ATE530516T1 - Exo- und diastereoselektive synthese von himbacin-analoga - Google Patents

Exo- und diastereoselektive synthese von himbacin-analoga

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Publication number
ATE530516T1
ATE530516T1 AT10001844T AT10001844T ATE530516T1 AT E530516 T1 ATE530516 T1 AT E530516T1 AT 10001844 T AT10001844 T AT 10001844T AT 10001844 T AT10001844 T AT 10001844T AT E530516 T1 ATE530516 T1 AT E530516T1
Authority
AT
Austria
Prior art keywords
exo
diastereoselective synthesis
himbacin
analogs
himbacin analogs
Prior art date
Application number
AT10001844T
Other languages
English (en)
Inventor
George G Wu
Anantha Sudhakar
Tao Wang
Ji Xie
Frank Xing Chen
Marc Poirier
Mingsheng Huang
Vijay Sabesen
Daw-Long Kwok
Jian Cui
Xiaojing Yang
Tiruvettipuram K Thiruvengadam
Jing Liao
Original Assignee
Schering Corp
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 Schering Corp filed Critical Schering Corp
Application granted granted Critical
Publication of ATE530516T1 publication Critical patent/ATE530516T1/de

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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06Preparation of nitro compounds
    • C07C201/10Preparation of nitro compounds by substitution of functional groups by nitro groups
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06Preparation of nitro compounds
    • C07C201/12Preparation of nitro compounds by reactions not involving the formation of nitro groups
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/44Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/55Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/10Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/12Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/28Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and unsaturated
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01Sulfonic acids
    • C07C309/02Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/08Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing hydroxy groups bound to the carbon skeleton
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/606Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom having only or additionally carbon-to-carbon triple bonds as unsaturation in the carboxylic acid moiety
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    • 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
    • C07C69/73Esters 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 unsaturated acids
    • C07C69/732Esters 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 unsaturated acids of unsaturated hydroxy carboxylic acids
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62Benzothiazoles
    • C07D277/64Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/92Naphthofurans; Hydrogenated naphthofurans
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/56Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
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    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576Six-membered rings
    • C07F9/58Pyridine rings
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    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • 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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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Peptides Or Proteins (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
AT10001844T 2005-01-14 2006-01-12 Exo- und diastereoselektive synthese von himbacin-analoga ATE530516T1 (de)

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US64446405P 2005-01-14 2005-01-14

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ATE530516T1 true ATE530516T1 (de) 2011-11-15

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AT06718069T ATE458726T1 (de) 2005-01-14 2006-01-12 Exo- und diastereoselektive synthese von himbacin-analoga
AT10001844T ATE530516T1 (de) 2005-01-14 2006-01-12 Exo- und diastereoselektive synthese von himbacin-analoga

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US (4) US7605275B2 (de)
EP (4) EP2206697B1 (de)
JP (3) JP4681616B2 (de)
CN (2) CN102757423B (de)
AR (1) AR056919A1 (de)
AT (2) ATE458726T1 (de)
CA (2) CA2875768C (de)
CY (2) CY1109896T1 (de)
DE (1) DE602006012450D1 (de)
DK (2) DK2206697T3 (de)
ES (3) ES2412981T3 (de)
HR (2) HRP20100218T1 (de)
ME (1) ME01967B (de)
MX (1) MX2007008665A (de)
PL (2) PL1848705T3 (de)
PT (2) PT1848705E (de)
RS (2) RS51315B (de)
SG (2) SG158888A1 (de)
SI (2) SI1848705T1 (de)
WO (1) WO2006076415A2 (de)
ZA (1) ZA200706711B (de)

