WO2007138089A1 - Process for preparing substituted biphenyls - Google Patents
Process for preparing substituted biphenyls Download PDFInfo
- Publication number
- WO2007138089A1 WO2007138089A1 PCT/EP2007/055283 EP2007055283W WO2007138089A1 WO 2007138089 A1 WO2007138089 A1 WO 2007138089A1 EP 2007055283 W EP2007055283 W EP 2007055283W WO 2007138089 A1 WO2007138089 A1 WO 2007138089A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- palladium
- process according
- fluoro
- nitro
- palladium catalyst
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
Definitions
- the present invention relates to a process for preparing substituted biphenyls of the formula I
- X is fluorine or chlorine
- R 1 is nitro, amino or NHR 3 ;
- R 2 is cyano, nitro, halogen, Ci-C ⁇ -alkyl, Ci-C ⁇ -alkenyl, Ci-C ⁇ -alkynyl, Ci-C ⁇ -alkoxy, Ci-C ⁇ -haloalkyl, (Ci-C ⁇ -alkylJcarbonyl or phenyl;
- R 3 is Ci-C 4 -alkyl, Ci-C 4 -alkenyl or Ci-C 4 -alkynyl;
- n 1 , 2 or 3, where in case that n is 2 or 3, the R 2 radicals may also be different, which comprises reacting a compound of formula Il
- a base and of a palladium catalyst selected from the group of: a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand or c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine, in a solvent, with a diphenylborinic
- R 1 and n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.
- EP-A 0 888 261 discloses a process for preparing nitrobiphenyls by reacting chloronitrobenzenes with a phenylboronic acid in the presence of a palladium catalyst and of a base. In this process, a very high catalyst concentration is necessary.
- the diphenylborinic acid (III) is obtained by reaction of optionally substituted phenylmagnesium chloride V with trialkyl borate, preferably trimethyl borate, in tetrahydrofuran as a solvent according to scheme 1 which follows.
- R 4 is Ci-C4-alkyl, preferably methyl.
- substituted biphenyls prepared by the present process have the following preferred substituents, in each case both individually and in combination:
- R 1 nitro, amino, methylamino, propylamine butylamino, allylamino or propargyl- amino, more preferably nitro, amino or methylamino, most preferably nitro or amino;
- R 2 cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, allyl, propargyl, methoxy, ethoxy, trifluoromethyl or phenyl, more preferably fluorine, chlorine, methyl or methoxy, most preferably fluorine or chlorine;
- R 3 methyl, ethyl, propyl, butyl, allyl or propargyl, more preferably methyl, ethyl or allyl, most preferably methyl;
- diphenylborinic acids (III) in which n is 1 or 2, in particular 2.
- Particularly preferred are diphenylborinic acids (III) which are substituted in the 3- and 4-position.
- the compound (II) is used, based on the diphenylborinic acids (III) (diphenylborinic acid equivalents), normally in an equimolar amount, preferably with an up to 20 percent excess, in particular with an up to 50 percent excess.
- the bases used may be organic bases, for example tertiary amines. Preference is given to using, for example, triethylamine or dimethylcyclohexylamine.
- the bases used are preferably alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonates, alkaline earth metal carbonates, alkali metal hydrogen- carbonates, alkali metal acetates, alkaline earth metal acetates, alkali metal alkoxides and alkaline earth metal alkoxides, in a mixture and in particular individually.
- Particularly preferred bases are alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonates, alkaline earth metal carbonates and alkali metal hydrogencarbonates.
- alkali metal hydroxides e.g. sodium hydroxide and potassium hydroxide
- alkali metal carbonates and alkali metal hydrogencarbonates e.g. lithium carbonate, sodium carbonate and potassium carbonate.
- the base is used in the process according to the invention preferably with a fraction of from 100 to 500 mol%, more preferably from 150 to 400 mol%, based on the amount of diphenylborinic acid (III).
- Suitable palladium catalysts are palladium-ligand complexes with palladium in the zero oxidation state, salts of palladium in the presence of complex ligands, or metallic palladium optionally applied to support, preferably in the presence of complex ligands.
