WO1999036422A1 - Methods of synthesizing and screening inhibitors of bacterial nad synthetase enzyme, compounds thereof, and methods of treating bacterial and microbial infections with inhibitors of bacterial nad synthetase enzyme - Google Patents

Methods of synthesizing and screening inhibitors of bacterial nad synthetase enzyme, compounds thereof, and methods of treating bacterial and microbial infections with inhibitors of bacterial nad synthetase enzyme Download PDF

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Publication number
WO1999036422A1
WO1999036422A1 PCT/US1999/000810 US9900810W WO9936422A1 WO 1999036422 A1 WO1999036422 A1 WO 1999036422A1 US 9900810 W US9900810 W US 9900810W WO 9936422 A1 WO9936422 A1 WO 9936422A1
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WO
WIPO (PCT)
Prior art keywords
compound
integer
nad synthetase
synthetase enzyme
compounds
Prior art date
Application number
PCT/US1999/000810
Other languages
English (en)
French (fr)
Inventor
Wayne J. Brouillette
Donald Muccio
Mark J. Jedrzejas
Christie G. Brouillette
Yancho Devedjiev
Walter Cristofoli
Lawrence J. Delucas
Jose Gabriel Garcia
Laurent Schmitt
Original Assignee
The Uab Research Foundation
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 The Uab Research Foundation filed Critical The Uab Research Foundation
Priority to AU20317/99A priority Critical patent/AU2031799A/en
Priority to IL13722999A priority patent/IL137229A0/xx
Priority to DE69918799T priority patent/DE69918799D1/de
Priority to AT99900821T priority patent/ATE271555T1/de
Priority to JP2000540138A priority patent/JP2002509149A/ja
Priority to CA002317439A priority patent/CA2317439A1/en
Priority to EP99900821A priority patent/EP1047692B1/en
Priority to IL14151399A priority patent/IL141513A0/xx
Priority to AT99933622T priority patent/ATE256677T1/de
Priority to JP2000566269A priority patent/JP2002523412A/ja
Priority to CA002341506A priority patent/CA2341506A1/en
Priority to EP99933622A priority patent/EP1109805B1/en
Priority to DE69913712T priority patent/DE69913712T2/de
Priority to PCT/US1999/014839 priority patent/WO2000010996A1/en
Priority to AU49639/99A priority patent/AU4963999A/en
Publication of WO1999036422A1 publication Critical patent/WO1999036422A1/en
Priority to US09/617,258 priority patent/US6500852B1/en
Priority to US10/080,279 priority patent/US6861448B2/en
Priority to US10/281,407 priority patent/US6727237B2/en
Priority to AU2003261481A priority patent/AU2003261481A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79Acids; Esters
    • C07D213/80Acids; Esters in position 3
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/40Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/42Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/46Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/08Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/30Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12QMEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/48Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving transferase
    • CCHEMISTRY; METALLURGY
    • C40COMBINATORIAL TECHNOLOGY
    • C40BCOMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
    • C40B40/00Libraries per se, e.g. arrays, mixtures
PCT/US1999/000810 1998-01-14 1999-01-14 Methods of synthesizing and screening inhibitors of bacterial nad synthetase enzyme, compounds thereof, and methods of treating bacterial and microbial infections with inhibitors of bacterial nad synthetase enzyme WO1999036422A1 (en)

Priority Applications (19)

