JP2017524731A5 - - Google Patents
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- JP2017524731A5 JP2017524731A5 JP2017516642A JP2017516642A JP2017524731A5 JP 2017524731 A5 JP2017524731 A5 JP 2017524731A5 JP 2017516642 A JP2017516642 A JP 2017516642A JP 2017516642 A JP2017516642 A JP 2017516642A JP 2017524731 A5 JP2017524731 A5 JP 2017524731A5
- Authority
- JP
- Japan
- Prior art keywords
- peptide
- seq
- oso
- hydrolysis
- ethylene glycol
- 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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- 108090000765 processed proteins & peptides Proteins 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 102000004196 processed proteins & peptides Human genes 0.000 description 5
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 102000001301 EGF receptor Human genes 0.000 description 2
- 108060006698 EGF receptor Proteins 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 108010004034 stable plasma protein solution Proteins 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- BXRLWGXPSRYJDZ-UHFFFAOYSA-N 3-cyanoalanine Chemical compound OC(=O)C(N)CC#N BXRLWGXPSRYJDZ-UHFFFAOYSA-N 0.000 description 1
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 102400000059 Arg-vasopressin Human genes 0.000 description 1
- 101800001144 Arg-vasopressin Proteins 0.000 description 1
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 description 1
- 102100032957 C5a anaphylatoxin chemotactic receptor 1 Human genes 0.000 description 1
- 101710098483 C5a anaphylatoxin chemotactic receptor 1 Proteins 0.000 description 1
- 102000001902 CC Chemokines Human genes 0.000 description 1
- 108010040471 CC Chemokines Proteins 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- DGYHPLMPMRKMPD-UHFFFAOYSA-N L-propargyl glycine Natural products OC(=O)C(N)CC#C DGYHPLMPMRKMPD-UHFFFAOYSA-N 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000002072 Non-Receptor Type 1 Protein Tyrosine Phosphatase Human genes 0.000 description 1
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 description 1
- 102400000050 Oxytocin Human genes 0.000 description 1
- 101800000989 Oxytocin Proteins 0.000 description 1
- XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 description 1
- 108010035766 P-Selectin Proteins 0.000 description 1
- 102100023472 P-selectin Human genes 0.000 description 1
- 102100034925 P-selectin glycoprotein ligand 1 Human genes 0.000 description 1
- 108010054395 P-selectin ligand protein Proteins 0.000 description 1
- 102400000160 Thymopentin Human genes 0.000 description 1
- 101800001703 Thymopentin Proteins 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 108010089833 chemokine receptor D6 Proteins 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000003118 drug derivative Substances 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- 210000003989 endothelium vascular Anatomy 0.000 description 1
- VOCYLUBGGCPMED-UHFFFAOYSA-N fluoro hydrogen sulfate Chemical compound OS(=O)(=O)OF VOCYLUBGGCPMED-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- USSYUMHVHQSYNA-SLDJZXPVSA-N indolicidin Chemical compound CC[C@H](C)[C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)CC1=CNC2=CC=CC=C12 USSYUMHVHQSYNA-SLDJZXPVSA-N 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 description 1
- 229960001723 oxytocin Drugs 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- PSWFFKRAVBDQEG-YGQNSOCVSA-N thymopentin Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 PSWFFKRAVBDQEG-YGQNSOCVSA-N 0.000 description 1
