JP2005523245A5 - - Google Patents
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- Publication number
- JP2005523245A5 JP2005523245A5 JP2003554717A JP2003554717A JP2005523245A5 JP 2005523245 A5 JP2005523245 A5 JP 2005523245A5 JP 2003554717 A JP2003554717 A JP 2003554717A JP 2003554717 A JP2003554717 A JP 2003554717A JP 2005523245 A5 JP2005523245 A5 JP 2005523245A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
- reaction
- iii
- nabh
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 7
- 238000006268 reductive amination reaction Methods 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 238000005755 formation reaction Methods 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 14
- 239000002253 acid Substances 0.000 claims 7
- 238000006297 dehydration reaction Methods 0.000 claims 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 239000004473 Threonine Substances 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- FAUOJMHVEYMQQG-HVYQDZECSA-N echinocandin B Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@@H](C)O)=CC=C(O)C=C1 FAUOJMHVEYMQQG-HVYQDZECSA-N 0.000 claims 5
- 108010062092 echinocandin B Proteins 0.000 claims 5
- 229960003104 ornithine Drugs 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 229960001153 serine Drugs 0.000 claims 5
- 229960002898 threonine Drugs 0.000 claims 5
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000005917 acylation reaction Methods 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- 101100272976 Panax ginseng CYP716A53v2 gene Proteins 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims 1
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 claims 1
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 claims 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 claims 1
- MNZMECMQTYGSOI-UHFFFAOYSA-N acetic acid;hydron;bromide Chemical compound Br.CC(O)=O MNZMECMQTYGSOI-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000005576 amination reaction Methods 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 claims 1
- 239000003429 antifungal agent Substances 0.000 claims 1
- 229940121375 antifungal agent Drugs 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 claims 1
- 238000009938 salting Methods 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 C[C@]([C@@](C(N(C[C@@](C1)O)[C@@]1C(N[C@@]([C@@](Cc(cc1)ccc1O)O)C(N[C@@](CO)C(N(C[C@](C)[C@@]1O)[C@@]1C(NC(C(CC1=NC(*)=O)O)O)=O)=O)=O)=O)=O)NC1=O)O Chemical compound C[C@]([C@@](C(N(C[C@@](C1)O)[C@@]1C(N[C@@]([C@@](Cc(cc1)ccc1O)O)C(N[C@@](CO)C(N(C[C@](C)[C@@]1O)[C@@]1C(NC(C(CC1=NC(*)=O)O)O)=O)=O)=O)=O)=O)NC1=O)O 0.000 description 2
- 108010049047 Echinocandins Proteins 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0116230A FR2833596B1 (fr) | 2001-12-14 | 2001-12-14 | Procede de preparation de derives d'echinocandine |
| PCT/FR2002/004308 WO2003054001A2 (fr) | 2001-12-14 | 2002-12-12 | Procede de preparation de derives d'echinocandines et leurs compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005523245A JP2005523245A (ja) | 2005-08-04 |
| JP2005523245A5 true JP2005523245A5 (https=) | 2006-01-26 |
| JP4510461B2 JP4510461B2 (ja) | 2010-07-21 |
Family
ID=8870520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003554717A Expired - Fee Related JP4510461B2 (ja) | 2001-12-14 | 2002-12-12 | エキノカンジン誘導体の製造方法 |
Country Status (28)
| Country | Link |
|---|---|
| US (3) | US20070105760A1 (https=) |
| EP (1) | EP1456229B1 (https=) |
| JP (1) | JP4510461B2 (https=) |
| KR (1) | KR20040066167A (https=) |
| CN (2) | CN100584859C (https=) |
| AR (1) | AR037827A1 (https=) |
