KR102643910B1 - 1,4-다이엔 시스템에 대한 부위 특이적인 동위원소 표지법 - Google Patents

1,4-다이엔 시스템에 대한 부위 특이적인 동위원소 표지법 Download PDF

Info

Publication number
KR102643910B1
KR102643910B1 KR1020187017573A KR20187017573A KR102643910B1 KR 102643910 B1 KR102643910 B1 KR 102643910B1 KR 1020187017573 A KR1020187017573 A KR 1020187017573A KR 20187017573 A KR20187017573 A KR 20187017573A KR 102643910 B1 KR102643910 B1 KR 102643910B1
Authority
KR
South Korea
Prior art keywords
allyl
group
paragraph
polyunsaturated fat
bis
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.)
Active
Application number
KR1020187017573A
Other languages
English (en)
Korean (ko)
Other versions
KR20180091020A (ko
Inventor
드라고슬라브 비도빅
미하일 세르기비치 셰피노브
Original Assignee
레트로토프 인코포레이티드
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 레트로토프 인코포레이티드 filed Critical 레트로토프 인코포레이티드
Publication of KR20180091020A publication Critical patent/KR20180091020A/ko
Application granted granted Critical
Publication of KR102643910B1 publication Critical patent/KR102643910B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/001—Acyclic or carbocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/231—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having one or two double bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/232—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having three or more double bonds, e.g. etretinate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/12—Alkadienes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/21—Alkatrienes; Alkatetraenes; Other alkapolyenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/16—Peroxy compounds the —O—O— group being bound between two carbon atoms not further substituted by oxygen atoms, i.e. peroxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • 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
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
    • C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
    • C07C2523/46—Ruthenium, rhodium, osmium or iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/24—Phosphines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biochemistry (AREA)
  • Ophthalmology & Optometry (AREA)
  • Toxicology (AREA)
  • Neurosurgery (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Vascular Medicine (AREA)
  • Rheumatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
KR1020187017573A 2015-11-23 2016-09-09 1,4-다이엔 시스템에 대한 부위 특이적인 동위원소 표지법 Active KR102643910B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562258993P 2015-11-23 2015-11-23
US62/258,993 2015-11-23
PCT/US2016/051119 WO2017091279A1 (en) 2015-11-23 2016-09-09 Site-specific isotopic labeling of 1, 4-diene systems

Publications (2)

Publication Number Publication Date
KR20180091020A KR20180091020A (ko) 2018-08-14
KR102643910B1 true KR102643910B1 (ko) 2024-03-06

Family

ID=58763673

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020187017573A Active KR102643910B1 (ko) 2015-11-23 2016-09-09 1,4-다이엔 시스템에 대한 부위 특이적인 동위원소 표지법

Country Status (10)