- 229960004517 thymopentin Drugs 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462008925P | 2014-06-06 | 2014-06-06 | |
| US62/008,925 | 2014-06-06 | ||
| PCT/US2015/034516 WO2015188120A1 (en) | 2014-06-06 | 2015-06-05 | Sulfur(vi) fluoride compounds and methods for the preparation thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020121863A Division JP7227946B2 (ja) | 2014-06-06 | 2020-07-16 | フッ化硫黄（ｖｉ）化合物およびそれの製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017524731A JP2017524731A (ja) | 2017-08-31 |
| JP2017524731A5 true JP2017524731A5 (enExample) | 2018-02-08 |
| JP6738326B2 JP6738326B2 (ja) | 2020-08-12 |
Family
ID=54767460
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017516642A Active JP6738326B2 (ja) | 2014-06-06 | 2015-06-05 | フッ化硫黄（ｖｉ）化合物およびそれの製造方法 |
| JP2020121863A Active JP7227946B2 (ja) | 2014-06-06 | 2020-07-16 | フッ化硫黄（ｖｉ）化合物およびそれの製造方法 |
| JP2023018938A Pending JP2023075089A (ja) | 2014-06-06 | 2023-02-10 | フッ化硫黄（ｖｉ）化合物およびそれの製造方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020121863A Active JP7227946B2 (ja) | 2014-06-06 | 2020-07-16 | フッ化硫黄（ｖｉ）化合物およびそれの製造方法 |
| JP2023018938A Pending JP2023075089A (ja) | 2014-06-06 | 2023-02-10 | フッ化硫黄（ｖｉ）化合物およびそれの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (5) | US10117840B2 (enExample) |
| EP (3) | EP4295841A3 (enExample) |
| JP (3) | JP6738326B2 (enExample) |
| CN (2) | CN111689929B (enExample) |
| AU (4) | AU2015269198B2 (enExample) |
| CA (1) | CA2953237C (enExample) |
| ES (2) | ES2956953T3 (enExample) |
| WO (1) | WO2015188120A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11406742B2 (en) | 2014-07-18 | 2022-08-09 | M.A. Med Alliance SA | Coating for intraluminal expandable catheter providing contact transfer of drug micro-reservoirs |
| US10717820B2 (en) | 2015-06-22 | 2020-07-21 | The Scripps Research Institute | Polymerization of silyl- and fluoro-containing monomers |
| WO2017161183A1 (en) | 2016-03-16 | 2017-09-21 | The Regents Of The University Of California | Covalent peptide binders |
| MX2019005823A (es) | 2016-11-19 | 2019-07-10 | Trinapco Inc | Metodo de elaboracion de n-(fluorosulfonil) dimetilamina. |
| WO2018102433A1 (en) * | 2016-11-29 | 2018-06-07 | The Scripps Research Institute | Thionyl tetrafluoride modified compounds and uses |
| CA3050309A1 (en) | 2017-01-31 | 2018-08-09 | Arvinas Operations, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| CN107353287B (zh) * | 2017-05-26 | 2019-11-05 | 重庆文理学院 | 一种喹喔啉并杂氮环丁酮类化合物及其在抗肿瘤中的应用 |
| WO2019036517A1 (en) | 2017-08-14 | 2019-02-21 | Bioduro, Llc | REAGENTS FOR THE FLUOROSULFATION OF ALCOHOLS OR AMINES |
| US11091442B2 (en) | 2017-11-22 | 2021-08-17 | Shanghai Institute Of Organic Chemistry, Chinese Academy Of Sciences | Fluorosulfonyl-containing compound, intermediate thereof, preparation method therefor and use thereof |
| CN109867648A (zh) * | 2017-12-02 | 2019-06-11 | 浙江医药股份有限公司新昌制药厂 | 一种依帕列净有关物质impd的合成方法 |
| WO2019139979A2 (en) * | 2018-01-09 | 2019-07-18 | The Scripps Research Institute | Arylfluorosulfate compounds and methods |
| CN110217764B (zh) * | 2018-03-02 | 2022-08-09 | 中国科学院上海有机化学研究所 | 一种双氟磺酰亚胺的有机碱盐的制备方法 |
| KR102062848B1 (ko) | 2018-03-06 | 2020-01-06 | 서울대학교산학협력단 | 선택적으로 기능화된 타이로신을 가지는 생체 물질의 제조방법, 선택적으로 기능화된 타이로신을 가지는 생체 물질 및 이를 유효성분으로 함유하는 약학적 조성물 |
| JP7520718B2 (ja) * | 2018-03-08 | 2024-07-23 | ザ・リージエンツ・オブ・ザ・ユニバーシテイー・オブ・カリフオルニア | 生体反応性組成物およびそれらの使用方法 |
| CN108530372A (zh) * | 2018-05-08 | 2018-09-14 | 武汉理工大学 | 一种5-磺酰氟取代异恶唑类化合物的制备方法 |
