CN108698987B - 1,4-二烯体系的位点特异性同位素标记 - Google Patents

1,4-二烯体系的位点特异性同位素标记 Download PDF

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CN108698987B
CN108698987B CN201680079610.2A CN201680079610A CN108698987B CN 108698987 B CN108698987 B CN 108698987B CN 201680079610 A CN201680079610 A CN 201680079610A CN 108698987 B CN108698987 B CN 108698987B
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polyunsaturated
group
polyunsaturated lipid
lipid
alkyl
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CN108698987A (zh
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德拉斯拉夫·维多维克
米哈伊尔·谢尔盖维奇·什彻皮诺夫
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Baiojiwa Co ltd
Rtmfp Enterprise Ltd
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Retrotope Inc
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    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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CN201680079610.2A 2015-11-23 2016-09-09 1,4-二烯体系的位点特异性同位素标记 Active CN108698987B (zh)

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Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017091279A1 (en) 2015-11-23 2017-06-01 Retrotope, Inc. Site-specific isotopic labeling of 1, 4-diene systems
US11478437B2 (en) 2016-07-05 2022-10-25 Jenivision Inc. Formulations for hair growth
CA3096035A1 (en) * 2018-04-04 2019-10-10 Retrotope, Inc. Isotopically modified composition and therapeutic uses thereof
WO2020102596A1 (en) * 2018-11-15 2020-05-22 Retrotope, Inc. Deuterated compounds, compositions, and uses
EP4107163A4 (en) * 2020-02-21 2024-06-19 Retrotope, Inc. PROCESSES FOR ISOTOPIC MODIFICATION OF POLYUNSATURATED FATTY ACIDS AND THEIR DERIVATIVES
CN111454114B (zh) * 2020-05-11 2023-07-14 长沙贝塔医药科技有限公司 一种用13c2-香叶醇合成高纯度13c2-月桂烯的方法
US11491130B2 (en) 2021-02-05 2022-11-08 Retrotope, Inc. Methods of treating amyotrophic lateral sclerosis
US12109194B2 (en) 2021-02-05 2024-10-08 Biojiva Llc Synergistic combination therapy for treating ALS
US11510889B2 (en) 2021-02-05 2022-11-29 Retrotope, Inc. Methods for inhibiting the progression of neurodegenerative diseases
EP4373479A4 (en) * 2021-07-22 2025-11-05 Biojiva Llc METHODS FOR INHIBITING THE PROGRESSION OF OXIDATIVE RETINAL DISEASES
EP4201403A1 (en) 2021-12-21 2023-06-28 Som Innovation Biotech, S.L. Compounds tirapazamine and quazinone for use in the treatment of gm2 gangliosidoses
CA3243042A1 (en) * 2021-12-21 2025-04-08 Biojiva Llc METHODS AND COMPOSITIONS INTENDED FOR THE TREATMENT OF INFLAMMATORY DISEASE
AU2023269025A1 (en) 2022-05-09 2024-12-19 Biojiva Llc Therapeutic methods for treating als
CN115894143B (zh) * 2022-10-31 2024-05-28 宁波萃英化学技术有限公司 氘代芳香化合物钯催化的双配体无导向制备方法
CN117456313B (zh) * 2023-12-22 2024-03-22 中国科学院宁波材料技术与工程研究所 色调曲线估计网络的训练方法、估计、映射方法及系统

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110105609A1 (en) * 2009-10-30 2011-05-05 Retrotope, Inc. Alleviating oxidative stress disorders with pufa derivatives

Family Cites Families (103)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3520872A (en) 1967-03-24 1970-07-21 Upjohn Co Process for labelling purine and pyrimidine containing compounds
US4792620A (en) * 1983-10-14 1988-12-20 Bp Chemicals Limited Carbonylation catalysts
IT1205043B (it) 1987-05-28 1989-03-10 Innova Di Ridolfi Flora & C S Procedimento per l'estrazione di esteri di acidi grassi poliinsaturi da olii di pesce e composizioni farmaceutiche e dietetiche contenenti detti esteri
JPH0614512Y2 (ja) 1987-10-29 1994-04-13 シャープ株式会社 アンテナ端子板
US5340742A (en) 1988-09-07 1994-08-23 Omegatech Inc. Process for growing thraustochytrium and schizochytrium using non-chloride salts to produce a microfloral biomass having omega-3-highly unsaturated fatty acids
JPH0291955A (ja) 1988-09-29 1990-03-30 Nec Kansai Ltd 半導体ペレットのマウント方法
AU620929B2 (en) 1988-10-27 1992-02-27 Bar-Ilan University Method and compositions for treating alzheimer's disease, related dementias and epilepsy
DK0455783T3 (da) 1989-11-30 1996-04-01 Croda Int Plc Anvendelse af nervonsyre og langkædede fedtsyrer til behandlingen af demyeliniserende sygdomme
JPH0481156A (ja) 1990-07-24 1992-03-13 Matsushita Electric Ind Co Ltd コードレステレホン
ES2033193B1 (es) 1990-10-30 1994-01-16 Ganadera Union Ind Agro Mezcla grasa para nutricion infantil y de adultos.
