DE296916C - - Google Patents
Info
- 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.)
- Active
Links
- 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)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE296916C true DE296916C (el) |
Family
ID=551258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT296916D Active DE296916C (el) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE296916C (el) |
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 (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2426132B1 (en) | 2004-03-30 | 2016-01-13 | Euro-Celtique S.A. | Process for preparing oxycodone hydrochloride compositions having less than 25ppm 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 |
| US7674800B2 (en) | 2004-03-30 | 2010-03-09 | Purdue Pharma L.P. | 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 |
| US7674799B2 (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. |
| EP1730151A1 (en) * | 2004-03-30 | 2006-12-13 | Euro-Celtique S.A. | Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone |
| US12060361B2 (en) | 2004-03-30 | 2024-08-13 | Purdue Pharma L.P. | Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone |
| EP1730151A4 (en) * | 2004-03-30 | 2007-05-23 | Euro Celtique Sa | PROCESS FOR PREPARING OXYCODON HYDROCHLORIDE WITH LESS THAN 25 PPM 14-HYDROXYCODEINONE |
| US8822687B2 (en) | 2004-03-30 | 2014-09-02 | Purdue Pharma L.P. | 8a,14-dihydroxy-7,8-dihydrocodeinone |
| US9522919B2 (en) | 2004-03-30 | 2016-12-20 | Purdue Pharma L.P. | Oxycodone compositions |
| 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 |
| US9073933B2 (en) | 2004-03-30 | 2015-07-07 | Purdue Pharma L.P. | Oxycodone hydrochloride having less than 25 PPM 14-hydroxycodeinone |
| US11384091B2 (en) | 2004-03-30 | 2022-07-12 | 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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