- Suitable complex ligands are uncharged ligands such as triarylphosphines and trialkylphosphines, which may optionally be substituted in the aryl rings, such as triphenylphosphine (TPP), di-1-adamantyl-n-butylphosphine, tri-tert-butylphosphine (TtBP) or 2-(dicyclohexylphosphino)biphenyl.
- TPP triphenylphosphine
- TtBP tri-tert-butylphosphine
- 2-(dicyclohexylphosphino)biphenyl 2-(dicyclohexylphosphino)biphenyl.
- the literature has also described further particularly reactive complex ligands from other structural classes, including 1 ,3-bis(2,6-diisopropylphenyl)-4,5-H2- imidazolium chloride (cf., for example, G.
- TBAB tetra-n-butylammonium bromide
- the water solubility of the palladium complexes can be improved by various substituents such as sulfonic acid or sulfonate salt groups, carboxylic acid or carboxylate salt groups, phosphonic acid, phosphonium or phosphonate salt groups, peralkylammonium, hydroxyl and polyether groups.
- substituents such as sulfonic acid or sulfonate salt groups, carboxylic acid or carboxylate salt groups, phosphonic acid, phosphonium or phosphonate salt groups, peralkylammonium, hydroxyl and polyether groups.
- the palladium is normally present in the two positive oxidation state.
- EP-A 0 888 261 describes the use of from 2 to 6 equivalents of triphenylphosphine per equivalent of the palladium catalyst.
- the use of high ligand excesses is generally viewed in the literature as disadvantageous, since this is expected to result in inactivation of the catalytically active complex (cf., for example, J. Hassan et al., Chem. Rev. 2002, 102, 1359).
- Metallic palladium is used preferably in pulverized form or on a support material, for example in the form of palladium on activated carbon, palladium on alumina, palladium on barium carbonate, palladium on barium sulfate, palladium on calcium carbonate, palladium aluminosilicates such as montmorillonite, palladium on SiU2 and palladium on calcium carbonate, in each case with a palladium content of from 0.5 to 12% by weight.
- these catalyst may comprise further dopants, for example lead.
- the palladium catalyst is used with a low fraction of from 0.001 to 1.0 mol%, preferably from 0.005 to 0.5 mol% or from 0.01 to 0.5 mol% and in particular from 0.005 to 0.05 mol%, based on the amount of compound (II).
- the process according to the invention may be carried out in a biphasic system composed of aqueous phase and solid phase, i.e. the catalyst.
- the aqueous phase may also comprise a water-soluble organic solvent in addition to water.
- Organic solvents suitable for the process according to the invention are ethers such as dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran, dioxane and tert- butyl methyl ether, hydrocarbons such as n-hexane, n-heptane, cyclohexane, benzene, toluene and xylene, alcohols such as methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, 1-butanol, 2-butanol and tert.-butanol, ketones such as acetone, ethyl methyl ketone and isobutyl methyl ketone, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, in each case individually or in a mixture.
- ethers such as dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran,
- Preferred solvents are ethers such as dimethoxyethane, tetrahydrofuran and dioxane, hydrocarbons such as cyclohexane, toluene and xylene, alcohols such as ethanol, 1- propanol, 2-propanol, 1-butanol and tert.-butanol, in each case individually or in a mixture.
- ethers such as dimethoxyethane, tetrahydrofuran and dioxane
- hydrocarbons such as cyclohexane, toluene and xylene
- alcohols such as ethanol, 1- propanol, 2-propanol, 1-butanol and tert.-butanol, in each case individually or in a mixture.
- water, one or more water-insoluble and one or more water-soluble solvents are used, for example mixtures of water and dioxane, or water and tetrahydrofuran, or water, dioxane and ethanol, or water, tetrahydrofuran and methanol, or water, toluene and tetrahydrofuran, preferably water and tetrahydrofuran, or water, tetrahydrofuran and methanol.
- the total amount of solvent is normally from 3000 to 500 g and preferably from 2000 to 700 g, per mole of the compound (II).
- the process is carried out by adding the compound (II), the diphenyl- borinic acids (III), the base and the catalytic amount of the palladium catalyst to a mixture of water and one or more inert organic solvents, and stirring at a temperature of from 50°C to 120°C, preferably from 70°C to 110 0 C, more preferably from 90°C to 100°C, for a period of from 1 to 50 hours, preferably from 2 to 24 hours.