EP0567653A4 (en) 1991-11-14 1994-06-01 Sagami Chem Res Drug for hepatic diseases
JPH05246938A (ja) * 1992-02-19 1993-09-24 Sagami Chem Res Center 重水素標識高級脂肪酸
CN1152316A (zh) 1994-05-19 1997-06-18 麦克公司 具有烯丙基的甾族化合物的氧化
FR2721518B3 (fr) 1994-06-28 1996-04-12 Gattefosse Ets Sa Compositions cosmétiques, pharmaceutiques, diététiques, vétérinaires contenant de l'eau.
FR2722410B1 (fr) 1994-07-15 1996-10-04 Grinda Jean Robert Procede de stabilisation des acides gras poly-insatures et utilisation de ces produits stabilises entherapeutique
GB9423625D0 (en) 1994-11-23 1995-01-11 Scotia Holdings Plc Fortified fruit juice
JPH08268885A (ja) 1995-03-30 1996-10-15 Oyo Seikagaku Kenkyusho 過酸化脂質増量抑制剤
US5578334A (en) 1995-04-07 1996-11-26 Brandeis University Increasing the HDL level and the HDL/LDL ratio in human serum with fat blends
CN1114878A (zh) 1995-06-09 1996-01-17 郑州铁路局中心医院 一种防治心血管系统疾病的制剂
JPH0950274A (ja) 1995-08-07 1997-02-18 Kawai Musical Instr Mfg Co Ltd アップライトピアノのフレーム
JPH09143492A (ja) 1995-11-17 1997-06-03 Katsumasa Koike 酸化脂質の確認方法及び酸化脂質の生成方法
JPH10291955A (ja) 1997-04-22 1998-11-04 Sagami Chem Res Center １３ｃ標識ドコサヘキサエン酸及びその製造方法
JPH1070439A (ja) 1996-08-29 1998-03-10 Hitachi Ltd 受信装置
US20030013772A1 (en) 2000-02-23 2003-01-16 Murphy Michael A. Composition, synthesis and therapeutic applications of polyamines
US6111066A (en) 1997-09-02 2000-08-29 Martek Biosciences Corporation Peptidic molecules which have been isotopically substituted with 13 C, 15 N and 2 H in the backbone but not in the sidechains
DE69832984T2 (de) 1997-10-08 2006-09-21 Isotechnika, Inc., Edmonton DEUTERIERtE und undeuterierte CYCLOSPORIN-ANALOGA UND IHRE VERWENDUNG ALS IMMUNMODULIERENDE AGENtIEN
US6270974B1 (en) 1998-03-13 2001-08-07 Promega Corporation Exogenous nucleic acid detection
US6468802B1 (en) 1998-05-06 2002-10-22 Isotechnika, Inc. 13C glucose breath test for the diagnosis of diabetic indications and monitoring glycemic control
CN1326344A (zh) 1998-10-15 2001-12-12 Dsm公司 Pufa增补剂
IT1304406B1 (it) 1998-10-21 2001-03-19 Danital Italia S R L Preparazione per la veicolazione di principi attivi basata su acidigrassi polinsaturi del gruppo omega 3.
