JP2011524376A - Ｎ−脱メチル化モルフィナン化合物を合成する方法 - Google Patents
Ｎ−脱メチル化モルフィナン化合物を合成する方法 Download PDFInfo
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- JP2011524376A JP2011524376A JP2011513822A JP2011513822A JP2011524376A JP 2011524376 A JP2011524376 A JP 2011524376A JP 2011513822 A JP2011513822 A JP 2011513822A JP 2011513822 A JP2011513822 A JP 2011513822A JP 2011524376 A JP2011524376 A JP 2011524376A
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- mol
- reducing agent
- reaction
- protected form
- methylmorphinan
- Prior art date
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- Pending
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- 238000000034 method Methods 0.000 title claims abstract description 91
- INAXVFBXDYWQFN-XHSDSOJGSA-N morphinan Chemical class C1C2=CC=CC=C2[C@]23CCCC[C@H]3[C@@H]1NCC2 INAXVFBXDYWQFN-XHSDSOJGSA-N 0.000 title description 13
- 230000002194 synthesizing effect Effects 0.000 title 1
- IHBSVVZENGBQDY-BBWFWOEESA-N N-Methyl morphinan Chemical compound C1C2=CC=CC=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 IHBSVVZENGBQDY-BBWFWOEESA-N 0.000 claims abstract description 51
- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 claims abstract description 20
- 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 abstract description 20
- 229930003945 thebaine Natural products 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 241000218180 Papaveraceae Species 0.000 claims abstract description 7
- 241000196324 Embryophyta Species 0.000 claims abstract description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 68
- 238000006722 reduction reaction Methods 0.000 claims description 40
- 239000003446 ligand Substances 0.000 claims description 36
- 239000007787 solid Substances 0.000 claims description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 32
- 239000011541 reaction mixture Substances 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 25
- ULDHWYNVMJKACM-KTGAGVNESA-N (1R,9R,10R)-17-methyl-17-oxido-17-azoniatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6-triene Chemical compound C1CCC[C@H]2[C@]3([H])[N+]([O-])(C)CC[C@@]21C1=CC=CC=C1C3 ULDHWYNVMJKACM-KTGAGVNESA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 17
- 229910021645 metal ion Inorganic materials 0.000 claims description 16
- 239000007800 oxidant agent Substances 0.000 claims description 14
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- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 9
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- ZKLXUUYLEHCAMF-UUWFMWQGSA-N Oripavine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 ZKLXUUYLEHCAMF-UUWFMWQGSA-N 0.000 claims description 8
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- 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 claims description 8
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- 229960005181 morphine Drugs 0.000 claims description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229960004126 codeine Drugs 0.000 claims description 4
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 229960002069 diamorphine Drugs 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
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- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 150000003983 crown ethers Chemical class 0.000 claims description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- OUDSFQBUEBFSPS-UHFFFAOYSA-N ethylenediaminetriacetic acid Chemical compound OC(=O)CNCCN(CC(O)=O)CC(O)=O OUDSFQBUEBFSPS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000004032 porphyrins Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- LYNARWYQOUZXDY-UHFFFAOYSA-N corrole Chemical compound N1C(C=C2NC(=CC=3NC4=CC=3)C=C2)=CC=C1C=C1C=CC4=N1 LYNARWYQOUZXDY-UHFFFAOYSA-N 0.000 claims 1
- 229960000935 dehydrated alcohol Drugs 0.000 claims 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 claims 1
- 238000010520 demethylation reaction Methods 0.000 abstract description 14
- 238000006243 chemical reaction Methods 0.000 description 54
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 16
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 229910052742 iron Inorganic materials 0.000 description 12
- -1 morphinan N-oxide Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 11
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- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 4
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- RIKMCJUNPCRFMW-ISWURRPUSA-N Noroxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4 RIKMCJUNPCRFMW-ISWURRPUSA-N 0.000 description 1
- 208000012488 Opiate Overdose Diseases 0.000 description 1
- 229940123257 Opioid receptor antagonist Drugs 0.000 description 1
- 208000026251 Opioid-Related disease Diseases 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone 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 description 1
