WO2001000595A1 - Verfahren zur herstellung von 2-heterocyclylmethyl-benzoesäurederivaten - Google Patents

Verfahren zur herstellung von 2-heterocyclylmethyl-benzoesäurederivaten Download PDF

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Publication number
WO2001000595A1
WO2001000595A1 PCT/EP2000/005412 EP0005412W WO0100595A1 WO 2001000595 A1 WO2001000595 A1 WO 2001000595A1 EP 0005412 W EP0005412 W EP 0005412W WO 0100595 A1 WO0100595 A1 WO 0100595A1
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WO
WIPO (PCT)
Prior art keywords
halogen
optionally
carbon atoms
substituted
chlorine
Prior art date
Application number
PCT/EP2000/005412
Other languages
German (de)
English (en)
French (fr)
Inventor
Heinz-Jürgen Wroblowsky
Otto Schallner
Hans-Georg Schwarz
Original Assignee
Bayer Aktiengesellschaft
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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU55325/00A priority Critical patent/AU5532500A/en
Priority to BR0012451-6A priority patent/BR0012451A/pt
Priority to MXPA01013263A priority patent/MXPA01013263A/es
Priority to JP2001507005A priority patent/JP2003503396A/ja
Priority to EP00940367A priority patent/EP1194419A1/de
Priority to IL14666200A priority patent/IL146662A0/xx
Publication of WO2001000595A1 publication Critical patent/WO2001000595A1/de
Priority to HK03100101.3A priority patent/HK1047932A1/zh

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic 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
    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/60—Heterocyclic 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30—Phthalazines
    • C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/04—1,2,3-Triazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2

