CN107709342B - 制备乙酰半乳糖胺酸衍生物的方法 - Google Patents

制备乙酰半乳糖胺酸衍生物的方法 Download PDF

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CN107709342B
CN107709342B CN201680038736.5A CN201680038736A CN107709342B CN 107709342 B CN107709342 B CN 107709342B CN 201680038736 A CN201680038736 A CN 201680038736A CN 107709342 B CN107709342 B CN 107709342B
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formula
acid
galnac
protecting group
ester
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CN107709342A (zh
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J·利尔
R·楚萨底
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F Hoffmann La Roche AG
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02Acyclic radicals, not substituted by cyclic structures
    • C07H15/04Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C07H15/08Polyoxyalkylene derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/549Sugars, nucleosides, nucleotides or nucleic acids
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/26Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/20Diazonium compounds
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • C07C271/08Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41Preparation of salts of carboxylic acids
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/125Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/10Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C07C67/11Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708Ethers
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    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00Processes for the preparation of sugar derivatives
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    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • C07H21/02Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with ribosyl as saccharide radical
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/02Ortho- or ortho- and peri-condensed systems
    • C07C2603/04Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18Fluorenes; Hydrogenated fluorenes
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CN201680038736.5A 2015-08-06 2016-08-02 制备乙酰半乳糖胺酸衍生物的方法 Active CN107709342B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP15180058.8 2015-08-06
EP15180058 2015-08-06
PCT/EP2016/068361 WO2017021385A1 (en) 2015-08-06 2016-08-02 Processes for the preparation of galnac acid derivatives

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CN107709342A CN107709342A (zh) 2018-02-16
CN107709342B true CN107709342B (zh) 2021-09-03

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US (1) US10597417B2 (OSRAM)
EP (1) EP3331892B1 (OSRAM)
JP (1) JP6940477B2 (OSRAM)
KR (1) KR102579520B1 (OSRAM)
CN (1) CN107709342B (OSRAM)
AU (1) AU2016302697B2 (OSRAM)
CA (1) CA2982825C (OSRAM)
ES (1) ES2744437T3 (OSRAM)
HR (1) HRP20191589T1 (OSRAM)
IL (1) IL256528B (OSRAM)
MX (1) MX369556B (OSRAM)
PL (1) PL3331892T3 (OSRAM)
SI (1) SI3331892T1 (OSRAM)
WO (1) WO2017021385A1 (OSRAM)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018215049A1 (en) 2017-05-23 2018-11-29 F. Hoffmann-La Roche Ag Process for galnac oligonucleotide conjugates
KR20200116088A (ko) 2018-01-26 2020-10-08 에프. 호프만-라 로슈 아게 방사성 표지된 올리고뉴클레오티드 및 이의 제조 방법
CN111699007A (zh) * 2018-01-29 2020-09-22 豪夫迈·罗氏有限公司 用于制备GalNAc寡核苷酸缀合物的方法
US11510939B1 (en) 2019-04-19 2022-11-29 Apellis Pharmaceuticals, Inc. RNAs for complement inhibition
AR118949A1 (es) * 2019-05-20 2021-11-10 Hoffmann La Roche Proceso para preparar epímeros de fosforamidita de galnac
CN114008061B (zh) 2019-06-20 2024-03-12 豪夫迈·罗氏有限公司 放射性标记的moem型寡核苷酸及其制备方法
CN110734372B (zh) * 2019-09-30 2024-09-24 兰州交通大学 一种合成烯丙基脂肪醇聚氧乙烯醚羧酸(apea-9)的方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008139299A (ja) * 2006-11-10 2008-06-19 National Institute Of Advanced Industrial & Technology 膜マイクロドメイン又はコレステロール認識タンパク質検出用高感度分子プローブ
WO2010108125A2 (en) * 2009-03-19 2010-09-23 The Johns Hopkins University Psma-targeting compounds and uses thereof
WO2011053614A1 (en) * 2009-10-30 2011-05-05 Merck Sharp & Dohme Corp. Crystalline cdm-nag and methods for producing same
CN102869774A (zh) * 2010-02-24 2013-01-09 箭头研究公司 用于靶向递送siRNA的组合物