| AT (1) | ATE441662T1 (https=) |
| AU (1) | AU2002364991B9 (https=) |
| BR (1) | BR0214937A (https=) |
| CA (1) | CA2469918A1 (https=) |
| CO (1) | CO5590934A2 (https=) |
| CY (1) | CY1110694T1 (https=) |
| DE (1) | DE60233589D1 (https=) |
| DK (1) | DK1456229T3 (https=) |
| EA (1) | EA007964B1 (https=) |
| ES (1) | ES2333784T3 (https=) |
| FR (1) | FR2833596B1 (https=) |
| HU (1) | HUP0402602A3 (https=) |
| IL (1) | IL162385A0 (https=) |
| MX (1) | MXPA04005484A (https=) |
| NO (1) | NO20042640L (https=) |
| NZ (1) | NZ533864A (https=) |
| PL (1) | PL371763A1 (https=) |
| PT (1) | PT1456229E (https=) |
| SI (1) | SI1456229T1 (https=) |
| TW (1) | TWI322820B (https=) |
| WO (1) | WO2003054001A2 (https=) |
| ZA (1) | ZA200404631B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2833596B1 (fr) * | 2001-12-14 | 2005-02-18 | Aventis Pharma Sa | Procede de preparation de derives d'echinocandine |
| TW200826957A (en) * | 2006-10-16 | 2008-07-01 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Purification processes for echinocandin-type compounds |
| FR2921060B1 (fr) * | 2007-09-14 | 2012-06-15 | Novexel | Nouveau procede de preparation d'une piperidine disubsituee et nouveaux intermediaires |
| FR2936798B1 (fr) * | 2008-10-03 | 2012-09-28 | Novexel | Nouveaux composes heterocycliques azotes, leur preparation et leur utilisation comme medicaments antibacteriens. |
| FR2936951B1 (fr) * | 2008-10-10 | 2010-12-03 | Novexel | Nouvelles combinaisons de composes heterocycliques azotes antibacteriens avec d'autres composes antibacteriens et leur utilisation comme medicaments |
| FR2937034B1 (fr) * | 2008-10-10 | 2012-11-23 | Novexel | Nouveaux composes heterocycliques azotes, leur preparation et leur utilisation comme medicaments antibacteriens |
| CN101928670B (zh) | 2009-09-24 | 2012-02-22 | 上海天伟生物制药有限公司 | 一种抗生素的高产菌株及其制备方法和用途 |
| CN102627689B (zh) * | 2012-03-30 | 2014-08-06 | 上海天伟生物制药有限公司 | 一种环肽类化合物的水合物及其制备方法和用途 |
| CN102659930B (zh) * | 2012-03-30 | 2014-04-23 | 上海天伟生物制药有限公司 | 一种高纯度环肽类物质的晶体及其制备方法和用途 |
| CN102627688B (zh) * | 2012-03-30 | 2014-12-31 | 上海天伟生物制药有限公司 | 一种高纯度环肽化合物及其制备方法和用途 |
| EP3464319A4 (en) * | 2014-10-07 | 2020-02-26 | Alaparthi, Lakshmi Prasad | INTERMEDIATES AND PROCESSES FOR THE PREPARATION OF ANIDULAFUNGIN |
| CN112646854B (zh) * | 2020-12-11 | 2022-10-11 | 浙江工业大学 | 一种棘白菌素b合成培养基及应用 |
| CN115785226B (zh) * | 2021-09-09 | 2026-02-24 | 上海天伟生物制药有限公司 | 一种棘白菌素药物杂质及其制备、纯化方法和应用 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293484A (en) * | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | Derivatives of A-30912H nucleus |
| US5207710A (en) * | 1988-09-29 | 1993-05-04 | Collagen Corporation | Method for improving implant fixation |
| US5552558A (en) * | 1989-05-23 | 1996-09-03 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| US5386009A (en) * | 1990-03-19 | 1995-01-31 | Merck & Co. Inc. | Lipopeptide derivatives |
| MY136593A (en) * | 1992-03-19 | 2008-10-31 | Lilly Co Eli | Cyclic peptide antifungal agents and process for preparation thereof |
| EP0788509B1 (en) * | 1993-08-09 | 2003-05-28 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S. | Therapeutic peptide derivatives |
| JP3107691B2 (ja) * | 1993-12-03 | 2000-11-13 | 株式会社東芝 | 半導体記憶装置及びその製造方法 |
| AU692308B2 (en) * | 1994-09-16 | 1998-06-04 | Merck Sharp & Dohme Corp. | Aza cyclohexapeptide compounds |
| US5646111A (en) * | 1995-04-07 | 1997-07-08 | Eli Lilly And Company | Cyclic peptide antifungal Agents |