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SG158885A1 (en) * 2005-01-14 2010-02-26 Schering Corp Synthesis of himbacine analogs
EP2206697B1 (de) 2005-01-14 2011-10-26 Schering Corporation Exo- und diastereoselektive Synthese von Himbacin-Analoga
US7772276B2 (en) * 2005-01-14 2010-08-10 Schering Corporation Exo-selective synthesis of himbacine analogs
BRPI0620641A2 (pt) * 2005-12-22 2011-11-16 Schering Corp usos de compostos antagonistas de receptor de trombina na profilaxia de complicações de cirurgia cardiopulmonar
AR061727A1 (es) * 2006-06-30 2008-09-17 Schering Corp Sintesis de dietil [[ 5- ( 3-fluorofenil) -piridin -2il] metil] fosfonato
JP5099563B2 (ja) * 2006-06-30 2012-12-19 メルク・シャープ・アンド・ドーム・コーポレーション 3−(5−ニトロシクロヘキサ−1−エニル)アクリル酸およびそのエステルの合成
EP2121604A2 (de) * 2006-12-15 2009-11-25 Schering Corporation Bisulfitaufreinigung eines alpha-ketoamids
ES2667945T3 (es) 2007-10-08 2018-05-16 Aurinia Pharmaceuticals Inc. Composiciones oftálmicas que comprenden inhibidores de calcineurina o Inhibidores de mTOR
CN101910148B (zh) * 2007-10-24 2014-06-04 默沙东公司 制备十二氢-萘并-呋喃基-氨基甲酸酯中间体的高纯度合成方法
US9120935B2 (en) * 2011-06-21 2015-09-01 Bluestar Silicones France Sas Hydrosilylation reaction inhibitors, and use thereof for preparing stable curable silicone compositions
CN105330689B (zh) * 2014-08-08 2018-08-17 博瑞生物医药(苏州)股份有限公司 制备Himbacine类似物中间体的制备方法
CN105985303B (zh) * 2015-02-13 2020-08-14 上海彩迩文生化科技有限公司 抗凝血剂的制备方法、中间体及其制备方法
CN105348241B (zh) * 2015-12-11 2017-09-05 南京华威医药科技开发有限公司 一种硫酸沃拉帕沙中间体的合成方法
US11247940B2 (en) 2016-10-26 2022-02-15 The Regents Of The University Of California Efficient integration of manufacturing of upcycled concrete product into power plants
CN106749138B (zh) * 2016-12-07 2019-08-16 扬子江药业集团四川海蓉药业有限公司 一种硫酸沃拉帕沙中间体醛的制备方法
CN106866450B (zh) * 2017-01-13 2019-01-11 阜阳欣奕华材料科技有限公司 硫酸沃拉帕沙中间体的制备方法
CN108658910B (zh) * 2017-03-29 2020-11-03 北京新领先医药科技发展有限公司 一种沃拉帕沙中间体1-α的制备方法
US20190224275A1 (en) 2017-05-12 2019-07-25 Aurinia Pharmaceuticals Inc. Protocol for treatment of lupus nephritis
US11230473B2 (en) 2017-06-30 2022-01-25 The Regents Of The University Of California CO2 mineralization in produced and industrial effluent water by pH-swing carbonation
WO2019036386A1 (en) 2017-08-14 2019-02-21 The Regents Of The University Of California MITIGATION OF THE ALKALI-SILICA REACTION IN CONCRETE USING EASILY SOLUBLE CHEMICAL ADDITIVES
WO2019057946A1 (en) 2017-09-25 2019-03-28 F. Hoffmann-La Roche Ag MULTI-CYCLIC AROMATIC COMPOUNDS AS D-FACTOR INHIBITORS
US11384029B2 (en) 2019-03-18 2022-07-12 The Regents Of The University Of California Formulations and processing of cementitious components to meet target strength and CO2 uptake criteria
WO2023069370A1 (en) 2021-10-18 2023-04-27 The Regents Of The University Of California Integration of direct air capture system into co2 mineralizaton process of concretes and aggregates
US12246993B2 (en) 2022-02-21 2025-03-11 Carbonbuilt Methods and systems for biomass-derived CO2 sequestration in concretes and aggregates
WO2023200905A1 (en) 2022-04-12 2023-10-19 Carbonbuilt Process for production of hydraulic-carbonating binder systems through mechanochemical activation of minerals
WO2024020027A1 (en) 2022-07-18 2024-01-25 The Regents Of The University Of Calfornia A multi-chambered electrochemical cell for carbon dioxide removal
WO2024237983A2 (en) 2023-01-31 2024-11-21 The Regents Of The University Of California Oxygen-selective anodes