US6503478B2 (en) 1999-01-13 2003-01-07 Lightouch Medical, Inc. Chemically specific imaging of tissue
US7271315B2 (en) 1999-01-14 2007-09-18 Martek Biosciences Corporation PUFA polyketide synthase systems and uses thereof
JP2000290291A (ja) 1999-03-31 2000-10-17 Nippon Sanso Corp 安定同位体標識オリゴヌクレオチド及びオリゴヌクレオチド検出方法
GB9916536D0 (en) * 1999-07-14 1999-09-15 Scarista Limited Nutritional or pharmaceutical compositions
ITMI991894A1 (it) 1999-09-09 2001-03-09 Carlo Ghisalberti Acido linoleico coniugato e trigliceride nuovi metodi di sintesi e d'uso
JP3432778B2 (ja) 1999-11-19 2003-08-04 森澤 紳勝 活性酸素消去剤の濃縮液、その製造方法および活性酸素消去剤パウダー
GB9929897D0 (en) 1999-12-18 2000-02-09 Slabas Antoni R Improvements in or relating to conjugated fatty acids and related compounds
JP2001270832A (ja) 2000-03-27 2001-10-02 Ito En Ltd 網膜障害予防剤
GB2368339B (en) 2000-10-26 2002-09-18 Yissum Res Dev Co Complex incorporating a plurality of antioxidants
US20040043013A1 (en) 2000-12-28 2004-03-04 Mccleary Edward Larry Metabolic uncoupling therapy
US20020198177A1 (en) 2001-05-30 2002-12-26 Horrobin David Frederick Coenzyme Q and EPA
GB0113348D0 (en) 2001-06-01 2001-07-25 Mars Uk Ltd Skin diet
WO2003035095A1 (en) 2001-10-19 2003-05-01 Maxim Pharmaceuticals, Inc. Use of histamine to treat liver disease
US6870077B2 (en) 2002-01-30 2005-03-22 Edward O. Kenaschuk High linolenic acid flax
US7582785B2 (en) 2002-04-01 2009-09-01 University Of Southern California Trihydroxy polyunsaturated eicosanoid derivatives
JP2004081156A (ja) 2002-08-28 2004-03-18 Shigeo Ota 糖尿病および糖尿病関連疾患の予測のためのマーカーおよび個体分類方法
EP1548116A4 (en) 2002-09-30 2006-04-05 Ajinomoto Kk PROCESS FOR PRODUCING A PROTEIN MARKED BY A STABLE ISOTOPE
US7795203B2 (en) 2002-09-30 2010-09-14 Babizhayev Mark A Method for topical treatment of eye disease and composition and device for said treatment
MXPA05005240A (es) 2002-12-06 2005-07-25 Alcon Inc Imitadores de la superoxido - dismutasa para el tratamiento de desordenes y enfermedades oculares.
TW200413274A (en) 2002-12-27 2004-08-01 Wako Pure Chem Ind Ltd Deuteration or tritiation method
KR20050029582A (ko) 2003-09-23 2005-03-28 주식회사 리포젠 알지닌 공액리놀레인산 복합체를 포함하는 항산화 조성물
IL158552A0 (en) 2003-10-22 2004-05-12 Enzymotec Ltd Lipids containing omega-3 fatty acids
EP1713463A4 (en) 2004-01-19 2009-03-18 Martek Biosciences Corp REELIN LACK OR DYSFUNCTION AND RELEVANT PROCEDURE
US20050164908A1 (en) 2004-01-23 2005-07-28 Ginsberg Myron D. Neuroprotective complex for treatment of cerebral ischemia and injury
JP2008504372A (ja) 2004-06-18 2008-02-14 ニューロケム （インターナショナル） リミティッド β−アミロイド関連疾患の治療のための治療用製剤
US20090232916A1 (en) 2004-08-09 2009-09-17 Avidor Shulman Food products for diabetics
JP2006053100A (ja) 2004-08-13 2006-02-23 Institute Of Physical & Chemical Research 動物の代謝解析方法、ラベル動物の製造方法、ラベル動物、および、動物のｎｍｒ測定方法
CA2588166A1 (en) 2004-11-19 2006-05-26 Martek Biosciences Corporation Oxylipins from long chain polyunsaturated fatty acids and methods of making and using the same
WO2006073147A1 (ja) 2005-01-04 2006-07-13 Mochida Pharmaceutical Co., Ltd. 脂肪毒性の改善剤
US7250416B2 (en) 2005-03-11 2007-07-31 Supergen, Inc. Azacytosine analogs and derivatives
US20070004639A1 (en) 2005-07-01 2007-01-04 Bodybio, Inc. Methods and compositions for treating Parkinson's disease