| US5652213A (en) * | 1995-05-26 | 1997-07-29 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| US5852213A (en) * | 1996-07-10 | 1998-12-22 | American Cyanamid Company | Mercaptoketones and mercaptoalcohols and a process for their preparation |
| US6207710B1 (en) * | 1996-11-22 | 2001-03-27 | Elan Pharmaceuticals, Inc. | Compounds for inhibiting β-amyloid peptide release and/or its synthesis |
| UA72200C2 (uk) * | 1997-12-10 | 2005-02-15 | Авентіс Фарма С.А. | Похідні ехінокандину, спосіб їх одержання, їх застосування, проміжні сполуки та фармацевтична композиція |
| FR2794747B1 (fr) * | 1999-06-09 | 2004-04-16 | Hoechst Marion Roussel Inc | Nouveaux derives de l'echinocandine, leur procede de preparation et leur application comme anti-fongiques |
| FR2794746B1 (fr) * | 1999-06-09 | 2002-12-06 | Hoechst Marion Roussel Inc | Nouveaux derives de l'echinocandine, leur procede de preparation et leur application comme anti-fongiques |
| AU6564000A (en) * | 1999-07-27 | 2001-02-13 | Aventis Pharma Deutschland Gmbh | Novel cyclohexapeptide compounds, processes for their production and their use as a pharmaceutical |
| FR2833596B1 (fr) * | 2001-12-14 | 2005-02-18 | Aventis Pharma Sa | Procede de preparation de derives d'echinocandine |
-
2001
- 2001-12-14 FR FR0116230A patent/FR2833596B1/fr not_active Expired - Fee Related
-
2002
- 2002-12-12 ES ES02805374T patent/ES2333784T3/es not_active Expired - Lifetime
- 2002-12-12 SI SI200230861T patent/SI1456229T1/sl unknown
- 2002-12-12 CN CN02824928A patent/CN100584859C/zh not_active Expired - Fee Related
- 2002-12-12 PT PT02805374T patent/PT1456229E/pt unknown
- 2002-12-12 CA CA002469918A patent/CA2469918A1/fr not_active Abandoned
- 2002-12-12 BR BR0214937-0A patent/BR0214937A/pt not_active Application Discontinuation
- 2002-12-12 KR KR10-2004-7009121A patent/KR20040066167A/ko not_active Abandoned
- 2002-12-12 DE DE60233589T patent/DE60233589D1/de not_active Expired - Lifetime
- 2002-12-12 EA EA200400806A patent/EA007964B1/ru not_active IP Right Cessation
- 2002-12-12 DK DK02805374T patent/DK1456229T3/da active
- 2002-12-12 HU HU0402602A patent/HUP0402602A3/hu unknown
- 2002-12-12 MX MXPA04005484A patent/MXPA04005484A/es active IP Right Grant
- 2002-12-12 JP JP2003554717A patent/JP4510461B2/ja not_active Expired - Fee Related
- 2002-12-12 WO PCT/FR2002/004308 patent/WO2003054001A2/fr not_active Ceased
- 2002-12-12 US US11/591,898 patent/US20070105760A1/en not_active Abandoned
- 2002-12-12 CN CNB2005101156130A patent/CN1326872C/zh not_active Expired - Fee Related
- 2002-12-12 PL PL02371763A patent/PL371763A1/xx not_active Application Discontinuation
- 2002-12-12 NZ NZ533864A patent/NZ533864A/xx not_active IP Right Cessation
- 2002-12-12 AT AT02805374T patent/ATE441662T1/de active
- 2002-12-12 EP EP02805374A patent/EP1456229B1/fr not_active Expired - Lifetime
- 2002-12-12 AU AU2002364991A patent/AU2002364991B9/en not_active Ceased
- 2002-12-13 TW TW091136168A patent/TWI322820B/zh not_active IP Right Cessation
- 2002-12-13 AR ARP020104846A patent/AR037827A1/es active IP Right Grant
- 2002-12-24 IL IL16238502A patent/IL162385A0/xx unknown
-
2004
- 2004-06-10 ZA ZA200404631A patent/ZA200404631B/en unknown
- 2004-06-11 CO CO04055277A patent/CO5590934A2/es not_active Application Discontinuation
- 2004-06-14 US US10/867,070 patent/US7148322B2/en not_active Expired - Fee Related
- 2004-06-23 NO NO20042640A patent/NO20042640L/no not_active Application Discontinuation
-
2009
- 2009-12-01 CY CY20091101267T patent/CY1110694T1/el unknown
-
2010
- 2010-07-06 US US12/830,941 patent/US20100273977A1/en not_active Abandoned
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