JP2007509945A - 逆相分取クロマトグラフィーによるフェンタニルの分離および精製のための産業用の方法 - Google Patents
逆相分取クロマトグラフィーによるフェンタニルの分離および精製のための産業用の方法 Download PDFInfo
- Publication number
- JP2007509945A JP2007509945A JP2006538157A JP2006538157A JP2007509945A JP 2007509945 A JP2007509945 A JP 2007509945A JP 2006538157 A JP2006538157 A JP 2006538157A JP 2006538157 A JP2006538157 A JP 2006538157A JP 2007509945 A JP2007509945 A JP 2007509945A
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- JP
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- Prior art keywords
- acid
- fentanyl
- column
- range
- alkyl
- 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.)
- Withdrawn
Links
- 229960002428 fentanyl Drugs 0.000 title claims abstract description 63
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000004237 preparative chromatography Methods 0.000 title abstract description 19
- 238000000746 purification Methods 0.000 title abstract description 8
- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000000926 separation method Methods 0.000 title description 12
- 238000000034 method Methods 0.000 claims abstract description 56
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 45
- 230000005526 G1 to G0 transition Effects 0.000 claims abstract description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract 6
- IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 claims description 62
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- -1 aryl silanes Chemical class 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 238000004587 chromatography analysis Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000011068 loading method Methods 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000012856 packing Methods 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001343 alkyl silanes Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 claims description 2
- 150000008378 aryl ethers Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- QTLFDCJYRAHUCF-UHFFFAOYSA-N methoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[SiH2]CCOCC1CO1 QTLFDCJYRAHUCF-UHFFFAOYSA-N 0.000 claims description 2
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 2
- 238000004262 preparative liquid chromatography Methods 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- FPLYNRPOIZEADP-UHFFFAOYSA-N octylsilane Chemical compound CCCCCCCC[SiH3] FPLYNRPOIZEADP-UHFFFAOYSA-N 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- 239000013110 organic ligand Substances 0.000 abstract 1
- 239000012535 impurity Substances 0.000 description 17
- 238000001556 precipitation Methods 0.000 description 10
- 229930013930 alkaloid Natural products 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 150000003797 alkaloid derivatives Chemical class 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 239000012527 feed solution Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000003306 harvesting Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 238000012435 analytical chromatography Methods 0.000 description 3
- 239000012296 anti-solvent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 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 description 2
- 239000002872 contrast media Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000003690 nonionic contrast media Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- 239000013598 vector Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 229940039231 contrast media Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 229960004379 fentanyl hydrochloride Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- POUMFISTNHIPTI-BOMBIWCESA-N hydron;(2s,4r)-n-[(1r,2r)-2-hydroxy-1-[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide;chloride Chemical compound Cl.CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 POUMFISTNHIPTI-BOMBIWCESA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229960001595 lincomycin hydrochloride Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- DUGOZIWVEXMGBE-STQMWFEESA-N methyl (S)-phenyl[(S)-piperidin-2-yl]acetate Chemical compound C([C@H]1[C@@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 DUGOZIWVEXMGBE-STQMWFEESA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- LHCBOXPPRUIAQT-UHFFFAOYSA-N n-phenyl-n-[1-(2-phenylethyl)piperidin-4-yl]propanamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 LHCBOXPPRUIAQT-UHFFFAOYSA-N 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 239000004084 narcotic analgesic agent Substances 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000003186 pharmaceutical solution Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000010567 reverse phase preparative liquid chromatography Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011856 silicon-based particle Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/32—Bonded phase chromatography
- B01D15/325—Reversed phase
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
- B01J20/287—Non-polar phases; Reversed phases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Hydrogenated Pyridines (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51527403P | 2003-10-29 | 2003-10-29 | |