KR20130101596A (ko) 2005-07-08 2013-09-13 마텍 바이오싸이언스스 코포레이션 치매 및 치매-전단계와 관련된 용태의 치료를 위한 다중불포화 지방산
JP2009525948A (ja) 2005-12-20 2009-07-16 シラメッド・インコーポレーテッド 高親油性スルフヒドリル化合物の製薬組成物及び使用方法
EP1973536A2 (en) 2006-01-05 2008-10-01 Reliant Pharmaceuticals, Inc. Treatment of fatty liver
WO2007081910A2 (en) 2006-01-05 2007-07-19 Kinemed, Inc. Compositions and methods of treatment using modulators of motonueron diseases
JP5137168B2 (ja) 2006-02-27 2013-02-06 独立行政法人科学技術振興機構 安定同位体標識脂肪族アミノ酸、その標的蛋白質への組み込み方法並びに蛋白質のｎｍｒ構造解析方法
GB0604647D0 (en) 2006-03-08 2006-04-19 Shchepinov Mikhail Stabilized food supplements and their derivatives
WO2008143642A2 (en) 2006-11-09 2008-11-27 Children's Medical Center Corporation Methods of treating and preventing ocular neovascularization with omega-3 polyunsaturated fatty acids
US8524695B2 (en) 2006-12-14 2013-09-03 Knopp Neurosciences, Inc. Modified release formulations of (6R)-4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine and methods of using the same
EP1961311A1 (en) 2007-02-23 2008-08-27 Belovo S.A., Egg Science & Technology Food comprising polyunsaturated fatty acids for the prevention of chronic diseases
CN101677564A (zh) 2007-03-14 2010-03-24 诺普神经科学股份有限公司 (6r)-4,5,6,7-四氢-n6-丙基-2,6-苯并噻唑-二胺的改良释放制剂及其使用方法
US20080234197A1 (en) 2007-03-19 2008-09-25 Undurti N Das Method(s) of stabilizing and potentiating the actions and administration of brain-derived neurotrophic factor (BDNF)
WO2008146721A1 (ja) 2007-05-25 2008-12-04 Santen Pharmaceutical Co., Ltd. 加齢黄斑変性の予防又は治療剤
US8501032B2 (en) 2007-07-26 2013-08-06 San Diego State University (Sdsu) Foundation Catalysts for alkene isomerization and conjugating double bonds in polyunsaturated fats and oils
CA2693310C (en) 2007-08-02 2018-11-27 Arresto Biosciences, Inc. Lox and loxl2 inhibitors, antibodies and uses thereof
US20090069354A1 (en) 2007-09-12 2009-03-12 Protia, Llc Deuterium-enriched gemcitabine
KR20100100818A (ko) 2007-10-31 2010-09-15 프로노바 바이오파마 노르지 에이에스 새로운 ｄｈａ 유도체 및 약물로서 그들의 사용
US8021874B2 (en) 2008-01-28 2011-09-20 The Board Of Regents Of The University Of Oklahoma Very long chain polyunsaturated fatty acids, methods of production, and uses
DK2268604T3 (en) 2008-03-14 2017-03-27 Retrotope Inc CANCER THERAPIES BY USING ISOTO-SUBSTITUTED LYSIN
US8637486B2 (en) 2008-03-14 2014-01-28 Retrotope, Inc. Therapeutic substances that modulate genome methylation
EP2110027A1 (en) 2008-04-01 2009-10-21 Nestec S.A. Long-chain polyunsaturated fatty acids (LC-PUFA) in maternal nutrition during pregnancy and lactation
CN102056907B (zh) 2008-04-04 2014-12-31 武田药品工业株式会社 杂环衍生物及其用途
DK2280928T3 (en) 2008-05-01 2018-11-05 Complexa Inc Vinyl-substituted fatty acids
JPWO2009151125A1 (ja) 2008-06-13 2011-11-17 持田製薬株式会社 肝障害の診断及び治療
GB0813599D0 (en) 2008-07-24 2008-09-03 Pharma Marine As Method
EP3403650A3 (en) 2008-07-28 2019-02-13 Blanchette Rockefeller Neurosciences, Institute Pkc-activating compounds for the treatment of neurodegenerative diseases
EP2375900B1 (en) 2008-12-11 2016-03-02 Biovista, Inc. Methods for treating multiple sclerosis using tetracyclic pyrazinoindoles
ES2345241B1 (es) 2009-03-16 2011-09-08 Lipopharma Therapeutics Uso de 2-hidroxiderivados de acidos grasos poliinsaturados como medicamentos.