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US7442712B2 (en) * 2004-05-28 2008-10-28 Schering Corporation Constrained himbacine analogs as thrombin receptor antagonists
SG158885A1 (en) * 2005-01-14 2010-02-26 Schering Corp Synthesis of himbacine analogs
US7541471B2 (en) * 2005-01-14 2009-06-02 Schering Corporation Synthesis of himbacine analogs
EP2206697B1 (de) 2005-01-14 2011-10-26 Schering Corporation Exo- und diastereoselektive Synthese von Himbacin-Analoga
US7772276B2 (en) * 2005-01-14 2010-08-10 Schering Corporation Exo-selective synthesis of himbacine analogs

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PT1848705E (pt) 2010-05-10
PL2206697T3 (pl) 2012-03-30
DE602006012450D1 (de) 2010-04-08
EP2196454B1 (de) 2014-08-27
DK2206697T3 (da) 2012-02-13
EP1848705A2 (de) 2007-10-31
MX2007008665A (es) 2008-03-04
CN102757423A (zh) 2012-10-31
EP2206697A1 (de) 2010-07-14
JP2011098967A (ja) 2011-05-19
ES2339696T3 (es) 2010-05-24
EP2196454A3 (de) 2010-09-22
PL1848705T3 (pl) 2010-07-30
JP5911447B2 (ja) 2016-04-27
US20110251392A1 (en) 2011-10-13
SI1848705T1 (sl) 2010-06-30
JP2008526972A (ja) 2008-07-24
SG192505A1 (en) 2013-08-30
ES2374379T3 (es) 2012-02-16
US7605275B2 (en) 2009-10-20
CA2594871C (en) 2015-04-07
SG158888A1 (en) 2010-02-26
CA2594871A1 (en) 2006-07-20
WO2006076415A2 (en) 2006-07-20
CA2875768C (en) 2018-03-06
RS51315B (sr) 2010-12-31
US8258319B2 (en) 2012-09-04
CY1109896T1 (el) 2014-09-10
RS52117B (sr) 2012-08-31
CY1112371T1 (el) 2015-12-09
DK1848705T3 (da) 2010-06-14
JP5388231B2 (ja) 2014-01-15
JP2013177407A (ja) 2013-09-09
CN101193880B (zh) 2012-08-22
EP2196468A1 (de) 2010-06-16
ATE458726T1 (de) 2010-03-15
EP2206697B1 (de) 2011-10-26
US20090281321A1 (en) 2009-11-12
ME01967B (me) 2012-08-31
ZA200706711B (en) 2014-01-29
US8618314B2 (en) 2013-12-31
HRP20100218T1 (hr) 2010-05-31
HRP20110963T1 (hr) 2012-01-31
AR056919A1 (es) 2007-11-07
CA2875768A1 (en) 2006-07-20
CN102757423B (zh) 2016-04-20
HK1108893A1 (en) 2008-05-23
SI2206697T1 (sl) 2012-02-29
PT2206697E (pt) 2012-01-10
US20060247450A1 (en) 2006-11-02
JP4681616B2 (ja) 2011-05-11
ES2412981T3 (es) 2013-07-15
EP2196468B1 (de) 2013-04-10
US7989653B2 (en) 2011-08-02
EP2196454A2 (de) 2010-06-16
WO2006076415A3 (en) 2006-11-16
CN101193880A (zh) 2008-06-04
US20120296093A1 (en) 2012-11-22
EP1848705B1 (de) 2010-02-24

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