Definitions

  • the invention relates to a new process for the preparation of 2-heterocyclyl-methyl-benzoic acid derivatives, which as intermediates for the preparation of
  • Active ingredients for pharmaceutical and agricultural applications can be used.
  • n the numbers 0, 1, 2 or 3
  • X stands for nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, and Z represents heterocyclyl bound via N (nitrogen),
  • n and X have the meaning given above,
  • the 2-heterocyclylmethyl-benzoic acid derivatives of the general formula (1) can be obtained selectively in good yields and in high purity by the process according to the invention, although according to the prior art given above, the formation of N-heterocyclyl to a large extent as a side reaction -2-hydroxymethyl-benzamide derivatives was expected.
  • the process according to the invention represents a technically well practicable route to 2-heterocyclylmethyl-benzoic acid derivatives based on phthalides which are easily accessible by known methods.
  • the desired benzoic acid derivatives are immediately obtained when the ring is opened. i
  • n is preferably the number 0, 1, 2 or 3.
  • X preferably represents nitro, cyano, carbamoyl, thiocarbamoyl, halogen, each optionally substituted by halogen, Cj -C ⁇ alkoxy, C] -C4-alkylthio, C] -C4-alkylsulfinyl or -C-C4-alkylsulfonyl-substituted alkyl, alkoxy,
  • Z preferably represents one of the heterocyclic group
  • Q oxygen or sulfur
  • Rl for hydrogen, hydroxyl, mercapto, cyano, halogen, for alkyl optionally substituted by cyano, halogen, C 1 -C 4 alkoxy, C] -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl , Alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having up to 6 carbon atoms in the alkyl groups, for each alkylamino or dialkylamino optionally substituted by halogen, each having up to 6 carbon atoms in the alkyl groups, each optionally using halogen Substituted alkenyl, alkynyl, alkenyloxy, alkenylthio or alkenylamino, each having up to 6 carbon atoms in the alkenyl or alkyny
  • Cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl part, or for each optionally by Halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, or - in the event that two adjacent radicals R 1 and R 1 are attached to a double bond are - together with the adjacent radical R 1 also represents a benzo group, and
  • R ⁇ for hydrogen, hydroxy, A ino, alkylidene amino with up to 4 carbon atoms, for each optionally substituted by cyano, halogen or C ] -C4-alkoxy alkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino each with up to 6 carbon atoms in the alkyl groups, each for alkenyl, alkynyl or alkenyloxy optionally substituted by halogen, each having up to 6 carbon atoms in the alkenyl or alkynyl groups, for cycloalkyl, cycloalkylalkyl or cycloalkylamino, each optionally substituted by halogen, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl part, or for phenyl or benzyl optionally substituted in each case by halogen, C1-C4-alkyl or Cj
  • n particularly preferably represents the numbers 0, 1 or 2.
  • X particularly preferably represents nitro, cyano, carbamoyl, thiocarbamoyl,
  • Q represents oxygen or sulfur
  • R ' for hydrogen, hydroxy, mercapto, cyano, fluorine, chlorine, bromine, iodine, for each optionally by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i -Propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i- propylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy
  • Benzo grouping stands, and R ⁇ for hydrogen, hydroxyl, amino, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- each optionally substituted by fluorine and / or chlorine, methoxy or ethoxy or i-propoxy, methylamino, ethylamino or dimethylamino, for each optionally substituted by fluorine and / or chlorine, ethenyl, propenyl, ethynyl, propynyl or propenyloxy, for each optionally substituted by fluorine and / or chlorine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl , Cyclobutylmethyl, Cyclopentylmethyl or Cyclohexylmethyl, or for each optionally by fluorine, chlorine
  • R 1 and R 2 are defined as in the particularly preferred definitions of Z.
  • R 1 and R 2 are defined as in the most particularly preferred definitions of Z.
  • the phthalides of the general formula (II) required as starting materials in the process according to the invention are known and / or can be prepared by processes known per se (cf. Heterocycles 31 (1990), 1261-1270; Synth. Commun. 20 (1990), 2641 -2652; J. Org. Chem. 57 (1992), 2029-2033).
  • the alkali metal and alkaline earth metal salts such as the lithium, sodium, rubidium, cesium, magnesium, calcium and barium salts, very particularly preferably the sodium and potassium salts of these compounds become.
  • Formula (I) is carried out using an aprotic polar diluent.
  • aprotic polar diluent include in particular ethers such as diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone, methyl isopropyl ketone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide,
  • Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, and sulfones such as tetramethylene sulfone (sulfolane).
  • Ketones such as methyl isobutyl ketone
  • amides such as N, N-dimethyl formamide and N, N-dimethyl acetamide, are very particularly preferred as diluents.
  • the process according to the invention for the preparation of the compounds of the general formula (I) is optionally carried out using a basic reaction auxiliary.
  • the usual inorganic or organic bases or acid acceptors are generally suitable. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, Sodium or potassium methoxide, ethanolate, n or i-propanolate, n, i, s or t-butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl diisopropylamine, N, N-
  • Alkali metal and alkaline earth metal hydrides, hydroxides and alkanolates such as lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, - ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate are very particularly preferred as basic reaction auxiliaries.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 200 ° C, preferably between 10 ° C and 180 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to increase the process according to the invention or reduced pressure - generally between 0.1 bar and 10 bar.
  • 1 mole of phthalide of the general formula (II) is generally between 0.8 and 1.2 mole, preferably between 0.95 and 1.05 mole, of nitrogen heterocycle of the general formula (III) or a salt of this one.
  • reaction components are mixed at room temperature or with cooling and the reaction mixture is then
  • the workup can be carried out according to customary methods.
  • the mixture is concentrated under reduced pressure, the residue is washed with an organic solvent which is practically immiscible with water, then in
  • the 2-heterocyclylmethylbenzoic acid derivatives of the general formula (I) to be prepared by the process according to the invention can be used as intermediates for

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
PCT/EP2000/005412 1999-06-26 2000-06-13 Verfahren zur herstellung von 2-heterocyclylmethyl-benzoesäurederivaten WO2001000595A1 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU55325/00A AU5532500A (en) 1999-06-26 2000-06-13 Method for producing 2-heterocyclyl methyl benzoic acid derivatives
BR0012451-6A BR0012451A (pt) 1999-06-26 2000-06-13 Processo para a preparação de derivados de ácido 2-heterociclilmetil-benzóico
MXPA01013263A MXPA01013263A (es) 1999-06-26 2000-06-13 Procedimiento para la obtencion de derivados del acido 2-heterociclilmetil-benzoico.
JP2001507005A JP2003503396A (ja) 1999-06-26 2000-06-13 ２−ヘテロシクリルメチル安息香酸誘導体の製造方法
EP00940367A EP1194419A1 (de) 1999-06-26 2000-06-13 Verfahren zur herstellung von 2-heterocyclylmethyl-benzoesäurederivaten
IL14666200A IL146662A0 (en) 1999-06-26 2000-06-13 Method for producing 2-heterocyclyl methyl benzoic acid derivatives
HK03100101.3A HK1047932A1 (zh) 1999-06-26 2003-01-03 製備2-雜環基甲基苯甲酸衍生物的方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19929348A DE19929348A1 (de) 1999-06-26 1999-06-26 Verfahren zur Herstellung von 2-Heterocyclylmethyl-benzoesäurederivaten
DE19929348.1 1999-06-26