US20120046363A1 (en) 2009-05-11 2012-02-23 University Of Maryland, Baltimore Docosahexaenoic acid for the treatment of heart failure
WO2010143053A1 (en) 2009-06-10 2010-12-16 Energy4Life Ag Methods and compositions for treating insulin resistance, diabetes mellitus type 2, metabolic syndrome and related disorders
WO2011041639A2 (en) 2009-10-02 2011-04-07 Miller Raymond A Heteroatom containing substituted fatty acids
WO2011097273A1 (en) 2010-02-02 2011-08-11 Martek Biosciences Corporation Methods and compositions for treating non-alcoholic fatty liver disease with docosahexaenoic acid and n-acetyl lcystenine
JP5896472B2 (ja) 2010-11-16 2016-03-30 株式会社 西崎創薬研究所 ＰＫＣ−ε活性化剤
US10154983B2 (en) 2011-04-26 2018-12-18 Retrotope, Inc. Neurodegenerative disorders and muscle diseases implicating PUFAs
WO2012148929A2 (en) * 2011-04-26 2012-11-01 Retrotope, Inc. Disorders implicating pufa oxidation
US10058522B2 (en) 2011-04-26 2018-08-28 Retrotope, Inc. Oxidative retinal diseases
KR102020579B1 (ko) 2011-04-26 2019-09-10 레트로토프 인코포레이티드 에너지 프로세싱 손상 장애 및 미토콘드리아 결함
WO2012174262A2 (en) 2011-06-14 2012-12-20 Cenestra Llc Formulations and methods of treating subjects having central nervous system, endocrine, inflammatory or cardiovascular disorders or at-risk thereof with highly purified omega-3 fatty acid formulations
AU2015229240B9 (en) 2014-03-13 2019-05-02 Biojiva Llc Optic neuropathy treatment and reduction of steroid-induced oxidative stress with stabilized polyunsaturated substances
WO2015162265A1 (en) * 2014-04-24 2015-10-29 Institut National De La Sante Et De La Recherche Medicale (Inserm) New lipophenol compounds and uses thereof
WO2017091279A1 (en) 2015-11-23 2017-06-01 Retrotope, Inc. Site-specific isotopic labeling of 1, 4-diene systems
CN107569684B (zh) 2016-07-05 2021-04-09 杰尼视界公司 生发配方
EP4107163A4 (en) 2020-02-21 2024-06-19 Retrotope, Inc. PROCESSES FOR ISOTOPIC MODIFICATION OF POLYUNSATURATED FATTY ACIDS AND THEIR DERIVATIVES

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110105609A1 (en) * 2009-10-30 2011-05-05 Retrotope, Inc. Alleviating oxidative stress disorders with pufa derivatives

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Development of deuterium labeling method based on the heterogeneous platinum group metal-catalyzed C-H activation;Hironao Sajiki;《The Pharmaceutical Society of Japan》;20131231;第133卷(第11期);第11页Table1 *
Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido-tris(triphenylphosphine)ruthenium(II) Complex;Sunny Kai San Tse et al;《Adv. Synth. Catal.》;20100528;第352卷;第1514页Table1 *

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