 (en) | 2004-03-30 | 2017-10-03 | Purdue Pharma L.P. | Process for preparing oxycodone compositions |
| US10259819B2 (en) | 2004-03-30 | 2019-04-16 | Purdue Pharma L.P. | Process for preparing oxycodone compositions |
| US10407434B2 (en) | 2004-03-30 | 2019-09-10 | Purdue Pharma L.P. | Process for preparing oxycodone compositions |
| US10689389B2 (en) | 2004-03-30 | 2020-06-23 | Purdue Pharma L.P. | Process for preparing oxycodone compositions |
| US10696684B2 (en) | 2004-03-30 | 2020-06-30 | Purdue Pharma L.P. | Process for preparing oxycodone hydrochloride having less than 25 PPM 14-hydroxycodeinone |
| US11236098B2 (en) | 2004-03-30 | 2022-02-01 | Purdue Pharma L.P. | Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone |
| US8703950B2 (en) | 2010-07-02 | 2014-04-22 | Johnson Matthey Public Limited Co. | Low ABUK oxycodone, its salts and methods of making same |
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