- 235000008753 Papaver somniferum Nutrition 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- PRQBVMJJJKVPLX-UHFFFAOYSA-N [Fe+2].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Fe+2].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 PRQBVMJJJKVPLX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004974 alkaline earth metal peroxides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003622 immobilized catalyst Substances 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
- 229960004127 naloxone Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QKQQEIVDLRUZRP-UHFFFAOYSA-N northebaine Natural products COC1=CC=C2C(NCC3)CC4=CC=C(OC)C5=C4C23C1O5 QKQQEIVDLRUZRP-UHFFFAOYSA-N 0.000 description 1
- 239000003401 opiate antagonist Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 229940124636 opioid drug Drugs 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229960002085 oxycodone Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005945 von Braun degradation reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/28—Morphinans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2008903154A AU2008903154A0 (en) | 2008-06-20 | Process | |
| AU2008903154 | 2008-06-20 | ||
| PCT/AU2009/000786 WO2009152577A1 (en) | 2008-06-20 | 2009-06-19 | Process for the synthesis of n-demethylated morphinane compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011524376A true JP2011524376A (ja) | 2011-09-01 |
| JP2011524376A5 JP2011524376A5 (https=) | 2012-08-02 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2011513822A Pending JP2011524376A (ja) | 2008-06-20 | 2009-06-19 | Ｎ−脱メチル化モルフィナン化合物を合成する方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20110306766A1 (https=) |
| EP (1) | EP2297160B1 (https=) |
| JP (1) | JP2011524376A (https=) |
| CN (1) | CN102089310A (https=) |
| AU (1) | AU2009260121C1 (https=) |
| CA (1) | CA2727944A1 (https=) |
| NZ (1) | NZ589867A (https=) |
| WO (1) | WO2009152577A1 (https=) |
| ZA (1) | ZA201009078B (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8829020B2 (en) | 2009-07-16 | 2014-09-09 | Mallinckrodt Llc | Compounds and compositions for use in phototherapy and in treatment of ocular neovascular disease and cancers |
| CN103275005B (zh) * | 2013-06-17 | 2015-05-20 | 苏州立新制药有限公司 | ent-3-甲氧基-17-甲基吗喃-10-酮的制备方法 |
| WO2017184979A1 (en) * | 2016-04-22 | 2017-10-26 | Noramco, Inc. | N-demethylation of morphinan alkaloids |
| US20230242547A1 (en) * | 2020-06-10 | 2023-08-03 | Research Center Pharmaceutical Engineering Gmbh | Processes for preparing nor-opioid compounds and opioid antagonists by electrochemical n-demethylation |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0471646A (ja) * | 1990-07-10 | 1992-03-06 | Agency Of Ind Science & Technol | 固定化金属錯体 |
| JPH05115787A (ja) * | 1991-10-30 | 1993-05-14 | Tosoh Corp | アスコルビン酸の酸化触媒物質 |
| JP2002363188A (ja) * | 2001-05-31 | 2002-12-18 | Osaka Gas Co Ltd | 担体−錯体複合体、アルカン酸化触媒およびアルカノール合成方法 |
| JP2004537584A (ja) * | 2001-08-06 | 2004-12-16 | ビーピー ケミカルズ リミテッド | 連鎖生長反応方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPQ968300A0 (en) * | 2000-08-25 | 2000-09-21 | Glaxo Wellcome Australia Ltd | Chemical methods |
| CA2539659C (en) * | 2003-09-22 | 2013-03-26 | Johnson Matthey Public Limited Company | Process for the synthesis of morphinane compounds and intermediates thereof |
| CN1785976A (zh) * | 2005-12-15 | 2006-06-14 | 南京大学 | 一类n－烃基青藤碱及其制备方法 |
-
2009
- 2009-06-19 JP JP2011513822A patent/JP2011524376A/ja active Pending
- 2009-06-19 CN CN2009801232499A patent/CN102089310A/zh active Pending
- 2009-06-19 WO PCT/AU2009/000786 patent/WO2009152577A1/en not_active Ceased
- 2009-06-19 EP EP09765266.3A patent/EP2297160B1/en not_active Not-in-force
- 2009-06-19 AU AU2009260121A patent/AU2009260121C1/en not_active Ceased
- 2009-06-19 CA CA2727944A patent/CA2727944A1/en not_active Abandoned
- 2009-06-19 US US12/999,007 patent/US20110306766A1/en not_active Abandoned
- 2009-06-19 NZ NZ589867A patent/NZ589867A/xx unknown
-
2010
- 2010-12-17 ZA ZA2010/09078A patent/ZA201009078B/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0471646A (ja) * | 1990-07-10 | 1992-03-06 | Agency Of Ind Science & Technol | 固定化金属錯体 |
| JPH05115787A (ja) * | 1991-10-30 | 1993-05-14 | Tosoh Corp | アスコルビン酸の酸化触媒物質 |
| JP2002363188A (ja) * | 2001-05-31 | 2002-12-18 | Osaka Gas Co Ltd | 担体−錯体複合体、アルカン酸化触媒およびアルカノール合成方法 |
| JP2004537584A (ja) * | 2001-08-06 | 2004-12-16 | ビーピー ケミカルズ リミテッド | 連鎖生長反応方法 |
Non-Patent Citations (3)
| Title |
|---|
| JPN6013056625; Ｊｏｕｒｎａｌ ｏｆ Ｏｒｇａｎｉｃ Ｃｈｅｍｉｓｔｒｙ Ｖｏｌ．７２， Ｎｏ．２６, 2007, ｐｐ．９８８１-９８８５ * |
| JPN6013056626; Ｂｉｏｏｒｇａｎｉｃ ＆ Ｍｅｄｉｃｉｎａｌ Ｃｈｅｍｉｓｔｒｙ Ｌｅｔｔｅｒｓ Ｖｏｌ．１６， Ｎｏ．１１, 2006, ｐｐ．２８６８-２８７１ * |
| JPN6013056628; Ｏｒｇａｎｉｃ Ｌｅｔｔｅｒｓ Ｖｏｌ．６， Ｎｏ．４, 2004, ｐｐ．５４１-５４４ * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2009260121B2 (en) | 2014-07-17 |
| CA2727944A1 (en) | 2009-12-23 |
| ZA201009078B (en) | 2012-02-29 |
| EP2297160A4 (en) | 2012-09-12 |
| EP2297160B1 (en) | 2014-09-24 |
| CN102089310A (zh) | 2011-06-08 |
| US20110306766A1 (en) | 2011-12-15 |
| WO2009152577A1 (en) | 2009-12-23 |
| NZ589867A (en) | 2012-08-31 |
| AU2009260121A1 (en) | 2009-12-23 |
| EP2297160A1 (en) | 2011-03-23 |
| AU2009260121C1 (en) | 2014-12-18 |
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