Application Number Priority Date Filing Date Title
AU20317/99A AU2031799A (en) 1998-01-14 1999-01-14 Methods of synthesizing and screening inhibitors of bacterial nad synthetase enzyme, compounds thereof, and methods of treating bacterial and microbial infections with inhibitors of bacterial nad synthetase enzyme
IL13722999A IL137229A0 (en) 1998-01-14 1999-01-14 Methods of synthesizing and screening inhibitors of bacterial nad synthetase enzyme, compounds thereof, and methods of treating bacterial and microbial infections with inhibitors of bacterial nad synthetase enzyme
DE69918799T DE69918799D1 (de) 1998-01-14 1999-01-14 Verfahren zur herstellung und screening von inhibitoren des bakteriellen nad synthetase enzyms, verbindungen daraus und methoden zur behandlung bakterieller und mikrobieller infektionen mit diesen inhibitoren
AT99900821T ATE271555T1 (de) 1998-01-14 1999-01-14 Verfahren zur herstellung und screening von inhibitoren des bakteriellen nad synthetase enzyms, verbindungen daraus und methoden zur behandlung bakterieller und mikrobieller infektionen mit diesen inhibitoren
JP2000540138A JP2002509149A (ja) 1998-01-14 1999-01-14 細菌nadシンテターゼ酵素の阻害剤の合成およびスクリーニング方法、その化合物、ならびに細菌nadシンテターゼ酵素の阻害剤を用いる細菌および微生物感染の治療方法
CA002317439A CA2317439A1 (en) 1998-01-14 1999-01-14 Methods of synthesizing and screening inhibitors of bacterial nad synthetase enzyme, compounds thereof, and methods of treating bacterial and microbial infections with inhibitors of bacterial nad synthetase enzyme
EP99900821A EP1047692B1 (en) 1998-01-14 1999-01-14 Methods of synthesizing and screening inhibitors of bacterial nad synthetase enzyme, compounds thereof and methods of treating bacterial and microbial infections with these inhibitors
JP2000566269A JP2002523412A (ja) 1998-08-25 1999-06-30 細菌nadシンテターゼ阻害剤
AT99933622T ATE256677T1 (de) 1998-08-25 1999-06-30 Inhibitoren der bakteriellen nad synthetase
IL14151399A IL141513A0 (en) 1998-08-25 1999-06-30 Inhibitors of bacterial nad synthetase
CA002341506A CA2341506A1 (en) 1998-08-25 1999-06-30 Inhibitors of bacterial nad synthetase
EP99933622A EP1109805B1 (en) 1998-08-25 1999-06-30 Inhibitors of bacterial nad synthetase
DE69913712T DE69913712T2 (de) 1998-08-25 1999-06-30 Inhibitoren der bakteriellen nad synthetase
PCT/US1999/014839 WO2000010996A1 (en) 1998-08-25 1999-06-30 Inhibitors of bacterial nad synthetase
AU49639/99A AU4963999A (en) 1998-08-25 1999-06-30 Inhibitors of bacterial nad synthetase
US09/617,258 US6500852B1 (en) 1998-01-14 2000-07-14 Inhibitors of bacterial NAD synthetase
US10/080,279 US6861448B2 (en) 1998-01-14 2002-02-22 NAD synthetase inhibitors and uses thereof
US10/281,407 US6727237B2 (en) 1998-01-14 2002-10-25 Inhibitors of bacterial NAD synthetase
AU2003261481A AU2003261481A1 (en) 1998-08-25 2003-11-06 Inhibitors of bacterial NAD synthetase

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US7139998P 1998-01-14 1998-01-14
US60/071,399 1998-01-14
US9788098P 1998-08-25 1998-08-25
US60/097,880 1998-08-25

Related Child Applications (3)

Application Number Title Priority Date Filing Date
PCT/US1999/014839 Continuation-In-Part WO2000010996A1 (en) 1998-01-14 1999-06-30 Inhibitors of bacterial nad synthetase
US09/617,258 Continuation-In-Part US6500852B1 (en) 1998-01-14 2000-07-14 Inhibitors of bacterial NAD synthetase
US09/617,258 Continuation US6500852B1 (en) 1998-01-14 2000-07-14 Inhibitors of bacterial NAD synthetase

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WO1999036422A1 true WO1999036422A1 (en) 1999-07-22

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PCT/US1999/000810 WO1999036422A1 (en) 1998-01-14 1999-01-14 Methods of synthesizing and screening inhibitors of bacterial nad synthetase enzyme, compounds thereof, and methods of treating bacterial and microbial infections with inhibitors of bacterial nad synthetase enzyme

Country Status (9)