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WO2001000595A1 true WO2001000595A1 (de) 2001-01-04

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EP (1) EP1194419A1 (zh)
JP (1) JP2003503396A (zh)
CN (1) CN1358176A (zh)
AU (1) AU5532500A (zh)
BR (1) BR0012451A (zh)
DE (1) DE19929348A1 (zh)
HK (1) HK1047932A1 (zh)
IL (1) IL146662A0 (zh)
MX (1) MXPA01013263A (zh)
WO (1) WO2001000595A1 (zh)

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6914082B2 (en) 2001-12-14 2005-07-05 Conocophillips Company Slurry bubble reactor operated in well-mixed gas flow regime
US7230035B2 (en) 2002-12-30 2007-06-12 Conocophillips Company Catalysts for the conversion of methane to synthesis gas
US8084481B2 (en) 2006-05-23 2011-12-27 Bayer Pharma Aktiengesellschaft Substituted arylimidazolone and triazolone as inhibitors of vasopressin receptors
US8114868B2 (en) 2008-07-25 2012-02-14 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8138178B2 (en) 2008-05-01 2012-03-20 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8202857B2 (en) 2008-02-11 2012-06-19 Vitae Pharmaceuticals, Inc. 1,3-oxazepan-2-one and 1,3-diazepan-2-one inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8202895B2 (en) 2009-03-18 2012-06-19 Bayer Pharma Aktiengesellschaft Substituted 2-acetamido-5-aryl-1,2,4-triazolones and use thereof
US8242111B2 (en) 2008-05-01 2012-08-14 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8329897B2 (en) 2007-07-26 2012-12-11 Vitae Pharmaceuticals, Inc. Synthesis of inhibitors of 11β-hydroxysteroid dehydrogenase type 1
US8440658B2 (en) 2007-12-11 2013-05-14 Vitae Pharmaceuticals, Inc. Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8569292B2 (en) 2008-05-01 2013-10-29 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8592409B2 (en) 2008-01-24 2013-11-26 Vitae Pharmaceuticals, Inc. Cyclic carbazate and semicarbazide inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8592410B2 (en) 2008-05-01 2013-11-26 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
US8598160B2 (en) 2008-02-15 2013-12-03 Vitae Pharmaceuticals, Inc. Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1
US8637505B2 (en) 2009-02-04 2014-01-28 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8680281B2 (en) 2008-01-07 2014-03-25 Vitae Pharmaceuticals, Inc. Lactam inhibitors of 11-β-hydroxysteroid dehydrogenase 1
US8680093B2 (en) 2009-04-30 2014-03-25 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8765744B2 (en) 2010-06-25 2014-07-01 Boehringer Ingelheim International Gmbh Azaspirohexanones
US8835426B2 (en) 2007-02-26 2014-09-16 Vitae Pharmaceuticals, Inc. Cyclic urea and carbamate inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8846668B2 (en) 2008-07-25 2014-09-30 Vitae Pharmaceuticals, Inc. Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8846613B2 (en) 2010-11-02 2014-09-30 Boehringer Ingelheim International Gmbh Pharmaceutical combinations for the treatment of metabolic disorders
US8859601B2 (en) 2008-12-06 2014-10-14 Bayer Intellectual Property Gmbh Substituted benzyl and phenylsulfonyl triazolones, and use thereof
US8883778B2 (en) 2009-07-01 2014-11-11 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11 beta-hydroxysteroid dehydrogenase 1
US8927539B2 (en) 2009-06-11 2015-01-06 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 based on the 1,3-oxazinan-2-one structure
US8933072B2 (en) 2010-06-16 2015-01-13 Vitae Pharmaceuticals, Inc. Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
US9034855B2 (en) 2010-09-16 2015-05-19 Bayer Intellectual Property Gmbh Substituted phenylacetate and phenylpropane amides and use thereof
US9180120B2 (en) 2010-09-02 2015-11-10 Bayer Intellectual Property Gmbh Substituted N-phenethyltriazoloneacetamides and use thereof
US9187466B2 (en) 2010-02-27 2015-11-17 Bayer Intellectual Property Gmbh Bisaryl-bonded aryltriazolones and use thereof
US9771352B2 (en) 2014-11-03 2017-09-26 Bayer Pharma Aktiengesellschaft Hydroxyalkyl-substituted phenyltriazole derivatives and uses thereof
US9988367B2 (en) 2016-05-03 2018-06-05 Bayer Pharma Aktiengesellschaft Amide-substituted pyridinyltriazole derivatives and uses thereof