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US156917A (en) * 1874-11-17 Improvement in car-couplings
US133170A (en) * 1872-11-19 Improvement in wheelbarrows
US1185198A (en) * 1912-11-25 1916-05-30 Elliott Co Tube-cleaning apparatus.
AU2009327322A1 (en) * 2008-12-19 2011-06-30 Pinnacle Pharmaceuticals, Inc. Phenazopyridine compounds
LT2603513T (lt) * 2010-08-10 2020-05-25 Takeda Pharmaceutical Company Limited Heterociklinis junginys ir jo panaudojimas kaip ampa receptoriaus teigiamo alosterinio moduliatoriaus
JP2014504295A (ja) * 2010-12-17 2014-02-20 アローヘッド リサーチ コーポレイション siRNA用ガラクトースクラスター−薬物動態調節剤標的指向部分
US8501930B2 (en) 2010-12-17 2013-08-06 Arrowhead Madison Inc. Peptide-based in vivo siRNA delivery system
BR112015027322A8 (pt) 2013-05-01 2018-01-02 Isis Pharmaceuticals Inc Compostos antissenso conjugados e sua utilização
MX391977B (es) 2013-06-27 2025-03-21 Roche Innovation Ct Copenhagen As Oligómeros antisentido y conjugados con diana en la proteína-convertasa subtilisina/kexina tipo 9(pcsk9).
KR20160083876A (ko) * 2013-11-14 2016-07-12 로슈 이노베이션 센터 코펜하겐 에이/에스 ApoB 안티센스 접합체 화합물
EP3845547A1 (en) 2014-05-01 2021-07-07 Ionis Pharmaceuticals, Inc. Galnac3 conjugated modified oligonucleotide for modulating angiopoietin-like 3 expression

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008139299A (ja) * 2006-11-10 2008-06-19 National Institute Of Advanced Industrial & Technology 膜マイクロドメイン又はコレステロール認識タンパク質検出用高感度分子プローブ
WO2010108125A2 (en) * 2009-03-19 2010-09-23 The Johns Hopkins University Psma-targeting compounds and uses thereof
WO2011053614A1 (en) * 2009-10-30 2011-05-05 Merck Sharp & Dohme Corp. Crystalline cdm-nag and methods for producing same
CN102869774A (zh) * 2010-02-24 2013-01-09 箭头研究公司 用于靶向递送siRNA的组合物

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
"Derivate von L-Methionin-sulfoxyd und ihre Verwendung für Peptidsynthesen";B. Iselin;《Helvetica Chimica Acta》;19611231;第44卷;第61-78页 *
"N-[2-Chloro-9H-purin-6-yl]-N-cyclopropylglycylamino acids and derivatives: Synthesis, evaluation as a class of novel analgesics, and 3D QSAR analysis";Jinghua Zhao et al.;《Bioorganic & Medicinal Chemistry》;20090723;第17卷;第6305-6310页 *
"Plasmin-Activated Prodrugs for Cancer Chemotherapy. 2. Synthesis and Biological Activity of Peptidyl Derivatives of Doxorubicin";Prasun K. Chakravarty et al.;《Journal of Medicinal Chemistry》;19831231;第26卷(第5期);第638-644页 *
"Selektive Spaltung substituierter Phenylsulfenyl-Schutzgruppen bei Peptidsynthesen";W. Kessler et al.;《Helvetica Chimica Acta》;19661231;第49卷;第1330-1344页 *
"Synthesis and DNA-Damaging Properties of Cisplatin-N-Mustard Conjugates";Stefan Schiesser et al.;《Eur. J. Org. Chem.》;20150430;第2015卷;第2654–2660页 *
"The synthesis of the pentapeptide related to the Gm(a) antigen of human gamma G-globulin";D.E. Nitecki et al.;《Australian Journal of Chemistry》;19691231;第22卷;第871-874页 *

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Publication number Publication date
MX369556B (es) 2019-11-12
PL3331892T3 (pl) 2019-11-29
JP2018523643A (ja) 2018-08-23
US20180162894A1 (en) 2018-06-14
HK1250717A1 (zh) 2019-01-11
HRP20191589T1 (hr) 2019-12-13
SI3331892T1 (sl) 2019-10-30
KR102579520B1 (ko) 2023-09-15
EP3331892A1 (en) 2018-06-13
MX2017015662A (es) 2018-04-18
EP3331892B1 (en) 2019-07-03
WO2017021385A1 (en) 2017-02-09
ES2744437T3 (es) 2020-02-25
CN107709342A (zh) 2018-02-16
AU2016302697A1 (en) 2017-10-26
KR20180030783A (ko) 2018-03-26
US10597417B2 (en) 2020-03-24
JP6940477B2 (ja) 2021-09-29
CA2982825C (en) 2023-10-17
AU2016302697B2 (en) 2020-10-29
BR112017021926A2 (pt) 2018-07-03
CA2982825A1 (en) 2017-02-09
IL256528B (en) 2020-01-30
IL256528A (en) 2018-02-28

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