JP2007509945A5 - - Google Patents
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- Publication number
- JP2007509945A5 JP2007509945A5 JP2006538157A JP2006538157A JP2007509945A5 JP 2007509945 A5 JP2007509945 A5 JP 2007509945A5 JP 2006538157 A JP2006538157 A JP 2006538157A JP 2006538157 A JP2006538157 A JP 2006538157A JP 2007509945 A5 JP2007509945 A5 JP 2007509945A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- fentanyl
- range
- alkyl
- group
- 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- Withdrawn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
- 238000000034 method Methods 0.000 claims description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 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 11
- 229960002428 fentanyl Drugs 0.000 claims 10
- -1 aryl silanes Chemical class 0.000 claims 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 239000007864 aqueous solution Substances 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000004587 chromatography analysis Methods 0.000 claims 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 2
- 230000005526 G1 to G0 transition Effects 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- 239000003929 acidic solution Substances 0.000 claims 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 229910017604 nitric acid Inorganic materials 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 238000012856 packing Methods 0.000 claims 2
- 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 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001343 alkyl silanes Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 150000007860 aryl ester derivatives Chemical class 0.000 claims 1
- 150000008378 aryl ethers Chemical class 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- QTLFDCJYRAHUCF-UHFFFAOYSA-N methoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[SiH2]CCOCC1CO1 QTLFDCJYRAHUCF-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- FPLYNRPOIZEADP-UHFFFAOYSA-N octylsilane Chemical compound CCCCCCCC[SiH3] FPLYNRPOIZEADP-UHFFFAOYSA-N 0.000 claims 1
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims 1
- 238000004262 preparative liquid chromatography Methods 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 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 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
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 JP2007509945A (ja) | 2007-04-19 |
| JP2007509945A5 true 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
-
2006
- 2006-04-27 MX MXPA06004711 patent/MX264489B/es active IP Right Grant
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