- the reaction may be carried out in customary apparatus suitable for such processes.
- the process according to the invention affords the compounds I in very high up to quantitative yields at very good purity.
- substituted biphenyls obtainable by the process according to the invention are suitable as precursors for fungicidal crop protection active ingredients (cf. WO 03/070705).
- a reaction flask is initially charged with 0.55 g of sodium hydroxide (13.7 mM) and 50 m L of water at 15-20 0 C. To this are metered 2,5 g of di(3,4-dichlorophenyl)bo ⁇ nic acid (7.8 mM) and 0.199 g of triphenylphosphine (0.76 mM) in 50 mL of dioxane. After full addition, the reaction solution is stirred at 18-22°C for 40 minutes. After deoxygenation, 27 mg of palladium(ll) chloride (0.15 mM) and 1 ,4 g of 2-bromo-4-fluoro-aniline (7.4 mM) are added to the reaction solution.
- reaction flask is initially charged with 0.55 g of sodium hydroxide (13.7 mM) and 50 mL of water at 15-20 0 C.
Abstract
Description
Claims
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2007800034097A CN101374799B (en) | 2006-06-01 | 2007-05-31 | Process for preparing substituted biphenyls |
BRPI0707107-8A BRPI0707107A2 (en) | 2006-06-01 | 2007-05-31 | process for preparing substituted biphenyls and |
EA200801511A EA200801511A1 (en) | 2006-06-01 | 2007-05-31 | METHOD OF OBTAINING SUBSTITUTED BIPHENYLS |
US12/087,345 US7709684B2 (en) | 2006-06-01 | 2007-05-31 | Process for preparing substituted biphenyls |
EP07729695A EP2029519A1 (en) | 2006-06-01 | 2007-05-31 | Process for preparing substituted biphenyls |
CA002636695A CA2636695A1 (en) | 2006-06-01 | 2007-05-31 | Process for preparing substituted biphenyls |
JP2008554792A JP5107267B2 (en) | 2006-06-01 | 2007-05-31 | Process for producing substituted biphenyls |
AU2007267055A AU2007267055A1 (en) | 2006-06-01 | 2007-05-31 | Process for preparing substituted biphenyls |
IL192573A IL192573A (en) | 2006-06-01 | 2008-07-02 | Process for preparing substituted biphenyls |
US12/726,196 US8030527B2 (en) | 2006-06-01 | 2010-03-17 | Process for preparing substituted biphenyls |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06114872 | 2006-06-01 | ||
EP06114872.2 | 2006-06-01 | ||
EP06120319.6 | 2006-09-07 | ||
EP06120319 | 2006-09-07 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/087,345 A-371-Of-International US7709684B2 (en) | 2006-06-01 | 2007-05-31 | Process for preparing substituted biphenyls |
US12/726,196 Division US8030527B2 (en) | 2006-06-01 | 2010-03-17 | Process for preparing substituted biphenyls |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007138089A1 true WO2007138089A1 (en) | 2007-12-06 |
Family
ID=38330735
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/055283 WO2007138089A1 (en) | 2006-06-01 | 2007-05-31 | Process for preparing substituted biphenyls |
Country Status (11)
Country | Link |
---|---|
US (2) | US7709684B2 (en) |
EP (1) | EP2029519A1 (en) |
JP (1) | JP5107267B2 (en) |
KR (1) | KR20090014258A (en) |
AR (1) | AR061144A1 (en) |
AU (1) | AU2007267055A1 (en) |
BR (1) | BRPI0707107A2 (en) |
CA (1) | CA2636695A1 (en) |
EA (1) | EA200801511A1 (en) |
IL (1) | IL192573A (en) |
WO (1) | WO2007138089A1 (en) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008122555A1 (en) * | 2007-04-10 | 2008-10-16 | Saltigo Gmbh | 2-nitro-5-fluoro-3',4'-dichlorobiphenyl and method for the production thereof |
WO2009003650A1 (en) | 2007-06-29 | 2009-01-08 | Bayer Cropscience Ag | Preparation of biaryls |
EP2093216A1 (en) * | 2008-02-25 | 2009-08-26 | Bayer CropScience AG | Process for preparing substituted biphenylanilides |
