JP2005523245A5 - - Google Patents
Download PDFInfo
- 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
- Authority
- 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
Links
- 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 (enExample) | 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 (enExample) |
| EP (1) | EP1456229B1 (enExample) |
| JP (1) | JP4510461B2 (enExample) |
| KR (1) | KR20040066167A (enExample) |
| CN (2) | CN100584859C (enExample) |
| AR (1) | AR037827A1 (enExample) |
| AT (1) | ATE441662T1 (enExample) |
| AU (1) | AU2002364991B9 (enExample) |
| BR (1) | BR0214937A (enExample) |
| CA (1) | CA2469918A1 (enExample) |
| CO (1) | CO5590934A2 (enExample) |
| CY (1) | CY1110694T1 (enExample) |
| DE (1) | DE60233589D1 (enExample) |
| DK (1) | DK1456229T3 (enExample) |
| EA (1) | EA007964B1 (enExample) |
| ES (1) | ES2333784T3 (enExample) |
| FR (1) | FR2833596B1 (enExample) |
| HU (1) | HUP0402602A3 (enExample) |
| IL (1) | IL162385A0 (enExample) |
| MX (1) | MXPA04005484A (enExample) |
| NO (1) | NO20042640L (enExample) |
| NZ (1) | NZ533864A (enExample) |
| PL (1) | PL371763A1 (enExample) |
| PT (1) | PT1456229E (enExample) |
| SI (1) | SI1456229T1 (enExample) |
| TW (1) | TWI322820B (enExample) |
| WO (1) | WO2003054001A2 (enExample) |
| ZA (1) | ZA200404631B (enExample) |
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 |
| 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 |
| 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 |
| WO2016056022A2 (en) * | 2014-10-07 | 2016-04-14 | Alaparthi Lakshmi Prasad | Intermediates and processes to prepare 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 |
| CN115785226A (zh) * | 2021-09-09 | 2023-03-14 | 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 |
| US5696270A (en) * | 1989-05-23 | 1997-12-09 | Abbott Laboratories | Intermediate for making retroviral protease inhibiting compounds |
| US5386009A (en) * | 1990-03-19 | 1995-01-31 | Merck & Co. Inc. | Lipopeptide derivatives |
| CZ288974B6 (cs) * | 1992-03-19 | 2001-10-17 | Eli Lilly And Company | Acylový derivát echinocandinu, způsob jeho přípravy, farmaceutický prostředek s jeho obsahem a jeho pouľití |
| SG75092A1 (en) * | 1993-08-09 | 2000-09-19 | Biomeasure Inc | 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 |
| EP0781141B1 (en) * | 1994-09-16 | 2002-09-04 | Merck & Co. Inc. | 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 |
| 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 |
| 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 |
| JP2003505468A (ja) * | 1999-07-27 | 2003-02-12 | アヴェンティス ファルマ ドイチェラント ゲーエムベーハー | 新規なシクロヘキサペプチド化合物、それらの製造方法及びそれらの医薬品としての使用 |
| 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 AU AU2002364991A patent/AU2002364991B9/en not_active Ceased
- 2002-12-12 AT AT02805374T patent/ATE441662T1/de active
- 2002-12-12 DK DK02805374T patent/DK1456229T3/da active
- 2002-12-12 NZ NZ533864A patent/NZ533864A/xx not_active IP Right Cessation
- 2002-12-12 PT PT02805374T patent/PT1456229E/pt unknown
- 2002-12-12 HU HU0402602A patent/HUP0402602A3/hu unknown
- 2002-12-12 EP EP02805374A patent/EP1456229B1/fr not_active Expired - Lifetime
- 2002-12-12 ES ES02805374T patent/ES2333784T3/es not_active Expired - Lifetime
- 2002-12-12 EA EA200400806A patent/EA007964B1/ru not_active IP Right Cessation
- 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 US US11/591,898 patent/US20070105760A1/en not_active Abandoned
- 2002-12-12 PL PL02371763A patent/PL371763A1/xx not_active Application Discontinuation
- 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 WO PCT/FR2002/004308 patent/WO2003054001A2/fr not_active Ceased
- 2002-12-12 MX MXPA04005484A patent/MXPA04005484A/es active IP Right Grant
- 2002-12-12 KR KR10-2004-7009121A patent/KR20040066167A/ko not_active Abandoned
- 2002-12-12 JP JP2003554717A patent/JP4510461B2/ja not_active Expired - Fee Related
- 2002-12-12 DE DE60233589T patent/DE60233589D1/de not_active Expired - Lifetime
- 2002-12-12 CN CNB2005101156130A patent/CN1326872C/zh not_active Expired - Fee Related
- 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7568510B2 (ja) | ペプチド化合物、またはアミド化合物の脱保護法および固相反応における脱樹脂方法、並びにペプチド化合物の製造方法 | |
| US12312379B2 (en) | Methods for producing cyclic compounds comprising N-substituted amino acid residues | |
| JP2004517090A5 (enExample) | ||
| JP2005523245A5 (enExample) | ||
| JP7430297B2 (ja) | Ｎ－アルキルアミノ酸、およびｎ－アルキルアミノ酸を含むペプチドの製造方法 | |
| KR20230125807A (ko) | 아미노산의 고상 합성용 수지에의 담지 방법 | |
| WO2013143497A1 (zh) | 一种高纯度环肽化合物及其制备方法和用途 | |
| JPH10512257A (ja) | 置換オキサゾリジンカルパインおよび／またはカテプシンｂ阻害剤 | |
| US20100273977A1 (en) | Process for the preparation of echinocandin derivatives | |
| TW202432170A (zh) | 相對於ｈｒａｓ及ｎｒａｓ具有選擇性之ｋｒａｓ抑制作用的環狀化合物 | |
| JPH11292840A (ja) | ノルスタチン誘導体又はその塩 | |
| Pratsch et al. | Radical arylation of tyrosine and its application in the synthesis of a highly selective neurotensin receptor 2 ligand | |
| CA2647163C (en) | Modified macrophage migration inhibitory factor inhibitors | |
| JPH08502250A (ja) | 成長ホルモン放出ペプチド | |
| US11634428B2 (en) | Deuterated angiotensin-converting enzyme-2 (ACE-2) inhibitors | |
| JPWO2003026645A1 (ja) | テトラペプチド誘導体の結晶 | |
| JP4493891B2 (ja) | エキノカンジンの新誘導体、それらの製造方法及びそれらの抗菌剤としての使用 | |
| JP2003505468A (ja) | 新規なシクロヘキサペプチド化合物、それらの製造方法及びそれらの医薬品としての使用 | |
| EA049862B1 (ru) | Способ получения циклического соединения, содержащего n-замещенный аминокислотный остаток | |
| AU2022269959A1 (en) | Methods for producing cyclic compounds comprising N-substituted amino acid residues | |
| KR20110073473A (ko) | 펩티드 화합물 및 그의 제조 방법 | |
| WO2012016362A1 (zh) | 用于治疗阿尔茨海默病的肽类β分泌酶抑制剂及其用途 | |
| CN1155884A (zh) | 作为细胞粘连抑制剂的(-)-(3r)-3-甲基-4-(4-(4-(4-吡啶基)哌嗪-1-基)苯氧基)丁酸 | |
| WO2014103481A1 (ja) | 環状ペプチド及びこれを含有する医薬 | |
| JP2008019214A (ja) | ペリンドプリルまたはその誘導体の製造方法 |