Country Link
US (7) US10730821B2 (https=)
EP (3) EP3950649A1 (https=)
JP (2) JP7048976B2 (https=)
KR (1) KR102643910B1 (https=)
CN (2) CN108698987B (https=)
AU (4) AU2016361227B2 (https=)
CA (1) CA3005983A1 (https=)
ES (1) ES2871130T3 (https=)
IL (2) IL259516B (https=)
WO (1) WO2017091279A1 (https=)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3950649A1 (en) 2015-11-23 2022-02-09 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
EP3773541A4 (en) * 2018-04-04 2022-01-05 Retrotope, Inc. ISOTOPICALLY MODIFIED COMPOSITION AND ITS THERAPEUTIC USES
EP3880194A4 (en) * 2018-11-15 2022-11-09 Retrotope, Inc. DEUTERED COMPOUNDS, COMPOSITIONS AND USES
IL295783B2 (en) * 2020-02-21 2026-03-01 Retrotope Inc Processes for isotopic alteration 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
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
US11491130B2 (en) 2021-02-05 2022-11-08 Retrotope, Inc. Methods of treating amyotrophic lateral sclerosis
EP4373479A4 (en) * 2021-07-22 2025-11-05 Biojiva Llc METHODS FOR INHIBITING THE PROGRESSION OF OXIDATIVE RETINAL DISEASES
IL313592A (en) * 2021-12-21 2024-08-01 Biojiva Llc Methods and preparations for the treatment of inflammatory disease
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
WO2023220058A1 (en) 2022-05-09 2023-11-16 Retrotope, Inc. 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
AU750245B2 (en) 1997-10-08 2002-07-11 Aurinia Phamaceuticals Inc. Deuterated cyclosporine analogs and their use as immunomodulating agents
US6270974B1 (en) 1998-03-13 2001-08-07 Promega Corporation Exogenous nucleic acid detection
EP1075286A2 (en) 1998-05-06 2001-02-14 Isotechnika, Inc. 13c glucose breath test for the diagnosis of diabetes
ATE361066T1 (de) 1998-10-15 2007-05-15 Dsm Ip Assets Bv Polyungesättigen fettsäuren nährungsergänzung
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
ATE291910T1 (de) 2001-05-30 2005-04-15 Laxdale Ltd Verwendung von coenzym q (ubiquinone) und eikosapentaensäure (epa) für die behandlung von non-hodgkin's lymphoma und psychiatrischen oder neurologischen erkrankungen
GB0113348D0 (en) 2001-06-01 2001-07-25 Mars Uk Ltd Skin diet
KR20040058192A (ko) 2001-10-19 2004-07-03 맥심 파마수티컬즈 인크. 간 질환 치료용으로서의 히스타민 용도
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
EP1551399A4 (en) 2002-09-30 2011-01-05 Mark A Babizhayev METHOD FOR THE TOPICAL TREATMENT OF EYE DISEASES AND COMPOSITION AND DEVICE FOR THIS TREATMENT
AU2003268693A1 (en) 2002-09-30 2004-04-19 Ajinomoto Co., Inc. Method of producing stable isotope-labeled protein
CN1717234A (zh) 2002-12-06 2006-01-04 爱尔康公司 用于治疗眼紊乱和疾病的超氧化物岐化酶模拟物
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 DYSFUNCTION OR DICTION AND ASSOCIATED TECHNIQUES
US20050164908A1 (en) 2004-01-23 2005-07-28 Ginsberg Myron D. Neuroprotective complex for treatment of cerebral ischemia and injury
EP1841460A2 (en) 2004-06-18 2007-10-10 Neurochem (International) Limited Therapeutic formulations for the treatment of beta-amyloid related diseases
AU2005270825B2 (en) 2004-08-09 2011-07-07 Enzymotec Ltd. 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
BRPI0516803A (pt) 2004-11-19 2008-09-23 Martek Biosciences Corp oxilipinas de ácidos graxos polinsaturados de cadeia longa e métodos de produção e uso dos mesmos
EP1834639B8 (en) 2005-01-04 2016-12-07 Mochida Pharmaceutical Co., Ltd. Remedial agent for fat toxicity
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
BRPI0613358A8 (pt) 2005-07-08 2017-12-26 Dsm Ip Assets Bv ácidos de gordura poli - insaturada para o tratamento da demência e condições relacionadas à pré-demência
WO2007073560A2 (en) 2005-12-20 2007-06-28 Rnd Pharmaceuticals, Inc. Pharmaceutical compositions and methods of use of highly lipophilic sulfhydryl compounds
WO2007081773A2 (en) 2006-01-05 2007-07-19 Reliant Pharmaceuticals, Inc Treatment of fatty liver
EP1978962A2 (en) 2006-01-05 2008-10-15 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
EP2136638A4 (en) 2007-03-14 2010-05-12 Knopp Neurosciences Inc MODIFIED RELEASE FORMULATIONS OF (6R) -4,5,6,7-TETRAHYDRO-N6-PROPYL-2,6-BENZOTHIAZOLE DIAMINE AND METHODS OF USE THEREOF
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)
JP5314931B2 (ja) 2007-05-25 2013-10-16 参天製薬株式会社 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
ES2700141T3 (es) 2007-08-02 2019-02-14 Gilead Biologics Inc Anticuerpos inhibidores LOXL2 y usos de los mismos
US20090069354A1 (en) 2007-09-12 2009-03-12 Protia, Llc Deuterium-enriched gemcitabine
WO2009056983A1 (en) 2007-10-31 2009-05-07 Pronova Biopharma Norge As New dha derivatives and their use as medicaments
WO2009097331A1 (en) 2008-01-28 2009-08-06 The Board Of Regents Of The University Of Oklahoma Very long chain polyunsaturated fatty acids, methods of production, and uses
JP2011514361A (ja) 2008-03-14 2011-05-06 レトロトップ、 インコーポレイテッド 同位体で置換されたリジンを用いたがん治療
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
CA2720343A1 (en) 2008-04-04 2009-10-08 Takeda Pharmaceutical Company Limited Heterocyclic derivative and use thereof
JP2011519373A (ja) 2008-05-01 2011-07-07 コンプレクザ インコーポレイテッド ビニル置換脂肪酸
US20110092592A1 (en) 2008-06-13 2011-04-21 Takashi Yano Diagnosis and treatment of hepatic disorder
GB0813599D0 (en) 2008-07-24 2008-09-03 Pharma Marine As Method
CA2731171C (en) 2008-07-28 2016-10-18 Blanchette Rockefeller Neurosciences Institute Pkc-activating compounds for the treatment of neurodegenerative diseases
US20110268699A1 (en) 2008-12-11 2011-11-03 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.
WO2010132347A2 (en) 2009-05-11 2010-11-18 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
EP2483233A4 (en) 2009-10-02 2013-08-14 Complexa Inc HETEROATOMA 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
WO2012067111A1 (ja) 2010-11-16 2012-05-24 株式会社西崎創薬研究所 ＰＫＣ－ε活性化剤
KR102112087B1 (ko) 2011-04-26 2020-05-18 레트로토프 인코포레이티드 에너지 프로세싱 손상 장애 및 미토콘드리아 결함
JP6145087B2 (ja) * 2011-04-26 2017-06-07 レトロトップ、 インコーポレイテッドＲｅｔｒｏｔｏｐｅ， Ｉｎｃ． Ｐｕｆａ酸化関与障害
JP6106157B2 (ja) * 2011-04-26 2017-03-29 レトロトップ、 インコーポレイテッドＲｅｔｒｏｔｏｐｅ， Ｉｎｃ． 神経変性障害および筋疾患に関与するｐｕｆａ
WO2012148930A2 (en) 2011-04-26 2012-11-01 Retrotope, Inc. Oxidative retinal diseases
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
EP3950649A1 (en) * 2015-11-23 2022-02-09 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
IL295783B2 (en) 2020-02-21 2026-03-01 Retrotope Inc Processes for isotopic alteration 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
Journal of biological chemistry, 1983, 258, 3, 1427-1430, 1부.*
Top. Catal., 2010, 53, 1055, 1부.*