EP2119697A1 (en) | 2008-05-09 | 2009-11-18 | Bayer CropScience AG | Process for preparing substituted biphenylanilides |
WO2010000856A1 (en) * | 2008-07-03 | 2010-01-07 | Basf Se | Method for producing aminobiphenylene |
WO2012120003A1 (en) | 2011-03-07 | 2012-09-13 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Process for the synthesis of aminobiphenylene |
EP2546229A1 (en) | 2011-07-15 | 2013-01-16 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Method for synthesising aminobiphenyls |
US8492558B2 (en) | 2009-02-19 | 2013-07-23 | Basf Se | Method for producing 2-aminobiphenylene |
WO2013132006A1 (en) | 2012-03-07 | 2013-09-12 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Method for synthesising aminobiphenyls using aryl hydrazines |
US8853455B2 (en) | 2009-03-09 | 2014-10-07 | Basf Se | Process for preparing substituted 2-nitrobiphenyls |
CN104478726A (en) * | 2014-12-01 | 2015-04-01 | 南通嘉禾化工有限公司 | Method of preparing 2-nitrobiphenyl compound |
CN105218378A (en) * | 2008-06-25 | 2016-01-06 | 巴斯夫欧洲公司 | Prepare the method for substituted biphenyl |
EP3009420A1 (en) | 2014-10-16 | 2016-04-20 | Bayer CropScience AG | Method for the production of biphenylamines from anilides using ruthenium catalysis |
US9868694B2 (en) | 2013-07-23 | 2018-01-16 | Bayer Cropscience Aktiengesellschaft | Process for preparing chlorinated biphenylanilides and biphenylanilines |
US10246407B2 (en) | 2014-04-25 | 2019-04-02 | Bayer Cropscience Aktiengesellschaft | Process for preparing biphenylamines from anilides by ruthenium catalysis |
US11827610B2 (en) | 2021-09-15 | 2023-11-28 | Enko Chem, Inc. | Protoporphyrinogen oxidase inhibitors |
Families Citing this family (4)
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AR052930A1 (en) * | 2005-03-02 | 2007-04-11 | Basf Ag | PROCEDURE FOR THE PREPARATION OF REPLACED BIFENILES |
US7821647B2 (en) * | 2008-02-21 | 2010-10-26 | Corning Incorporated | Apparatus and method for measuring surface topography of an object |
JP5178470B2 (en) * | 2008-11-19 | 2013-04-10 | 三井化学株式会社 | Method for producing fluorene derivative |
JP5602330B2 (en) * | 2012-08-20 | 2014-10-08 | マナック株式会社 | Method for producing borinic acid derivative and novel borinic acid derivative |
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2007
- 2007-05-31 WO PCT/EP2007/055283 patent/WO2007138089A1/en active Application Filing
- 2007-05-31 BR BRPI0707107-8A patent/BRPI0707107A2/en active Search and Examination
- 2007-05-31 EP EP07729695A patent/EP2029519A1/en not_active Withdrawn
- 2007-05-31 US US12/087,345 patent/US7709684B2/en not_active Expired - Fee Related
- 2007-05-31 CA CA002636695A patent/CA2636695A1/en not_active Abandoned
- 2007-05-31 EA EA200801511A patent/EA200801511A1/en unknown
- 2007-05-31 KR KR1020087017751A patent/KR20090014258A/en not_active Application Discontinuation
- 2007-05-31 AU AU2007267055A patent/AU2007267055A1/en not_active Abandoned
- 2007-05-31 AR ARP070102360A patent/AR061144A1/en not_active Application Discontinuation
- 2007-05-31 JP JP2008554792A patent/JP5107267B2/en not_active Expired - Fee Related
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2008
- 2008-07-02 IL IL192573A patent/IL192573A/en not_active IP Right Cessation
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2010
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WO2008122555A1 (en) * | 2007-04-10 | 2008-10-16 | Saltigo Gmbh | 2-nitro-5-fluoro-3',4'-dichlorobiphenyl and method for the production thereof |