| WO2020119595A1 (zh) * | 2018-12-13 | 2020-06-18 | 中国科学院上海有机化学研究所 | 一种酚盐及其应用 |
| EP3924051B1 (en) | 2019-02-14 | 2024-11-13 | Paul A. Knepper | Composition and method for inhibiting platelet aggregation |
| CA3130763A1 (en) | 2019-02-25 | 2020-09-03 | Ginkgo Bioworks, Inc. | Biosynthesis of cannabinoids and cannabinoid precursors |
| CN110429336B (zh) * | 2019-07-24 | 2022-07-12 | 江苏国泰超威新材料有限公司 | 一种非水电解液及锂离子电池 |
| CN110668978B (zh) * | 2019-09-23 | 2025-08-26 | 广州天赐高新材料股份有限公司 | 双磺酸酯化合物及其制备方法以及电解液和储能装置 |
| WO2021119183A1 (en) | 2019-12-13 | 2021-06-17 | 712 North, Inc. | Tricyclic compounds with oma1/opa1 modulatory properties |
| CR20220353A (es) | 2019-12-19 | 2022-10-20 | Arvinas Operations Inc | Compuestos y métodos para la degradación dirigida del receptor de andrógenos |
| CN111040165A (zh) * | 2019-12-26 | 2020-04-21 | 白银图微新材料科技有限公司 | 聚磺酸酯类聚合物及其聚合方法 |
| CN113121401B (zh) * | 2020-01-16 | 2022-10-04 | 中国科学院上海有机化学研究所 | 一种n-取代羰基氟磺酰胺化合物、制备方法及其应用 |
| US20230111856A1 (en) * | 2020-03-02 | 2023-04-13 | University Of Southern California | Opioid receptor antagonists |
| CN112028987B (zh) * | 2020-06-01 | 2021-07-30 | 广东圣赛生物科技有限公司 | 一种结合免疫抑制分子pd-l1的蛋白药物 |
| CN111793010B (zh) * | 2020-06-28 | 2022-03-15 | 浙江工业大学 | 一种2,5二氯-4氨基苯磺酰氟的制备方法 |
| EP4200277A4 (en) | 2020-08-21 | 2024-10-23 | SES Holdings Pte. Ltd. | SYNTHESIS OF N,N-BRANCHED SULFAMOYL FLUORIDE COMPOUNDS USING BISMUTH TRIFLUORIDE |
| KR102888292B1 (ko) | 2020-10-30 | 2025-11-19 | 주식회사 엘지화학 | 술포닐플루오라이드기 함유 화합물 및 이의 제조방법 |
| CN112675298B (zh) * | 2020-12-28 | 2024-05-03 | 中国医学科学院医学生物学研究所 | 一种免疫佐剂、含有所述免疫佐剂的疫苗及制备方法和应用 |
| WO2022160357A1 (zh) * | 2021-02-01 | 2022-08-04 | 苏州大学 | 高分子凝胶用单体及高分子凝胶与制备方法 |
| CN114907241B (zh) * | 2021-02-09 | 2024-05-17 | 中宏鑫投资控股(深圳)有限公司 | 一种含氟磺酰基的胍类化合物及其制备方法和应用 |
| JP2024512297A (ja) * | 2021-03-01 | 2024-03-19 | ザ・リージエンツ・オブ・ザ・ユニバーシテイー・オブ・カリフオルニア | 生体反応性化合物及びその使用方法 |
| CN113097644B (zh) * | 2021-04-01 | 2023-03-31 | 河南锂动电源有限公司 | 一种SOFs-P5G/PVDF锂离子电池隔膜的制备方法 |
| US20240262791A1 (en) * | 2021-04-28 | 2024-08-08 | The Regents Of The University Of California | Bioreactive proteins containing unnatural amino acids |
| CN113248444B (zh) * | 2021-05-31 | 2022-07-19 | 福州大学 | 一种氟磺酰基自由基试剂及其制备方法和应用 |
| EP4347543A4 (en) * | 2021-06-02 | 2025-10-15 | Univ California | PROTEINS WITH UNNATURAL AMINO ACIDS AND METHODS OF USE |
| CN113548986B (zh) * | 2021-07-14 | 2023-05-23 | 首都医科大学脑重大疾病研究中心(北京脑重大疾病研究院) | 一种磺酰氟基化合物及其应用 |
| CN113387845B (zh) * | 2021-07-16 | 2022-12-20 | 国药集团化学试剂有限公司 | 一种苯甲基磺酰氟的制备方法 |
| EP4212151B1 (en) | 2022-01-13 | 2025-03-12 | Paul A. Knepper | Stilbene, flavonol or curcumin compounds for use in the treatment of age-related macular degeneration (amd; armd) |
| WO2023168108A2 (en) * | 2022-03-04 | 2023-09-07 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Synthesis of sulfur(vi) compounds and reagents for same |
| JP2025529561A (ja) * | 2022-09-16 | 2025-09-04 | ドッグウッド セラピューティクス インコーポレイテッド | アルツハイマー病及びｃｏｖｉｄ－１９の治療のためのバラシクロビル及びセレコキシブ |
| WO2024097831A1 (en) * | 2022-11-02 | 2024-05-10 | The Regents Of The University Of California | Bioreactive proteins containing unnatural amino acids |
| CN118546080A (zh) * | 2024-05-15 | 2024-08-27 | 济南大学 | 一种芳基氟磺酸盐化合物的制备方法 |
| US12303604B1 (en) | 2024-10-16 | 2025-05-20 | Currax Pharmaceuticals Llc | Pharmaceutical formulations comprising naltrexone and/or bupropion |
| CN119751372B (zh) * | 2024-12-20 | 2025-11-25 | 江南大学 | 一种2-氧代-4-苯基恶嗪磺酰氟的制备方法 |
| CN120040411B (zh) * | 2025-01-07 | 2025-11-07 | 浙江大学衢州研究院 | 一种一锅法制备芳基冠醚化合物的方法 |
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