TWI708779B - β-轉角擬肽環狀鹽之液相合成及結晶 - Google Patents
β-轉角擬肽環狀鹽之液相合成及結晶 Download PDFInfo
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- TWI708779B TWI708779B TW105121814A TW105121814A TWI708779B TW I708779 B TWI708779 B TW I708779B TW 105121814 A TW105121814 A TW 105121814A TW 105121814 A TW105121814 A TW 105121814A TW I708779 B TWI708779 B TW I708779B
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- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 238000001907 polarising light microscopy Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UIDUKLCLJMXFEO-UHFFFAOYSA-N propylsilane Chemical compound CCC[SiH3] UIDUKLCLJMXFEO-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Substances [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 229940094989 trimethylsilane Drugs 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1027—Tetrapeptides containing heteroatoms different from O, S, or N
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/30—Extraction; Separation; Purification by precipitation
- C07K1/306—Extraction; Separation; Purification by precipitation by crystallization
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1021—Tetrapeptides with the first amino acid being acidic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| US201562190596P | 2015-07-09 | 2015-07-09 | |
| US62/190,596 | 2015-07-09 |
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| KR102056257B1 (ko) * | 2015-07-09 | 2019-12-16 | 미메토젠 파르마슈티칼스 인크. | 베타-턴 펩티도미메틱 사이클릭 염의 용액상 합성 및 결정화 |
| SI3464336T1 (sl) | 2016-06-01 | 2022-06-30 | Athira Pharma, Inc. | Spojine |
| KR102826649B1 (ko) * | 2018-05-31 | 2025-06-30 | 쎄데르마 | 용액-상 펩티드의 합성 방법 및 그에 따른 보호 전략 |
| US11427612B2 (en) * | 2018-08-21 | 2022-08-30 | Wayne State University | Epimerization-free N to C solid-phase peptide synthesis |
| CN117279928A (zh) * | 2021-05-07 | 2023-12-22 | 中外制药株式会社 | 包含n-取代氨基酸残基的环状化合物的制备方法 |
Citations (3)
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| WO2001052843A1 (en) | 2000-01-18 | 2001-07-26 | Mcgill University | β-TURN PEPTIDOMIMETIC CYCLIC COMPOUNDS |
| WO2009123761A1 (en) * | 2008-04-04 | 2009-10-08 | Mimetogen Pharmaceuticals Inc. | Beta-turn peptidomimetic cyclic compounds for treating dry eye |
| WO2013191926A1 (en) * | 2012-06-22 | 2013-12-27 | Mimetogen Pharmaceuticals, Inc. | Synthesis of beta-turn peptidomimetic cyclic compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPP254898A0 (en) * | 1998-03-24 | 1998-04-23 | University Of Queensland, The | Peptide turn mimetics |
| HRP20041179B1 (hr) * | 2002-06-11 | 2012-11-30 | Eli Lilly And Company | Prekursorski oblici lijekova za aminokiseline s pobuđivačkom aktivnosti |
| AU2010217889B2 (en) * | 2009-02-27 | 2014-12-18 | Mimetogen Pharmaceuticals Inc. | Peptidomimetic cyclic compounds for treating retinitis pigmentosa |
| EP2598604B1 (de) * | 2010-07-29 | 2015-11-25 | Merck Patent GmbH | Flüssigkristallines medium enthaltend thiophenderivate |
| JP5710436B2 (ja) * | 2011-09-26 | 2015-04-30 | 株式会社東芝 | パターン形成方法 |
| JP6516974B2 (ja) * | 2013-06-14 | 2019-05-22 | 豊田合成株式会社 | ゴム組成物及びゴム製品 |
| CN105142777B (zh) * | 2013-06-20 | 2017-12-26 | 埃克森美孚化学专利公司 | 长桥Salen催化剂 |
| KR102056257B1 (ko) * | 2015-07-09 | 2019-12-16 | 미메토젠 파르마슈티칼스 인크. | 베타-턴 펩티도미메틱 사이클릭 염의 용액상 합성 및 결정화 |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001052843A1 (en) | 2000-01-18 | 2001-07-26 | Mcgill University | β-TURN PEPTIDOMIMETIC CYCLIC COMPOUNDS |
| WO2009123761A1 (en) * | 2008-04-04 | 2009-10-08 | Mimetogen Pharmaceuticals Inc. | Beta-turn peptidomimetic cyclic compounds for treating dry eye |
| WO2013191926A1 (en) * | 2012-06-22 | 2013-12-27 | Mimetogen Pharmaceuticals, Inc. | Synthesis of beta-turn peptidomimetic cyclic compounds |
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| CN114874288A (zh) | 2022-08-09 |
| WO2017005902A1 (en) | 2017-01-12 |
| JP6801835B2 (ja) | 2020-12-16 |
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| AU2016290654A1 (en) | 2018-01-25 |
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| EP4549450A2 (en) | 2025-05-07 |
| US20230357318A1 (en) | 2023-11-09 |
| US12281179B2 (en) | 2025-04-22 |
| CN107849089B (zh) | 2022-07-05 |
| AU2016290654C1 (en) | 2021-11-11 |
| US20170008923A1 (en) | 2017-01-12 |
| KR20180036982A (ko) | 2018-04-10 |
| US11078234B2 (en) | 2021-08-03 |
| TW201716425A (zh) | 2017-05-16 |
| AU2016290654B2 (en) | 2021-07-08 |
| CN107849089A (zh) | 2018-03-27 |
| US11753441B2 (en) | 2023-09-12 |
| HK1255355A1 (en) | 2019-08-16 |
| KR102056257B1 (ko) | 2019-12-16 |
| CA2991661A1 (en) | 2017-01-12 |
| EP3319978A1 (en) | 2018-05-16 |
| EP4549450A3 (en) | 2025-07-02 |
| US20190194251A1 (en) | 2019-06-27 |
| US20210300966A1 (en) | 2021-09-30 |
| US10125165B2 (en) | 2018-11-13 |
| EP3319978B1 (en) | 2025-02-19 |
| JP2018528928A (ja) | 2018-10-04 |
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