Also Published As

Publication number Publication date
IL259516A (en) 2018-07-31
KR20180091020A (ko) 2018-08-14
AU2021225202B2 (en) 2023-04-13
EP3380452A4 (en) 2019-05-15
JP2019501135A (ja) 2019-01-17
JP7048976B2 (ja) 2022-04-06
AU2016361227A1 (en) 2018-06-21
EP3380452B1 (en) 2021-03-24
EP3950649A1 (en) 2022-02-09
ES2871130T3 (es) 2021-10-28
US11453637B2 (en) 2022-09-27
US20200109103A1 (en) 2020-04-09
US20240018085A1 (en) 2024-01-18
JP7355801B2 (ja) 2023-10-03
US20180339958A1 (en) 2018-11-29
CN108698987B (zh) 2021-07-13
AU2025202677A1 (en) 2025-05-08
EP3858843A1 (en) 2021-08-04
CA3005983A1 (en) 2017-06-01
EP3380452A1 (en) 2018-10-03
US20190084913A1 (en) 2019-03-21
CN108698987A (zh) 2018-10-23
US20210331998A1 (en) 2021-10-28
US10730821B2 (en) 2020-08-04
US10577304B2 (en) 2020-03-03
AU2016361227B2 (en) 2021-06-10
JP2022046501A (ja) 2022-03-23
AU2021225202A1 (en) 2021-09-30
WO2017091279A1 (en) 2017-06-01
US11447441B2 (en) 2022-09-20
IL285758A (en) 2021-09-30
IL259516B (en) 2021-09-30
CN113214084A (zh) 2021-08-06
IL285758B (en) 2022-05-01
US20210387938A1 (en) 2021-12-16
US20250223253A1 (en) 2025-07-10
US12060324B2 (en) 2024-08-13
AU2023204024A1 (en) 2023-07-13
AU2023204024B2 (en) 2025-04-03

Similar Documents

Publication Publication Date Title
KR102643910B1 (ko) 1,4-다이엔 시스템에 대한 부위 특이적인 동위원소 표지법
JP6674586B2 (ja) 血液脳関門通過能を有する置換キナゾリン化合物
AU2001251449A1 (en) Conjugated linoleic acid compositions
WO2001077271A2 (en) Conjugated linoleic acid compositions
HK40068751A (en) Site-specific isotopic labeling of 1,4-diene systems
HK40057018A (en) Site-specific isotopic labeling of 1, 4-diene systems
HK40056928A (en) Site-specific isotopic labeling of 1, 4-diene systems
HK1261107B (en) Site-specific isotopic labeling of 1, 4-diene systems
Kubeil et al. Copper (II) Cyclam Complexes with N‐Propionic Acid Pendant Arms
JP6173440B2 (ja) 新規美白剤
JPH04295423A (ja) 制がん剤および制がん増強剤

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20180620

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
A201 Request for examination
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20210714

Comment text: Request for Examination of Application

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20230612

Patent event code: PE09021S01D

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

Patent event code: PE07011S01D

Comment text: Decision to Grant Registration

Patent event date: 20231201

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20240229

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20240229

End annual number: 3

Start annual number: 1

PG1601 Publication of registration