WO2009003650A1 (en) | 2007-06-29 | 2009-01-08 | Bayer Cropscience Ag | Preparation of biaryls |
EP2185500B1 (en) * | 2007-06-29 | 2015-12-23 | Bayer Intellectual Property GmbH | Method for manufacturing biaryls |
TWI427064B (en) * | 2008-02-25 | 2014-02-21 | Bayer Cropscience Ag | Process for preparing substituted biphenylanilides |
EP2093216A1 (en) * | 2008-02-25 | 2009-08-26 | Bayer CropScience AG | Process for preparing substituted biphenylanilides |
WO2009106234A1 (en) * | 2008-02-25 | 2009-09-03 | Bayer Cropscience Ag | Process for preparing substituted biphenylanilides |
JP2011515335A (en) * | 2008-02-25 | 2011-05-19 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | Process for preparing substituted biphenylanilides |
CN101952253B (en) * | 2008-02-25 | 2013-05-01 | 拜耳作物科学股份公司 | Process for preparing substituted biphenylanilides |
EP2119697A1 (en) | 2008-05-09 | 2009-11-18 | Bayer CropScience AG | Process for preparing substituted biphenylanilides |
EP2280932B1 (en) * | 2008-05-09 | 2017-10-18 | Bayer Intellectual Property GmbH | Process for preparing substituted biphenylanilides |
JP2011519879A (en) * | 2008-05-09 | 2011-07-14 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | Process for preparing substituted biphenylanilides |
CN105218378A (en) * | 2008-06-25 | 2016-01-06 | 巴斯夫欧洲公司 | Prepare the method for substituted biphenyl |
WO2010000856A1 (en) * | 2008-07-03 | 2010-01-07 | Basf Se | Method for producing aminobiphenylene |
US8637707B2 (en) | 2008-07-03 | 2014-01-28 | Basf Se | Method for producing aminobiphenylene |
US8492558B2 (en) | 2009-02-19 | 2013-07-23 | Basf Se | Method for producing 2-aminobiphenylene |
US8853455B2 (en) | 2009-03-09 | 2014-10-07 | Basf Se | Process for preparing substituted 2-nitrobiphenyls |
WO2012120003A1 (en) | 2011-03-07 | 2012-09-13 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Process for the synthesis of aminobiphenylene |
EP2546229A1 (en) | 2011-07-15 | 2013-01-16 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Method for synthesising aminobiphenyls |
WO2013132006A1 (en) | 2012-03-07 | 2013-09-12 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Method for synthesising aminobiphenyls using aryl hydrazines |
US9868694B2 (en) | 2013-07-23 | 2018-01-16 | Bayer Cropscience Aktiengesellschaft | Process for preparing chlorinated biphenylanilides and biphenylanilines |
EP3418284A1 (en) | 2013-07-23 | 2018-12-26 | Bayer CropScience Aktiengesellschaft | Improved method for the preparation of chlorinated biphenylanilides and biphenylanilines |
US10246407B2 (en) | 2014-04-25 | 2019-04-02 | Bayer Cropscience Aktiengesellschaft | Process for preparing biphenylamines from anilides by ruthenium catalysis |
US10246408B2 (en) | 2014-04-25 | 2019-04-02 | Bayer Cropscience Aktiengesellschaft | Process for preparing biphenylamines from anilides by ruthenium catalysis |
EP3009420A1 (en) | 2014-10-16 | 2016-04-20 | Bayer CropScience AG | Method for the production of biphenylamines from anilides using ruthenium catalysis |
CN104478726A (en) * | 2014-12-01 | 2015-04-01 | 南通嘉禾化工有限公司 | Method of preparing 2-nitrobiphenyl compound |
US11827610B2 (en) | 2021-09-15 | 2023-11-28 | Enko Chem, Inc. | Protoporphyrinogen oxidase inhibitors |
Also Published As
Publication number | Publication date |
---|---|
EA200801511A1 (en) | 2009-06-30 |
JP5107267B2 (en) | 2012-12-26 |
IL192573A (en) | 2013-10-31 |
AR061144A1 (en) | 2008-08-06 |
US7709684B2 (en) | 2010-05-04 |
KR20090014258A (en) | 2009-02-09 |
CA2636695A1 (en) | 2007-12-06 |
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