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Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6914082B2 (en) 2001-12-14 2005-07-05 Conocophillips Company Slurry bubble reactor operated in well-mixed gas flow regime
US7230035B2 (en) 2002-12-30 2007-06-12 Conocophillips Company Catalysts for the conversion of methane to synthesis gas
US8084481B2 (en) 2006-05-23 2011-12-27 Bayer Pharma Aktiengesellschaft Substituted arylimidazolone and triazolone as inhibitors of vasopressin receptors
US8835426B2 (en) 2007-02-26 2014-09-16 Vitae Pharmaceuticals, Inc. Cyclic urea and carbamate inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8329897B2 (en) 2007-07-26 2012-12-11 Vitae Pharmaceuticals, Inc. Synthesis of inhibitors of 11β-hydroxysteroid dehydrogenase type 1
US8575156B2 (en) 2007-07-26 2013-11-05 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8748444B2 (en) 2007-12-11 2014-06-10 Vitae Pharmaceuticals, Inc. Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8440658B2 (en) 2007-12-11 2013-05-14 Vitae Pharmaceuticals, Inc. Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8680281B2 (en) 2008-01-07 2014-03-25 Vitae Pharmaceuticals, Inc. Lactam inhibitors of 11-β-hydroxysteroid dehydrogenase 1
US8592409B2 (en) 2008-01-24 2013-11-26 Vitae Pharmaceuticals, Inc. Cyclic carbazate and semicarbazide inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8202857B2 (en) 2008-02-11 2012-06-19 Vitae Pharmaceuticals, Inc. 1,3-oxazepan-2-one and 1,3-diazepan-2-one inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8598160B2 (en) 2008-02-15 2013-12-03 Vitae Pharmaceuticals, Inc. Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1
US8242111B2 (en) 2008-05-01 2012-08-14 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8569292B2 (en) 2008-05-01 2013-10-29 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8592410B2 (en) 2008-05-01 2013-11-26 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
US8138178B2 (en) 2008-05-01 2012-03-20 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8114868B2 (en) 2008-07-25 2012-02-14 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
US8754076B2 (en) 2008-07-25 2014-06-17 Vitae Pharmaceuticals, Inc./Boehringer-Ingelheim Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8846668B2 (en) 2008-07-25 2014-09-30 Vitae Pharmaceuticals, Inc. Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8859601B2 (en) 2008-12-06 2014-10-14 Bayer Intellectual Property Gmbh Substituted benzyl and phenylsulfonyl triazolones, and use thereof
US8637505B2 (en) 2009-02-04 2014-01-28 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8202895B2 (en) 2009-03-18 2012-06-19 Bayer Pharma Aktiengesellschaft Substituted 2-acetamido-5-aryl-1,2,4-triazolones and use thereof
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CN1358176A (zh) 2002-07-10
HK1047932A1 (zh) 2003-03-14
BR0012451A (pt) 2002-04-02
JP2003503396A (ja) 2003-01-28
EP1194419A1 (de) 2002-04-10
IL146662A0 (en) 2002-07-25
DE19929348A1 (de) 2000-12-28
AU5532500A (en) 2001-01-31
MXPA01013263A (es) 2002-06-21

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