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US (2) US6500852B1 (US06727237-20040427-C00087.png)
EP (1) EP1047692B1 (US06727237-20040427-C00087.png)
JP (1) JP2002509149A (US06727237-20040427-C00087.png)
AT (1) ATE271555T1 (US06727237-20040427-C00087.png)
AU (1) AU2031799A (US06727237-20040427-C00087.png)
CA (1) CA2317439A1 (US06727237-20040427-C00087.png)
DE (1) DE69918799D1 (US06727237-20040427-C00087.png)
IL (1) IL137229A0 (US06727237-20040427-C00087.png)
WO (1) WO1999036422A1 (US06727237-20040427-C00087.png)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001000197A2 (en) * 1999-06-29 2001-01-04 The Uab Research Foundation Methods of treating fungal infections with inhibitors of nad synthetase enzyme
WO2001055443A1 (en) * 2000-01-31 2001-08-02 Pharmacia & Upjohn Company Crystallization and structure determination of staphylococcus aureus nad synthetase
WO2002007516A2 (en) * 2000-07-14 2002-01-31 The Uab Research Foundation Uses for nad synthetase inhibitors
WO2001023330A3 (en) * 1999-09-29 2002-05-10 Upjohn Co Methods for creating a compound library and identifying lead chemical templates and ligands for target molecules
US6500852B1 (en) 1998-01-14 2002-12-31 University Of Alabama Research Foundation Inhibitors of bacterial NAD synthetase
US6673827B1 (en) 1999-06-29 2004-01-06 The Uab Research Foundation Methods of treating fungal infections with inhibitors of NAD synthetase enzyme
US6677160B1 (en) 1999-09-29 2004-01-13 Pharmacia & Upjohn Company Methods for creating a compound library and identifying lead chemical templates and ligands for target molecules
US6764858B2 (en) 1999-09-29 2004-07-20 Pharmacia & Upjohn Company Methods for creating a compound library
WO2005002337A1 (en) * 2003-04-02 2005-01-13 Virtual Drug Development, Inc. Disinfectant compositions and methods
US6861448B2 (en) 1998-01-14 2005-03-01 Virtual Drug Development, Inc. NAD synthetase inhibitors and uses thereof
WO2005054198A2 (en) * 2003-12-05 2005-06-16 University Of Bath Therapeutics use of pyridinium compounds to modulate naadp activity
EP1652839A2 (en) * 1999-10-28 2006-05-03 Daiichi Pharmaceutical Co., Ltd. Drug efflux pump inhibitor
US7056917B2 (en) 2001-04-26 2006-06-06 Daiichi Pharmaceutical Co., Ltd. Drug efflux pump inhibitor
WO2007005845A1 (en) * 2005-07-01 2007-01-11 Jenrin Discovery Mao-b inhibitors useful for treating obesity
US7514457B2 (en) 2005-05-31 2009-04-07 Pfizer Inc. Substituted aryloxymethyl bicyclicmethyl acetamide compounds
US7696240B2 (en) 2005-12-15 2010-04-13 Hoffmann-La Roche Inc. Fused pyrrole derivatives
US8710232B2 (en) 2004-04-22 2014-04-29 Sanofi-Aventis Deutschland Gmbh Imidazole derivatives used as TAFIa inhibitors
US8940901B2 (en) 2010-11-11 2015-01-27 Sanofi Process for the preparation of 3-(6-amino-pyridin-3yl)-2-acrylic acid derivatives
US8993560B2 (en) 2011-03-11 2015-03-31 Glaxo Group Limited Compounds

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AU2003245575A1 (en) * 2002-06-19 2004-01-06 University Of Rochester Oligonucleotide directed misfolding of rna
ATE554766T1 (de) * 2003-06-27 2012-05-15 Jackson H M Found Military Med Amphiphile pyridinium-verbindungen, herstellungsverfahren und ihre verwendung
JP5629447B2 (ja) * 2009-10-07 2014-11-19 株式会社セイシン企業 粒子性状の測定方法及び装置並びに測定試料の調製装置
US8889730B2 (en) 2012-04-10 2014-11-18 Pfizer Inc. Indole and indazole compounds that activate AMPK
JP6064062B2 (ja) 2013-03-15 2017-01-18 ファイザー・インク Ampkを活性化させるインダゾール化合物
CN110074138B (zh) * 2019-06-18 2020-05-08 江西顺泉生物科技有限公司 一种解淀粉芽孢杆菌油悬浮剂

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US6500852B1 (en) 2002-12-31
DE69918799D1 (de) 2004-08-26
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