| PCT/US2004/035386 WO2005044798A1 (en) | 2003-10-29 | 2004-10-22 | Industrial method for separation and purification of fentanyl by reverse phase preparative chromatography |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007509945A true JP2007509945A (ja) | 2007-04-19 |
| JP2007509945A5 JP2007509945A5 (enExample) | 2007-12-06 |
Family
ID=34572823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006538157A Withdrawn JP2007509945A (ja) | 2003-10-29 | 2004-10-22 | 逆相分取クロマトグラフィーによるフェンタニルの分離および精製のための産業用の方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7728145B2 (enExample) |
| EP (1) | EP1682505B1 (enExample) |
| JP (1) | JP2007509945A (enExample) |
| CN (1) | CN100509785C (enExample) |
| AT (1) | ATE418544T1 (enExample) |
| AU (1) | AU2004287815B2 (enExample) |
| CA (1) | CA2544195A1 (enExample) |
| DE (1) | DE602004018674D1 (enExample) |
| ES (1) | ES2320136T3 (enExample) |
| MX (1) | MX264489B (enExample) |
| WO (1) | WO2005044798A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7486949B2 (en) * | 2004-03-10 | 2009-02-03 | Broadcom Corporation | Method for re-establishing telephone calls after unintended termination |
| WO2006055321A2 (en) * | 2004-11-10 | 2006-05-26 | Boehringer Ingelheim Chemicals, Inc. | Process of making fentanyl intermediates |
| US20100076198A1 (en) * | 2008-09-19 | 2010-03-25 | Mallinckrodt Inc. | Crystalline forms of Fentanyl Alkaloid |
| CA2899387C (en) * | 2013-01-29 | 2018-07-17 | Neuland Health Sciences Private Limited | Purification of organic compounds using surrogate stationary phases on reversed phase columns |
| US20160237112A1 (en) * | 2013-09-20 | 2016-08-18 | Davuluri, Ramamohan Rao | Purification of organic compounds by surfactant mediated preparative hplc |
| US20220395767A1 (en) * | 2021-06-15 | 2022-12-15 | Perkinelmer Health Sciences, Inc. | Enhancing lcms analyte signals |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE623427A (enExample) * | 1961-10-10 | |||
| US4234684A (en) * | 1979-12-11 | 1980-11-18 | Eli Lilly And Company | Method of preparing mycophenolic acid glucoside |
| US4293489A (en) * | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | Derivatives of A-30912A nucleus |
| US4317903A (en) * | 1981-01-26 | 1982-03-02 | The Upjohn Company | Process for the purification of lincomycin |
| US4336333A (en) * | 1981-03-13 | 1982-06-22 | Eli Lilly And Company | Process for preparing tunicamycin |
| US4916142A (en) * | 1987-02-02 | 1990-04-10 | Boc, Inc. | N-heterocyclic-N-(4-piperidinyl)amides and pharmaceutical compositions and their use as analgesics |
| US4904590A (en) * | 1988-12-27 | 1990-02-27 | Eli Lilly And Company | Antibiotic A80915 and process for its production |
| US5780589A (en) * | 1994-11-30 | 1998-07-14 | The United States Of America As Represented By The Department Of Health And Human Services | Ultraselective opioidmimetic peptides and pharmacological and therapeutic uses thereof |
| JP2002502031A (ja) * | 1998-02-03 | 2002-01-22 | アークル， インコーポレイテッド | 逆相高速液体クロマトグラフィーを使用して小分子を分離する迅速方法 |
| CA2393559C (en) * | 1999-12-06 | 2009-05-26 | Mallinckrodt Inc. | Methods for the syntheses of alfentanil, sufentanil and remifentanil |
| ES2312798T3 (es) * | 2002-02-28 | 2009-03-01 | Mallinckrodt Inc. | Metodo y sistema para la separacion y purificacion de al menos un alcaloide narcotico usando cromatografia preparativa de fase inversa. |
| ITRM20020458A1 (it) | 2002-09-13 | 2004-03-14 | Ambiotec S A S Di Ammendola Sergio | Procedimento per la separazione preparativa degli epimeri di steroidi. |
-
2004
- 2004-10-22 JP JP2006538157A patent/JP2007509945A/ja not_active Withdrawn
- 2004-10-22 ES ES04796374T patent/ES2320136T3/es not_active Expired - Lifetime
- 2004-10-22 CA CA002544195A patent/CA2544195A1/en not_active Abandoned
- 2004-10-22 AT AT04796374T patent/ATE418544T1/de not_active IP Right Cessation
- 2004-10-22 US US10/574,545 patent/US7728145B2/en not_active Expired - Fee Related
- 2004-10-22 WO PCT/US2004/035386 patent/WO2005044798A1/en not_active Ceased
- 2004-10-22 EP EP04796374A patent/EP1682505B1/en not_active Expired - Lifetime
- 2004-10-22 AU AU2004287815A patent/AU2004287815B2/en not_active Expired - Fee Related
- 2004-10-22 DE DE602004018674T patent/DE602004018674D1/de not_active Expired - Fee Related
- 2004-10-22 CN CNB2004800321721A patent/CN100509785C/zh not_active Expired - Fee Related
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2006
- 2006-04-27 MX MXPA06004711 patent/MX264489B/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA06004711A (es) | 2006-07-20 |
| US7728145B2 (en) | 2010-06-01 |
| MX264489B (en) | 2009-02-12 |
| ATE418544T1 (de) | 2009-01-15 |
| CA2544195A1 (en) | 2005-05-19 |
| CN1874999A (zh) | 2006-12-06 |
| DE602004018674D1 (de) | 2009-02-05 |
| US20070123710A1 (en) | 2007-05-31 |
| EP1682505B1 (en) | 2008-12-24 |
| ES2320136T3 (es) | 2009-05-19 |
| AU2004287815A1 (en) | 2005-05-19 |
| WO2005044798A1 (en) | 2005-05-19 |
| CN100509785C (zh) | 2009-07-08 |
| EP1682505A1 (en) | 2006-07-26 |
| AU2004287815B2 (en) | 2009-05-28 |
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